title: Microbial metabolism of methyl protodioscin by Aspergillus niger culture--a new androstenedione producing way from steroid.
abstract: Methyl protodioscin (1), a natural furostanol biglycoside steroid, was a preclinical anticancer drug, which showed potent activity against most cell lines from leukemia and solid tumors in the National Cancer Institute's (NCI) human cancer panel. Metabolism of methyl protodioscin by Aspergillus niger was investigated. Seven metabolites were isolated and identified. Two main metabolites were pregnane glycosides and four were furostanol glycosides, together with the aglycone. It was found that steroidal saponin skeleton could be converted to pregnenolone skeleton only using microbial methods, which must have chemical procedures in the reported literatures. The proposed biosynthetic pathways of the microbial conversion products of methyl protodioscin were drawn. The found enriched the reaction types of microbial bioconversion and provided a new producing way of androstenedione from steroid. Most metabolites showed strong cytotoxic activities against HepG2, NCI-H460, HeLa, and MCF-7 cell lines.
authors.affiliation: Institute of Traditional Chinese Medicine & Natural Products, Jinan University, Guangzhou 510632, China. xh35@cornell.edu
authors.forename: Xiangjiu
authors.initials: X
authors.lastname: He
authors.forename: Bo
authors.initials: B
authors.lastname: Liu
authors.forename: Guanghui
authors.initials: G
authors.lastname: Wang
authors.forename: Xinluan
authors.initials: X
authors.lastname: Wang
authors.forename: Lina
authors.initials: L
authors.lastname: Su
authors.forename: Gexia
authors.initials: G
authors.lastname: Qu
authors.forename: Xinsheng
authors.initials: X
authors.lastname: Yao
mesh_terms: D000230:Adenocarcinoma / Q000188:drug therapy; D000735:Androstenedione / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D001234:Aspergillus niger / Q000235:genetics / Q000378:metabolism*; D001711:Biotransformation; D001943:Breast Neoplasms / Q000188:drug therapy; D002277:Carcinoma / Q000188:drug therapy; D006528:Carcinoma, Hepatocellular / Q000188:drug therapy; D002289:Carcinoma, Non-Small-Cell Lung / Q000188:drug therapy; D045744:Cell Line, Tumor; D004144:Diosgenin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity; D004305:Dose-Response Relationship, Drug; D005260:Female; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008113:Liver Neoplasms / Q000188:drug therapy; D008175:Lung Neoplasms / Q000188:drug therapy; D015394:Molecular Structure; D012503:Saponins / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D013256:Steroids / Q000378:metabolism*; D002583:Uterine Cervical Neoplasms / Q000188:drug therapy
chemical_list: D012503:Saponins; D013256:Steroids; C425324:methyl protodioscin; D000735:Androstenedione; D004144:Diosgenin