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J Org Chem. 1996 Apr 19;61(8):2709-2712. doi: 10.1021/jo960040e.

Alkaloids from the Tunicate Polycarpa aurata from Chuuk Atoll.

The Journal of organic chemistry

Sayed A. Abas, M. Bilayet Hossain, Dick van Der Helm, Francis J. Schmitz, Maureen Laney, Ronnel Cabuslay, Randall C. Schatzman

Affiliations

  1. Institute of Biochemistry and Cell Biology, Syntex Discovery Research, Palo Alto, California 94304.

PMID: 11667102 DOI: 10.1021/jo960040e

Abstract

Two new alkaloids, polycarpine (1) and N,N-didesmethylgrossularine-1 (4), have been isolated from extracts of the ascidian Polycarpa aurata collected in Chuuk, Federated States of Micronesia. Three degradation products of 1 were also isolated. The structures of 1, 2, and 4 were determined by X-ray crystallography. The dimeric disulfide 1 inhibited the enzyme inosine monophosphate dehydrogenase, but the inhibition could be reversed by addition of excess dithiothreitol suggesting that 1 reacts with sulfhydryl groups on the enzyme.

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