Mannolides A-C with an Intact Diterpenoid Skeleton Providing Insights on the Biosynthesis of Antitumor Cephalotaxus Troponoids

Org Lett. 2016 Apr 15;18(8):1880-3. doi: 10.1021/acs.orglett.6b00653. Epub 2016 Apr 4.

Abstract

Three new diterpenoids, mannolides A-C (1-3), and two new Cephalotaxus troponoids, 4 and 5, were isolated from Cephalotaxus mannii and structurally characterized by spectroscopic data and X-ray crystallography. The discovery of compounds 1-3 featuring a new intact carbon skeleton, proposed as cephalotane, sheds new light on the biogenesis of Cephalotaxus troponoids, a rare class of antitumor C19 norditerpenoids. Antitumor tests showed that the tropone motif is essential for the activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / biosynthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Cephalotaxus / chemistry*
  • Crystallography, X-Ray
  • Diterpenes / chemistry
  • Diterpenes / metabolism*
  • Diterpenes / pharmacology*
  • Drug Screening Assays, Antitumor
  • Molecular Structure

Substances

  • Antineoplastic Agents, Phytogenic
  • Diterpenes
  • mannolide A
  • mannolide B
  • mannolide C