Abstract
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.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Alkaloids / chemistry*
-
Alkaloids / isolation & purification
-
Alkaloids / pharmacology*
-
Animals
-
Antineoplastic Agents / chemistry*
-
Antineoplastic Agents / isolation & purification
-
Antineoplastic Agents / pharmacology*
-
Crystallography, X-Ray
-
Drug Screening Assays, Antitumor
-
Marine Biology
-
Molecular Conformation
-
Molecular Structure
-
Nuclear Magnetic Resonance, Biomolecular
-
Porifera / chemistry*
-
Quinones / chemistry*
-
Quinones / isolation & purification
-
Quinones / pharmacology*
-
Spiro Compounds / chemistry*
-
Spiro Compounds / isolation & purification
-
Spiro Compounds / pharmacology*
-
Stereoisomerism
-
Thiazepines / chemistry*
-
Thiazepines / isolation & purification
-
Thiazepines / pharmacology*
Substances
-
Alkaloids
-
Antineoplastic Agents
-
Quinones
-
Spiro Compounds
-
Thiazepines
-
discorhabdin A