Biocatalytic and Antimetastatic Studies of the Marine Cembranoids Sarcophine and 2-epi-16-Deoxysarcophine

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 antimet...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2006-07, Vol.69 (7), p.1010-1013
Hauptverfasser:	Sawant, S.S, Youssef, D.T.A, Reiland, J, Ferniz, M, Marchetti, D, El Sayed, K.A
Format:	Artikel
Sprache:	eng
Schlagworte:	4-Butyrolactone - analogs & derivatives 4-Butyrolactone - chemistry 4-Butyrolactone - pharmacology Absidia Absidia spinosa Alcyoniidae Animals Anthozoa - chemistry anticarcinogenic activity Anticarcinogenic Agents - chemistry Anticarcinogenic Agents - isolation & purification Anticarcinogenic Agents - pharmacology Biological and medical sciences biotransformation cembranoids cultured cells deoxysarcophine Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology diterpenoids Drug Screening Assays, Antitumor General pharmacology Marine Marine Biology Medical sciences Melanoma - metabolism metastasis Mice Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Rhizopus stolonifer sarcophine sarcophytol Sarcophyton glaucum Tumor Cells, Cultured Wound Healing - drug effects
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Zusammenfassung:	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.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np050527v