Four new a-pyrones, hypotiens A-D (1-4), were isolated from a fungal endophyte, Hypoxylon investiens J2, harbored in the medicinal plant Blumea balsamifera. Their structures were determined through detailed HRMS and NMR spectroscopic data. Compounds 1-4 are new a-pyrone derivatives containing an unusual dimethyl substitution in the highly unsaturated side chain. Their plausible biosynthetic pathway was discussed. Biological assay indicated that compounds 1-4 showed no antimicrobial, quorum sensing inhibitory, and cytotoxic activities. The specific side chain in a-pyrone derivatives 1-4 might be responsible for the weak pharmacological activities.
Results and discussionCompound 1 (Fig. 1), yellow powder, has a molecular formula C 18 H 22 O 4 as established by ESI-HRMS. The 1 H NMR spectrum (Table 1, and Fig. S1 †) showed the presence of ve singlet methyls (d H 1.27, 1.27, 1.95, 2.04, and 2.14). In addition, six olenic protons associated with three double bonds were also suggested in the 1 H NMR spectrum (d H 6.56, d, J ¼ 15.0 Hz; d H 7.07, dd, J ¼ 15.0, 11.0 Hz; d H 6.47, dd, J ¼ 15.0, 11.0 Hz; d H 6.55, dd, J ¼ 15.0, 10.0 Hz; d H 6.31, dd, J ¼ 15.5, 10.0 Hz; d H 5.98, d, J ¼