Procyanidin B1 Is Detected in Human Serum after Intake of Proanthocyanidin-rich Grape Seed Extract

Sano, Atsushi; Yamakoshi, Jun; Tokutake, Shoichi; Tobe, Koichiro; Kubota, Yoshiro; Kikuchi, Mamoru

doi:10.1271/bbb.67.1140

Cited by 205 publications

(143 citation statements)

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“…23) Generally, polyphenol absorption, distribution, metabolism, and excretion are governed by chemical structures, and the biological activities of polyphenols differ according to their components and absorption. [24][25][26][27][28] For this reason, dimeric-, trimeric-, and tetrameric polyphenols have recently been given much attention since they have high biological activity and good absorption.…”

Section: Discussionmentioning

confidence: 99%

Protective Effect of Grape Seed Polyphenols against High Glucose-Induced Oxidative Stress

Fujii¹,

Yokozawa²,

Kim³

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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We aimed to clarify whether grape seed polyphenols (GSPs) are candidates therapeutic agents against diabetes mellitus, and to determine what degree of GSP oligomerization has the most potent efficacy. We studied the protective effects of various molecular weight GSPs (monomer, oligomer, polymer, and oligonol) on high glucose-induced cytotoxicity. In the present study, a high concentration of glucose (30 mM) induced cytotoxicity and oxidative stress (reactive oxygen species and nitric oxide) in cultured LLC-PK 1 cells, but treatment with GSPs, especially oligomer GSPs, had potent protective effects against high glucose-induced oxidative stress. In addition, high glucose induced nuclear translocation of nuclear factor-kappa B, and increased expression of cyclooxygenase-2, inducible nitric oxide synthase, and bax, but GSP treatment inhibited them. These results indicate that GSPs have protective effects against high glucose-induced cytotoxicity, and among them, oligomer GSPs have more potent effects than other GSPs (monomer, polymer, and oligonol) on high glucose-induced renal cell damage.

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Section: Discussionmentioning

confidence: 99%

Protective Effect of Grape Seed Polyphenols against High Glucose-Induced Oxidative Stress

Fujii¹,

Yokozawa²,

Kim³

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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“…50) Monomers are easily absorbed; in this respect, epicatechin is more efficient than catechin. 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.…”

Section: Protease Inhibitory Activitiesmentioning

confidence: 99%

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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“…after administration in both animals (Baba et al, 2002;Shoji et al, 2006) and humans (Holt et al, 2002;Sano et al, 2003). However, the levels of intact procyanidin B2 detected in human plasma (ϳ10 -40 nM) after high doses of proanthocyanidins are lower, sometimes by several orders of magnitude, than the concentrations observed to be effective in various in vitro tests.…”

mentioning

confidence: 98%

“…Later studies in animals, using liquid chromatography/electrospray ionization/mass spectrometry analyses, reported the presence, after enzymatic hydrolysis, of unconjugated procyanidin dimers, including B1, B2, B3, B4, and B5, in various tissues including plasma and urine after feeding large doses of proanthocyanidin extracts or proanthocyanidin-rich seeds (Baba et al, 2002;Tsang et al, 2005;Shoji et al, 2006). Likewise, human studies have detected unconjugated procyanidin B1, B2, and B5 in plasma and serum within 30 min of consumption of the test material (Holt et al, 2002;Sano et al, 2003). Unconjugated procyanidin B2 concentration in the systemic circulation reaches a peak at approximately 2 h This work was funded by the European Union 6th framework project FLAVO.…”

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confidence: 99%

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

et al. 2009

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Procyanidin B1 Is Detected in Human Serum after Intake of Proanthocyanidin-rich Grape Seed Extract

Cited by 205 publications

References 15 publications

Protective Effect of Grape Seed Polyphenols against High Glucose-Induced Oxidative Stress

Protective Effect of Grape Seed Polyphenols against High Glucose-Induced Oxidative Stress

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

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

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Procyanidin B1 Is Detected in Human Serum after Intake of Proanthocyanidin-rich Grape Seed Extract

Cited by 205 publications

References 15 publications

Protective Effect of Grape Seed Polyphenols against High Glucose-Induced Oxidative Stress

Protective Effect of Grape Seed Polyphenols against High Glucose-Induced Oxidative Stress

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

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

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