title: Antifungal and Antiaflatoxigenic Methylenedioxy-Containing Compounds and Piperine-Like Synthetic Compounds.
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.
authors.affiliation: School of Applied Biosciences, Kyungpook National University, Daegu 41566, Korea. space92@knu.ac.kr.
authors.forename: Young-Sun
authors.initials: YS
authors.lastname: Moon
authors.affiliation: Department of Life Science and Biotechnology, Soonchunhyang University, Asan 31538, Korea. wschoi@sch.ac.kr.
authors.forename: Won-Sik
authors.initials: WS
authors.lastname: Choi
authors.affiliation: School of Applied Biosciences, Kyungpook National University, Daegu 41566, Korea. inj3773@naver.com.
authors.forename: Eun-Sil
authors.initials: ES
authors.lastname: Park
authors.affiliation: School of Applied Biosciences, Kyungpook National University, Daegu 41566, Korea. bae0601@korea.kr.
authors.forename: In Kyung
authors.initials: IK
authors.lastname: Bae
authors.affiliation: School of Urban and Environmental Engineering, Ulsan National Institute of Science and Technology, UNIST-gil 50, Ulsan 44919, Korea. sdchoi@unist.ac.kr.
authors.forename: Sung-Deuk
authors.initials: SD
authors.lastname: Choi
authors.affiliation: Food Contaminants Division, National Institute of Food & Drug Safety Evaluation, Osong 28159, Korea. ojpaek92@korea.kr.
authors.forename: Ockjin
authors.initials: O
authors.lastname: Paek
authors.affiliation: Food Contaminants Division, National Institute of Food & Drug Safety Evaluation, Osong 28159, Korea. cinee@korea.kr.
authors.forename: Sheen-Hee
authors.initials: SH
authors.lastname: Kim
authors.affiliation: Advanced Food Safety Research Group, BK21 Plus, School of Food Science and Technology, Chung-Ang University, Anseong 17546, Korea. hschun@cau.ac.kr.
authors.forename: Hyang Sook
authors.initials: HS
authors.lastname: Chun
authors.affiliation: School of Applied Biosciences, Kyungpook National University, Daegu 41566, Korea. selpest@knu.ac.kr.
authors.forename: Sung-Eun
authors.initials: SE
authors.lastname: Lee
mesh_terms: D016604:Aflatoxin B1 / Q000096:biosynthesis*; D000470:Alkaloids / Q000138:chemical synthesis / Q000494:pharmacology*; D001231:Aspergillus flavus / Q000187:drug effects* / Q000235:genetics / Q000254:growth & development / Q000378:metabolism; D052117:Benzodioxoles / Q000138:chemical synthesis / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000494:pharmacology*; D015966:Gene Expression Regulation, Fungal / Q000187:drug effects; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000494:pharmacology*; D053284:Polyunsaturated Alkamides / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000470:Alkaloids; D052117:Benzodioxoles; D005659:Fungicides, Industrial; D010880:Piperidines; D053284:Polyunsaturated Alkamides; D016604:Aflatoxin B1; C008922:piperine
keywords: Aspergillus flavus; aflatoxin; methylenedioxy compounds; piperine; reverse transcription-PCR