Isolation of Sesquiterpenoids and Steroids from the Soft Coral Sinularia brassica and Determination of Their Absolute Configuration

Mar Drugs. 2021 Sep 17;19(9):523. doi: 10.3390/md19090523.

Abstract

Two undescribed rearranged cadinane-type sesquiterpenoids (1-2), named sinulaketol A-B, together with one new chlorinated steroid (3), one new gorgosterol (4), one known sesquiterpene (5), one known dibromoditerpene (6) and two known polyhydroxylated steroids (7-8) were isolated from the soft coral Sinularia brassica. The structures of these compounds were established by extensive spectroscopic analysis, including HRESIMS, 1D, and 2D NMR spectroscopy. Their absolute configurations were also determined by the ECD calculations and DP4+ probability analysis. Antileishmanial activity of compounds 1-8 was evaluated in vitro against the amastigote forms of Leishmania donovani, in which compounds 3, 6, and 7 inhibited the growth of L. donovani by 58.7, 74.3, 54.7%, respectively, at a concentration of 50 μM. Antimicrobial effect of the isolated compounds were also evaluated against Candida albicans, Staphylococcus aureus, and Escherichia coli. Compound 6, a brominated diterpene, exhibited antimicrobial effect against S. aureus.

Keywords: Sinularia brassica; antileishmanial activity; antimicrobial activity; sesquiterpenoids; steroids.

MeSH terms

  • Animals
  • Anthozoa*
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Antiprotozoal Agents / chemistry*
  • Antiprotozoal Agents / pharmacology
  • Candida albicans / drug effects
  • Escherichia coli / drug effects
  • Leishmania donovani / drug effects
  • Magnetic Resonance Spectroscopy
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / pharmacology
  • Staphylococcus aureus / drug effects
  • Steroids / chemistry*
  • Steroids / pharmacology
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antiprotozoal Agents
  • Sesquiterpenes
  • Steroids