• Title/Summary/Keyword: Stilbenes

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Evolution of 49 Phenolic Compounds in Shortly-aged Red Wines Made from Cabernet Gernischt (Vitis vinifera L. cv.)

  • Li, Zheng;Pan, Qiu-Hong;Jin, Zan-Min;He, Jian-Jun;Liang, Na-Na;Duan, Chang-Qing
    • Food Science and Biotechnology
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    • v.18 no.4
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    • pp.1001-1012
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    • 2009
  • A total of 49 phenolic compounds were identified from the aged red wines made from Cabernet Gernischt (Vitis vinifera L. cv.) grapes, a Chinese characteristic variety, including 13 anthocyanins, 4 pryanocyanins, 4 flavan-3-ol monomers, 6 flavan-3-ol polymers, 7 flavonols, 6 hydroxybenzoic acids, 5 hydroxycinnamic acids, 3 stilbenes, and 1 polymeric pigment. Evolution of these compounds was investigated in wines aged 1 to 13 months. Variance analysis showed that the levels of most phenolics existed significant difference in between wines aged 3 and 9 months. Cluster analysis indicated that 2 groups could be distinguished, one corresponding to wines aged 1 to 3 months and the other to wines aged 4 to 13 months. It was thus suggested that there were 2 key-stages for the development of fine wine quality, at the aged 3 and 9 months, respectively. This work would provide some helpful information for quality control in wine production.

Isolation and Biological Activity of $Resveratrol-3-O-{\beta}-D-Glucoside$ in Transgenic Rehmannia glutinosa L. Transformed by Peanut Resveratrol Synthase Gene (RS3)

  • Lim, Jung-Dae;Yang, Deok-Chun;Yun, Song-Joong;Chung, Ill-Min;Sung, Eun-Soo;Kim, Myong-Jo;Heo, Kweon;Yu, Chang-Yeon
    • Korean Journal of Medicinal Crop Science
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    • v.12 no.5
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    • pp.406-414
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    • 2004
  • Resveratrol, which is both a phytoalexin with antifungal activity and a phytochemical associated with reduced cancer risk and reduced cardiovascular disease, is synthesized in a limited number of plant species including peanut. Resveratrol synthesis is catalyzed by the enzyme stilbene synthase including resveratrol synthase (RS). Resveratrol synthase gene (RS3) obtained from peanut, Arachis hypogaea, Fabaceae has been transferred into chinese foxglove, Rehmannia glutinosa by using Agrobacterium mediated transformation. RS t-DNA introduced to chinese foxglove (R. glutinosa L) by transformation and its reaction product, $resveratrol-3-O-{\beta}-D-glucoside$ was isolated and characterized using HPLC. Also its biological effects was tested in inhibition of the lipid peroxidation of mouse LDL by glycosylated stilbenes derivatives obtained from transgenic plants. $Resveratrol-3-O-{\beta}-D-glucoside$ isolated from transgenic R. glutinosa L. showed antimicrobial activity of the growth inhibition zone against Escherichia coli and Salmonella typhimurium. Therefore, this compound can be contributed to be useful as a phytoalexin for plant health as well as a phytochemical for human health.

Quantitative analysis of anthraquinones in Polygonum multiflorum Thunberg (하수오(何首烏)의 안트라퀴논 함량분석)

  • Lee, Hye-Won;Park, So-Young;Choo, Byung-Kil;Chae, Sung-Wook;Lee, A-Yeong;Kim, Ho-Kyoung
    • Korean Journal of Oriental Medicine
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    • v.13 no.3
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    • pp.157-163
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    • 2007
  • Objective: Polygonum multiflorum Thunberg (Polygonaceae) has been traditionally used as a tonic and the purgative in China and Korea. The genus Polygonum is a source of a wide range of phenolic compound, flavanoids, anthraquinones, stilbenes and tannins. In this study, three anthraquinones were isolated and quantitative determination of anthraquinones from P multiflorum has been developed for quality standardization. Methods : Three anthraquinone derivatives were isolated from a methanol extract of the radix of P. multiflorum by the chromatographic separation. Their structures were identified as emodin, physcion and ${\omega}$-hydroxyemodin on the basis of spectral data (MS, lH-NMR, 13C-NMR) and chemical analysis. HPLC analysis was performed to determine the contents of emodin, physcion, chrysophanol, rhein and ${\omega}$-hydroxyemodin in P. multiflorum from different specimens were collected from twenty Korean markets. Results: According to the results, the contents of emodin, physcion, chrysophanol, rhein and ${\omega}$-hydroxyemodin were 0.145%, 0.434%, 0.016%, 0.026%, 0.030% by HPLC, respectively. Conclusions : In these results, we have determined the contents of emodin, physcion, chrysophanol, rhein and ${\omega}$-hydroxyemodin in P. multiflorum, respectively. We hope that this study will contribute to the standardization and quality control of herbal medicine.

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Anti-Helicobacter pylori Compounds from Polygonum cuspidatum

  • Khalil, Atif Ali Khan;Park, Woo Sung;Kim, Hye Jin;Akter, Kazi Marjahan;Ahn, Mi-Jeong
    • Natural Product Sciences
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    • v.22 no.3
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    • pp.220-224
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    • 2016
  • Anti-Helicobacter pylori activity guided fractionation led to the isolation of five anthraquinones, two stilbenes and one naphthoquinone from the EtOAc fraction of Polygonum cuspidatum, using silica gel column chromatography, Sephadex-LH20, MPLC and recrystallization. The chemical structures were identified to be physcion (1), emodin (2), anthraglycoside B (3), trans-resveratrol (4), anthraglycoside A (5), polydatin (6), 2-methoxy-6-acetyl-7-methyljuglone (7) and citreorosein (8) by UV, $^1H$-NMR, $^{13}C$-NMR and mass spectrometry. Anti-Helicobacter pylori activity including MIC values of each compound was evaluated. All of the isolates exhibited anti-H. pylori activity of which MIC values were lower than that of a positive control, quercetin. Compounds 2 and 7 showed potent growth inhibitory activity. Especially, a naphthoquinone, compound 7 displayed most potent antibacterial activity with $MIC_{50}$ value of $0.30{\mu}M$ and $MIC_{90}$ value of $0.39{\mu}M$. Although anti-H. pylori activity of this plant was previously reported, this is the first report on that of compounds isolated from this species. From these findings, P. cuspidatum roots or its isolates may be useful for H. pylori infection and further study is needed to elucidate mechanism of action.

Effect of Resveratrol on Oral Cancer Cell Invasion Induced by Lysophosphatidic Acid

  • Kim, Jin Young;Cho, Kyung Hwa;Lee, Hoi Young
    • Journal of dental hygiene science
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    • v.18 no.3
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    • pp.188-193
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    • 2018
  • The aim of the current study was to demonstrate the potential therapeutic efficacy of resveratrol in oral cancer patients. Lysophosphatidic acid (LPA) intensifies cancer cell invasion and metastasis, whereas resveratrol, a natural polyphenolic compound, possesses antitumor activity, suppressing cell proliferation and progression in various cancer cell lines (ovarian, gastric, oral, pancreatic, colon, and prostate cancer cells). In addition, resveratrol has been identified as an inhibitor of LPA-induced proteolytic enzyme expression and ovarian cancer invasion. Furthermore, resveratrol was shown to inhibit oral cancer cell invasion by downregulating hypoxia-inducible factor $1{\alpha}$ and vascular endothelial growth factor expression. Recently, we demonstrated that LPA is important for the expression of transcription factors TWIST and SLUG during epithelial-mesenchymal transition (EMT) in oral squamous carcinoma cells. In this study, we treated serum-starved cultures of oral squamous carcinoma cell line YD-10B with resveratrol for 24 hours prior to stimulation with LPA. To identify an optimal resveratrol concentration that does not induce apoptosis in oral squamous carcinoma cells, we determined the toxicity of resveratrol in YD-10B cells by assessing their viability using the MTT assay. Another assay was performed using Matrigel-coated cell culture inserts to detect oral cancer cell invasion activity. Immunoblotting was applied for analyzing protein expression of SLUG, TWIST1, E-cadherin, and GAPDH. We demonstrated that resveratrol efficiently inhibited LPA-induced oral cancer cell EMT and invasion by downregulating SLUG and TWIST1 expression. Therefore, resveratrol may potentially reduce oral squamous carcinoma cell invasion and metastasis in oral cancer patients, improving their survival outcomes. In summary, we identified new targets for the development of therapies against oral cancer progression and characterized the therapeutic potential of resveratrol for the treatment of oral cancer patients.

The Effects of Polydatin Isolated from Polygonum cuspidatum on Melanogenesis and Wrinkle Formation (호장으로부터 분리한 Polydatin의 미백 및 주름억제 효능에 대한 연구)

  • Jin, Mu-Hyun;Jeong, Eui-Taek;Kim, Mi-Sun;Song, Hye-Jin;Kwak, Taek-jong;Park, Sun-Gyoo;Lee, Sang-Min
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.37 no.4
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    • pp.327-335
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    • 2011
  • 5,4'-dihydroxystilbene-3-O-${\beta}$-D-glucopyranoside (Polydatin) is one of the stilbenes found in Polygonum cuspidatum (P. cuspidatum), however, the effects of polydatin on skin biology remain to be elucidated. In this study, we obtained polydatin from P. cuspidatum and investigated the effects of polydatin in skin-derived melanocytes and fibroblasts. In melanocytes, polydatin inhibited not only the tyrosinase activity and melanin production but the expression of melanogenic factors, tyrosinase and microphthalmia-associated transcription factor (MITF). In addition, the level of type I procollagen in fibroblasts was analyzed, and polydatin significantly induced the production of type I procollagen in a dose-dependent manner. Finally we conformed that topical treatment of polydatin improved wrinkle and induced whitening of human skin in vivo. These data provide evidence that polydatin can be a potent candidate for the improvement of both skin wrinkle and whitening from the point of industry view.

The Role of Resveratrol in Lipid Metabolism: A Systematic Review of Current Basic and Translational Evidence (레스베라트롤의 지질 대사 효과에 대한 체계적 문헌 고찰)

  • Choi, Seung Kug;Moon, Hyun-Seuk
    • Journal of Food Hygiene and Safety
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    • v.31 no.2
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    • pp.67-73
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    • 2016
  • Resveratrol is a non-flavonoid polyphenol which belongs to the stilbenes group and is naturally generated in several plants in response to damage or fungal invasion. It has been shown in published studies that resveratrol has an anti-adipogenic effect. A good consensus regarding the involvement of a down-regulation of $C/EBP{\alpha}$ and $PPAR{\gamma}$ in this effect has been reached. In addition, different metabolic pathways involved in triacylglycerol metabolism in white adipose tissue have been shown to be regulated by resveratrol. Concerning lipolysis, though this compound in itself seems to be unable to cause lipolysis, it increases lipid mobilization stimulated by ${\beta}-adrenergic$ agents. The increase in brown adipose tissue thermogenesis, and accordingly the associated energy dissipation, can attribute to accounting for the body-fat reducing effect of resveratrol. Besides its effects on adipose tissue, resveratrol can also acts on other organs and tissues. Therefore, it increases mitochondrial biogenesis and accordingly fatty acid oxidation in skeletal muscle and liver. This effect can also attribute to the body-fat reducing effect of this molecule. The present review purposes to collect the evidence concerning the potential mechanisms of action which underlie the anti-obesity effects of resveratrol, acquired either in cultured cells lines and animal models.

Total Polyphenol Content and Antioxidative Activity of Wild Grape (Vitis coignetiae) Extracts Depending on Ethanol Concentrations (에탄올 농도에 따른 머루(Wild Grape, Vitis coignetiae) 추출물의 폴리페놀 함량 및 항산화 활성)

  • Jeong, Hyun-Jin;Park, Seon-Bin;Kim, Sun-A;Kim, Hyun-Ku
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.36 no.12
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    • pp.1491-1496
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    • 2007
  • As an oriental medicinal plant, wild grape (WG, Vitis coignetiae) has been known to contain abundant nutrients compared to grape (Vitis vinifera L.) and as a source of stilbenes, a kind of polyphenol. This study was performed to investigate the antioxidative activity of WG extracts by measuring electron donating ability (EDA), nitrite scavenging ability (NSA), super oxide dismutase (SOD)-like activity and total polyphenol content (TPC). The extracts were obtained using microwave-assisted extraction (microwave power: 90 W, extraction time: 5 min, extractant: water, 50 and 100% ethanol). EDAs, SOD-like activities and TPCs were the highest at 50% ethanol extracts while conversely lowest at 100% ethanol extracts. EDAs of 50% and 100% ethanol extracts at 1.6 g/dL concentration, $97.70{\pm}0.55\;and\;98.05{\pm}0.36%$, were higher than those of 0.1 and 1% L-ascorbic acids, $101.44{\pm}0.98%\;and\;99.43{\pm}0.78%$, respectively. At the concentration of 1.6 g/dL, 50% ethanol extract showed lower NSA (pH 1.2) than water extract unlike EDA, TPC and SOD-like activity. Regarding TPCs of WG extracts, the activities were the highest at 50% ethanol extracts (1.6 g/dL: $38.76{\pm}0.23$ mM gallic acid equiv.) followed by water and 100% ethanol extracts. The results suggest the usefulness of developing functional foods using antioxidative active compounds of WG with high polyphenol contents.

Antioxidant and α-glucosidase inhibitory effects of ethanolic extract of Ainsliaea acerifolia and organic solvent-soluble fractions (단풍취 추출물 및 분획물의 항산화 및 α-glucosidase 저해 활성 평가)

  • Lee, Eun-Woo;Kim, Taewan;Kim, Hyun-Seok;Park, Youn-Moon;Kim, Seong-Ho;Im, Moo-Hyeog;Kwak, Jae Hoon;Kim, Tae Hoon
    • Food Science and Preservation
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    • v.22 no.2
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    • pp.275-280
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    • 2015
  • Among the naturally occurring antioxidants, polyphenols are widely distributed in various fruits, vegetables, wines, juices, and plant-based dietary sources and divided into several subclasses that included phenolic acid, flavonoids, stilbenes, and lignans. As part of our continuing search for bioactive food ingredients, the antioxidant and ${\alpha}$-glucosidase inhibitory activities of the aqueous ethanolic extract from the aerial parts of Ainsliaea acerifolia were investigated in vitro. The antioxidant properties were evaluated via radical scavenging assays using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) ($ABTS^+$) radicals. In addition, the anti-diabetic effect of A. acerifolia extracts was tested via ${\alpha}$-glucosidase inhibitory assay. Furthermore, the total phenolic contents were determined using a spectrophotometric method. All the tested samples showed dose-dependent radical scavenging and ${\alpha}$-glucosidase inhibitory activities. In particularly, the ${\alpha}$-glucosidase inhibitory and radical scavenging properties of the ethyl acetate (EtOAc)-soluble portion from the aerial parts of the A. acerifolia were higher than those of the other solvent-soluble portions. These results suggest that A. acerifolia could be considered a new potential source of natural antioxidants and antidiabetic ingredients. More systematic investigation of the aerial parts of A. acerifolia will be performed for the further development of anti-oxidative and antidiabetic drugs.