Lamm Andrew S, Chen Avril R M, Reynolds William F, Reese Paul B
Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica.
Steroids. 2007 Sep;72(9-10):713-22. doi: 10.1016/j.steroids.2007.05.008. Epub 2007 Jun 7.
The fungi Whetzelinia sclerotiorum ATCC 18687, Phanerochaete chrysosporium ATCC 24725 and Mucor plumbeus ATCC 4740 were examined for their ability to perform steroid biotransformations under single phase, pulse feed conditions. The steroids 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone) (1), 17beta-hydroxyandrost-4-en-3-one (testosterone) (5), 3beta-hydroxypregn-5-en-20-one (pregnenolone) (3), pregn-4-ene-3,20-dione (progesterone) (9), 17alpha,21-dihydroxypregn-4-ene-3,11,20-trione (cortisone) (11), 17alpha,21-dihydroxypregna-1,4-diene-3,11,20-trione (prednisone) (14), and 3-hydroxyestra-1,3,5(10)-trien-17-one (estrone) (15) were fed to each fungus. The production of a number of novel metabolites is reported. Of the fungi investigated W. sclerotiorum performed the most interesting biotransformations and had a clear propensity for 2beta, 6beta/7beta and 15beta/16beta hydroxylations. P. chrysosporium was more prone functionalize steroids in the allylic position. Oxygen insertion at C-14 by M. plumbeus is reported for the first time. All three micro-organisms exhibited redox activity.
对真菌核盘菌属核盘菌ATCC 18687、黄孢原毛平革菌ATCC 24725和铅色毛霉ATCC 4740在单相脉冲进料条件下进行甾体生物转化的能力进行了研究。将甾体3β - 羟基雄甾 - 5 - 烯 - 17 - 酮（脱氢表雄酮）（1）、17β - 羟基雄甾 - 4 - 烯 - 3 - 酮（睾酮）（5）、3β - 羟基孕甾 - 5 - 烯 - 20 - 酮（孕烯醇酮）（3）、孕甾 - 4 - 烯 - 3,20 - 二酮（孕酮）（9）、17α,21 - 二羟基孕甾 - 4 - 烯 - 3,11,20 - 三酮（可的松）（11）、17α,21 - 二羟基孕甾 - 1,4 - 二烯 - 3,11,20 - 三酮（泼尼松）（14）和3 - 羟基雌甾 - 1,3,5(10) - 三烯 - 17 - 酮（雌酮）（15）分别投喂给每种真菌。报道了多种新代谢产物的产生。在所研究的真菌中，核盘菌属核盘菌进行了最有趣的生物转化，并且明显倾向于进行2β、6β/7β和15β/16β羟基化。黄孢原毛平革菌更倾向于在烯丙基位置使甾体官能化。首次报道了铅色毛霉在C - 14处的氧插入。所有三种微生物均表现出氧化还原活性。
