Hitoyol A and B, Two Norsesquiterpenoids from the Basidiomycete Coprinopsis cinerea

Junnosuke Otaka, Daisuke Hashizume, Yui Masumoto, Atsuya Muranaka, Masanobu Uchiyama, Hiroyuki Koshino, Yushi Futamura, Hiroyuki Osada*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

Hitoyol A (1), an unprecedented norsesquiterpenoid with an exo-tricyclo[5.2.1.02,6]decane skeleton, was isolated from the culture broth of Basidiomycete Coprinopsis cinerea along with a novel skeletal hitoyol B (2) containing 4-cyclopentene-1,3-dione. Their structures and absolute configurations were analyzed by single-crystal X-ray diffraction and electronic circular dichroism spectroscopic methods. Compound 1 is possibly biosynthesized through decarboxylation-induced cyclization of lagopodin B, a known cuparene-type sesquiterpenoid. Compound 2 showed weak antimalarial activity with an IC50 of 59 μM.

Original languageEnglish
Pages (from-to)4030-4033
Number of pages4
JournalOrganic Letters
Volume19
Issue number15
DOIs
Publication statusPublished - 2017 Aug 4
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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