Natural products as sources of new fungicides (I): synthesis and antifungal activity of Kakuol derivatives against phytopathogenic fungi

  • Wei Shi Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Sciences, PhD. Student, Northwest A&F University, Yangling, Shaanxi
  • Tseden Nandinsuren Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Sciences, PhD. Student, Northwest A&F University, Yangling, Shaanxi
  • Wen-Ming Zhou Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Sciences, PhD. Student, Northwest A&F University, Yangling, Shaanxi
  • Jin-Ming Gao Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Sciences, PhD. Student, Northwest A&F University, Yangling, Shaanxi
Keywords: 2-hydroxy-4, 5-(methyl-enedioxy) propiophenone, kakuol dervatives, antifungal activity, structure-activity relationship

Abstract

In order to establish an advanced structural-activity relationship (SAR) and to explore the feasibility of kakuol analogues with better anti-fungi activity, a series of 2-hydroxy-4,5-methylenedioxyaryl ketones were conveniently synthesized by the Friedel-Crafts acyl reaction, etherification reaction, reduction reaction and oximation reaction. Their structures characterized by 1H and 13C NMR and HRMS methods. Their in vitro antifungal activities were assayed. Most of the derivatives showed a remarkable in vitro activity, and some of them appeared significantly more effective than a commercial fungicide hymexazol as positive control. In particular compounds 2h and 2i, were found active with a IC50 value of 3.1 mg/ml and 2.9 mg/ml against Glomerella cingulate, which suggested that 2-hydroxy-4,5-methylenedioxyaryl ketones might be a promising candidates in the development of new antifungal compounds. Compounds 2e, 5 and 6 also exhibited high antifungal activities on a wide range of organisms, which might be considered as leading compounds in the development of new antifungal compounds.

DOI: http://doi.dx.org/10.5564/mjc.v15i0.331

Mongolian Journal of Chemistry 15 (41), 2014, p94-100

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Published
2014-12-12
How to Cite
Shi, W., Nandinsuren, T., Zhou, W.-M., & Gao, J.-M. (2014). Natural products as sources of new fungicides (I): synthesis and antifungal activity of Kakuol derivatives against phytopathogenic fungi. Mongolian Journal of Chemistry, 15, 94-100. https://doi.org/10.5564/mjc.v15i0.331
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Articles