Biotransformation of Bioactive Isocaryolanes by Botrytis cinerea

被引:14
作者
Ascari, Jociani [2 ]
Diamantino Boaventura, Maria Amelia [2 ]
Takahashi, Jacqueline Aparecida [2 ]
Duran-Patron, Rosa [1 ]
Hernandez-Galan, Rosario [1 ]
Macias-Sanchez, Antonio J. [1 ]
Collado, Isidro G. [1 ]
机构
[1] Univ Cadiz, Fac Ciencias, Dept Quim Organ, Puerto Real 11510, Spain
[2] Univ Fed Minas Gerais, Inst Ciencias Exatas, Dept Quim, BR-31270901 Belo Horizonte, MG, Brazil
来源
JOURNAL OF NATURAL PRODUCTS | 2011年 / 74卷 / 08期
关键词
MITSUNOBU CONDITIONS; CARYOPHYLLENE OXIDE; ANTIFUNGAL ACTIVITY; METABOLITES; INHIBITION; SESQUITERPENOIDS; REARRANGEMENT; PATCHOULOL; GINSENOL; CULTURE;
D O I
10.1021/np1009465
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The metabolism of the fungistatic agent (8R,9R)-8-methoxyisocaryolan-9-ol (4) by the fungus Botrytis cinerea has been investigated. Biotransformation of compound 4 yielded compounds 5 and 6-9. No dihydrobotrydial is observed after 4 days of incubation of compound 4. Separate biotransformation of (8R,9R)-isocaryolane-8,9-diol (5) yielded compounds 7-11. The evaluation of the fungistatic activity against B. cinerea of compounds 4, 5, and 6 is reported. (4R,8R,9R)-8-Methoxyisocaryolane-9,15-diol (6), a major metabolite of (8R,9R)-8-methoxyisocaryolan-9-ol (4), shows a much reduced biological activity when compared with the parent compound. Isocaryolane derivatives 6-11 are described for the first time.
引用
收藏
页码:1707 / 1712
页数:6
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