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Antifungal and Antiaflatoxigenic Methylenedioxy-Containing Compounds and Piperine-Like Synthetic Compounds

School of Applied Biosciences, Kyungpook National University, Daegu 41566, Korea
Department of Life Science and Biotechnology, Soonchunhyang University, Asan 31538, Korea
School of Urban and Environmental Engineering, Ulsan National Institute of Science and Technology, UNIST-gil 50, Ulsan 44919, Korea
Food Contaminants Division, National Institute of Food & Drug Safety Evaluation, Osong 28159, Korea
Advanced Food Safety Research Group, BK21 Plus, School of Food Science and Technology, Chung-Ang University, Anseong 17546, Korea
Authors to whom correspondence should be addressed.
These authors contributed equally to this study as corresponding authors.
Academic Editor: Ana Calvo
Toxins 2016, 8(8), 240;
Received: 20 June 2016 / Revised: 1 August 2016 / Accepted: 2 August 2016 / Published: 16 August 2016
(This article belongs to the Section Mycotoxins)
PDF [727 KB, uploaded 16 August 2016]


Twelve methylenedioxy-containing compounds including piperine and 10 piperine-like synthetic compounds were assessed to determine their antifungal and antiaflatoxigenic activities against Aspergillus flavus ATCC 22546 in terms of their structure–activity relationships. Piperonal and 1,3-benzodioxole had inhibitory effects against A. flavus mycelial growth and aflatoxin B1 production up to a concentration of 1000 μg/mL. Ten piperine-like synthetic compounds were synthesized that differed in terms of the carbon length in the hydrocarbon backbone and the presence of the methylenedioxy moiety. In particular, 1-(2-methylpiperidin-1-yl)-3-phenylprop-2-en-1-one had potent antifungal and antiaflatoxigenic effects against A. flavus up to a concentration of 1 μg/mL. This synthetic compound was remarkable because the positive control thiabendazole had no inhibitory effect at this concentration. Reverse transcription-PCR analysis showed that five genes involved in aflatoxin biosynthesis pathways were down-regulated in A. flavus, i.e., aflD, aflK, aflQ, aflR, and aflS; therefore, the synthetic compound inhibited aflatoxin production by down-regulating these genes. View Full-Text
Keywords: aflatoxin; Aspergillus flavus; methylenedioxy compounds; piperine; reverse transcription-PCR aflatoxin; Aspergillus flavus; methylenedioxy compounds; piperine; reverse transcription-PCR

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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 (CC BY 4.0).

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Moon, Y.-S.; Choi, W.-S.; Park, E.-S.; Bae, I.K.; Choi, S.-D.; Paek, O.; Kim, S.-H.; Chun, H.S.; Lee, S.-E. Antifungal and Antiaflatoxigenic Methylenedioxy-Containing Compounds and Piperine-Like Synthetic Compounds. Toxins 2016, 8, 240.

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