Synthesis of ginsenoside Rg3, a minor constituent of Ginseng radix

V P Anufriev; G V Malinovskaya; V A Denisenko; N I Uvaròva; G B Elyakov; S I Kim; N I Baek

doi:10.1016/s0008-6215(97)00217-6

Synthesis of ginsenoside Rg3, a minor constituent of Ginseng radix

Carbohydr Res. 1997 Nov 10;304(2):179-82. doi: 10.1016/s0008-6215(97)00217-6.

Authors

V P Anufriev¹, G V Malinovskaya, V A Denisenko, N I Uvaròva, G B Elyakov, S I Kim, N I Baek

Affiliation

¹ Laboratory of Organic Synthesis of Natural Products, Pacific Institute of Bioorganic Chemistry, Far East Division, Russian Academy of Sciences, Vladivostok.

PMID: 9527441
DOI: 10.1016/s0008-6215(97)00217-6

Abstract

Glycosylation of 12beta-acetoxy-dammar-24-en-3beta,20(S)-diol (4), with hepta-O-acetyl-alpha-sophorosyl bromide (5) under catalysis by Ag2CO3 or Ag2O afforded a chromatographically unseparated mixture of the alpha- and beta-linked octaacetates 6 and 7 in an approximately 2.5:1 ratio. After deprotection and chromatographic purification, the free alpha- (8) and beta-glycosides (9) were obtained. Sophoroside 9 was identical in all respects with ginsenoside Rg3, the minor component of Ginseng Radix rubra. All compounds were fully characterized by 1H and 13C NMR spectroscopy.

MeSH terms

Acetylation
Ginsenosides*
Glycosylation
Magnetic Resonance Spectroscopy
Molecular Structure
Panax / chemistry*
Plants, Medicinal*
Saponins / chemical synthesis*
Saponins / chemistry
Saponins / isolation & purification

Substances

Ginsenosides
Saponins
ginsenoside Rg3