棘孢木霉对 20(S)-原人参二醇的生物转化。
Biotransformation of 20(S)-protopanaxadiol by Mucor spinosus.
机构信息
Division of Pharmacognostical Biotechnology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
出版信息
Phytochemistry. 2009 Jul-Aug;70(11-12):1416-20. doi: 10.1016/j.phytochem.2009.07.041. Epub 2009 Sep 3.
Biotransformation of 20(S)-protopanaxadiol (1) by the fungus Mucor spinosus AS 3.3450 yielded eight metabolites (2-9). On the basis of NMR and MS analyses, the metabolites were identified as 12-oxo-15alpha,27-dihydroxyl-20(S)-protopanaxadiol (2), 12-oxo-7beta,11alpha,28-trihydroxyl-20(S)-protopanaxadiol (3), 12-oxo-7beta,28-dihydroxyl-20(S)-protopanaxadiol (4), 12-oxo-15alpha,29-dihydroxyl-20(S)-protopanaxadiol (5), 12-oxo-7beta,15alpha-dihydroxyl-20(S)-protopanaxadiol (6), 12-oxo-7beta,11beta-dihydroxyl-20(S)-protopanaxadiol (7), 12-oxo-15alpha-hydroxyl-20(S)-protopanaxadiol (8), and 12-oxo-7beta-hydroxyl-20(S)-protopanaxadiol (9), respectively. Among them, 2-5, 7, and 8 are new compounds. These results indicated that M. spinosus could catalyze the specific C-12 dehydrogenation of 20(S)-protopanaxadiol, as well hydroxylation at different positions. These biocatalytic reactions may be difficult for chemical synthesis. The biotransformed products showed weak in vitro cytotoxic activities.
真菌棘孢木霉 AS 3.3450 生物转化 20(S)-原人参二醇（1）生成了 8 种代谢产物（2-9）。基于 NMR 和 MS 分析，鉴定这些代谢产物为 12-酮-15α，27-二羟基-20(S)-原人参二醇（2）、12-酮-7β，11α，28-三羟基-20(S)-原人参二醇（3）、12-酮-7β，28-二羟基-20(S)-原人参二醇（4）、12-酮-15α，29-二羟基-20(S)-原人参二醇（5）、12-酮-7β，15α-二羟基-20(S)-原人参二醇（6）、12-酮-7β，11β-二羟基-20(S)-原人参二醇（7）、12-酮-15α-羟基-20(S)-原人参二醇（8）和 12-酮-7β-羟基-20(S)-原人参二醇（9）。其中 2-5、7 和 8 是新化合物。这些结果表明棘孢木霉能够特异性地催化 20(S)-原人参二醇的 C-12 脱氢以及不同位置的羟化反应。这些生物催化反应可能难以通过化学合成实现。生物转化产物显示出较弱的体外细胞毒性活性。
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