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Sylvain Guyot - One of the best experts on this subject based on the ideXlab platform.
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Detailed polyphenol and tannin composition and its variability in tunisian dates (Phoenix dactylifera L.) at different maturity stages
Journal of Agricultural and Food Chemistry, 2013Co-Authors: Hedi Hammouda, Jamila Kalthoum Cherif, Malika Trabelsi-ayadi, Alain Baron, Sylvain GuyotAbstract:The polyphenol profile of two Tunisian varieties of dates including flavanols, flavonols, flavones, and hydroxycinnamates was characterized. Three tissue zones (flesh, peel, and stone) and three maturity stages were considered. Phenolic compounds were analyzed using reversed phase high-performance liquid chromatography coupled to UV-visible and electrospray mass spectrometry. Procyanidin oligomers and polymers were characterized and quantified using phloroglucinolysis prior to HPLC analysis. Procyanidin polymers based on (-)-epicatechin structure were by far the most concentrated polyphenols in ripe dates, accounting for 95% of total polyphenols with an average concentration of 14 g/kg in the fresh edible parts of the fruit. Interestingly, Procyanidins were also highly concentrated in the stones. The concentration and average degree of polymerization (DPn) of the Procyanidins decreased according to maturity. Other phenolics, including caffeoylshikimic acid hexoside, caffeoyl-sinapoyl monohexoside and dihexoside, and acetylated flavonols, were tentatively identified for the first time in the fruit.
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Characterization of procyanidin B2 oxidation products in an apple juice model solution and confirmation of their presence in apple juice by high-performance liquid chromatography coupled to electrospray ion trap mass spectrometry.
Journal of Mass Spectrometry, 2011Co-Authors: Pascal Poupard, Philippe Sanoner, Sylvain Guyot, Alain Baron, Catherine RenardAbstract:a * Procyanidins (i.e. condensed tannins) are polyphenols commonly found in fruits. During juice and cider making, apple poly-phenol oxidase catalyzes the oxidation of caffeoylquinic acid (CQA) into its corresponding o-quinone which further reacts with Procyanidins and other polyphenols, leading to the formation of numerous oxidation products. However, the structure and the reaction pathways of these neoformed phenolic compounds are still largely unknown. Experiments were carried out on a model system to gain insights into the chemical processes occurring during the initial steps of fruit processing. Procyanidin B2 was oxidized by caffeoylquinic acid o-quinone (CQAoq) in an apple juice model solution. The reaction products were monitored using high performance liquid chromatography (HPLC) coupled to ultraviolet (UV)-visible and electrospray tandem mass spectrometry (ESI-MS/MS) in the negative mode. Oxidative conversion of procyanidin B2 ([M-H] À at m/z 577) into procyanidin A2 at m/z 575 was unambiguously confirmed. In addition, several classes of products were characterized by their deprotonated molecules ([M-H] À) and their MS/MS fragmentation patterns: hetero-dimers (m/z 929) and homo-dimers (m/z 1153 and 705) resulting from dimerization involving procyanidin and CQA molecules; intramolecular addition products at m/z 575, 573, 927, 1151 and 703. Interestingly, no extensive polymerization was observed. Analysis of a cider apple juice enabled comparison with the results obtained on a biosynthetic model solution. However, procyanidin A2 did not accumulate but seemed to be an intermediate in the formation of an end-product at m/z 573 for which two structural hypotheses are given. These structural modifications of native polyphenols as a consequence of oxidation probably have an impact on the organoleptic and nutritional properties of apple juices and other apple-derived foods.
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Biotransformation of Procyanidins by a purified fungal dioxygenase : identification and characterization of the products using mass spectrometry
Process Biochemistry, 2010Co-Authors: Roopesh Krishnankutty, Sylvain Guyot, Abdulhameed Sabu, M. Haridas, Isabelle Perraud Gaime, Roussos SevastianosAbstract:Procyanidins commonly known as condensed tannins are a type of polyphenol with wide abundance naturally. They are commonly known as potent anti-oxidants with powerful free radical scavenging activity as well as anti-tumor-promoting activity. Little is known about the enzymatic mechanisms/pathways involved in the microbial biotransformation of these polyphenolic molecules. The extracellular enzyme, dioxygenase produced by Aspergillus fumigatus was used as in vitro tools to study the degradation pathway of a model procyanidin dimer, namely procyanidin B2. The enzyme was purified to homogeneity by a two step process of anion-exchange chromatography coupled with FPLC followed by gel-filtration chromatography coupled with HPLC and the molecular mass estimated. In addition, the different biotransformed products resulted from the dioxygenase action on PB2 were purified using Reversed-Phase-High Performance Liquid Chromatography prior to their identification and characterization by structural elucidation using Electrospray Ionization-Mass Spectrometry. Subsequently, the mechanism of dioxygenase action on procyanidin dimer was defined.
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Potentiation of apple procyanidin-triggered apoptosis by the polyamine oxidase inactivator MDL 72527 in human colon cancer-derived metastatic cells
International Journal of Oncology, 2006Co-Authors: Francine Gossé, Sylvain Guyot, Stamatiki Roussi, Angèle Schoenfelder, André Mann, Jean-pierre Bergerat, Nikolaus Seiler, Françis RaulAbstract:Apple Procyanidins have chemopreventive properties in a model of colon cancer, they affect intracellular signalling pathways, and trigger apoptosis in a human adenocarcinoma-derived metastatic cell line (SW620). In the present study we investigated relationships between procyanidin-induced alterations in polyamine metabolism and apoptotic effects. Apple Procyanidins diminish the activities of ornithine decarboxylase and S-adenosyl-L-methionine decarboxylase, key enzymes of polyamine biosynthesis, and they induce spermidine/spermine N1-acetyltransferase, which initiates retroconversion of poly-amines. As a consequence of the enzymatic changes polyamine concentrations are diminished, and N1-acetyl-polyamines accumulate in SW620 cells. In contrast with expectations MDL 72527, an inactivator of polyamine oxidase (PAO), improved the anti-proliferative effect of Procyanidins, and caused an increase of the proportion of apoptotic cells, although it prevented the formation of hydrogen peroxide and 3-acetamidopropanal, the cytotoxic products of PAO-catalysed degradation of N1-acetylspermidine and N1-acetylspermine. Addition of 500 µM N1-acetylspermidine to the culture medium in the presence of Procyanidins mimicked the effect of MDL 72527. Therefore we presume that the enhanced procyanidin-triggered apoptosis by MDL 72527 is mediated by the accumulation of N1-acetyl-polyamines. The observation that apple Procyanidins enhance polyamine catabolism and reduce polyamine biosynthesis activity similar to known inducers of SSAT, without sharing their toxicity, and the potentiation of these effects by low concentrations of MDL 72527 suggests apple Procyanidins for chemopreventive and therapeutic interventions.
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inhibition of apple polyphenol oxidase activity by Procyanidins and polyphenol oxidation products
Journal of Agricultural and Food Chemistry, 2004Co-Authors: Carine Le Bourvellec, Jeanmichel Le Quere, Philippe Sanoner, Jeanfrancois Drilleau, Sylvain GuyotAbstract:The rate of consumption of dissolved oxygen by apple polyphenol oxidase in cider apple juices did not correlate with polyphenol oxidase activity in the fruits and decreased faster than could be explained by the decrease of its polyphenolic substrates. The kinetics parameters of a crude polyphenol oxidase extract, prepared from apple (Braeburn cultivar), were determined using caffeoylquinic acid as a substrate. Three apple procyanidin fractions of n 80, 10.5, and 4 were purified from the parenchyma of cider apples of various cultivars. Procyanidins, caffeoylquinic acid, (−)-epicatechin, and a mixture of caffeoylquinic acid and (−)-epicatechin were oxidized by reaction with caffeoylquinic acid o-quinone in order to form oxidation products. All the fractions were evaluated for their inhibitory effect on PPO activity. Native Procyanidins inhibited polyphenol oxidase activity, the inhibition intensity increasing with n. The polyphenol oxidase activity decreased by 50% for 0.026 g/L of the fraction of n 80, 0.1...
Ronald L Prior - One of the best experts on this subject based on the ideXlab platform.
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release of bound Procyanidins from cranberry pomace by alkaline hydrolysis
Journal of Agricultural and Food Chemistry, 2010Co-Authors: Brittany L White, Luke R Howard, Ronald L PriorAbstract:Procyanidins in plant products are present as extractable or unextractable/bound forms. We optimized alkaline hydrolysis conditions to liberate Procyanidins and depolymerize polymers from dried cranberry pomace. Alkaline extracts were neutralized (pH 6−7) and then Procyanidins were extracted with ethyl acetate and analyzed by normal phase high performance liquid chromatography. Alkaline hydrolysis resulted in an increase in low molecular weight Procyanidins, and the increase was greater at higher temperature, short time combinations. The most Procyanidins (DP1−DP3) were extracted at 60 °C for 15 min with each concentration of NaOH. When compared to conventional extraction using homogenization with acetone/water/acetic acid (70:29.5:0.5 v/v/v), treatment with NaOH increased procyanidin oligomer extraction by 3.8−14.9-fold, with the greatest increase being DP1 (14.9×) and A-type DP2 (8.4×) Procyanidins. Alkaline treatment of the residue remaining after conventional extraction resulted in further procyanidin...
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effect of heating on the stability of grape and blueberry pomace Procyanidins and total anthocyanins
Food Research International, 2010Co-Authors: Ramesh C Khanal, Luke R Howard, Ronald L PriorAbstract:Abstract Fruit by-products are rich sources of Procyanidins and anthocyanins known for potential health benefits. Freeze dried blueberry pomace and grape pomace were heated in a forced air oven at 40, 60, 105, and 125 °C for 72, 48, 16, and 8 h respectively, to study the stability of Procyanidins and total anthocyanins. Heating decreased procyanidin concentrations significantly ( p p > 0.05) loss when heated at 40 °C. Total anthocyanin loss was highest at 125 °C for both blueberry (52%) and grape pomace (70%). Results suggested that while heating at lower temperatures for up to 3 days may not be detrimental, heating at higher temperatures for more than 8 h results in considerable loss of both the compounds.
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processing of sorghum sorghum bicolor and sorghum products alters procyanidin oligomer and polymer distribution and content
Journal of Agricultural and Food Chemistry, 2003Co-Authors: Joseph M Awika, Linda Dykes, Liwei Gu, And Lloyd W Rooney, Ronald L PriorAbstract:Sorghum Procyanidins were characterized and quantified from two brown sorghum varieties and their processed products by normal phase HPLC with fluorescence detection. The DP of the Procyanidins was determined by thiolysis. Quantification was done by using purified oligomeric and polymeric cocoa Procyanidins as external standards. Sorghum Procyanidins were composed mostly of high MW (DP > 10) polymers. Significant differences were observed in levels as well as distribution of the different MW Procyanidins between the sorghums. Processing of the sorghum brans into cookies and bread significantly reduced the levels of Procyanidins; this effect was more pronounced in the higher MW polymers. Cookies had a higher retention of Procyanidins (42−84%) than bread (13−69%). Extrusion of sorghum grain resulted in an increase in the levels of procyanidin oligomers with DP ≤ 4 and decrease in polymers with DP ≥ 6. This suggests a possible breakdown of the high MW polymers to the lower MW constituents during extrusion. P...
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identification of Procyanidins and anthocyanins in blueberries and cranberries vaccinium spp using high performance liquid chromatography mass spectrometry
Journal of Agricultural and Food Chemistry, 2001Co-Authors: Ronald L Prior, Sheryl A Lazarus, Guohua Cao, Helen U Muccitelli, John F HammerstoneAbstract:Blueberries and cranberries were analyzed for Procyanidins using normal-phase HPLC/MS. Monomers, identified as (+)-catechin and (−)-epicatechin, and a series of oligomers were detected in blueberries, and MS data confirmed that the oligomers consisted of (epi)catechin units that were exclusively singly linked (B-type). The procyanidin “fingerprints” were similar for Tifblue and Rubel but higher than that for lowbush blueberries. In whole cranberries, (−)-epicatechin was present, along with a complex series of oligomers. Both A-type (contained only one double linkage per oligomer) and B-type oligomers were present. Two commercial cranberry juices exhibited similar procyanidin profiles, except that one contained increased quantitites. There were processing effects on the procyanidin content of cranberry extract and juices when compared to those of the unprocessed fruits. Monomer, dimers, and A-type trimers were the primary Procyanidins, with only trace levels of the B-type trimers and A-type tetramers and w...
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hplc method for the quantification of Procyanidins in cocoa and chocolate samples and correlation to total antioxidant capacity
Journal of Agricultural and Food Chemistry, 1999Co-Authors: Gary E Adamson, Sheryl A Lazarus, John F Hammerstone, Ronald L Prior, Guohua Cao, Alyson E Mitchell, Pieter H Jacobs, Bart G Kremers, Robert B Rucker, Karl A RitterAbstract:Monomeric and oligomeric Procyanidins present in cocoa liquors and chocolates were separated and quantified in four different laboratories using a normal-phase high-performance liquid chromatography (HPLC) method with fluorescence detection. Procyanidin standards through decamers were obtained by extraction from cocoa beans, enrichment by Sephadex LH-20 gel permeation chromatography, and final purification by preparative normal-phase HPLC. The purity of each oligomeric fraction was assessed using HPLC coupled to mass spectrometry. A composite standard was then prepared, and calibration curves were generated for each oligomeric class using a quadratic fit of area sum versus concentration. Results obtained by each of the laboratories were in close agreement, which suggests this method is reliable and reproducible for quantification of Procyanidins. Furthermore, the procyanidin content of the samples was correlated to the antioxidant capacity measured using the ORAC assay as an indicator for potential biological activity.
Toshihiko Shoji - One of the best experts on this subject based on the ideXlab platform.
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apple Procyanidins induce tumor cell apoptosis through mitochondrial pathway activation of caspase 3
Carcinogenesis, 2007Co-Authors: Tomisato Miura, Toshihiko Shoji, Tomomasa Kanda, Yasuyuki Ohtake, Mitsuru Chiba, Kousuke Kasai, Hiroyuki Nozaka, Toshiya Nakamura, Tatsusuke SatoAbstract:Various epidemiologic and experimental in vivo and in vitro studies have suggested that polyphenols derived from fruits, vegetables and beverages might decrease the risk of developing lifestyle diseases, such as cardiovascular disorders and cancer. Apples are a major dietary source of polyphenols. Here we investigated the antitumor activity of apple polyphenols (APs) and Procyanidins, namely condensed tannins, both in vitro and in vivo studies. APs and Procyanidins inhibited the growth of transplanted B16 mouse melanoma cells and BALB-MC.E12 mouse mammary tumor cells, and increased the survival rate of the host mice-transplanted B16 cells. Among the APs, the apple Procyanidins specifically, rather than other polyphenols such as chlorogenic acid, (-)-epicatechin, phloridzin and procyanidin B2, had a major effect on cell proliferation and induced apoptosis in vitro. The apple Procyanidins increased mitochondrial membrane permeability and cytochrome c release from mitochondria and activated caspase-3 and caspase-9 within the tumor cells. In addition, we separated eight procyanidin fractions according to the degree of polymerization using normal-phase chromatography, and detected strong anti-tumor activity in the procyanidin pentamer and higher degree fractions. Our results indicate that the oral administration of apple Procyanidins inhibits the proliferation of tumor cells by inducing apoptosis through the intrinsic mitochondrial pathway.
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oligomeric Procyanidins in apple polyphenol are main active components for inhibition of pancreatic lipase and triglyceride absorption
Journal of Agricultural and Food Chemistry, 2007Co-Authors: Hiroshi Sugiyama, Toshihiko Shoji, Tomomasa Kanda, Yoko Akazome, Atsuko Yamaguchi, Masaaki Yasue, Yasuyuki OhtakeAbstract:Inhibitory effects of apple polyphenol extract (AP) and procyanidin contained in AP on in vitro pancreatic lipase activity and in vivo triglyceride absorption in mice and humans were examined. AP and procyanidin considerably inhibited in vitro pancreatic lipase activity. However, polyphenols, except for procyanidin, in AP (i.e., catechins, chalcones, and phenol carboxylic acids) showed weak inhibitory activities on pancreatic lipase. Procyanidins separated by normal-phase chromatography according to the degree of polymerization were also examined. Inhibitory effects of Procyanidins increased according to the degree of polymerization from dimer to pentamer. On the other hand, pentamer or greater Procyanidins showed maximal inhibitory effects on pancreatic lipase. These results suggested that with respect to in vitro pancreatic lipase inhibition, the degree of polymerization was an important factor and oligomeric procyanidin mainly contributed. Next, we performed a triglyceride tolerance test in mice and humans. Simultaneous ingestion of AP and triglyceride significantly inhibited an increase of plasma triglyceride levels in both models. These results suggested that the oligomeric Procyanidins contained in AP inhibited triglyceride absorption by inhibiting pancreatic lipase activity in mice and humans.
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oligomeric Procyanidins in apple polyphenol are main active components for inhibition of pancreatic lipase and triglyceride absorption
Journal of Agricultural and Food Chemistry, 2007Co-Authors: Hiroshi Sugiyama, Toshihiko Shoji, Tomomasa Kanda, Yoko Akazome, Atsuko Yamaguchi, Masaaki Yasue, Yasuyuki OhtakeAbstract:Inhibitory effects of apple polyphenol extract (AP) and procyanidin contained in AP on in vitro pancreatic lipase activity and in vivo triglyceride absorption in mice and humans were examined. AP and procyanidin considerably inhibited in vitro pancreatic lipase activity. However, polyphenols, except for procyanidin, in AP (i.e., catechins, chalcones, and phenol carboxylic acids) showed weak inhibitory activities on pancreatic lipase. Procyanidins separated by normal-phase chromatography according to the degree of polymerization were also examined. Inhibitory effects of Procyanidins increased according to the degree of polymerization from dimer to pentamer. On the other hand, pentamer or greater Procyanidins showed maximal inhibitory effects on pancreatic lipase. These results suggested that with respect to in vitro pancreatic lipase inhibition, the degree of polymerization was an important factor and oligomeric procyanidin mainly contributed. Next, we performed a triglyceride tolerance test in mice and hu...
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apple procyanidin oligomers absorption in rats after oral administration analysis of Procyanidins in plasma using the porter method and high performance liquid chromatography tandem mass spectrometry
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Toshihiko Shoji, Saeko Masumoto, Nina Moriichi, Hiroshi Akiyama, Tomomasa Kanda, Yasuyuki Ohtake, Yukihiro GodaAbstract:In this study, we investigated the absorption of apple Procyanidins, namely, apple condensed tannins (ACTs), in rats using the Porter method and high-performance liquid chromatography/tandem mass spectrometry. The apple procyanidin concentrations in the rat plasma reached a maximum 2 h after administration and decreased thereafter. To investigate the limits of the absorption of apple Procyanidins in the polymerization degree, we administered the procyanidin oligomer fraction, which was separated from ACT using normal-phase chromatography according to the degree of polymerization. Procyanidins from each dimer to pentamer group were detected in the plasma by the Porter method. Moreover, by the study using reconstituted Procyanidins, polymeric Procyanidins influenced the absorption of procyanidin oligomers. These results suggest that ACTs are absorbed and directly involved in physiological functions in the rats. Keywords: Absorption; apple Procyanidins; HPLC/MS/MS; procyanidin dimers; procyanidin trimers
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apple procyanidin oligomers absorption in rats after oral administration analysis of Procyanidins in plasma using the porter method and high performance liquid chromatography tandem mass spectrometry
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Toshihiko Shoji, Saeko Masumoto, Nina Moriichi, Hiroshi Akiyama, Tomomasa Kanda, Yasuyuki Ohtake, Yukihiro GodaAbstract:In this study, we investigated the absorption of apple Procyanidins, namely, apple condensed tannins (ACTs), in rats using the Porter method and high-performance liquid chromatography/tandem mass spectrometry. The apple procyanidin concentrations in the rat plasma reached a maximum 2 h after administration and decreased thereafter. To investigate the limits of the absorption of apple Procyanidins in the polymerization degree, we administered the procyanidin oligomer fraction, which was separated from ACT using normal-phase chromatography according to the degree of polymerization. Procyanidins from each dimer to pentamer group were detected in the plasma by the Porter method. Moreover, by the study using reconstituted Procyanidins, polymeric Procyanidins influenced the absorption of procyanidin oligomers. These results suggest that ACTs are absorbed and directly involved in physiological functions in the rats.
Sheryl A Lazarus - One of the best experts on this subject based on the ideXlab platform.
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cocoa Procyanidins are stable during gastric transit in humans
The American Journal of Clinical Nutrition, 2002Co-Authors: Laurent Rios, Richard N Bennett, Sheryl A Lazarus, Christian Rémésy, Augustin Scalbert, Gary WilliamsonAbstract:BACKGROUND Polyphenolic Procyanidins are abundant flavonoid polymers in Western diets. In vitro biological activity has been reported for these compounds, but activity in vivo depends on the amount and chemical nature of the flavonoids reaching the gastrointestinal tract. Degradation of Procyanidins under simulated gastric conditions at pH 2.0 has been reported in vitro. OBJECTIVE The objective was to examine whether depolymerization of Procyanidins occurs in the stomach of human subjects in vivo. DESIGN After an overnight fast, 6 healthy subjects (3 men and 3 women) consumed 500 mL of a cocoa beverage containing 733 mg procyanidin polymers and 351 mg structurally related flavanol monomers. With the use of a nasogastric tube, stomach contents were collected every 10 min after beverage ingestion until the stomach was emptied. Flavanols and Procyanidins (up to pentamers) were quantified by normal and reversed-phase HPLC. RESULTS In all subjects, gastric transit lasted approximately 50-60 min. No change in the HPLC profile of Procyanidins was observed during this period, showing that Procyanidins were remarkably stable in the stomach environment. CONCLUSION The results suggest that most ingested Procyanidins reach the small intestine intact and are available for absorption or metabolism.
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Cocoa Procyanidins are stable during gastric transit in humans
The American Journal of Clinical Nutrition, 2002Co-Authors: Laurent Rios, Richard N Bennett, Sheryl A Lazarus, Christian Rémésy, Augustin Scalbert, Gary WilliamsonAbstract:Background: Polyphenolic Procyanidins are abundant flavonoid polymers in Western diets. In vitro biological activity has been reported for these compounds, but activity in vivo depends on the amount and chemical nature of the flavonoids reaching the gastrointestinal tract. Degradation of Procyanidins under simulated gastric conditions at pH 2.0 has been reported in vitro. Objective: The objective was to examine whether depolymerization of Procyanidins occurs in the stomach of human subjects in vivo. Design: After an overnight fast, 6 healthy subjects (3 men and 3 women) consumed 500 mL of a cocoa beverage containing 733 mg procyanidin polymers and 351 mg structurally related flavanol monomers. With the use of a nasogastric tube, stomach contents were collected every 10 min after beverage ingestion until the stomach was emptied. Flavanols and Procyanidins (up to pentamers) were quantified by normal and reversed-phase HPLC. Results: In all subjects, gastric transit lasted 50-60 min. No change in the HPLC profile of Procyanidins was observed during this period, showing that Procyanidins were remarkably stable in the stomach environment. Conclusion: The results suggest that most ingested Procyanidins reach the small intestine intact and are available for absorption or metabolism.
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procyanidin dimer b2 epicatechin 4β 8 epicatechin in human plasma after the consumption of a flavanol rich cocoa
The American Journal of Clinical Nutrition, 2002Co-Authors: Roberta R Holt, Cesar G. Fraga, Sheryl A Lazarus, John F Hammerstone, Harold H Schmitz, Cameron M Sullards, Derek D Schramm, Carl L KeenAbstract:Background: Epidemiologic studies have linked flavonoid-rich foods with a reduced risk of cardiovascular mortality. Some cocoas are flavonoid-rich and contain the monomeric flavanols (� )-epicatechin and (+)-catechin and oligomeric Procyanidins formed from these monomeric units. Both the monomers and the oligomers have shown potential in favorably influencing cardiovascular health in in vitro and preliminary clinical studies. Although previous investigations have shown increasing concentrations of (� )-epicatechin in human plasma after cocoa consumption, no information is available in the published literature regarding the presence of Procyanidins in human plasma. Objective: This study sought to determine whether Procyanidins can be detected and quantified in human plasma after acute consumption of a flavanol-rich cocoa. Design: Peripheral blood was obtained from 5 healthy adult subjects before (baseline, 0 h) and 0.5, 2, and 6 h after consumption of 0.375 g cocoa/kg body wt as a beverage. Plasma samples were analyzed for monomers and Procyanidins with the use of reversedphase HPLC with coulometric electrochemical array detection and liquid chromatography‐tandem mass spectrometry. Results: Procyanidin dimer, (� )-epicatechin, and (+)-catechin were detected in the plasma of human subjects as early as 0.5 h (16 ± 5 nmol/L, 2.61 ± 0.46 � mol/L, and 0.13 ± 0.03 � mol/L, respectively) after acute cocoa consumption and reached maximal concentrations by 2 h (41 ± 4 nmol/L, 5.92 ± 0.60 � mol/L, and 0.16 ± 0.03 � mol/L, respectively). Conclusion: Dimeric Procyanidins can be detected in human plasma as early as 30 min after the consumption of a flavanol-rich food such as cocoa. Am J Clin Nutr 2002;76:798‐804.
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stability of the flavan 3 ols epicatechin and catechin and related dimeric Procyanidins derived from cocoa
Journal of Agricultural and Food Chemistry, 2002Co-Authors: Roberta R Holt, Sheryl A Lazarus, John F Hammerstone, Harold H Schmitz, Jodi L Ensunsa, Carl L KeenAbstract:Cocoa flavanols and Procyanidins possess wide-ranging biological activities. The present study investigated the stability of the cocoa monomers, (−)-epicatechin and (+)-catechin, and the dimers, epicatechin-(4β-8)-epicatechin (Dimer B2) and epicatechin-(4β- 6)-epicatechin (Dimer B5), in simulated gastric and intestinal juice and at different pH values. The dimers were less stable than the monomers at both acidic and alkaline pH. Incubation of Dimer B2 and Dimer B5 in simulated gastric juice (pH 1.8) or acidic pH resulted in degradation to epicatechin and isomerization to Dimer B5 and Dimer B2, respectively. When incubated in simulated intestinal juice or at alkaline pH, all four compounds degraded almost completely within several hours. These results suggest that the amount, and type, of flavanols and Procyanidins in the gastrointestinal tract following the consumption of cocoa can be influenced by the stability of these compounds in both acidic and alkaline environments. Keywords: Cocoa; procyanidin; (+)...
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identification of Procyanidins and anthocyanins in blueberries and cranberries vaccinium spp using high performance liquid chromatography mass spectrometry
Journal of Agricultural and Food Chemistry, 2001Co-Authors: Ronald L Prior, Sheryl A Lazarus, Guohua Cao, Helen U Muccitelli, John F HammerstoneAbstract:Blueberries and cranberries were analyzed for Procyanidins using normal-phase HPLC/MS. Monomers, identified as (+)-catechin and (−)-epicatechin, and a series of oligomers were detected in blueberries, and MS data confirmed that the oligomers consisted of (epi)catechin units that were exclusively singly linked (B-type). The procyanidin “fingerprints” were similar for Tifblue and Rubel but higher than that for lowbush blueberries. In whole cranberries, (−)-epicatechin was present, along with a complex series of oligomers. Both A-type (contained only one double linkage per oligomer) and B-type oligomers were present. Two commercial cranberry juices exhibited similar procyanidin profiles, except that one contained increased quantitites. There were processing effects on the procyanidin content of cranberry extract and juices when compared to those of the unprocessed fruits. Monomer, dimers, and A-type trimers were the primary Procyanidins, with only trace levels of the B-type trimers and A-type tetramers and w...
Yasuyuki Ohtake - One of the best experts on this subject based on the ideXlab platform.
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apple Procyanidins induce tumor cell apoptosis through mitochondrial pathway activation of caspase 3
Carcinogenesis, 2007Co-Authors: Tomisato Miura, Toshihiko Shoji, Tomomasa Kanda, Yasuyuki Ohtake, Mitsuru Chiba, Kousuke Kasai, Hiroyuki Nozaka, Toshiya Nakamura, Tatsusuke SatoAbstract:Various epidemiologic and experimental in vivo and in vitro studies have suggested that polyphenols derived from fruits, vegetables and beverages might decrease the risk of developing lifestyle diseases, such as cardiovascular disorders and cancer. Apples are a major dietary source of polyphenols. Here we investigated the antitumor activity of apple polyphenols (APs) and Procyanidins, namely condensed tannins, both in vitro and in vivo studies. APs and Procyanidins inhibited the growth of transplanted B16 mouse melanoma cells and BALB-MC.E12 mouse mammary tumor cells, and increased the survival rate of the host mice-transplanted B16 cells. Among the APs, the apple Procyanidins specifically, rather than other polyphenols such as chlorogenic acid, (-)-epicatechin, phloridzin and procyanidin B2, had a major effect on cell proliferation and induced apoptosis in vitro. The apple Procyanidins increased mitochondrial membrane permeability and cytochrome c release from mitochondria and activated caspase-3 and caspase-9 within the tumor cells. In addition, we separated eight procyanidin fractions according to the degree of polymerization using normal-phase chromatography, and detected strong anti-tumor activity in the procyanidin pentamer and higher degree fractions. Our results indicate that the oral administration of apple Procyanidins inhibits the proliferation of tumor cells by inducing apoptosis through the intrinsic mitochondrial pathway.
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oligomeric Procyanidins in apple polyphenol are main active components for inhibition of pancreatic lipase and triglyceride absorption
Journal of Agricultural and Food Chemistry, 2007Co-Authors: Hiroshi Sugiyama, Toshihiko Shoji, Tomomasa Kanda, Yoko Akazome, Atsuko Yamaguchi, Masaaki Yasue, Yasuyuki OhtakeAbstract:Inhibitory effects of apple polyphenol extract (AP) and procyanidin contained in AP on in vitro pancreatic lipase activity and in vivo triglyceride absorption in mice and humans were examined. AP and procyanidin considerably inhibited in vitro pancreatic lipase activity. However, polyphenols, except for procyanidin, in AP (i.e., catechins, chalcones, and phenol carboxylic acids) showed weak inhibitory activities on pancreatic lipase. Procyanidins separated by normal-phase chromatography according to the degree of polymerization were also examined. Inhibitory effects of Procyanidins increased according to the degree of polymerization from dimer to pentamer. On the other hand, pentamer or greater Procyanidins showed maximal inhibitory effects on pancreatic lipase. These results suggested that with respect to in vitro pancreatic lipase inhibition, the degree of polymerization was an important factor and oligomeric procyanidin mainly contributed. Next, we performed a triglyceride tolerance test in mice and humans. Simultaneous ingestion of AP and triglyceride significantly inhibited an increase of plasma triglyceride levels in both models. These results suggested that the oligomeric Procyanidins contained in AP inhibited triglyceride absorption by inhibiting pancreatic lipase activity in mice and humans.
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oligomeric Procyanidins in apple polyphenol are main active components for inhibition of pancreatic lipase and triglyceride absorption
Journal of Agricultural and Food Chemistry, 2007Co-Authors: Hiroshi Sugiyama, Toshihiko Shoji, Tomomasa Kanda, Yoko Akazome, Atsuko Yamaguchi, Masaaki Yasue, Yasuyuki OhtakeAbstract:Inhibitory effects of apple polyphenol extract (AP) and procyanidin contained in AP on in vitro pancreatic lipase activity and in vivo triglyceride absorption in mice and humans were examined. AP and procyanidin considerably inhibited in vitro pancreatic lipase activity. However, polyphenols, except for procyanidin, in AP (i.e., catechins, chalcones, and phenol carboxylic acids) showed weak inhibitory activities on pancreatic lipase. Procyanidins separated by normal-phase chromatography according to the degree of polymerization were also examined. Inhibitory effects of Procyanidins increased according to the degree of polymerization from dimer to pentamer. On the other hand, pentamer or greater Procyanidins showed maximal inhibitory effects on pancreatic lipase. These results suggested that with respect to in vitro pancreatic lipase inhibition, the degree of polymerization was an important factor and oligomeric procyanidin mainly contributed. Next, we performed a triglyceride tolerance test in mice and hu...
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apple procyanidin oligomers absorption in rats after oral administration analysis of Procyanidins in plasma using the porter method and high performance liquid chromatography tandem mass spectrometry
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Toshihiko Shoji, Saeko Masumoto, Nina Moriichi, Hiroshi Akiyama, Tomomasa Kanda, Yasuyuki Ohtake, Yukihiro GodaAbstract:In this study, we investigated the absorption of apple Procyanidins, namely, apple condensed tannins (ACTs), in rats using the Porter method and high-performance liquid chromatography/tandem mass spectrometry. The apple procyanidin concentrations in the rat plasma reached a maximum 2 h after administration and decreased thereafter. To investigate the limits of the absorption of apple Procyanidins in the polymerization degree, we administered the procyanidin oligomer fraction, which was separated from ACT using normal-phase chromatography according to the degree of polymerization. Procyanidins from each dimer to pentamer group were detected in the plasma by the Porter method. Moreover, by the study using reconstituted Procyanidins, polymeric Procyanidins influenced the absorption of procyanidin oligomers. These results suggest that ACTs are absorbed and directly involved in physiological functions in the rats. Keywords: Absorption; apple Procyanidins; HPLC/MS/MS; procyanidin dimers; procyanidin trimers
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apple procyanidin oligomers absorption in rats after oral administration analysis of Procyanidins in plasma using the porter method and high performance liquid chromatography tandem mass spectrometry
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Toshihiko Shoji, Saeko Masumoto, Nina Moriichi, Hiroshi Akiyama, Tomomasa Kanda, Yasuyuki Ohtake, Yukihiro GodaAbstract:In this study, we investigated the absorption of apple Procyanidins, namely, apple condensed tannins (ACTs), in rats using the Porter method and high-performance liquid chromatography/tandem mass spectrometry. The apple procyanidin concentrations in the rat plasma reached a maximum 2 h after administration and decreased thereafter. To investigate the limits of the absorption of apple Procyanidins in the polymerization degree, we administered the procyanidin oligomer fraction, which was separated from ACT using normal-phase chromatography according to the degree of polymerization. Procyanidins from each dimer to pentamer group were detected in the plasma by the Porter method. Moreover, by the study using reconstituted Procyanidins, polymeric Procyanidins influenced the absorption of procyanidin oligomers. These results suggest that ACTs are absorbed and directly involved in physiological functions in the rats.
