2. Academic Validation
  3. Synthesis and Antimicrobial Evaluation of Fire Ant Venom Alkaloid Based 2-Methyl-6-alkyl-Δ1,6-piperideines

Synthesis and Antimicrobial Evaluation of Fire Ant Venom Alkaloid Based 2-Methyl-6-alkyl-Δ1,6-piperideines

  • J Nat Prod. 2017 Oct 27;80(10):2795-2798. doi: 10.1021/acs.jnatprod.7b00625.
Yujie Yan 1,  Yu An 1,  Xiaozhong Wang 1,  Yingqi Chen 1,  Melissa R Jacob 2,  Babu L Tekwani 2,  Liyan Dai 1,  Xing-Cong Li 2
Affiliations

Affiliations

  • 1 Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University , Hangzhou 310027, People's Republic of China.
  • 2 National Centers for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi , University, Mississippi 38677, United States.
PMID: 29023124 DOI: 10.1021/acs.jnatprod.7b00625
Abstract

The first synthesis of 2-methyl-6-pentadecyl-Δ1,6-piperideine (1), a major alkaloid of the piperideine chemotype in fire ant venoms, and its analogues, 2-methyl-6-tetradecyl-Δ1,6-piperideine (2) and 2-methyl-6-hexadecyl-Δ1,6-piperideine (3), was achieved by a facile synthetic method starting with glutaric acid (4) and urea (5). Compound 1 showed in vitro Antifungal activity against Cryptococcus neoformans and Candida albicans with IC50 values of 6.6 and 12.4 μg/mL, respectively, and Antibacterial activity against vancomycin-resistant Enterococcus faecium with an IC50 value of 19.4 μg/mL, while compounds 2 and 3 were less active against these pathogens. All three compounds strongly inhibited the parasites Leishmania donovani promastigotes and Trypanosoma brucei with IC50 values in the range of 5.0-6.7 and 2.7-4.0 μg/mL, respectively.

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