Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system

Chen Liang Zhao, Md Shahid Sarwar, Jiang Hai Ye, Chuen Fai KU, Wan Fei Li, Guo Yong Luo, Jing Jie Zhang, Jun Xu, Zhao Feng Huang, Siu Wai TSANG, Lu Tai Pan*, Hongjie ZHANG

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

We report the isolation of a novel diterpene, designated as `amethane', from Isodon amethystoides (Lamiaceae). The diterpene [amethinol A; systematic name: (4aR,4bR,7R,10aS)-4b,7-dihydroxy-7-isopropyl-1,1-dimethyl-9-oxododecahydrobenzo[a]azulene-4a(2H)-carboxylic acid], possesses a unique skeleton containing a six/five/seven-membered tricyclic system. Intermolecular O—H…O close contacts were found to the carboxyl, carbonyl and hydroxy groups, connecting molecules into a two-dimensional structure. A possible biosynthetic pathway has been proposed. In addition, the compound was evaluated for its biological activities against different disease targets, and was found to significantly attenuate RORγt-dependent autoimmune responses.

Original languageEnglish
Pages (from-to)635-640
Number of pages6
JournalActa crystallographica. Section C, Structural chemistry
Volume74
Issue number5
DOIs
Publication statusPublished - May 2018

Scopus Subject Areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

User-Defined Keywords

  • amethane diterpene
  • amethinol A
  • biosynthetic pathway
  • crystal structure
  • Isodon amethystoides
  • Lamiaceae
  • natural product
  • RORγt antagonist

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