来自灰叶拟层孔菌叶片的大叶素型双环[3.2.1]辛烷类新木脂素

Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.

作者信息

Coy Ericsson D, Cuca Luis E, Sefkow Michael

机构信息

Departamento de Quimica, Facultad de Ciencias, Universidad Nacional de Colombia, AA 14490, Bogota D.C., Colombia.

出版信息

J Nat Prod. 2009 Jul;72(7):1245-8. doi: 10.1021/np9000569.

DOI:10.1021/np9000569

PMID:19548690

Abstract

Four new macrophyllin-type bicyclo[3.2.1]octanoid neolignans, (7S,8R,3'S,5'R)-Delta(8')-5,5',3'-trimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2',4'-dioxo-7.3',8.5'-neolignan (cinerin A), 1, (7R,8R,3'S,4'R,5'R)-Delta(8')-4'-hydroxy-5,5'-dimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (cinerin B), 2, (7S,8R,3'R,4'S,5'R)-Delta(8')-4'-hydroxy-5,5',3'-trimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (cinerin C), 3, and (7S,8R,2'R,3'S,5'R)-Delta(8')-2'-hydroxy-5,5'-dimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-4'-oxo-7.3',8.5'-neolignan (cinerin D), 4, along with the known diterpene kaurenoic acid 5, were isolated from the leaves of Pleurothyrium cinereum. The structures and configuration of these compounds were determined by extensive spectroscopic analysis. Cinerins A-D (1-4) were tested for their inhibition efficacy of platelet activating factor (PAF)-induced aggregation of rabbit platelets. Compound 3 was the most potent PAF antagonist. Compounds 1-5 were tested against Mycobacterium tuberculosis (H(37)Rv strain) using the MABA method. Compound 5 induced 91.3% growth inhibition at 50 microg mL(-1). Compounds 1-5 showed no significant inhibitory activity against some Gram-positive and Gram-negative bacteria by the agar-well diffusion method.

摘要

从灰叶拟层孔菌的叶子中分离出了4种新的大叶木兰型双环[3.2.1]辛烷类新木脂素，即(7S,8R,3'S,5'R)-Δ(8')-5,5',3'-三甲氧基-3,4-亚甲二氧基-2',3',4',5'-四氢-2',4'-二氧代-7.3',8.5'-新木脂素（灰菌素A），1；(7R,8R,3'S,4'R,5'R)-Δ(8')-4'-羟基-5,5'-二甲氧基-3,4-亚甲二氧基-2',3',4',5'-四氢-2'-氧代-7.3',8.5'-新木脂素（灰菌素B），2；(7S,8R,3'R,4'S,5'R)-Δ(8')-4'-羟基-5,5',3'-三甲氧基-3,4-亚甲二氧基-2',3',4',5'-四氢-2'-氧代-7.3',8.5'-新木脂素（灰菌素C），3；以及(7S,8R,2'R,3'S,5'R)-Δ(8')-2'-羟基-5,5'-二甲氧基-3,4-亚甲二氧基-2',3',4',5'-四氢-4'-氧代-7.3',8.5'-新木脂素（灰菌素D），4，同时还分离出了已知的二萜类化合物贝壳杉烯酸5。通过广泛的光谱分析确定了这些化合物的结构和构型。测试了灰菌素A - D（1 - 4）对血小板活化因子（PAF）诱导的兔血小板聚集的抑制效果。化合物3是最有效的PAF拮抗剂。使用MABA方法测试了化合物1 - 5对结核分枝杆菌（H(37)Rv菌株）的活性。化合物5在50 μg mL(-1)时诱导91.3%的生长抑制。通过琼脂孔扩散法，化合物1 - 5对一些革兰氏阳性和革兰氏阴性细菌没有显著的抑制活性。