Novel ent-Beyeran-19-oic acids from biotransformations of isosteviol metabolites by Mortierella isabellina.
Biotransformations of ENT-16beta-hydroxybeyeran-19-oic acid ( 1) by Mortierella isabellina produced hydroxylated metabolites. The isolated metabolites included three new compounds, ent-14beta,16beta-dihydroxybeyeran-19-oic acid ( 3), ent-12beta-hydroxy-16-oxobeyeran-19-oic acid ( 4), and ent-7alpha,12beta-dihydroxy-16-oxobeyeran-19-oic acid ( 5), and one known compound, ent-7alpha,16beta-dihydroxybeyeran-19-oic acid ( 2). The structural elucidation was achieved by detailed analysis of LC-MS chromatograms, and MS and NMR spectroscopic data. In this study, M. isabellina hydroxylated the basic skeleton beyeran-19-oic acid at the 7beta-, 12alpha-, and 14alpha-positions, and oxidized the skeleton at the 16-position. All compounds were evaluated with the cell viability assay. The results of the bioassay indicated that MTT formazan exocytosis occurs upon treatment of the cells with 1.
Lin
Che-Ling
CL
Institute of Traditional Medicine, National Yang-Ming University, Taipei, Taiwan.
Lin
Shwu-Jiuan
SJ
Huang
Wei-Jan
WJ
Ku
Yuan-Ling
YL
Tsai
Tung-Hu
TH
Hsu
Feng-Lin
FL
D000363:Agaricales / Q000378:metabolism*; D000972:Antineoplastic Agents, Phytogenic / Q000008:administration & dosage / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology / Q000627:therapeutic use; D001711:Biotransformation; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D002853:Chromatography, Liquid; D004224:Diterpenes / Q000493:pharmacokinetics*; D045786:Diterpenes, Kaurane / Q000008:administration & dosage / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology / Q000627:therapeutic use; D005960:Glucosides / Q000008:administration & dosage / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology / Q000627:therapeutic use; D006801:Humans; D013058:Mass Spectrometry
D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D045786:Diterpenes, Kaurane; D005960:Glucosides; C458719:beyerenoic acid; C012043:stevioside