Garcinia Plant Species of African Origin

Transcription

Garcinia Plant Species of African Origin
Understanding the medicinal potential of African Garcinia species
Garcinia Plant Species of African Origin:
Ethnobotanical, Pharmacological
and Phytochemical Studies
Joseph Jangu Magadula & Zakaria Heriel Mbwambo
Open Science
Ethnobotanical, Pharmacological and
Phytochemical Studies
Joseph J. Magadula
Zakaria H. Mbwambo
First published 2014
by Open Science Publishers
228 Park Ave., S#45956, New York, NY 10003, U.S.A.
ISBN: 978-1-941926-10-9
Copyright © 2014 Joseph J. Magadula
Copyright © 2014 Zakaria H. Mbwambo
All rights reserved. No part of this book may be reprinted or reproduced
or utilized in any form or by any electronic, mechanical, or other means,
now known or hereafter invented, including photocopying and
recording, or in any information storage or retrieval system, without
permission in writing from the publishers.
Cover design: Anne Harris, Syracuse
Layout: Carrie Lee, Buffalo
Printed in the United States of America.
First Edition
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registered trademarks, and are used only for identification and
explanation without intent to infringe.
A PDF version of this book is available for free in Open Science at
www.openscienceonline.com. This work is licensed under the Creative
Commons Attribution-NonCommercial 3.0 Unported License. To view a
copy of this license, visit http://creativecommons.org/licenses/by-nc/3.0/
This book is dedicated to
the late Professor Zakaria H. Mbwambo who
passed away
on 19th July 2014 while it was at its
publishing/printing stage
Contents
Foreword.......................................................................................................... 7
Preamble (About This Book) ........................................................................... 9
Acknowledgements ....................................................................................... 11
General Introduction ...................................................................................... 13
Chapter 1
1.1
Tanzanian Garcinia Species................................................... 17
Introduction .......................................................................................... 18
1.2 Tanzanian Floristic Regions ................................................................. 18
1.3
Distributions of Garcinia Plant Species in Tanzania ........................... 20
1.4
Basic Features of Selected Garcinia Plant Species .............................. 23
1.4.1 Garcinia acutifolia N. Robson .................................................. 24
1.4.2 Garcinia bifasculata N. Robson ................................................ 25
1.4.3 Garcinia buchananii Bak .......................................................... 26
1.4.4 Garcinia edulis Exell ................................................................. 27
1.4.5 Garcinia ferrea Pierre ............................................................... 28
1.4.6 Garcinia huillensis Welw. ex Oliv ............................................ 28
1.4.7 Garcinia indica DC ................................................................... 29
1.4.8 Garcinia kingaensis Engl .......................................................... 30
1.4.9 Garcinia livingstoneii T. Anders ............................................... 31
1.4.10 Garcinia mangostana L. .......................................................... 32
1.4.11 Garcinia pachyclada N. Robson ............................................. 33
1.4.12 Garcinia semseii Verdc ........................................................... 34
1.4.13 Garcinia smeathmannii (Planch. & Triana) Oliv. ................... 35
1.4.14 Garcinia volkensii Engl ........................................................... 35
1.4.15 Garcinia xanthochymus Hook. F. ............................................ 36
Chapter 2 Ethnobotany of African Garcinia Plants .............................. 39
2.1
Introduction .......................................................................................... 40
2.2. Ethnopharmacology of African Garcinia Plants ................................. 40
6
Contents
Chapter 3 Pharmacological Activities of African Garcinia Plants ....... 45
3.1
Introduction .......................................................................................... 46
3.2
Antimicrobial Activity.......................................................................... 47
3.3
Antimalarial Activity ............................................................................ 60
3.4
Anticancer Activity .............................................................................. 61
3.5
Antioxidant Activity ............................................................................. 64
3.6
Antiviral Activity.................................................................................. 68
3.6
Other Biological Activities ................................................................... 70
Chapter 4 Phytochemistry of African Garcinia Plants ......................... 75
4.1
Introduction .......................................................................................... 76
4.2
Benzophenones ..................................................................................... 85
4.2
Flavonoids ............................................................................................ 86
4.3 Triterpenoids......................................................................................... 87
4.4 Xanthones ............................................................................................. 88
4.5
Other Compounds ................................................................................. 89
References .................................................................................................... 97
Appendix List of African Garcinia Species-Countrywise ................... 109
Foreword
The search for plants that heal still represents a fascinating task. Before the
Synthetic Era, almost all medicines were obtained from plant tissues and organs:
roots, barks, stems, leaves, flowers and fruits. Self-medication was also
observed in non-human primates to control parasitic infections and provide
relief from gastrointestinal upsets. Therefore, in these terms, it seems that
medicinal plant-animal coevolution is more ancient than the medicinal
plant-human one, and that self-medicative behavior of non-human primates
represented the evolutionary force for human traditional herbal medicine. The
history of pharmacognosy is full of famous examples: the antimalarial alkaloid
quinine from Cinchona tree, cardiac glycosides from Digitalis spp., curare from
Chondrodendron tomentosum, the antipsychotic indole alkaloid reserpine from
Rauwolfia serpentina and, among anticancer drugs, taxol from Taxus brevifolia,
vincristine and vinblastine from Catharanthus roseus and camptothecin for
Camptotheca acuminata. Garcinia species enrich this plentiful scenario, by
virtue of their bio- and chemodiversity and healthy properties. In this book, the
authors provide a comprehensive and updated survey on African Garcinia
plants, with emphasis on eastern Africa species, focusing on botanical,
ethnobotanical, ethnopharmacological and phytochemical aspects. The authors
are very expert in the field of Garcinia research, as shown by their relevant
publications on these topics.
Professor, Marcello Iriti, 2014
Editor-in-Chief
European Journal of Medicinal Plants
Preamble (About This Book)
This book has been written as a way of documenting the research results done
by the authors and other researchers over years on the African Garcinia plants.
Generally, the book is based on the area of academic training of the authors,
which is the organic chemistry and in particular, the Chemistry of Natural
Products.
This book has been arranged in four chapters. The first chapter gives an
overview of the Garcinia plant species growing in Tanzania, a country of
domicile of the authors of this book. Furthermore, the localities in Tanzania
where the plants are collected are included together with the basic features of
some Garcinia plants growing in Tanzania.
Chapter two is devoted to the ethnobotanical information on the genus
Garcinia whereby general botanical description of a Garcinia plant is given. In
addition, the traditional uses (ethnopharmacological information) of Garcinia
plants growing in Africa are included in a tabular form.
Chapter three is committed to the pharmacological activities of African
Garcinia plants. This includes the biological activities on various crude extracts
and compounds from African Garcinia plants, including antibacterial,
antimalarial, cytotoxic, antioxidant, antifungal and antiviral activities. The table
included in this chapter contains biological activities of extracts from 13
African Garcinia plant species tested either in vitro or in vivo for various
microorganisms. Furthermore, the structures (1-40) of some biologically active
compounds are presented.
Chapter four deals with the phytochemistry of African Garcinia plants, from
which over 100 natural product compounds have been isolated. The major
10
Preamble (About This Book)
classes of compounds reported being benzophenones, flavonoids, triterpenoids
and xanthones. In this chapter, it has been revealed that G. kola which is
reported to grow in many West and Central African countries is the most
studied plant among the African Garcinia species both pharmacologically and
phytochemically points of view.
It is our trust that, this book will provide potential and useful reference
materials for the natural products researchers. It will also offer useful academic
and
technical
information
to
ethnobotanists,
ethnopharmacologists,
pharmacologists, phytochemists and foresters in Africa and all over the global.
We hope that you will enjoy reading this book.
&
Joseph Jangu Magadula
[Dip Ed, BSc Ed (Hons), MSc (chem.), PhD]
Zakaria Heriel Mbwambo
[MSc Pharm, PhD]
Dar es Salaam, 2014
Acknowledgements
It is believed that a scientific worker can’t produce a document in the absence
of professional and social interaction with other people. The academic and
research knowledge and ability invested in the authors of this book are the result
of contribution and nurturing of many people. So, it was thought to be wise and
sensible idea to mention few of them, among the many.
First of all we would like to thank God, for keeping us strong. He is
constantly embracing us and took us through even during difficult moments. He
is always our Rock and Savior.
We wish to acknowledge the contribution made by our former mentors whose
inspirations and guidance were the key for us to pursue the academic career in
the field of organic chemistry and later specialize in Natural Products Chemistry.
In this regard, we would like to mention and thank Professors Mayunga H. H.
Nkunya, Dulcie A. Mulholland, Neil Crouch, A. Douglas Kinghorn and Dr
Cosam J. Chiwanga who guided us during different stages of our academic and
research careers.
We wish also to acknowledge the contribution made by our research
collaborators from different parts of the world. To mention the few, Professors
Berhanu Abegaz (then in Botswana, now in Nairobi-Kenya), Supinya Tewtrakul
(Thailand), K. H. Lee (USA), Pascal Richomme (France), Luc Pieters
(Belgium), Pher Andersson (Sweden), Robinson Mdegela (Tanzania) and Drs
Rebecca Goss (UK) and Matthias Heydenreich (Germany).
A special thanks to our families for tolerating our absence when performing
our research and academic duties and particularly during the time of producing
this book.
12
Acknowledgements
Finally, we would like to acknowledge the financial support from
International Foundation for Sciences (IFS) for sponsoring the initial study of
the genus Garcinia for plants available in Tanzania through grant # F/4572-1,
the seed money from Swedish International Development Agency-Muhimbili
University of Health and Allied Sciences (Sida-MUHAS) through the
Directorate of Research and Publications. Commission for Science and
Technology (COSTECH) for financial support on the ethnobotanical study,
bioassays and herbal formulation of products from Tanzanian Garcinia plants
through grant # RG47/09.
General Introduction
The genus Garcinia belongs to the family Clusiaceae, subfamily Clusioideae
and the tribe Garcinieae. The name Garcinia honors a French botanist, Laurent
Garcin (1683-1751) who lived and worked in India, where the genus is highly
varied (Glen, 2004). This genus is considered to have over 450 plant species
worldwide out of which about 300 species are found to the tropical Africa,
Madagascar, tropical Asia, NE Australia, Polynesia, tropical America and China
(Perry and Metzger, 1980).
Here underneath is the taxonomic hierarchy of the genus Garcinia:
KINGDOM
Plantae
DIVISION
Magnoliophyta
CLASS
Eudicotyledoneae
ORDER
Malpighiales
FAMILY
Clusiaceae
TRIBE
Garcinieae
GENUS
SPECIES
Garcinia
(Ca 600 species worldwide)
Currently, it is not well documented on the exact number of Garcinia species
available in Africa, only scattered reports can be cited. For instances, in
Madagascar and the Comoros alone there are about 32 Garcinia species
reported to grow in the rain forests, with almost all of them being endemic to
this country (Sweeney and Rogers, 2008) while in Tanzania only 15 Garcinia
species are reported, most of them being scattered along the Eastern Arc
Mountains (Magadula and Tewtrakul, 2010). In West Africa, about 50 Garcinia
14
General Introduction
species are reported to grow, with 20 of them been reported from Cameroon
(Agyili et al., 2007) and the rest distributed in other West African countries. In
South Africa, only two (2) Garcinia species namely G. gerrardii and G.
livingstoneii (African mangosteen) are reported to be indigenous and they are
famous in traditional medicine (Palgrave et al., 2002). The distribution of
Garcinia plant species in Africa indicated the plants to grow and being reported
phytochemicaly and pharmacologicaly from only 20 African countries mainly
in the south of Sahara region (Fig. 1).
KEY:
No any report
Available report on Garcinia Species
Fig. 1. Distribution map of African Garcinia plants showing countries
reported to have Garcinia species.
In total, about 80 Garcinia species are reported to grow in Africa. However,
only 21 Garcinia species have been investigated phytochemicaly and/or
pharmacologicaly. Currently, more than 130 compounds have been identified in
Garcinia plants, of these 39% are xanthones, 27% are flavonoids, 10% are
triterpenoids, 8% are benzophenones and 16% are other classes of compounds,
with some of them being isolated from Garcinia plants for the first time. The
General Introduction
15
phytochemical reports included in this book indicate that only a small fraction
of African Garcinia plants have been studied for their chemical constituents.
This necessitates further work to be done on an uninvestigated species.
Due to the importance of Garcinia plants in terms of medicine, food and in
plant species distribution and biodiversity, this report therefore intends to put
together a record of what is known about the genus Garcinia in Africa. If not
assembled and documented, such information, which is usually scattered in
various literatures, herbaria records and other unpublished sources, will not be
easily accessible to give comprehensive picture of the value of the African
Garcinia species. It is anticipated that compilation of the information will also
provide new direction in conservation and sustainable management of these
important medicinal plants.
Despite recent progress in phytochemical and pharmacological studies from
the African Garcinia species, significant gaps still exist concerning both safety
and toxicity aspects of some extracts and pure compounds. Further
investigations have to be done including clinical studies, more phytochemical
discoveries and subsequent screening tests aiming at opening new opportunities
to develop drugs from Garcinia constituents. This book, therefore, provides
useful clues to promote further investigations for the development of new
phytopharmaceuticals or lead compounds from the genus
Garcinia.
Furthermore, this book will give basic information on sustainable exploitation
and possible conservation strategies for African Garcinia plants.
Tanzanian Garcinia
Species
18
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
1.1 Introduction
Tanzania, like many other African countries, is endowed with tropical forests
that are rich in natural resources, particularly plants. The country is divided into
six major ecological zones, namely Lake Victoria Mosaic, Coastal Forest and
Thickets, Afromontane Forest, Acacia-Savanna and Grasslands, Acacia Commiphora Thornbush and Miombo forests/woodlands, while the floristic
regions are known to be eight, T1-T8. Every zone/region has its characteristic
flora/plants and some uniqueness in terms of medicinal value of plants (Stuart et
al., 1990). Our ethnobotanical survey and the literature report revealed that
Garcinia plants grows at least in almost all ecological and floristic zones except
T2, where there is no any Garcinia plant species being reported (Bampss et al.,
1978).
1.2 Tanzanian Floristic Regions
Tanzanian flora is within the Tropical East African Flora which comprises of
about 21,650 vascular plant species. Tanzania alone has over 10,650 higher plant
species, out of which about 2,500 species are indigenous whereas more than 1200
plant species are endemic. Currently, Tanzania has eight (8) floristic ecozones,
T1-8 (Fig. 2), each zone being characterised by unique features of plant diversity,
including the richest Eastern Arc Mountains as one of the biodiversity hot spots of
Tanzania. It spreads and covers all parts of T3 and T6 floristic regions and is
reported to contain about 2000 plant species with 25 – 30% being endemic to the
forests and forest edges of the mountains (Burgess et al., 2002).
Tanzanian Garcinia Species
19
Fig. 2. Tanzanian Floristic Regions.
Each floristic zone covers a certain number of political regions in Tanzania as
indicated in Table 1 below.
Table 1. Floristic zones and their corresponding political regions in Tanzania.
Zone
Regions
T1
Geita, Mwanza, Kagera, Mara, Simiyu and Shinyanga
T2
Arusha, Manyara
T3
Kilimanjaro, Tanga
T4
Kigoma, Rukwa, Tabora
T5
Dodoma, Singida
T6
Coastal, Dar es Salaam, Morogoro
T7
Iringa, Mbeya
T8
Lindi, Mtwara, Ruvuma
P
Pemba
Z
Zanzibar
20
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
1.3 Distributions of Garcinia Plant Species in Tanzania
The distribution of the Garcinia plants in Tanzania indicated these plants to
grow in almost all eight (8) floristic zones. A total of 15 Garcinia plant species
are known from different habitats ranging from the altitude of 400 to 2300 m
high. Different studies have been done to establish potential biodiversity of
Tanzanian forest potentials. A study to determine richness of vascular endemic
plants of the Uluguru Mountains, in Morogoro region (T6), identified about 108
plant species to be endemic to the Uluguru Mountains. From this study, only
one Garcinia species, namely G. bifasculata, was reported to be endemic to the
Kimboza Forest Reserve (Temu and Andrew, 2008). In another study on the
East and West Usambara mountains (T3), about 150 vascular plant species were
reported to be endemic (Polhill, 1968) from which two Garcinia species,
namely G. volkensii and G. buchanannii, are indigenous and four Garcinia
species namely G. edulis, G. ferrea, G. mangostana and G. xanthochymus, are
exotic (Bamps et al., 1978). In Zanzibar, only three Garcinia species have been
cultivated including G. mangostana (at Kibweni and Kizimbani areas), G.
xanthochymus (at Zanzibar fide) and G. indica (at Migombani and Mtoni areas).
The complete list of Tanzanian Garcinia species include G. acutifolia N.
Robson, G. bifasculata N. Robson, G. buchananii Bak., G. edulis Exell, G.
ferrea Pierre, G. huillensis Welw. ex Oliv., G. indica DC., G. kingaensis Engl.,
G. livingstonei T. Anderson, G. mangostana L., G. pachyclada N. Robison, G.
smeathmannii (Planch&Triana) Oliv., G. semseii Verdc, G. volkensis Engl. and
G. xanthochymus (Roxb. T. Anders), (Table 2).
Tanzanian Garcinia Species
21
Table 2. Garcinia plant species found in Tanzania.
Name
Status
Habit
Indigenous
Shrub, 2-3 Dry evergreen
m
forest, 100 m
1
G. acutifolia
2
G.
Endemic
bifasciculata
3
G.
buchananii
Indigenous
Habitat
Swamp forest
Shrub, 4-6 (area of
m
limestone soil),
400 m
Evergreen
Tree/shrub,
riverine forest,
2-15 m
60-1800 m
Distribution
Region
Pugu Forest
Reserve
Litipo Forest
Reserve
T6, Coastal
T8, Lindi
Kimboza Forest
Reserve
T6,
Morogoro
Amani Nature
Reserve
T3, Tanga
Karagwe
Ukerewe
500-800 m
4
G. edulis
Exotic
5
G. ferrea
Exotic
6
G. huillensis
Indigenous
7
G. indica
Exotic
8
G. kingaensis Indigenous
9
G.
livingstoneii
Indigenous
Shrub, 2-8 Deciduous
m
woodland,
T1,
Bukoba
T1,
Mwanza
Mahali Mts,
Kassangazi
river-Mpanda
T4, Rukwa
Karagwe
T1, Kagera
Rondo plateau,
Mchinjiri
Kanga Forest
Reserve
Amani Nature
Reserve
Amani Nature
Reserve
T8, Lindi
T6,
Morogoro
T3, Tanga
T3, Tanga
Lugoda village
T7, Iringa
Zanzibar (at
Migombani and
Mtoni)
Zanzibar
Tree, 3-15 Evergreen forest,
Lugoda village
m
1200-2300 m
Fonera Forest
Reserve
Kanga Forest
Reserve
Madenge Forest
hill
Woodland,
Shrub or
thicket and
Pugu Forest
small tree,
grassland,
Reserve
3-18 m
0-1650 m
T7, Iringa
T7, Mbeya
T6,
Morogoro
T7, Iringa
T6, Coastal
22
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Name
Status
Habit
Habitat
Distribution
Region
Kazimuzumbi
village
Chalinze village
300-400 m
10
G.
mangostana
Exotic
G.
11
pachyclada
Indigenous
12 G. semseii
Endemic
13
G.
Indigenous
smeathmannii
Woodland and
Shrub, 2-5 shrubby
m
grassland,
0-1500 m
Tree, 3-15 Rain forest,
m
210-1800 m
Tree
Riverine forest,
1000-1600 m
Kimboza Forest
Reserve
Amani Nature
Reserve
Zanzibar (at
Kibweni)
T6,
Morogoro
T3, Tanga
Zanzibar
Ufipa district,
Kasanga village,
near Ngolotwa
T4, Rukwa
Kimboza Forest
Reserve
T6,
Morogoro
Kihansi
T7, Iringa
Manyangu
T6,
forest-Nguru MTS Morogoro
T4,
Mukugwa-Kibondo
Kigoma
Mwalesi-Rungwe
T7, Mbeya
Lupembe-Njombe T7, Iringa
14 G. volkensii
15
Indigenous
G.
Exotic
xanthochymus
Much-bran
Evergreen forest, Amani Nature
ched tree,
960-2400 m
Reserve
2-20 m
Ikwamba Forest
1520-1980 m
reserve
Kanga Forest
1300-2000 m
Reserve
Mamboto Forest
1600-1760 m
Reserve
Uluguru South
Forest
Shagayu forest,
Lushoto
T3, Tanga
T6,
Morogoro
T6,
Morogoro
T6,
Morogoro
T6,
Morogoro
T3, Tanga
Barankata area,
Moshi
T3,
Kilimanjar
o
Amani Nature
Reserve
T3, Tanga
Zanzibar
Zanzibar
Tanzanian Garcinia Species
23
1.4 Basic Features of Selected Garcinia Plant Species
Plants from the genus Garcinia are usually evergreen trees or shrubs and
dioecious and most of them grow in lowland rainforests or along riverines (Peres
and Nagem, 1997). Most notably, they are trees or shrubs, secreting yellow latex
when cut (Fig. 3) and generally glabrous. Leaves opposite or whorled, with latex
canals; petiole bases usually strongly excavated. Inflorescences in axillary
fascicles, rarely branched, or flowers solitary, axillary or terminal. Flowers
bisexual and/or unisexual (plants usually dioecious or polygamous). Sepals 2-4(5),
mostly imbricate; petals 2-4(-6), white, yellow, or red, decussate or imbricate, the
pairs often of different sizes. Stamens free, variously fasciculate, or connate into a
central mass, numerous in staminate flowers, fewer in bisexual flowers; anthers
short. Ovary 2-12-locular, often absent from staminate flowers; ovule 1 per locule;
styles short or lacking; stigmas expanded. Fruit a berry, mostly 1-locular, smooth
to verrucose, leathery, ellipsoid to globose or ovoid, the mesocarp often juicy and
sweet. Seeds 1-4; cotyledons minute.
(http://www.mobot.org/MOBOT/research/ven-guayana/clusiaceae/page6.shtml)
a
b
Fig. 3. (a) Stem bark of G. semseii showing yellow exudates and
(b) G. semseii showing some leaves.
24
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Fruits have been observed to have one to four seeds with fleshy, smooth or
verrucose glabrous or puberulous berry (Bamps et al, 1978). Fruits of many
Garcinia species are edible, particularly those of an African mangosteen (Figure
4) and are highly eaten by wild animals as well as by humans.
Fig. 4. Fruits of G. livingstoneii.
A survey conducted to locate the Tanzanian Garcinia species indicated that
some of them are threatened for extinction due to habitat destruction. A good
example is G. acutifolia formerly reported to grow in Pugu Forest, Coastal
region, which was currently wiped out from this area (Bamps et al., 1978). This
survey, therefore, was able to locate and identify 15 Garcinia species growing
in Tanzania as described in the following sub-sections.
1.4.1 Garcinia acutifolia N. Robson
The botanical description of G. acutifolia indicate that the plant is a shrub or
small tree, 2-3 m. high, glabrous; branches slender, narrowly 4-winged. Leaves
are opposite, petiolate; lamina, chartaceous, bright green, concolorous, ovate to
lanceolate or elliptic, shortly and usually very acutely acuminate at the apex.
Tanzanian Garcinia Species
25
Male flowers with 2 antisepalous stamen-fascicles, each of 3 stamens, with
filaments completely united and anthers sessile, oblong or elliptic, curved or
straight, not septate.
Fig. 5. Aerial parts of G. acutifolia at Litipo Forest Reserve, Lindi, Tanzania.
This plant is mostly found among dry coastal forest species reported to grow
in Mozambique and Tanzania and it is threatened by habitat loss. (Lovett and
Clarke, 1998). In Mozambique, it grows between Muaguide and the
Quissanga-Macomia crossroads, 2·3 km from Muaguide. In Tanzania, it is
reported to grow in Pugu Forest Reserve, Coastal region at Kazimzumbwi area
as well as at Litipo forest in Lindi region.
1.4.2 Garcinia bifasculata N. Robson
This plant is reported to grow at Kimboza Forest Reserve; it is a tree found to
grow at an altitude of 390 m along the swamp forest on limestone outcrops. The
voucher specimen as well as the photo was taken at the site. Neither flowers nor
fruits were observed during the time of visit to the Kimboza forest reserve.
26
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Fig. 6. Aerial parts of G. bifasculata at Kimboza Forest Reserve, Morogoro, Tanzania.
1.4.3 Garcinia buchananii Bak
It is a small evergreen tree with leaves being oblong or elliptic. The leaves
and bark exude yellow sticky latex when cut. Lateral veins are evidently fixed
on both surfaces. Flowers are greenish-yellow and observed in solitary or in
small clusters. The fruits are edible as they are fleshy, spherical and yellow
when ripe.
Fig. 7. Aerial parts and fruit of G. buchanannii.
Tanzanian Garcinia Species
27
This plant is widely distributed, ranging from Sudan southwards through
Eastern Africa to Angola, Mozambique and Zimbabwe. In Tanzania, this plant
is reported from Amani Nature Reserve, Ukerewe, Kanga Forest Reserve
(Morogoro), Gombe Forest Reserve (at Kakombe valley-Kigoma), Mwihana
Forest Reserve (West Udzungwa-Iringa) and in Karagwe (Kagera region).
1.4.4 Garcinia edulis Exell
This is a small tree, 5-6 m tall, with a straight and dark brown trunk,
producing yellow latex when cut. Leaves are opposite, stiff, 7-12 cm long and
3-5 cm wide. Flowers are whitish and small, produced in axillary groups of 1-15
at branch nodes (Fig. 8). Fruits are round, about 3 cm in diameter, with a thin
orange to reddish peel with an aromatic sweet sour taste. Seeds are in 1 or 2. It
is commonly known as ‘the lemon drop mangosteen’. The plant is propagated
by seeds that germinate easily with flowering and fruiting takes about 3 years.
Fig. 8. Aerial parts and flowers of G. edulis at Amani Nature Reserve, Muheza,
Tanzania.
The plant is very attractive; sometimes it is used as an ornamental tree. The
earlier classification of this plant placed it in the genus Rhedia and hence it was
28
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
called Rhedia edulis. In Tanzania, it is cultivated at Amani Nature Reserve near
Sigi River, in Muheza district, Tanga region.
1.4.5 Garcinia ferrea Pierre
The common name for G. ferrea is Pursat mangosteen with a synonym to
Garcinia benthamii Pierre. This plant grows up to 5-6 m high and in Tanzania is
known to grow at Amani nature reserve, Muheza district, Tanga region.
Fig. 9. Aerial parts and fruits of G. ferrea at Amani Nature Reserve, Muheza,
Tanzania.
1.4.6 Garcinia huillensis Welw. ex Oliv
The reported common names for this plant are Granite garcinia (English),
Granite mangosteen (English) and Mutunduru (Shona) (Drummond, 1981). It is
a small evergreen tree growing up to 4-5 m high. The leaves are oblong or
elliptic, thick and leathery, exuding yellow sticky latex when broken. The veins
are lateral and conspicuously etched on both surfaces. Flowers are solitary or in
small clusters, axillary, greenish-yellow and short-lived with the flowering time
Tanzanian Garcinia Species
29
being September to November. Fruits are always fleshy, spherical, yellow when
ripe and are edible.
Fig. 10. Aerial parts of G. huillensis at Igomaa village, Mufindi, Tanzania.
The habitat of this plant is on granite kopjes, rocky outcrops and in riverine
fringes with an altitude of about 900-1800 m. Its distribution ranges from Sudan
southwards through eastern Africa to Angola, Mozambique and Zimbabwe
(Smith & Allen, 2004). In Tanzania, G. huillensis is reported to grow from
Lugoda (Iringa), Geita (24 km South of Geita Gold Mines) and Gombe Forest
Reserve along Kakombe valley in Kigoma region.
1.4.7 Garcinia indica DC
This plant is commonly known as ‘kokum’ in most parts of India. It is a tree
with a dense canopy of green leaves being indigenous to India. Leaves are
elliptic, oblong or oblong-lanceolate about 6-8 cm long and 3-4 cm broad. The
flowers are fleshy, dark pink, solitary or in spreading cluster and the flowering
period is November to February. The fruit is brownish or brownish-gray,
marbled with yellow, and is crowned by the 4-parted, stalkless stigma. There
are from 6 to 8 seeds, and the pulp is juicy, white, and delicious in taste and
odor. The fruiting season is between April and May.
30
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Fig. 11. Aerial parts and Fruits of G. indica.
The habitat of G. indica is always forest lands, riversides and wastelands. The
plant prefers evergreen forests, but sometimes they also thrive in areas with
relatively low rainfall. In Tanzania, it is repoted to grow in Zanzibar at
Migombani and Mtoni areas.
1.4.8 Garcinia kingaensis Engl
This plant is always found in the understorey of evergreen forest and forested
ravines at an altitude range of 1350-2100 m. It is a small to medium-sized tree
with main branches, it appears horizontal while the lateral branches are grooved
and angular. When cut it gives yellow sap. Leaves are opposite, narrowly
elliptic to oblong and they are dull bluish to grey-green. Flowers are in clusters
on short spur-branchlets along the stems. Fruits are spherical and yellow to
orange and they are edible. The flowering time is between September and
October.
Tanzanian Garcinia Species
31
Fig. 12. G. kingaensis showing flowers, at Lugoda village, Mufindi, Tanzania.
In Tanzania, it is reported to grow at Lugoda (Iringa), Songea (Luwiru-Kiteza
Forest Reserve), Fonera Forest Reserve (Mbeya), Kanga Forest Reserve
(Morogoro-Turiani), Madenge Forest (Iringa) and Mwanihana Forest Reserve
(West Udzungwa mountains-Iringa. The wood is hard and used for firewood,
poles, tool handles, spoons, stools and milk pots while the sap gives yellow dye.
As known for other Garcinia plants, fruits are edible.
1.4.9 Garcinia livingstoneii T. Anders
It is an evergreen, small tree of up to 20 m high usually with dense rounded
crown. Leaves are always in whorls of three, while flowers are in crowned
fascicles of 5-15 and they attract insects due to their sweet nectar. Fruits are
yellow or orange in colour while their shapes are always ovoid and they are
edible.
32
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Fig. 13. Branchlets and Fruits of African Mangosteen at Kazimzumbwi, Kisarawe,
Tanzania.
It grows in a wide range of tropical Africa from from Côte d'Ivoire east to
Somalia, and south to South Africa being commonly known as African
mangosteen to its esteemed fruits. The distribution of the plant in Tanzania is
high as it is reported to grow in Chalinze area, Pugu Forest Reserve and
kisarawe at Kazimzumbwi village and it is called Mutumbi or Mpekechu (in
Swahili).
1.4.10 Garcinia mangostana L.
It is a small tree of 7-8 m high with dense heavy branched crown. The leaves
are leathery. The petioles are short and thick. The flowers are 5 centimeters in
diameter, 4-parted, bisexual, and borne singly or in pairs at the ends of the
branchlets. The seeds are large, flattened- and embedded in snowy-white or
pinkish delicious pulp. The mangosteen fruit is the size of a small apple, purple
colored, with a hard rind. Inside there are typically five to seven seeds
surrounded by a sweet, juicy cover (or aril). Dried fruits are well known for
their medicinal uses.
Tanzanian Garcinia Species
33
Fig. 14. Aerial parts and fruits of G. mangostana at Amani Nature Reserve, Tanzania.
Although this plant is known to be native to South East Asia, it is cultivated
in almost all tropical countries. It is a true mangosteen due to its valuable fruits.
In Tanzania, G. mangostana is cultivated at Amani Nature Reserve, Muheza
district, Tanga region.
1.4.11 Garcinia pachyclada N. Robson
This appears as a shrub or small tree of about 5 metres high having thick
branches with a grayish or corky bark. The bark secrets yellow and sticky latex
when cut. Leaves are observed to be in whorls of three. Flowers are observed to
be unisexual and clustered in axils or above the leaf-scars on mostly leafleded
branches.
G. pachyclada differs from G. livingstonei by its Uapaca-like habit
(ascending branches), its thicker rough branches; its leaves are thickened,
undulate margins, and its large flowers on short pedicels. It is a plant of plateau
34
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
woodland rather than riverine forest. In Tanzania, this plant is reported to grow
in Sumbawanga (Rukwa) at Kasanga area-Ngolotwa.
1.4.12 Garcinia semseii Verdc
This is a tree that grows to the height of about 15 mters, having slightly
wrinkled branchlets and rough nodes. The leaves are opposite and they become
reddish brown when dry. The plant always contains two flowers at the leafless
nodes. Fruits are roughly warted and highly eated by monkeys.
Fig. 15. Leaves and Fruits of G. semseii taken at Kimboza Forest Reserve, Morogoro
district.
This plant is endemic to Tanzania and its range description indicates to be
known only from four localities including Kimboza forest reserve, Chita and
Kihansi within the Udzungwa mountains and at Nguru mountain in Morogoro
region.
Tanzanian Garcinia Species
35
1.4.13 Garcinia smeathmannii (Planch. & Triana) Oliv.
It is a small tree that grows to about 20 m high and haaving a bole of over 1
m in girth. It has a dark orangeish scaly bark exuding some yellow latex when
cut. Leaves are simple and opposite while petioles are short or normal and entire
margin. Flowers are dioecious and in fascicles of 5–30 in the axils of leaves.
Fruits are purplish-green turning to yellow with 1-2·5 cm in diameter.
Fig. 16. Leaves and Flowers of G. smeathmannii.
The plant always grows in riverines and uplands to about 1500 m elevation.
The distribution ranges from Angola, Congo, Gabon, Cameroon, Central
African Republic and DR Congo. In Tanzania, it is reported from 48 km South
of Kibondo at Mukugwe River, Rungwe at Mwalesi River, Njombe (upper
Ruhudje river and Lupembe area-north of the river).
1.4.14 Garcinia volkensii Engl
This is a highly branched plant growing to about 20 m high. Its bark is grey
or brown and gives white/yellow exudates when cut. Leaves are simple,
opposite or whorled while petioles are angled and/or narrowly winged. Flowers
36
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
are dioecious cream/green-white/pink and infloresence in axillary cymes. Fruits
are green and turning yellow/orange/brown when ripe.
Fig. 17. Aerial parts of G. volkensii at Shagayu Forest Reserve, Lushoto, Tanzania.
The ecology of this plant is in understorey of evergreen rainforest as well as
dry evergreen forest to an elevation of up to 2400 m. Its distribuition in
Tanzania is from Ikwamba Forest Reserve, Kanga Forest Reserve, Mamboto
Forest Reserve (all from Morogoro region), Amani Nature Reserve, Shagayu
Forest Reserve (from Tanga region), Useri at Barankata area (Kilimanjaro
region) and Mwanihana Forest Reserve (West Udzungwa-Iringa).
1.4.15 Garcinia xanthochymus Hook. F.
It is a small evergreen tree growing up to about 15 m high with horizontal
branches and a dense pyramidal crown. Leaves are narrowly oblong while fruits
are pale orange to dark yellow with a diameter of about 9 cm. The fruit is edible
Tanzanian Garcinia Species
37
and has a pleasant acid taste. It usally contains two seeds, sometimes is called
yellow mangosteen or camboge. Flowering occurs between March and May.
Fig. 18. Aerial parts and fruits of G. xanthochymus at Amani Nature Reserve, Tanzania.
The tree is well adapted to shade and humid conditions. In Tanzania, the
plant was cultivated at Amani Nature Reserve, near Sigi river, Muheza district,
Tanga region.
Ethnobotany of African
Garcinia Plants
40
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
2.1 Introduction
Medicinal plants play an important role in the healthcare systems all over the
world.
Around 80% of general population in the world uses plants to treat several
illnesses (UICN, OMS, WWF, 1993). Ethnobotanical studies are very important
to reveal the past and present culture about plants. Human societies throughout
the world have accumulated a vast body of indigenous knowledge over
centuries on medicinal uses of plants, and for other related uses including
poison for fish and hunting, purifying water, and for controlling pests and
diseases of crops and livestock.
In this respect, people are able to use and conceptualize plants in their local
environments. For instance, medicinemen or herbalists have a good knowledge
on botanical description including correct identification of plants for intended
purposes. Hence, ethnobotany details the knowledge of plants by the local
people and their usefulness as understood by the people of a particular ethnic
group (Tor-Anyiin et al., 2003), particularly this study involves the scientific
study of the traditional knowledge and customs of a people concerning plants
and their medical, religious, and other uses.
2.2. Ethnopharmacology of African Garcinia Plants
Many African Garcinia species have been reported to be used in traditional
medicine for many centuries. Some of them have been studied and reported to
have many ethnomedical uses. Among the effects reported are the treatment of
head and abdomen pains, fever, ulcers, impotence, throat and bronchial
infections, venereal diseases, diarrhea, hepatitis, asthma rheumatism, arthritis,
Chapter 2 Ethnobotany of African Garcinia Plants
41
cancer, liver cirrhosis and cough (Table 3). Many literatures indicated Garcinia
kola, a plant reported to grow in many Western African countries, to be the
most studied Garcinia species in all aspects, including ethnomedical use,
pharmacology and its phytochemistry. Sometimes, it is referred to as a “wonder
plant” because every part of it has been found to be of medicinal importance
(Dalziel, 1937). Ethnomedically, many Garcinia plants are used as a decoction,
an infusion or as a juice. Most extracts are prepared with cold or hot water and
are applied for the treatment of toothache, inflammations, for wound-healing,
jaundice, ulcers, dysentery, as aphrodisiac, for fever, sleeping sickness, venereal
diseases, liver cirrhosis, arthritis and respiratory track diseases. Other Garcinia
plants are used as chewing sticks, fertilization stimulant, aid childbirth while
some fresh or dried fruits are used as food. For instance, G. livingstoneii is
commonly known as an ‘African mangosteen’ as it produces very tasty and
delicious fruits while the powdered root is used as an aphrodisiac (Anorld &
Gulumian, 1984). Hence, many Garcinia plants are known for different
traditional uses (Table 3) while others are not reported for any ethnomedical
use.
42
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Table 3. Traditional uses of some Garcinia plant species growing in Africa.
S/N
Scientific
name
Where
collected
Part used Traditional uses
1
G. afzelii
Ghana
Stem wood
Guinea
Root bark Cure aphrodisiac
G. buchananii
2
G. epunctata
3
G. huillensis
Vasileva (1969)
Diarrhoea, dysentery,
Stem bark abdominal
Balemba et al. (2010)
discomfort, pains
impotence, chewing Adu-Tutu et al.
Ghana
Stem wood
stick
(1979)
Watt and
South Africa Stem bark Aphrodisiac
Breyer-Brandwijk
(1962)
Tanzania
DR Congo
G. kola
Adu-Tutu et al.
(1979)
Tanzania
Tanzania
5
Impotence, chewing
stick
Reference
Nigeria
Root bark Used for insanity
Mathias (1982)
Stem bark Treat sleeping
+Root bark sickness
Cure venereal
diseases, sores,
Stem bark bronchitis, measles,
dermatitis and as
aphrodisiac
Used for fever,
inflammation, cough,
Stem bark anthelmintic and
respiratory track
diseases
Freiburghaus, et al.
(1996)
Bakana et al. (1987)
Gill and Akinwumi
(1986)
Dried Fruit Treat arthritis
Iwu & Anyanwu
(1982)
Fresh fruit Used as food
Ebana et al. (1991)
Used as an antiseptic
Dried
for cuts and sore
fruitpeel
throats
Used as a chewing
Dried root
stick,
Treat liver cirrhosis,
inflammation of the
respiratory tract,
coughs
Used for cough, tooth
decay, gonorrhea
(roots soaked in local
gin)
Used as fertilization
Seed
stimulant
Iwu et al. (1990)
Fadulu (1975)
Iwu et al. (1990)
Ebana (1991)
Elujoba (1995)
Chapter 2 Ethnobotany of African Garcinia Plants
S/N
Scientific
name
Where
collected
Part used Traditional uses
Used as a
masticatory, antidote
Dried seed
and inflammatory
disorders
Treat cough,
abdominal colic,
aphrodisiac and
catarrh
Treat diarrhoea,
hepatitis,
dysmenorrheal,
gastroenteritis and
asthma
Treat bronchitis,
diarrhoea, and throat
infections
6
G. livingstoneii Tanzania
Fruit
Venda (RSA) Leaf
G. lucida
Kenya
Root
Somalia
Root
Used as food
Used for toothache,
impotency and
aphrodisiac
Used to aid
Childbirth
Treat abdomen pains
Used as an
aphrodisiac
To treat gastric
infections, antidote
Stem
against poison,
aphrodisiac
properties
Treat stomach ulcers
Leaf
and liver diseases
Used for dressing
Sap (latex)
wounds
43
Reference
Iwu et al. (1990)
Akintonwa and Essien
(1990)
Braide (1989)
Adesina et al. (1995);
Orie and Ekon (1993),
Iwu 1993.
Johns et al. (1984)
Anorld and Gulumian
(1984)
Yu et al. (1982)
Samuelsson et al.
(1992)
South Africa Root
Palgrave et al. (2002)
Taanzania
Fotie at al. (2007)
7
G. mangostana. Madagascar
8
G. polyantha
Cameroon
9
G. punctata
Gabon
Stem bark Treat headache
10
G.
smeathmannii
Cameroon
Stem bark
Novy (1997)
Bouquet (1969)
Akendengue and
Louis (1994)
Antidote, chew-stick
Bouquet, 1969
and laxative
Ophtalmia (eye
Sap (latex)
Bouquet, 1969
treatments)
Bark latex Skin, mucosae
Bouquet, 1969
Pharmacological Activities
of African Garcinia
Plants
46
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
3.1 Introduction
Plants remain rich and potential source of therapeutic compounds for the
development of new drugs. Secondary metabolites obtained from plants have
been a great source of many drugs for managing various diseases. Even if recent
advances in biochemical engineering and other biotechnologies represent
alternative sources of drugs, more than 70 % of the current therapeutic drugs
derive
their
structures
from
plants
used
in
traditional
medicine
(Chantarasriwong, 2010). Although many and new drugs including antibiotics
have been developed in the last three decades, resistance to them by infectious
microorganisms has increased. As a result, the search for new bioactive
compounds from plants for pharmaceutical purposes has gradually increased
worldwide (Kaikabo et al., 2009). Many recent biological studies on medicinal
plants used as folklore remedies in the treatment of different ailments have
attracted the attention of a number of researchers as possible alternatives to the
existing incurable diseases and the problem of drug resistances. Globally, the
problems of multiple resistance as well as emergence of new and resurrection of
previously eradicated diseases have necessitated the continued effort to search
for novel and effective drugs from medicinal plants to complement the existing
synthetic drugs.
Recent studies have indicated that Garcinia species possess a wide range of
biological activities and led to a greater understanding of the pharmacology of
various species, particularly in relation to the antimicrobial, anticancer, antiviral,
antioxidant, antimalarial and other biological activities. These pharmacological
studies supports to the traditional uses of Garcinia plants in treating different
ailments by many African societies. Hence, reported pharmacological activities
on crude extracts and compounds from African Garcinia plants indicated
Chapter 3 Pharmacological Activities of African Garcinia Plants
47
various biological activities, including antibacterial (Ebana et al., 1991),
antimalarial (Tona et al., 1999), cytotoxic (Sordat-Diserens et al., 1992),
antioxidant (Farombi et al., 2002), antifungal (Kpakote et al., 1998) and
antiviral activities (Bakana et al., 1987; Gustafson et al., 1992; Magadula, 2010)
and other biological effects (Table 4).
3.2 Antimicrobial Activity
The treatment of infectious diseases has existed for many years and, as a
result, many reports of antimicrobial extracts and compounds from Garcinia
species have been documented from various parts of Africa. Over 20 different
crude extracts from more than 10 Garcinia plant species found in African flora
have been investigated for antimicrobial properties (Table 4).
One of the reports is on the ethanol extract of the dried stem bark of G. afzelii
collected in Togo. This extract showed significant antibacterial and antifungal
activities against Staphylococcus aureus and Asperigillus fumigatus (Kpakote et
al., 1998). In another study from a Congolese plant, G. huillensis, the in vitro
testing of the water extract of the stem bark indicated marked activity against
Cytospora species (Laine et al., 1985), while the antibacterial activity was noted
in the petroleum ether extract of this plant against Staphylococcus aureus with
the minimum inhibition (MIC) of 62.5 μg/ml (Bakana et al., 1987).
Garcinia kola, collected in Nigeria and Ghana is the most investigated
species with all parts studied pharmacologically. Thus, in the study of the ethyl
acetate extract of the dried seeds, good antibacterial and antifungal activities
were observed against Bacillus subtilis and Aspergillus niger both at a
concentration of 100 μg/ml (Madubunyi, 1995). Another study on the
methanolic extract of G. kola indicated significant in vitro antimicrobial
activities against some bacterial isolates comprising both Gram-positive and
48
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Gram-negative organisms tested at a concentration of 20 μg/ml. The zones of
inhibition exhibited by the extract against the tested organisms ranged between
10 and 23 mm, while the zones of inhibition exhibited by streptomycin and
tetracycline used as standard antibiotics ranged between 15 and 25 mm and, 12
and 25 mm, respectively (Adegboye et al., 2008). Significant antibacterial
activities were reported from the water and ethanol extracts of the root bark of
G. kola in a study conducted by Ebana et al. (1991). Furthermore, the study by
Iwu (1993) indicated the plant to have significant antimicrobial and
antiiflammatory activities. In the study by Akerele and co-workers on the the
crude ethanol extract, aqueous and chloroform fractions of the seeds of
Garcinia kola showed significant inhibitory activity against a range of clinical
isolates of both Gram positive and Gram negative bacteria. The MIC values
obtained ranged between 2.5 and 7.5 mg/ml for bacteria and fungi isolates,
respectively (Akerele et al., 2008).
Kpakote and co-workers investigated the dried stem barks of G. ovalifolia
and G. polyantha for antibacterial activities. Significant result was obtained
against Pseudomonas aeruginosa at a concentration of 4.0 mg /ml (Kpakote et
al., 1998, Table 4).
The acetone extract of G. livingstonei leaves was studied for antibacterial
activity using bioautography and by determining the minimum antibacterial
concentration against four nosocomial pathogens. Bioautograms showed that
two compounds were mainly responsible for the antibacterial activity namely,
amentoflavone (1) and 4''-methoxyamentoflavone (2) (Kaikabo et al., 2009).
The antibacterial activity of the isolated compounds was determined against
Escherichia
coli,
Staphylococcus
aureus,
Enterococcus
faecalis
and
Pseudomonas aeruginosa with both compounds exhibiting the MIC values
ranging from 8-100 μg/ml (Kaikabo et al., 2009). Further studies on the
Chapter 3 Pharmacological Activities of African Garcinia Plants
49
activities of compounds 1 and 2 were done against fast-growing non-pathogenic
Mycobacterium smegmatis. In this study, compound 1 was reported to be the
most active one with an MIC of 0.60 mg/ml, while the MIC of compound 2 and
the positive control isoniazid against M. smegmatis were similar at 1.40 and
1.30 mg/ml, respectively. This indicates that some infections caused by M.
smegmatis may be managed by these compounds (Kaikabo and Eloff, 2011).
On the other hand, Garcinia plants used ethnomedically as chewing sticks
have been investigated for their antimicrobial potential. Thus, from the
antibacterial fraction of the root bark of G. kola, biflavanone GB-1 (3) was
isolated as the major constituent. This compound showed significant
antibacterial activities against methicillin-resistant Staphylococcus aureus
(MRSA) and vancomycin-resistant enterococci (VRE) with MIC of 32 and 128
μg/ml respectively (Han et al., 2005).
Xanthones is an important class of compounds from Garcinia plants due to
its diverse biological activities. From the South African Garcinia plant, G.
gerradii, three prenylated xanthones, garcigerrin A (4), B (5) and
l2b-hydroxy-des-D-garcigerrin A (6) were tested for their activity against the
plant pathogenic fungus Cladosporium cucumerinum using a TLC biossay.
Garcigerrins were inactive at 50 μg/ml while compound 6 prevented growth of
the fungus at a concentration of 0.2 μg/ml (Sordat-Diserens et al., 1989). From
an African mangosteen, compounds 7-9 were tested for their activity against the
plant pathogenic fungus Cladosporium cucumerinum, using a TLC bioassay
with compounds 7 and 8 preventing the growth of the fungus at concentrations
of 0.5 and 0.2 μg/ml respectively (Sordat-Diserens et al., 1992). In another
study, smeathxanthone A (10) and smeathxanthone B (11) were isolated from a
Cameroonian plant, G. smeathmannii and tested for their in vitro antibacterial
50
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
and antiyeast activities. These compounds showed a mild activity against a
range of bacteria and yeasts (Komguem et al., 2005).
Momo and co-workers investigated the methanol crude extract from G.
lucida for its antimicrobial activity against Escherichia coli, Pseudomonas
aeruginosa, Salmonella typhi, Staphylococcus aureus, and Candida albicans.
The result of the crude extract indicated a good inhibitory activity with a MIC
value of 64 μg/ml on Candida albicans and it was inactive for other tested
organisms (Momo et al., 2011). The isolated compounds from the CH2Cl2
fraction of G. lucida were not active except cycloartenol (12) which exhibited
moderate and selective antimicrobial activity with IC50 of 512 μg/ml against E.
coli and P. aeruginosa (Momo et al., 2011).
Chapter 3 Pharmacological Activities of African Garcinia Plants
OH
OH
HO
51
HO
O
O
OH
OH
OH
OR
O
HO
O
HO
O
R
O
1 H
OH
OH
OH
OH
O
O
OH
2 CH3
O
OH
OH
O
OH
OH
OH
O
OH
OH
O
6
OH
O
O
O
OH
OH
O
8
OH
9
OH
OH
O
OH
O
O
O
7
OH
OH
OH
O
O
OH
O
5
4
OH
3
O
OH
O
O
OH
OH
OH
O
O
OH
10
11
12
Fig. 20. Structures of bioactive compounds isolated from some African Garcinia plants.
52
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Table 4. Biological activities of extracts from African Garcinia species.
Plant
species
(Country)
G. afzelii
(from
Togo)
Part used
Effects
(Extracting In vivo
(Organism tested)
solvent)
Antibacterial
Dried Stem
(Pseudomonas
(EtOH)
aeruginosa)
Antibacterial
Dried Stem
(Staphylococcus
(EtOH)
aureus)
Antifungal
Dried Stem
(Asperigillus
(EtOH)
fumigatus)
Antiyeast (Candida Dried Stem
albicans)
(EtOH)
G. edulis
(from
Tanzania)
Antiviral (HIV-1
protease)
Stem bark
(Ethanol)
Cytotoxicty
(Artemia salina)
Root bark
(Ethanol)
G. gerradii
Larvicidal (Aedes
(from South
aegypti)
Africa)
Dried Leaf
(CH2Cl2)
Anticrustacean
(Artemia salina)
Dried Leaf
(CH2Cl2)
Molluscicidal
(Biomphalaria
glabrata)
Dried Leaf
(CH2Cl2)
Antifungal
(Cladosporium
cucumerinum)
Dried Leaf
(CH2Cl2)
Cytotoxicty
(CA-COLON-SW
480)
Dried Leaf
(CH2Cl2)
Cytotoxicty
Dried Leaf
(CA-HUMAN-COL
(CH2Cl2)
ON-CO-115)
G.
huillensis
(from DR
Antifungal
(Cladosporium
cucumerinum)
Root bark
Antifungal
(Cytospora sp)
Dried stem
bark (H2O)
In vitro
Inactive- at a
conc of 4.0
mg /ml
Active- at a
conc of 4.0
mg /ml
Active- at a
conc of 4.0
mg /ml
Inactive- at a
conc of 4.0
mg /ml
Active with
IC50 value of
9.2 µg/ml
Active with
LC50 value of
2.36 µg/ml
Active- at a
conc of 500.0
mg /ml
Active- with
LC50 value of
53.0 µg /ml
Inactive- at a
concentration
of 400 ppm
Inactive- at a
concentration
of 100
µg/plate
Active- with
IC50 value of
<5.0 µg /ml
Weak activitywith IC50
value of 7.0
µg /ml
Active- at a
concentration
of 100
µg/plate
In an agar
plate, active at
a conc of 1-10
Reference
Kpakote et
al. (1998)
Kpakote et
al. (1998)
Kpakote et
al. (1998)
Kpakote et
al. (1998)
Magadula
(2010)
Magadula
(2010)
Cepleanu et
al. (1994)
Cepleanu et
al. (1994)
Cepleanu et
al. (1994)
Cepleanu et
al. (1994)
Cepleanu et
al. (1994)
Chapuis et
al. (1988)
Sordat-Dise
rens, et al.
(1989)
Laine et al.
(1985)
Chapter 3 Pharmacological Activities of African Garcinia Plants
Plant
Part used
Effects
(Extracting In vivo
species
(Organism tested)
(Country)
solvent)
Congo)
Antiviral
(Virus-Herpes
Simplex 1)
Dried stem
bark
(PetEther)
Dried stem
Antiviral
bark
(Virus-Coxsackie)
(PetEther)
Dried stem
Antiviral
bark
(Virus-Poliovirus 1)
(PetEther)
G.
huillensis
(from
Tanzania)
G.
kingaensis
(from
Tanzania)
G. kola
(from DR
Congo)
G. kola
(from
Nigeria)
In vitro
53
Reference
mg /ml
Inactive-the
conc was not
given
Inactive-the
conc was not
given
Inactive-the
conc was not
given
In an agar
plate, seen
active with
MIC value of
62.5 µg /ml
Bakana et
al. (1987)
Bakana et
al. (1987)
Bakana et
al. (1987)
Antibacterial
(Staphylococcus
aureus)
Dried stem
bark
(PetEther)
Antitrypanosomal
(Trypanosoma
brucei)
Dried stem
+ root
(CH2Cl2)
Active- with
IC50 value of
4.4 µg /ml
Freiburghau
s et al.
(1996)
Antiviral (HIV-1
protease)
Root bark
(Ethanol)
Active with
IC50 value of
15.2 µg/ml
Magadula
(2010)
CNS stimulant
Dried stem
bark (H2O)
Not active in rat
and the dose was
not stated
CNS depressant
Dried stem
bark (H2O)
Not active in rat,
the dose was not
stated
Antioxidant
Dried fruit
(H2O)
Bronchodilator
Fresh fruit
(Human adult, male) (H2O)
Active in rat liver
at a conc of 2.5
mg/ml
19 healthy
volunteers aged
17-25 years were
used for this
study. Decoction
was taken orally at
a dose of 15.0
gm/person. Weak
activity was
observed in 1 hour
after treatment
with results been
Bakana et
al. (1987)
Sandberg
and
Cronlund
(1977)
Sandberg
and
Cronlund
(1977)
Adegoke et
al. (1998)
Orie and
Ekon
(1993)
54
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Plant
Part used
Effects
(Extracting In vivo
species
In vitro
(Organism tested)
(Country)
solvent)
significant at p <
0.05 level
Active at a dose of
10 ml/kg. The rats
were given partial
hepatectomy and
Hepatoprotective
Saline Ext
enzyme
(glucose-6-phosph
atase) activity was
inhibited by 31%.
Protein & DNA
synthesis
Commercial inhibition at a
Hepatoprotective
sample of
dose of 5 ml/kg
kernel (H2O) Rats were given
partial
hepatectomy
Strong activity
Molluscicidal
at a conc of
(Biomphalaria
Dried leaf
100 ppm
pfeifferi, Lymnaea
(MeOH)
leading to
natalensis &
100%
Bulinus globosus)
mortality
Antibacterial
Active but the
Dried root
(Streptococcus-beta
concentration
bark (EtOH)
hemolytic)
was not given
Active but the
Antibacterial
Dried root
concentration
(Proteus mirabilis) bark (H2O)
was not given
Antibacterial
Active but the
Alkaloid
(Klebsiella
concentration
fraction
pneumoniae)
was not given
Antibacterial
Active but the
Glycoside
(Pseudomonas
concentration
mixture
aeruginosa)
was not given
Active but the
Antibacterial
Dried root
concentration
(Escherichia coli) bark (H2O)
was not given
Active in rat at a
dose of 500 mg/kg
Dried seed with inhibition of
Hypotriglyceridemia (flavonoid enzyme increase
fraction)
versus
CCl4-Induced
hepatotoxicity
Dried seed Active in rat at a
Antihepatotoxic
(flavonoid dose of 500 mg/kg
Reference
Adegoke et
al. (1998)
Oruambo
(1989)
Okunji and
Iwu (1988)
Ebana et al.
(1991)
Ebana et al.
(1991)
Ebana et al.
(1991)
Ebana et al.
(1991)
Ebana et al.
(1991)
Braide
(1991a)
Braide
(1991a)
Chapter 3 Pharmacological Activities of African Garcinia Plants
Plant
Part used
Effects
(Extracting In vivo
species
(Organism tested)
(Country)
solvent)
fraction)
with inhibition of
enzyme increase
versus
CCl4-Induced
hepatotoxicity
Active in rat at a
dose of 500 mg/kg
Dried seed with inhibition of
Glutathione
(flavonoid enzyme increase
depletion inhibition
fraction)
versus
CCl4-Induced
hepatotoxicity
The dose used in n
rat 200 mg/kg.
Commercial The
Barbiturate
sample of
hexobarbitol-indu
potentiation
seed
ced sleeping time
increased on days
1-7
Antibacterial
(Bacillus subtilis,
Escherichia coli,
Dried seed
Bacillus
(EtOAc)
megaterium,
Staphylococcus
aureus)
Antifungal
(Aspergillus niger)
Dried seed
(flavonoid
fraction)
Spasmolytic
Dried seed
(alkaloid
fraction)
Molluscicidal
(Bulinus globosus)
Dried seed
(H2O)
Reference
Braide
(1991a)
Braide
(1991b)
In agar plate,
it was active at Madubunyi
a conc of 100 (1995)
µg/ml
In agar plate,
it was active at Madubunyi
a conc of 100 (1995)
µg/ml
Dried seed
(EtOAc)
Spasmolytic
In vitro
55
Active in an ileum
& duodenum of
Guinea pig at a
conc of 12.5
µg/ml vs
Histamine-induce
d contractions.
Active in an ileum
& duodenum of
Guinea pig at a
conc of 12.5
µg/ml vs
Histamine-induce
d contractions.
Braide
(1989)
Braide
(1989)
Active against
Okunji and
Bulinus
Iwu (1988)
globosus at a
56
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Plant
Part used
Effects
(Extracting In vivo
species
(Organism tested)
(Country)
solvent)
Molluscicidal
(Bulinus globosus)
Dried seed
(MeOH)
Molluscicidal
(Lymnaea
natalensis)
Dried seed
(MeOH)
Antidiarrheal
Antiobesity
Dietary intake
Active in a male
rat at a conc of
Seeds
10% of diet vs
castor oil-induced
diarrhea.
Active in a male
rat at a conc of
20% of diet.
Seeds
Feeding for 6
weeks decreased
body weight from
134 to 110 gm/rat
The seed powder
incooperated on
animal feed was
studied on serum
levels of
electrolytes and
heavy metals on
male albino rats.
The pair-fed
controls received
Seed powder basal feed diet
daily for six
weeks. Results
showed a
significant (P<
0.05) dose
dependent
elevation of serum
CI-, HCO3,
Ca2+,Mg2+, Cu2+,
Zn2+ and Mn2+
In vitro
conc of 100
μg/ml
Strong activity
against
Bulinus
globosus at a
conc of 100
μg/ml
Strong activity
against
Lymnaea
natalensis at a
conc of 100
μg/ml
Reference
Okunji and
Iwu (1988)
Okunji and
Iwu (1988)
Okunji and
Iwu (1988)
Braide
(1990)
Agada and
Braide
(2009)
Chapter 3 Pharmacological Activities of African Garcinia Plants
Plant
Part used
Effects
(Extracting In vivo
species
In vitro
(Organism tested)
(Country)
solvent)
Studied on mice
with 10 mg/kg
methamphetamine
used to induce
neurotoxicity and
200 mg/kg of
extract was taken
Kolanut
orally. Results
Hepatoprotective
(H2O)
indicated the
serum levels of
some of the
marker enzymes
and bilirubin to
decrease
significantly (P <
0.05).
Antibacterial
(Escherichia coli)
G. kola
(from DR
Congo)
Dried seed
(CH2Cl2)
Antimalarial
(Plasmodium
falciparum)
Dried seed
(EtOH)
Antimalarial
(Plasmodium
falciparum)
Dried stem
bark
(CH2Cl2)
Antimalarial
(Plasmodium
falciparum)
Dried stem
bark (EtOH)
Antiamebic
(Entamoeba
histolytica)
Decoction
Antibacterial
(Klebsiella
pneumoniae)
Dried stem
bark (Tannin
fraction)
Oze et al.
(2010)
Adegboye
et al.,
(2008)
Seed
Antimalarial
(Plasmodium
falciparum)
Reference
Active against
P. falciparum
at a
concentration
of 6 μg/ml
Active against
P. falciparum
at a
concentration
of 6 μg/ml
Active against
P. falciparum
at a
concentration
of 6 μg/ml
Active against
P. falciparum
at a
concentration
of 6 μg/ml
Weak activity
was observed
at a MIC of
125 μg/ml
Active at a
concentration
of 120 μg/ml
Tona et al.
(1999)
Tona et al.
(1999)
Tona et al.
(1999)
Tona et al.
(1999)
Tona et al.
(1999)
Lutete
(1994)
57
58
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Plant
Effects
species
(Organism tested)
(Country)
Antibacterial
(Citrobacter
diversus)
Spasmolytic
G.
Cytotoxicty
livingstoneii
(CA-HUMAN(from South
COLON-CO-115)
Africa)
Cytotoxicty
(CA-HUMANCOLON-CO-115)
Part used
(Extracting In vivo
solvent)
Dried stem
bark (Tannin
fraction)
Active in the
Ileum of Guinea
pig at a conc of
Dried trunk
0.2 mg/ml.
bark
Oberved 70.3%
(Butanol
reduction
ext)
incontraction vs
KCl-Induced
contractions
Dried Leaf
(MeOH)
Dried root
bark
(CH2Cl2)
Cytotoxicty
Dried root
(Human Cancer cell bark
line HT 29)
(CH2Cl2)
Cytotoxicty
(Human Cancer cell
line, HT 620)
Antitumor
(CA-COLONSW 480)
Dried root
bark
(CH2Cl2)
Dried root
bark
(CH2Cl2)
Antifungal
(Cladosporium
cucumerinum)
Dried root
bark
(CH2Cl2)
Anticrustacean
(Artemia salina)
Dried root
bark
(CH2Cl2)
Molluscicidal
(Biomphalaria
glabrata)
Dried root
bark
(CH2Cl2)
Antifungal
(Cladosporium
cucumerinum)
Dried root
bark
(CH2Cl2)
G.
Cytotoxicity (A549, Fruit
livingstoneii DU145, KB and
(Ethanol)
In vitro
Reference
Active at a
Lutete
concentration
(1994)
of 95 μg/ml
Kambu
(1990)
Inactive-the
conc was not
given
Inactive-the
conc was not
given
In a cell
culture, it was
active with
IC50 value of
10.0 µg /ml
Active with
IC50 value of
8.0 µg /ml
Active with
IC50 value of
8.0 µg /ml
Active- at a
concentration
of 100
µg/plate
Active- with
LC50 value of
17.0 µg /plate
Seen inactive
at a
concentration
of 400 ppm
Active- at a
concentration
of 100
µg/plate
Active with an
average CC50
Chapuis et
al. (1988)
Sordat-Dise
rens et al.
(1992)
Sordat-Dise
rens et al.
(1992)
Sordat-Dise
rens et al.
(1992)
Sordat-Dise
rens et al.
(1992)
Sordat-Dise
rens et al.
(1992)
Cepleanu et
al. (1994)
Cepleanu et
al. (1994)
Cepleanu et
al. (1994)
Magadula
and
Chapter 3 Pharmacological Activities of African Garcinia Plants
Plant
Part used
Effects
(Extracting In vivo
species
(Organism tested)
(Country)
solvent)
(from
Kbivin)
Tanzania)
Antiviral (HIV-1
viral replication in
MT4 cells)
Fruit
(Ethanol)
Antimicrobial (E.
G. lucida
coli, P. aeruginosa, Stem bark
(from
S. typhi, S. aureus, (Methanol)
Cameroon)
C. albicans).
Stem bark
G. lucida
Tripanosomal (T. b. (1:1
(from
brucei)
CH2Cl2:Me
Cameroon)
OH mixture)
In vitro
Reference
value of
5.7-12.0
µg/ml
Inhibited the
HIV-1 viral
replication of
MT4 cells
with EC50
value of 2.25
µg/mL)
Active only to
C. albicans
with MIC
value of 64
μg/mL
Suleiman
(2010)
Magadula
and
Suleiman
(2010)
Momo et al.
(2011)
Activity value
Fotie at al.
at IC50 4.9
(2007)
μg/mL)
Crude extract
(100 μg/mL)
was able to
clear the
parasites
(100%
inhibition)
In a 1:1 conc
under cell
culture, it was
reported to be
active but the
conc was not
given
G. lucida
Antileishmanial
(from
(promastigote L.
Cameroon) donovani)
Stem bark
(1:1
CH2Cl2:Me
OH mixture)
G.
ovalifolia
(from
Central
African
Republic)
Antiviral
(Virus-HIV)
Dried Leaf
(CHCl3-Me
OH)
G.
ovalifolia
(from
Togo)
Antiyeast (Candida Dried Stem
albicans)
bark (EtOH)
Inactive at a
Kpakote et
concentration
al. (1998)
of 4.0 mg/ml
Antibacterial
(Staphylococcus
aureus)
Antibacterial
(Pseudomonas
aeruginosa)
Antifungal
(Aspergillus
fumigatus)
Active at a
concentration
of 4.0 mg/ml
Inactive at a
concentration
of 4.0 mg/ml
Active at a
concentration
of 4.0 mg/ml
Dried Stem
bark (EtOH)
Dried Stem
bark (EtOH)
Dried Stem
bark (EtOH)
59
Fotie at al.
(2007)
Gustafson
et al. (1992)
Kpakote et
al. (1998)
Kpakote et
al. (1998)
Kpakote et
al. (1998)
60
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Plant
species
(Country)
G.
polyantha
(from
Togo)
G.
verrucosa
ssp
orientalis
(from
Madagascar
)
Part used
Effects
(Extracting In vivo
(Organism tested)
solvent)
G. semseii
(from
Tanzania)
Cytotoxicity (A549,
Fruit
DU145, KB and
(Ethanol)
Kbivin)
Antifungal
(Aspergillus
fumigatus)
Cytotoxicity
(Murine P388 cell
line)
Antiviral (HIV-1
viral replication in
MT4 cells)
G. volkensii Antimicrobial,
(from
antioxidant and
Tanzania) Cytotoxicity
In vitro
Dried Stem
bark (EtOH)
Stem bark
(EtOAc)
Fruit hulls
(Ethanol)
Stem bark
(Ethanol)
Reference
Kpakote et
al. (1998)
Exhibited
99 %
inhibition of
the P388 cell
growth at a
concentration
of 10 μg/ml
Active with
CC50 value
range of
7.8-9.1
µg/mL)
Inhibited the
HIV-1 viral
replication of
MT4 cells
with EC50
value of 0.93
µg/mL)
Antibacterial
activity with
MIC values
ranging of
0.049->2.50
mg/ml. The
BST exhibited
LC50
value >100
μg/ml.
Rajaonarive
lo et al.
(2009)
Magadula
and
Suleiman
(2010)
Magadula
and
Suleiman
(2010)
Mbwambo
et al. (2011)
3.3 Antimalarial Activity
Malaria is one of the most serious protozoal diseases in man and ranks
number one in terms of morbidity in the tropical countries. It is estimated that at
least 40% of the world's population live in endemic areas, among which 90%
are distributed in Africa south of Sahara desert (Bruce-Chwatt et al., 1981). The
use of plant secondary metabolites as a cure and/or leads for the development of
Chapter 3 Pharmacological Activities of African Garcinia Plants
61
potential antimalarial compounds is a well known approach (Philipson and
Wright, 1990). Currently many medicinal plants, including Garcinia plants
from Africa have been investigated in vitro and/or in vivo testing for their
potential antimalarials.
Tona and co-workers investigated 20 extracts from different parts of some
African medicinal plants used in Congolese traditional medicine for the
treatment of malaria. Of these, the dichloromethane and ethanol extracts of the
dried seeds of G. kola exhibited more than 60% inhibition of the Plasmodiun
falciparum growth in vitro at a test concentration of 6 μg/ml (Tona et al., 1999),
(Table 4).
In another study from G. polyantha, which is an important medicinal plant of
Cameroonian traditional medicine, phytochemical analysis of its different parts
gave xanthones, flavonoids, benzophenones and triterpenoids (Lannang et al.,
2008). The isolated compounds were tested for their in vitro antimalarial
potential. In this assay, only isoxanthochymol
(13) showed strong
chemosuppression of P. falciparum when tested in vitro (Lannang et al., 2008).
In a study from G. livingstoneii, a series of xanthones and flavonoids was
isolated and tested for antiparasitic activity against P. falciparum. One of the
isolates, a biflavonoid ent-naringeninyl-(I-3α,II-8)-4'-O-methylnaringenin (14),
showed a remarkable in vitro activity against P. falciparum with the IC50 value
of 6.0 μg/ml (Mbwambo et al., 2006). Other xanthones and biflavonoids
isolated from this plant were not active in this assay.
3.4 Anticancer Activity
Cancer is rapidly becoming a major health problem with a global burden of
about 8 million deaths worldwide (WHO, 2007). This problem is correlated
62
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
with the emergence of HIV/AIDS, in which malignancies occur as part of
opportunistic diseases due to depressed immune system and other life styles.
Since many people in Africa live in rural areas, treatment of cancer-related
illnesses has mostly involved plant extracts, since most of people can not afford
the costs of currently available anticancer drugs. This necessitates the need for
continued search for anticancer compounds from medicinal plants. Currently,
several anticancer extracts and compounds from African Garcinia plants have
been characterized and their activities against different types of human cancer
cell-lines established (Rajaonarivelo et al., 2009; Magadula & Suleiman, 2010;
Mbwambo et al., 2006).
A recent study from Garcinia plants collected in Tanzania; reported the
evaluation of ethanol extracts for their in vitro cytotoxicity against four human
cancer cell lines. Among the tested extracts, the fruit extract of G. livingstoneii
and fruit hulls of G. semseii showed moderate to mild cytotoxic activities
against A549, DU145, KB and Kbivin human cell lines, with 50 % cytotoxic
(CC50) values ranging from 5.7-20.0 µg/ml (Magadula and Suleiman, 2010),
whereby taxol was used as a positive control. Rajaonarivelo and co-workers
investigated the cytotoxicity of the ethyl acetate extract of the stem bark of G.
verrucosa ssp orientalis, collected from the Eastern rain forest of Madagascar.
In this study the EtOAc extract exhibited 99 % in vitro inhibition of the P388
cell growth at a concentration of 10 μg/ml (Rajaonarivelo et al., 2009). In
another study on anticancer activity, a dichloromethane extract of the root bark
of G. livingstoneii; collected in South Africa exhibited in vitro growth
inhibitory activities against four human colon carcinoma cell lines. The human
cell lines tested were CO 115, SW 480, SW 620 and HT 29 with the IC50 values
of 10, 8, 8 and 10 μg/ml, respectively (Sordat-Diserens et al., 1992).
Chapter 3 Pharmacological Activities of African Garcinia Plants
63
Flavonoids possess various pharmacological properties including anticancer
activities (Iriti and Varoni, 2013). Two anticancer flavonoids have been
reported from the leaves of G. livingstoneii, namely; amentoflavone (1) and
4''-methoxy amentoflavone (2) (Kaikabo et al., 2009). The cytotoxicity of these
compounds was assessed using Vero monkey kidney cells. The authors showed
low toxicity against the cell line with LD50 values of 386 μg/ml and >600 μg/ml,
respectively (Kaikabo et al., 2009). In this test, berberine (CC50 = 170 μg/ml)
was used as a positive control. In a different study from the root bark of G.
livingstoneii, two dimeric xanthones, garcilivins A (15) and C (16) were
isolated and tested for in vitro cytotoxicity against MRC-5 cells. Compound 15
showed a higher and nonselective cytotoxicity (IC50 = 2.0 μg/ml), than its
diastereoisomer, compound 16 (IC50 = 52.3 μg/ml) (Mbwambo et al., 2006).
Further investigation from the root bark of G. livingstoneii gave two xanthones,
6,11-dihydroxy-2,2-dimethyl-pyrano[3,2-c]xanthone (17) and 4- (3’, 7’dimethylocta-2’,
6’-dienyl)-1,3,5-trihydroxy-9H-xanthone
(18).
These
compounds inhibited the growth of SW 480 and CO 115 human colon
carcinoma cells with compound 18 (IC50 = 0.6 μg/ml) showing comparable
activity to the synthetic drug, 5-fluorouracil (IC50 = 0.4 μg/ml) (Sordat-Diserens
et al., 1992).
The bioassay-guided fractionation of the EtOAc extract of the stem bark of G.
verrucosa led to the isolation of a new cytotoxic polycyclic prenylated
acylphloroglucinol, named garcicosin (19). This compound was observed to
inhibit P388 cell growth at a concentration of 10 μg/ml with an IC50 value of 3.0
μg/ml. (Rajaonarivelo et al., 2009).
The study by Dibwe and co-workers on the chloroform extract of Garcinia
huillensis indicated a preferential cytotoxicity (PC50 = 17.8 µg/mL) against
human pancreatic cancer PANC‐1 cells under nutrient‐deprived conditions.
64
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Further investigation of the active constituents revealed 12 known
anthraquinones together with a damnacanthal (20). Compound 20 caused
preferential necrotic cell death of PANC‐1 and PSN‐1 cells under
nutrient‐deprived and serum‐sensitive conditions of PC50 = 4.46 µm and
3.77 µm, respectively (Dibwe et al., 2012).
3.5 Antioxidant Activity
Antioxidants such as dietary flavonoids work by scavenging free radicals,
chelation of metal ions, and decomposition of peroxides such as lipid peroxides
(Dufresne and Farnsworth, 2001). It is well established that; phenolic
compounds are known to be antioxidants with excellent hydrogen or electron
donor capacity (Chiang et al., 2003). It has been suggested that the antioxidant
effect of Garcinia plants is ascribed mostly to biflavonoids (Farombi et al.,
2002). Thus, they are thought to play important role in the prevention of various
human disorders as free radical scavengers.
Garcinia kola, a tropical plant which grows in moist forest, has found to have
many applications in traditional medicine, especially in the West and Central
African sub-region. This plant is the highly investigated among all Garcinia
species growing in Africa. Farombi and co-workers investigated the antioxidant
and scavenging properties of a flavonoid extract of G. kola seeds. The in vitro
assay involved the free radicals and reactive oxygen species from which the
flavonoid extract, commonly known as kolaviron, exhibited noticeably reducing
power and antioxidant activity by inhibiting the peroxidation of linoleic acid. It
further exhibited 57% scavenging effect on superoxide at a concentration of 1
mg/ml and 85% scavenging activity on hydrogen peroxide at a concentration of
1.5 µg/ml. Similarly, flavonoid extract, at a concentration of 2 mg/ml, showed a
89% scavenging effect on a,a-diphenylb-picrylhydrazyl radical (DPPH),
Chapter 3 Pharmacological Activities of African Garcinia Plants
65
indicating that the extract has effective activities as a hydrogen donor and as a
primary antioxidant to react with lipid radicals (Farombi et al., 2002). The
protective effects of kolaviron, a Garcinia biflavonoid extract from the seeds of
G. kola widely consumed in some West African countries, was tested against
oxidative damage to molecular targets ex-vivo and in vitro. Treatment with
hydrogen peroxide (H2O2) at a concentration of 100 μg/ml increased the levels
of DNA strand breaks and oxidized purine and pyrimidine bases in both human
lymphocytes and rat liver cells using alkaline single cell gel electrophoresis
(COMET assay). Kolaviron was protective at concentrations between 30-90
μg/ml and decreased H2O2-induced DNA strand breaks and oxidized bases
(Farombi et al., 2004). Furthermore, kolaviron exhibited protective effects
against oxidative damage to molecular targets via scavenging of free radicals
and iron binding (Farombi et al., 2004).
In another study by Farombi and co-workers, the antioxidant and radical
scavenging activities were investigated from the flavonoid fraction of the seeds
of G. kola. The extract was fed to the male rats for six weeks and their body
weights decreased from 134 to 110 gm/rat (Table 3) (Farombi et al., 2002).
Further studies from the seeds of G. kola indicated the methanolic extract to
show
many
activities.
Methanol
extract
was
subjected
to
column
chromatography under silica gel to give five fractions, and each fraction was
tested for the free radical scavenging activities and antioxidant potentials for
various in vitro models (Okoko, 2009). Results indicated that the fourth fraction
possessed the highest antioxidant and radical scavenging activities as compared
with the rest of fractions. It was also established that the fourth fraction strongly
inhibited nitric oxide production in lipopolysaccharide activated macrophage
U937 cells (Okoko, 2009). The CH2Cl2/MeOH (1:1) extract of the stem bark of
G. afzelii was found to exhibit significant anti-oxidant effects, based on the
scavenging of the stable DPPH free radical showing the IC50 value of 20.5
66
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
μg/100 ml (Waffo et al., 2006). Two novel prenylated xanthones,
afzeliixanthones A (21) and B (22), were isolated and tested for their
antioxidative properties. The two compounds showed high antioxidant activity
with the IC50 values of 17.7 and 14.0 μg/100 ml comparable to α-tocopherol (23)
(IC50 13.5 μg/100 ml) as a standard (Waffo et al., 2006).
In another study by Okoko on the methanol extract of the seeds of G. kola,
column chromatographic fractionation under silica gel and spectroscopic
analysis of the active fraction revealed the presence of four compounds namely
garcinia biflavonoids GB1 (3) and GB2 (24), garcinal (25) and garcinoic acid
(26). These four compounds were reported to be responsible for the great
antioxidant potential of Garcinia kola seeds (Okoko, 2009). Further work by
Terashima and co-workers investigated the structure-antioxidative activity
relationships of derivatives based on garcinoic acid (26) from Garcinia kola,
which led to the discovery of a powerful antioxidative agent of a chromen
moiety (compound 27) that showed activity of 18.7 higher than standard
compound, 23 (Terashima et al., 2002).
Chapter 3 Pharmacological Activities of African Garcinia Plants
67
OH
HO
OH
HO
O
O
O
OH
OH
O
O
HO
O
OH
13
OH
OH
O
O
OH
OH
OH
O
O
OH
O
15 beta-H
16 alpha-H
OH
O
O
R
O
O
14
R
OH
O
OH
O
O
O
OH
OCH3
CHO
i-Pr
OH
18
17
O
OCH3
O
HO
15
OH
HO
O
OH
O
O
21
20
19
O
OCH3
CH3
H3CO
HO
O
OH
OH
H3C
O
CH3
22
23
CH3
O
OH
HO
O
HO
OH
OH
O
HO
O
O
25
R
CHO
26
COOH
CH3
O
OH
OH
OH
R
HO
27
24
Fig. 20. Structures of bioactive compounds isolated from some African Garcinia plants
(Cont).
68
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Phytochemical analysis from the chloroform extract of the stem bark of G.
polyantha
resulted
in
the
isolation
of
four
prenylated
xanthones,
bangangxanthones A (28) and B (29), 1,5-dihydroxyxanthone (30) and
2-hydroxy-1,7-dimethoxyxanthone (31) that were screened for DPPH radical
scavenging activity (Lannang et al., 2005). Compound 28 showed significant
activity with IC50
value
of
87.0 μg/ml
relative
to the
standard,
3-t-butyl-4-hydroxyanisole (IC50 = 42.0 μg/ml). Likewise, compound 29
showed weak activity with IC50 of 482.0 μg/ml, while compounds 30 and 31
showed 47.8% and 39.5% of inhibition respectively, at the concentration of 1
μg/ml (Lannang et al., 2005).
In the search for antioxidant compounds from G. buchananii, Stark et al.
(2012), isolated and identified three 3,8″-linked biflavanones and two
flavanone-C-glycosides biflavonoids using hydrogen peroxide scavenging and
oxygen radical absorbance capacity (ORAC) assays. The compounds included a
biflavanone GB-2 (24), manniflavanone (32), taxifolin- 6- C- β- Dglucopyranoside
(33),
aromadendrin-6-C-β-D-glucopyranoside
(34)
and
buchananiflavanone (35). Manniflavanone (32) and GB-2 (24) showed high
H₂O₂ scavenging activity with EC₅₀ values of 2.8 and 2.2 μM, respectively and
the ORAC activities of 13.73 and 12.10 μmol TE/ μmol, respectively, (Stark et
al., 2012).
3.6 Antiviral Activity
In the absence of a vaccine and efficient treatment, HIV/AIDS continues to
be a growing public health problem in the world. The rising number of
HIV/AIDS cases in Africa has raised the demand for medical care and
consequently has created a burden to the available limited health budgets.
Chapter 3 Pharmacological Activities of African Garcinia Plants
69
Consequently, this has raised the interest of screening crude plant extracts for
anti-HIV activity, while little research has been done on pure compounds.
Two Garcinia plants growing in Tanzania has been evaluated for their in
vitro anti-HIV activity against HIV-1 viral replication in MT4 cells. The ethanol
extracts of the fruits of G. livingstonei and G. semseii revealed significant
anti-HIV-1 activity with EC50 values of 2.25 ± 0.51 and 0.93 ± 0.67 µg/mL
respectively (Magadula & Suleiman, 2010). Furthermore, another study from
ethanol extracts of some Garcinia species collected in Tanzania were
investigated for their HIV-1 protease (HIV-1 PR) inhibitory activities using
high performance liquid chromatography (HPLC). Among the tested extracts,
the fruit hulls of G. semseii showed the most potent inhibitory activity against
HIV-1 PR with an IC50 value of 5.7 μg/ml, followed by the stem bark extracts of
G. edulis and G. kingaensis with IC50 values of 9.2 and 15.2 μg/ml, respectively
(Magadula & Tewtrakul, 2010). In another study, the chloroform-methanol (1:1)
extract of the dried leaf of G. ovalifolia, collected from Central African
Republic, showed significant anti-HIV activity when tested in vitro (Gustafson
et al., 1992).
Benzophenones are phenolic compounds which are reported to display
antiviral activity. For instance, a polyisoprenylated benzophenone, guttiferone
A (36) isolated from the fruits of G. livingstonei was found to inhibit the
cytopathic effects in human lymphoblastoid CEM-SS cells in vitro, with EC50
values of ≤ 10 μg/ml (Gustafson et al., 1992). Phytochemical investigation of
the root bark of G. edulis gave a new isoprenylated xanthone, 1, 4, 6-trihydroxy
-3-methoxy-2- (3-methyl-2-butenyl)-5-(1,1-dimethyl-prop-2-enyl)xanthone (37)
that showed significant in vitro anti-HIV-1 protease activity with IC50 value of
11.3 μg/ml (Magadula, 2010).
70
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
OH
O
OH
O
OH
O
O
OH
O
O
O
OH
OH
28
OH
OH
30
29
OH
OH
OH
O
H3CO
OH
O
OH
OH
OH
O
HO
31
R1
R2
OH
OH
O
O
HO
O
HO
OCH3
O
33
OH
R1
R2
glucose
34
H
glucose
O
OH
R
OH
O
32
35
R
OH
H
OH
HO
HO
O
HO
O
OCH3
OH
O
O
36
37
Fig. 20. Structures of bioactive compounds isolated from some African Garcinia plants
(Cont).
3.6 Other Biological Activities
The phytochemical study on the methanol extract of the wood trunk of G.
polyantha, gave a series of oxygenated xanthones that were screened for their
anticholinesterase
potentials
on
acetylcholinesterase
(AChE)
and
butyrylcholinesterase (BChE) enzymes (Louh et al., 2008). Polyanxanthones
A-C (38-40), 1,3,5-trihydroxyxanthone (41), 1,5-dihydroxyxanthone (30) and
1,6-dihydroxy-5-methoxyxanthone (42) showed noteworthy inhibitory activities.
Compounds 30, 40 and 41 showed significant inhibition against BChE with an
Chapter 3 Pharmacological Activities of African Garcinia Plants
71
IC50 value of 93.0, 2.54 and 74.4 μg/ml, respectively, while compound 39
showed significant inhibition against both AChE (IC50 = 46.3 μg/ml) and BChE
(IC50 = 25.5 μg/ml) compared to the standard, galantamine (IC50 = 0.5 and 8.5
μg/ml, respectively). Compound 38 indicated 41.8% and 7.0% inhibition
against AChE and BChE, respectively, at the concentration of 0.2 mg/ml (Louh
et al., 2008).
Kolaviron, the predominant constituent in G. kola, is a biflavonoid complex
[containing biflavanones GB-1 (3) and GB-2 (24) and kolaflavanone (43)] that
has been reported to prevent hepatotoxicity mediated by several toxins (Iwu et
al., 1987). Similarly, kolaviron exhibited hypoglycemic effects in normal and
alloxan- and streptozotocin-induced diabetic animals (Adaramoye et al., 2006).
In another study for kolaviron, the protein expression levels of cyclooxygenase
(COX-2) and inducible nitric oxide synthase (iNOS) were evaluated by western
blotting, while DNA-binding activities of nuclear factor kappa B (NF-κB) and
activator protein-1 (AP-1) were determined by electrophoretic mobility shift
assay. The results indicated kolaviron to have an ability to inhibit COX-2 and
iNOS expression through down regulation of NF-κB and AP-1 DNA binding
activities, which could be a mechanism for the hepatoprotective properties of
kolaviron (Farombi et al., 2009).
In the study by Balemba and co-workers, the stem bark of G. buchananii
inhibited propulsive motility and fast synaptic potentials in the guinea pig distal
colon. The result indicated a concentration-dependent manner, with an optimal
concentration of about 10 mg/ ml. In this study, no any active principle was
isolated from the active fractions (Balemba et al., 2010). Further study from the
same plant investigated the potential of the constituents on reducing
gastrointestinal peristaltic activity via 5-HT(3) and 5-HT(4) receptors.
Phytochemical screening of the crude extract indicated the presence of
72
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
flavonoids, steroids, alkaloids, tannins and phenols. The results revealed that the
anti-motility effects of the aqueous extract of G. buchananii are significantlly
mediated by compounds that affect 5-HT(3) and 5-HT(4) receptors. However,
no single compound was characterized or identified from the active components
(Boakye et al., 2012). Furthermore, the G. buchananii extract and its
anti-motility fractions were studied to be effective remedies against
lactose-induced diarrhea. Results indicated that the active extract contained
compounds that are responsible for reducing the body weight and supporting the
upward intake of food and water (Boakye et al., 2012).
Depsidones isolated from Garcinia plants are reported to possess many
biological activities (Ito et al., 2001). In a phytochemical study from the stem
bark of G. brevipedicellata collected in Cameroon, four new depsidones named
brevipsidones A-D (44-47) were isolated and evaluated for their possible
glycosidase enzyme inhibitory activity against α-glucosidase. These compounds
showed moderate α-glucosidase inhibition with IC50 values of 21.2, 27.8, 59.6
and 7.04 μg/ml respectively (Ngoupayo et al., 2008).
The crude extract of the stem bark of the G. lucida indicated a significant
trypanocidal and antileishmanial activities. The bioassay guided isolation of the
constituents
of
the
benzo[c]phenanthridine
stem
bark
alkaloids,
led
to
the
isolation
dihydrochelerythrine
of
(48),
three
6-
acetonyldihydrochelerythrine (49) and lucidamine A (50). The isolated
compounds as well as the crude extract displayed poweful antiprotozoal activity
against Trypanosoma brucei brucei and Leishmania donovani, with little
toxicity to Vero cells and the host cells (Fotie et al., 2007). The crude extract of
G. lucida displayed significant activity against T. b. brucei (IC50 4.9 μg/mL)
with no toxicity on the Vero cell. The isolated compounds, the
dihydrochelerythrine derivatives (48-50) exhibited interesting activity, with IC50
Chapter 3 Pharmacological Activities of African Garcinia Plants
73
values in the range 0.8–14.1 μM. Dihydrochelerythrine (48) was the most potent
compound (IC50 0.8 μM), with more than 44-fold selectivity for T. b. brucei
parasites over Vero cells (Fotie et al., 2007). When tested on promastigote L.
donovani, the crude extract (100 μg/mL) and compounds 48-50 (100 μM) were
able to clear the parasites (100% inhibition), whereas at 10 μM, these
compounds achieved about 89, 87, and 76% inhibition, respectively.
Phytochemistry of
African Garcinia
Plants
76
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
4.1 Introduction
Many African countries are endowed with tropical forests that are rich in the
diversity of plants. These plants constitute a rich, but largely untapped pool of
natural products as chemicals with potential socio-economic benefits. Given
that the occurrence of many secondary metabolites is genus or species specific,
probability is high that many plants contains potentially useful biological
properties that will remain undiscovered, unidentified and unused; this is a true
case for tropical African rain forests. Presently, many medicinal plants,
including Garcinia plants, are threatened with extinction or severe genetic loss,
while their detailed scientific information is still lacking. Hence, a continued
and sustainable biological and chemical investigation of these useful plants is
needed.
From the Garcina plants growing in Africa, more than 130 secondary
metabolites have been isolated, with benzophenones, flavonoids, triterpenoids
and xanthones being the major constituents (Table 5). Furthermore, about 18
other compounds have been reported from African Garcinia species. From all
the African Garcinia plants, the most well-known and phytochemically studied
is G. kola which is reported to grow in almost all West and Central African
countries (Iwu et al., 1990, Madubunyi, 1995, Okunji & Iwu, 1991, Kapadia et
al., 1994). However, these phytochemical reports still indicate that only a small
fraction of African Garcinia plants have been studied for their chemical
constituents. This necessitates further work to be done for an uninvestigated
species.
Chapter 4 Phytochemistry of African Garcinia Plants
77
Table 5. Compounds isolated from the African Garcinia species.
Class
Name
Plant species Part
Where
Reference
collected
Garcinol (51)
G. huillensis
Stem bark
Cameroon
Xanthochymol (52)
G. staudtii
Stem bark
Nigeria
G. mannii
Stem, leaves
Cameroon
& seeds
G. polyantha Stem bark
Cameroon
Semsinone A (53)
G. semseii
Stem bark
Tanzania
Semsinone B (54)
G. semseii
Stem bark
Tanzania
Semsinone C (55)
G. semseii
Stem bark
Tanzania
G. semseii
G. semseii
G.
livingstoneii
Fruit hulls
Fruit hulls
Tanzania
Tanzania
Fruit
Tanzania
Guttiferone E (57)
G. ovalifolia
Leaf
CAR
Isoxanthochymol (13)
G. ovalifolia
Leaf
CAR
Benzophen Guttiferone K (56)
ones
Guttiferone A (36)
Kolanone (58)
Biflavanone GB-1 (3)
G. polyantha Stem bark
Cameroon
G. polyantha Root bark
Cameroon
G. kola
Fruit pulp
Nigeria
G. kola
Dried root
Nigeria
G. kola
Dried seed
Nigeria
G. buchananii Heartwood
Uganda
Jackson et al.
(1971)
Cameroon
Hussain and
Waterman (1982)
G. kola
Leaf, Seed,
Stem bark,
heartwood
Dried seed
G. kola
Stem bark,
G. kola
Root bark
G. mannii
Flavonoids
Bakana et al.
(1987)
Waterman and
Hussain (1982)
Hussain and
Waterman (1982)
Ampofo et al.
(1986)
Magadula et al.
(2008)
Magadula et al.
(2008)
Magadula et al.
(2008)
Magadula (2012)
Magadula (2012)
Gustafson et al.
(1992)
Gustafson et al.
(1992)
Gustafson et al.
(1992)
Ampofo et al.
(1986)
Lannang et al.
(2008)
Hussain et al.
(1982)
Iwu et al. (1990)
Madubunyi
(1995)
Biflavanone GB-2 (24) G. buchananii Heartwood
Nigeria
DR
Congo
Nigeria
Uganda
Iwu (1985)
Kabangu et al.
(1987)
Han et al. (2005)
Jackson et al.
(1971)
78
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Class
Name
Plant species Part
G. kola
Leaf, Seed,
Stem bark,
heartwood
Dried seed
G. kola
Stem bark,
G. kola
Dried stem
Nigeria
G. buchananii Heartwood
Uganda
G. mannii
Biflavanone GB-1A
(59)
Biflavanone GB-1B
(60)
Biflavanone GB-2A
(61)
Cyanidin (62)
Eriodictyol (63)
Where
Reference
collected
Cameroon
Nigeria
DR
Congo
G. mannii
Leaf, Seed,
Stem bark,
heartwood
Cameroon
G. volkensii
Heartwood
Kenya
G. kola
Dried stem
Nigeria
G. kola
Dried stem
Nigeria
G. buchananii Heartwood
Uganda
G. mannii
Leaf, Seed,
Stem bark,
heartwood
Cameroon
G. volkensii
Heartwood
Kenya
G. kola
Dried stem
Nigeria
G.
Stem & seed Cameroon
chromocarpa
Stem, seed &
G. conrauana
Cameroon
leaf
Fukugetin (64)
G. conrauana Heartwood
Cameroon
O-Methylfukugetin
(65)
G. conrauana
Stem,
heartwood
Cameroon
G. quadrifaria Stem bark
Cameroon
G. densivenia Stem bark
Cameroon
Manniflavanone (32)
G. mannii
G. kola
Seed, Leaf,
Stem bark,
heartwood
Dried root
G. conrauana Leaves
Morelloflavone
G. mannii
Heartwood
Cameroon
Nigeria
Hussain and
Waterman (1982)
Iwu (1985)
Kabangu et al.
(1987)
Terashima et al.
(1999a)
Jackson et al.
(1971)
Hussain and
Waterman (1982)
Herbin et al.
(1970)
Terashima et al.
(1999a)
Terashima et al.
(1999a)
Jackson et al.
(1971)
Hussain and
Waterman (1982)
Herbin et al.
(1970)
Terashima et al.
(1999a)
Gartlan et al.
(1980)
Hussain and
Waterman (1982)
Hussain and
Waterman (1982)
Hussain and
Waterman (1982)
Waterman and
Hussain (1982)
Waterman and
Crichton (1980)
Hussain and
Waterman (1982)
Iwu et al. (1990)
Hussain and
Cameroon
Waterman (1982)
Cameroon Hussain and
Chapter 4 Phytochemistry of African Garcinia Plants
Class
Name
Stem bark
Where
Reference
collected
Waterman (1982)
Mbafor et al.
Cameroon
(1989)
Tanzania Stark et al. (2012)
Stem bark
Tanzania Stark et al. (2012)
Stem bark
Tanzania Stark et al. (2012)
Root bark
Tanzania
G. volkensii
Stem bark
Tanzania
G.
livingstoneii
Root bark
Tanzania
Plant species Part
glycoside (66)
Taxifolin-6-C-β-D-gluc
G. epunctata
opyranoside (33)
G. buchananii
Aromadendrin-6-C-β-D
G. buchananii
-glucopyranoside (34)
Buchananiflavanone
G. buchananii
(35)
G.
Volkensiflavone (67)
livingstoneii
Morelloflavone (68)
Garcinia biflavanone
GB-2 (24)
Amentoflavone (1)
Stem bark
G. quadrifaria Stem bark
Cameroon
G. densivenia Stem bark
Cameroon
G. volkensii
Heartwood
Kenya
G. volkensii
Stem bark
Tanzania
Stem bark
Cameroon
Root bark
Tanzania
Root bark
Dried Seed
Nigeria
Nigeria
G. kola
Dried Seed
Nigeria
G. kola
Dried seed
Nigeria
G. kola
Dried seed
Nigeria
G. kola
Dried seed
Nigeria
G. kola
Dried seed
Nigeria
G. kola
Dried seed
Nigeria
G. kola
Dried seed
Nigeria
G. kola
Dried seed
Nigeria
G. kola
Dried stem
Nigeria
G.
Leaf
South
ent-Naringeninyl-(I-3α,
II-8)-4'-O-methylnaring G. quadrifaria
enin (14)
G.
livingstoneii
Kolaflavanone (43)
G. kola
G. kola
Garcinia biflavanone
GB-1 (3)
79
Mbwambo et al.
(2006)
Mbwambo et al.
(2011)
Mbwambo et al.
(2006)
Waterman and
Hussain (1982)
Waterman and
Crichton (1980)
Herbin et al.
(1970)
Mbwambo et al.
(2011)
Waterman and
Hussain (1982)
Mbwambo et al.
(2006)
Iwu et al. (1990)
Iwu (1985)
Kapadia et al.
(1994)
Okunji & Iwu
(1991)
Iwu and Igboko
(1982)
Iwu et al. (1987)
Madubunyi
(1995)
Okunji and Iwu
(1991)
Iwu et al. (1987)
Madubunyi
(1995)
Terashima et al.
(1999a)
Kaikabo et al.
80
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Class
Name
Plant species Part
livingstoneii
4''-Methoxyamentoflav G.
one (2)
livingstoneii
Where
collected
Africa
South
Africa
Reference
Apigenin (71)
G. nervosa
Dried leaf
Nigeria
3,8''-Biapigenin (72)
G. nervosa
Dried leaf
Nigeria
Nervosin (73)
Irigenin (74)
7-Methyltectorigenin
(75)
I-5, II-5
I-7,II-7,I-3’,I-4’,
II-4’-Heptahydroxy-[I3,
II-8]-flavanonylflavone
flavanoylflavone (76)
I-3, II-3, I-5, II-5, I-7,
II-7,
I-4',II-4'-Octahydroxy
[I-2', II-2'] biflavone
(77)
G. nervosa
G. nervosa
Dried leaf
Dried leaf
Nigeria
Nigeria
(2009)
Kaikabo et al.
(2009)
Iwu and Igboko
(1982)
Terashima et al.
(1995)
Terashima et al.
(1997)
Kapadia et al.
(1994)
Kapadia et al.
(1994)
Parveen et al.
(2004)
Parveen et al.
(2004)
Ilyas et al. (1994)
Ilyas et al. (1994)
G. nervosa
Dried leaf
Nigeria
Ilyas et al. (1994)
G. nervosa
Dried leaf
Nigeria
Babu et al. (1988)
G. nervosa
Dried leaf
Nigeria
Parveen et al.
(2004)
Quercetin (78)
G. nervosa
Dried leaf
Nigeria
Taxifolin (79)
G. buchananii Stem bark
Parveen et al.
(2004)
Tanzania Stark et al. (2012)
Friedelin (80)
G. ovalifolia
Stem bark
Cameroon
G. polyantha Stem bark
Cameroon
G. edulis
Root bark
Tanzania
G. lucida
Stem bark
Cameroon
G. polyantha Stem bark
Cameroon
G. lucida
Cameroon
Leaf
Acacetin (69)
G. kola
Seed
Nigeria
Garcinianin (70)
G. kola
Dried stem
Nigeria
G. kola
Dried seed
Nigeria
Dried seed
Nigeria
Dried seed
Nigeria
Kolabiflavonoid GB-1
G. kola
(3)
Kolabiflavonoid GB-2
G. kola
(24)
Triterpenoi
ds
Oleanolic acid (81)
Stem bark
Waterman et al.
(1980)
Lannang et al.
(2005)
Magadula (2010)
Momo et al.
(2011)
Lannang et al.
(2005)
Momo et al.
Chapter 4 Phytochemistry of African Garcinia Plants
Class
Name
Plant species Part
Lupeol (82)
G. polyantha Stem bark
Where
Reference
collected
(2011)
Lannang et al.
Cameroon
(2005)
Tanzania Magadula (2010)
Magadula et al.
Tanzania
(2008)
Tanzania Magadula (2010)
Lannang et al.
Cameroon
(2008)
Lannang et al.
Cameroon
(2008)
Cameroon Fotie et al. (2007)
Momo et al.
Cameroon
(2011)
Momo et al.
Cameroon
(2011)
Momo et al.
Cameroon
(2011)
G. edulis
Root bark
Achilleol A (83)
G. semseii
Stem bark
Lupeol acetate (84)
G. edulis
Root bark
Garcinane (85)
G. polyantha Root bark
Magnificol (86)
G. polyantha Root bark
Betulinic acid (87)
G. lucida
Stem bark
G. lucida
Stem bark
Putranjivic acid (88)
G. lucida
Stem bark
Methyl putranjivate
(89)
G. lucida
Stem bark
Smeathxanthone A (10)
G.
Stembark
smeathmannii
Cameroon
G. polyantha Root bark
Cameroon
G.
Stembark
smeathmannii
Cameroon
G. polyantha Root bark
Cameroon
Smeathxanthone B (11)
1,3,5-Trihydroxyxantho G.
ne (41)
smeathmannii
G. polyantha
1,3-dihydroxyxanthone G.
smeathmannii
(90)
Xanthones
G. polyantha
Rheediaxanthone (91)
Rheediaxanthone A
(92)
Bangangxanthone A
(28)
Bangangxanthone B
(29)
1,5-Dihydroxyxanthone
(30)
Stembark
Cameroon
Wood trunk Cameroon
Stembark
81
Cameroon
Wood trunk Cameroon
G. staudtii
Stembark
Nigeria
G. staudtii
Stembark
Nigeria
G. polyantha Stem bark
Cameroon
G. polyantha Stem bark
Cameroon
G. polyantha Stem bark
Cameroon
G. afzelii
Stem bark
Cameroon
2-Hydroxy-1,7-dimetho G. polyantha Stem bark
Cameroon
Komguem et al.
(2005)
Lannang et al.
(2008)
Komguem et al.
(2005)
Lannang et al.
(2008)
Komguem et al.
(2005)
Louh et al. (2008)
Komguem et al.
(2005)
Louh et al. (2008)
Waterman and
Hussain (1982)
Waterman and
Hussain (1982)
Lannang et al.
(2005)
Lannang et al.
(2005)
Lannang et al.
(2005)
Waffo et al.
(2006)
Lannang et al.
82
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Class
Name
Plant species Part
xyxanthone (31)
1,4,5-Trihydroxy-3-(3G.
methylbut-2-enyl)-9Hlivingstoneii
xanthen-9-one (7)
G.
livingstoneii
6,11-Dihydroxy-3-meth
yl-3-(4-methylpent-3-e G.
nyl)pyrano[2,3-c]xanth livingstoneii
one (8)
G.
livingstoneii
4[(E)-3,7-Dimethylocta
-2,6-dienyl]-1,3,5-trihy G.
droxy-9H-xanthen-9-on livingstoneii
e (9)
G.
Garcilivin A (15)
livingstoneii
G.
livingstoneii
G.
Garcilivin B (93)
livingstoneii
G.
livingstoneii
G.
Garcilivin C (16)
livingstoneii
G.
livingstoneii
Root bark
Tanzania
Mbwambo et al.
(2006)
Root bark
South
Africa
Sordat-Diserens
et al. (1992)
Root bark
Tanzania
Mbwambo et al.
(2006)
Root bark
South
Africa
Sordat-Diserens
et al. (1992)
Root bark
Tanzania
Mbwambo et al.
(2006)
Root bark
Tanzania
Root bark
South
Africa
Root bark
Tanzania
Root bark
South
Africa
Root bark
Tanzania
Root bark
South
Africa
Stem bark
Cameroon
G. afzelii
Stem bark
Cameroon
G. afzelii
Stem bark
Cameroon
G. afzelii
Stem bark
Cameroon
G. polyantha Stem bark
Cameroon
Afzeliixanthone A (21) G. afzelii
Afzeliixanthone A B
(22)
1,7-Dihydroxyxanthone
(94)
1,3,7-Trihydroxy-2-(3methylbut-2-enyl)xanth
one (95)
Rheediaxanthone-B
(96)
Isorheediaxanthone-B
(97)
12b-Hydroxy-des-D-ga
rcigerrin A (6)
6,11-Dihydroxy-2,2-di
methyl-pyrano[3,2-c]xa
nthone (17)
4-(3’,7’-Dimethylocta-
Where
Reference
collected
(2005)
G. polyantha Stem bark
Mbwambo et al.
(2006)
Sordat-Diserens
et al. (1992)
Mbwambo et al.
(2006)
Sordat-Diserens
et al. (1992)
Mbwambo et al.
(2006)
Sordat-Diserens
et al. (1992)
Waffo et al.
(2006)
Waffo et al.
(2006)
Waffo et al.
(2006)
Waffo et al.
(2006)
Ampofo et al.
(1986)
Ampofo et al.
Cameroon
(1986)
South
Sordat-Diserens
Africa
et al. (1992)
G.
livingstoneii
Root bark
G.
livingstoneii
Root bark
South
Africa
Sordat-Diserens
et al. (1992)
G.
Root bark
South
Sordat-Diserens
Chapter 4 Phytochemistry of African Garcinia Plants
Class
Name
Plant species Part
2’, 6’-dienyl)
livingstoneii
-1,3,5-trihydroxy -9Hxanthone (18)
Garcigerrin A (4)
G. gerrardii
Root bark
Garcigerrin B (5)
Where
Reference
collected
Africa
et al. (1992)
South
Africa
South
Africa
Sordat-Diserens
et al. (1989)
Sordat-Diserens
et al. (1989)
G. gerrardii
Root bark
2-(1',l'-Dimethylprop-2'
-enyl)-1,4,5-trihydroxy G. gerrardii
xanthone (98)
Root bark
South
Africa
Sordat-Diserens
et al. (1989)
Macluxanthone (99)
Stem bark
Cameroon
Waterman et al.
(1980)
Cameroon
Waterman and
Hussain (1982)
G. ovalifolia
1,3,5-Trihydroxy-4,8-(3
’,3’-dimethylallyl)xanth G. quadrifaria Stem bark
one (100)
Garceduxanthone (37) G. edulis
Root bark
Forbexanthone (101)
G. edulis
Root bark
83
Tanzania Magadula (2010)
Tanzania Magadula (2010)
Waterman and
Pyranojacareubin (102) G. densivenia Stem bark
Cameroon
Crichton (1980)
Ampofo and
Nervosaxanthone (103) G. nervosa
Nigeria
Waterman (1986)
Garciniaxanthone I
Lannang et al.
Root bark
Cameroon
(2008)
(104)
Lannang et al.
Chefouxanthone (105)
Root bark
Cameroon
(2008)
Polyanxanthone A (38)
Wood trunk Cameroon Louh et al. (2008)
Polyanxanthone B (39)
Wood trunk Cameroon Louh et al. (2008)
Polyanxanthone C (40)
Wood trunk Cameroon Louh et al. (2008)
1,3,6,7-Tetrahydroxyxa
Wood trunk Cameroon Louh et al. (2008)
nthone (106)
1,6-Dihydroxy-5-metho
Wood trunk Cameroon Louh et al. (2008)
xyxanthone (42)
1,3,5,6-Tetrahydroxyxa
Wood trunk Cameroon Louh et al. (2008)
nthone (107)
1,2-Dihydroxyxanthone
Momo et al.
G. lucida
Stem bark
Cameroon
(2011)
(108)
1-Hydroxy-3-methoxyx
Momo et al.
G. lucida
Stem bark
Cameroon
anthone (109)
(2011)
Garcicosin (19)
Other
Compound
Brevipsidone A (44)
s
Brevipsidone B (45)
G. verrucosa
Stem bark
ssp orientalis
G.
brevipedicella Stem bark
ta
G.
Stem bark
brevipedicella
Madagasc Rajaonarivelo et
ar
al. (2009)
Cameroon
Ngoupayo et al.
(2008)
Cameroon
Ngoupayo et al.
(2008)
84
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Class
Name
Brevipsidone C (46)
Brevipsidone D (47)
β-Sitosterol (110)
Plant species Part
ta
G.
brevipedicella Stem bark
ta
G.
brevipedicella Stem bark
ta
G. afzelii
Stem bark
G. polyantha Root bark
Where
Reference
collected
Cameroon
Ngoupayo et al.
(2008)
Cameroon
Ngoupayo et al.
(2008)
Waffo et al.
(2006)
Lannang et al.
Cameroon
(2008)
Momo et al.
Cameroon
(2011)
Cameroon
G. lucida
Stem bark
β-Sitosterol-glucopyran
G. lucida
oside (111)
Stem bark
Cameroon Fotie et al. (2007)
Stigmasterol (112)
G. nervosa
Dried leaf
Nigeria
G. lucida
Stem bark
Conrauanalactone (113) G. conrauana
Stem bark,
leaf, seed
3-(3’’,3’’-Dimethylallyl
Stem bark,
)-conrauanalactone
G. conrauana
leaf, seed
(114)
5,7-Dihydroxychromon
Stem bark,
G. conrauana
e (115)
leaf, seed
3α-Hydroxy-5-(heptade
c-8’-enyl)-tetrahydrofur G. mannii
Stem bark
an-2-one (116)
Garcifuran A (117)
Parveen et al.
(2004)
Momo et al.
Cameroon
(2011)
Hussain and
Cameroon
Waterman (1982)
Cameroon
Hussain and
Waterman (1982)
Cameroon
Hussain and
Waterman (1982)
Cameroon
Hussain and
Waterman (1982)
Niwa et al.
(1994a)
Terashima et al.
(1999b)
Niwa et al.
(1994a)
Terashima et al.
(1997)
Terashima et al.
(1997)
Niwa et al.
(1994b)
Niwa et al.
(1994b)
G. kola
Dried root
Nigeria
G. kola
Dried stem
Nigeria
Garcifuran B (118)
G. kola
Dried root
Nigeria
Garcinal (25)
G. kola
Dried seed
Nigeria
Garcinoic acid (26)
G. kola
Dried seed
Nigeria
Garcipyran (119)
G. kola
Dried root
Nigeria
Dried root
Nigeria
Stem bark
Cameroon Fotie et al. (2007)
Stem bark
Cameroon Fotie et al. (2007)
2,4-Dimethoxy-6-hydro
G. kola
xyacetophenone (120)
Dihydrochelerythrine
G. lucida
(48)
6-Acetonyldihydrochel
G. lucida
erythrine (49)
Chapter 4 Phytochemistry of African Garcinia Plants
Class
Where
collected
Cameroon
DR
Congo
DR
Congo
DR
Congo
DR
Congo
DR
Congo
DR
Congo
DR
Congo
DR
Congo
DR
Congo
DR
Congo
DR
Congo
DR
Congo
Name
Plant species Part
Lucidamine A (50)
G. lucida
Stem bark
Damnacanthal (20)
G. huillensis
Root bark
Nordamacanthal (121) G. huillensis
Root bark
2-Formyl-1-hydroxyant
G. huillensis
hraquinone (122)
Root bark
Lucidin (123)
G. huillensis
Root bark
G. huillensis
Root bark
G. huillensis
Root bark
G. huillensis
Root bark
Rubiadin (127)
G. huillensis
Root bark
Rubiadin 3-methyl
ether (128)
G. huillensis
Root bark
Tectoquinone (129)
G. huillensis
Root bark
Rubiadin dimethyl
ether (130)
G. huillensis
Root bark
Pachybasin (131)
G. huillensis
Root bark
δ-Tocotrienol (132)
G. kola
Seed
Nigeria
G. lucida
Stem bark
Cameroon
G. lucida
Stem bark
Cameroon
G. lucida
Stem bark
Cameroon
G. lucida
G. lucida
Stem bark
Stem bark
Cameroon
Cameroon
Lucidin 1,3-dimethyl
ether (124)
Damnacanthol
1-methyl ether (125)
Rubiadin 1-methyl
ether (126)
30-Hydroxycycloarteno
l (133)
31-Norcycloartenol
(134)
24,25-Epoxy-31-norcyc
loartenol (135)
Sesamin (136)
Trans-fagaramide (137)
85
Reference
Fotie et al. (2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Dibwe et al.
(2007)
Terashima et al.
(1997)
Nyemba et al.
(1990)
Nyemba et al.
(1990)
Nyemba et al.
(1990)
Fotie et al. (2007)
Fotie et al. (2007)
4.2 Benzophenones
Plants of the genus Garcinia, produce a series of oxidized and isoprenylated
benzophenones that are believed to originate from the mixed shikimate and
acetate biosynthetic pathways (Beerhues and Liu, 2009). Many benzophenone
compounds from the genus Garcinia contains the cyclohexatrione moiety,
86
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
which is generated by incorporation of several isoprenyl groups into C-2 and
C-4 of a 1,3,5-trihydroxybenzophenone to form a bicyclo[3.3.1]nonane. This
type of bridged polycyclic skeletons is widely distributed in the genus Garcinia
and they are associated with a wide range of biological and pharmacological
activities. Thus, the benzophenone derivatives can be regarded as useful
candidates for drug development.
Phytochemical reports from Garcinia plants of African origin revealed the
isolation of many polyisoprenylated benzophenones. Currently, there are about
nine benzophenone compounds reported from nine African Garcinia plants
(Table 5). Hence, garcinol (51), a polyisoprenylated benzophenone derivative
isolated from the stem bark of G. huillensis (Bakana et al., 1987), has been
reported to possess antioxidative (Yamaguchi et al., 2000) and anti-HIV
(Gustafson et al., 1992) activities. Recently, garcinol has been reported as a
pleiotropic agent capable of modulating key regulatory cell signaling pathways
as well as an anti-cancer agent (Padhye et al., 2009).
In another study, three novel polyprenylated benzophenones, named
semsinones A-C (53-55), have been isolated from a Tanzanian plant, Garcinia
semseii (Magadula et al., 2008). Other benzophenones are xanthochymol (52),
guttiferones A (36) and E (57), isoxanthochymol (13) and kolanone (58) being
isolated from G. staudtii (Waterman & Hussain, 1982), G. livingstoneii, G.
ovalifolia, G. polyantha (Gustafson et al., 1992) and G. kola (Iwu et al., 1990),
respectively.
4.2 Flavonoids
Flavonoids are polyphenols and water-soluble compounds that are known to
be beneficial to human health (Iriti and Varoni, 2013). They are synthesized by
the phenylpropanoid metabolic pathway in which the amino acid phenylalanine
Chapter 4 Phytochemistry of African Garcinia Plants
87
is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA
to yield the true backbone of flavonoids (Ververidis et al., 2007). Flavonoids
are consumed by many animals including humans in their diets, due to their
well known low toxicity compared to other active plants secondary metabolites
like alkaloids. They have also been reported in some other studies to be
biologically
effective
as
"response
modifiers",
showing
anti-allergic,
antioxidant, anti-inflammatory activities (Cushnie and Lamb, 2005).
In Garcinia plants, flavonoids and their derivatives are considered as the
main components. More than 30 flavonoids have been isolated from Garcinia
species found in Africa. These include flavones, flavanones, biflavanones,
flavonols and flavonoid glycosides (Table 5). From the root bark of African
mangosteen cultivated in Tanzania, two flavanones, namely volkensiflavone (67)
and morelloflavone (68), were isolated (Mbwambo et al., 2006), while from G.
kola, the most studied African Garcinia plant, about 25 flavonoids were
reported by different researchers (Table 5). For instance, biflavanoids such as
Garcinia biflavanone GB-1 (3), Garcinia biflavanone GB-2 (24), were reported
to be dominant in the dried seeds of G. kola (Okunji and Iwu, 1991; Iwu and
Igboko, 1982; Madubunyi, 1995; Kapadia et al., 1994). Several other flavonoids
isolated from African Garcinia species have been reported in the literature
(Table 5).
4.3 Triterpenoids
Triterpenoids belong to a large and structurally diverse class of naturally
occurring organic compounds which are distributed throughout the plant
kingdom. They are commonly found in higher plants, lower animals
(anthropods, coelenterates and molluscs), fungi, lichens and algae (Leistner,
2000). This class of compounds comprises natural products which are derived
88
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
from a common biosynthetic pathway based on mevalonate as parent, with a
configuration of 30 carbons and several oxygens attached. Triterpenoids have
been reported to have a wide spectrum of biological activities including
cytotoxic, fungicidal, antiviral, analgesic, cardioprotective, spermicidal and
anticancer properties (Lee, et al., 1988).
From African Garcinia plants, only nine (9) triterpenoids have been reported
(Table 5). These include friedelin (80), isolated from the stem bark of G.
ovalifolia (Waterman et al., 1980), G. polyantha (Lannang et al., 2005) and G.
edulis (Magadula, 2010). Other pentacyclic triterpenoids, oleanoic acid (81) and
lupeol (82) were isolated from the stem barks of G. polyantha (Lannang et al.,
2005), while, from the root bark of G. edulis, lupeol was isolated together with
its acetate (84) (Magadula, 2010). In another study from G. semseii, a plant
which is endemic to Tanzania, a monocyclic triterpene, achilleol A (83) was
reported from its stem bark (Magadula et al., 2008). Other triterpenoids isolated
from African Garcinia plants are indicated in Table 5.
4.4 Xanthones
Xanthones are secondary metabolites whose basic structure is always flanked
with a variety of oxygenated and prenylated groups, being reported to occur in
some genera of higher plants including Garcinia. The diverse substitution
patterns of xanthones provide a good basis for different biological activity and
also for structure-activity relationship studies (Ee at al., 2005). Natural
xanthones can be subdivided, based on the nature of substituents, into simple
oxygenated xanthones, glycosylated xanthones, prenylated xanthones and their
derivatives, xanthone dimers, xanthonolignoids and miscellaneous (Pinto et al.,
2005). Currently, over 200 xanthones have been identified worldwide (Obolskiy
et al., 2009; Peres and Nagem, 1997). Extensive phytochemical investigations
Chapter 4 Phytochemistry of African Garcinia Plants
89
from the genus Garcinia gave a variety of prenylated xanthones, some of them
exhibited a wide range of biological and pharmacological activities, including
cytotoxic, antimicrobial, antifungal, antioxidant, antimalarial, anti-HIV-1,
anti-obesity and anti-parasitic activities (Minami et al., 1994). Many of these
xanthones are found in the pericarp of the true mangosteen fruit, G. mangostana,
which is a highly investigated plant in the genus Garcinia (Obolskiy et al.,
2009).
African Garcinia plants were reported to possess a long list of xanthones
(Table 5). About 35 different types of xanthones have been reported, most of
them from Garcinia plants collected in Cameroon, Nigeria, South Africa and
Tanzania (Table 5). A phytochemical report from an African mangosteen (G.
livingstoneii) gave 11 xanthones (Mbwambo et al., 2006; Sordat-Diserens et al.,
1992) while, from a South African plant, G. gerrardii, garcigerrin A (4) and B
(5) were isolated (Sordat-Diserens et al., 1989). From Cameroon, Waffo and
co-workers investigated the stem bark of G. afzelii, from which two xanthones,
afzeliixanthone A (21) and B (22) were isolated (Waffo et al., 2006). From
Nigeria, rheediaxanthone (91) and rheediaxanthone A (92) were isolated from
the stem bark of G. staudtii (Waterman and Hussain, 1982). Table 5 provides
the whole list of xanthones isolated from African Garcinia plant species.
4.5 Other Compounds
Apart from the the 4 classes of compounds mentioned above, a range of other
compounds have also isolated from Garcinia plants. These include
brevipsidones (44-47) previously isolated from the stem bark of a Cameroonian
plant, G. brevipedicellata (Ngoupayo et al., 2008), and conrauanalactones
(113-114) isolated from the stem bark, leaves and seeds of G. conrauana
(Hussain and Waterman, 1982). Furthermore, garcifurans (116-119) were
90
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
isolated from G. kola (Niwa et al., 1994; Terashima et al., 1999) while the
commonly known phytosterols, stigmasterol (110) and β-sitosterol (112) were
also reported from many other Garcinia species growing in Africa (Table 5).
OH
OH
HO
O
O
O
HO
O
OH
O
OH
52
51
OH
OH
HO
O
HO
O
R
O
HO
O
O
O
53
O
54
R
H
55
OH
O
OH
HO
OH
OH
HO
O
56
O
O
HO
O
O
O
O
OH
OH
57
58
Fig. 21. Structures of compounds isolated from African Garcinia plants.
Chapter 4 Phytochemistry of African Garcinia Plants
OH
OH
OH
HO
O
OH
OH
O
HO
O+
HO
OH
O
OH
HO
O
R
H
R 59
R'
OH
O
OH
R'
H
OH
OH
60
H
OH
61
OH
H
O
63
62
OH
OH
HO
HO
O
O
OCH3
HO
R
OH
91
O
O
OH
OH
R
64 H
65 OCH3
66 glc
O
HO
OH
O
O
OH
HO
OH
O
O
69
OH
OH
O
70
67 H
68 OH
OH
HO
R7
O
R2
O
R3
R1
OH
HO
OH
OH
O
O
O
73 H
OH
O
OH
72
OH
HO
O
R2
R3
R4
R5
OCH3
H
OH
OCH3
74 OCH3
H
OH OCH3
75 OCH3
H
H
O
R7
OCH3
H
OH
H
H
OCH3
OH
OH
HO
O
OH
HO
O
OH
O
77
OH
OH
HO
O
OH
OH
OH
O
HO
O
O
OH
OH
OH
OH
OH
76
OH
R6
OCH3 OH
O
HO
OH
R4
R5
R1
O
71
R6
OH
HO
OH
O
OH
O
78
OH
O
79
Fig. 21. Structures of compounds isolated from African Garcinia plants (Cont).
92
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
H
H
H
H
H
H
COOH
H
H
O
HO
80
HO
H
H
82
81
H
HO
H
H
H3COO
H
83
84
H
HO
H
OH
H
H
H3COO
H
85
H
COOH
H
HO
H
86
COOH
H
HO
H
87
H
O
OR
88
89
R
H
CH3
Fig. 21. Structures of compounds isolated from African Garcinia plants (Cont).
Chapter 4 Phytochemistry of African Garcinia Plants
O
OH
OH
O
OH
93
O
O
O
OH
O
OH
O
OH
90
O
91
OH
O
OH
92
OH
O
OH
O
O
OH
O
O
OH
O
O
94
93
OH
OH
OH
O
O
OH
OH
O
OH
OH
98
97
O
O
OH
O
O
O
OH
O
O
96
OH
OH
95
OH
O
OH
HO
OH
O
O
HO
O
OH
OH
O
OH
OCH3
O
OH
OH
OH
O
101
OH
99
100
OH
O
O
OH
O
OH
O
O
O
OH
102
O
HO
O
OH
103
OH
OH
OCH3
OH
O
104
Fig. 21. Structures of compounds isolated from African Garcinia plants (Cont).
94
Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
O
OH
O
OH
OH
O
HO
O
OH
HO
O
OCH3
O
OH
HO
OH
OH
OH
106
107
105
O
O
H
OH
OH
H
OCH3
OH
H
O
109
108
H
HO
O
110
OH
R
H
H
H
H
H
C14H29
O
H
H
H
O
113
R
H
HO
Glc
112
111
HO
O
OH
O
HO
HO
O
114
O
(CH2)6CH=CH(CH2)7CH3
OH
H3CO
O
116
115
117
Fig. 21. Structures of compounds isolated from African Garcinia plants (Cont).
Chapter 4 Phytochemistry of African Garcinia Plants
O
O
OCH3
HO
OH
HO
OCH3
HO
H3CO
HO
OCH3
OH
O
119
118
120
R1
O
R1
O
CHO
CH2OH
R2
O
OCH3
20
121 OH
122 H
R1
O
CH3
R2
O
R1
R1
R2
OH
123 OH
OH
124 OCH3
H
125 OCH3
R2
OH
OCH3
OH
R2
O
O
R1
126
OCH3
127
OH
128 H
129 OH
R2
OH
OH
OCH3
O
CH3
OCH3
O
H
OCH3
OH
O
130
131
HO
O
CH3
132
HO
H
HO
H
OH
133
134
O
O
HO
O
O
H
135
O
O
O
O
N
H
O
O
136
137
Fig. 21. Structures of compounds isolated from African Garcinia plants (Cont).
95
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Appendix List of African Garcinia Species-Countrywise
S/N Garcinia species
Author
Country where found
1
G. acutifolia
N. Robson
2
G. afzelii
Engl.
Tanzania, Mozambique
Ghana, Guinea, Togo, Cameroon,
Nigeria
3
G. ambrensis
4
G. anjouanensis
5
G. aphanophlebia
6
G. arenicola
7
G. asterandra
8
G. bifasculata
G.
brevipedicellata
N. Robson
Tanzania
(Bak. f.) Hutch. & Dalz
Cameroon, Nigeria
10
G. buchananii
Bak.
11
G. buchneri
12
G. calcicola
13
G. capuronii
Engl.
(Jumelle & H. Perrier) P.
Sweeney & Z. S. Rogers
Z. S. Rogers & P. Sweeney
14
G. cerasifer
15
G. chapelieri
16
G. chromocarpa
(H. Perrier) P. F. Stevens
(Planchon & Triana) H.
Perrier
Engl.
17
G. commersonii
(Planchon & Triana) Vesque Madagascar
18
G. conrauana
Engl.
Cameroon
19
G. crassiflora
Madagascar
20
G. dalleizettei
21
G. dauphinensis
Jumelle & H. Perrier
(H. Perrier) P. Sweeney &
Z. S. Rogers
P. Sweeney & Z. S. Rogers
22
G. decipiens
(Baillon) Vesque
Madagascar
23
G. disepala
Vesque
Madagascar
24
G. densivenia
Engl.
Cameroon
25
G. edulis *
Exell
Tanzania
26
G. epunctata
Stapf
Guinea, Ghana, Cameroon
27
G. ferrea *
Pierre
Tanzania
9
(H. Perrier) P. Sweeney &
Z.
S. Rogers
(H. Perrier) P. Sweeney &
Z. S. Rogers
Baker
(Jumelle & H. Perrier) P.
Sweeney & Z. S. Rogers
Jumelle & H. Perrier
Madagascar
Madagascar
Madagascar
Madagascar
Madagascar
Tanzania, Uganda, Kenya, Zimbabwe,
Mozambique, Ethiopia
Zambia
Madagascar
Madagascar
Madagascar
Madagascar
Cameroon
Madagascar
Madagascar
110
Appendix List of African Garcinia Species-Countrywise
28
G. gerradii
Harvey
29
G. huillensis
Welw. ex Oliv.
30
G. indica*
DC.
31
G. kingaensis
Engl.
32
G. kola
Heckel
33
G. livingstonei
T. Anderson
34
G. lucida
Vesque
South Africa
DR Congo, Mozambique, Tanzania,
Zambia, Zimbabwe, Cameroon,
Malawi, Ethiopia
Tanzania (Zanzibar)
Tanzania, Zambia, Zimbabwe,
Mozambique
Nigeria, Ghana, Cameroon, Ivory
Coast, Guinea, DR Congo,
South Africa, Tanzania, Kenya,
Uganda, Somalia, Zambia, Zimbabwe,
Mozambique, DR Congo, Madagascar,
Ethiopia
Cameroon
35
G. lowryi
G.
madagascariensis
Z. S. Rogers & P. Sweeney
Madagascar
(Planchon & Triana) Pierre
Madagascar
36
37
G. mangorensis
38
G. mangostana*
(R. Viguier & Humbert) P.
Sweeney & Z. S. Rogers
L.
39
G. megistophylla
P. Sweeney & Z. S. Rogers
Madagascar
40
G. melleri
Madagascar
41
G. multifida
42
G. mannii
Baker
(H. Perrier) P. Sweeney &
Z. S. Rogers
Oliv.
43
G. nervosa
Miq., P. Sweeney
Nigeria
44
G. orthoclada
Baker
Madagascar
45
G. ovalifolia
Oliv.
Cameroon, CAR, Togo
46
G. pachyclada
Tanzania, Zambia
47
G. parvula
48
G. pauciflora
N. Robison
(H. Perrier) P. Sweeney &
Z. S. Rogers
Baker
49
G. pervillei
(Planchon & Triana) Vesque Madagascar
50
G. polyantha
Oliv.
Cameroon, Togo,
51
G. polyphlebia
Baker
Madagascar
52
G. punctata
Oliv.
Gabon, Zambia
53
G. quadrifaria
(Oliv.) Baill. ex Pierre
Cameroon
54
G. semseii
Verdc
Tanzania
55
G. smeathmannii
(Planch&Triana) Oliv.
Cameroon, Tanzania
56
G. staudtii
Nigeria, Cameroon,
57
G. thouvenotii
Engl.
(H. Perrier) P. Sweeney &
Z. S. Rogers
Madagascar
Tanzania, Madagascar
Madagascar
Cameroon,
Madagascar
Madagascar
Madagascar
Appendix List of African Garcinia Species-Countrywise
(H. Perrier) P. Sweeney &
Z. S. Rogers
P. Sweeney & Z. S. Rogers
(H. Perrier) P. Sweeney &
Z. S. Rogers
58
G. tsaratananensis
59
G. tsimatimia
60
G. urschii
61
G. verrucosa ssp
orientalis
H. Perrier
Madagascar
62
G. volkensii
Engl.
Kenya, Malawi, Mozambique,
Tanzania, Zambia, Zimbabwe
63
G. xanthochymus
*
Roxb. T. Anders
Tanzania
*Exotic species.
Madagascar
Madagascar
Madagascar
111
Joseph Jangu Magadula was born in Magu district,
Mwanza region, Tanzania. He received his BSc degree in
Physics and Chemistry in 1997 at the University of Dar es
Salaam, Tanzania. He then enrolled for an MSc degree in
Chemistry at the same University, graduating in 2000. In
2003 he joined the University of KwaZulu-Natal, South
Africa, receiving his PhD in PhytoChemistry in May
2006. He is now holding a position of Senior Research
Fellow and serving as head of department of Natural
Products Development and Formulations, Chairperson of
NAPRECA (Tanzania) and Editor-in Chief of the ITM
News Bulletin.
Zakaria Heriel Mbwambo was born in Mamba-Ivuga,
Same district, Kilimanjaro region, Tanzania. He received
his MSc in Pharmacy at the Kharkov State Pharmaceutical
Institute, Ukraine in 1984. He was then enrolled as a PhD
candidate in 1991 at the University of Illinois at Chicago
in the USA specializing in the Chemistry of Natural
Products where he graduated in 1996. He was holding a
position of Associate Research Professor until his death
from brain tumor in July 2014.
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