Yan J L, Lee S S, Wang K C
School of Pharmacy, College of Medicine, National Taiwan University, No. 1, Jen-Ai Road, Taipei 100, Republic of, Taiwan, China.
Steroids. 2000 Dec;65(12):863-70. doi: 10.1016/s0039-128x(00)00170-7.
Incubation of 3beta-hydroxy-5,6alpha-cyclopropano-5alpha-cholestane (4), 3beta-hydroxy-5,6beta-cyclopropano-5beta-cholestane (5), and 3beta-hydroxy-5,6alpha-cyclopropano-5alpha-cholest-7-e ne (6) with Mycobacterium sp. (NRRL B-3805) gave a mixture of side chain cleaved 17-keto steroids as the major products in 52, 57, and 69% yields, respectively. Among these 17-keto steroids, the cyclopropyl ring eliminated product, androst-4-ene-3,17-dione (9), was isolated in 6, 4, and 8% yields, respectively. A cyclopropyl ring migration product, 6alpha,7alpha-cyclopropanoandrost-4-ene-3,17-dione (16), was isolated from the incubation mixture of 6 in 4% yield, also 10% yield of 16 was obtained when 5, 6alpha-cyclopropano-5alpha-androst-7-ene-3,17-dione (12) was incubated. The cyclopropyl ring opening and subsequent reduction followed by oxidation of the two major biotransformation products, 5, 6beta-cyclopropano-5beta-androsta-3,17-dione (10) and 5, 6alpha-cyclopropano-5alpha-androsta-3,17-dione (7), gave 6beta- and 6alpha-methylandrost-4-ene-3,17-dione in 60, and 45% yields, respectively.
将3β-羟基-5,6α-环丙基-5α-胆甾烷（4）、3β-羟基-5,6β-环丙基-5β-胆甾烷（5）和3β-羟基-5,6α-环丙基-5α-胆甾-7-烯（6）与分枝杆菌属（NRRL B - 3805）一起培养，分别以52%、57%和69%的产率得到侧链裂解的17-酮甾体混合物作为主要产物。在这些17-酮甾体中，环丙基环消除产物雄甾-4-烯-3,17-二酮（9）的分离产率分别为6%、4%和8%。从6的培养混合物中以4%的产率分离得到环丙基环迁移产物6α,7α-环丙基雄甾-4-烯-3,17-二酮（16）；当5,6α-环丙基-5α-雄甾-7-烯-3,17-二酮（12）进行培养时，也以10%的产率得到16。两种主要生物转化产物5,6β-环丙基-5β-雄甾-3,17-二酮（10）和5,6α-环丙基-5α-雄甾-3,17-二酮（7）的环丙基环开环、随后还原并氧化，分别以60%和45%的产率得到6β-和6α-甲基雄甾-4-烯-3,17-二酮。
