• Title/Summary/Keyword: Flavan

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Chemical Structure and Isolation of Novel Glucosyltransferase Inhibitor from Artocarpus heterophyllus folium (Jack Fruit 잎으로부터 새로운 Glucosyltransferase 저해물질 분리 및 화학구조)

  • An, Bong-Jeun
    • Korean Journal of Food Science and Technology
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    • v.29 no.6
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    • pp.1304-1308
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    • 1997
  • In the course of studies for anti-plaque agents, novel procyanidin structure isolated from Artocarpus heterophyllus folium was established by thiolysis and spectroscopic analysis. The chemical structure was identified for $(-)-epiafzelecin-(4{\beta}{\rightarrow}8)-afzelecin-(4{\alpha}-8)-catechin$ containing the trimeric flavan-3-ols and molecular weight was 833[M-H] by FAB-MS negative ion method. The inhibitory effect on the glucosyltransferase activity was investigated, novel compound showed complete inhibition at 1.0 mM and inhibited on the glucosyltransferase noncompetitively.

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Extractives from the leaves of Thuja orientalis Linnaeus (측백나무(Thuja orientalis Linnaeus) 잎의 추출성분)

  • 이상극;김진규;함연호;배영수
    • Journal of Korea Foresty Energy
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    • v.21 no.1
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    • pp.56-64
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    • 2002
  • 2kg of the dried leaves of Thuja orientalis Linnaeus were ground, extracted with acetone-$H_2O$(7:3, v/v), concentrated, and fractionated with a series of hexane, $CH_2C1_2$ EtOAc and water on a separators funnel. Each fraction was freeze dried to give dark-brown powder and a EtOAc soluble portion. of the powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. Spectrometric analyses such as NMR and FAB-MS including TLC were performed to characterize the structures of isolated compounds. The leave of Thuja orientalis Linnaeus contained a large amount of flavononol derivatives such as quercetin-3-O-$\alpha$-L-rhamnopyranoside and myricetin-3-O-$\alpha$-L-rhamnopyranoside in addition to a small amount of flavan compounds such as (+)-catechin and (+)-gallocatechin. The antioxidative activities of each fractions and isolated compounds were done by DPPH radical scavenging test, and all of them were indicated strong antioxidative activities.

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Tannins from Rubus coreanum

  • Lee, Yeon-Ah;Lee, Min-Won
    • Korean Journal of Pharmacognosy
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    • v.26 no.1
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    • pp.27-30
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    • 1995
  • Tannins were isolated from the stems of Rubus coreanum and identified as (-)-epicatechin, (+)-catechin, procyanidin B-4 and sanguiin H-4 by spectral analysis.

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Determination of Phytochemical Contents and Biological Activities from the Fruits of Elaeagnus multiflora

  • Lee, Jin-Hwan;Seo, Weon-Taek;Cho, Kye-Man
    • Preventive Nutrition and Food Science
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    • v.16 no.1
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    • pp.29-36
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    • 2011
  • The purpose of this study was to investigate the phytochemical contents and biological activities, including $\alpha$-glucosidase inhibitory activity and antioxidant activity, from the fruits of Elaeagnus multiflora using different solvent systems. The 50% ethanol extract of this species showed the most potent $\alpha$-glucosidase inibitory activity (88.5%) at a concentration of 1 mg/mL. Moreover, this extract also displayed the strongest antioxidant activity in each assay, showing 96.3% in DPPH scavenging activity, 98.2% in ABTS scavenging activity, and 2.5% in reducing power. The highest total phytochemical contents, including flavan-3-ols, phenolic acids, and flavonoids, were observed in the 50% ethanol extract. Interestingly, flavan-3-ols (3.150 mg/g) were detected at a significantly higher total content than those of phenolic acids (0.380 mg/g) and flavonoids (not detected). Additionally, the contents of individual phytochemicals showed remarkable differences, especially the epicatechin gallate (2.008 mg/g) and gallic acid (0.099 mg/g), which were the predominant constituents of each phytochemical type. Therefore, our results suggest that the 50% ethanol extract of E. multiflora fruits has strong biological activities, which are correlated with high phytochemical contents.

Proliferative Effects of Flavan-3-ols and Propelargonidins from Rhizomes of Drynaria fortunei on MCF-7 and Osteoblastic Cells

  • Chang, Eun-Ju;Lee, Won-Jung;Cho, Sung-Hee;Choi, Sang-Won
    • Archives of Pharmacal Research
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    • v.26 no.8
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    • pp.620-630
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    • 2003
  • The proliferative effects of thirty Oriental medicinal herbs on MCF-7 (estrogen-sensitive breast cancer cell line) and ROS 17/2.8 osteoblast-like cells were determined using the MTT assay. Methanol extracts from several herbs was found to show proliferative activity on the above two cell lines in the range of 5 to 100 $\mu$g/mL. Among these active herbs, the methanol extract from the rhizomes of Drynaria fortunei showed the most potent proliferative activity, and the cell proliferations were significantly increase by 136 and 158% in the MCF-7 and ROS 17/2.8 cells, respectively, when treated with 100 $\mu$ g/mL. Through a bioassay-guided separation, eight flavonoids, including four new flavan-3-ols and two propelargonidins, together with the known (-)-epiafzelechin and naringin, were isolated. Their chemical structures were characterized as (-)-epiafzelechin (1), (-)-epiafzelechin-3-O-$\beta$-D-allopyranoside (2), (-)-epiafzelechin-3-O-(6"-O-acetyl)-$\beta$-D-allopyranoside (3), 4$\beta$-carboxymethyl-(-)-epiafzelechin methyl ester (4), 4$\beta$-car-boxymethyl-(-)-epiafzelechin sodium salt (5), naringin (6), (-)-epiafzelechin-(4$\beta$\rightarrow8)-4$\beta$-car-boxymethylepiafzelechin methyl ester (7) and (-)-epiafzelechin-($4\beta\rightarrow8, 2\beta\rightarrowΟ\rightarrow7)-epiafzelechin-(4\beta\righarrow8)-epiafzelechin (8) by extensive 1D and 2D NMR spectroscopy. Most of these flavonoids, in the range of $10^{-15}∼10^{-6}$ M, accelerated the proliferation of MCF-7 cell, with compounds 7 and 8, in the range of $10^{-15}∼10^{-12}$ M, showing especially potent proliferation effects. Meanwhile, seven flavonoids, with the exception of compound 4, stimulated the proliferation of ROS 17/2.8 cells in the range of $10^{-15}∼10^{-6}$ M, with compounds 5-8 especially accelerating the proliferation, in dose-dependent manners ($10^{-15}∼10^{-9}$ M), and their proliferative effect was much stronger than that of $E_2$ and genistein. These results suggest that propelargonidin dimers and trimers isolated from the rhizomes of Drynaria fortunei may be useful as potential phytoestrogens, which play important physiological roles in the prevention of postmenopausal osteoporosis.

The Isolation of the Inhibitory Constitutents on Melanin Polymer Formation from the Leaves of Cercis chinensis (박태기나무의 잎으로부터 피부멜라닌 색소생성 억제성분의 분리)

  • Kim, So-Young;Kim, Jin-Joon;Jang, Tae-Soo;Chung, See-Ryun;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.30 no.4
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    • pp.397-403
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    • 1999
  • Tyrosinase plays an important role in the process of melanin polymer biosynthesis. Therefore, the enzyme inhibitors have been of great concern as cosmetics to have skin-whitening effects on the local hyperpigmentation. During the search for new inhibitory compounds on melanin polymer biosynthesis from natural sources, MeOH extracts of 589 higher plants were tested for the inhibitory effect on tyrosinase activity by the muschroom tyrosinase assay in vitro. Among plants tested, the leaves of Cercis chinensis exhibited potent inhibitory effect on mushroom tyrosinase activity. Subsequently seven active compounds were isolated from the ethyl acetate soluble part of acetone extract of the leaves of C. chinensis by the activity guided fractionation monitoring the inhibitory effect on tyrosinase activity. Their chemical structures were identified as $kaempferol-3-0-{\alpha}-L-rhamnoside$, quercitrin, $myricetin-3-0-{\alpha}-L-rhamnoside$, myricetin-3-0-(2'-O-galloyl)- ${\alpha}$ -L-rhamopyranoside (desmanthin), (-)-epicatechin-3-0-gallate, (-)-epigallocatechin-3-0-gallate, and methyl gallate on the basis of the speculation of spectral data and chemical reaction. Among the flavonol rhamnosides, myricetin-3-0-(2'-O-galloyl)- -L-rhamnoside(desmanthin) showed most potent inhibitory effect on tyrosinase activity and the structure of B-ring in flavonol moiety was related to the activity. (-)-Epigallocatechin-3-O-gallate having pyrogallol group in flavan-3-ol moiety exhibited more potent inhibitory effect than (-)-epicatechin-3-0-gallate having catechol group in flavan-3-ol moiety on mushroom tyrosinase activity.

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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.

DPPH Radical Scavenging Activity of Phenolic Compounds Isolated from the Stem Wood of Acer tegmentosum (산겨릅나무 목질부에서 분리한 페놀성 화합물의 DPPH 라디칼 소거활성)

  • Kwon, Dong-Joo;Kim, Jin-Kyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.39 no.1
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    • pp.104-112
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    • 2011
  • There have been few reports on the constituents and biological activity of stem bark of $Acer$ $tegmentosum$, and no phytochemical and biological studies have been reported for stem wood of $A.$ $tegmentosum$. Two flavan 3-ols (1 and 2), three phenolic acid/alcohols (3~5), and two coumarins (6 and 7) were isolated from the stem wood of $A.$ $tegmentosum$ by repeated column chromatography. The structure of isolated compounds were identified as (+)-catechin (1), (-)-epicatechin (2), $p$-hydroxybenzaldehyde (3), syringic alcohol (4), $p$-tyrosol (5), scopoletin (6), and cleomiscosin A (7) on the basis of spectroscopic evidences such as $^1H$-NMR, $^{13}C$-NMR, 2D-NMR and MS spectrum. $p$-Hydroxybenzaldehyde (3), syringic alcohol (4), scopoletin (6), and cleomiscosin A (7) have not been reported from this plant so far. (+)-Catechin (1) and (-)-epicatechin (2) showed the higher 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity than butylated hydroxyanisole (BHA) used as a positive control.