Discorhabdins revisited: cytotoxic alkaloids from southern australian marine sponges of the genera Higginsia and Spongosorites.
Chemical analysis of southern Australian marine sponges of the genera Higginsia and Spongosorites has yielded examples of the discorhabdin class of alkaloids. These include the known metabolites (+)-discorhabdin A (1), (+)-discorhabdin D (2), makaluvamine J (6), and damirone A (7), together with four new analogues, (+)-dihydrodiscorhabdin A (3), (+)-debromodiscorhabdin A (4), (+)-dihydrodiscorhabdin L (8), and (+)-discorhabdin X (5), with the latter compound being the first reported example of a thio heterocycle flanked by oxo-thio-acetal and azo-thio-acetal functionalities. Structures for the new compounds were assigned on the basis of detailed spectroscopic interpretation.
El-Naggar
Mohamed
M
Centre for Molecular Biodiversity, Institute for Molecular Bioscience, The University of Queensland, St Lucia, Queensland, 4072, Australia.
Capon
Robert J
RJ
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D008386:Marine Biology; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D013141:Spiro Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D013237:Stereoisomerism; D013841:Thiazepines / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D000470:Alkaloids; D000970:Antineoplastic Agents; D011809:Quinones; D013141:Spiro Compounds; D013841:Thiazepines; C471812:discorhabdin A