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Org Lett. 2012 Sep 7;14(17):4486-9. doi: 10.1021/ol3019874. Epub 2012 Aug 24.

Phorone A and isophorbasone A, sesterterpenoids isolated from the marine sponge Phorbas sp.

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Center for Marine Natural Products and Drug Discovery, School of Earth and Environmental Sciences, and Research Institute of Oceanography, Seoul National University, NS-80, Seoul, 151-747, Korea.


A chemical investigation of a Korean marine sponge, Phorbas sp., yielded unprecedented sesterterpenoids phorone A (1) and isophorbasone A (2) along with ansellone B (3) and phorbasone A acetate (4). Their complete structures were elucidated by the combination of spectroscopic data and chemical manipulation. Phorone A (1) and isophorbasone A (2) have the new "phorane"(5) and "isophorbasane"(6) sesterterpenoid carbon skeletons, respectively. Ansellone B (3) and phorbasone A acetate (4) exhibited potent inhibitory activity on nitric oxide production in RAW 264.7 LPS-activated mouse macrophage cells with IC(50) values of 4.5 and 2.8 μM, respectively.

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