Histone deacetylase inhibitor induced the production of three novel prenylated tryptophan analogs in the entomopathogenic fungus, Torrubiella luteorostrata

Teigo Asai, Takashi Yamamoto, Yoshiteru Oshima

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)

Abstract

Suberoyl bis-hydroxamic acid (SBHA), a histone deacetylase (HDAC) inhibitor, led to significant changes in the secondary metabolism of an entomopathogenic fungus, Torrubiella luteorostrata, and induced the production of three new prenylated tryptophan analogs, luteorides A-C (1-3). The structures are characterized by the presence of an (E)-oxime group, which is an unusual functional group in natural products, and a 3-methylbuta-1,3-dienyl unit as a common substituent. The method of culturing entomopathogenic fungi in the presence of HDAC inhibitors, such as SBHA, is convenient and attractive for obtaining novel secondary metabolites.

Original languageEnglish
Pages (from-to)7042-7045
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number52
DOIs
Publication statusPublished - 2011 Dec 28

Keywords

  • Entomopathogenic fungi
  • Epigenetics
  • Histone deacetylase inhibitor
  • Secondary metabolites
  • Tryptophan analogs

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Histone deacetylase inhibitor induced the production of three novel prenylated tryptophan analogs in the entomopathogenic fungus, Torrubiella luteorostrata'. Together they form a unique fingerprint.

Cite this