• Title/Summary/Keyword: 1-(3,5-dimethylpiperidin-1-yl)-3-(3,4,5-trimethoxyphenyl)propene

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Synthesis of Piperlongumine Derivatives Isolated from Piper longum L. and their Inhibitory Activity on Aflatoxin $B_1$ Production (Piperlongumine 유도체 합성과 $Aflatoxin\;B_1$ 생성 억제 효과)

  • Lee, Sung-Eun;Choi, Won-Sik;Lee, Hyun-Sang;Lee, Young-Haeng;Park, Byeoung-Soo
    • Applied Biological Chemistry
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    • v.46 no.4
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    • pp.361-366
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    • 2003
  • Anti-aflatoxigenic studies on synthetic pyridione alkaloids were conducted. Seven derivatives using piperlongumine as a leading compound were prepared from 3,4,5-trimethoxycinnamic acid (TMCA). These derivatives were analyzed for their structural confrmation and purity by HPLC, GC, GC/MS and $1^H-NMR$. 1-piperidin-1-yl-3-(3,4,5-trimethoxyphenyl)propenone (1) reaction with piperidine; 1-morpholin-4-yl-3-(3,4,5-trimethoypenyl)propenone (2) with morpholine; 1-(3,5-dimethylpiperidin-1-yl)-3-(3,4,5-trimethoxyphenyl)propenone (3) with 3,5-dimethylpiperdine; 1-(2-methylpiperidine-1-yl)-3-(3,4,5-trimethoxyphenyl)propenone (4) with 2-methylpiperidine; 1-(3-hydroxypiperidin-1-yl)-3- (3,4,5-trimethoxyphenyl)propenone (5) with 3-hydroxypiperidine hydrochloride; 1-[3- (3,4,5-trimethoxyphenyl)acryloyl]piperidin-2-one (6) with ${\delta}-valerolactam;\; and\;ethyl\;1-[3-(3,4,5-trimethoxyphenyl)acyloyl]piperidine-4-carboxylate$ (7) with ethyl isonipectotate were synthesized respectively. All derivatives showed an inhibitory activity on aflatoxin $B_1$ production. In conclusion, we believe that they might be an agent for the control of mycotoxin in agricultural commodities.