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

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.

• Authors: Swapnali S Sawant, Diaa T A Youssef, Jane Reiland, Melissa Ferniz, Dario Marchetti, Khalid A El Sayed
• Journal: Journal of natural products (J Nat Prod) Vol. 69 Issue 7 Pg. 1010-3 (Jul 2006) ISSN: 0163-3864 [Print] United States
• PMID: 16872134 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

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

Topics

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