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Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides
Key Lab of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
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Received: 7 December 2010; in revised form: 23 December 2010 / Accepted: 13 January 2011 / Published: 26 January 2011
(This article belongs to the Special Issue Glycosides
Abstract: In order to develop potential anti-fungal agents, seven glycoconjugates composed of a-L-rhamnose, 6-deoxy-a-L-talose, b-D-galactose, a-D-mannose, b-D-xylose-(1®4)-6-deoxy-a-L-talose, b-D-galactose-(1®4)-a-L-rhamnose, b-D-galactose-(1®3)-b-D-xylose-(1®4)-6-deoxy-a-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; glycoconjugate; anti-fungal activity
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MDPI and ACS Style
Zhao, H.; Zong, G.; Zhang, J.; Wang, D.; Liang, X. Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides. Molecules 2011, 16, 1113-1128.
Zhao H, Zong G, Zhang J, Wang D, Liang X. Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides. Molecules. 2011; 16(2):1113-1128.
Zhao, Hanqing; Zong, Guanghui; Zhang, Jianjun; Wang, Daoquan; Liang, Xiaomei. 2011. "Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides." Molecules 16, no. 2: 1113-1128.