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立方树脂杀虫剂中的新型生物活性黄酮类化合物和芪类化合物。

New bioactive flavonoids and stilbenes in cubé resin insecticide.

作者信息

Fang N, Casida J E

机构信息

Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy and Management, University of California, Berkeley, California 94720-3112, USA.

出版信息

J Nat Prod. 1999 Feb;62(2):205-10. doi: 10.1021/np980119+.

DOI:10.1021/np980119+
PMID:10075742
Abstract

Fractionation of cubé resin from Lonchocarpus utilus and L. urucu roots led to the isolation and identification of 11 minor flavonoids and stilbenes containing the gem-dimethylpyran moiety or a dihydrodiol derivative thereof. The eight new compounds were as follows: the isoflavonoid cis-4'',5''-dihydro-4'',5' '-dihydroxylonchocarpusone (2); four (2S)-6-(gamma, gamma-dimethylallyl)-6'',6''-dimethylpyran[2'',3'':7, 8]flavanones with substituents of 5-hydroxy-3',4'-dimethoxy (3), 5, 3'-dihydroxy-4'-methoxy (4), 5,4'-dihydroxy-3'-methoxy (5), and 3', 4'-dimethoxy (6); and three 6'',6''-dimethylpyran[2'',3'':3', 4']stilbenes with 4-hydroxy-5'-methoxy (9), 3,5'-dimethoxy-4-hydroxy (10) and 3,4,5-trimethoxy (11) substitution patterns. Structure-activity relationships for inhibition of NADH:ubiquinone oxidoreductase activity (bovine heart electron transport particles) and phorbol ester-induced ornithine decarboxylase activity (cultured MCF-7 cells) generally parallel those for cytotoxicity (MCF-7 and Hepa 1clc7 cells).

摘要

对来自利氏罗望子和乌鲁库罗望子根的立方树脂进行分级分离,得到并鉴定了11种含有偕二甲基吡喃部分或其二氢二醇衍生物的次要黄酮类化合物和芪类化合物。这8种新化合物如下:异黄酮顺式-4'',5''-二氢-4'',5''-二羟基罗望子酮(2);4种(2S)-6-(γ,γ-二甲基烯丙基)-6'',6''-二甲基吡喃[2'',3'':7,8]黄烷酮,其取代基分别为5-羟基-3',4'-二甲氧基(3)、5,3'-二羟基-4'-甲氧基(4)、5,4'-二羟基-3'-甲氧基(5)和3',4'-二甲氧基(6);以及3种6'',6''-二甲基吡喃[2'',3'':3',4']芪类化合物,其取代模式分别为4-羟基-5'-甲氧基(9)、3,5'-二甲氧基-4-羟基(10)和3,4,5-三甲氧基(11)。抑制NADH:泛醌氧化还原酶活性(牛心电子传递颗粒)和佛波酯诱导的鸟氨酸脱羧酶活性(培养的MCF-7细胞)的构效关系通常与细胞毒性(MCF-7和Hepa 1clc7细胞)的构效关系平行。

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