Isolation and absolute stereochemistry of coussaric acid, a new bioactive triterpenoid from the stems of Coussarea brevicaulis.

Abstract

Coussaric acid (1), a triterpenoid based on an ursane skeleton, and an oleanane-type triterpene acid, 3-epi-spathodic acid (2), as well as four known compounds, barbinervic acid, scutellaric acid, stigmasterol and stigmasterol glucoside, have been isolated from an EtOAc-soluble extract of the stems of Coussarea brevicaulis. The structures of compounds 1 and 2 were elucidated on the basis of spectroscopic investigation, and single-crystal X-ray crystallography was used to confirm the structure of 1. The absolute stereochemistry of 1 was established by chemical transformations and by the Mosher ester procedure. The potential of the isolates and chemical transformation products to induce quinone reductase was evaluated in mouse Hepa lclc7 hepatoma cells.

• Authors: Bao-Ning Su, Young-Hwa Kang, Rosa Elena Pinos, Bernard D Santarsiero, Andrew D Mesecar, D Doel Soejarto, Harry H S Fong, John M Pezzuto, A Douglas Kinghorn
• Journal: Phytochemistry (Phytochemistry) Vol. 64 Issue 1 Pg. 293-302 (Sep 2003) ISSN: 0031-9422 [Print] England
• PMID: 12946428 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Antineoplastic Agents, Phytogenic
• Triterpenes
• NAD(P)H Dehydrogenase (Quinone)

Topics

• Animals
• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Crystallography, X-Ray
• Drug Screening Assays, Antitumor
• Enzyme Induction (drug effects)
• Liver Neoplasms, Experimental
• Mice
• Models, Molecular
• Molecular Structure
• NAD(P)H Dehydrogenase (Quinone) (metabolism)
• Nuclear Magnetic Resonance, Biomolecular
• Plant Stems (chemistry)
• Plants, Medicinal (chemistry)
• Rubiaceae (chemistry)
• Stereoisomerism
• Triterpenes (chemistry, isolation & purification, pharmacology)
• Tumor Cells, Cultured