藤仓赤霉菌对两种对映-海松-9(11),15-二烯衍生物的生物转化
Biotransformation of two ent-Pimara-9(11),15-diene derivatives by Gibberella fujikuroi.
作者信息
Fraga Braulio M, Guillermo Ricardo, Hernández Melchor G, Chamy María C, Garbarino Juan A
机构信息
Instituto de Productos Naturales y Agrobiología, CSIC, P.O. Box 195, 38206-La Laguna, Tenerife, Canary Islands, Spain.
出版信息
J Nat Prod. 2009 Jan;72(1):87-91. doi: 10.1021/np800647v.
The incubation of 19-hydroxy-13-epi-ent-pimara-9(11),15-diene (4) with Gibberella fujikuroi gave 8 alpha,19-dihydroxy-9 alpha,11alpha-epoxy-13-epi-ent-pimara-15-ene (6), 7-oxo-11 alpha,19-dihydroxy-13-epi-ent-pimara-8(9),15-diene (7), 7-oxo-11beta,19-dihydroxy-13-epi-ent-pimara-8(9),15-diene (9), and 8 alpha,19-dihydroxy-9 alpha,11 alpha:15,16-diepoxy-13-epi-ent-pimarane (11), while the feeding of 13-epi-ent-pimara-9(11),15-diene-19-oic acid (5) with this fungus afforded 1-oxo-2 alpha,9 alpha-dihydroxy-13-epi-ent-pimara-11,15-dien-19-oic acid (13), 1-oxo-2 beta,9 alpha-dihydroxy-13-epi-ent-pimara-11,15-dien-19-oic acid (14), 13-epi-ent-pimara-9(11),15-dien-1,19-dioic acid 1,2-lactone (15), and 1-oxo-12 beta-hydroxy-13-epi-ent-pimara-9(11),15-dien-19-oic acid (16). In both biotransformations, the main reaction was the epoxidation of the 9(11)-double bond, followed by rearrangement to afford allylic alcohols. The formation of lactone 15 represents the first time that a Baeyer-Villiger oxidation has been observed in a microbiological transformation with this fungus.
将19-羟基-13-表-对映-海松-9(11),15-二烯（4）与藤仓赤霉菌一起培养，得到了8α,19-二羟基-9α,11α-环氧-13-表-对映-海松-15-烯（6）、7-氧代-11α,19-二羟基-13-表-对映-海松-8(9),15-二烯（7）、7-氧代-11β,19-二羟基-13-表-对映-海松-8(9),15-二烯（9）以及8α,19-二羟基-9α,11α:15,16-二环氧-13-表-对映-海松烷（11）；而用这种真菌对13-表-对映-海松-9(11),15-二烯-19-酸（5）进行培养时，得到了1-氧代-2α,9α-二羟基-13-表-对映-海松-11,15-二烯-19-酸（13）、1-氧代-2β,9α-二羟基-13-表-对映-海松-11,15-二烯-19-酸（14）、13-表-对映-海松-9(11),15-二烯-1,19-二酸1,2-内酯（15）以及1-氧代-12β-羟基-13-表-对映-海松-9(11),15-二烯-19-酸（16）。在这两种生物转化过程中，主要反应都是9(11)-双键的环氧化，随后重排生成烯丙醇。内酯15的形成代表了首次在这种真菌的微生物转化中观察到拜耳-维利格氧化反应。
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