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Planta Med 2007; 73(15): 1581-1587
DOI: 10.1055/s-2007-993756
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Novel ent-Beyeran-19-oic Acids from Biotransformations of Isosteviol Metabolites by Mortierella isabellina

Che-Ling Lin1 , 2 , Shwu-Jiuan Lin2 , Wei-Jan Huang3 , 5 , Yuan-Ling Ku4 , Tung-Hu Tsai1 , Feng-Lin Hsu2 , 5
  • 1Institute of Traditional Medicine, National Yang-Ming University, Taipei, Taiwan
  • 2School and Graduate Institute of Pharmacy, College of Pharmacy, Taipei Medical University, Taipei, Taiwan
  • 3Chia-Yi School, Chang Gung Institute of Technology, Chiayi, Taiwan
  • 4Medical and Pharmaceutical Industry Technology and Development Center, Taipei, Taiwan
  • 5Graduate Institute of Pharmacognosy, College of Pharmacy, Taipei Medical University, Taipei, Taiwan
Further Information

Publication History

Received: April 4, 2007 Revised: October 11, 2007

Accepted: October 21, 2007

Publication Date:
13 December 2007 (online)

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Abstract

Biotransformations of ent-16β-hydroxybeyeran-19-oic acid (1) by Mortierella isabellina produced hydroxylated metabolites. The isolated metabolites included three new compounds, ent-14β,16β-dihydroxybeyeran-19-oic acid (3), ent-12β-hydroxy-16-oxobeyeran-19-oic acid (4), and ent-7α,12β-dihydroxy-16-oxobeyeran-19-oic acid (5), and one known compound, ent-7α,16β-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 7β-, 12α-, and 14α-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.

Key words

ent-16β-Hydroxybeyeran-19-oic acid - Mortierella isabellina - microbial biotransformations - hydroxylation - stevioside - isoteviol - MTT formazan exocytosis

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Prof. Dr. Feng-Lin Hsu

Graduate Institute of Pharmacognosy

College of Pharmacy

Taipei Medical University

250 Wu-Xin Street

Taipei City

Taipei 110

Taiwan

Republic of China

Phone: +886-2-8733-1139

Fax: +886-2-27370903

Email: hsu0320@tmu.edu.tw