Kalparinol, a Salvialane (Isodaucane) Sesquiterpenoid Derived from Native Australian Dysphania Species That Suggests a Putative Biogenetic Link to Zerumbone

J Nat Prod. 2020 May 22;83(5):1473-1479. doi: 10.1021/acs.jnatprod.9b01039. Epub 2020 Apr 17.

Abstract

Dysphania is a genus of plants endemic to the Australian continent, occurring primarily in arid and temperate zones. Despite their prevalence, very little in the way of phytochemical and/or bioactivity investigation of native Dysphania has been performed. Herein reported is the isolation and elucidation of (6E,9E)-zerumbone epoxide and a hitherto unreported isomer, (6Z,9E)-zerumbone epoxide, from D. kalpari. In addition, a novel isodaucane sesquiterepene, kalparinol, was isolated from both D. kalpari and D. rhadinostachya. The coisolation of the humulene and isodaucane skeletons, combined with the lack of any cadalane systems, could suggest an alternate novel biogenetic pathway originating from zerumbone, which is unlike any other proposals for the isodaucene system.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amaranthaceae / chemistry*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Australia
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Fungi / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Plant Extracts / chemistry
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / metabolism
  • Sesquiterpenes / pharmacology*
  • X-Ray Diffraction

Substances

  • Antifungal Agents
  • Antineoplastic Agents, Phytogenic
  • Plant Extracts
  • Sesquiterpenes
  • isodaucene
  • zerumbone