A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra

Org Lett. 2005 Dec 8;7(25):5709-12. doi: 10.1021/ol052498l.

Abstract

[chemical reaction: see text]. Three new ent-trachylobane diterpenoids (1-3) were isolated and structures elucidated from Mitrephora glabra Scheff. (Annonaceae). Mitrephorone A (1) possesses a hexacyclic ring system with adjacent ketone moieties and an oxetane ring, both of which are unprecedented among trachylobanes. All compounds were evaluated for cytotoxicity against a panel of cancer cells, where 1 displayed the most potent and broadest activity, and against a battery of antimicrobial assays, where all compounds were approximately equipotent.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amphotericin B / pharmacology
  • Annonaceae / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Bacteria / drug effects
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Saccharomyces cerevisiae / drug effects
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Diterpenes
  • mitrephorone A
  • mitrephorone B
  • mitrephorone C
  • Amphotericin B