• Toxicological Research
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• 제33권4호
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• pp.273-282
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• 2017

Chemoprevention entails the use of synthetic agents or naturally occurring dietary phytochemicals to prevent cancer development and progression. One promising chemopreventive agent, procyanidin, is a naturally occurring polyphenol that exhibits beneficial health effects including anti-inflammatory, antiproliferative, and antitumor activities. Currently, many preclinical reports suggest procyanidin as a promising lead compound for cancer prevention and treatment. As a potential anticancer agent, procyanidin has been shown to inhibit the proliferation of various cancer cells in "in vitro and in vivo". Procyanidin has numerous targets, many of which are components of intracellular signaling pathways, including proinflammatory mediators, regulators of cell survival and apoptosis, and angiogenic and metastatic mediators, and modulates a set of upstream kinases, transcription factors, and their regulators. Although remarkable progress characterizing the molecular mechanisms and targets underlying the anticancer properties of procyanidin has been made in the past decade, the chemopreventive targets or biomarkers of procyanidin action have not been completely elucidated. This review focuses on the apoptosis and tumor inhibitory effects of procyanidin with respect to its bioavailability.

• Journal of Veterinary Science
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• 제19권6호
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• pp.798-807
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• 2018

Several studies have reported the effect of absorption of procyanidins and their contribution to the small intestine. However, differences between dietary interventions of procyanidins and interventions via antibiotic feeding in pigs are rarely reported. Following 16S rRNA gene Illumina MiSeq sequencing, we observed that both procyanidin administration for 2 months (procyanidin-1 group) and continuous antibiotic feeding for 1 month followed by procyanidin for 1 month (procyanidin-2 group) increased the number of operational taxonomic units, as well as the Chao 1 and ACE indices, compared to those in pigs undergoing antibiotic administration for 2 months (antibiotic group). The genera Fibrobacter and Spirochaete were more abundant in the antibiotic group than in the procyanidin-1 and procyanidin-2 groups. Principal component analysis revealed clear separations among the three groups. Additionally, using the online Molecular Ecological Network Analyses pipeline, three co-occurrence networks were constructed; Lactobacillus was in a co-occurrence relationship with Trichococcus and Desulfovibrio and a co-exclusion relationship with Bacillus and Spharerochaeta. Furthermore, metabolic function analysis by phylogenetic investigation of communities by reconstruction of unobserved states demonstrated modulation of pathways involved in the metabolism of carbohydrates, amino acids, energy, and nucleotides. These data suggest that procyanidin influences the gut microbiota and the intestinal metabolic function to produce beneficial effects on metabolic homeostasis.

• Asian-Australasian Journal of Animal Sciences
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• 제27권1호
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• pp.131-139
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• 2014

This study was performed to determine the effect of dietary supplementation of procyanidin on growth performance, blood characteristics, and immune function in growing pigs. In experiment 1 (Exp. 1), thirty-two crossbred pigs with an initial BW of $19.2{\pm}0.3$ kg were allocated into 4 treatments for an 8-wk experiment: i) CON (basal diet), ii) MOS 0.1 (basal diet+0.1% mannanoligosaccharide), iii) Pro-1 (basal diet+0.01% procyanidin), and iv) Pro-2 (basal diet+0.02% procyanidin). Pigs fed Pro-1 and Pro-2 diets had greater (p<0.05) gain:feed ratio compared with those fed CON or MOS 0.1 diets. Serum creatinine concentration was less (p<0.05) in Pro-2 treatment than those in CON, MOS 0.1 and Pro-1 treatments. In Exp. 2, twelve pigs (BW $13.4{\pm}1.3$ kg) received basal diet with i) 0 (CON), ii) 0.02% (Pro-0.02%), and iii) 0.04% procyanidin (Pro-0.04%) for 4 wk. Concentration of platelets was lower (p<0.05) in the Pro-0.04% group compared to CON at 24 h after lipopolysaccharide (LPS) challenge. In addition, secretion of cytokines from cultured peripheral blood mononuclear cells (PBMC) in the presence or absence of procyanidin was examined. The levels of interleukin (IL)-$1{\beta}$, IL-6 and tumor necrosis factor (TNF)-${\alpha}$ were lower (p<0.05) in Pro (LPS-stimulated PBMCs+procyanidin) than those in CON (LPS-stimulated PBMCs+PBS) at 4 h after LPS challenge. These data suggest that dietary addition of procyanidin improves feed efficiency and anti-inflammatory cytokines of pigs.

• 한국축산식품학회지
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• 제35권4호
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• pp.564-571
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• 2015

Grape seeds and pericarp are rich in procyanidins, a class of natural antioxidants and antimicrobials that can provide phytonutrients for healthy eating and extend food shelf life. The objective of this study was to assess the effect of procyanidins as preservatives in pork meat patties for 14 d. Pork patties were treated with 0, 0.1, or 0.3% procyanidin, and meat color, pH, volatile basic nitrogen (VBN), 2-thiobarbituric acid reactive substance (TBARS) values, and microbial populations were determined during storage at 4℃ for 14 d. The color of pork patties treated with procyanidin showed lower lightness and higher redness values than untreated controls, and procyanidin treatment reduced pH values significantly (p<0.05). VBN values decreased significantly (p<0.05) with the 0.3% procyanidin treatment and increased significantly (p<0.05) during storage. TBARS values were markedly lower in procyanidin-treated meat than in the untreated control. In addition, procyanidin suppressed total bacterial colony and Escherichia coli counts significantly (p<0.05) relative to the control samples. Our findings suggest that procyanidin could be used as a food preservative in pork patties due to its natural antioxidation and antimicrobial activities, and that it may contribute to an improved healthy diet.

• 한국식품과학회지
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• 제35권6호
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• pp.1199-1203
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• 2003

한국산 녹차를 70% 에탄올로 추출한 후 Sephadex LH-20과 HPLC를 사용하여 polyphenol을 분리동정하였고 분리된 각 성분들의 angiotensin converting enzyme(ACE) 및 xanthine oxidase, tyrosinase의 저해효과를 확인하였다. 녹차로부터 HPLC로 polyphenol을 분리한 결과 epiafzelechin-$(4{\beta}{\rightarrow}8)$-epiafzelechin, procyanidin B-3-3-O-rhamnose, afzelechin-$(4{\alpha}{\rightarrow}8)$-catechin, prodelphinidin B-5-3,3'-di-O-digallate, (+)-taxifolin-3-O-D-xyloside 등 11종류를 분리하였다. ACE의 저해효과는 prodelphinidin-C-2-3,3'-di-O-gallate $100{\mu}M$에서 68.8%, procyanidin B-2-3,3'-digallate가 54.6%의 저해를 나타내었고, Xanthine oxidase는 prodelphinidin C-2-3,3'-di-O-gallate가 54.5%, procyanidin B-2-3,3'-digallate가 38.2%로 높은 저해효과를 보였다. Tyrosinase의 저해효과는 $100{\mu}M$ 농도에서 prodelphinidin C-2-3,3'-di-O-gallate가 42.1%, procyanidin B-2-3,3'-digallate와 procyanidin B-7이 각각 30.7%, 20.5%의 저해를 나타내었다. 따라서 녹차 추출물로부터 분리한 polyphenol이 혈압예방, 통풍 및 미백효과의 기능성 식품 신소재로서 이용이 가능하다는 것을 확인하였다.

• Applied Biological Chemistry
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• 제41권1호
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• pp.110-117
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• 1998

Ghana산 cacao bean으로부터 acetone으로 추출하고 Sephadex LH-20, MCI-gel CHP-20, Bondapak $C_{18}$ 및 Fuji gel ODS $G_3$, chromatography 등을 이용하여 7종의 polyphenol 화합물(compound 1 - compound 7)을 분리 정제하였고, 이들 화합물의 화학구조를 $^1H-NMR$, $^{13}C-NMR$, IR 및 MS를 사용하여 검색하였고 아울러 angiotensin converting enzyme(ACE) 저해효과를 조사 검토하였다. 분리정제한 7종의 polyphenol 화합물의 구조를 분석한 결과, compound 1: [(+)-catechin], compound 2: [(-)-epicatechin], compound 3: [procyanidin B-1, (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(+)-catechin], compound 4 : [procyanidin B-2, (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin], compound 5: [procyanidin B-7, (-)-epicatechin-$(4{\beta}{\rightarrow}6)$-(+)-catechin], compound 6 : (procyanidin B-2,3,3'-O-digallate) 및 compound 7: [cinnamtannin A-2, (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin]임을 동정하였다. ACE의 저해효과는 procyanidin B-2,3,3'-O-digallate (compound 6)가 $100\;{\um}M$에서 94.6%로 매우 우수하였으며, (+)-catechin (compound 1), (-)-epicate -chin (compound 2), procyanidin B류 (compound 3, 4, 5) 및 cinnamtannin A-2 (compound 7)도 각각 67.9%, 61.9%, 88.6%, 82.5%, 72.2% 및 82.3%의 비교적 우수한 저해효과가 있었다. 아울러 결합방식에서는 $4{\beta}{\rightarrow}6$보다 $4{\beta}{\rightarrow}8$의 결합방식이, 그리고 procyanidin 류에서는 gallate를 갖는 물질이 이를 함유하지 많은 물질보다 더욱 높은 ACE의 저해효과를 나타내었으며, 또한 hydroxyl 기가 많을수록 효소 저해효과도 증가하는 것으로 나타났다. 이와 같은 결과는 chocolate의 주원료인 cacao bean의 polyphenol 성분 또한 녹차 등에서 볼 수 있는 생리활성효과에 손색없는 것으로 판단되고, 이러한 기능성에 기초하여 chocolate, 음료 등의 식품이나 의약품의 기능성 소재로서의 산업적 응용 가능성이 높은 것으로 사료된다.

• Applied Biological Chemistry
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• 제37권6호
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• pp.498-502
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• 1994

Cacao bean husk로부터 2종류의 2당체 flavan-3-ol을 분리하였고 $anisaldehyde-H_2SO_4$ 용액, $FeCl_3$ 및 TLC상에서 축합형 탄닌으로 확인되었다. 이들 2종류의 flavan-3-ol 화합물은 procyanidin B-1[epicatechin-$(4{\beta}{\rightarrow}8)$-catechin], procyanidin B-3[catechin-$(4{\alpha}{\rightarrow}8)$-catechin]로 기기분석에 의해 분자구조가 결정되었다. Procyanidin B-1은 0.3 mM에서 50% glucosyltransferase 저해효과가 관찰되었고 비경쟁적 저해작용기작을 보였으며 epicatechin을 함유한 화합물이 저해 효과가 높은 것으로 확인되었다.

• 한국식품과학회지
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• 제24권6호
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• pp.558-562
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• 1992

Xanthine oxidase는 퓨린 대사에 관여하여 xanthine 혹은 hypoxanthine을 산화하여 요산을 생성하게 하는 효소이다. 이상 퓨린 대사로 인해 형성된 요산은 관절에 축적되어 통풍을 동반하는 통증을 유발한다. 본 연구는 천연물로부터 통풍치료제의 개발을 목적으로 우롱차로 부터 6종의 flavan-3-ol 화합물을 분리하였고 기기분석에 의해 화학구조를 밝혔다. 각 화합물은 (-)-epicatechin, (-)-epicatechin-3-O-gallate, procyanidan B-1, B-3, procyanidin B-3-3'-O-rhamnose procyanidin B-1-3-O-gallate 였다. Xanthine oxidase 저해 영향을 관찰한 결과 gallte가 결함된 flavan-3-ol 화합물이 저해활성이 강하였고 procyanidin B-1-3-O-gallate는 $50\;{\mu}M$에 완전한 저해효과를 나타내었고 xanthine oxidase에 경쟁적으로 저해한다는 것이 밝혀졌다.

• Natural Product Sciences
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• 제9권2호
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• pp.49-51
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• 2003

The underground part of Rosa rugosa Thunb. has been used in Korean folk medicine for treating diabetes. The $^{1}H-NMR$ signal of procyanidin B3 isolated from Rosa rugosa was fully assigned by utilizing $^{1}H-^{1}H$ COSY. Procyandin B3 showed a moderate inhibitory activity against HIV-1 protease.

• 한국식생활문화학회지
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• 제18권5호
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• pp.443-456
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• 2003

The lyophilization of the solution extracted from 60 percent of acetone applied to persimmon leaves, the compounding process in accordance with the solution's concentration, and the gel filteration through Sephadex G-50 of biologically activated substances obstructing enzyme activity, such as tyrosinase, xanthine oxidase, and angiotesin converting enzyme (ACE) led to the assumption that polyphenol was the compound serving as biologically activated substances obstructing enzyme activity. Xanthine oxidase involved in pruine metabolism oxidizes hypoxanthine to xanthine and xanthine to uric acid. In the continuous study for natural compound, nine flavan-3-ols have been isolated from the persimmon leaves. The structures of (+)-catechin, (+)-gallocatechin, procyanidin B-1, pyrocyanidin C-1, prodelphinidin B-3, gallocatechin-$(4{\alpha}{\rightarrow}8)$-catechin, procyanidin B-7-3-O-gallate, procyanidin C-1-3'-3'-3'-O-trigallate and (-)-epigallocatechin-$(4{\alpha}{\rightarrow}8)$-epigallocatechin-$(4{\alpha}{\rightarrow}8)$-catechin were established by NMR and their inhibitory effect on xanthine oxidase activity was investigated. Procyanidin B-7-3-O-gallate, (-)-epigallocatechin-$(4{\alpha}{\rightarrow}8)$-epigallocatechin-$(4{\alpha}{\rightarrow}8)$-catechin and procyanidin C-1-3'-3'-3'-O-trigallate showed 94%, 90.69%, 80.90% inhibition at $100\;({\mu})M$ and inhibited on the angiotensin converting enzyme respectively. Procyanidin B-7-3-O-gallate and procyanidin C-1-3'-3'-3'-O-trigallate showed 66%, 63% inhibition at $100\;({\mu})M$ and inhibited on the xanthine oxidase competitively. Procyanidin C-1-3'-3'-3'-O-trigallate showed 70% inhibition at $100\;({\mu})M$ and inhibited on the tyrosinase competitively.