Marine Drugs 2012-06-01

Sinularones A-I, new cyclopentenone and butenolide derivatives from a marine soft coral Sinularia sp. and their antifouling activity.

Haiyan Shi, Shanjiang Yu, Dong Liu, Leen van Ofwegen, Peter Proksch, Wenhan Lin

Index: Mar. Drugs 10(6) , 1331-44, (2012)

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Abstract

Nine new compounds, namely sinularones A-I (1-9), characterized as cyclopentenone and butenolide-type analogues, were isolated from a soft coral Sinularia sp., together with a known butenolide (10). Their structures were elucidated by means of spectroscopic (IR, MS, 1D and 2D NMR, CD) analysis. The absolute configurations were determined on the basis of CD and specific rotation data in association with the computed electronic circular dichroism (ECD) by time dependent density functional theory (TD DFT) at 6-31+G(d,p)//DFT B3LYP/6-31+G(d,p) level. Compounds 1-2 and 7-10 showed potent antifouling activities against the barnacle Balanus amphitrite.