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

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• 作者：Hua Zhang^a ; Zeinab G. Khalil^a ; Robert J. Capon ; ^a ; ^{r.capon@uq.edu.au}
• 关键词：Fascioquinol ; Fasciospongia ; Meroterpene ; Cytotoxicity ; Antibacterial
• 刊名：Tetrahedron
• 出版年：2011
• 出版时间：8 April 2011
• 年：2011
• 卷：67
• 期：14
• 页码：2591-2595
• 全文大小：296 K

文摘

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 1–8 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).