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化学学报
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化学学报 ›› 1982, Vol. 40 ›› Issue (7): 629-636. 上一篇    下一篇

论文

16,17α-环氧-5α-和5β-孕甾-3β-醇-20-酮和16,17α-环氧-16β-甲基-5α-⊿9(11)-孕甾烯-3β-醇-20-酮的微生物脱氢

吴照华, 周维善   

  1. 中国科学院上海有机化学研究所
  • 投稿日期:1981-01-12 发布日期:2013-06-03
  • 通讯作者: 周维善

MICROBIAL TRANSFORMATIONS OF 16, 17α-OXIDO-5α-AND 5β-PREGNANE-3β-OL-20-ONE AND 16, 17α-OXIDO-16β-METHYL-5α-⊿9(11)-PREGNENE-3β-OL-20-ONE

WU ZHAO-HUA, ZHOU WEI-SHAN   

  1. Shanghai Institute of Organic Chemistry, Academia Sinica
  • Received:1981-01-12 Published:2013-06-03

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16,17α-环氧-5α-和5β-孕甾-3β-醇-20-酮(1,2)用诺卡氏菌脱氢分别得到4,5,6,7和8,5,6,7四个化合物,其中16,17α-环氧-⊿4-孕甾烯-3,20-双酮(5)是主要产物.1和2分别用节杆菌脱氢时则均得到两个20α-羟基的不饱和化合物15和16,其中⊿1,4-双酮16是主要产物.16,17α-环氧-16β-甲基-5α-⊿9(11)-孕甾烯-3β-醇-20-酮(3)用诺卡氏菌脱氢可得到12,13,14三个化合物,其中16,17α-环氧-16β-甲基-⊿4,9(11)-孕甾二烯-3,20-双酮(13)是主要产物.综上所述,5α和5β甾族化合物用诺卡氏菌脱氢主要脱去C4,5两个氢原子形成⊿4-烯-3-酮化合物,而采用节杆菌可使Cl,2和C4,5位同时脱氢形成⊿1,4-双烯-3-酮化合物.

Incubation of 16, 17α-oxido-5α and 5β-pregnane-3β-ol-zo-one (1 and 2) with Nocardia sp.afforded four compounds (4, 6, 8, 7 and 8, 6, 6, 7)respectively, among which 16,17α-oxido-⊿4-pregnene-3, 20-dione (6) was the major product, while separate incubation of 1 and 2 with Arthrobdctor simplex both afforded only two unsatureted compounds (16 and 16)having 20-hydroxy group, in which 16, 17α-oxido-⊿1,4-pregnadiene-20α-ol-3, 20-dione (16) was the major product.Incubation of 16, 17α-oxido-16β-methyl-5α-⊿9(11)-pregnane-3,8-01-20-one (8) with Nocardid sp.gave three oompounds(12,18,14),in which 16, 17α-oxido-16β-methyl-⊿4,9(11)-pregnadiene-3, 20-dione (18) was the major product.It seemed that 5α and 5β steroids were mainly dehydrogenated at C4,5 by Nocardia sp.and at C1,2 and C4,5 by Arthrobactor simplex.