Fascioquinols A-F: Bioactive meroterpenes from a deep-water southern Australian marine sponge, Fasciospongia sp

Zhang, Hua, Khalil, Zeinab G. and Capon, Robert J. (2011) Fascioquinols A-F: Bioactive meroterpenes from a deep-water southern Australian marine sponge, Fasciospongia sp. Tetrahedron, 67 14: 2591-2595. doi:10.1016/j.tet.2011.02.015


Author Zhang, Hua
Khalil, Zeinab G.
Capon, Robert J.
Title Fascioquinols A-F: Bioactive meroterpenes from a deep-water southern Australian marine sponge, Fasciospongia sp
Formatted title
Fascioquinols A–F: Bioactive meroterpenes from a deep-water southern Australian marine sponge, Fasciospongia sp
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
1464-5416
Publication date 2011-04-08
Sub-type Article (original research)
DOI 10.1016/j.tet.2011.02.015
Volume 67
Issue 14
Start page 2591
End page 2595
Total pages 5
Place of publication East Park, Kidlington, Oxford, U.K.
Publisher Pergamon
Collection year 2012
Language eng
Formatted abstract
Chemical investigation of a southern Australian deep-water marine sponge, Fasciospongia sp., returned the new meroterpene sulfate fascioquinol A (1) together with a series of acid mediated hydrolysis/cyclization products, fascioquinols B (2), C (3) and D (4), and strongylophorine-22 (5). Additional co-metabolites include the new meroterpenes fascioquinol E (6) and fascioquinol F (8), together with the known sponge metabolite geranylgeranyl 1,4-hydroquinone (7). Structures were assigned to 18 on the basis of detailed spectroscopic analysis, chemical interconversion, mechanistic and biosynthetic considerations, and literature comparisons. The known 1,4-hydroquinone 7 was identified as the dominant cytotoxic principle in the Fasciospongia sp. extract, with selective inhibitory activity against gastric adenocarcinoma (AGS, IC50 8 μM) and neuroblastoma (SH-SY5Y, IC50 4 μM) cell lines. By contrast, while the fascioquinols displayed little or no inhibitory activity towards human cell lines, 1 and 2 displayed promising Gram-positive selective antibacterial activity towards Staphylococcus aureus (IC50 0.9–2.5 μM) and Bacillus subtilis (IC50 0.3–7.0 μM).
Keyword Fascioquinol
Fasciospongia
Meroterpene
Cytotoxicity
Antibacterial
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2012 Collection
Institute for Molecular Bioscience - Publications
 
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Created: Fri, 14 Oct 2011, 04:47:00 EST by Professor Robert Capon on behalf of Institute for Molecular Bioscience