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Molecules 2017, 22(5), 712; doi:10.3390/molecules22050712

4-Hydroxy-7-methyl-3-phenylcoumarin Suppresses Aflatoxin Biosynthesis via Downregulation of aflK Expressing Versicolorin B Synthase in Aspergillus flavus

1,†
,
1,†
,
2,‡
and
1,‡,*
1
School of Applied Biosciences, Kyungpook National University, Daegu 41566, Korea
2
Advanced Food Safety Research Group, BK21 Plus, School of Food Science and Technology, Chung-Ang University, Anseong 17546, Korea
Authors equally contributed to this paper as first authors.
Authors equally contributed to this paper as corresponding authors.
*
Author to whom correspondence should be addressed.
Academic Editor: Philippe Jeandet
Received: 17 December 2016 / Revised: 26 April 2017 / Accepted: 27 April 2017 / Published: 29 April 2017
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Abstract

Naturally occurring coumarins possess antibacterial and antifungal properties. In this study, these natural and synthetic coumarins were used to evaluate their antifungal activities against Aspergillus flavus, which produces aflatoxins. In addition to control antifungal activities, antiaflatoxigenic properties were also determined using a high-performance liquid chromatography in conjunction with fluorescence detection. In this study, 38 compounds tested and 4-hydroxy-7-methyl-3-phenyl coumarin showed potent antifungal and antiaflatoxigenic activities against A. flavus. Inhibitory mode of antiaflatoxigenic action by 4-hydroxy-7-methyl-3-phenyl coumarin was based on the downregulation of aflD, aflK, aflQ, and aflR in aflatoxin biosynthesis. In the cases of coumarins, antifungal and aflatoxigenic activities are highly related to the lack of diene moieties in the structures. In structurally related compounds, 2,3-dihydrobenzofuran exhibited antifungal and antiaflatoxigenic activities against A. flavus. The inhibitory mode of antiaflatoxigenic action by 2,3-dihydrobenzofuran was based on the inhibition of the transcription factor (aflS) in the aflatoxin biosynthesis pathway. These potent inhibitions of 2,3-dihydrobenzofuran and 4-hydroxy-7-methyl-3-phenyl coumarin on the Aspergillus growth and production of aflatoxins contribute to the development of new controlling agents to mitigate aflatoxin contamination. View Full-Text
Keywords: 4-hydroxy-7-methyl-3-phenyl coumarin; 2,3-dihydrobenzofuran; aflatoxin production; Aspergillus flavus; reverse transcription polymerase chain reaction 4-hydroxy-7-methyl-3-phenyl coumarin; 2,3-dihydrobenzofuran; aflatoxin production; Aspergillus flavus; reverse transcription polymerase chain reaction
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Moon, Y.-S.; Kim, L.; Chun, H.S.; Lee, S.-E. 4-Hydroxy-7-methyl-3-phenylcoumarin Suppresses Aflatoxin Biosynthesis via Downregulation of aflK Expressing Versicolorin B Synthase in Aspergillus flavus. Molecules 2017, 22, 712.

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