Three biscembranoids and their monomeric counterpart cembranoid, a biogenetic Diels-Alder precursor, from the soft coral Sarcophyton elegans

J Nat Prod. 2007 Dec;70(12):1951-4. doi: 10.1021/np070129n. Epub 2007 Nov 16.

Abstract

Two new cembranoids, methyl tetrahydrosarcoate ( 1) and methyl tetrahydroisosarcoate ( 2), were isolated from the soft coral Sarcophyton elegans, collected at Kitangambwe Kenya, together with four biscembranoids, the known nyalolide ( 3) and the unprecedented desacetylnyalolide ( 4), diepoxynyalolide ( 5), and dioxanyalolide ( 6). The structures and relative stereochemistry of the compounds were elucidated by interpretation of MS, 1D NMR, COSY, HSQC, HMBC, and NOESY experiments. Compound 1 is most likely the dienophile affording, by a Diels-Alder reaction, the four biscembranoids. Dioxanyalolide ( 6) possesses antibacterial activity against Escherichia coli at a concentration of 1.25 microg/mL. Methyl tetrahydrosarcoate ( 1) and diepoxynyalolide ( 5) exhibited LC 50 values of 1.5 microM in a brine shrimp bioassay, while desacetylnyalolide ( 4) was only mildly active.

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Artemia / drug effects
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Kenya
  • Molecular Structure
  • Terpenes / chemistry
  • Terpenes / isolation & purification

Substances

  • Diterpenes
  • Terpenes
  • methyl tetrahydrosarcoate
  • nyalolide