The Value-Added Uses of Ficus Retusa and Dalbergia Sissoo

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J OURNAL OF FOREST PRODUCTS & INDUSTRIES, 2013, 2(3), 34-41 ISSN:2325–4513(PRINT) ISSN 2325 - 453X (ONLINE )
RESEARCH ARTICLE 34
The Value-Added Uses of Ficus Retusa and Dalbergia
Sissoo Grown in Egypt: GC/MS Analysis of Extracts
Hussein I.M. Aly1, Abdel B. El-Sayed1, Yousry M. Gohar2, Mohamed Z.M. Salem1*
1
Forestry and Wood Technology Department, Faculty of Agriculture (EL-Shatby),
Alexandria University, Egypt
2
Department of Botany (Division of Microbiology), Faculty of Science (ElShatby), Alexandria University, Egypt
(Received March 22, 2013; Accepted April 26, 2013)

Abstract— In the present study the ethyl acetate fractions from the
methanol extract of Ficus retusa leaves and Dalbergia sissoo wood
was analyzed by means of GC/MS. The main compounds presence
in the ethyl acetate fraction from the leaves of F. retusa, were
1,2-benzenedicarboxylic
acid-dibutyl
ester
(15.19%),
phenol,4-(2-aminopropyl)-, (+/-) (9.27%) and R-(2,2,3,3-2H4)
butyrolactone (13.24%). The main components presented in the
ethyl acetate fraction from wood of D. sissoo, were
acid
dibutyl
ester
(13.68%),
5-Nirto-2,4(1H,3H)-pyrimidinedione
(7.94%),
3-hydroxycarbonyl-2,5-diethylpyrrolidine (7.83%) and formic
acid, 1-methylethyl ester (7.38%). It was noted that the
1,2-benzenedicarboxylic acid dibutyl ester found in the ethyl
acetate fraction from the leaves of F. retusa and wood of D. sissoo.
Index Terms— Ficus retusa, Dalbergia sissoo, GC/MS,
Extracts, Leaves, Wood
I. INTRODUCTION
n Egypt, there are many kinds of tree species planted as street
trees, windbreaks and shelterbelts and there are large
quantities of wood branches and leaves resulted annually
from the pruning process to street trees such as Ficus species
and ornamental trees. Therefore, these materials can be used as
a useful source for the production of phytochemical substances.
I
Ficus is a genus of about 800 species and 2000 varieties belongs
to family Moraceae occurring in tropical and subtropical forests
[1]. Studies on Phytochemical analysis of some Ficus species
revealed the presence of phenolic compounds as the major
components [2,3,4,5]. Ficus retusa L. (F. nitida Thunb.) or (F.
microcarpa L.) commonly known as Chinese anyan is a large
evergreen tree and distributed throughout Central India and
Australia. Previously it have been reported that the aerial part of
F. retusa had a cytotoxic
and antifungal activities [6,7]. Additionally, the golden yellow
leaves was found to have a high amounts of
*Corresponding author ([email protected])
flavonoids, carotenoids, triterpenoids, fatty alcohol, steroids,
coumarins, flavane-4-hydroxybenzoate and isoflavones
[8,9,10]. Mahmoud et al. [11] found a significant inhibitory
activity when F. nitida mixed with virus inoculum or applied 48
h before challenge.
Dalbergia sissoo Roxb. belongs to family: Fabaceae is
commonly known as Indian rosewood [12]. The extract was
found to possess antidysentric [13], analgesics and antipyretic
[14]. The bark and extracts of wood are bitter used as
aphrodisiac, abortifacient, expectorant, antihelmintic and
antipyretic [15]. The phytochemical analysis of D. sissoo
reported the presence of alkaloids, carbohydrates, saponins,
flavonoids, glycosides and steroids [12,15,16]. The extracts
from stem bark have been reported to have a good antioxidant
activity [17].
From the previous study [18] it was reported that the extracts
from F. retusa and D. sissoo had a good antibacterial activity, so
that the present study showing the GC/MS analysis of ethyl
acetate fractions from the methanol extract of wood and leaves
from D. sissoo and F. retusa, respectively.
II. MATERIALS AND METHODS
Tree material
From the previous study [18], the wood and leaves of F. retusa
and D. sissoo, respectively, were collected from different
locations at Alexandria City, Egypt. Plant vouchers were kindly
identified and stored for deposition at the Department of
Forestry and Wood Technology, Faculty of Agriculture,
Alexandria University.
Preparation of extracts
The different parts were air-dried under room temperature,
ground to fine powder, placed on polyethylene bags and kept
away from moisture in a dried place until use [19]. Powdered
plant materials (50 g) was extracted with 500 mL of methanol
(80%) for 8 h using Soxhlet extractor apparatus at 40°C and the
35
solvent was evaporated under reduced pressure. The extracts
at 4°C until use. The methanol extract from each part was
subsequent partitioned using separating-funnel into ethyl
acetate, n-butanol and water. These fractions were separated
with solvent/solvent group separation procedure [18,20]. The
quantification of methanol extract and ethyl acetate fraction
from F. retusa leaves and D. sissoo wood was (60.52, 4.22 g/kg
o.d.) and (43.19, 6.59 g/kg o.d.), respectively.
Chemical Constituents of Fractionated Extracts by Gas
Liquid Chromatography/Mass Spectrometry (GC-MS)
Apparatus
Accordingly, identification of the chemical constituents of
fractionated extracts were made using HB5890 gas liquid
chromatography (GLC) coupled with HB5890B series mass
spectrometer (MS) at Central Lab. Unit in High Institute of
Public Health, Alexandria, Egypt. The gas liquid
chromatography was equipped with a split less injector at 280ºC,
and a flame ionization detector (FID) held at 300°C using
helium as a carrier gas. Samples were separated on a capillary
column (30m long, and 0.25mm internal diameter) HP-5
(Avondale, PA, USA) of 0.25μm film thickness. The
temperature of the gas chromatograph column was programmed
from 80°C to 100°C at a heating rate of 15°C /minute, and then
increased to a maximum final temperature of 310°C at a heating
rate of 5ºC/minute, holding the maximum final temperature for a
residence time of 10 minutes. The temperature of ion source in
the mass spectrometer was held at 200°C. All mass spectra were
recorded in the electron impact ionization (EI) at 70 electron
volts. The mass spectrometer was scanned from m/z 40 to 410 at
a rate of two scans per second. An integrator automatically
calculated peaks areas. Neither internal nor external chemical
standers were used in this chromatographic analysis.
were lyophilized, weighed and stocked in sealed vials
Interpretation the resultant mass spectra were made using a
computerized library searching program, and by studying the
fragmentation pattern of such compound resulted from mass
spectrometry analysis.
III. RESULTS AND DISCUSSION
Suggested chemical components found in the ethyl acetate
fraction extracted from F. retusa leaves
F. retusa is a widely distribution tree in streets and roads of
Alexandria, moreover, there are large quantitative of leaves
resulted annually from pruning process that can be used in
various purposes. The chemical composition of the ethyl acetate
fraction derived from the methanolic extract from F. retusa
leaves, which had 19 organic compounds, were identified by
means of GC-MS method. Figure 1 showed the chromatogram
chart of these chemical components found in the ethyl acetate
fraction. Table 1 presented the characterizations (compound
name, retention time, chemical formula, molecular weight and
the peak area or yield of the components) of the chemical
composition of this fraction.
The main compounds presence in the ethyl acetate fraction from
the leaves of F. retusa, were 1,2-benzenedicarboxylic
acid-dibutyl ester (15.19%); this component was found to have
a good antibacterial activity against certain Gram-positive and
Gram-negative bacteria [21], phenol,4-(2-aminopropyl)-, (+/-)
(9.27%) and R-(2,2,3,3-2H4) butyrolactone (13.24%).
Furthermore, the mass spectra (MS) and chemical structures for
these compounds were showed in Figures 2, 3 and 4 with the
molecular weight (MW) 278, 90, and 151 respectively.
Figure 1: Chromatogram of chemical components presents in ethyl acetate fraction extracted from F. retusa leaves.
36
Figure 2: Mass Spectrum of 1,2-benzenedicarboxylic acid, dibutyl ester from ethyl acetate fraction from F. retusa leaves.
Figure 3: Mass Spectrum of phenol, 4-(2-aminopropyl) (+/-) from ethyl acetate fraction extracted from F. retusa leaves.
37
Figure 4: Mass spectrum of R-(2,2,3,3-2H4) butyrolactone from ethyl acetate fraction extracted from F. retusa leaves.
Table 1
Suggested chemical compounds present in ethyl acetate fraction extracted from F. retusa leaves by using GC-MS
Compound
Retention time (min)
Formula
MWA Concentration %B
Measured Authentic
2-methylaminoethyl-1,3-dioxolane
3.33
3.35
C5H11NO2
117
2.25
R-(2,2,3,3-2H4) butyrolactone
3.61
3.61
C4H2D4O2
90
13.24
trans-3,5-dideutero hydroxy cyclopentene 3.97
3.97
C5H6D2O2
102
3.49
1-methyldecylamine
4.65
4.65
C11H25N
171
3.97
n-pentanal
5.14
5.14
C5H10O
86
2.38
phenol,4-(2-aminopropyl) (+/-)
5.73
5.74
C9H13NO
151
9.27
oxaluric acid
6.23
6.24
C3H4N2O4
132
2.70
4-Methyl-2-hexanamine
6.78
6.77
C7H17N
115
3.17
cyclobutanol
8.17
8.16
C4H8O
72
5.35
acetaldehyde
8.29
8.30
C2H4O
44
1.33
guanosine
8.44
8.43
C10H13N5O5 283
2.69
2,6-dimethyl-4H-pyran-4-one
8.53
8.52
C7H8O2
124
2.60
2,2-dimethyl-4-methylaminobutanone
9.38
9.37
C7H15NO
129
7.45
1,2-benzenedicarboxylic acid,
9.47
9.46
C16H22O4
278
15.19
dibutylester
butethamate probe product
9.76
9.76
C16H25NO2
263
3.17
N,2-dimethyldodecylamine
10.14
10.14
C14H31N
213
4.56
2-octanamine
10.56
10.56
C8H19N
129
4.51
2-flluoro-beta benzeneethanamine,
11.36
11.37
C9H12FNO2 185
2.16
5-dihydroxy-N-methyl
cyclopentanedecol
11.52
11.53
C5H10O10
230
1.90
(A): Molecular weight of the compound (g/mol).
(B): Based on total areas of the identified peaks.
38
Recent study reported that the new polyphenolic compounds
named
retusaphenol
[2-hydroxy-4-methoxy-1,3-phenylene-bis-(4-hydroxy-benzoate
)]
and
(+)-retusa
afzelechin
[afzelechin-(4α→8)-afzelechin-(4α→8)-afzelechin] together
with ten known compounds: luteolin,(+)- afzelechin,
(+)-catechin, vitexin, ß-sitosterol acetate, ß-amyrin acetate,
moretenone, friedelenol, ß-amyrin and ß-sitosterol were
isolated for the first time from the ethanolic extract of the aerial
parts of F. retusa L."variegata" [22]. Previously [18], the tested
extracts from F. retusa had a variable degree of antibacterial
activity against all of the tested bacteria. However, the leaves
methanol extract had the highest activity against the growth of
selected bacteria at the lower concentrations. Furthermore, the
methanol extract from wood and bark was observed to have
good activity against the tested bacteria except E. coli more than
other tested bacteria. The chloroform and water fractions from
wood showed good activity against tested bacteria at low
concentrations.
Suggested chemical components found in the ethyl acetate
fraction extracted from D. sissoo wood
The ethyl acetate fraction from the wood of D. sissoo was
showed good antibacterial activity against the growth of tested
bacteria. The chemical components presences in this fraction
were 20 organic components, showed in Figure 5 and Table 2.
The main components from the analysis of this fraction, were
1,2-benzenedicarboxylic acid dibutyl ester (13.68%) and
5-nirto-2,4(1H,3H)-pyrimidinedione (7.94%), this component
was showed antibacterial activity against Staphylococcus
aureus and Bacillus cereus (as a Gram-positive strains),
Serratia marcescens and Proteus mirabilis (as a Gram-negative
strains),
by
disc
diffusion
method
[23],
acid, 1-methylethyl ester (7.38%). the MS and chemical
structures of the compounds were shown in Figures 2, 6 and 7
with the molecular weight (MW) 278, 157, and 88 g/mol for
acid
dibutyl
ester,
5-nirto-2,4(1H,3H)-pyrimidinedione and
formic acid,
1-methylethyl ester, respectively. It was noted that the
1,2-benzenedicarboxylic acid dibutyl ester showed in the ethyl
acetate fraction from the leaves of F. retusa.
Figure 5. Chromatogram of chemical components presents in ethyl acetate fraction extracted from D. sissoo wood.
39
Figure 6: Mass spectrum of 5-nitro-2, 4(1H, 3H)-Pyrimidinedione from the ethyl acetate fraction extracted from D. sissoo
wood.
Figure 7: Mass spectrum of formic acid,1-methylethyl ester from ethyl acetate fraction extracted from D. sissoo wood.
IV. CONCLUSION
The main compounds presence in the ethyl acetate fraction from
the leaves of F. retusa, were 1,2-benzenedicarboxylic
acid-dibutyl ester (15.19%), phenol,4-(2-aminopropyl)-, (+/-)
(9.27%) and R-(2,2,3,3-2H4) butyrolactone (13.24%). The main
components presented in the ethyl acetate fraction from wood of
D. sissoo, were 1,2-benzenedicarboxylic acid dibutyl
ester (13.68%), 5-Nirto-2,4(1H,3H)-pyrimidinedione (7.94%),
acid, 1-methylethyl ester (7.38%). The analysis of extracts from
Ficus retusa leaves and Dalbergia sissoo wood might be of
great value for pharmaceutical industry. Indeed further work
should be done to elucidate main chemical compounds
responsible for the activity and its valuable for human and plant
health.
40
Table 2
Suggested chemical compounds present in ethyl acetate fraction extracted from D. sissoo wood by using GC-MS.
Compound
Retention time (min)
Measured Authentic
R-(2,2,3,3-2H4)Butyrolactone
3.33
3.32
Formic acid,1-methylethyl ester
3.66
3.66
Propene 3,3,3-D3
3.76
3.75
2-Propanamine
3.96
3.97
2-Amino-1-propanol
4.61
4.60
Pentanal
5.29
5.30
Guanosine
5.36
5.36
Acetaldehyde
5.73
5.74
Cyclobutanol
6.41
6.42
3-Amino-2-ethylbutanoic acid
7.40
7.40
2-Oxo-Butanoic acid
7.64
7.63
Benzenemethanol, 2-2-aminopropoxy
8.20
8.21
2-Fluoro-betahydroxy benzeneethanamine
8.53
8.52
L-Alanine, methyl ester
9.16
9.15
3-Hydroxycarbonyl-2,5-diethylpyrrolidine
9.40
9.39
1,2-Benzenedicarboxylic acid dibutyl ester 9.47
9.46
2,2-Dimethyl-4-methylaminobutanone
10.20
10.20
5-Nirto,2,4-Pyrimidinedione
10.51
10.52
2-Isocyanato-Propane
10.69
10.70
Oxirane
11.72
11.73
(A): Molecular weight of the compound (g/mol).
(B): Based on total areas of the identified peaks.
Formula
MWA
Concentration %B
C4H2D4O2
C4H8O2
C3H3D3
C3H9N
C3H9NO
C5H10O
C10H13N5O5
C2H4O
C4H8O
C6H12NO2
C4H6O3
C11H17NO2
C9H12FNO2
C4H9NO2
C7H13NO2
C16H22O4
C7H15NO
C4H3N3O4
C4H7NO
C2H4O
90
88
45
59
75
86
283
44
72
131
102
195
185
103
143
278
129
157
85
44
3.58
7.38
4.22
3.03
1.71
2.29
2.02
1.47
0.47
2.63
1.49
7.29
1.00
1.49
7.83
13.68
5.27
7.94
6.56
1.98
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The Value-Added Uses of Ficus Retusa and Dalbergia Sissoo

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