Epicatechin Is the Primary Bioavailable Form of the Procyanidin Dimers B2 and B5 after Transfer across the Small Intestine

Spencer, Jeremy P.E.; Schroeter, Hagen; Shenoy, Bhami; Srai, Surjit Kaila; Debnam, ES; Rice‐Evans, Catherine

doi:10.1006/bbrc.2001.5211

Cited by 118 publications

(72 citation statements)

References 28 publications

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“…Similar observations have been made previously but have been explained by suggesting that the major bioavailable form of procyanidin dimers (B2 and B5) was (Ϫ)-epicatechin formed by depolymerization based on studies using an in vitro small intestinal model (Spencer et al, 2001). Subsequent studies in humans showed that this depolymerization did not occur in vivo (Rios et al, 2002).…”

Section: In Vitrosupporting

confidence: 80%

In Vivo Bioavailability, Absorption, Excretion, and Pharmacokinetics of [¹⁴C]Procyanidin B2 in Male Rats

et al. 2009

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Section: In Vitrosupporting

confidence: 80%

In Vivo Bioavailability, Absorption, Excretion, and Pharmacokinetics of [¹⁴C]Procyanidin B2 in Male Rats

et al. 2009

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“…51) While only small amounts of procyanidin dimer are absorbed directly by humans, 52,53) it can be digested into the monomer form before being absorbed. 54) As compared with the other dietary procyanidins, such as those from grape, apple, and cocoa, our results show that the procyanidins present in Chinese hawthorn fruits have lower mDP values and are composed mainly of epicatechin. Furthermore, our results indicate that ethyl acetate extraction gives HP with a higher level of polyphenols, with particularly high concentrations of epicatechin and procyanidin B2.…”

Section: Protease Inhibitory Activitiesmentioning

confidence: 57%

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Cui

Nakamura

Tian

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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Hawthorn polyphenol (HP) was prepared by ethyl acetate treatment of the ethanol extract (HE) of Chinese hawthorn fruit. The concentrations of 15 polyphenols in the HP, HE, extraction residue (HJ), and a hawthorn leaf extract (HF) were determined by HPLC. For HP, the total content of the 15 polyphenols was 21.4%, comprised of 19.7% of procyanidins, 1.21% of chlorogenic acid, and 0.48% of flavonoids, compared to 2.55% for the HE. The yields of procyanidin monomer, dimer, trimer, tetramer, and pentamer were 50.5%, 30.3%, 23.0%, 14.6%, and 12.5% respectively, and the mean degree of polymerization was reduced to 1.39 (HP) from 1.65 (HE). Seven different physiological actions of the four extracts were investigated. The HP showed strong O 2 À and OH scavenging capacities (IC 50 values of 6.3 g/ml and 1.1 g/ml respectively), as well as selective prolyl endopeptidase inhibition (IC 50 of 60 g/ml). The active constituents appeared to be procyanidins.Key words: Crataegus pinnatifida; HPLC; procyanidin; antioxidant; free radicalsIn Europe, standardized extracts of the leaves and flowers of Crataegus oxyacantha and Crataegus monogyna are used in the therapy for moderate (NYHA II) congestive heart failure. 1,2) These extracts exert several pharmacological and clinical effects, such as antiischemia/reperfusion-injury, anti-arrhythmic, hypolipidemic, and hypotensive effects. 1,2) Flavonoids and procyanidins are considered to be the two main active constituents. 2) Species of Chinese hawthorn, particularly Crataegus pinnatifida and Crataegus pinnatifida Bge. var. major NE Br., have also been used as herbal medicines. 2,3) Studies indicate that Chinese hawthorn extracts have beneficial effects, such as antioxidant, 4,5) anti-inflammatory, 6) and hypolipidemic effects, 7) as well as protective effects on the brain and vascular endothelium 8,9) and endothelium-dependent relaxation. 10) Recently, we analyzed 37 major cultivars of Chinese hawthorn using high performance liquid chromatography (HPLC), and found that procyanidins, which were present in high concentrations, were the main phenolic active constituents in these fruits. 11) In general, the hawthorn found in China is an edible fruit that is popular for its special acidic taste. It is bigger than its European counterpart. Since the content of organic acid in Chinese hawthorn fruits can be up to 5% (fresh weight), they are used to produce various foods, such as jams, jellies, juices, tinned foods, wines, and various sweet foods. However, the high sugar content of these fruits counteracts the benefits of polyphenols for consumers of advanced age or for those who suffer from hypertension, cardiovascular disease, or diabetes. Hence, it is desirable to separate the polyphenol and sugar components. Previously, hawthorn extract (HE) for medical applications were ethanol-extracted from the dried fruit of the Chinese hawthorn. 12) These crude extracts contain many undesirable substances, such as carbohydrates, organic acids, and moisture, which not only reduce the concentration of acti...

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“…In contrast, studies indicate that procyanidins have a very low bioavailability, and neither glucuronides nor sulfates have been detected so far (Holt et al, 2002;Sano et al, 2003). However, small amounts of methylated procyanidin metabolites were observed in rats (Spencer et al, 2001b;Baba et al, 2002;Shoji et al, 2006).…”

Section: Introductionmentioning

confidence: 88%

Methylation of Catechins and Procyanidins by Rat and Human Catechol-O-Methyltransferase: Metabolite Profiling and Molecular Modeling Studies

Weinert¹,

Wiese²,

Rawel³

et al. 2011

Drug Metab Dispos

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ABSTRACT:Catechins and procyanidins are major polyphenols in plant-derived foods. Despite intensive studies in recent years, neither their biochemical nor their toxicological properties have been clarified sufficiently. This study aimed to compare the methylation of catechins and procyanidins by the enzyme catechol-O-methyltransferase (COMT) in vitro. We conducted incubations with rat liver cytosol and human placental cytosol including S-adenosyl-L-methionine. The set of substrates comprised the catechins (؊)-epicatechin (EC) and (؉)-catechin (CAT), the procyanidin dimers B1, B2, B3, B4, B5, and B7 as well as procyanidin trimer C1. After extraction, metabolites were analyzed by means of liquid chromatography-electrospray ionizationmass spectrometry and liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. EC and CAT were converted to two monomethylated metabolites each by human and rat COMT, with the 3-O-methyl derivatives being consistently the main metabolites. Furthermore, the flavanyl units of procyanidins were methylated consecutively, leading to monomethylated and dimethylated dimeric metabolites as well as monomethylated, dimethylated, and trimethylated C1 metabolites. The methylation status of each flavanyl unit was determined by means of mass spectrometric quinone-methide fragmentation patterns. In addition, molecular modeling studies were performed with the aim to predict the preferred site of methylation and to verify the experimental data. In conclusion, our results indicate that the degree and position of methylation depend clearly on the three-dimensional structure of the entire substrate molecule.

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Epicatechin Is the Primary Bioavailable Form of the Procyanidin Dimers B2 and B5 after Transfer across the Small Intestine

Cited by 118 publications

References 28 publications

In Vivo Bioavailability, Absorption, Excretion, and Pharmacokinetics of [¹⁴C]Procyanidin B2 in Male Rats

In Vivo Bioavailability, Absorption, Excretion, and Pharmacokinetics of [¹⁴C]Procyanidin B2 in Male Rats

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Methylation of Catechins and Procyanidins by Rat and Human Catechol-O-Methyltransferase: Metabolite Profiling and Molecular Modeling Studies

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Epicatechin Is the Primary Bioavailable Form of the Procyanidin Dimers B2 and B5 after Transfer across the Small Intestine

Cited by 118 publications

References 28 publications

In Vivo Bioavailability, Absorption, Excretion, and Pharmacokinetics of [14C]Procyanidin B2 in Male Rats

In Vivo Bioavailability, Absorption, Excretion, and Pharmacokinetics of [14C]Procyanidin B2 in Male Rats

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Methylation of Catechins and Procyanidins by Rat and Human Catechol-O-Methyltransferase: Metabolite Profiling and Molecular Modeling Studies

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In Vivo Bioavailability, Absorption, Excretion, and Pharmacokinetics of [¹⁴C]Procyanidin B2 in Male Rats

In Vivo Bioavailability, Absorption, Excretion, and Pharmacokinetics of [¹⁴C]Procyanidin B2 in Male Rats