Steroids glycosylated with both D- and L-arabinoses from the South China Sea gorgonian Dichotella gemmacea

J Nat Prod. 2013 Apr 26;76(4):764-8. doi: 10.1021/np300906b. Epub 2013 Mar 11.

Abstract

Three new 19-hydroxy steroidal glycosides, namely, junceellosides E-G (2-4), were isolated together with the known analogue junceelloside C (1) from the South China Sea gorgonian Dichotella gemmacea. The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. These glycosides are found to have sugar moieties of both β-l- and β-d-arabinopyranoses by HPLC analysis of their thiocarbamoyl-thiazolidine derivatives and those of authentic d- and l-arabinoses, leading to the structure revision of junceelloside C (1). This is the first report of steroidal glycosides from the gorgonian D. gemmacea and the first report of glycosides with β-l-arabinopyranose from marine sources.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Arabinose / chemistry
  • Arabinose / isolation & purification*
  • Arabinose / pharmacology
  • Drug Screening Assays, Antitumor
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Glycosylation
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oceans and Seas
  • Stereoisomerism
  • Steroids / chemistry
  • Steroids / isolation & purification*
  • Steroids / pharmacology

Substances

  • Antineoplastic Agents
  • Glycosides
  • Steroids
  • junceelloside C
  • Arabinose