α-Pyrone derivatives with cytotoxic activities, from the endophytic fungus Phoma sp. YN02-P-3

Abstract

Four new α-pyrone derivatives phomones C-F (1-4) together with four known compounds (5-8) were isolated from the endophytic fungus Phoma sp. YN02-P-3. Compound 1 is the first example of 6-α,β-unsaturated ester-2-pyrone dimers via intermolecular symmetrical [2+2] cycloaddition. The chemical structures of these compounds were determined from spectroscopic data (1D/2D NMR, MS and IR). The acetylated product (9) of 1 along with compounds 1-8 were then tested for their cytotoxicity against HL-60, PC-3 and HCT-116 cell lines. Compounds 2, 3, 5 and 9 with acetyl groups showed significant inhibitory activities against the three cell lines with IC₅₀ values in the range 0.52-9.85μM. while compounds 1, 4 and 6-8 that possess no acetyl group showed no inhibitory activity (IC₅₀>50μM), indicating that the acetyl group at 10- or 12- are essential for their cytotoxic activities. The structure-activity relationships of these phomones were also reported.

Keywords: Cytotoxic activities; Phoma sp.; Phomones; Structure-activity relationships; α-Pyrone derivatives.