Bioactive Steroids with Methyl Ester Group in the Side Chain from a Reef Soft Coral Sinularia brassica Cultured in a Tank

Mar Drugs. 2017 Sep 1;15(9):280. doi: 10.3390/md15090280.

Abstract

A continuing chemical investigation of the ethyl acetate (EtOAc) extract of a reef soft coral Sinularia brassica, which was cultured in a tank, afforded four new steroids with methyl ester groups, sinubrasones A-D (1-4) for the first time. In particular, 1 possesses a β-D-xylopyranose. The structures of the new compounds were elucidated on the basis of spectroscopic analyses. The cytotoxicities of compounds 1-4 against the proliferation of a limited panel of cancer cell lines were assayed. The anti-inflammatory activities of these new compounds 1-4 were also evaluated by measuring their ability to suppress superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced human neutrophils. Compounds 2 and 3 were shown to exhibit significant cytotoxicity, and compounds 3 and 4 were also found to display attracting anti-inflammatory activities.

Keywords: Sinularia brassica; anti-inflammatory activity; cytotoxic activity; soft coral; steroid.

MeSH terms

  • Acetates / chemistry
  • Animals
  • Anthozoa / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Humans
  • N-Formylmethionine Leucyl-Phenylalanine / chemistry
  • Neutrophils / drug effects
  • Pancreatic Elastase / drug effects
  • Steroids* / chemistry
  • Steroids* / isolation & purification
  • Steroids* / pharmacology
  • Superoxides / metabolism
  • Xylose / analogs & derivatives
  • Xylose / chemistry

Substances

  • Acetates
  • Anti-Inflammatory Agents, Non-Steroidal
  • Steroids
  • xylopyranose
  • Superoxides
  • N-Formylmethionine Leucyl-Phenylalanine
  • ethyl acetate
  • Xylose
  • Pancreatic Elastase