Figure S5 (TIF) Figure S6 (TIF) Figure S7 (TIF) References H-NMR of compound 3. C-NMR of compound 2. C-NMR of compound 3. 1. Elad Y, Evensen K (1995) Physiological aspects of resistance to Botrytis cinerea. Phytopathology 85: 637–643. 2. Latorre BA, Flores V, Sara AM, Roco A (1994) Dicarboximide-resistant strains of Botrytis cinerea from table grapes in Chile: survey and characterization. Plant Dis 78: 990–994. 3. Grayer RJ, Kokubun T (2001) Plant-fungal interactions: the search for phytoalexins and other antifungal compounds from higher plants. Phytochem- istry 56: 253–63. 4. Chong J, Poutaraud A, Hugueney P (2009) Metabolism and roles of stilbenes in plants. Plant Sci 177: 143–155. 5. Adrian M, Jeandet P, Veneau J, Weston L, Besis R (1997) Biological activity of resveratrol, a stilbenic compound from grapevines, against Botrytis cinerea, the causal agent for gray mold. J Chem Ecol 23: 1689–1702. 6. Schouten A, Wagemakers L, Stefanato FL, van der Kaaij RM, van Kan JAL (2002) Resveratrol acts as a natural profungicide and induces self-intoxication by a specific laccase. Mol Microbiol 43: 883–894. 7. Baldrian P (2006) Fungal laccases – occurrence and properties. Fems Microbiol Rev 30: 215–242. 8. Hart JH (1981) Role of phytostilbenes in decay and disease resistant. Ann Rev Phytopathol 19: 437–458. 9. Pezet R, Pond V (1995) Mode of action of Vitaceae stilbenes on fungal cells. In: ‘‘Handbook of phytoalexin metabolism and action’’ Daniel M, Purkayastha RP, eds. Marcel Dekker Inc., New York, USA. pp 317–331. 10. Pezet R, Pond V (1990) Ultrastructural observations of pterostilbene fungitoxicity in dormant conidia of Botrytis cinerea. Pers J Phytopathol 129: 19–30. 11. van Baarlen P, Legendre L, van Kan JAL (2004) Plant defense compounds against Botrytis infection. In: ‘‘Botrytis: Biology, pathology and control’’ Elad Y, Williamson B, Tudzynski P, Delen N, eds. Kluwer Academic Publishers, Boston, USA. pp 143–161. 12. Sbaghi M, Jeandet P, Bessis R, Leroux P (1996) Degradation of stilbene-type phytoalexins in relation to the pathogenicity of Botrytis cinerea to grapevines. Plant Pathol 45: 139–144. 13. Pezet R, Pont V, Hoang-Van K (1991) Evidence for oxidative detoxication of pterostilbene and resveratrol by a laccase-like stilbene oxidase produced by Botrytis cinerea. Physiol Mol Plant Pathol 39: 441–450. 14. Rossi M, Caruso F, Opazo C, Salciccioli J (2008) Crystal and molecular structure of piceatannol; Scavenging features of resveratrol and piceatannol on hydroxyl and peroxyl radicals and docking with transthyretin. J Agric Food Chem 56: 10557–10566. 15. Caruso F, Tanski J, Villegas-Estrada A, Rossi M (2004) Structural basis for antioxidant activity of trans-resveratrol: ab initio calculations and crystal and molecular structure. J Agric Food Chem 52: 7279–85. 16. Mikstacka R, Przybylska D, Rimando AM, Baer-Dubowska W (2007) Inhibition of human recombinant cytochromes P450 CYP1A1 and CYP1B1 by trans- resveratrol methyl ethers. Mol Nutr Food Res 51: 517–524. 17. Tolomeo M, Grimaudo S, Di Cristina A, Roberti M, Pizzirani D, et al. (2005) Pterostilbene and 39-hydroxypterostilbene are effective apoptosis-inducing agents in MDR and BCR-ABL-expressing leukemia cells. Int J Biochem Cell Biol 37: 1709–1726. 18. Roberti M, Pizzirani D, Simoni D, Rondanin R, Baruchello R, et al. (2003) Synthesis and biological evaluation of resveratrol and analogues as apoptosis- inducing agents. J Med Chem 46: 3546–3554. 19. Meunier G, Meunier B (1985) Evidences for an efficient demethylation of methoxyellipticine derivatives catalyzed by a peroxidise. J Amer Chem Soc 107: 2558–2560. 20. Sobarzo-Sanchez E, Castedo L, De la Fuente JR (2006) Synthesis and theoretical study on 5,6-dimethoxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7- one: Possible precursor on the aromatic demethoxylation in oxoisoaporphines. Struct Chem 17: 483–489. 21. Gledhill JR, Montgomery MG, Leslie AGW, Walker JE (2007) Mechanism of inhibition of bovine F1-ATPase by resveratrol and related polyphenols. Proc Natl Acad Sci USA 21: 13632–13637. 22. Tamura H, Mizutani A, Yukioka H, Miki N, Ohba H, et al. (1999) Effect of the methoxyiminoacetamide fungicide, SSF129, on respiratory activity in Botrytis cinerea. Pestic Sci 55: 681–686. 23. Murias M, Ja¨ger W, Handler N, Erker T, Horvath Z, et al. (2005) Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure-activity relationship. Biochem Pharmacol 69: 903–912. 24. Yang G, Jiang X, Yang H (2002) Development of novel pesticides based on phytoalexins: Part 2. Quantitative structure-activity relationships of 2-heteroaryl- 4-chromanone derivatives. Pest Manag Sci 58: 1063–1067. Antifungal Resveratrol Derivatives Author Contributions Conceived and designed the experiments: FC LM MR RA. Performed the experiments: FC LM PC MC AV RA. Analyzed the data: FC LM MC MA BM MI MR. Contributed reagents/materials/analysis tools: FC LM MC AV RA. Wrote the paper: FC LM MC MR RA. 25. Voda K, Boh B, Vrtacnik M (2004) A quantitative structure–antifungal activity relationship study of oxygenated aromatic essential oil compounds using data structuring and PLS regression analysis. J Mol Model 10: 76–84. 26. Niewiadomy A, Matysiak J, Fekner Z, Czeczco R (2006) Synthesis, antifungal activity and SAR of N-substituted and N, N-disubstituted 2,4-dihydroxythio- benzamides. J Pestic Sci 31: 14–22. 27. Pan Z, Agarwal AK, Xu T, Feng Q, Baerson SR, et al. (2008) Identification of molecular pathways affected by pterostilbene, a natural dimethylether analog of resveratrol. BMC Med Gen 1: 7. 28. Kim S, Min SY, Lee SK, Cho W-J (2003) Comparative Molecular Field Analysis Study of Stilbene Derivatives Active against A549 Lung Carcinoma. Chem Pharm Bull 51: 516–521. 29. Lee SK, Min HY, Huh SK, Kim EY, Lee EJ, et al. (2003) Styrylheterocycles: a novel class of inhibitors on lipopolysaccharide-induced nitric oxide production. Bioorg Med Chem Lett 13: 3689–3692. 30. Tofi M, Georgiou T, Montagnon T, Vassilikogiannakis G (2005) Regioselective ortho lithiation of 3-aryl and 3-styryl furans. Org Lett 7: 3347–3350. 31. Antonioletti R, Bonadies F, Ciammaichella A, Viglianti A (2008) Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis. Tetrahedron 64: 4644–4648. 32. Kim S-H, Chun Y-J (2003) Stilbene derivative with cytochrome P450 1B1 inhibitory activity, pharmaceutically acceptable salt, preparation method, pharmaceutical composition, and use in prevention of carcinogenesis. PCT Int Appl. WO 2003018013. 33. Kim S, Min SY, Lee SK, Cho W-J (2003) Comparative molecular field analysis study of stilbene derivatives active against A549 lung carcinoma. Chem Pharm Bul 51: 516–521. 34. Wu J-Y, Ho J-H, Shih S-M, Hsieh T-L, Ho T-I (1999) Solvent-Dependent Photochemical Rearrangements of Ethers of Styrylheterocycles. Org Lett (1999) 1: 1039–1041. 35. Aun CE, Clarkson TJ, Happer DAR (1990) b-Substituent effects in the carbon- 13 NMR chemical shifts of styrenes. J Chem Soc Perkin Trans 2: 645–9. 36. Wang Z, Ding Q, He X, Wu J (2009) Palladium-catalyzed decarboxylative cross- coupling reaction of cinnamic acid with aryl iodide. Org Biomol Chem 7: 863–865. 37. Chu L-T, Yu P-C, Wu B-J, Liao Y-C, Chou C-H (2007) Synthesis of areno[e]indenes by the flash vacuum pyrolysis of 4-methoxystyryl arenes. Heterocycles 71: 165–173. 38. Lee SK, Park E-J, Lee E, Min H-Y, Kim E-Y, et al. (2004) Styrylheterocycles as a novel class inhibitor of cyclooxygenase-2-mediated prostaglandin E2 pro- duction. Bioorg Med Chem Lett 14: 2105–2108. 39. Ho J-H, Ho T-I, Liu RSH (2001) Proton-Assisted Switching of Reaction Pathways of Stilbene Analogs Brought by Direct Irradiation. Org Lett 3: 409–411. 40. Ho T-I, Ho J-H, Wu J-Y (2000) Novel Acid-Catalyzed Hydrolysis of an Intermediate from a Photorearrangement of Stilbenes. J Amer Chem Soc 122: 8575–8576. 41. Meng X-L, Yang J-Y, Chen G-L, Wang L-H, Zhang L-J, et al. (2008) Effects of resveratrol and its derivatives on lipopolysaccharide-induced microglial activa- tion and their structure-activity relationships. Chem-Biol Interact 174: 51–59. 42. Katsuyama Y, Funa N, Horinouchi S (2007) Precursor-directed biosynthesis of stilbene methyl ethers in Escherichia coli. Biotech J 2: 1286–1293. 43. Kim S, Ko H, Park JE, Jung S, Lee SK, et al. (2002) Design, Synthesis, and Discovery of Novel trans-Stilbene Analogues as Potent Selective Human Cytochrome P450 1B1 Inhibitors. J Med Chem 45: 160–164. 44. Mu n˜oz G, Hinrichsen P, Brygoo Y, Giraud T (2002) Genetic characterisation of Botrytis cinerea populations in Chile. Mycol Res 106: 594–601. 45. Mendoza L, Araya-Maturana R, Cardona W, Delgado-Castro T, Garc´ıa C, et al. (2005) In vitro sensitivity of Botrytis cinerea to anthraquinone and anthrahydroquinone derivates. J Agric Food Chem 53: 10080–10084. 46. Chefetz B, Chen Y, Hadar Y (1998) Purification and characterization of laccase from Chaetomium thermophilium and its role in humification. Appl Env Microbiol 66: 3175–3179. 47. Bradford M (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248–254. 48. Thevissen K, Terras FRG, Broekaert WF (1999) Permeabilization of fungal membranes by plant defensins inhibit fungal growth. Appl Environ Microbiol 65: 5451–5458. 49. Perdew JP, Chevary JA, Vosko SH, Jackson KA, Pederson MR, et al. (1992) Atoms, molecules, solids, and surfaces: applications of the generalized gradient PLoS ONE | www.plosone.org 9 October 2011 | Volume 6 | Issue 10 | e25421