Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Identification of Triterpenoids and Flavonoids from the Seeds of Tartary Buckwheat

  • Lee, Jeong Min (Department of Integrative Plant Science, Chung-Ang University) ;
  • Lee, Ki Ho (Department of Integrative Plant Science, Chung-Ang University) ;
  • Yoon, Young-Ho (Highland Agriculture Research Center, National Institute of Crop Science) ;
  • Cho, Eun Ju (Department of Food Science and Nutrition, Pusan National University) ;
  • Lee, Sanghyun (Department of Integrative Plant Science, Chung-Ang University)
  • Received : 2013.05.15
  • Accepted : 2013.06.12
  • Published : 2013.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Phytochemical constituents were isolated from the seeds of tartary buckwheat (Fagopyrum tataricum) by open column chromatography. Their structures were elucidated as ${\beta}$-sitosterol (1), ${\beta}$-sitosterol-3-O-glucoside (2), oleanolic acid (3), kaempferol (4), quercetin (5), kaempferol-3-O-rutinoside (6), and quercetin-3-O-rutinoside (7) on the basis of spectroscopic analysis including $^1H$-, $^{13}C$-NMR, and MS. To our knowledge, oleanolic acid (3) has been isolated for the first time from the seeds of Fagopyrum species. The total contents of compounds 4 - 7 were 0.500 mg/g in Daesan maemil, 0.312 mg/g in Yangjul maemil, and 2.185 mg/g in tartary buckwheat.

Keywords

References

  1. Bao, T., Peng, S., Zhou, Z., and Li, B., Chemical constituents of buckwheat. Nat. Prod. Res. Developm. 15, 24-26 (2003).
  2. Choi, J.Y., Cho, E.J., Lee, H.S., Lee, J.M., Yoon, Y.H., and Lee, S., Tartary buckwheat improves cognition and memory function in an in vivo amyloid-${\beta}$-induced Alzheimer model. Food Chem. Toxicol. 53, 105-111 (2013). https://doi.org/10.1016/j.fct.2012.11.002
  3. Choi, J.Y., Lee, J.M., Yoon, Y.H., Cho, E.J., and Lee, S., Radical scavenging activity and protective effect of fractions and rutin from tartary buckwheat against oxidative stress in C6 glioma cell. Cancer Prev. Res. 17, 74-79 (2012).
  4. Christa, K. and Soral-Smietana, M., Buckwheat grains and buckwheat products-nutritional and prophylactic value of their components - a review. Czech J. Food Sci. 26, 153-162 (2008)
  5. Dadakova, E. and Kalinova, J., Determination of quercetin glycosides and free quercetin in buckwheat by capillary micellar electrokinetic chromatography. J. Sep. Sci. 33, 1633-1638 (2010). https://doi.org/10.1002/jssc.200900809
  6. Fabjan, N., Rode, J., Kosir, I.J., Wang, Z.H., Zhang, Z., and Kreft, I., Tartary buckwheat (Fagopyrum tataricum Gaertn.) as a source of dietary rutin and quercetin. J. Agric. Food Chem. 51, 6452-6455 (2003). https://doi.org/10.1021/jf034543e
  7. Gohari, A.R., Saeidnia, S., Hadjiakhoondi, A., Abdoullahi, M., and Nezafati, M., Isolation and quantificative analysis of oleanolic acid from Satureja mutica Fisch. & C.A. Mey. J. Med. Plants 8, 65-69 (2009).
  8. Guo, X., Zhu, K., Zhang, H., and Yao, H., Purification and characterization of the antitumor protein from Chinese tartary buckwheat (Fagopyrum tataricum Gaertn.) water soluble extracts. J. Agric. Food Chem. 55, 6958-6961 (2007). https://doi.org/10.1021/jf071032+
  9. Guo, Z.J., Bu, X.X., Wang, J.X., and Lv, J.X., Plant resources and research summary on "Shanxi Qi Yao". Chin. J. Ethnomed. Ethnopharm. 79, 79-81 (2006).
  10. Jiang, P., Burczynski, F., Campbell, C., Pierce, G., Austria, J.A., and Briggs, C.J., Rutin and flavonoid contents in three buckwheat species Fagopyrum esculentum, F. tataricum, and F. homotropicum and their protective effects against lipid peroxidation. Food Res. Int. 40, 356-364 (2007). https://doi.org/10.1016/j.foodres.2006.10.009
  11. Kim, S.J., Zaidul, I.S.M., Suzuki, T., Mukasa, Y., Hashimoto, N., Takigawa, S., Noda, T., Matsuura-Endo, C., and Yamauchi, H., Coparison of phenolic compositions between common and tartary buckwheat (Fagopyrum) sprouts. Food Chem. 110, 814-820 (2008). https://doi.org/10.1016/j.foodchem.2008.02.050
  12. Kim, S.J., Zaidul, I.S.M., Suzuki, T., Mukasa, Y., Hashimoto, N., Takigawa, S., Noda, T., Matsuura-Endo, C., and Yamauchi, H., A time-course study of flavonoids in the sprouts of tartary (Fagopyrum tataricum Gaertn.) buckwheats. Sci. Hortic. 115, 13-18 (2007). https://doi.org/10.1016/j.scienta.2007.07.018
  13. Kreft, S., Knapp, M., and Kreft, I., Extraction of rutin from buckwheat (Fagopyrum esculentum Moench) seeds and determination by capillary electrophoresis. J. Agric. Food Chem. 47, 4649-4652 (1999). https://doi.org/10.1021/jf990186p
  14. Kreft, I., Fabjan, N., and Yasumoto, K., Rutin content in buckwheat (Fagopyrum esculentum Moench) food materials and products. Food Chem. 98, 508-512 (2006). https://doi.org/10.1016/j.foodchem.2005.05.081
  15. Lee, H.S., Lee, J.M., Yoon, Y.H., Cho, E.J., and Lee, S., The protective effects of common and tartary buckwheats against oxidative stress and gastric cancer. Cancer Prev. Res. 16, 249-254 (2011a).
  16. Lee, S., Han, S., Kim, H.M., Lee, J.M., Mok, S.Y., and Lee, S., Isolation and identification of phytochemical constituents from Taraxacum coreanum. J. Korean Soc. Appl. Biol. Chem. 54, 73-78 (2011b).
  17. Li, D., Li, X., Ding, X., and Park, K.H., A process for preventing enzymatic degradation of rutin in tartary buckwheat (Fagopyrum tataricum Gaertn) Flour. Food Sci. Biotechnol. 17, 118-122 (2008).
  18. Li, D., Xiao, G., and Ding, X., Study on antioxidant effect of tartary buckwheat flavonoids. J. Wuxi Univ. Light Ind. 20, 44-47 (2001).
  19. Liu, C.L., Chen, Y.S., Yang, J.H., and Chiang, B.H., Antioxidant activity of tartary (Fagopyrum tataricum (L) Gaertn.) and common (Fagopyrum esculentum Moench.) buckwheat sprouts. J. Agric. Food Chem. 56, 173-178 (2008). https://doi.org/10.1021/jf072347s
  20. Mok, S.Y., Lee, J.M., Kim, H.M., Lee, D.G., Yoon, Y.H., Cho, E.J., and Lee, S., Inhibition of aldose reductase on rat lens by tartary buckwheat. Nat. Prod. Sci. 17, 230-233 (2011).
  21. Morishita, T., Yamaguchi, H., and Degi, K., The contribution of polyphenols to antioxidative activity in common buckwheat and tartary buckwheat grain. Plant Prod. Sci. 10, 99-104 (2007). https://doi.org/10.1626/pps.10.99
  22. Nemcova, L., Zima, J., Barek, J., and Janovska, D., Determination of resveratrol in grains, hulls and leaves of common and tartary buckwheat by HPLC with electrochemical detection at carbon paste electrode. Food Chem. 126, 374-378 (2011). https://doi.org/10.1016/j.foodchem.2010.10.108
  23. Park, B.J., Kwon, S.M., Park, J.I., Chang, K.J., and Park, C.H., Phenolic compounds in common and tartary buckwheat. Korean J. Crop Sci. 50, 175-180 (2005).
  24. Ren, W., Qiao, Z., Wang, H., Zhu, L., Zhang, L., Lu, Y., Cui, Y., Zhang, Z., and Wang, Z., Tartary buckwheat flavonoid activates caspase 3 and induces HL-60 cell apoptosis. Methods Find Exp. Clin. Pharmacol. 23, 427-432 (2001). https://doi.org/10.1358/mf.2001.23.8.662129
  25. Steadman, K.J., Burgoon, M.S., Lewis, B.A., Edwardson, S.E., and Obendorf, R.L., Minerals, phytic acid, tannin and rutin in buckwheat seed milling fractions. J. Sci. Food Agric. 81, 1094-1100 (2001). https://doi.org/10.1002/jsfa.914
  26. Steadman, K.J., Burgoon, M.S., Schuster, R.L., Lewis, B.A., Edwardson, S.E., and Obendorf, R.L., Fagopyritols, D-chiro-inositol, and other soluble carbohydrates in buckwheat seed milling fractions. J. Agric. Food Chem. 48, 2843-2847 (2000). https://doi.org/10.1021/jf990709t
  27. Tomotake, H., Yamamoto, N., Yanaka, N., Ohinata, H., Yamazaki, R., Kayashita, J., and Kato, N., High protein buckwheat flour suppresses hypercholesterolemia in rats and gallstone formation in mice by hypercholesterolemic diet and body fat in rats because of its low protein digestibility. Nutrition 22, 166-173 (2006). https://doi.org/10.1016/j.nut.2005.01.012
  28. Wang, J., Wang, Z., Huang, J., Sun, B., Gao, H., and Wu, L., Chemical constituents from the seeds of Fagopyrum tataricum (L.) Gaertn. J. Shenyang Pharm. Univ. 26, 270-273 (2009).
  29. Yao, Y., Shan, F., Bian, J., Chen, F., Wang, M., and Ren, G., Dchiroinositol-enriched tartary buckwheat bran extract lowers the blood glucose level in KK-Ay mice. J. Agric. Food Chem. 56, 10027-10031 (2008). https://doi.org/10.1021/jf801879m
  30. Zhang, Z.F. and Luo, W.S., The chemical components and special functions of Fagopyrum tataricum. Liangshi Yu Siliao Gongye 2, 40-41 (1998).
  31. Zheng, C., Hu, C., Ma, X., Peng, C., Zhang, H., and Qin, L., Cytotoxic phenylpropanoid glycosides from Fagopyrum tataricum (L.) Gaertn. Food Chem. 132, 433-438 (2012). https://doi.org/10.1016/j.foodchem.2011.11.017
  32. Zhu, R., Gao, N.N., and Chen, J.M., The chemical components and pharmacologic action of Fagopyrum tataricum. Zhong Guo Ye Sheng Zhi Wu Zi Yuan 22, 7-9 (2003).
  33. Zielinski, H., and Kozlowska, H., Antioxidant activity and total phenolics in selected cereal grains and their different morphological fractions. J. Agric. Food Chem. 48, 2008-2016 (2000). https://doi.org/10.1021/jf990619o