假荆芥属抗分枝杆菌代谢产物：抗结核分枝杆菌菌株的罗勒酮衍生物。

Antimycobacterial metabolites from Plectranthus: royleanone derivatives against Mycobacterium tuberculosis strains.

机构信息

Faculdade de Farmácia da Universidade de Lisboa, iMed.UL, Av. Prof. Gama Pinto, PT-1649-003 Lisboa.

出版信息

Chem Biodivers. 2010 Apr;7(4):922-32. doi: 10.1002/cbdv.200900099.

DOI:10.1002/cbdv.200900099

PMID:20397225

Abstract

The antimycobacterial activities of eight diterpenes, 1-8, isolated previously from Plectranthus and eleven esters, 9-19, of 7alpha-acetoxy-6beta,12-dihydroxyabieta-8,12-diene-11,14-dione (5) were evaluated against the MTB strains H(37)Rv and MDR. Only diterpenoids with a quinone framework revealed anti-MTB activity. Abietane 5 and its 6,12-dibenzoyl, 12-methoxybenzoyl, 12-chlorobenzoyl, and 12-nitrobenzoyl esters, 9, 11, 12, and 13, respectively, showed potent activities against the MDR strain with MIC values between 3.12 and 0.39 microg/ml. Cytotoxic activities towards 3T3 and Vero cells were also evaluated. Compound 11, with the best selectivity index, may be a suitable lead for further chemical modifications. The complete structural elucidation of the new esters, 9-14, 16, 18, and 19, as well as the NMR data of known derivatives 15 and 17 are reported.

摘要

八种 previously 从 Plectranthus 中分离得到的二萜类化合物 1-8 和 11-19 个 7alpha-乙酰氧基-6beta，12-二羟基贝壳杉-8，12-二烯-11，14-二酮（5）的酯类化合物，评估了它们对 MTB 株 H(37)Rv 和 MDR 的抗微生物活性。只有具有醌骨架的二萜类化合物显示出抗 MTB 活性。贝壳杉烷 5 及其 6,12-二苯甲酰基、12-甲氧基苯甲酰基、12-氯苯甲酰基和 12-硝基苯甲酰基酯 9、11、12 和 13 对 MDR 菌株表现出强大的活性，MIC 值在 3.12 和 0.39 microg/ml 之间。还评估了对 3T3 和 Vero 细胞的细胞毒性活性。具有最佳选择性指数的化合物 11 可能是进一步化学修饰的合适先导化合物。报告了新酯 9-14、16、18 和 19 以及已知衍生物 15 和 17 的 NMR 数据的完整结构阐明。