Novel ent-beyeran-19-oic acids from biotransformations of isosteviol metabolites by Mortierella isabellina

Che Ling Lin, Shwu Jiuan Lin, Wei Jan Huang, Yuan Ling Ku, Tung Hu Tsai, Feng-Lin Hsu

Research output: Contribution to journalArticle

8 Citations (Scopus)

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 enr-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.

Original languageEnglish
Pages (from-to)1581-1587
Number of pages7
JournalPlanta Medica
Volume73
Issue number15
DOIs
Publication statusPublished - Dec 2007

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Mortierella
Biotransformation
Metabolites
biotransformation
metabolites
Acids
acids
Skeleton
skeleton
Cells
exocytosis
Bioassay
Exocytosis
Biological Assay
cell viability
isosteviol
isostevic acid
Assays
Cell Survival
bioassays

Keywords

  • ent-16β-Hydroxybeyeran-19-oic acid
  • Hydroxylation
  • Isoteviol
  • Microbial biotransformations
  • Mortierella isabellina
  • MTT formazan exocytosis
  • Stevioside

ASJC Scopus subject areas

  • Plant Science
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Novel ent-beyeran-19-oic acids from biotransformations of isosteviol metabolites by Mortierella isabellina. / Lin, Che Ling; Lin, Shwu Jiuan; Huang, Wei Jan; Ku, Yuan Ling; Tsai, Tung Hu; Hsu, Feng-Lin.

In: Planta Medica, Vol. 73, No. 15, 12.2007, p. 1581-1587.

Research output: Contribution to journalArticle

Lin, Che Ling ; Lin, Shwu Jiuan ; Huang, Wei Jan ; Ku, Yuan Ling ; Tsai, Tung Hu ; Hsu, Feng-Lin. / Novel ent-beyeran-19-oic acids from biotransformations of isosteviol metabolites by Mortierella isabellina. In: Planta Medica. 2007 ; Vol. 73, No. 15. pp. 1581-1587.
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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 enr-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.",
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