(+)-Cyclopenol, a new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid from the fungus Penicillium sclerotiorum endogenous with the Chinese mangrove Bruguiera gymnorrhiza

Abstract

One new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid named (+)-cyclopenol (1), along with nine known compounds including viridicatol (2), 3-(dimethylaminomethyl)-1-(1,1-dimethyl-2-propenyl)indole (3), anacine (4), aurantiomide C (5), viridicatin (6), 3-O-methylviridicatin (7), verrucosidin (8), ergosterol (9), and ergosterol peroxide (10), was isolated from the EtOAc extract of fungus Penicillium sclerotiorum, an endophytic fungal strain isolated from Chinese mangrove Bruguiera gymnorrhiza. The chemical structure of the new compound 1 was elucidated on the basis of detailed spectroscopic analysis. The absolute configuration of 1 was determined by single-crystal X-ray analysis with Cu Kα radiation (λ = 1.54178 Å). To our knowledge, (+)-cyclopenol (1) represents the first example of 7-membered 2,5-dioxopiperazine isolated from mangrove endophytic fungus.

Keywords::

• Bruguiera gymnorrhiza
• mangrove fungus
• Penicillium sclerotiorum
• 2,5-dioxopiperazine
• alkaloid

Acknowledgments

This research work was financially supported by the National Marine “863” Projects (Nos 2011AA09070102 and 2013AA092902), the Natural Science Foundation of China (Nos 21021063, 81273430, 21072204, and 81302692), the SKLDR/SIMM Project (No. SIMM1203ZZ-03), and was partially funded by the EU 7th Framework Program-IRSES Project (No. 246987).