Antiplatelet activities of newly synthesized derivatives of piperlongumine

Byeoung Soo Park, Dong Ju Son, Won Sik Choi, Gary R. Takeoka, Sung Ok Han, Tae Wan Kim, Sung Eun Lee

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Abstract

Piperlongumine, a pyridone alkaloid isolated from Piper longum L., exhibited a potential inhibitory effect on washed rabbit platelet aggregation induced by collagen, arachidonic acid (AA) and platelet activating factor (PAF), without any inhibitory effect on that induced by thrombin. Piperlongumine was used as a lead compound for the synthesis of new antiplatelet agents. Seven synthetic compounds were newly synthesized from 3,4,5-trimethoxycinnamic acid (TMCA). They were 1-piperidin-1-yl-3-(3,4,5-trimethoxy-phenyl)prop-2-en-1-one (1′), l-morpholin-4-yl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (2′), 1-(3,5-dhnethylpiperidin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en- 1-one(3′), 1-(2-methylpiperidin-1-yl)-3-(3,4,5-tri-methoxyphenyl)prop-2- en-1-one (4′), 1-(3-hydroxypiperidin-1-yl)-3-(3,4,5-trimethoxyphenyl)- prop-2-en-1-one (5′), 1-[3-(3,4,5-tri-methoxyphenyl) acryloyl]-piperidin- 2-one (6′) and ethyl 1-[3-(3,4,5-trimethoxyphenyl)-acryloyl]piperidine-4- carboxylate (7′). Among those seven synthetic derivatives, 1-(3,5-dimethylpiperidin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (3′) had the most inhibitory effect on platelet aggregation induced by collagen, A A and PAF.

Original languageEnglish
Pages (from-to)1195-1199
Number of pages5
JournalPhytotherapy Research
Volume22
Issue number9
DOIs
Publication statusPublished - 2008 Sep 1

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Keywords

  • Collagen
  • Piperlongumine
  • Platelet aggregation
  • Synthesis

ASJC Scopus subject areas

  • Pharmacology

Cite this

Park, B. S., Son, D. J., Choi, W. S., Takeoka, G. R., Han, S. O., Kim, T. W., & Lee, S. E. (2008). Antiplatelet activities of newly synthesized derivatives of piperlongumine. Phytotherapy Research, 22(9), 1195-1199. https://doi.org/10.1002/ptr.2432