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Molecules 2011, 16(2), 1113-1128; doi:10.3390/molecules16021113

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 / Revised: 23 December 2010 / Accepted: 13 January 2011 / Published: 26 January 2011
(This article belongs to the Special Issue Glycosides)
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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 synthesis; oleanolic acid; glycoconjugate; anti-fungal activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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