Antifungal Resveratrol Derivatives Figure 5. Effect of the compound 3 on the membrane integrity of B. cinerea. Conidia, at a final concentration of 16105 conidia ml21, were incubated in liquid minimum medium at 22uC for 15 h in the presence of 8% (v/v) methanol-DMSO (A), 70% (v/v) ethanol (B) or 100 mg ml21 of compound 3 for one (C), four (D) and six (E) hours. doi:10.1371/journal.pone.0025421.g005 dimethoxy-b-(2-furyl)- styrene (3). The synthesis of compounds 1, 2 and 3, based on the Wittig reaction [30–31], differs from that reported in the literature. NMR experiments were performed using a Varian XL-300 spectrometer, IR spectra were taken with a Shimadzu IR-740 instrument and MS spectra were recorded by an HP5971A/MS detector coupled with HP5890 gas chromato- graph. Synthesis of (E)-4-Trimethoxy-b-(2-furyl)-styrene, compound 1. NaBH4 (18 mmol) was added to a solution of 1,2,3-trimethoxy-5-benzaldehyde (18 mmol) in MeOH (18 ml) at 0uC. After 30 min the reaction mixture was concentrated under reduced pressure. The raw material was dissolved in ethyl ether (100 ml) and washed with a saturated solution of NaCl. The organic layer was dried with anhydrous Na2SO4 and the ether Figure 6. Effect of compound 3 on oxygen consumption by B. cinerea conidia. doi:10.1371/journal.pone.0025421.g006 PLoS ONE | www.plosone.org 6 October 2011 | Volume 6 | Issue 10 | e25421