Heterofibrins: Inhibitors of lipid droplet formation from a deep-water southern Australian marine sponge, Spongia (Heterofibria) sp.

Salim, Angela A., Rae, James, Fontaine, Frank, Conte, Melissa M., Khalil, Zeinab, Martin, Sally, Parton, Robert G. and Capon, Robert J. (2010) Heterofibrins: Inhibitors of lipid droplet formation from a deep-water southern Australian marine sponge, Spongia (Heterofibria) sp.. Organic and Biomolecular Chemistry, 8 14: 3188-3194. doi:10.1039/c003840g


Author Salim, Angela A.
Rae, James
Fontaine, Frank
Conte, Melissa M.
Khalil, Zeinab
Martin, Sally
Parton, Robert G.
Capon, Robert J.
Title Heterofibrins: Inhibitors of lipid droplet formation from a deep-water southern Australian marine sponge, Spongia (Heterofibria) sp.
Formatted title
Heterofibrins: Inhibitors of lipid droplet formation from a deep-water southern Australian marine sponge, Spongia (Heterofibria) sp.
Journal name Organic and Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
1477-0539
Publication date 2010-07-21
Sub-type Article (original research)
DOI 10.1039/c003840g
Open Access Status Not Open Access
Volume 8
Issue 14
Start page 3188
End page 3194
Total pages 7
Editor Richard Kelly
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Language eng
Formatted abstract
A bioassay-guided search for inhibitors of lipid droplet formation in a deep-water southern Australian marine sponge, Spongia (Heterofibria) sp., yielded six new compounds, fatty acids heterofibrins A1 (1) and B1 (4), along with related monolactyl and dilactyl esters, heterofibrins A2 (2), B2 (5), A3 (3) and B3 (6). Heterofibrin structures were assigned on the basis of detailed spectroscopic analysis, with comparison to chiral synthetic model compounds. All heterofibrins possess a diyne-ene moiety, while the monolactyl and dilactyl moiety featured in selected heterofibrins is unprecedented in the natural products literature. SAR by co-metabolite studies on the heterofibrins confirmed them to be non-cytotoxic, with the carboxylic acids 1 and 4 inhibiting lipid droplet formation in A431 fibroblast cell lines. Such inhibitors have potential application in the management of obesity, diabetes and atherosclerosis.
© The Royal Society of Chemistry 2010.
Keyword Acetylenic acids
Xestospongia-testudinaria
Fatty acids
Derivatives
Santalaceae
Metabolism
Olacaceae
Truncata
Alcohols
Seed
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2011 Collection
Institute for Molecular Bioscience - Publications
 
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Created: Sun, 25 Jul 2010, 10:03:37 EST