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

Hung-Yu Lin1, Dinar S. Saputri1, Sahri Yanti1, Dinesh Chandra Agrawal1, Wen-Goang Yang2, Wei-Jyun Chien1*

1 Department of Applied Chemistry, Chaoyang University of Technology, Taichung City 413310, Taiwan

2 Department of Leisure Services Management, Chaoyang University of Technology, Taichung City 413310, Taiwan


 

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ABSTRACT


The beneficial effects of soybean isoflavones for the human body have been confirmed, and such as antioxidant activity and suppresses cancer occurrence. Therefore, soybean is widely used as food in the world. In the past few decades, several soybean varieties have been developed. A high-performance liquid chromatography electro-spray ionization with tandem mass spectrometry (HPLC-ESI-MS/MS) approach was developed and validated to determine isoflavone in 11 soybean varieties of Taiwan. The separation of 12 isoflavones was realized with a Phenomenex F5 column (2.1 × 50 mm, 1.7 µm) and using acetonitrile as mobile phase over a total analytical run time of 15 min. An Agilent 6470 triple quadrupole mass spectrometer (QqQ) with multiple reaction monitoring (MRM) was employed in ESI positive mode was achieved for isoflavone analysis. In this method validation includes the linear relationship in the range of 3.0 to 800 ng/mL (R2 > 0.99); extraction recovery (71.2% to 93.6%); matrix effect (71.3% to 84.9%); intra- and inter-day accuracy were within 81 to 118% and intra- and inter-day precision below 15%. The LC-MS approach was successfully achieved to assess isoflavone of 11 soybean varieties, and the average total isoflavone content was 7150 ng/mL. In addition, this approach can contribute to robust applications as a workflow for the stable and sensitive detection of soybean seeds.


Keywords: Isoflanove, Soybean, Phytoestrogens, High-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS).


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REFERENCES


  1. Azam, M., Zhang, S., Abdelghany, A.M., Shaibu, A.S., Feng, Y., Li, Y., Tian, Y., Hong, H., Li, B.,Sun, J. 2020. Seed isoflavone profiling of 1168 soybean accessions from major growing ecoregions in China. Food Research International, 130, 108957–108966.

  2. Bellou, S., Karali, E., Bagli, E., Al-Maharik, N., Morbidelli, L., Ziche, M., Adlercreutz, H., Murphy, C., Fotsis, T. 2012. The isoflavone metabolite 6-methoxyequol inhibits angiogenesis and suppresses tumor growth. Molecular cancer, 11, 1–11.

  3. Bustamante-Rangel, M., Delgado-Zamarreño, M., Pérez-Martín, L., Carabias-Martínez, R. 2013. QuEChERS method for the extraction of isoflavones from soy-based foods before determination by capillary electrophoresis-electrospray ionization-mass spectrometry. Microchemical Journal, 108, 203–209.

  4. Bustamante‐Rangel, M., Delgado‐Zamarreño, M.M., Pérez‐Martín, L., Rodríguez‐Gonzalo, E., Domínguez‐Álvarez, J. 2018. Analysis of isoflavones in foods. Comprehensive Reviews in Food Science and Food Safety, 17, 391–411.

  5. Chien, H.-J., Wang, C.-S., Chen, Y.-H., Toh, J.-T., Zheng, X.-F., Hong, X.-G., Lin, H.-Y., Lai, C.-C. 2020. Rapid determination of isoflavones and other bioactive compounds in soybean using SWATH-MS. Anlytica chimica acta, 1103, 122–133.

  6. de Oliveira Silva, F., Miranda, T.G., Justo, T., da Silva Frasão, B., Conte-Junior, C.A., Monteiro, M., Perrone, D. 2018. Soybean meal and fermented soybean meal as functional ingredients for the production of low-carb, high-protein, high-fiber and high isoflavones biscuits. LWT, 90, 224–231.

  7. Dinelli, G., Aloisio, I., Bonetti, A., Marotti, I., Cifuentes, A. 2007. Compositional changes induced by UV‐B radiation treatment of common bean and soybean seedlings monitored by capillary electrophoresis with diode array detection. Journal of separation science, 30, 604–611.

  8. Famiglini, G., Palma, P., Termopoli, V., Cappiello, A. 2021. The history of electron ionization in LC-MS, from the early days to modern technologies: A review. Analytica Chimica Acta, 1167, 338350.

  9. Gómez, J.D., Vital, C.E., Oliveira, M.G., Ramos, H.J. 2018. Broad range flavonoid profiling by LC/MS of soybean genotypes contrasting for resistance to Anticarsia gemmatalis (Lepidoptera: Noctuidae). PloS one, 13, 510–534.

  10. Harada, N., Okajima, K., Arai, M., Kurihara, H., Nakagata, N., research, I. 2007. Administration of capsaicin and isoflavone promotes hair growth by increasing insulin-like growth factor-I production in mice and in humans with alopecia. Growth hormone & IGF research, 17, 408–415.

  11. Hsiao, Y.-H., Ho, C.-T., Pan, M.-H. 2020. Bioavailability and health benefits of major isoflavone aglycones and their metabolites. Journal of Functional Foods, 74, 104164–104173.

  12. Iwashina, T., Kokubugata, G., Nakamura, K., Mizuno, T., Devkota, H.P., Yokota, M., Murai, Y., Saito, Y. 2018. Flavonoids from three Wild Glycine Species in Japan and Taiwan. Natural Product Communications, 13, 1641–1644.

  13. Jung, W., Yu, O., Lau, S.-M.C., O'Keefe, D.P., Odell, J., Fader, G., McGonigle, B. 2000. Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes. Nature biotechnology, 18, 208–212.

  14. Klejdus, B., Lojková, L., Plaza, M., Šnóblová, M., Štěrbová, D. 2010. Hyphenated technique for the extraction and determination of isoflavones in algae: Ultrasound-assisted supercritical fluid extraction followed by fast chromatography with tandem mass spectrometry. Journal of Chromatography A, 1217, 7956–7965.

  15. Kurahashi, N., Inoue, M., Iwasaki, M., Tanaka, Y., Mizokami, M., Tsugane, S., Group, J.S. 2009. Isoflavone consumption and subsequent risk of hepatocellular carcinoma in a population‐based prospective cohort of Japanese men and women. International journal of cancer, 124, 1644–1649.

  16. Kurzer, M.S., Xu, X. 1997. Dietary phytoestrogens. Annual review of nutrition, 17, 353–381.

  17. López-Fernández, O., Domínguez, R., Pateiro, M., Munekata, P.E., Rocchetti, G., Lorenzo, J.M. 2020. Determination of polyphenols using liquid chromatography–tandem mass spectrometry technique (LC–MS/MS): A review. Antioxidants, 9, 479–506.

  18. Lee, J., Renita, M., Fioritto, R.J., St. Martin, S.K., Schwartz, S.J., Vodovotz, Y. 2004. Isoflavone characterization and antioxidant activity of Ohio soybeans. Journal of Agricultural and Food Chemistry, 52, 2647–2651.

  19. Lin, H.-Y., Agrawal, D.C., Yang, W.-G., Chien, W.-J. 2021. A simple HPLC-MS/MS method for the analysis of multi-mycotoxins in betel nut. nternational Journal of Applied Science and Engineering, 18, 1–7.

  20. 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. nternational Journal of Applied Science and Engineering, 17, 363–371.

  21. Liu, Y., Hassan, S., Kidd, B.N., Garg, G., Mathesius, U., Singh, K.B., Anderson, J. 2017. Ethylene signaling is important for isoflavonoid-mediated resistance to Rhizoctonia solani in roots of Medicago truncatula. Molecular plant-microbe interactions, 30, 691–700.

  22. Magiera, S., Sobik, A. 2017. Ionic liquid-based ultrasound-assisted extraction coupled with liquid chromatography to determine isoflavones in soy foods. Journal of Food Composition Analysis, 57, 94–101.

  23. Mayo, B., Vázquez, L., Flórez, A.B. 2019. Equol: a bacterial metabolite from the daidzein isoflavone and its presumed beneficial health effects. Nutrients, 11, 2231–2251.

  24. Muthyala, R.S., Ju, Y.H., Sheng, S., Williams, L.D., Doerge, D.R., Katzenellenbogen, B.S., Helferich, W.G., Katzenellenbogen, J.A. 2004. Equol, a natural estrogenic metabolite from soy isoflavones: convenient preparation and resolution of R-and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta. Bioorganic medicinal chemistry, 12, 1559–1567.

  25. Nemitz, M.C., Moraes, R.C., Koester, L.S., Bassani, V.L., von Poser, G.L., Teixeira, H.F. 2015. Bioactive soy isoflavones: extraction and purification procedures, potential dermal use and nanotechnology-based delivery systems. Phytochemistry reviews, 14, 849–869.

  26. Nile, S.H., Venkidasamy, B., Samynathan, R., Nile, A., Shao, K., Chen, T., Sun, M., Khan, M.U., Dutta, N., Thiruvengadam, M., Shariati, M.A., Rebezov, M., Kai, G.  2021. Soybean processing wastes: novel insights on their production, extraction of isoflavones, and their therapeutic Properties. Journal of Agricultural and Food Chemistry, 70, 6849-6863.

  27. Prabakaran, M., Lee, J.-H., Ahmad, A., Kim, S.-H., Woo, K.-S., Kim, M.-J., Chung, I.-M. 2018. Effect of storage time and temperature on phenolic compounds of soybean (Glycine max L.) flour. Molecules, 23, 2269–2289.

  28. Prathipati, P.K., Mandal, S., Destache, C. 2019. Development and validation of LC–MS/MS method for quantification of bictegravir in human plasma and its application to an intracellular uptake study. Biomedical Chromatography, 33, 770–777.

  29. Qasim, M. 2017. Sustainability and wellbeing: a scientometric and bibliometric review of the literature. Journal of Economic Surveys, 31, 1035–1061.

  30. Takagi, A., Kano, M., Kaga, C. 2015. Possibility of breast cancer prevention: use of soy isoflavones and fermented soy beverage produced using probiotics. International journal of molecular sciences, 16, 10907–10920.

  31. Teekachunhatean, S., Hanprasertpong, N., Teekachunhatean, T. 2013. Factors affecting isoflavone content in soybean seeds grown in Thailand. International Journal of Agronomy, 2013, 1–11.

  32. Toro-Funes, N., Odriozola-Serrano, I., Bosch-Fusté, J., Latorre-Moratalla, M., Veciana-Nogués, M., Izquierdo-Pulido, M., Vidal-Carou, M. 2012. Fast simultaneous determination of free and conjugated isoflavones in soy milk by UHPLC–UV. Food chemistry, 135, 2832–2838.

  33. Wada, K., Nakamura, K., Tamai, Y., Tsuji, M., Kawachi, T., Hori, A., Takeyama, N., Tanabashi, S., Matsushita, S., Tokimitsu, N. 2013. Soy isoflavone intake and breast cancer risk in Japan: from the Takayama study. International journal of cancer, 133, 952–960.

  34. Xiao, Y., Zhang, S., Tong, H., Shi, S. 2018. Comprehensive evaluation of the role of soy and isoflavone supplementation in humans and animals over the past two decades. Phytotherapy Research, 32, 384–394.

  35. Yang, W.T., Cho, K.M., Lee, J.H. 2020. Comparative analysis of isoflavone aglycones using microwave-assisted acid hydrolysis from soybean organs at different growth times and screening for their digestive enzyme inhibition and antioxidant properties. Food chemistry, 305, 125462–125475.

  36. Yerramsetty, V., Mathias, K., Bunzel, M., Ismail, B. 2011. Detection and structural characterization of thermally generated isoflavone malonylglucoside derivatives. Journal of agricultural food chemistry, 59, 174–183.


ARTICLE INFORMATION


Received: 2021-12-27
Revised: 2022-12-09
Accepted: 2023-02-12
Available Online: 2023-02-15


Cite this article:

Lin, H.-Y., Saputri, D.S., Yanti, S., Agrawal, D.C., Yang, W.-G., Chien, W.J. Analysis of phytoestrogens from eleven soybean cultivars using LC-MS approach. International Journal of Applied Science and Engineering, 20, 2021573. https://doi.org/10.6703/IJASE.202303_20(1).005

  Copyright The Author(s). This is an open access article distributed under the terms of the Creative Commons Attribution License (CC BY 4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are cited.