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J Org Chem. 2011 Nov 4;76(21):9151-6. doi: 10.1021/jo201654h. Epub 2011 Oct 3.

Anti-inflammatory and antimalarial meroterpenoids from the New Zealand ascidian Aplidium scabellum.

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  • 1School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, New Zealand.


Bioassay-directed fractionation of an extract of the New Zealand ascidian Aplidium scabellum has afforded the anti-inflammatory secondary metabolite 2-geranyl-6-methoxy-1,4-hydroquinone-4-sulfate (1) and a family of pseudodimeric meroterpenoids scabellones A (2)-D (5). The benzo[c]chromene-7,10-dione scaffold contained within scabellones A-D is particularly rare among natural products. The structures were elucidated by interpretation of NMR data. Scabellone B was also identified as a moderately potent, nontoxic inhibitor of Plasmodium falciparum.

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