New steroidal glycosides from the rhizome of Anemarrhena asphodeloides

J Asian Nat Prod Res. 2014;16(9):901-9. doi: 10.1080/10286020.2014.942658. Epub 2014 Sep 16.

Abstract

Two new steroidal saponins, timosaponin X (1) and timosaponin Y (2), and one new pregnane glycoside, timopregnane B (3), were isolated from the rhizomes of Anemarrhena asphodeloides, as well as three known compounds 25S-timosaponin BII (4), protodesgalactotigonin (5), and timosaponin BII-a (6) isolated from this plant for the first time. By the detailed analysis of 1D, 2D NMR, MS spectra, and chemical evidences, the structures of new compounds were elucidated as 26-O-β-d-glucopyranosyl-(25S)-5β-22-methoxy-furost-3β,26-diol 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranoside (1), 5β-pseudo-spirost-3β,15α,23α-triol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (2), (5β,17α)-Δ((16)(17))-20-one-pregn-2β,3β-diol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (3).

Keywords: Anemarrhena asphodeloides; NMR; pregnane glycoside; steroidal saponin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anemarrhena / chemistry*
  • Drugs, Chinese Herbal / chemistry
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pregnanes / chemistry
  • Pregnanes / isolation & purification*
  • Rhizome / chemistry
  • Saponins / chemistry
  • Saponins / isolation & purification*
  • Steroids / chemistry
  • Steroids / isolation & purification*

Substances

  • Drugs, Chinese Herbal
  • Glycosides
  • Pregnanes
  • Saponins
  • Steroids
  • pregnane glycoside
  • timopregnane B
  • timosaponin B-II
  • timosaponin Y