柳叶柴胡中8S-十七碳-2(Z),9(Z)-二烯-4,6-二炔-1,8-二醇的抗菌活性及绝对构型

Antibiotic activity and absolute configuation of 8S-heptadeca-2(Z),9(Z)-diene-4,6-diyne-1,8-diol from Bupleurum salicifolium.

作者信息

Estevez-Braun A, Estevez-Reyes R, Moujir L M, Ravelo A G, Gonzalez A G

机构信息

Instituto Universitario de Bio-Orgánica, Universidad de La Laguna, Canary Islands, Spain.

出版信息

J Nat Prod. 1994 Aug;57(8):1178-82. doi: 10.1021/np50110a009.

DOI:10.1021/np50110a009

PMID:7964800

Abstract

A polyacetylene has been isolated from Bupleurum salicifolium. Its structure and absolute configuration were determined to be 8S-heptadeca-2(Z),9(Z)-diene-4,6-diyne-1,8-diol [1] by means of 1H- and 13C-nmr spectroscopic studies, including 1H-13C heteronuclear correlation (HMQC) and long-range correlation spectra with inverse detection (HMBC). Its absolute configuration was determined by application of the Horeau method. This compound exhibited significant antibiotic activity against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis. Also isolated during this investigation were the known compounds; betulin, herniarin, 6,7,8-trimethoxycoumarin, p-hydroxyphenethyl alcohol, pluviatolide, guamaroline, bursehernin, guayadequiol, kaerophyllin, and matairesinol dimethyl ether.

摘要

从柳叶柴胡中分离出了一种聚乙炔。通过1H-和13C-核磁共振光谱研究，包括1H-13C异核相关（HMQC）和反向检测的远程相关光谱（HMBC），确定其结构和绝对构型为8S-十七碳-2(Z),9(Z)-二烯-4,6-二炔-1,8-二醇[1]。其绝对构型通过应用霍罗方法确定。该化合物对革兰氏阳性菌金黄色葡萄球菌和枯草芽孢杆菌表现出显著的抗菌活性。在本次研究中还分离出了已知化合物；桦木醇、蛇床子素、6,7,8-三甲氧基香豆素、对羟基苯乙醇、伞形花内酯、愈创木罗啉、紫堇色菌素、愈创木二醇、芹菜素和罗汉松脂素二甲醚。