Clerodane and labdane diterpenoids from Nuxia sphaerocephala

Phytochemistry. 2006 Mar;67(5):444-51. doi: 10.1016/j.phytochem.2005.11.024. Epub 2006 Jan 19.

Abstract

Seven diterpenoids including four clerodane and three labdane derivatives, (13S)-ent-7beta-hydroxy-3-cleroden-15-oic acid (1), ent-7beta-hydroxy-2-oxo-3-cleroden-15-oic acid (2), ent-2,7-dioxo-3-clero-den-15-oic acid (3), ent-18-(E)-caffeoyloxy-7beta-hydroxy-3-cleroden-15-oic acid (4) (13S)-ent-18-(E)-coumaroyloxy-8(17)-labden-15-oic acid (5), ent-18-(E)-caffeoyloxy-8(17)-labden-15-oic acid (6), ent-15-(E)-caffeoyloxy-8(17)-labden-18-oic acid (7), have been isolated from an ethyl acetate extract of the leaves of Nuxia sphaerocephala, together with 17 known compounds. 3-Oxolup-20(29)-en-30-al (3-oxolupenal) (8) and 3beta-hydroxylup-20(29)-en-30-al (3beta-hydroxy-lupenal) (9) showed the best inhibitory activity against Plasmodium falciparum with the IC(50) values between 1.55 and 4.67 microg/ml in vitro, respectively. The structure and the relative stereochemistry of the compounds were established on the basis of their spectroscopic properties. The absolute configuration at C-13 of 1 and 5 was determined by the PGME amide procedure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemistry*
  • Antimalarials / pharmacology*
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology
  • Diterpenes, Clerodane / chemistry*
  • Diterpenes, Clerodane / isolation & purification
  • Diterpenes, Clerodane / pharmacology
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology
  • Plasmodium falciparum / drug effects

Substances

  • Antimalarials
  • Diterpenes
  • Diterpenes, Clerodane
  • Plant Extracts