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Bioactive Rearranged and Halogenated Semisynthetic Derivatives of the Marine Natural Product Sarcophine

Bioactive Rearranged and Halogenated Semisynthetic Derivatives of the Marine Natural Product Sarcophine

Swapnali S Sawant, Paul W Sylvester, Mitchell A Avery, Prashant Desai, Diaa T A Youssef, Khalid A El Sayed

J Nat Prod. 2004 Dec;67(12):2017-23.

PMID: 15620244

Abstract:

Cembranoids are natural diterpenes with 14-membered macrocyclic rings. The simplest natural cembranoid, (+)-cembrene, was isolated from pine oleoresin. Sarcophytols A and B are known cembranoids that inhibit tumor promotion. Sarcophine is a related cembranoid isolated from the Red Sea soft coral Sarcophyton glaucum. Sarcophine and its bioconversion products and semisynthetic derivatives are reported to possess cancer chemopreventive activity. Oxymercuration-demercuration of sarcophine using Hg(OAc)2 and NaBH4 afforded four new rearranged and hydroxylated products. Bromination of sarcophine with N-bromosuccinimide (NBS) furnished two new brominated and rearranged products. Reaction with iodine gave the known iso-sarcophinone and (+)-sarcophytoxin B. Structure elucidation was based on a combination of transition state modeling, molecular dynamics, mechanistic considerations, and 2D NMR data. The antiproliferative activity of the new products is also reported.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP55038272	Sarcophine		55038-27-2	Price

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