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灰葡萄孢的植物毒性活性和代谢及异贝壳杉烷衍生物的构效关系。

Phytotoxic activity and metabolism of Botrytis cinerea and structure-activity relationships of isocaryolane derivatives.

机构信息

Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Avenida Presidente Antônio Carlos, 6627, 31270-901, Belo Horizonte, MG, Brazil.

出版信息

J Nat Prod. 2013 Jun 28;76(6):1016-24. doi: 10.1021/np3009013. Epub 2013 Jun 3.

DOI:10.1021/np3009013
PMID:23730968
Abstract

Research has been conducted on the biotransformation of (8S,9R)-isocaryolan-9-ol (4a) and (1S,2S,5R,8S)-8-methylene-1,4,4-trimethyltricyclo[6.2.1.0(2,5)]undecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4a yielded compounds 6-9, while the biotransformation of compound 5a yielded compounds 10-13. The activity of compounds 4a and 5a against B. cinerea has been evaluated. (8R,9R)-Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3, 4a, and 5a, together with their biotransformation products 6-8, 10, and 14-17, on the germination and radicle and shoot growth of Lactuca sativa (lettuce) has also been determined. Compounds 7-13 are described for the first time.

摘要

已对真菌植物病原菌 Botrytis cinerea 对(8S,9R)-异卡波醇-9-醇(4a)和(1S,2S,5R,8S)-8-亚甲基-1,4,4-三甲基三环[6.2.1.0(2,5)]十一烷-12-醇(5a)的生物转化进行了研究。化合物 4a 的生物转化生成了化合物 6-9,而化合物 5a 的生物转化生成了化合物 10-13。已经评估了化合物 4a 和 5a 对 B. cinerea 的活性。(8R,9R)-异卡波醇-8,9-二醇(6)是化合物 4a 的主要代谢产物,与无活性的母体化合物 4a 相比具有活性。还确定了异卡波烷 3、4a 和 5a 及其生物转化产物 6-8、10 和 14-17 对莴苣(生菜)的发芽以及根和芽生长的影响。化合物 7-13 为首次报道。

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