SpringerLink
Log in

Comparative study of isoflavones in wild and cultivated soybeans as well as bean products by high-performance liquid chromatography coupled with mass spectrometry and chemometric techniques

  • Original Paper
  • Published:
European Food Research and Technology Aims and scope Submit manuscript

Abstract

A high-performance liquid chromatography method coupled with mass spectrometry and chemometric analysis has been developed for the quality evaluation of wild and cultivated soybean as well as bean products. Fifteen isoflavones were qualified by LC–MS and quantified by HPLC. The assay results demonstrated that the type of isoflavones was quite similar between cultivated and wild soybean, and 6″-O-malonylglucosides were the main ingredients in soybean, while glucosides and aglycones were abundant in bean products. Moreover, the unsupervised chemometric methods including principal component analysis (PCA) and cluster analysis revealed that different species, geographic locations, and the processing methods have great influences on the chemical properties of soybean and bean products. In conclusion, HPLC coupled with chemometric techniques would be a very flexible and reliable method for dietary selection of soybean and bean products.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Wang KJ, Yamashita T, Watanabe M, Takahata Y (2004) Genetic characterization of a novel Tib-derived variant of soybean Kunitz trypsin inhibitor detected in wild soybean (Glycine soja). Genome 47:9–14

    Article  CAS  Google Scholar 

  2. Fukuda T, Maruyama N, Kanazawa A, Abe J, Shimamoto Y, Hiemori M, Tsuji H, Tanisaka T, Utsumi S (2005) Molecular analysis and physicochemical properties of electrophoretic variants of wild soybean Glycine soja storage proteins. J Agric Food Chem 53:3658–3665

    Article  CAS  Google Scholar 

  3. Pizzutti IR, de Kok A, Zanella R, Adaime MB, Hiemstra M, Wickert C, Prestes OD (2007) Method validation for the analysis of 169 pesticides in soya grain, without clean up, by liquid chromatography–tandem mass spectrometry using positive and negative electrospray ionization. J Chromatogr A 1142:123–136

    Article  CAS  Google Scholar 

  4. Kim JJ, Kim SY, Hahn SJ, Chung IM (2005) Changing soybean isoflavone composition and concentrations under two different storage conditions over 3 years. Food Res Int 38:435–444

    Article  CAS  Google Scholar 

  5. Rostagno MA, Palma M, Barroso CG (2005) Solid-phase extraction of soy isoflavones. J Chromatogr A 1076:110–117

    Article  CAS  Google Scholar 

  6. Ali AA, Velasquez MT, Hansen CT, Mohamed AI, Bhathena SJ (2004) Effects of soybean isoflavones, probiotics, and their interactions on lipid metabolism and endocrine system in an animal model of obesity and diabetes. J Nutr Biochem 15:583–590

    Article  CAS  Google Scholar 

  7. Wang X, Ge X, Bai X, Song C, Niu L, Xu H (2003) Effects of Semen Sojae Preparatum on lipid metabolism in ovariectomized rat. Zhong Yao Cai 26:652–654

    Google Scholar 

  8. Thomas BF, Zeisel SH, Busby MG, Hill JM, Mitchell RA, Scheffler NM, Brown SS, Bloeden LT, Dix KJ, Jeffcoat AR (2001) Quantitative analysis of the principle soy isoflavones genistein, daidzein and glycitein, and their primary conjugated metabolites in human plasma and urine using reversed-phase high-performance liquid chromatography with ultraviolet detection. J Chromatogr B 760:191–205

    Article  CAS  Google Scholar 

  9. Islam F, Sparkes C, Roodenrys S, Astheimer L (2008) Short-term changes in endogenous estrogen levels and consumption of soy isoflavones affect working and verbal memory in young adult females. Nutr Neurosci 11:251–262

    Article  CAS  Google Scholar 

  10. Wu AH, Stanczyk FZ, Hendrich S, Murphy PA, Zhang C, Wan P, Pike MC (2000) Effects of soyfoods on ovarian function in premenopausal women. Brit J Cancer 82:1879–1886

    Article  CAS  Google Scholar 

  11. Gu LW, Gu WY (2001) Characterisation of soy isoflavones and screening for novel malonyl glucosides using high-performance liquid chromatography-electrospray ionisation-mass spectrometry. Phytochem Anal 12:377–382

    Article  CAS  Google Scholar 

  12. Lee YW, Kim JD, Zheng JZ, Row KH (2007) Comparisons of isoflavones from Korean to Chinese soybean and processed products. Biochem Eng J 36:49–53

    Article  CAS  Google Scholar 

  13. Kim JA, Hong SB, Jung WS, Yu CY, Ma KH, Gwag JG, Chung IM (2007) Comparison of isoflavones composition in seed, embryo, cotyledon and seed coat of cooked-with-rice and vegetable soybean (Glycine max L.) varieties. Food Chem 102:738–744

    Article  CAS  Google Scholar 

  14. Cavaliere C, Cucci F, Foglia P, Guarino C, Samperi R, Lagana A (2007) Flavonoid profile in soybeans by high-performance liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 21:2177–2187

    Article  CAS  Google Scholar 

  15. Rostagno MA, Palma M, Barroso CG (2007) Fast analysis of soy isoflavones by high-performance liquid chromatography with monolithic columns. Anal Chim Acta 582:243–249

    Article  CAS  Google Scholar 

  16. 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. J Sep Sci 30:604–611

    Article  CAS  Google Scholar 

  17. Peng YY, Chu QC, Ye JN (2004) Determination of isoflavones in soy products by capillary electrophoresis with electrochemical detection. Food Chem 87:135–139

    Article  CAS  Google Scholar 

  18. Sutil GA, Mandarino JM, Laurindo JB, Benassi V, Góes-Favoni S, Petrus JCC (2008) Effect of hydrothermal treatment and pH on the formation of aglycones in soybean. Eur Food Res Technol 227:1729–1731

    Article  CAS  Google Scholar 

  19. Riedl KM, Lee JH, Renita M, St Martin SK, Schwartz SJ, Vodovotz Y (2007) Isoflavone profiles, phenol content, and antioxidant activity of soybean seeds as influenced by cultivar and growing location in Ohio. J Sci Food Agric 87:1197–1206

    Article  CAS  Google Scholar 

  20. Lee SW, Lee JH (2009) Effects of oven-drying, roasting, and explosive puffing process on isoflavone distributions in soybeans. Food Chem 112:316–320

    Article  CAS  Google Scholar 

  21. Escribano S, Sánchez FJ, Lázaro A (2010) Establishment of a sensory characterization protocol for melon (Cucumis melo L.) and its correlation with physical–chemical attributes: indications for future genetic improvements. Eur Food Res Technol 231:611–621

    Article  CAS  Google Scholar 

  22. Thanaraj T, Terry LA, Bessant C (2009) Chemometric profiling of pre-climacteric Sri Lankan mango fruit (Mangifera indica L.). Food Chem 112:786–794

    Article  CAS  Google Scholar 

  23. Wardhani DH, Vazquez JA, Pandiella SS (2008) Kinetics of daidzin and genistin transformations and water absorption during soybean soaking at different temperatures. Food Chem 111:13–19

    Article  CAS  Google Scholar 

  24. Kudou S, Fleury Y, Welti D, Magnolato D, Uchida T, Kitamura K, Okubo K (1991) Malonyl isoflavone glucosides in soybean seeds (Glycine max Merrill). J Agric Food Chem 55:2227–2233

    CAS  Google Scholar 

  25. Barnes S, Kirk M, Coward L (1994) Isoflavones and their conjugates in soyfoods: extraction conditions and analysis by HPLC-mass spectrometry. J Agric Food Chem 42:2466–2474

    Article  CAS  Google Scholar 

  26. Kao TH, Chen BH (2002) An improved method for determination of isoflavones in soybean powder by liquid chromatography. Chromatographia 56:423–430

    Article  CAS  Google Scholar 

  27. Riedl KM, Lee JH, Renita M, Martin SK, Schwartz SJ, Vodovotz Y (2007) Isoflavone profiles, phenol content, and antioxidant activity of soybean seeds as influenced by cultivar and growing location in Ohio. J Sci Food Agr 87:1197–1206

    Article  CAS  Google Scholar 

  28. Rostagno MA, Araujo JMA, Sandi D (2002) Supercritical fluid extraction of isoflavones from soybean flour. Food Chem 78:111–117

    Article  CAS  Google Scholar 

  29. Coward L, Smith M, Kirk M, Barnes S (1998) Chemical modification of isoflavones in soyfoods during cooking and processing. Am J Clin Nutr 68:1486S–1491S

    CAS  Google Scholar 

  30. Kawakami Y, Tsurugasaki W, Nakamura S, Osada K (2005) Comparison of regulative functions between dietary soy isoflavones aglycone and glucoside on lipid metabolism in rats fed cholesterol. J Nutr Biochem 16:205–212

    Article  CAS  Google Scholar 

  31. Coldham NG, Darby C, Hows M, King LJ, Zhang AQ, Sauer MJ (2002) Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism. Xenobiotica 32:45–62

    Article  CAS  Google Scholar 

  32. Marini H, Minutoli L, Polito F, Bitto A, Altavilla D, Atteritano M, Gaudio A, Mazzaferro S, Frisina A, Frisina N, Lubrano C, Bonaiuto M, D’Anna R, Cannata ML, Corrado F, Adamo EB, Wilson S, Squadrito F (2007) Effects of the phytoestrogen genistein on bone metabolism in osteopenic postmenopausal women: a randomized trial. Ann Intern Med 146:839–847

    Google Scholar 

Download references

Acknowledgments

This research was financially supported by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD). The author greatly appreciates **ao-**ao Liu, Jie Yang, and Mei-Ting Ren for the technical help and experiment constructions.

Author information

Authors and Affiliations

  1. School of Pharmacy, Nan**g Medical University, Nan**g, 210029, China

    Jun-Li Hong

  2. Department of Resources Science of Traditional Chinese Medicines, China Pharmaceutical University, Nan**g, 210009, China

    **ao-Ying Qin, Pan Shu, Qi Wang, Zhen-Fang Zhou, Guo-Kai Wang, Bin-Bin Lin & Min-Jian Qin

  3. Department of Chinese Materia Medica Analysis, China Pharmaceutical University, Nan**g, 210009, China

    Qiang Wang

Authors
  1. Jun-Li Hong
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. **ao-Ying Qin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pan Shu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Qi Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zhen-Fang Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Guo-Kai Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Bin-Bin Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Qiang Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Min-Jian Qin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Qiang Wang or Min-Jian Qin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hong, JL., Qin, XY., Shu, P. et al. Comparative study of isoflavones in wild and cultivated soybeans as well as bean products by high-performance liquid chromatography coupled with mass spectrometry and chemometric techniques. Eur Food Res Technol 233, 869–880 (2011). https://doi.org/10.1007/s00217-011-1564-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00217-011-1564-z

Keywords

Search

Navigation