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Molecules 2013, 18(3), 3615-3629; doi:10.3390/molecules18033615
Article

Efficient Synthesis and Anti-Fungal Activity of Oleanolic Acid Oxime Esters

, , , , * ,  and
Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
* Author to whom correspondence should be addressed.
Received: 4 February 2013 / Revised: 14 March 2013 / Accepted: 15 March 2013 / Published: 21 March 2013
(This article belongs to the Special Issue Triterpenes and Triterpenoids)
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Abstract

In order to develop potential glucosamine-6-phosphate synthase inhibitors and anti-fungal agents, twenty five oleanolic acid oxime esters were synthesized in an efficient way. The structures of the new compounds were confirmed by MS, HRMS, 1H-NMR and 13C-NMR. Preliminary studies based on means of the Elson-Morgan method indicated that many compounds exhibited some inhibitory activity of glucosamine-6-phosphate synthase (GlmS), and the original fungicidal activities results showed that some of the compounds exhibited good fungicidal activities towards Sclerotinia sclerotiorum (Lib.) de Bary, Rhizoctonia solani Kuhn and Botrytis cinerea Pers at the concentration of 50 µg/mL. These compounds would thus merit further study and development as antifungal agents.
Keywords: oleanolic acid; oxime ester; glucosamine-6-phosphate synthase; anti-fungal activity oleanolic acid; oxime ester; glucosamine-6-phosphate synthase; anti-fungal activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Zhao, H.; Zhou, M.; Duan, L.; Wang, W.; Zhang, J.; Wang, D.; Liang, X. Efficient Synthesis and Anti-Fungal Activity of Oleanolic Acid Oxime Esters. Molecules 2013, 18, 3615-3629.

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