Feigrisolide B

The total synthesis of the proposed structure of feigrisolide A is reported. Ethyl (S)-3-hydroxybutyrate was the chiral starting material. A Brown asymmetric allylation and an Evans aldol reaction were key steps of the synthesis. The NMR data of the synthetic product are different from those of the natural product. The published structure of feigrisolide A is therefore erroneous. A subsequent comparison of spectral data strongly suggests that feigrisolides A and B are identical with (-)-nonactic acid and (+)-homononactic acid, respectively.

Four new lactone compounds, named feigrisolides A to D (1 to 4), have been isolated from Streptomyces griseus. The chemical structures were determined by detail analysis of their spectroscopic data and chemical transformations. Structurally, the feigrisolides A (1) and B (2) are hepta-lactones, feigrisolide C (3) and D (4) are 16-membered macrodiolides. Biological studies showed that feigrisolide B (2) exhibited strong antibacterial, as well as medium cyctotoxic, and antiviral activities. Feigrisolides A (1), C (3) and D (4) are medium inhibitors of 3alpha-hydroxysteroid-dehydrogenase (3alpha-HSD) inhibiting activity.

Colletotrichum gloeosporioides is a main cause of rubber anthracnose, which results in very large losses for the natural rubber industry. In this study, an actinomycete strain gz-8 was isolated and had strong antagonistic activity against C. gloeosporioides, with an inhibition rate of 72.5 %. Strain gz-8 was identified as Streptomyces badius. Three active compounds were separated from S. badius gz-8 and identified as feigrisolide B, feigrisolide C and dinactin according to the mass spectrometry and NMR-spectra results. In the three compounds, dinactin exhibited the best antifungal activity against C. gloeosporioides, with an EC50 value of 2.55 μg/mL, and its minimum inhibitory concentration was 44 μg/mL. Dinactin had broad inhibitory activities against nine other pathogenic fungi, and it also had an obvious control effect on rubber anthracnose comparable to that of chlorothalonil. Dinactin could inhibit the conidiogenesis and spore germination of C. gloeosporioides. This report will contribute to understanding the antifungal activity of dinactin against C. gloeosporioides.