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来自赤桉树枝的酚类化合物。

Phenolic compounds from the branches of Eucalyptus maideni.

机构信息

State Key Laboratory of Phytochemistry and Plant Resources of West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China.

出版信息

Chem Biodivers. 2012 Jan;9(1):123-30. doi: 10.1002/cbdv.201100021.

DOI:10.1002/cbdv.201100021
PMID:22253109
Abstract

Three new phenolic compounds, eucalmaidin F (1), (3S)-5-guaiacyl-3-hydroxypentanoic acid (2), and 8-β-C-glucopyranosyl-5,7-dihydroxy-2-isobutylchromone (3), were isolated from the branches of E. maideni, together with 30 known compounds, including four phenylpropanoids, three lignans, four phloroglucinol glucosides, five dihydroflavonoids, seven simple phenolic compounds, six terpenoids, and glycerol. The new structures were established by spectroscopic studies (MS, and 1D- and 2D-NMR), chemical degradation, and modified Mosher's method. Compounds 3, guaiacylglycerol, 3-hydroxy-1-(4-hydroxyphenyl)propan-1-one, caffeic acid, (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid, (7'S,8R,8'R)-lyoniresinol, (+)-lyoresinol 3α-O-α-L-rhamnopyranoside, garcimangosone, phlorocetophenone 2'-glucopyranoside, (+)-taxifolin 3α-O-α-L-rhamnopyranoside, (+)-aromadendrin, (+)-taxifolin, resveratrol, piceatannol, 3,4,5-trihydroxyphenol. Tachiaside, gallic acid, macrocapals A und G, and oleuropeic acid were evaluated for their cytotoxicities against five human cancer cell lines. Resveratrol, piceatannol, gallic acid, and macrocapal G exhibited moderate inhibitory effects on human myeloid heukemia HL-60 cell, with IC(50) values of 22.05, 22.05, 7.75, and 31.93 μM, respectively; and only macrocapal G showed inhibitory effect on hepatocellular carcinoma SMMC-7721 cell, with an IC(50) value of 26.75 μM.

摘要

从 E. maideni 的树枝中分离得到了 3 种新的酚类化合物,即 eucalmaidin F(1)、(3S)-5-愈创木基-3-羟基戊酸(2)和 8-β-C-吡喃葡萄糖基-5,7-二羟基-2-异丁基色酮(3),以及 30 种已知化合物,包括 4 种苯丙素类、3 种木质素类、4 种间苯三酚葡萄糖苷类、5 种二氢黄酮类、7 种简单酚类化合物、6 种萜类化合物和甘油。新结构通过光谱研究(MS 和 1D 和 2D-NMR)、化学降解和改良的 Mosher 法确定。化合物 3、愈创木基甘油、3-羟基-1-(4-羟基苯基)-1-丙酮、咖啡酸、(2E)-3-(4-羟基苯基)-2-丙烯酸、(7'S,8R,8'R)-lyoniresinol、(+)-lyoresinol 3α-O-α-L-鼠李吡喃糖苷、garcimangosone、phlorocetophenone 2'-吡喃葡萄糖苷、(+)-taxifolin 3α-O-α-L-鼠李吡喃糖苷、(+)-aromadendrin、(+)-taxifolin、resveratrol、piceatannol、3,4,5-三羟基苯酚。Tachiaside、没食子酸、大冠马兜铃素 A 和 G、橄榄酸被评估对五种人癌细胞系的细胞毒性。白藜芦醇、白藜芦醇、没食子酸和大冠马兜铃素 G 对人髓性白血病 HL-60 细胞表现出中等抑制作用,IC50 值分别为 22.05、22.05、7.75 和 31.93 μM;只有大冠马兜铃素 G 对肝癌 SMMC-7721 细胞表现出抑制作用,IC50 值为 26.75 μM。

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