KOREAN JOURNAL OF CROP SCIENCE (한국작물학회지)

The Korean Society of Crop Science (한국작물학회)
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HPLC/MS/MS Method for Determination of Soyasaponins in the Soybean Varieties

콩 함유 사포닌의 종류 및 함량 분석

  • Han, Sang-Jun (Dept. of Agronomy, Korea National Open University)
  • 한상준 (한국방송통신대학교 자연과학대학 농학과)
  • Received : 2011.08.08
  • Accepted : 2011.08.25
  • Published : 2011.09.30
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Abstract

A sensitive and rapid high-performance liquid chromatographic-tandem mass spectrometric (HPLC/MS/MS) assay was developed for the determination of soyasaponins in soybean. Among soyasaponins, soyasaponin I was isolated and characterized from methanol extracts of soybean as analytical standards and the development of a new analytical procedure for quantification of its content in various cultivars. The structures of these compound was elucidated by $^1H$, $^{13}C$ NMR experiments and by mass spectrometric analysis. Aqueous ethanol extracts of soybean samples were injected on an Agilent XDB-C18 column ($4.6mm{\times}50mm$, $1.8{\mu}m$) with a mobile phase consisting of 10 mM ammonium acetate-acetonitrile, a flow rate of 0.3 mL/min and a total run time of 8 min. Detection was performed by mass spectrometer bin the multiple reaction monitoring (MRM) mode with negative electrospray ionization (ESI) m/z at 941 ${\rightarrow}$ 615 for soyasaponin I. In the 9 soybean samples, contents of soyasaponin I ranged from 205 to 726 mg/kg, and correlated negatively with seed size.

본 연구는 콩 함유 사포닌의 함량을 쉽고 빠르게 정량할 수 있는 방법을 개발하기 위하여 시도하였다. 사포닌 표준 물질인 soyasaponin I은 대두에서 직접 분리하여 동정하였고, 분석은 HPLC/MS/MS를 이용하였으며 그 결과는 다음과 같다. 1. DAD 또는 ELSD를 이용하여 분석할 때보다 전처리 과정을 획기적으로 줄일 수 있어 신품종 육성의 선발과 같은 대량의 분석에 적합하였다. 2. Soyasaponin I의 함량은 나물콩과 같은 소립종에서 대립종에 비해 함량이 유의하게 높은 것으로 나타났다.

Keywords

References

  1. Adlercreutz, H. and W. Mazur. 1997. Phyto-estrogens and western diseases. Ann. Med. 29 : 95-120. https://doi.org/10.3109/07853899709113696
  2. Chung, H. J., Q. Liu, R. Hoover, T. D. Warkentin, B. Vandenberg. 2008. In vitro starch digestibility, expected glycemic index, and thermal and pasting properties of flours from pea, lentil and chickpea cultivars. J. Food Chem. 118 : 316-321.
  3. Daveby, Y. D., P. Aman, J. M. Betz, and S. M. Musser. 1998. Effect of storage and extraction on ration of soyasaponin I to 2,3-Dihydro-2,5-dihydroxy-6-methyl-4-pyrone-conjugated soyasaponin I in dehulled peas (Pisum sativum L). J. Sci. Food Agric. 141-146.
  4. Kang, E. Y., S. H. Kim, S. L. Kim, S. H. Seo, E. H. Kim, H. K. Song, J. K. Ahn, and I. M. Chung. 2010. Comparison of soyasapogenol A, B concentrations in soybean seeds and sprouts. Korean J. Crop Sci. 55(2) : 165-176.
  5. Kim, S. L., M. A. Berhow, J. T. Kim, I. M. Chung, H. Y. Chi, J. Song, N. K. Park, and J. R. Son. 2006. Composition and content of soyasaponins and their interaction with chemical components in different seed-size soybeans. Korean J. Crop Sci. 51(4) : 340-347.
  6. Kim, Y. H. 2003. Biological activities of soyasaponins and their genetic and environmental variations in soybean. Korean J. Crop Sci. 48(S) : 49-57.
  7. Lampe, J. W. 2003. isoflavonoid and lignan phytoestrogens as dietary biomarkers. J. Nutr. 133(suppl 3) : 956S-964S. https://doi.org/10.1093/jn/133.3.956S
  8. Lee, H. P., L. Gourley, S. W. Duffy, J. Esteve, and J. Lee. 1991. Day NE: Dietary effects on breast-cancer risk in Singapore. Lancet. 337(8751) : 1197-1200. https://doi.org/10.1016/0140-6736(91)92867-2
  9. Perterson, G. 1995. Evaluation of the biochemical targets of genistein in tumor cells. J. Nur. 125(3 Suppl) : 784-789.
  10. Ruiz, R. G., K. R. Price, A. E. Arthur, M. E. Rose, M. J. C. Rhodes, R. G. Fenwick. 1996. Effect of soaking and cooking on the saponin content and composition of chickpeas (Cicer arietinum) and lentils (Lens culinaris). J. Agric. Food Chem. 44 : 1526-1530. https://doi.org/10.1021/jf950721v
  11. Sakamoto, S., S Kofuji, M. Kuroyanagi, A. Ueno, and S. Sekita. 1992. Saponins from Trifolium repens. Phytochemistry. 31(5) : 1773-1777. https://doi.org/10.1016/0031-9422(92)83145-O
  12. Song, T. T., S. Hendrich, and P. A. Murphy. 1999. Estrogenic activity of glycitein, a soy isoflavone. J. Agric Food Chem. 47(4) : 1607-1610. https://doi.org/10.1021/jf981054j
  13. Tham, D. M., C. D. Gardner, and W. L. Haskell. 1998. Potential health benefits of dietary phytoestrogens: a review of clinical, epidemiological, and mechanistic evidence. J. Clin. Endocrinol. Metab. 83 : 2223-2235. https://doi.org/10.1210/jc.83.7.2223
  14. Wang, X., X. Zhao, B. Yang, H. Dong, D. Liu, and L. Huang. 2011. A combination of ultrasonic-assisted extraction with RRLC-QQQ method for the determination of artemisin in the chinese herb Artemisia annua L. Phytochemical Analysis. 22(3) : 280-284. https://doi.org/10.1002/pca.1277
  15. Yoshiki, Y., J. H. Kim, and K. Okubo. 1994. Saponins conjugated with 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one from Phaseolus coccineus. Phytochemistry. 36(4) : 1009-1012. https://doi.org/10.1016/S0031-9422(00)90481-3
  16. Zhang, W., D. G. Popovich. 2008. Effect of soyasapogenol A and soyasapogenol B concentrated extracts on Hep-G2 cell proliferation and apoptosis. J. Agric. Food Chem. 56 : 2603-2608. https://doi.org/10.1021/jf0731550
  17. Zhang, W., S. P. Teng, D. G. Popovich. 2009. Generation of group B woyasaponins I and III by hydrolysis. J. Agric. Food Chem. 57 : 3620-3625. https://doi.org/10.1021/jf803663j

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