Obtenciyn de extractos fenylicos a partir de subproductos de la oliva

Transcription

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Resumen
Existe una evidencia creciente de los beneficios del consumo de aceite de oliva en
la prevención de enfermedades asociadas al estrés oxidativo, el cual es responsable en
gran medida de la generación de problemas cardiovasculares, cáncer y enfermedades
neurodegenerativas. Aunque este efecto reductor del riesgo cardiovascular se ha
atribuido tradicionalmente a la composición de ácidos grasos del aceite de oliva (alto
contenido de ácido oleico), estudios más recientes han evidenciado el papel de su
fracción fenólica en la prevención de este tipo de enfermedades relacionadas con el
estrés oxidativo. Algunos estudios “in vivo” han mostrado el efecto de la ingesta de
aceite de oliva virgen en la reducción de algunos marcadores de oxidación. Sin
embargo, la magnitud de la mejora conseguida es modesta para afirmar su valor
predictivo como factor de protección de riesgo cardiovascular. Esto es explicable por
la limitada cantidad de compuestos fenólicos que se ingieren y finalmente son
absorbidos por el organismo a través de la dosis diaria de aceite de oliva virgen en la
dieta Mediterránea (aproximadamente de 25 a 50 mL de aceite de oliva que aportan de
3 a 15 mg de compuestos fenólicos al día). En esta línea, la principal aportación de la
presente tesis doctoral reside en el desarrollo de un aceite de oliva virgen enriquecido
con sus propios compuestos fenólicos, incrementando así su ingesta diaria y, por lo
tanto, potenciando sus efectos beneficiosos en el organismo.
Con este objetivo, la primera parte de la tesis se ha centrado en el desarrollo y
puesta a punto de varios métodos para la obtención de extractos fenólicos utilizando
como fuente el alperujo, principal subproducto generado a partir del proceso de
extracción de aceite de oliva virgen. El aprovechamiento del alperujo supone una
reducción del impacto medioambiental de este subproducto, además de su
revalorización. En una segunda fase de la tesis se han optimizado las etapas de
preparación de un aceite de oliva enriquecido en sus propios compuestos fenólicos,
mediante la incorporación del extracto fenólico a una matriz de aceite de oliva virgen.
Finalmente, se ha evaluado la estabilidad de los compuestos fenólicos del aceite
enriquecido mediante la aplicación de un modelo de digestión “in vitro”, así como su
biodisponibilidad “in vivo” en humanos después de la ingesta de una dosis única de 30
mL del aceite enriquecido.
Paralelamente, y con el objetivo de llevar a cabo la correcta cuantificación de los
compuestos fenólicos en el extracto y en el aceite de oliva enriquecido así como de los
metabolitos fenólicos en plasma, se han desarrollado y validado sendos métodos de
análisis. Los dos métodos de análisis validados se basan en el uso de la cromatografía
líquida de alta resolución acoplada a la espectrometría de masas en tandem lo que ha
permitido reducir sensiblemente los tiempos de análisis y aumentar la eficacia en la
cuantificación.
Los resultados obtenidos a partir del desarrollo de la tesis doctoral confirman la
idoneidad del enriquecimiento como forma de aumentar la dosis ingerida de
compuestos fenólicos a través del aceite de oliva, sin por ello incrementar la ingesta
calórica diaria.
Resum
Existeix una evidència creixent dels beneficis del consum d’oli d’oliva verge en la
prevenció de malalties associades a l’estrès oxidatiu, el qual és responsable en gran
mesura, de l’aparició de problemes cardiovasculars, càncer i malalties
neurodegeneratives. Encara que aquest efecte reductor del risc cardiovascular s’ha
atribuït tradicionalment al seu component gras (alt contingut d’àcid oleic) estudis més
recents han posat de manifest el paper de la fracció fenòlica de l’oli d’oliva en la
prevenció d’aquest tipus de malalties relacionades amb l’estrès oxidatiu. Alguns
estudis “in vivo” han mostrat l’efecte de la ingesta d’oli d’oliva verge en la reducció
d’alguns marcadors d’oxidació. No obstant, la magnitud de la millora aconseguida
amb el consum d’oli d’oliva verge és modesta per poder afirmar el seu valor predictiu
com a factor protector del risc cardiovascular. Això és explicable per la limitada
quantitat de compostos fenòlics que s’incorporen a l’organisme a través de la dosi
diària d’oli d’oliva verge en la dieta Mediterrània habitual (aproximadament de 25 a
50 mL d’oli d’oliva que aporten de 3 a 15 mg de compostos fenòlics al dia). Dintre
d’aquest marc, la principal aportació de la present tesi doctoral resideix en el
desenvolupament d’un oli d’oliva verge enriquit amb els seus propis compostos
fenòlics, incrementant així la seva ingesta diària i, per tant, potenciant els seus efectes
beneficiosos en l’organisme.
Amb aquest objectiu, la primera part de la tesi s’ha centrat en el desenvolupament i
optimització de diversos mètodes per a l’extracció dels compostos fenòlics de la
pinyola, el principal subproducte obtingut en l’obtenció de l’oli d’oliva verge.
L’aprofitament de la pinyola pot implicar una reducció de l’impacte mediambiental
d’aquest subproducte, a més a més de la seva valorització. En una segona etapa de la
tesi s’han optimitzat les etapes de preparació d’un oli d’oliva enriquit en el seus propis
compostos fenòlics, mitjançant la incorporació de l’extracte fenòlic en una matriu
d’oli d’oliva verge. Finalment, s’ha avaluat l’estabilitat dels compostos fenòlics de
l’oli enriquit mitjançant l’aplicació d’un model de digestió “in vitro”, així com la seva
biodisponibilitat “in vivo” en humans després de la ingesta d’una dosi única de 30 mL
de l’oli enriquit.
Paral·lelament, amb l’objectiu de dur a terme la correcta quantificació dels
compostos fenòlics en l’extracte i en l’oli d’oliva enriquit, així com dels metabolits
fenòlics en plasma, s’han desenvolupat i validat els respectius mètodes d’anàlisis. Els
dos mètodes d’anàlisi validats es basen en la utilització de la cromatografia líquida
d’alta eficiència acoblada a l’espectrometria de masses en tàndem, el que ha permès
reduir sensiblement els temps d’anàlisi i augmentar l’eficàcia en la quantificació.
Els resultats obtinguts en la present tesi doctoral confirmen la idoneïtat de
l’enriquiment com a forma d’augmentar la dosi ingerida de compostos fenòlics de l’oli
d’oliva sense per això incrementar la ingesta calòrica diària.
Summary
There is a growing evidence of the beneficial effects of olive oil consumption in
the prevention of illnesses related with oxidative stress, which is to a large extent
responsible of the appearance of cancer, cardiovascular and neurodegenerative
diseases. Although the reduction in the cardiovascular risk has been traditionally
attributed to the fatty acid content of virgin olive oil (high content of oleic acid) more
recent studies have highlighted the important role of the phenolic fraction of virgin
olive oil in the prevention of these diseases related with oxidative stress. Some “in
vivo” studies have shown the effect of virgin olive oil consumption in the reduction of
some oxidative markers. However, the extent of the effectiveness of olive oil
consumption is modest to state its predictive value as protector of the cardiovascular
risk. This fact can be explained by the limited dose of phenolic compounds that is
provided from the daily intake of virgin olive oil in the Mediterranean diet (which
range from 25-50 mL of olive oil, approximately a daily intake of 3-15 mg phenolic
compounds). The main contribution of this doctoral thesis is the development of an
olive oil enriched in their own phenolic compounds to increase their daily intake and
strength their healthy effects within the organism.
To reach this objective, the first stage of the thesis was focused in the development
and optimization of different methods to extract phenolic compounds from olive cake,
the main by-product generated in the virgin olive oil extraction. The use of the olive
cake could mean a reduction of the environmental impact of this by-product, besides
its valorization. In a second stage of the thesis, an optimization of the steps for the
development of an enriched olive oil using the phenol extract was carried out. Finally,
the stability of the phenolic compounds was evaluated by the “in vitro” digestion of
the enriched olive oil and their “in vivo” bioavailability was evaluated in humans
through the ingestion of a single dose of 30 mL of enriched oil.
Simultaneously, to quantify the phenolic compounds from both the olive cake
extracts and the olive oil, as well as the corresponding metabolites from plasma
samples, two analytical methods were developed and validated. Both methods are
based on the use of high performance liquid chromatography coupled to tandem-mass
spectrometry which allowed to significantly reduce the analysis time and improve the
efficiency in the quantification.
The results obtained in this doctoral thesis confirm the suitability of the phenolic
enrichment of the olive oils as tool to increase the daily intake of phenolic compounds
from this source without increasing the caloric ingestion.
Índice General
I.
Introducción....……………………………………………………..…………1
1. Alimentos funcionales…………………...……………………………………....3
2. El aceite de oliva como alimento funcional………………………………..…….6
3. Compuestos fenólicos……………………………………………………….….10
3.1. Clasificación de los compuestos fenólicos………………………………...10
3.2. Compuestos fenólicos en los alimentos………………………….……...…11
3.3. Actividades biológicas y biodisponibilidad de los compuestos fenólicos…14
3.4. Efecto de los compuestos fenólicos sobre la expresión génica…………....19
4. Subproductos de la industria alimentaria………...……………………………..20
4.1. Los subproductos de almazara……………………...……………………...21
4.1.1. Composición del alperujo………………...………………………….22
4.1.2. Composición fenólica del alperujo………………...………………...24
4.1.3. Valorización del alperujo…………………………...…….………….27
4.2. Los subproductos de la elaboración del vino………………...…………….30
4.2.1. Composición fenólica del orujo de uva………………...…................31
4.2.2. Valorización del orujo de uva………...……………………………...33
5. Técnicas de obtención de extractos fenólicos…………………………………..34
5.1. Técnicas tradicionales de extracción y análisis…………………................34
5.2. Nuevas tendencias en las técnicas de extracción...…...…………................37
5.3. Aspectos legislativos para la obtención de extractos de uso alimentario….39
6. Validación de métodos analíticos……………………...……………………….40
6.1. Importancia de la validación de métodos…………………...……………..40
6.2. Tipos de validación…………………………...…………………………....41
6.3. Parámetros de calidad en la validación de métodos cromatográficos…..….41
7. Bibliografía………………................…………………………………………..43
II. Objetivos…………...…………………….…………...……………………..55
III. Plan de trabajo…………...….…………………………………..………….59
IV. Material y métodos………...…………………….…………..……………..67
1. Obtención de extractos fenólicos del alperujo……….……………………...….69
1.1. Muestras………….……………………………...………………………….69
1.2. Extracción de compuestos fenólicos de las aguas de vegetación……….….69
1.3. Extracción de compuestos fenólicos del residuo sólido…………................70
1.4. Extracción de fenoles del alperujo……………………………...…………..71
1.5. Determinación de polifenoles totales…………………………………….…71
1.6. Identificación de compuestos fenólicos por cromatografía líquida...............71
2. Métodos de evaluación de la capacidad antioxidante………………..................74
2.1. Evaluación de la capacidad antioxidante por el método DPPH……….……74
2.2. ORAC hidrofílico…………………………………………...…..………….75
3. Enriquecimiento de los aceites………………………………………................75
3.1. Muestras……………………………………………………...……………..75
3.2. Emulgentes…………………………………………………...……………..76
3.3. Enriquecimiento de los aceites………………………………...…………...76
3.4. Estabilidad oxidativa de los aceites……………………………...................76
3.5. Análisis de fenoles totales…………………………………...……………...77
3.6. Extracción y análisis de compuestos fenólicos por HPLC……...………….77
3.7. Parámetros de calidad del aceite…………………………………................78
3.8. Determinación del índice de amargor (K225)…………………...…………...80
3.9. Determinación de pigmentos fotosintéticos totales……………...................80
3.10. Determinación capacidad antioxidante por método ORAC…...………….81
3.11. Digestión de los aceites…………………………..……………………......81
4. Análisis de compuestos fenólicos en plasma………………….……………......82
4.1. Muestras……………………………………...…………………….……….82
4.2. Extracción de fenoles del plasma…………………………………………...82
4.3. Análisis de fenoles del plasma por UPLC-ESI-MS/MS………...................83
5. Desarrollo de un sistema en continuo de extracción de compuestos fenólicos a
partir de alperujo de uva…………………………………………………………..83
5.1. Muestras……………………………….………………...………………….83
5.2. Extracción de compuestos fenólicos del orujo de uva………….…………..83
5.3. Determinación de antocianinas totales monoméricas…………................…84
5.4. Identificación de antocianinas por HPLC-ESI-MS…………….…………..84
5.5. Identificación de procianidinas por HPLC-fluorescencia……………….….85
6. Análisis estadístico……………………….………………………….................86
7. Bibliografía…………………………………………………...………………...87
V. Publicaciones….…………………...…………...…………………...............89
Publicación 1: Improved liquid chromatography tandem mass spectrometry
method for the determination of phenolic compounds in virgin olive oil
(Journal of Chromatography A) …………………………………………..…..91
Publicación 2: Methods for preparing phenolic extracts from olive cake for
potential application as food antioxidants (Journal of Agricultural and Food
Chemistry) …………………………………………..………………………..117
Publicación 3: Comparison of phenol extracts prepared from olive-oil byproducts by accelerated solvent extraction: Effect of solvent and extraction
temperatura (en revisión)…………………...……………………………...…141
Publicación 4: Development of a phenol-enriched olive oil with phenolic
compounds from olive-cake (Journal of Agricultural and Food
Chemistry)………………………………………………...…………………..165
Publicación 5: Study of stability during storage of a phenol-enriched olive oil
(en revisión)…………………………………………..…………...………….193
Publicación 6: Improved method for identifying and quantifying olive oil
phenolic compounds and their metabolites in human plasma by microelution
solid-phase extraction plate and liquid chromatography–tandem mass
spectrometry (Journal of Chromatography B) ………....................................219
Publicación 7: Enhanced bioavailability of virgin olive oil phenols by the
ingestion of a phenol-enriched olive oil (en revisión)….......……..…............247
Publicación 8: Extracting Anthocyanins and Procyanidins from red grape
pomace using an industrially applicable continuous method (en
preparación)………………………………………………………………….271
VI. Discusión general………………...…………...……………………………301
VII. Conclusiones………………...……..……...……………………………….333
VIII. Anejos……………...………………...……………...…………………….339
Índice de Figuras
Figura 1. Pirámide de la Dieta Mediterránea……………………………………….…6
Figura 2. Producción media mundial de aceite de oliva en el periodo 2003-2009........7
Figura 3. Consumo mundial de aceite de oliva en el periodo 2003-2009…………..…8
Figura 4. Estructura química básica de los ácidos fenólicos………………………...12
Figura 5. Estructura química básica de los flavonoides y sus principales subgrupos..13
Figura 6. Estructura química básica de los lignanos…………………………………14
Figura 7. Estructura química básica de los estilbenos……………………………….14
Figura 8. Principales actividades biológicas de los compuestos fenólicos…………..15
Figura 9. Actividades enzimáticas características del metabolismo de los compuestos
fenólicos………………………………………………………………………………17
Figura 10. Posibles rutas de los compuestos fenólicos de la dieta en el organismo…18
Figura 11. Interacción de la nutrición (tanto nutrientes como no-nutrientes) con el
genoma………………………………………………………………………………..19
Figura 12. Diagrama de flujo del sistema de centrifugación de 2 fases…………….22
Figura 13. Principales flavonoides del alperujo……………………………………...25
Figura 14. Principales compuestos secoiridoides y sus derivados más comunes en el
alperujo……………………………………………………………………………..…26
Figura 15. Principales alcoholes fenólicos del alperujo……………………………...27
Figura 16. Principales lignanos del alperujo………………………………………....27
Figura 17. Principales antocianinas presentes en el orujo de uva…………………...32
Figura 18. Estructura química del resveratrol………………………………………..32
Figura 19. Principales componentes del extractor ASE100……………………...….70
Figura 20. Rancimat Metrohm 679 y accesorios necesarios para su uso…………….77
Figure 21. Chemical structures of the studied phenolic compounds………………...97
Figure 22. Total ion chromatograms (TIC) in SRM acquisition obtained from the
analysis of the fourteen phenolic compounds in standard solution………………....102
Figure 23. MS chromatogram and MS spectrum obtained at the front (A), at the
middle (B) and at the tail (C) of the peak 3,4-DHPEA-EDA……………………….104
Figure 24. Extracted ion chromatograms of the identified phenolic compounds in a
virgin olive oil sample by LLE-UPLC-MS/MS……………………………………..109
Figure 25. HPLC-DAD chromatograms of the vegetative water (a) and solid residue
(b) extracts by the procedures under study. Procedure A was done using ethyl acetate
as solvent of extraction; Procedure B included an alkaline hydrolysis previously to the
extraction with ethyl acetate. Procedure C was done by extraction at atmosphere
pressure and Procedure D was done at high pressure using an ASE………………..128
Figure 26. Semi-preparative HPLC chromatogram corresponding to the VW extract
using Procedure A showing the isolated fractions (26A). The chromatogram was
extracted at two wavelengths (278 and 339 nm). Figure 26B shows the UPLC-DAD
chromatograms from the isolated fractions (VW1 to VW12). …..…………………...132
Figure 27. Semi-preparative HPLC chromatogram corresponding to the SR extract
using Procedure C showing the isolated fractions (27A). The chromatogram was
extracted at two wavelengths (278 and 339 nm). Figure 27B shows the UPLC-DAD
chromatograms from the isolated fractions (SR1 to SR6). ………….……………….133
Figure 28. Antioxidant activity of the isolated fractions and the whole extracts by the
DPPH method and the ORAC assay. ...……………………………………………..135
Figure 29. Response surface of the effect of percentage of ethanol and temperature on
the total phenolic content and the ORAC activity……………………..……………152
Figure 30. Response surface of the effect of percentage of ethanol and temperature on
the content of hydroxytyrosol, 3,4-DHPEA-EDA and luteolin……………………..157
Figure 31. Influence of the percentage of ethanol in the extraction solvent and
working temperature on the total carotenoid and chlorophyll content in the extraction
from olive cake samples using an ASE……………………………………………...160
Figure 32. Effect of the addition of emulsifier on the oxidative stability of the
enriched olive oils. Values expressed as hours (n=3)……………………………….203
Figure 33. Evolution of the quality parameters of the enriched olive oil during the
storage in dark bottles at 25º C……………………………………………………...207
Figure 34. Evolution of the total phenolic content (a), K225 (b) and oxidative stability
(c) of the enriched olive oil during the storage in dark bottles at 25º C…………….209
Figure 35. Principal components analysis of the enriched olive oils based on the main
important factors under study (Rancimat: oxidative stability; K225: bitterness index;
Phenols: total phenolic content; Acidity; K270; Peroxide: peroxide value)………….211
Figure 36. Changes in the antioxidant capacity between fresh enriched oils and after
the storage (256 days)……………………………………………………………….212
Figure 37. Changes in the amount of secoiridoid derivatives between fresh enriched
oils and after storage (256 days)…………………………………………………….213
Figure 38. Extracted ion chromatograms of the generated metabolites identified in the
plasma samples after the intake of 30 mL of phenol-rich virgin olive oil………..…237
Figure 39. Extracted ion chromatograms of the free phenols identified in the plasma
samples after the intake of 30 ml of phenol-rich virgin olive oil……………………239
Figure 40. Study design of the acute ingestion study of control and enriched olive
oil……………………………………………………………………………………253
Figure 41. Metabolic pathways of hydroxytyrosol…………………………………259
Figure 42. Proposed metabolic pathways of tyrosol………………………………..260
Figure 43. Pharmacokinetics of (a) hydroxytyrosol sulphate, (b) 3,4-DHPEA-EA
derivative glucuronide, (c) apigenin glucuronide and (d) ferulic acid glucuronide in
human plasma after the intake of control and phenol-enriched olive oil …………...265
Figure 44. Schematic of the expeller-extraction system……………………………276
Figure 45. HPLC-ESI-MS chromatogram of the anthocyanins contained in the White
Zinfandel red grape pomace extract…………………………………………………284
Figure 46. Significant factors under study in monomeric anthocyanin content
influenced by (1) flow rate and temperature of the bath (2) flow rate and temperature
of the shaft and (3) temperature of the bath and temperature of the shaft with (a)
corresponding to dried samples and (b) corresponding to non-dried samples………287
Figure 47. HPLC chromatogram of White Zinfandel grape pomace
procyanidins…………………………………………………………………………289
Figure 48. Significant factors under study in total procyanidin content influenced by
(1) flow rate and temperature of the bath and (2) rotation and temperature of the shaft
with (a) corresponding to dried samples and (b) corresponding to non-dried
samples………………………………………………………………………………291
Figure 49. Effect of flow rate and temperature on antioxidant activity of the extracts
as determined by ORAC assay in dried pomace and non-dried pomace…………....294
Figura 50. Esquema del sistema propuesto para la extracción en continuo de
compuestos fenólicos a partir de subproductos de la industria del vino…………….328
Índice de Tablas
Tabla 1. Clasificación de los compuestos fenólicos según Harborne ………...…..…11
Tabla 2. Características y composición del alperujo de oliva………………………..23
Tabla 3. Características y composición del orujo de uva…………………………….31
Tabla 4. Condiciones cromatográficas utilizadas para la identificación de fenoles de
la oliva por HPLC-DAD……………………………………………………………...72
Tabla 5. Condiciones cromatográficas utilizadas para la separación de los fenoles de
la oliva en el cromatográfo semi-preparativo HPLC-UV…………………………….73
Tabla 6. Valores máximos autorizados para el aceite de oliva virgen según la
Normativa Europea vigente…………………………………………………………..78
Tabla 7. Condiciones cromatográficas utilizadas para la determinación de
antocianinas por HPLC-ESI-MS……………………………………………………...85
Tabla 8. Condiciones cromatográficas utilizadas paral la identificación de
procianidinas por HPLC-fluorescencia……………………………………………….86
Table 9. Optimized SRM conditions for the analyses of the studied phenolic
compounds by UPLC-MS/MS………………………………………………………..99
Table 10. Retention time (Rt), linearity, reproducibility (%RSD) n=3, LODs and
LOQs for the analysis of the fourteen phenolic compounds by HPLC-fluorescence,
UPLC-DAD, and UPLC-MS/MS in standard solutions…………………………….105
Table 11. Recovery (%R), linearity, calibration curve, reproducibility (RSD) (n=3),
LOD and LOQ for the analysis of fourteen phenolic compounds in spiked ROO
UPLC-MS/MS. Linearity, LOD and LOQ are expressed as µg/kg…………………107
Table 12. Identified phenolic compounds in virgin olive oil and their
quantification………………………………………………………………………..110
Table 13. SRM Conditions for the Analysis of Polyphenols by UPLC-ESIMS/MS………………………………………………………………………………125
Table 14. Phenolic Compounds Quantified by UPLC-ESI-MS/MS of the VW and SR
extracts………………………………………………………………………………131
Table 15. Experimental central composite design for response surface analysis and
values of total phenolic content (expressed as mg caffeic/g extract) and ORAC activity
(expressed as µmoles Trolox/ g extract)…………………………………………….149
Table 16. ANOVA for the effect of percentage of solvent and temperature on the
total phenolic content (A) and the ORAC activity (B) by a response surface quadratic
model………………………………………………………………………………...151
Table 17. Quantification of the phenolic compounds in the olive cake ASE extracts
using different percentages of ethanol and temperatures. Values are expressed in mg
compound/g extract……………………………………………………………….…155
Table 18. Values of total carotenoids and total chlorophylls content for a central
composite response surface design……………………………………………….....158
Table 19. Phenolic composition of the olive cake extracts analysed by UPLC-ESIMS/MS following the method described in Material and Methods. Values expressed as
mg phenol/g freeze-dried extract……………………………………………………177
Table 20. Effect of phenolic enrichment on the oxidative stability by Rancimat test
(expressed as hours) and the total phenolic content by Folin-Ciocalteau (expressed as
mg caffeic acid equivalents/kg oil) of the oils………………………………………179
Table 21. Quality parameters (peroxide value, acidity and K270), oxidative stability,
total phenolic content, bitter index (K225), total chlorophyll and carotenoid content of
the control (virgin olive oil) and phenol-enriched olive oils…………………….….181
Table 22. Phenolic composition of the control (virgin olive oil) and phenol-enriched
olive oils by UPLC-ESI-MS/MS expressed as nmol of phenol per gram of oil…….183
Table 23. Antioxidant capacity of the control (virgin olive oil) and phenol enriched
olive oils by ORAC assay…………………………………………………………...184
Table 24. Amounts of phenols in aqueous micellar fraction after in vitro digestion of
control (virgin olive oil) and phenol-enriched olive oils……………………………186
Table 25. Phenol composition of enriched olive oils……………………………...205
Table 26. Phenolic composition of the olive-cake extract used to carry out the oil
enrichments……………………………………………………………………….…218
Table 27. Optimized SRM conditions for the analyses of the studied phenolic
compounds by UPLC-MS/MS………………………………………………………227
Table 28. SPE conditions and % recovery for the analysis of the 10 phenolic
compounds in spiked plasma samples by off-line SPE cartridges and ȝSPE……….231
Table 29. Retention time (RT, min), recovery (%R), linearity, calibration curves,
reproducibility (RSD), LODs and LOQs for the determination of the ten phenolic
compounds in spiked plasma samples………………………………………………233
Table 30. SRM conditions for the analysis of the metabolites by UPLC-MS/MS…235
Table 31. Phenol metabolites and their free forms identified and quantified (µM) in
plasma samples 60 and 120 minutes after the consumption of 30 ml of virgin olive oil
rich in phenolic compounds…………………………………………………………238
Table 32. Phenolic profile of the control and enriched olive oils determined by UPLCESI-MS/MS. Values expressed as mg compound/kg oil……………………………256
Table 33. Chromatographic parameters of the main peaks observed in the plasma
samples after the ingestion of the oils……………………………………………….258
Table 34. Pharmacokinetics parameters for the metabolites derived from the
secoiridoids in plasma samples after the intake of either control or enriched olive
oil.…...........................................................................................................................262
Table 35. Pharmacokinetics parameters for the metabolites derived from phenolic
acids and flavonoids in plasma samples after the intake of either control or enriched
olive oil……………………………………………………………………………...263
Table 36. Experimental central composite design for response surface analysis,
percentage of total monomeric anthocyanins, total procyanidins and ORAC activity
compared with the obtained by the traditional extraction with metanol:water:formic
acid (60:37:3, v/v/v)…………………………………………………………………283
Table 37. Peak assignments, retention times and mass spectra data of anthocyanins
detected in extracts of White Zinfandel Red Grape Pomace………………………..285
Table 38. Peak assignements, retention times and mass spectral data of procyanidins
detected in extracts of White Zinfandel Red Grape Pomace………………………..289
Tabla 39. Metodologías seguidas en la obtención de extractos fenólicos del
alperujo………………………………………………………………………………307
Tabla 40. Composición fenólica de los extractos en mg compuestos/g de extracto
analizada por UPLC-ESI-MS/MS…………………………………………………...308
Tabla 41. Composición fenólica de los extractos en mg compuestos/g de alperujo
fresco………………………………………………………………………………...310
Tabla 42. Evolución de la composición fenólica de los extractos de ASE obtenidos a
partir del alperujo liofilizado en base a la temperatura de extracción y el porcentaje de
etanol utilizado en el solvente de extracción………………………………………..311
Tabla I. Rendimientos de extracción de compuestos fenólicos respecto a la cantidad
de alperujo de partida para las diferentes metodologías estudiadas. Valores expresados
en g liofilizado/g de alperujo………………………………………………………..341
Tabla II. Rendimientos de extracción de compuestos fenólicos respecto a la cantidad
de alperujo de partida obtenidos al variar las condiciones de temperatura y porcentaje
de etanol en el solvente de extracción. Valores expresados en g liofilizado/g de
alperujo………………………………………………………………………………341
Índice de abreviaturas
2FI
Modelo de doble interacción/ Two factor model interaction
3,4-DHPEA
Hidroxitirosol ó 2-(3,4-dihidroxifenil)etanol/ Hydroxytyrosol
3,4-DHPEA-AC
4-acetoxietil-1,2-dihidroxibenceno
3,4-DHPEA-EA
Forma aldehídica del ácido elenólico unido al hidroxitirosol
u oleuropeina aglicona
3,4-DHPEA-EDA Forma dialdehídica del ácido elenólico unida al hidroxitirosol
A
Absorbancia
AAPH
2,2’-azobis (2-amidino-propano) dihydrochloride
ASE/PLE
Extracción acelerada por solventes/Accelerated Solvent
Extraction
AUC
Área bajo la curva/ Area Under curve
CBG
β−glucosidasa citosólica/cytosolic ȕ-glucosidase
CE
Electroforesis capilar/ Capillary electrophoresis
CHD
Coronary Heart Disease
COMT
Catecol-O-metil-transferasa/Catechol-O-methyl transferase
DAD
Detector de fotodiodos/ Diode Array Detector
DPPH
2,2-difenil-1-picrilhidrazilo
EDTA
Etilendiaminotetraacético
ESI
Ionización por electroespray/ Electrospray ionisation
GC
Cromatografía de gases/ Gas Chromatography
GRAS
Generally Recognized As Safe
HPLC /LC
Cromatografía líquida de alta resolución/ High Performance
Liquid Chromatography
IP
Índice de peróxidos
LDL
Lipoproteínas de baja densidad
LLE
Extracción en fase líquida/ Liquid-liquid extraction
LOD
Límite de detección/ Limit of detection
LOQ
Límite de cuantificación/ Limit of quantitation
LPH
Hidrolasa floridzina lactasa/ Lactase-phlorizin hydrolase
MAE
Micro-wave assisted extraction
MS
Espectrometría de masas
MS/MS
Espectrometría de masas en tándem/tandem mass spectrometry
n.d.
No detectado/ Not detected
n.q.
No cuantificacdo/ Not quantified
ORAC
Oxygen Radical Absorbance Capacity
p-HPEA
Tirosol ó 2-(4-hidroxifenil)etanol/ Tirosol
p-HPEA-EDA
Forma dialdehídica del ácido elenólico unida al tyrosol
p-HPEA-EA
Forma aldehídica del ácido elenólico unido al tyrosol
PM/MW
Peso molecular/Molecular weight
R%
Porcentaje de recuperación/ Recovery
Rt
Tiempo de retención/ Retention time
RMCD
Metil-ȕ-ciclodextrina
ROO
Refined olive oil
RSD
Desviación estándar relativa/ Relative Standard Devitation
RSM
Response surface methodology
S/N
Relación señal-ruido/ Signal-to-noise ratio
SFL
Supercritical fluid extraction
SPE
Extracción en fase sólida/Solid phase extraction
SR
Residuo sólido/ Solid Residue
SRp
Residuo solido purificado
SRnp
Residuo sólido no purificado
SRM
Selected reaction monitoring
SULT
Sulfotransferasa/sulphotransferase
SWE
Sub-critical water extraction
TLC
Cromatografía en capa fina/ Thin layer chromatography
TQD
Detector de triple cuadrupolo/ Triple quadrupol detector
UGT
Uridina-difosfato-glucuronosiltransferasa/Uridine DiphosphateGlucuronosyltransferase
UV
Ultravioleta
UPLC
Cromatografía líquida de ultra resolución/ Ultra Performance
Liquid Chromatography
VW
Aguas de vegetación/ Vegetative waters
Agradecimiento
Es muy difícil resumir en unas pocas líneas todo lo que quisiera decir para
agradecer a las personas que han hecho posible la realización de esta tesis. Este
momento supone, no sólo el fin del período de 4 años que ha durado mi etapa como
becario pre-doctoral, sino la culminación de un periodo que comenzó hace ya muchos
años con mi llegada al Departament en 2002 para realizar el TPT con Pedro.
Posteriormente realicé el PFC con Luz Stella y de ahí ya me reenganché para el
doctorado. Así pues, han sido mucho años en los que el Departament de Tecnologia
dels Aliments se ha llegado a convertir en mi segunda casa. Por todo ello quisiera
agradecer a todas las personas que han pasado por él durante todo este tiempo, desde
profesores, técnicos y becarios a estudiantes de prácticas, por todos los buenos
momentos compartidos tanto en horas de trabajo como fuera de él (comidas, cafés,
excursiones, cenas “perdidas”, de “traje” y demás).
Quisiera agradecer a las “jefas”, Mª José y Mª Paz por la oportunidad que me
brindaron al ofrecerme comenzar el doctorado con ellas. Gracias por la confianza
depositada en mí, por transmitirme vuestros conocimientos y formarme como
investigador. Me habéis demostrado ser, no sólo grandes profesionales, sino
magníficas personas. Espero haber podido estar a la altura.
A todas mis compañeras del lab: LuzStella, Maria, Arantza, Alba, Fanny, Magda,
Nadia, Aida y Laura. Gracias por todos los buenos momentos compartidos, por
vuestra ayuda cuando lo he necesitado y por estar ahí apoyando siempre. Ahora os
tendréis que buscar otro chico que pase a ser la representación masculina del grupo^^.
Maria, nuestra amistad se remonta a los tiempos de la carrera, gracias por toda tu
ayuda y compañía en este tiempo, con los fenoles, el CAP, las clases de inglés y
demás. Qué dure mucho años más! Vete preparando que la siguiente del grupo en
acabar eres tú! Alba, moltes gràcies per la teva ajuda amb el MS/MS i pels teus
consells durant la redacció de la tesis. Aida, desde que vas arribar al grup vas
demostrar-me ser una gran amiga. Espero podem continuar així molts anys més!
“Watashi-tachi no yǌjǀ wa eien ni tsuzuku koto o nozomu. Watashi no kazu wa nani
no tame ni hitsuyǀ” ;). Laura, mucha suerte en la etapa que empiezas ahora! Cualquier
ayuda que necesites con los aceites puedes contar conmigo. Fanny!! La persona más
trabajadora del mundo!!! Echamos de menos tu alegría cada día!!!
Quisera agradecer también a todos los doctorandos que ha habido en el
Departament, a los “vecinos” de micro y a los de nuevas tecnologías, demasiados para
nombraros a todos sin dejarme a alguno. Asi que muchas gracias a todos!!
A mis compañeros de la sala de becarios, hemos pasado tantas horas encerrados
escribiendo sin parar... muchos ánimos a todos en el tiempo que os queda!! Liliana! e
é curto! muito incentivo no que resta. Espero que nossa amizade possa continuar por
muito mais tempo! Bernarda, mucha suerte en el año final. A partir de ahora te toca
ser la primera a tí!! Cuenta conmigo para lo que necesites! Mariana, Rogelio, mucho
ánimo en la parte final de la tesis.
Agradecer a Noelia e Isa, no sólo por son grandes amigas, sino también por
subirme y bajarme cada día durante todos estos años. Creo que ya va siendo hora que
me saque el carnet de conducir...
To all the people from Fayeteville! Thank you for all your help during the 7
months that I stayed there. I’d like to express my gratitude to all the staff from ERC,
from the Food Technology Department, from Washington Regional and from Garden
Park. Thanks to all of you!! Dr. King, thanks for giving me the opportunity to work in
your lab and share with me your experience to improve my knowledge. Keerthi, ey
dude!! thanks for your help all the time that I needed. DongFang, you are an excellent woman! I’m glad to met you in Arkansas.
Thank you for all your help, for all the times that you gave me a lift home and all your
help when I needed. Thanks also to your husband!! Nín suԁ xǌyào de zài zhèlӿ nӿ yԁu
yƯgè yԁngyuӽn de péngyԁu! FƝicháng gӽnxiè!! Jeanna, it was a pleasure working with
you. You are and excellent researcher and even better person. Glad to be your friend!!
Jeff, I’ll never live enough to express all the gratitude that I feel for you and your
familiy. You’re the best person I’ve ever met! Thanks for you friendship, your help
during my recovery, for bringing me the meals that your wife and your mother
prepared for me and let me feel in family all my time in Fayetteville. You have a
friend in Spain always you need!!
Ingrid, nuestros caminos han ido paralelos todos estos años. Muchas gracias por
todo, por tu amistad, tu comprensión, por todos los momentos que hemos vivido y que
viviremos. Aquí estaré siempre a tu lado para lo que necesites. Sonia, contigo me
tengo que remontar a la época del insti, imagínate, llevamos más de media vida
juntos!! Y lo que nos falta!!! Muchas gracias por todo!! Por estar ahí y demostrarme tu
amistad en todo momento.
También quiero agradecer al resto de amigos que con su apoyo han ayudado en el
largo periodo de la tesis: a los amigos de la uni (Claudia, Francesc, Eli, Ester, Ingrid,
Miquel, Maria, Noelia y respectiv@s), Addy y Daiana (ché, ahora toca festejarlo no),
Luciano, Xavi, Tere y Chus. A Edu y a Sergi (muchas gracias por la tapa!!), a Blanca,
Montse, Laura, Noemi, Eli y Jordi y a Celia. Muchas gracias a todos!!
Por último agradecer a mi familia por apoyarme en esta aventura y en todas las que
vengan. A mis tíos, tías, primos, parejas e hijos. A mis hermanos (Ramón, Sisco y
David) a mi hermana (MªCarmen), a mis sobrinos (Cristian, Ramón, Abel y
Alejandro) y a mis padres. Vosotros sois los que tenéis que aguantar no sólo los
buenos momentos sino también los malos, muchas gracias por todo!! Quién os iba a
decir que llegaría hasta aquí! Sin vosotros no hubiera sido posible!
Creo que ya me estoy enrollando demasiado así que aquí lo dejamos, muchas
gracias a todos y hasta la próxima!!
!" !#$
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Publicación 7: Fenoles plasma aceite enriquecido
Publicación 7
Enhanced bioavailability of virgin olive oil phenols by the ingestion of a
phenol-enriched olive oil
Manuel Suárez, Maria-Paz Romero, Alba Macià, Rosa M Valls, Sara
Fernández, Rosa Solà, Maria-José Motilva
Molecular Nutrition and Food Research
En revisión
247
248
Enhanced bioavailability of virgin olive oil phenols by the ingestion of a
phenol-enriched olive oil
Manuel Suárez,1 Maria-Paz Romero,1 Alba Macià,1 Rosa M Valls,2 Sara
Fernández,2 Rosa Solà,2 Maria-José Motilva1*
1
Food Technology Department, XaRTA-TPV, Escuela Técnica Superior de Ingeniería
Agraria, University of Lleida, Av/Alcalde Rovira Roure 191, 25198 Lleida, Spain
2
Lipid and Arteriosclerosis Research Unit (CIBERDEM), St. Joan de Reus University
Hospital, IISPV, Facultat de Medicina i Ciències de la Salut, Universitat Rovira i Virgili, C/
Sant Llorenç 21, 43201 Reus, Spain
Abstract:
Virgin olive oil, the main source of fat in the Mediterranean diet, has been
associated with the low incidence of coronary heart diseases and other pathologies in
these countries. Several studies have demonstrated that phenolic compounds are one
of the main reasons behind these healthy properties. However, their daily intake from
virgin olive oil is very low compared with that obtained from other phenolic sources
as a consequence of the limited daily intake of olive oil. For this reason, the ingesta of
virgin olive oil enriched with its own phenolic compounds could be of interest to
increase the daily dose of these beneficial compounds. To evaluate the effectiveness of
enrichment and its effects on the bioavailability in vivo, the concentration of phenolic
compounds and their metabolites in human plasma (0, 60, 120, 240 and 300 min) from
16 healthy volunteers (8 men and 8 women, aged 21 and 69) was determined after the
ingestion of a single dose (30 mL) of either enriched virgin olive oil (961.17 mg/kg
oil) or control (288.89 mg/kg oil) in a cross-over study. Relative to control virgin oil,
enriched oil increased plasma concentration of the phenol metabolites particularly,
hydroxytyrosol sulphate and vanillin sulphate (p<0.05). However, the wide variability
of results indicates that the absorption and metabolism of olive oil phenols is highly
dependent on the individual.
Key words: Phenol enriched olive oil, human plasma, phenol metabolites, phenol
bioavailability
249
1. Introduction
Over the last decade epidemiological studies have proven that Mediterranean diet,
rich in vegetables, fruit and legumes, is correlated with a low incidence of coronary
heart diseases and cancer (Knoops et al., 2004). Within this nutritional pattern, olive
oil plays an important role, being the main source of fat in the diet in this area. The
beneficial effects of virgin olive oil were initially attributed to its fatty acid
composition, rich in monounsaturated fatty acids. Nevertheless, further studies have
highlighted the importance of its phenolic composition, especially after the publication
of the results of the EUROLIVE project which demonstrated that the increase in the
HDL cholesterol level and the decrease in the lipid oxidation damage after virgin olive
oil consumption were highly correlated with its phenolic content (Covas, 2007, 2008).
Thus, phenolic compounds from virgin olive (mainly phenolic alcohols, secoiridoid
derivatives, phenolic acids, lignans and flavonoids) have been reported to have
antioxidant (Obied et al., 2007), anti-inflammatory (Visioli and Galli, 2002), antiatherogenic (Visioli and Galli, 2001) and anti-carcinogenic properties (Owen et al.,
2000).
The metabolic fate of the phenolic compounds from virgin olive oil after ingestion
in humans is still scarcely known. Studies have focused on such specific compounds
as hydroxytyrosol and tyrosol. However, little has been done about the other
components of the phenolic fraction of virgin olive oil. It is known that polyphenols
are subjected to strong metabolism of phase I and phase II where they are hydrolyzed
(phase I) and later conjugated (phase II) into their glucuronidated, methylated and
sulphated metabolites forms in order to be absorbed (Manach et al., 2004). In addition,
in vivo studies have shown that hydroxytyrosol and tyrosol are dose-dependently
absorbed in humans and excreted in urine in their free or conjugated forms (Visioli et
al., 2000).
More recent studies have indicated that the beneficial effects of the phenolic
compounds from virgin olive oil are not only due to their antioxidant and related
activities but they also have a nutrigenomic effect, which means that their intake has a
direct impact on the human genome. Thus, a study carried out by Konstantinidou et al.
(2010) showed that the phenols from virgin olive oil have a significant role in the
down-regulation of such proatherogenic genes as IFNγ, ARHGAP15 and IL7R. This
reinforces the importance of including virgin olive oil in the regular diet (the FDA
recommends a daily intake of 23g of olive oil).
Nevertheless, the amount of phenolic metabolites from virgin olive oil detected in
human plasma samples is highly variable and depends on both the extraction and the
250
analytical procedure. Thus, Vissers et al. (2002) reported that the bioavailability of
these compounds in ileostomed volunteers was up to 66% of the total ingested.
Considering a mean intake of 50g of olive oil per day, these authors estimated that the
total amount of phenolic compounds in the plasma samples could be at most 0.06
µmol of hydroxytyrosol equivalents/L plasma. However, some studies revealed that a
higher concentration is required to protect LDL from oxidation. For example, Leenen
et al. (2002) concluded that at least 50-100µmoles of phenolic compounds from virgin
olive oil/L plasma are required to have a protective effect on the LDL. Therefore,
according to these results, enough phenols are unlikely to be obtained from virgin
olive oil to have a direct protective effect on the LDL. In addition, the concentration of
phenolic compounds in commercial olive oils is widely dependent of agronomical and
technical factors (Esti et al., 1998). This decreases the ingestion of phenols from
virgin olive oil compared with the doses ingested from other sources and makes it
difficult to ensure a regular dose of phenols through the daily intake of virgin olive oil.
For this reason, the enrichment of virgin olive oils with their own phenols, thus giving
a high and standardized content of phenolic compounds, could be desirable in order to
increase the daily intake of phenols without the drawback of a higher caloric content.
The aim of this study was to evaluate the effect of the enrichment of virgin olive oil
with their own phenolic compounds into their bioavailability in humans. To fulfil this
objective, the phenol metabolites were identified and quantified in human plasma
samples obtained after an acute ingestion of 30 mL of a phenol-enriched olive oil.
Plasma samples were obtained at 0, 60, 120, 240 and 300 min in order to study the
pharmokinetic behavior of these metabolites. The results were compared with those
obtained after the ingestion of the control virgin olive oil (without phenol addition).
2. Experimental
2.1. Chemicals and reagents
The phenolic compounds, apigenin, luteolin, hydroxytyrosol, tyrosol, and pcoumaric acid, were purchased from Extrasynthese (Genay, France). Caffeic and
homovanillic acids were purchased from Fluka Co. (Buchs, Switzerland), (+)pinoresinol was acquired from Arbo Nova (Turku, Finland), and catechol from SigmaAldrich (Germany). The secoiridoid derivatives 3,4-DHPEA-EDA, and p-HPEAEDA, and the lignan acetoxypinoresinol are not available commercially and were
isolated from virgin olive by semipreparative HPLC, as described by Artajo et al.
(2006). A stock solution of each standard compound was dissolved in methanol, and
all the solutions were stored in a dark flask at -40º C.
251
Methanol (HPLC grade), acetonitrile (HPLC grade) and acetic acid were provided
by Scharlau Chemie (Barcelona, Spain). Ortho-phosphoric acid (85%) was purchased
from Panreac (Barcelona, Spain). Water was Milli-Q quality (Millipore Corp, Bedford,
MA, USA).
2.2. Virgin olive oil
The virgin olive oil used as the matrix for the phenolic enrichment was from the
Siurana Protected Denomination of Origin (Catalonia, Spain), which is produced
exclusively from the Arbequina cultivar. On the other hand, the samples of the olivecake used to obtain the phenolic extract for the phenol enrichment, were taken from a
commercial olive oil mill from the olive-growing area of Les Garrigues (Catalonia,
Spain), which works by the two-phase centrifugation system. These samples were
taken at the decanter outlet and liquid nitrogen was immediately added to avoid
oxidative damage. The samples were stored at -40º C until the extraction of the
phenolic compounds.
2.3. Preparation of the phenol-enriched olive oil
The phenol-enriched olive oil was prepared by the addition of an extract rich in the
main phenolic compounds of virgin olive oil. This extract was obtained from olive
cake following the method described by Suárez et al. (2009a) and basically included
secoiridoid derivatives (89.4%), phenyl alcohols (3.5%) and flavonoids (6.0%).
To carry out the phenolic enrichment of the olive oil, 7 mg of olive cake phenolic
extract/mL oil and 0.3 % (p/v) of lecithin (Emulpur, Cargill, Barcelona, Spain) were
dissolved in ethanol:water (50:50, v/v) and added to the oil using a Polytron
(Kinematica, Littau, Switzerland) until completely homogenized. Finally, the olive oil
was filtered through a paper filter Ahlstrom (Ahlstrom S.A., Barcelona, Spain) and
bottled in dark bottles. The control olive oil (without added phenolic compounds) was
also submitted to the process of mixing and filtering to ensure equal conditions in all
the olive oils under study. The phenolic compounds of both the control and phenolenriched oils were extracted and characterized with the method described in our
previous paper (Suárez et al., 2008).
2.4. Volunteers and experimental design
252
The human study was approved by the Ethical Committee of Clinical Research of
Sant Joan University Hospital, Reus, Spain. The subjects gave their written informed
consent. Sixteen healthy volunteers (eight women and eight men), aged between 21
and 69, were recruited to carry out the study. The men had a mean weight of 73.6
±ҏ13.0 kg and the women’s mean weight was 65.8 ± ҏ6.0 kg while the body mass index
was 26.3 ± ҏ2.0 for men and 25.1 ± 1.3 for women. They were considered healthy
according to the results obtained after physical examination and routine laboratory
tests. However, at the moment of the ingestion three of the volunteers gave up the
study, thus reducing the final number of volunteers to thirteen.
A randomized, controlled, crossover trial was designed using control virgin olive
oil (without phenol addition) and enriched olive oil. Thus, the volunteers who
consumed control virgin olive oil in the first intervention ingested the enriched oil in
the second intervention after a 2 weeks wash-out period (Figure 40) and vice versa,
volunteers who consumed the enriched oil in the first intervention ingested the control
oil in the second one. For two weeks prior to the start of the study, the volunteers
followed a controlled diet in order to monitor the intake of nutrients. The acute
ingestion of the oil was done at 8 a.m. after an overnight fast. The control olive oil was
included in the study to enable the resulting data to be compared and conclusions
extracted.
1st ingestion
Group 1
Diet Stabilization
Wash-out
Group 2
Diet Stabilization
Wash-out
2 weeks
2nd ingestion
2 weeks
30 mL of control olive oil
30 mL of enriched olive oil
Figure 40. Study design of the acute ingestion study of control and enriched olive oil.
25. Plasma samples
253
Plasma samples were obtained by venipuncture from volunteers after the ingestion
of 30 mL of virgin olive oil. The blood samples were collected under basal conditions
(after a 12-h overnight fasting period) and 60, 120, 240 and 300 minutes after the
consumption of 30 ml of either enriched or control virgin olive oil. To obtain the
plasma samples, blood (50 mL) was collected in Vacutainer™ tubes containing
ethylenediaminetetraacetic acid (EDTA) as an anticoagulant. They were protected
from the light with aluminium foil and centrifuged for 15 min at 1,500 g and 4º C
(Kokusan, H-103RS, Japan). After that, the plasma was immediately separated from
the cells and kept at -80º C until analysis.
The extraction of the phenolic compounds from the plasma samples was carried out
following the method developed and validated in our previous paper (Suárez et al.,
2009b) using microelution plates (Waters, Milford, USA) packed with 2 mg of OASIS
HLB sorbent (Waters, Milford, USA).
2.6. UPLC-ESI-MS/MS
The analysis of the phenolic compounds from the virgin olive oil and plasma
samples was carried out by UPLC coupled to tandem MS. The UPLC system
consisted of an AcQuityTM UPLC equipped with a Waters binary pump system
(Milford, MA, USA) using an AcQuity UPLCTM BEH C18 column (1.7 µm, 100 mm x
2.1 mm i.d.). During the analysis, the column was kept at 30º C and the flow rate was
0.4 ml/min, using milliQ water/acetic acid (100:0.2 v/v) as solvent A and acetonitrile
as solvent B. The elution gradient was the one reported in our previous study (Suárez
et al., 2008).
2.7. Metabolite identification and quantification in plasma
Full-scan mode (MS) and tandem mass (MS/MS), based on neutral loss scan and
product ion scan, were used to identify and quantify the phenolic compounds and their
metabolites from plasma samples. These techniques are very effective at verifying the
structural information of the compounds when no commercially standards are
available. To start with, the analyses were carried out in full-scan mode (from 80 to
800 m/z) by applying different cone voltages from 20 to 60 V. The MS spectrum
obtained when low cone voltages were used gave information about the precursor ion
or the [M-H]-. On the other hand, when high cone voltages were applied, specific
fragment ions were generated and the MS spectrum gave information about their
254
structure. The structural information was also verified by using the product ion scan
and neutral loss scan in the MS/MS mode. In the product ion scan experiments, the
product ions are produced by collision-activated dissociation of the selected precursor
ion in the collision cell. Neutral loss scans of 80 and 176 units were used to
characterize the sulphate and glucuronide forms, respectively. The detection and
quantification of the phenolic compounds and their metabolites were then performed
based on their ion fragmentation in the MS/MS mode using SRM and double SRM.
Due to the lack of standards for these metabolites, they were quantified with the
calibration curves corresponding to their phenolic precursors. This way,
hydroxytyrosol and tyrosol metabolites were quantified using the calibration curves of
hydroxytyrosol and tyrosol respectively; homovanillic acid, vanillic acid and vanillin
metabolites were quantified using the calibration curve of homovanillic acid; pcoumaric, p-hydroxybenzoic and ferulic acids metabolites were quantified by means
of the p-coumaric acid calibration curve. Apigenin metabolites were quantified with
the apigenin calibration curve.
2.8. Statistical analysisand pharmacokinetics parameters
Data analysis was performed using Statgraphics plus v.5.1 software (Manugistics
Inc., Rockville, MA, USA). The data were analyzed by the ANOVA test with a
significance level of 0.05.
On the other hand, phenolic compounds kinetic parameters of the different
metabolites were calculated by means of PK functions (for Microsoft Excel). This
software allowed us to determine the maximum concentration of the metabolites
(Cmax) and their area under the curve (AUC), which can be used to compare the effect
of the ingestion of the different oils (control or phenol-enriched).
3. Results and Discussion
3.1. Characterization of the enriched olive oils
The phenolic profiles of both the control and enriched olive oil were analyzed by
UPLC-ESI-MS/MS. As can be seen in Table 32, the addition of the olive-cake extract
significantly increased the concentration of all the phenolic compounds in the oils. The
10.95-fold increase experimented by the phenyl alcohol fraction, made up of
hydroxytyrosol and tyrosol, was especially remarkable. These compounds are
255
biologically active so it is very interesting to have them at a higher concentration in
the olive oil available to be absorbed by the organism after ingestion.
Table 32. Phenolic profile of the control and enriched olive oils determined by UPLCESI-MS/MS. Values expressed as mg compound/kg oil.
Control virgin olive oil
(mg/kg oil)
Enriched olive oil
(mg/kg oil)
Hydroxytyrosol
0.37
6.64
Tyrosol
1.03
8.70
1.40
15.33
Vanillic acid
0.37
3.94
p-coumaric acid
0.08
0.84
Vanillin
0.16
1.44
0.61
6.21
3,4-DHPEA-EDA
45.42
527.84
3,4-DHPEA-EA
15.11
26.21
3,4-DHPEA-AC
52.84
102.46
p-HPEA-EDA
9.72
24.12
123.08
680.62
Pinoresinol
115.8
173.15
Acetoypinoresinol
46.30
78.79
162.1
251.94
Luteolin
1.44
6.28
Apigenin
0.27
0.80
1.71
7.08
288.89
961.17
Phenolic compounds
Total phenyl alcohols
Total phenolic acids
Total secoiridoid derivatives
Total lignans
Total flavonoids
Total phenolic compounds
It is also important to highlight the increase observed in the secoiridoid derivatives
and the flavonoid group. The importance of the secoiridoid derivatives is based on
their chemical structure. These compounds are precursors of phenyl alcohols, which,
as was stated above, are very active compounds. In addition, recent studies have
demonstrated that some secoiridoid derivatives, such as 3,4-DHPEA-EDA, are even
better at protecting red blood cells (RBCs) from oxidative damages than
hydroxytyrosol (Paiva-Martins et al., 2009). Therefore, the secoiridoid derivatives are
valuable compounds that could have a beneficial effect in the organism. On the other
256
hand, flavonoids are the most widespread natural phenolic compounds whose
important activity is due to their characteristic triple aromatic ring chemical structure.
However, their concentration in virgin olive oil is very low compared with that
obtained from other phenolic sources. Thus increasing the amount of flavonoids in
olive oils is of interest to increase their intake from this source.
Therefore, the greater concentration of phenolic compounds in the enriched oils is
expected to increase the level of their corresponding metabolites in human plasma
after consumption of the oils, due to the higher amount available to be absorbed by the
organism.
3.2. Phenol metabolites identification and quantification in human plasma
The phenolic compounds and their corresponding metabolites in the plasma
samples after ingestion of either the control or enriched olive oil were identified and
quantified following the procedure described by Suarez et al (2009b). Table 33 shows
the main chromatographic peaks that appeared in the chromatograms. On the basis of
their retention time, corresponding molecular weight and ion transition, and the
information obtained from the literature, we proposed which phenolic compounds and
metabolites could match these peaks. Some of the compounds had more than one
chromatographic peak, appearing at different retention times but maintaining the
molecular weight and the mass spectrometric fragments. This suggests the existence of
several isomerical forms of these compounds in the plasma samples.
As expected, most of the metabolites identified in the plasma were derived from
the secoiridoids and phenyl alcohol groups and appeared in their conjugated form,
especially sulphated and glucuronidated. This could suggest that basically the phenolic
compounds from olive oil follow two different pathways: one mediated by the action
of the sulphotransferase enzymes and the other governed by the glucurotransferases.
This result agrees with the ones obtained by others authors, such as De la Torre-Carbot
et al. (20006) who identified hydroxytyrosol and tyrosol in their glucuronidated and
sulphated forms in human low-density lipoproteins (LDL) after the intake of virgin
olive oil.
The chromatographic analysis of the plasma samples also revealed the existence of
other compounds (either conjugated or in their free form), including phenolic acids
(hydroxybenzoic, hydroxyphenylacetic, ferulic and caffeic acids and their derivatives)
and flavonoids (apigenin glucuronide).
257
Table 33. Chromatographic parameters of the main peaks observed in the plasma
samples after ingestion of the olive oils.
Peak
Rt (min)
[M-H]-
1
2
3
4
5
6
7
8
9
10
11
12
13
137
151
151
167
179
181
197
217
230
231
233
243
245
14
15
16
17
18
3.62; 10.65
4.63, 6.52
6.55
4.85
5.17
17.1
10.14
8.55; 19.15
5.06; 7.98; 12.45
9.32; 14.11
6.15
6.67; 13.5; 21.75
11.77; 16.86;
19.3
10.05
19.15; 23.83
9.48
11.27
4.56; 6.74
Fragments
MS/MS
93
107
136
123
135
137
153
137
150
151, 136
153, 123
163, 119
165
247
259
261
273
327
167, 123
179, 135
181
193, 134
150
19
20
21
8.77; 18.97
7.00
10.57
327
369
373
151, 136
193, 134
197
22
23
15.15
10.69; 13.24
445
495
269
319, 153
Proposed structure
Hydroxybenzoic acid
Hydroxyphenylacetic acid
Vanillin
Vanillic acid
Caffeic acid
Homovanillic acid derivative
3,4-DHPEA-EA derivative
Tyrosol sulphate
4-methoxy-phenylethanol sulphate
Vanillin sulphate
Hydroxytyrosol sulphate
Coumaric acid sulphate
4-methoxy-phenylacetic acid
sulphate
Vanillic acid sulphate
Caffeic acid sulphate
Homovanillic acid sulphate
Ferulic acid sulphate
4-methoxy-phenylethanol
glucuronide
Vanillin glucuronide
Ferulic acid glucuronide
glucuronide
Apigenin glucuronide
3,4-DHPEA-EDA glucuronide
With regard to the metabolites derived from hydroxytyrosol, the appearance of
compounds structurally related to homovanillic acid suggests the existence of a
methylation process in the organism, probably due to the activity of the enzyme
cathecol-O-methyltransferase (COMT). D’Angelo et al. (2001) proposed a metabolic
pathway for hydroxytyrosol in which the action of this enzyme promoted the
appearance of homovanillic acid and its conjugated forms. In the case of the plasma
samples obtained after the ingestion of both control and enriched olive oil, we were
able to identify the metabolites that appear at the end of this chain of reactions:
hydroxytyrosol sulphate, homovanillic acid derivative and homovanillic acid sulphate.
Homovanillic acid derivative was a compound that presented the same precursor and
product ions as homovanillic acid but eluted at a different retention time from the
commercial standard. The non-identification of free hydroxytyrosol and the other
intermediate forms may suggest that these compounds are rapidly subjected to the
258
activity of the enzymes, originating the sulphated or methyl-sulphated forms which are
more likely to be absorbed by the organism. Figure 41 shows the metabolic pathway
of hydroxytyrosol proposed by D’angelo et al (2001) with some variations, indicating
in bold the metabolites identified in the plasma samples after the ingestion of olive oil.
OH
Hydroxytyrosol
sulphate
O
O
S
O
Sulphoconjugated
derivative
OH
OH
SULT
OH
OH
OH
SULT
O
CH3
Hydroxytyrosol
(4-hydroxy-3-methoxyphenylethanol)
OH
Alcohol
dehydrogenase
MOPET
COMT
(3,4-dihydroxyphenylethanol)
DOPAC
reductase
OH
Aldehyde
reductase
OH
O
OH
OH
OH
OH
Aldehyde
dehydrogenase
COMT
(4-hydroxy-3-methoxyphenylacetaldehyde)
DOPAC
HO
O
SULT
MOPAL
O
DOPAL
(3,4-dihydroxyphenylacetaldehyde)
O
(3,4-dihydroxyphenylacetic acid)
OH
O
SULT
O
O
Sulphoconjugated
derivatives
CH3
S
CH3
OH
Homovanillic acid
O
O
(4-hydroxy-3-methoxyphenylacetic acid)
HO
CH3
O
SULT
HO
O
Homovanillic
acid sulphate
Homovanillic
acid derivative
Figure 41. Metabolic pathways of hydroxytyrosol (adapted from D’Angelo et al.,
2001). The chemical structures in bold were identified in the plasma samples after
olive oil ingestion. SULT: sulphotransferase; COMT: cathecol-O-methyltransferase.
Similarly to the metabolic pathway described in hydroxytyrosol, the analysis of the
plasma samples revealed the existence of some methylated metabolites that probably
259
originated from tyrosol. Thus peaks 9, 13 and 18 in Table 33 could be formed from
tyrosol, with an analogous chemical structure to the one obtained as a result of the
activity of COMT on hydroxytyrosol. Peak 9 is equivalent to MOPET sulphate, peak
13 is equivalent to the homovanillic sulphate and peak 18 was the result of the
glucuronidation of the analogue structure of MOPET in tyrosol.
O
OH
S
O
O
O
4-methoxyphenylethanol
glucuronide
Tyrosol
sulphate
OH
O
O
O
sulphate
OH
SULT
Tyrosol
Alcohol
dehydrogenase
OH
Methylation
OH
OH
O
CH3
Aldehyde
reductase
OH
4-methoxyphenylacetaledhyde
Aldehyde
dehydrogenase
O
OH
CH3
SULT
OH
S
4-hydroxyphenylacetaldehyde
4-hydroxyphenylacetic
acid
HO
O
Methylation
O
O
SULT
CH3
O
SULT
O
S
O
Sulphoconjugated
derivatives
OH
HO
SULT
HO
O
O
4-methoxyphenylacetic
acid
4-methoxyphenylacetic
acid sulphate
Figure 42. Proposed metabolic pathways of tyrosol. The chemical structures in black
were identified in the plasma samples after olive oil ingestion. SULT:
sulphotransferase.
These results contrast to those obtained by Garcia-Villalba et al. (2010) who did
260
not identify methyl conjugates metabolites from tyrosol in urine samples after the
ingestion of 50 mL of virgin olive oil. They attributed this to the lack of activity of
COMT on this compound due to the need for an ortho diphenolic structure of this
enzyme. The appearance of the methylated compounds in the plasma samples in the
present study could suggest the presence of enzymatic activity able to methylate
tyrosol. Thus, Figure 42 shows the proposed metabolic pathways that tyrosol could
undergo in the organism, highlighting in bold the metabolites identified in the plasma
samples after consumption of the virgin olive oil. Based on the pathway described by
D’Angelo et al. (2001), we hypothesized that tyrosol could also be affected by the
activity of alcohol dehydrogenase and aldehyde reductase although the metabolites
produced by the activity of these enzymes were not found. This could be due to the
high instability of these compounds and the possible preference for methylation.
3.3. Pharmacokinetic parameters of phenol metabolites
The concentration of the phenolic compounds and their metabolites in the plasma
samples was monitored 0, 60, 120, 240 and 300 min after the ingestion of the olive oil
and the difference between their bioavailability depending on the olive oil consumed
(control or phenol-enriched) was evaluated.
In general, the data revealed that the amount of phenolic metabolites in the plasma
samples obtained after the ingestion of the phenol-enriched olive oil was higher than
that obtained after intake of the control olive oil (without phenol enrichment). Tables
34 and 35 show the pharmacokinetic parameters obtained after analyzing the
chromatographic results with the PK functions software. This software allows us to
tentatively determine the value of the maximum concentration of the compounds in
the plasma (Cmax) and the area under the curve in the interval of study (AUC).
As can be seen in Table 34, almost all the identified compounds that are involved
in the hydroxytyrosol pathway reached higher concentrations in plasma samples
obtained after the ingesta of phenol-enriched olive oil compared with the values
obtained after the intake of control oil. This suggests that, effectively, the enrichment
of the olive oil with the phenol extract successfully produced an increase in the
concentration of these compounds in plasma after oil consumption. This is desirable as
a way to achieve a concentration of phenol metabolites in plasma able to produce a
real effect in the organism. However, the variability of the results between the
different volunteers was very high, as can be seen in the AUC range. This is because
the bioavailability of phenolic compounds not only depends on their concentration in
the oil, but is also affected by each individual’s characteristic parameters, such as their
261
enzymatic activity and habitual diet. Thus, despite the mean values being higher after
consuming phenol-enriched olive oil, only the concentration of hydroxytyrosol
sulphate was statistically higher than in the control.
Table 34. Pharmacokinetic parameters for the metabolites derived from the
secoiridoids in plasma samples after the intake of either control or enriched olive oil.
Phenolic compound
Hydroxytyrosol sulphate
Homovanillic acid
derivative
Homovanillic acid sulphate
3,4-DHPEA-EDA
glucuronide
glucuronide
Tyrosol sulphate
4-methoxy-phenylacetic
acid sulphate
sulphate
glucuronide
Oil
Cmax
AUC
AUC range
(µ
µmoles/L) (µ
µmoles*min/L) (µ
µmoles*min/L)
Control
0.53
111
50-238
Enriched
0.76
159
93-287
Control
0.47
132
80-246
Enriched
0.32
80
63-102
Control
0.67
177
83-330
Enriched
0.75
169
55-282
Control
0.24
58
26-127
Enriched
0.20
54
26-111
Control
0.33
75
5-235
Enriched
0.48
98
7-245
Control
0.03
6
2-14
Enriched
0.22
34
3-96
Control
0.92
228
59-601
Enriched
0.87
240
73-538
Control
3.11
840
249-1,891
Enriched
2.18
565
46-2,024
Control
2.32
617
119-1,256
Enriched
2.25
611
106-2,054
Control
0.03
7
2-9
Enriched
0.03
6
3-9
p<
0.05
n.s.
n.s.
n.s.
n.s.
n.s.
n.s.
n.s.
n.s.
n.s.
On the other hand, although in all the cases an increase in the concentration of the
peaks for the tyrosol metabolites was detected after consumption of both control and
phenol-enriched oils, no significant differences between these oils were observed. In
addition, the mean values were very similar, suggesting that the bioavailability of
these compounds was not affected by the phenol enrichment.
262
Table 35. Pharmacokinetic parameters for the metabolites derived from the phenolic
acids and the lignans in plasma samples after the intake of either control or enriched
olive oil.
Phenolic compound
Apigenin glucuronide
Hydroxybenzoic acid
Hydroxyfenilacetic acid
Vanillic acid
Vanillic acid sulphate
Caffeic acid
Caffeic acid sulphate
Coumaric acid sulphate
Vanillin
Vanillin sulphate
Vanillin glucuronide
Ferulic acid derivative
Ferulic acid derivative
sulphate
Ferulic acid glucuronide
Oil
Cmax
AUC
AUC range
(µ
µmoles/L) (µ
µmoles*min/L) (µ
µmoles*min/L)
Control
0.06
16
8-35
Enriched
0.06
16
8-36
Control
1.63
438
128-933
Enriched
1.84
470
72-923
Control
4.28
1134
185-2,454
Enriched
4.99
1316
172-2,507
Control
5.39
1254
824-1,821
Enriched
2.42
538
368-700
Control
0.63
137
32-416
Enriched
0.75
174
75-232
Control
3.28
798
284-1,885
Enriched
4.69
959
355-2,094
Control
0.88
226
19-477
Enriched
2.51
357
32-1,818
Control
0.83
222
63-533
Enriched
1.16
271
89-750
Control
1.25
126
19-245
Enriched
2.10
302
42-1,014
Control
9.61
2693
718-6,563
Enriched
20.94
5161
1,711-10,800
Control
0.42
105
46-327
Enriched
0.26
61
31-172
Control
0.26
70
49-131
Enriched
0.21
51
39-71
Control
4.20
919
154-3,245
Enriched
5.71
1257
454-2,575
Control
0.50
119
19-214
Enriched
0.70
189
23-413
n.s.
n.s.
n.s.
n.s.
n.s.
n.s.
n.s.
n.s.
n.s.
p<
0.05
n.s.
n.s.
n.s.
n.s.
263
Regarding the metabolites originated from phenolic acids, it could be considered
that the compounds that appeared in basal conditions are fermentation products,
generated through the effect of the human gut microbiota on the dietary fiber and
some phenolic compounds, such as flavonoids, in the habitual diet of the volunteers
(Aura et al., 2008). Once the olive oil has been ingested, the increase in the
concentration of the phenolic acid metabolites in the plasma over time could be partly
attributed to the absorption of this fraction included in the olive oil. However, the
enrichment of the olive oil with the phenolic extract also increases the concentration
of the flavonoid group and it is possible that this could generate a further increase in
the concentration of the phenolic acid metabolites once the human gut microbiota act
on them. Therefore, in addition to the direct effect on the content of the phenolic acid
metabolites observed in the plasma during the period of study it is possible that an
indirect increase occurs through the fermentation of the flavonoids in the colon.
Nevertheless, further studies would be needed to confirm this.
It is also remarkable that a certain shift of the time when the maximum
concentration of some of the identified metabolites was reached was observed as a
consequence of the phenol-enrichment of the oil. As an example, Figure 43 shows the
graphic evolution of the concentration of some metabolites from the different phenolic
groups identified in the plasma after the intake of both the control and enriched olive
oil: hydroxytyrosol sulphate (phenyl alcohol), 3,4-DHPEA-EA derivative glucuronide
(secoiridoid), apigenin glucuronide (flavonoid) and ferulic acid glucuronide (phenolic
acid). After consumption of the control olive oil, the maximum concentration of these
peaks was reached at 60 min. However, consumption of the phenol-enriched olive oil
shifted this maximum to 120 min. This could be due to the higher concentration
leading to a certain saturation of the mechanisms involved in the absorption and
transport of these compounds in the human organism. Therefore, the phenol-enriched
oil needs more time to reach the maximum concentration in the plasma.
In addition to this change in the time to reach the highest concentration, there was a
general quantitative increment in the value of these metabolites in the plasma after the
ingesta of the phenol-enriched olive oil compared with the one obtained after
consumption of the control oil. This is of great importance and points to the suitability
of phenol-enrichment of the oil as a means of increasing the amount of these desirable
compounds in the organism, which is necessary to produce a real effect on the
development of some types of cancers, such as colon cancer (Colomer and Menendez,
2006).
264
0.8
0.25
µmoles/L
a
µmoles/L
0.6
0.4
0.2
b
0.2
0.15
0.1
0.05
0
0
0
50
100
150
200
250
300
0
50
100
min
c
0.07
0.06
µmoles/L
µ moles/L
0.05
0.04
0.03
0.02
0.01
0
0
50
100
150
min
200
250
300
150
min
200
250
0.8
0.7
0.6
0.5
0.4
0.3
0.2
0.1
0
300
d
0
50
100
150
200
250
min
Figure 43. Pharmacokinetics of (a) hydroxytyrosol sulphate, (b) 3,4-DHPEA-EA
derivative glucuronide, (c) apigenin glucuronide and (d) ferulic acid glucuronide in
human plasma after the intake of control ( ) and phenol-enriched olive oil ( ).
Analyzing the pharmacokinetic parameters of the different groups of phenolic
compounds under study their different pattern of absorption could be evaluated. To
start with, the time when the maximum concentration is reached suggests that their
absorption occurs approximately in the small intestine after being subjected to the
strong metabolism of the organism. Thus, hydroxytyrosol sulphate (and by extension
the other phenyl alcohols metabolites) could come from the high spectra of secoiridoid
derivatives in the oil by hydrolysis in the stomach (phase I metabolism) and later
conjugation by action of the sulphotransferases (phase II). As was reported in our
previous study (Suarez et al., 2010) after simulated in vitro digestion of virgin olive oil
there was a significant increment in hydroxytyrosol in the stomach (rising by
approximately 70%) due to the acidic conditions of the media (pH 2). This can be
related to the high proportion of phenyl alcohols conjugated as their different
metabolites that appeared in the plasma. The absorption of phenolic acid metabolites
seems to follow the same pattern.
On the other hand, the appearance of 3,4-DHPEA-EA derivative and its
glucuronide form seems to suggest that some of the secoiridoids in the oil are able to
resist the strong conditions of the digestion process and reach the blood stream in a
265
300
chemical form higher than hydroxytyrosol. This is of great importance due to the
healthy effects that these compounds could exert (Paiva-Martins et al., 2009).
The non-identification of any metabolic form derived from lignans in the plasma
could be due to their degradation by the colonic flora of the gut and further
transformation into enterodiol and enterolactona. This process is believed to take place
in the period of 8-10 hours after ingestion (Kuijsten et al., 2005).
4. Conclusions
The enrichment of the olive oil with an olive-cake extract increased the amount of
the phenolic compounds in the resulting oil and had a direct influence on their
bioavailability. The in vivo study showed that the concentration of almost all the
compounds was higher in the plasma samples from the phenol-enriched olive oil than
after ingestion of the control oil, demonstrating the suitability of the enrichment. In
general, a displacement of the time to reach the maximum concentration is observed in
the samples, which indicates that more time is needed to absorb the higher phenolic
content. However, the inter-individual variability in the concentration of the plasma
phenol metabolites means it is difficult to show statistically significant differences
between the control (virgin olive oil) and enriched olive oils. This could be due to the
high number of variables that interfere in the absorption of these compounds and
suggests that the metabolism of phenols is affected firstly by the individual. These
preliminary results suggest the need for a major interventional study with a larger
number of volunteers to confirm the effectiveness of the enrichment of the olive oil at
increasing the plasma concentration of the phenol metabolites.
5. Acknowledgements
This work was supported by the Spanish Ministry of Education and Science
financing the projects AGL2005-07881-C02-01/ALI and AGL2005-07881-C0202/ALI; and the grant received by Manuel Suarez (BES-2006-14136).
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Obtenciyn de extractos fenylicos a partir de subproductos de la oliva

Transcription

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