synthesis and anti-fungal activity of seven oleanolic acid glycosides七齐墩果酸苷合成和抗真菌活性.pdf

Molecules 2011, 16, 1113-1128; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides Hanqing Zhao, Guanghui Zong, Jianjun Zhang *, Daoquan Wang and Xiaomei Liang * Key Lab of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100193, China * Authors to whom correspondence should be addressed; E-Mails: zhangjianjun@ (J.Z.); nmrlab@ (X.L.); Tel.: +86-10-6273-1115. Received: 7 December 2010; in revised form: 23 December 2010 / Accepted: 13 January 2011 / Published: 26 January 2011 Abstract: In order to develop potential anti-fungal agents, seven glycoconjugates composed of α-L-rhamnose, 6-deoxy-α-L-talose, β-D-galactose, α-D-mannose, β-D-xylose- (1→4)-6-deoxy-α-L-talose, β-D-galactose-(1→4)-α-L-rhamnose, β-D-galactose-(1→3)-β- D-xylose-(1→4)-6-deoxy-α-L-talose as the glycone and oleanolic acid as the aglycone were synthesized in an efficient and practical way using glycosyl trichloroacetimidates as donors. The structures of the new compounds were confirmed by MS, 1H-NMR and 13C- NMR. Preliminary studies based on means of mycelium growth rate, indicated that all the compounds possess certain fungicidal activity against Sclerotinia sclerotiorum (Lib.) de Bary, Rhizoctonia solani Kuhn, Botrytis cinerea Pers and Phytophthora parasitica Dast. Keywords: synthesis; oleanolic acid; glycoconjug