International Journal of Applied Science and Engineering
Published by Chaoyang University of Technology

Hung-Yu Lin1, Xiu-Ti Liang1, Wen-Goang Yang2, Wei-Jyun Chien1*

1 Department of Applied Chemistry, Chaoyang University of Technology, Taichung, Taiwan
2 Department of Leisure Services Management, Chaoyang University of Technology, Taichung, Taiwan


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ABSTRACT


Black soybean (Glycine max L.) is one of the most popular crops with various application in the world. Its seed coat contains various natural pigments compounds such as anthocyanin and flavonoid. In this study, we optimize the extraction conditions of eight polyphenols from whole of black soybean and seed coat, evaluate their extraction effect, and separation resolution at different pH-range. The multiple reaction monitoring (MRM) method was analyzed by using high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) with simultaneous positive and negative electrospray ionization in a single analytical run. Eight polyphenols were separated within 9 minutes of run time with LC-MS/MS operated mode. The calibration graphs were linear over the concentration ranges of 0.01 to 1 mg/L for all polyphenol. Regression coefficients were in the range > 0.99. The limit of detection value, calculated from the blank tests based on 3σ, was 1 µg/L for all polyphenol. The RSD values corresponding to the intra-day and inter-day repeatability were lower than 11% and accuracies between 85-115%. It is shown that the modified solvent system that applied in LC-MS/MS detection could be developed as a useful tool for the study of water-soluble phenolic compounds.


Keywords: Black soybean; LC-MS/MS; MRM; Ultrasound-assisted; Anthocyanin; Flavonoid.


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REFERENCES


  1. Akindehin, S., Jung, Y.-S., Kim, S.-N., Son, Y.-H., Lee, I., Seong, J.K., Jeong, H.W., Lee, Y.-H. 2018. Myricetin exerts anti-obesity effects through upregulation of SIRT3 in adipose tissue. Nutrients, 10, 1962.

  2. Baek, J., Lee, E., Kim, N., Kim, S.L., Choi, I., Ji, H., Chung, Y.S., Choi, M.-S., Moon, J.-K., Kim, K.-H. 2020. High throughput phenotyping for various traits on soybean seeds using image analysis. Sensors, 20, 248.

  3. Bahadori, M.B., Dinparast, L., Zengin, G., Sarikurkcu, C., Bahadori, S., Asghari, B., Movahhedin, N. 2017. Functional components, antidiabetic, anti-Alzheimer’s disease, and antioxidant activities of Salvia syriaca L. International journal of food properties 20, 1761–1772.

  4. Chen, P.-N., Chu, S.-C., Chiou, H.-L., Chiang, C.-L., Yang, S.-F., Hsieh, Y.-S. 2005. Cyanidin 3-glucoside and peonidin 3-glucoside inhibit tumor cell growth and induce apoptosis in vitro and suppress tumor growth in vivo. Nutrition and cance, 53, 232–243.

  5. Chorfa, N., Savard, S., Belkacemi, K. 2016. An efficient method for high-purity anthocyanin isomers isolation from wild blueberries and their radical scavenging activity. Food chemistry, 197, 1226–1234.

  6. Desmarchelier, A., Hamel, J., Delatour, T. 2020. Sources of overestimation in the analysis of acrylamide-in coffee by liquid chromatography mass spectrometry. Journal of Chromatography A 1610, 460566.

  7. Ezekiel, R., Singh, N., Sharma, S., Kaur, A. 2013. Beneficial phytochemicals in potato—a review. Food Research International, 50, 487–496.

  8. Ganesan, K., Xu, B. 2017. A critical review on polyphenols and health benefits of black soybeans. Nutrients, 9, 455.

  9. Ganesan, K., Xu, B. 2017. Polyphenol-rich dry common beans (Phaseolus vulgaris L.) and their health benefits. International journal of molecular sciences, 18, 2331.

  10. Green, C.O., Wheatley, A.O., Osagie, A.U., Morrison, E.Y.S.A., Asemota, H.N. 2007. Determinutesation of polymethoxylated flavones in peels of selected Jamaican and Mexican citrus (Citrus spp.) cultivars by high‐performance liquid chromatography. Biomedical chromatography 21, 48–54.

  11. Jeng, T.L., Shih, Y.J., Wu, M.T., Wang, C.S., Sung, J.M. 2013. Evaluations and Selections for High Isoflavone Black Soybean Mutants Induced by NaN 3 Treatment. American Journal of Plant Sciences, 2013.

  12. Kim, H.G., Kim, G.W., Oh, H., Yoo, S.Y., Kim, Y.O., Oh, M.S. 2011. Influence of roasting on the antioxidant activity of small black soybean (Glycine max L. Merrill). LWT-Food Science and Technology, 44, 992–998.

  13. Koh, K., Youn, J.E., Kim, H.-S. 2014. Identification of anthocyanins in black soybean (Glycine max (L.) Merr.) varieties. Journal of food science and technology, 51, 377–381.

  14. Kumari, S., Krishnan, V., Sachdev, A. 2015. Impact of soaking and germinutesation durations on antioxidants and anti-nutrients of black and yellow soybean (Glycine max. L) varieties. Journal of Plant Biochemistry and Biotechnology, 24, 355–358.

  15. Lang, H., Yang, R., Dou, X., Wang, D., Zhang, L., Li, J., Li, P. 2019. Simultaneous determinutesation of 19 phenolic compounds in oilseeds using magnetic solid phase extraction and LC-MS/MS. LWT-Food Science and Technology, 107, 221–227.

  16. Lin, H.-Y., Lin, T.-S., Wang, C.-S., Chien, H.-J., Juang, Y.-M., Chen, C.-J., Lai, C.-C. 2019. Rapid determinutesation of bioactive compounds in the different organs of Salvia Miltiorrhiza by UPLC-MS/MS. Journal of Chromatography B, 1104, 81–88.

  17. Matsukawa, T., Inaguma, T., Han, J., Villareal, M.O., Isoda, H. 2015. Cyanidin-3-glucoside derived from black soybeans ameliorate type 2 diabetes through the induction of differentiation of preadipocytes into smaller and insulin-sensitive adipocytes. The Journal of Nutritional Biochemistry, 26, 860–867.

  18. Mojica, L., Berhow, M., de Mejia, E.G. 2017. Black bean anthocyanin-rich extracts as food colorants: Physicochemical stability and antidiabetes potential. Food chemistry 229, 628–639.

  19. Nakajima, J.-i., Tanaka, I., Seo, S., Yamazaki, M., Saito, K. 2004. LC/PDA/ESI-MS profiling and radical scavenging activity of anthocyanins in various berries. Journal of Biomedicine and Biotechnology 2004, 241.

  20. Nathiya, S., Durga, M., Devasena, T. 2014. Quercetin, encapsulated quercetin and its application—A review. Analgesia, 10.

  21. Petersson, E.V., Liu, J., Sjöberg, P.J., Danielsson, R., Turner, C. 2010. Pressurized hot water extraction of anthocyanins from red onion: A study on extraction and degradation rates. Analytica chimica acta 663, 27–32.

  22. Rossetto, M., Vanzani, P., Mattivi, F., Lunelli, M., Scarpa, M., Rigo, A. 2002. Synergistic antioxidant effect of catechin and malvidin 3-glucoside on free radical-initiated peroxidation of linoleic acid in micelles. Archives of Biochemistry and Biophysics, 408, 239–245.

  23. Rue, E.A., Rush, M.D., van Breemen, R.B. 2018. Procyanidins: a comprehensive review encompassing structure elucidation via mass spectrometry. Phytochemistry Reviews, 17, 1–16.

  24. Shin, D.Y., Ryu, C.H., Lee, W.S., Kim, D.C., Kim, S.H., Hah, Y.-S., Lee, S.J., Shin, S.C., Kang, H.S., Choi, Y.H. 2009. Induction of apoptosis and inhibition of invasion in human hepatoma cells by anthocyanins from meoru. Annals of the New York Academy of Sciences, 1171, 137.

  25. Tanaka, Y., Sasaki, N., Ohmiya, A. 2008. Biosynthesis of plant pigments: anthocyanins, betalains and carotenoids. The Plant Journal 54, 733–749.

  26. Tang, B., He, Y., Liu, J., Zhang, J., Li, J., Zhou, J., Ye, Y., Wang, J., Wang, X. 2019. Kinetic investigation into pH-dependent color of anthocyanin and its sensing performance. Dyes Pigments, 170, 107643.

  27. Tripoli, E., La Guardia, M., Giammanco, S., Di Majo, D., Giammanco, M. 2007. Citrus flavonoids: Molecular structure, biological activity and nutritional properties: A review. Food chemistry, 104, 466–479.

  28. Wang, F., Chen, L., Chen, H., Chen, S., Liu, Y. 2019. Analysis of flavonoid metabolites in citrus peels (Citrus reticulata “Dahongpao”) using UPLC-ESI-MS/MS. Molecules, 24, 2680.

  29. Willemse, C.M., Stander, M.A., de Villiers, A. 2013. Hydrophilic interaction chromatographic analysis of anthocyanins. 1319, 127–140.

  30. Xie, Y., Zhu, X., Li, Y., Wang, C. 2018. Analysis of the pH-dependent Fe (iii) ion chelating activity of anthocyanin extracted from black soybean [glycine max (l.) merr.] coats. 66, 1131–1139.

  31. Yang, Y., Shi, Z., Reheman, A., Jin, J.W., Li, C., Wang, Y., Andrews, M.C., Chen, P., Zhu, G., Ling, W. 2012. Plant food delphinidin-3-glucoside significantly inhibits platelet activation and thrombosis: novel protective roles against cardiovascular diseases. 7, e37323.

  32. Yun, J.W., Lee, W.S., Kim, M.J., Lu, J.N., Kang, M.H., Kim, H.G., Kim, D.C., Choi, E.J., Choi, J.Y., Kim, H.G. 2010. Characterization of a profile of the anthocyanins isolated from Vitis coignetiae Pulliat and their anti-invasive activity on HT-29 human colon cancer cells. Food and chemical toxicology, 48, 903–909.


ARTICLE INFORMATION


Received: 2020-07-13
Revised: 2020-08-24
Accepted: 2020-08-28
Available Online: 2020-12-01


Cite this article:

Lin, H.-Y., Liang, X.-T., Yang, W.-G., Chien, W.-J. 2020. High-Performance liquid chromatography-tandem mass spectrometry with polar C18 for rapid quantification of anthocyanin and flavonoid in black soybean extracts. International Journal of Applied Science and Engineering, 17, 363–371. https://doi.org/10.6703/IJASE.202012_17(4).363

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