Isolation and Structural Elucidation of Antimicrobial Compounds from Buckwheat Hull

  • Cho Jeong-Yong (Department of Food Science & Technology and Functional Food Research Center, Chonnam National University, Faculty of Pharmaceutical Sciences, University of Tokushima) ;
  • Moon Jae-Hak (Department of Food Science & Technology and Functional Food Research Center, Chonnam National University) ;
  • Kim Hye-Kyung (Department of Food Science & Technology and Functional Food Research Center, Chonnam National University) ;
  • Ma Seung-Jin (Department of Food Engineering, Mokpo National University) ;
  • Kim Seon-Jae (Division of Food Technology & Nutrition, Chonnam National University) ;
  • Jang Mi-Young (Department of Food Science & Technology and Functional Food Research Center, Chonnam National University) ;
  • Kawazoe Kazuyoshi (Faculty of Pharmaceutical Sciences, University of Tokushima) ;
  • Takaishi Yoshihisa (Faculty of Pharmaceutical Sciences, University of Tokushima) ;
  • Park Keun-Hyung (Department of Food Science & Technology and Functional Food Research Center, Chonnam National University)
  • Published : 2006.04.01

Abstract

Three new compounds were isolated from the methanol extracts of buckwheat (Fagopyrum esculentum) hull, and their structures were determined to be 6,7-dihydroxy-3,7-dimethyl-octa-2(Z),4(E)-dienoic acid (1), 6,7-dihydroxy-3,7-dimethyl-octa-2(E),4(E)-dienoic acid (2), and 4,7-dihydroxy-3,7-dimethyl-octa-2(E),5(E)-dienoic acid (3) by NMR and MS spectroscopic analyses. These compounds at $500{\mu}g$ concentration showed antimicrobial activity against Staphylococcus aureus, demonstrated by the paper disc method.

Keywords

References

  1. Cho, J. Y., H. K. Kim, S. J. Ma, J. H. Moon, and K. H. Park. 2000. Isolation and identification of azelaic acid and 3,4- dihydroxybenzoic acid from buckwheat hull as antimicrobial substances. Food. Sci. Biotechnol. 9: 313-316
  2. Cho, J. Y., J. H. Moon, K. Y. Seong, and K. H. Park. 1998. Antimicrobial activity of 4-hydroxybenzoic acid and trans- 4-hydroxycinnamic acid isolated and identified from rice hull. Biosci. Biotechnol. Biochem. 62: 2273-2276 https://doi.org/10.1271/bbb.62.2273
  3. Duh, P. D., D.B. Yeh, and G. C. Yen. 1992. Extraction and identification of an antioxidative component from peanut hulls. J. Am. Oil Chem. Soc. 68: 814-818
  4. Holasova, M., V. Fiedlerova, H. Smrcinova, M. Orsak, J. Lachman, and S. Vavreinova. 2002. Buckwheat - the source of antioxidant activity in functional foods. Food Res. Int. 35: 207-211 https://doi.org/10.1016/S0963-9969(01)00185-5
  5. Oomah, B. D. and G.. Mazza. 1996. Flavonoids and antioxidative activities in buckwheat. J. Agric. Food Chem. 44: 1746-1750 https://doi.org/10.1021/jf9508357
  6. Mukoda, T., B. X. Sun, and A. Ishiguro. 2001. Antioxidant activities of buckwheat hull extract toward various oxidative stress in vitro and in vivo. Biol. Pharm. Bull. 24: 209-213 https://doi.org/10.1248/bpb.24.209
  7. Prestamo, G., A. Pedrazuela, M. A. Lasuncion, and G. Arroyo. 2003. Role of buckwheat diet on rats as prebiotic and healthy food. Nutr. Res. 23: 803-814 https://doi.org/10.1016/S0271-5317(03)00074-5
  8. Quettier-Deleu, C., B. Gressier, J. Vasseur, T. Dine, C. Brunet, M. Luyckx, M. Cazin, J. C. Cazin, F. Bailleul, and F. Trotin. 2000. Phenolic compounds and antioxidant activities of buckwheat (Fagopyrum esculentum Moench) hulls and flour. J. Ethnopharm. 72: 35-42 https://doi.org/10.1016/S0378-8741(00)00196-3
  9. Watanabe, M. 1998. Catechins as antioxidants from buckwheat (Fagopyrum Esculentum Moench) goats. J. Agric. Food Chem. 46: 839-845 https://doi.org/10.1021/jf9707546
  10. Watanabe, M., Y. Ohshita, and T. Tsushida. 1997. Antioxidant compounds from buckwheat (Fagopyrum esculentum Moench) hulls. J. Agric. Food Chem. 45: 1039-1044 https://doi.org/10.1021/jf9605557
  11. Wojcicki, J., L. Samochowiec, B. Gonet, S. Juzwiak, E. Dabrowska-Zamojcin, M. Katdonska, and S. Tustanowski. 1995. Effect of buckwheat extract on free radical generation in rabbits administered high-fat diet. Phytother. Res. 9: 323- 326 https://doi.org/10.1002/ptr.2650090503
  12. Wu, K., W. Zhang, P. B. Addis, R. J. Epley, A. M. Salih, and J. Lehrfeld. 1994. Antioxidant properties of wild rice. J. Agric. Food Chem. 42: 34-37 https://doi.org/10.1021/jf00037a004
  13. Xang, Y. and P. J. White. 1997. Identification and function of antioxidants from oat groats and hulls. J. Am. Oil Chem. Soc. 74: 303-307 https://doi.org/10.1007/s11746-997-0141-x
  14. Zaika, L. Z. 1988. Spices and herbs. Their antimicrobial activity and its determination. J. Food Safety 9: 97-118 https://doi.org/10.1111/j.1745-4565.1988.tb00511.x