Tertiary structure of ginsenoside Re studied by NMR Spectroscopy

Abstract

Ginseng has long been used as a traditional medicine in Asian countries including Korea and China. In recent years, it has been reported that the biological activities of ginseng are due to its active components, ginsenosides. Ginsenosides are represented by triterpenes of the dammarane type. Ginsenoside Re consists of two glucose rings, one rhamnose ring, and the triterpene ring. In the present study ginsenoside Re has been isolated from the Korean ginseng (Panax ginseng) and the tertiary structure has been determined using NMR spectroscopy. Flexibilities around each linkages described by seven torsion angles were considered. The structures of ginsenoside Re obtained by NMR spectroscopy show the rigidity around the glucopyranosyl ring II and alkene side chain. The dihedral angles of 05, 06, 07 are about 150 degrees, 50 degrees and 45 degrees, respectively. In addition, flexibility exists around rhamnopyranosyl and glucopyronosyl moiety. The linkage around the rhamnopyranosyl and glucopyranosyl ring I, are divided into three groups. This flexibility seems to play important role in regulation of the hydrophobic surface exposed to the solvent. Because of the growing need for the structural determination of ginsenoside, this result can help to understand their well-accepted pharmacological effects of ginsenoside Re.