New spirostanol glycosides from Solanum nigrum and S. jasminoides

J Nat Med. 2012 Oct;66(4):658-63. doi: 10.1007/s11418-012-0637-z. Epub 2012 Mar 3.

Abstract

A new characteristic steroidal glycoside possessing a hydroxyl group at C-23, inunigroside A (1), was isolated from the withered berries of Solanum nigrum L. On the basis of spectroscopic analysis, the structure of 1 was characterized as (5α,22S,23S,25R)-3β,23-dihydroxyspirostane 3-O-β-lycotetraoside. Next, a major steroidal sapogenol, (22R, 25S)-3β,15α-dihydroxy-spirost-5-ene (3), was obtained from the acid hydrolysate of the methanolic extract of the aerial parts of Solanum jasminoides L. A new bisdesmoside, 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl (22R,25S)-3β,15α-dihydroxyspirost-5-ene 15-O-α-L-rhamnopyranoside (4), named jasminoside A, was isolated from the methanolic extract of S. jasminoides.

MeSH terms

  • Glycosides / chemistry*
  • Molecular Structure
  • Solanum / chemistry*
  • Solanum nigrum / chemistry*
  • Spirostans / chemistry*

Substances

  • Glycosides
  • Spirostans