Lithocarpic Acids A-N, 3,4-seco-Cycloartane Derivatives from the Cupules of Lithocarpus polystachyus

J Nat Prod. 2014 Aug 22;77(8):1910-20. doi: 10.1021/np500379f.

Abstract

Fourteen new 3,4-seco-cycloartane-type triterpenes, lithocarpic acids A-N (1-14), together with one known compound, coccinetane E (15), were identified from the cupules of Lithocarpus polystachyus. The structures of 1-14 were determined by spectroscopic data analysis and chemical methods, and the absolute configurations of 1 and 4 were defined unequivocally by X-ray crystallography using Cu Kα radiation. Compounds 1-15 are the first examples of 3,4-seco-cycloartane derivatives isolated from the genus Lithocarpus. Among them, compounds 1 and 2, 9 and 10, and 11 and 12 were found to be three pairs of C-24 epimers, while compounds 7 and 8 represent the first examples of 3,4-seco-norcycloartane-type triterpenes. Compound 1, as the major component of the plant extract, showed potent antibacterial activity against Micrococcus luteus and Bacillus subtilis, with MIC values of 3.1 and 6.3 μg/mL, respectively, as well as inhibitory activity against human and mouse 11β-hydroxysteroid dehydrogenase type 1, with IC50 values of 1.9 and 0.24 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / antagonists & inhibitors*
  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Crystallography, X-Ray
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Fagaceae / chemistry*
  • Humans
  • Mice
  • Microbial Sensitivity Tests
  • Micrococcus luteus / drug effects
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Staphylococcus aureus / drug effects
  • Staphylococcus epidermidis / drug effects
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • Anti-Bacterial Agents
  • Drugs, Chinese Herbal
  • Triterpenes
  • cycloartane
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1