Acacienone, a terpenoid-like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves

Yasumasa Hara, Yuichi Totsugi, Hiroshi Ichikawa, Shinji Harada, Kazuki Fujii, Firoj Ahmed, Samir K. Sadhu, Midori A. Arai, Masami Ishibashi

Research output: Contribution to journalArticlepeer-review

Abstract

A novel C20 natural product, acacienone (1), was isolated from the leaves of Acacia mangium collected in Bangladesh. The structure of compound 1 was elucidated by spectral studies and X-ray crystallographic analysis. Acacienone (1) possesses a terpenoid-related tetracyclic framework containing 20 carbons with biogenetically unusual structural features: (i) vicinal C1-branches at the C-3 and C-4 positions in the A ring, and (ii) a cyclopentenone D ring in an androsterone-like assembly, lacking a methyl group at the C-13 position.

Original languageEnglish
Pages (from-to)99-104
Number of pages6
JournalJournal of Natural Medicines
Volume75
Issue number1
DOIs
Publication statusPublished - 2021 Jan

Keywords

  • Acacia mangium
  • Androsterone-like cyclopentenone moiety
  • Bangladesh plant
  • Terpenoid-like C20 natural product

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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