Dihydrobenzofurans as cannabinoid receptor ligands from Cordyceps annullata, an entomopathogenic fungus cultivated in the presence of an HDAC inhibitor

Teigo Asai, Dan Luo, Yutaro Obara, Tohru Taniguchi, Kenji Monde, Kouwa Yamashita, Yoshiteru Oshima

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

The secondary metabolite production of Cordyceps annullata, an entomopathogenic fungus, was clearly enhanced by the addition of suberoyl bis-hydroxamic acid (SBHA), a histone deacetylase (HDAC) inhibitor, to the culture medium. Four new 2,3-dihydrobenzofurans, annullatins A-D (1-4), and a new aromatic polyketide, annullatin E (5) were isolated from the culture medium, and the structures, including the absolute stereochemistries, were determined by spectroscopic analysis, vibrational circular dichroism (VCD), and chemical transformations. Annullatin A (1) exhibited potent agonistic activity toward the cannabinoid receptors CB1 and CB2. Annullatin B (2) and D (4) displayed CB1 agonistic activity and CB2 inverse agonistic activity.

Original languageEnglish
Pages (from-to)2239-2243
Number of pages5
JournalTetrahedron Letters
Volume53
Issue number17
DOIs
Publication statusPublished - 2012 Apr 25

Keywords

  • Cannabinoid receptor
  • Entomopathogenic fungi
  • HDAC inhibitor
  • Secondary metabolites
  • VCD

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Dihydrobenzofurans as cannabinoid receptor ligands from Cordyceps annullata, an entomopathogenic fungus cultivated in the presence of an HDAC inhibitor'. Together they form a unique fingerprint.

Cite this