Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Synthesis and Biological Activities of Aklyl Thiosulfi(o)nates

Alkyl thiosulfi(o)nate 화합물의 합성과 생리활성

  • Jung, Hyun-Jin (Department of Applied Biology & Chemistry Konkuk University) ;
  • Kyung, Kyu-Hang (Department of Food Science, Sejong University) ;
  • Jung, Yi-Sook (Department of Physiology, Department of Molecular Science & Technology, Ajou University) ;
  • Kyung, Suk-Hun (Department of Molecular Biotechnology, Konkuk University)
  • 정현진 (건국대학교 응용생물화학과) ;
  • 경규항 (세종대학교 식품공학과) ;
  • 정이숙 (아주대학교 의과대학) ;
  • 경석헌 (건국대학교 분자생명공학과)
  • Published : 2008.09.30
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Abstract

Alkyl thiosulfi(o)nates, analogs of allyl-2-propene-1-thiosulfinate isolated from Allium sativum and having antibacterial activity, were chemically synthesized and their biological activities were investigated. Alkyl thiosulfinates were prepared by oxidation of corresponding disulfides with organic peroxy acid, while alkyl thiosulfonates could be obtained by oxidation of the alkyl thiosulfinates using sodium periodate. All synthetic thiosulfi(o)nates showed antibacterial activity against Staphylococcus aureus B33 and antifungal activity against Candida utilis ATCC42416. Further more synthetic alkyl thiosulfonates displayed antioxidant activity and have also prevention effect of platelet aggregation induced by collagen in rat.

본 연구에서는 마늘 중의 항미생물 작용을 가지고 있는 allyl-2-propenyl-1-thiosulfinate의 유사체들인 alkyl thiosulfinate 및 이의 산화물인 thiosulfonate화합물들을 합성하고 이들의 생물 활성을 검사하였다. Alkylsulfinate는 이황화 화합물(disulfide)를 유기 과산화산으로, 또 alkyl thiosulfonate는 thiosulfinite를 sodium periodate로 산화시켜 합성하였다. 합성한 모든 alkylthiosulfinate 및 alkyl thiosulfonate들은 Staphylococcus aureus B33에 대해서는 항세균성을, Candida utilis ATCC42416에 대해서는 항곰팡이성을 나타내었다. 나아가 이들 화합물들은 항산화성과 항응고 활성도 나타내었다.

Keywords

References

  1. Kim, M. R. and Ahn, S. Y. (1983) Garlic flavor. Korean J. Food & Nutrition. 12, 176
  2. Cavellito, C. and Bailey, J. H. (1944) Allicin, the anti-bacterial principles of Allium sativum 1. Isolation, physical properties and anti-bacterial action. J. Am. Chem. Soc. 66, 1952-1954 https://doi.org/10.1021/ja01239a049
  3. Ankri, S. and Mirelman, D. (1999) Antimicrobial properties of allicin from garlic. Microbes Infection 2, 125-129
  4. Kwon, S. K. (2003) Organosulfur compounds from Allium sativum and physiological activities. J. Applied Pharmacology 11, 8-32
  5. Block, E. (1992) The organosulfur chemistry of the Genus Allium-Implications for the organic chemistry of sulfur. Angew. Chem. Int. Ed. Engl. 31, 1135-1178 https://doi.org/10.1002/anie.199211351
  6. Iberl, B., Winker, G. and Knobloch, K. (1990) Production of allicin transformation: Ajoenes and dithiins, characterization and their determination by HPLC. Planta Med. 56, 202-211 https://doi.org/10.1055/s-2006-960926
  7. Lawson, L. D., Wang, Z. J. and Hughes, B. G. (1991) Identification and HPLC sulfides and dialk(en)yl thiosulfinates in commercial garlic products. Planta Med. 57, 363-370 https://doi.org/10.1055/s-2006-960119
  8. Block, E., Ahmad, S., Catafano, J. L., Jain, M. K. and Apitz- Castro, R. (1986) Antithrombotic organosulfur compounds from garlic: Structural, machanistic, and synthetic studies. J. Am. Chem. Soc. 108, 7045-7055 https://doi.org/10.1021/ja00282a033
  9. Yu, T. J. and Wu, C. M. (1989) Stability of allicin in garlic juice. J. Food Sci. 54, 977-980 https://doi.org/10.1111/j.1365-2621.1989.tb07926.x
  10. Small, L. D., Bailey, J. H. and Cavallito, C. J. (1947) Alkyl thiosulfinates. J. Am. Chem. Soc. 69, 1710-1713 https://doi.org/10.1021/ja01199a040
  11. Small, L. D., Bailey, J. H. and Cavallito, C. J. (1949) Comparison of some properties of thiosulfonates and thiosulfinates. J. Am. Chem. Soc. 71, 3565-3566 https://doi.org/10.1021/ja01178a531
  12. Qiuhui H., Qing Y., Yamato, O., Yamasaki, M., Maede, Y. and Yoshihara, T. (2002) Isolation and identification of organosulfur compounds oxidizing Canine Erythrocytes from Garlic (Allium sativum). J. Agric. Food Chem. 50, 1059-1062 https://doi.org/10.1021/jf011182z
  13. Wu, C, C., Sheen, L. Y. and Chen, H. W. (2001) Effercts of organosulfur compounds from garlic oil on the antioxidation system in rat liver and red blood cells. Food Chem. Toxicol. 39, 563-569 https://doi.org/10.1016/S0278-6915(00)00171-X
  14. Han, J. (1993) Highlights of the cancer chemoprevention studies in China. Prev. Med. 22, 712-722 https://doi.org/10.1006/pmed.1993.1065
  15. Mellor, A. and Tappel, A. L. (1966) The inhibition of mitochondria peroxidation by ubiquinone and ubiquinol. J. Biol. Chem. 241, 4353-4356