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Toxins (Basel). 2016 Aug 16;8(8). pii: E240. doi: 10.3390/toxins8080240.

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

Author information

1
School of Applied Biosciences, Kyungpook National University, Daegu 41566, Korea. space92@knu.ac.kr.
2
Department of Life Science and Biotechnology, Soonchunhyang University, Asan 31538, Korea. wschoi@sch.ac.kr.
3
School of Applied Biosciences, Kyungpook National University, Daegu 41566, Korea. inj3773@naver.com.
4
School of Applied Biosciences, Kyungpook National University, Daegu 41566, Korea. bae0601@korea.kr.
5
School of Urban and Environmental Engineering, Ulsan National Institute of Science and Technology, UNIST-gil 50, Ulsan 44919, Korea. sdchoi@unist.ac.kr.
6
Food Contaminants Division, National Institute of Food & Drug Safety Evaluation, Osong 28159, Korea. ojpaek92@korea.kr.
7
Food Contaminants Division, National Institute of Food & Drug Safety Evaluation, Osong 28159, Korea. cinee@korea.kr.
8
Advanced Food Safety Research Group, BK21 Plus, School of Food Science and Technology, Chung-Ang University, Anseong 17546, Korea. hschun@cau.ac.kr.
9
School of Applied Biosciences, Kyungpook National University, Daegu 41566, Korea. selpest@knu.ac.kr.

Abstract

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.

KEYWORDS:

Aspergillus flavus; aflatoxin; methylenedioxy compounds; piperine; reverse transcription-PCR

PMID:
27537912
PMCID:
PMC4999856
DOI:
10.3390/toxins8080240
[Indexed for MEDLINE]
Free PMC Article

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