title: Synthesis and anti-fungal activity of seven oleanolic acid glycosides.
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.
authors.affiliation: Key Lab of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors.forename: Hanqing
authors.initials: H
authors.lastname: Zhao
authors.forename: Guanghui
authors.initials: G
authors.lastname: Zong
authors.forename: Jianjun
authors.initials: J
authors.lastname: Zhang
authors.forename: Daoquan
authors.initials: D
authors.lastname: Wang
authors.forename: Xiaomei
authors.initials: X
authors.lastname: Liang
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005658:Fungi / Q000187:drug effects*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000737:chemistry*
chemical_list: D000935:Antifungal Agents; D006027:Glycosides; D009828:Oleanolic Acid