title: Inhibitory Activities of Alkyl Syringates and Related Compounds on Aflatoxin Production.
abstract: Inhibitors of aflatoxin production of aflatoxigenic fungi are useful for preventing aflatoxin contamination in crops. As methyl syringate weakly inhibits aflatoxin production, aflatoxin production inhibitory activities of additional alkyl syringates with alkyl chains from ethyl to octyl were examined. Inhibitory activity toward aflatoxin production of Aspergillus flavus became stronger as the length of the alkyl chains on the esters became longer. Pentyl, hexyl, heptyl, and octyl syringates showed strong activity at 0.05 mM. Heptyl and octyl parabens, and octyl gallate also inhibited aflatoxin production as strongly as octyl syringate. Alkyl parabens and alkyl gallates inhibit the complex II activity of the mitochondrial respiration chain; thus, whether alkyl syringates inhibit complex II activity was examined. Inhibitory activities of alkyl syringates toward complex II also became stronger as the length of the alkyl chains increased. The complex II inhibitory activity of octyl syringate was comparable to that of octyl paraben and octyl gallate. These results suggest that alkyl syringates, alkyl parabens, and alkyl gallates, including commonly used food additives, are useful for aflatoxin control.
authors.affiliation: Department of Applied Biological Chemistry, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan. 9000163386@mail.ecc.u-tokyo.ac.jp.
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Furukawa
authors.affiliation: Department of Applied Biological Chemistry, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan. akurin@mail.ecc.u-tokyo.ac.jp.
authors.forename: Kurin
authors.initials: K
authors.lastname: Iimura
authors.affiliation: Department of Applied Biological Chemistry, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan. taichi-5909@ezweb.ne.jp.
authors.forename: Taichi
authors.initials: T
authors.lastname: Kimura
authors.affiliation: Department of Applied Biological Chemistry, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan. a-yama@mail.ecc.u-tokyo.ac.jp.
authors.forename: Toshiyoshi
authors.initials: T
authors.lastname: Yamamoto
authors.affiliation: Department of Applied Biological Chemistry, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan. asakuda@mail.ecc.u-tokyo.ac.jp.
authors.forename: Shohei
authors.initials: S
authors.lastname: Sakuda
mesh_terms: D000348:Aflatoxins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D001231:Aspergillus flavus / Q000187:drug effects / Q000378:metabolism*; D042963:Electron Transport Complex II / Q000037:antagonists & inhibitors; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005707:Gallic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015966:Gene Expression Regulation, Fungal / Q000187:drug effects
chemical_list: D000348:Aflatoxins; D004791:Enzyme Inhibitors; C506133:methyl syringate; D005707:Gallic Acid; D042963:Electron Transport Complex II
keywords: aflatoxin; alkyl gallate; alkyl paraben; alkyl syringate; complex II; inhibitor; respiration