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.
Highlights
The genus Sinularia is a dominant biomass with about 100 known species widely distributed in the tropical reef environment [1,2,3,4], presenting a rich array of chemical diversity involving sesquiterpenes, diterpenes, polyhydroxylated steroids, and polyamine compounds
The structural patterns such as cyclopentenone/cyclopentanone and unsaturated γ-lactone are unusual natural products found from the soft coral genus Sinularia
Present work provided a group of new cyclopentanone/cyclopanone and butenolide-type analogues to enrich the chemical diversity of Sinularia corals
Summary
The genus Sinularia is a dominant biomass with about 100 known species widely distributed in the tropical reef environment [1,2,3,4], presenting a rich array of chemical diversity involving sesquiterpenes, diterpenes, polyhydroxylated steroids, and polyamine compounds. Sinularia play an active role in chemical defense [5,6], and display a range of biological activities, such as antimicrobial [7], anti-inflammatory [8], and cytotoxic [9,10]. Chemical examination of the EtOAc soluble fraction of this specimen resulted in the isolation of the new cyclopentenone derivatives (1–6) and furanones (7–9), along with the known butenolide (10) (Figure 1). This paper reports the structural elucidation of the new compounds and the evaluation of their antifouling activities
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