通过逆流色谱法从三齿拉瑞阿中分离抗HIV-1木脂素。

Isolation of anti-HIV-1 lignans from Larrea tridentata by counter-current chromatography.

作者信息

Gnabre J N, Ito Y, Ma Y, Huang R C

机构信息

Department of Biology, Johns Hopkins University, Baltimore, MD 21218-2685, USA.

出版信息

J Chromatogr A. 1996 Jan 8;719(2):353-64. doi: 10.1016/0021-9673(95)00727-x.

DOI:10.1016/0021-9673(95)00727-x

PMID:8581122

Abstract

Several lignans, mostly new, were isolated from Larrea tridentata by assay-guided counter-current chromatography (CCC). Using the secreted alkaline phosphatase bioassay of HIV Tat transactivation and the two-phase hexane-ethyl acetate-methanol-water solvent system, two major components (Gr and Lo) were identified as anti-HIV active principles. The chemical structures of the constituents of Gr (G1-G4) and Lo (L1-L4) were determined by GC-MS and NMR. After optimization of isolation conditions, a large-scale isolation with the chloroform-methanol-water system yielded five constituents (FB1-FB5). The most predominant anti-HIV compound FB2 (denoted Malachi 4:5-6 or mal.4), which occurs in 0.23% yield, was separated from its FB1 isomer (0.13% yield). Compound FB4 and two tricyclic lignans (FB3 and FB5) were also isolated in a substantial amount for further testing of their anti-HIV activities. These compounds may represent a new class of anti-HIV agents with important clinical relevance.

摘要

通过分析导向逆流色谱法（CCC）从三齿拉瑞阿中分离出了几种木脂素，其中大部分是新的。利用HIV Tat反式激活的分泌碱性磷酸酶生物测定法以及正己烷 - 乙酸乙酯 - 甲醇 - 水两相溶剂系统，确定了两种主要成分（Gr和Lo）为抗HIV活性成分。通过气相色谱 - 质谱联用（GC-MS）和核磁共振（NMR）确定了Gr（G1 - G4）和Lo（L1 - L4）成分的化学结构。在优化分离条件后，用氯仿 - 甲醇 - 水系统进行大规模分离得到了五种成分（FB1 - FB5）。含量最丰富的抗HIV化合物FB2（命名为玛拉基书4:5 - 6或mal.4），产率为0.23%，从其FB1异构体（产率0.13%）中分离出来。化合物FB4以及两种三环木脂素（FB3和FB5）也大量分离出来，用于进一步测试它们的抗HIV活性。这些化合物可能代表了一类具有重要临床意义的新型抗HIV药物。