Steroidal Saponins from the Rhizomes of Aspidistra typica

PLoS One. 2016 Mar 3;11(3):e0150595. doi: 10.1371/journal.pone.0150595. eCollection 2016.

Abstract

Eleven new furostanol saponins, typaspidosides B-L (1-11), one new spirostanol saponin, typaspidoside M (12), and five known spirostanol saponins, 25S-atropuroside (13), neoaspidistrin (14), (25S)-pratioside D1 (15), 25S-aspidistrin (16) and 25S-neosibiricoside (17) were isolated from the rhizomes of Aspidistra typica Baill. The structures of the new compounds were established using 1D and 2D NMR (1H-1H COSY, HMQC, HMBC and ROESY) spectroscopy, high resolution mass spectrometry, and chemical methods. The aglycones of 1-3 (unusual furostanol saponins with opened E ring type), 9 and 10 (the methoxyl substituent at C-23 position) were found, identified from natural products for the first time. Moreover, the anti-HIV activities of the isolated steroidal glycosides were assessed, and compounds 13, 14, 16 and 17 exhibited high active against HIV-1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / isolation & purification
  • Anti-HIV Agents / pharmacology*
  • Capsid Proteins / antagonists & inhibitors
  • Capsid Proteins / genetics
  • Capsid Proteins / metabolism
  • Gene Expression
  • Genes, Reporter
  • HEK293 Cells
  • HIV-1 / drug effects*
  • HIV-1 / genetics
  • HIV-1 / growth & development
  • Humans
  • Liliaceae / chemistry*
  • Luciferases / antagonists & inhibitors
  • Luciferases / genetics
  • Luciferases / metabolism
  • Magnetic Resonance Spectroscopy
  • Plant Extracts / chemistry
  • Reassortant Viruses / drug effects*
  • Reassortant Viruses / genetics
  • Reassortant Viruses / growth & development
  • Rhizome / chemistry*
  • Saponins / isolation & purification
  • Saponins / pharmacology*
  • Spirostans / isolation & purification
  • Spirostans / pharmacology
  • Steroids / isolation & purification
  • Steroids / pharmacology
  • Sterols / isolation & purification
  • Sterols / pharmacology*
  • Structure-Activity Relationship
  • Vesiculovirus / genetics
  • Virus Replication / drug effects

Substances

  • Anti-HIV Agents
  • Capsid Proteins
  • Plant Extracts
  • Saponins
  • Spirostans
  • Steroids
  • Sterols
  • furostanol saponin I
  • typaspidoside A
  • Luciferases

Grants and funding

This work was supported by the National Natural Science Foundation of China (no. 81373938) and National Infrastructure of Microbial Resources (No. NIMR-2015-3).