• Title/Summary/Keyword: rhododendrol

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Cytotoxic Constituents of Rhododendron brachycarpum (만병초의 세포독성 성분)

  • Jang Gi Uk;Choi Sang Un;Lee Kang Ro
    • YAKHAK HOEJI
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    • v.49 no.3
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    • pp.244-248
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    • 2005
  • From the methanol extract of Rhododendron brachycarpum four triterpenes, three phenylpropanes and a diterpene alkaloid were isolated. Their structures were identified as glutinol (1), 3$\beta$-hydroxyurs-12-ene (2), $\beta$-sitosterol (3), (E)-P-hydrox-ycinnamic acid hexadecylester (4), (-)-rhododendrol (5), (+)-rhododendrol (6), 3$\beta$-hydroxyurs-12-en-28-oic acid (7) and gray-anotoxin I (8) by spectroscopic methods. Compound 8 showed moderate cytotoxicity against five cultured human tumor cell lines with $ED_{50}$ values of $3.21\~4.05 {\mu}g/ml$. The other compounds were of marginal activity against the tested cell lines.

A Study on the Extractives of Domestic Major Softwood Needles(I) - Antioxidant Activity of the Extractives from the Needles of Abies koreana Maximowicz and Abies holophylla Wilson - (국내산 주요 침엽수 잎의 추출성분(I) - 구상나무(Abies koreana Maximowicz)와 전나무(Abies holophylla Wilson) 잎 추출성분의 항산화 활성 -)

  • Lee, Sang-Keug;Choi, Don-Ha;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.3
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    • pp.73-83
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    • 2006
  • The dried needles (1.5 kg) of Abies koreana and Abies holophylla were ground, extracted with acetone-$H_2O$ (7:3, v/v), concentrated, and fractionated with a series of hexane, methylene chloride, ethyl acetate and water on a separatory funnel. Each fraction was freeze dried, then a portion of ethyl acetate soluble powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. The isolated compounds were identified by cellulose TLC, $^1H$, $^{13}C-NMR$, COSY, HETCOR, FAB and EI-MS. The needles of Abies koreana and Abies holophylla contained a large amount of aromadendrin-7-O-${\beta}$-D-glucopyranoside (compound III), polydatin (compound VI), (-)-rhododendrol-2-O-${\beta}$-D-glucopyranoside (compound VII), in addition to a small amount of (+)-catechin (compound I), kaempferol-3-O-${\beta}$-D-glucopyranoside (compound IV), myricetin-3-O-${\beta}$-D-glucopyranoside (compound V), naringenin-7-O-${\beta}$-D-glucopyranoside (compound II). DPPH analysis was also tested to investigate the antioxidative effects on the isolated compounds and (+)-catechin and polydatin were effective.

Taxoids, Lignans, and Simple Phenolic Compounds from a Sample of the Needles of Himalayan Taxus baccata

  • Das, Biswanath;Anjani, G.;Kashinatham, A.;Venkataiah, B.;Rao, S. Padma
    • Natural Product Sciences
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    • v.4 no.2
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    • pp.78-83
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    • 1998
  • Chemical investigation on a sample of the needles of Himalayan Taxus baccata has resulted in the isolation of several taxoids including taxol (1) 10-deacetyl-baccatin III (2) and 2-deacetoxytaxinine J (3) along with different lignans (6 and 7) and simple phenolics (8, 9, 10, 11 and 12). The occurrence of 4-(4'-hydroxyphenyl)-butane-2-one and 4-(4'-hydroxyphenyl)-trans-but 3-ene-2-one (8) in Taxus species is reported for the first time. The $^{13}C-NMR$ spectral data of two rearranged taxiod constituents, brevifoliol (4) and 13-decinnamoyltaxchinin B (5) are presented. The acid-catalyzed decomposition of taxol has been discussed. The synthesis of other two constituents, rhododendrol (10) and hibalactone (7) has been described.

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Chemical Constituents of Abies koreana Leaves with Inhibitory Activity against Nitric Oxide Production in BV2 Microglia Cells

  • Baek, Sa-Wang;Kim, E. Ray;Kim, Jin-Woong;Kim, Young-Choong
    • Natural Product Sciences
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    • v.17 no.3
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    • pp.175-180
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    • 2011
  • Eleven compounds were isolated from fresh leaves of Abies koreana (Pinaceae), and structures of these compounds were determined to be 3-hydroxy-2-methyl-4-pyrone (1), maltol-3-O-${\beta}$-D-glucoside (2), (-)-epicatechin (3), naringenin 7-O-${\beta}$-D-glucopyranoside (4), naringenin-7-O-rhamnoglucoside (5), kaempferol 3-O-${\beta}$-D-glucopyranoside (6), (+)-isolariciresinol (7), secoisolariciresinol (8), rhododendrol (9), ferulic acid (10) and 4-(4-hydroxyphenyl)butan-2-one (rheosmin) (11) by comparing $^1H$-, $^{13}C$-NMR and MS spectroscopic data with reference values. Compounds 3, 5, 7, 8, 9, 10, 11 were isolated for the first time from A. koreana. Among eleven isolates, compounds 1, 7 and 11 showed inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 microglia in a concentration dependent manner.

The Cytotoxic Constituents of Betula platyphylla and their Effects on Human Lung A549 Cancer Cells

  • Yang, Eun-Ju;An, Ju-Hee;Son, Youn Kyoung;Yeo, Joo-Hong;Song, Kyung-Sik
    • Natural Product Sciences
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    • v.24 no.4
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    • pp.219-224
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    • 2018
  • During the screening for cytotoxic compounds from plants grown in Korea, Betula platyphylla (BP) showed potent activity against the adenocarcinomic human alveolar basal epithelial A549 cell line. To identify the cytotoxic components from BP, the $CH_2Cl_2$ fraction with the most significant cytotoxic effect was applied to the column chromatographies. Seven compounds were isolated: lupeol (1), betulinic acid (2), (-)-rhododendrol (3), platyphyllenone (4), platyphyllone (5), (-)-centrolobol (6), and oleanolic acid (7). Among them, three diarylheptanoids (4 - 6) exhibited cytotoxicity toward A549 cells. Especially, $50{\mu}M$ of 4 reduced A549 cell viability to $18.93{\pm}0.82%$ compared to control ($100.00{\pm}21.48%$). Lactate dehydrogenase (LDH) leakage and intracellular reactive oxygen species (ROS) production were also induced by $50{\mu}M$ 4. This is the first report on the cytotoxic effect of BP-derived diarylheptanoids 4-6 against A549 cells. The compound 4 may be useful for the development of early hit compounds for non-small cell lung carcinoma, but the consideration about selectivity of 4 is required since 4 also showed the cytotoxicity in the human normal lung epithelial BEAS-2B cell line.