(9βH)-Pimaranes and Derivatives from the Tuber of Icacina trichantha

J Nat Prod. 2015 Nov 25;78(11):2731-7. doi: 10.1021/acs.jnatprod.5b00688. Epub 2015 Nov 2.

Abstract

New 17-nor-pimaranes (1, 2), (9βH)-pimaranes (3, 4), and 17-nor-(9βH)-pimarane (5) were isolated from the tuber of Icacina trichantha. The structures were elucidated based on spectroscopic and HRMS data. The absolute configurations of 3 and 5 were determined by single-crystal X-ray diffraction. Compound 5 possesses a unique 19,20-δ-lactone moiety. Compound 3 showed cytotoxicity against MDA-MB-435 (human melanoma cancer) cells with an IC50 value of 7.04 μM. A plausible biogenetic pathway for compounds 1-5 is proposed.

Publication types

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

MeSH terms

  • Abietanes / chemistry
  • Abietanes / isolation & purification*
  • Crystallography, X-Ray
  • Humans
  • Magnoliopsida / chemistry*
  • Molecular Structure
  • Nigeria
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Tubers / chemistry

Substances

  • 14alpha-methoxyhumirianthol
  • Abietanes
  • pimarane