Structural and stereochemical investigations into bromotyrosine-derived metabolites from southern Australian marine sponges, Pseudoceratina spp.

Salim, Angela A., Khalil, Zeinab G. and Capon, Robert J. (2012) Structural and stereochemical investigations into bromotyrosine-derived metabolites from southern Australian marine sponges, Pseudoceratina spp.. Tetrahedron, 68 47: 9802-9807. doi:10.1016/j.tet.2012.09.008


Author Salim, Angela A.
Khalil, Zeinab G.
Capon, Robert J.
Title Structural and stereochemical investigations into bromotyrosine-derived metabolites from southern Australian marine sponges, Pseudoceratina spp.
Formatted title
Structural and stereochemical investigations into bromotyrosine-derived metabolites from southern Australian marine sponges, Pseudoceratina spp.
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
1464-5416
Publication date 2012-11
Sub-type Article (original research)
DOI 10.1016/j.tet.2012.09.008
Volume 68
Issue 47
Start page 9802
End page 9807
Total pages 6
Place of publication Oxford, United Kingdom
Publisher Pergamon
Collection year 2013
Language eng
Formatted abstract
Chemical investigation of a southern Australian sponge, Pseudoceratina sp., resulted in the isolation of twelve bromotyrosine-derived alkaloids, comprising four new metabolites, aplysamine-7 (1), (-)-purealin B (2), purealin C (3) and purealin D (4); two new spiroisoxazole enantiomers, (-)-purealidin R (5) and (-)-aerophobin-2 (6); five known metabolites (-)-pseudoceratinine A (7), (-)-aeroplysinin-1 (8), aplysamine-2 (9), purpuramine G (10) and purpuramine J (11); and an artifact 12 derived from ethanolysis of 5. Structures for 1-12 were assigned on the basis of detailed spectroscopic analysis. A second southern Australian Pseudoceratina sp. afforded the first recorded account of a racemic bromotyrosine-derived spiroisoxazole, (±)-purealin (13b), together with the known achiral precursor purealidin A (15). A literature review of marine bromotyrosine-derived spiroisoxazoles reaffirmed the published dominance of (+)-spiroisoxazoles, acknowledging several accounts of (-)-spiroisoxazoles, while also revealing a wide range of chiroptical measurements suggestive of variable optical purity. The Pseudoceratina sp. metabolites 1-12, 13b and 15 were assessed for antibiotic properties, with the new metabolites 3 and 13b exhibiting broad spectrum activity against several Gram-positive bacteria.
Keyword Bromotyrosine
Aplysamine
Purealin
Pseudoceratina
Antibacterial
Stereochemistry
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
Institute for Molecular Bioscience - Publications
 
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