Alkaloids from the Tunicate Polycarpa aurata from Chuuk Atoll
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (8), 2709-2712
- https://doi.org/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.Keywords
This publication has 16 references indexed in Scilit:
- Enzyme Inhibitors: New and Known Polybrominated Phenols and Diphenyl Ethers from Four Indo-Pacific Dysidea SpongesJournal of Natural Products, 1995
- Marine natural productsNatural Product Reports, 1995
- Probing the Active Site of Human IMP Dehydrogenase Using Halogenated Purine Riboside 5'-Monophosphates and Covalent Modification ReagentsBiochemistry, 1994
- Ascidians: producers of amino acid-derived metabolitesChemical Reviews, 1993
- Clinical pharmacokinetic study of tiazofurin administered as a 1-hour infusionInternational Journal of Cancer, 1992
- Inhibition of FKBP Rotamase Activity by Immunosuppressant FK506: Twisted Amide SurrogateScience, 1990
- Reactions of Alkylarenes, Benzyl Alcohols, Sulfides, and Phosphine with Manganese(III) Acetate–Chloride IonsBulletin of the Chemical Society of Japan, 1989
- The Application of Vacuum Liquid Chromatography to the Separation of Terpene MixturesJournal of Natural Products, 1986
- 1-(4-Chlorophenyl)-2-morpholino-2-thioxoethanoneActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1979
- IMP dehydrogenase, an enzyme linked with proliferation and malignancyNature, 1975