Biocatalytic and antimetastatic studies of the marine cembranoids sarcophine and 2-epi-16-deoxysarcophine

J Nat Prod. 2006 Jul;69(7):1010-3. doi: 10.1021/np050527v.

Abstract

The soft coral Sarcophyton glaucum is a rich resource of several bioactive cembranoids. Sarcophytol A (1) and sarcophine (2) are cembranoid diterpenes reported from this soft coral and extensively investigated for their cancer chemopreventive properties. This study aimed at investigating the antimetastatic potential of the major cembranoids, sarcophine (2) and 2-epi-16-deoxysarcophine (3), from the Red Sea soft coral S. glaucum. Biocatalytic transformation of 3 using Rhizopus stolonifer ATCC 6227a and Absidia spinosa ATCC 6648 afforded four new metabolites, 5-7 and 9, along with the known 9alpha-hydroxysarcophine (8). Sarcophine, 2-epi-16-deoxysarcophine, and metabolites 5-9 revealed significant antimetastatic activity against the highly metastatic mouse melanoma cell line (B16B15b). Cembranoids demonstrate a great potential for further development as antimetastatic agents.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / pharmacology
  • Animals
  • Anthozoa / chemistry*
  • Anticarcinogenic Agents* / chemistry
  • Anticarcinogenic Agents* / isolation & purification
  • Anticarcinogenic Agents* / pharmacology
  • Diterpenes* / chemistry
  • Diterpenes* / isolation & purification
  • Diterpenes* / pharmacology
  • Drug Screening Assays, Antitumor
  • Marine Biology
  • Melanoma / metabolism
  • Mice
  • Molecular Structure
  • Tumor Cells, Cultured
  • Wound Healing / drug effects

Substances

  • 2-epi-16-deoxysarcophine
  • Anticarcinogenic Agents
  • Diterpenes
  • sarcophytol A
  • sarcophine
  • 4-Butyrolactone