Fungal transformation of isosteviol lactone and its biological evaluation for inhibiting the AP-1 transcription factor

Bo Hon Chou, Li Ming Yang, Shwu Fen Chang, Feng Lin Hsu, Chia Hsin Lo, Wen Kuang Lin, Li Hsuan Wang, Pan Chun Liu, Shwu Jiuan Lin

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A number of hydroxylated diterpenoids were obtained from the microbial transformation of isosteviol lactone (4α-carboxy-13α-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone) (2) with Mucor recurvatus MR 36, Aspergillus niger BCRC 31130, and Absidia pseudocylindrospora ATCC 24169. Incubation of 2 with M. recurvatus and Asp. niger led to isolation of seven known compounds (1 and 3-8). Incubation of 2 with Abs. pseudocylindrospora produced 5 and six previously unreported compounds (9-14). The structures of these isolated compounds were deduced by high-field NMR techniques (1H, 13C, DEPT, COSY, NOESY, HSQC, and HMBC), and those of 9 and 11 were further confirmed by X-ray crystallographic analyses. Subsequently, the inhibitory effects on activator protein-1 (AP-1) activation in lipopolysaccharide-stimulated RAW 264.7 macrophages of all of these compounds were evaluated. Compounds 2-5, 8, 9, 11, and 12 exhibited significant inhibitory activity, while 3 was more potent than the reference compound of dexamethasone.

Original languageEnglish
Pages (from-to)759-764
Number of pages6
JournalPhytochemistry
Volume70
Issue number6
DOIs
Publication statusPublished - Apr 2009

Fingerprint

Aspergillus niger
Diterpenes
Macrophages
Aspergillus
Transcription Factor AP-1
Lactones
lactones
Dexamethasone
Lipopolysaccharides
Transcription Factors
Absidia
transcription factors
Chemical activation
Nuclear magnetic resonance
Mucor
X rays
Acids
dexamethasone
diterpenoids
lipopolysaccharides

Keywords

  • Activator protein-1
  • Diterpenoid
  • Isosteviol lactone
  • Microbial transformation

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Horticulture

Cite this

Fungal transformation of isosteviol lactone and its biological evaluation for inhibiting the AP-1 transcription factor. / Chou, Bo Hon; Yang, Li Ming; Chang, Shwu Fen; Hsu, Feng Lin; Lo, Chia Hsin; Lin, Wen Kuang; Wang, Li Hsuan; Liu, Pan Chun; Lin, Shwu Jiuan.

In: Phytochemistry, Vol. 70, No. 6, 04.2009, p. 759-764.

Research output: Contribution to journalArticle

Chou, Bo Hon ; Yang, Li Ming ; Chang, Shwu Fen ; Hsu, Feng Lin ; Lo, Chia Hsin ; Lin, Wen Kuang ; Wang, Li Hsuan ; Liu, Pan Chun ; Lin, Shwu Jiuan. / Fungal transformation of isosteviol lactone and its biological evaluation for inhibiting the AP-1 transcription factor. In: Phytochemistry. 2009 ; Vol. 70, No. 6. pp. 759-764.
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