• Title/Summary/Keyword: (-)-epiafzelechin

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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.

Flavonoids from Kyllinga brevifolia var. leiolepsis (수오공의 Flavonoid 성분)

  • Lew, Jung-Hie;Kwak, Jong-Hwan;Zee, Ok-Pyo;Lee, Kang-Ro
    • Korean Journal of Pharmacognosy
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    • v.29 no.2
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    • pp.71-74
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    • 1998
  • Four flavonoids were isolated from the whole plant of Kyllinga brevifolia var. leiolepsis. Their structures were identified as quercetin, (-)-epiafzelechin, vitexin and orientin on the basis of spectral data. This is the first report of the identification of quercetin, (-)-epiafzelechin and orientin from Kyllinga genus.

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Isolation of Polyphenol from Green Tea by HPLC and Its Physiological Activities (HPLC에 의한 녹차의 polyphenol 화합물의 분리 및 polyphenol의 생리활성)

  • Woo, Hee-Seob;Choi, Hee-Jin;Han, Ho-Suk;Park, Jung-Hye;Son, Jun-Ho;An, Bong-Jeun;Son, Gyu-Mok;Choi, Cheong
    • Korean Journal of Food Science and Technology
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    • v.35 no.6
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    • pp.1199-1203
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    • 2003
  • Polyphenols were isolated from Korean green tea using Sephadex LH-20 and HPLC. The isolated polyphenols were procyanidin B-4, procyanidin B-2-3,3'-digallate, prodelphinidin C-2-3,3'-di-O-digallate, (+)-catechin-3-O-rhamnose, procyandin B-5, procyanidin B-7-3-0-gallate, gallate, 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 and (+)-taxifolin-3-O-D-xyloside. The inhibitory effects of prodelphinidin C-2-3,3'-di-O-gallate and procyanidin B-2-3,3'-digallate $(at\;100{\mu}M)$ on angiotensin.converting enzyme were 68.8 and 54.6%, respectively, while the inhibitory effects of prodelphinidin C-2-3,3'-di-O-gallated and procyanidin B-2-3,3'-digallate $(at\;100{\mu}m)$ on xanthine oxidase were 54.5 and 38.2%, respectively. Lastly, the inhibitory activities of prodelphinidin C-2-3,3'-di-O-gallate $(at\;100{\mu}m)$ on tyrosinase was 42.1%.

Flavonoid Constituents of Acacia catechu (Acacia catechu의 플라보노이드 성분)

  • Hong, Seong Su;Choi, Yun-Hyeok;Suh, Hwa-Jin;Kang, Min-Jung;Shin, Jung-Hye;Kwon, Oh-Oun;Oh, Joa Sub
    • Journal of Applied Biological Chemistry
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    • v.58 no.2
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    • pp.189-194
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    • 2015
  • Ten compounds were isolated from the ethanolic extract of the leaves of Acacia catechu (Fabaceae), and their structures were identified as nine flavonoids [(+)-catechin (1), (-)-epicatechin (2), (+)-afzelechin (3), (-)-epiafzelechin (4), (+)-mesquitol (5), kaempferol (6), quercetin (7), quercetin 3-methyl ether (8), and caryatin (9)] and an ellagic acid (10). The chemical structures of these compounds were identified on the basis of spectroscopic methods (mass spectrometry, 1D and 2D nuclear magnetic resonance) and comparison with literature values. This is the first time that the isolation of caryatin (9) has been reported from Acacia genus.