DOI QR코드

DOI QR Code

Synthesis and Antibacterial Activity of 1,3-Diallyltrisulfane Derivatives

  • Ren, Fang-Kui (College of Pharmaceutical Sciences, Southwest University) ;
  • He, Xiao-Yan (College of Pharmaceutical Sciences, Southwest University) ;
  • Deng, Li (College of Pharmaceutical Sciences, Southwest University) ;
  • Li, Bo-Heng (High School Attached to Southwest Normal University) ;
  • Shin, Dong-Soo (Department of Chemistry, Changwon National University) ;
  • Li, Zhu-Bo (College of Pharmaceutical Sciences, Southwest University)
  • Published : 2009.03.20

Abstract

A series of novel 1,3-diallyltrisulfane analogues were synthesized and assayed in vitro for antimicrobial activity against Gram positive, Gram negative bacteria and fungi. The antimicrobial activity of the 1,3-diallyltrisulfane derivatives showed, on the whole, very potent towards all the tested Gram positive, Gram negative and fungi (MIC ranging from 4 to 256 μg/mL). 1,3-Di(pent-4-enyl)trisulfane 3b and 1,3-bis(3-methylbut-2-enyl)trisulfane 3e exhibited the strongest antibacterial activity among all the compounds, and both of them were more active than 1,3-diallyltrisulfane (DATS). Results indicated the relationship of either carbon number or lipophilicity with antimicrobial activity presented “V” shape. These observations provided some predictions in order to further design 1,3-diallyltrisulfane derivatives with antimicrobial activity.

Keywords

References

  1. Corzo-Martinez, M.; Corzo, N.; Villamiel, M. Trends Food Sci. Tech. 2007, 18, 609-625 https://doi.org/10.1016/j.tifs.2007.07.011
  2. Moriguchi, T.; Matsuura, H.; Kodera, Y.; Itakura, Y.; Katsuki, H.; Saito, H.; Nishiyama, N. Neurochemical Research 1997, 22, 1449-1452 https://doi.org/10.1023/A:1021946210399
  3. Augusti, K. T.; Sheela, C. G. Cell Mol. Life Sci. 1966, 52, 115-119 https://doi.org/10.1007/BF01923354
  4. Oi, Y.; Kawada, T.; Shishido, C.; Wada, K.; Kominato, Y.; Nishimura, S.; Ariga, T.; Iwa, K. J. Nutrition 1999, 129, 336-342
  5. Curtis, H.; Noll, U.; St$\ddot{o}$rmann, J.; Slusarenko, A. J. Physiol. Mol. Plant Pathol. 2004, 65, 79-89 https://doi.org/10.1016/j.pmpp.2004.11.006
  6. Saleheen, D.; Ali, S. A.; Yasinzai, M. M. Fitoterapia 2004, 75, 9-13 https://doi.org/10.1016/j.fitote.2003.07.010
  7. Weber, N. D.; Anderson, D. O.; North, J. A.; Murray, B. K.; Lawson, L. D.; Hughes, B. G. Planta Med. 1999, 58, 417-423
  8. Oommen, S.; Anto, R. J.; Srinivas, G.; Karunagaran, D. Eur. J. Pharmacol. 2004, 485, 97-103 https://doi.org/10.1016/j.ejphar.2003.11.059
  9. Wu, C. C.; Chung, J. G.; Tsai, S. J.; Yang, J. H.; Sheen, L. Y. Food Chem. Toxicol. 2004, 42, 1937-1947 https://doi.org/10.1016/j.fct.2004.07.008
  10. Wu, C. C.; Sheen, L. Y.; Chen, H. W.; Tsai, S. J.; Lii, C. K. Food Chem. Toxicol. 2001, 39, 563-569 https://doi.org/10.1016/S0278-6915(00)00171-X
  11. Yin, M. C.; Cheng, W. S. Meat Sci. 2003, 63, 23-28 https://doi.org/10.1016/S0309-1740(02)00047-5
  12. Gargner, C. D.; Chatterjee, L. M.; Carlson, J. J. Atherosclerosis 2001, 154, 213–220
  13. Zhu, Y.; Zhao, M. Z.; Xu, M. X. Chinese J. Syn. Chem. 2001, 9, 541-542
  14. Sinha, P.; Kundu, A.; Roy, S. Organometallics 2001, 20, 157-162 https://doi.org/10.1021/om000533g
  15. Block, E.; Lyer, R.; Grisoni, S.; Saha, C.; Belman, S.; Lossing, F. P. J. Am. Chem. Soc. 1988, 110, 7813-7827 https://doi.org/10.1021/ja00231a037
  16. Block, E.; Ahmad, S.; Catalfamo, J. L.; Jain, M. K.; Apitz-Castro, R. J. Am. Chem. Soc. 1986, 108, 7045-7055 https://doi.org/10.1021/ja00282a033
  17. Ma, X. R. Beijing: People Health Publishing House 2001, 50-53
  18. Phillips, O. A.; Udo, E. E.; Samuel, S. M. Eur. J. Med. Chem. 2008, 43, 1095-1104 https://doi.org/10.1016/j.ejmech.2007.07.006

Cited by

  1. Antibacterial, Antioxidant and Binding Studies of Some Novel Diaryl Sulphide Derivatives vol.187, pp.11, 2012, https://doi.org/10.1080/10426507.2012.685996
  2. Effect of diallyl trisulfide derivatives on the induction of apoptosis in human prostate cancer PC-3 cells vol.363, pp.1-2, 2012, https://doi.org/10.1007/s11010-011-1159-9
  3. Detection of Volatile Metabolites of Garlic in Human Breast Milk vol.6, pp.2, 2016, https://doi.org/10.3390/metabo6020018
  4. Antibacterial Effect of (2E,2E)-4,4-Trisulfanediylbis(but-2-enoic acid) against Staphylococcus aureus vol.13, pp.5, 2018, https://doi.org/10.1371/journal.pone.0197348
  5. ChemInform Abstract: Synthesis and Antibacterial Activity of 1,3-Diallyltrisulfane Derivatives. vol.40, pp.31, 2009, https://doi.org/10.1002/chin.200931052
  6. Synthesis of Azole-containing Piperazine Derivatives and Evaluation of their Antibacterial, Antifungal and Cytotoxic Activities vol.31, pp.12, 2009, https://doi.org/10.5012/bkcs.2010.31.12.3684