Kadcoccinones A-F, New Biogenetically Related Lanostane-Type Triterpenoids with Diverse Skeletons from Kadsura coccinea

Org Lett. 2015 Sep 18;17(18):4616-9. doi: 10.1021/acs.orglett.5b02360. Epub 2015 Sep 8.

Abstract

Six new lanostane-related triterpenoids, kadcoccinones A-F (1-6), were isolated from Kadsura coccinea. Compound 3 possesses a novel 6/6/9-fused carbocyclic core containing a rare oxabicyclo[4.3.1]decane system. Compounds 4 and 5 are isomers representing the first example of the 18(13 → 12)-abeo-26-norlanostane triterpenoid. The absolute configurations of 1 and 4-6 were defined by X-ray diffraction and experimental ECD spectra, and that of 3 was elucidated by quantum chemical calculations. The plausible biogenetic pathway of 1-6 is postulated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Kadsura / chemistry*
  • Lanosterol* / analogs & derivatives
  • Lanosterol* / chemistry
  • Lanosterol* / isolation & purification
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Structure-Activity Relationship

Substances

  • Lanosterol