Biotransformation of dihydroisosteviol and the effects of transformed products on steroidogenic gene expressions

Shwu Fen Chang, Li Ming Yang, Tsurng Juhn Huang, Chin Yang Chen, Shiow Yunn Sheu, Pan Chun Liu, Shwu Jiuan Lin

Research output: Contribution to journalArticle

Abstract

The biotransformation of dihydroisosteviol with Absidia pseudocylindrospora ATCC 24169, Streptomyces griseus ATCC 10137, Mucor recurvatus MR36, and Aspergillus niger BCRC 31130 yielded 15 metabolites, eight of which were previously unknown. Structures of metabolites were established by 2D NMR techniques and HRMS data, two of which were further corroborated by chemical means, and another via single-crystal X-ray diffraction analysis. Subsequently, two steroidogenic cell lines (Y-1 mouse adrenal tumor and MA-10 mouse Leydig tumor cells) were used in a reverse transcription-PCR analysis to assess the effects of all compounds on steroidogenic gene expressions using forskolin as a positive control. The tested gene expressions included steroidogenic factor-1 (SF-1), steroidogenic acute regulatory protein (StAR), and cytochrome P450 side-chain cleavage (P450scc) enzyme. Gene expression profiles showed that ten of the tested compounds effectively suppressed P450SCC mRNA expression in both Y-1 and MA-10 cells. Several induced SF-1 gene expression and two enhanced StAR gene expression in Y-1 cells. By contrast, in MA-10 cells, one compound effectively suppressed StAR mRNA expression, whereas for others effectively suppressed SF-1 gene expression. The results suggest that analogs of dihydroisosteviol can be potential modulators to alter steroidogenic gene expressions and subsequent enzyme activities.

Original languageEnglish
Pages (from-to)268-276
Number of pages9
JournalPhytochemistry
Volume95
DOIs
Publication statusPublished - Nov 2013

Fingerprint

Biotransformation
biotransformation
Gene expression
Steroidogenic Factor 1
Gene Expression
gene expression
regulatory proteins
Metabolites
Absidia
Tumors
Streptomyces griseus
Leydig Cell Tumor
Mucor
Cells
Messenger RNA
Glandular and Epithelial Neoplasms
metabolites
Aspergillus niger
Colforsin
Enzymes

Keywords

  • Biotransformation
  • Dihydroisosteviol
  • Steroidogenic genes

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Horticulture

Cite this

Biotransformation of dihydroisosteviol and the effects of transformed products on steroidogenic gene expressions. / Chang, Shwu Fen; Yang, Li Ming; Huang, Tsurng Juhn; Chen, Chin Yang; Sheu, Shiow Yunn; Liu, Pan Chun; Lin, Shwu Jiuan.

In: Phytochemistry, Vol. 95, 11.2013, p. 268-276.

Research output: Contribution to journalArticle

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