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Determination of Isoflavones in Soybean by LC/MS/MS

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Determination of Isoflavones in Soybean by LC/MS/MS Application Note Food Testing & Agriculture Determination of Isoflavones in Soybean by LC/MS/MS Authors Abstract Maria Carolina Blassioli‑Moraes and Mirian This Application Note describes a sensitive and reliable method for Fernandes Furtado Michereff the determination of seven isoflavones in soybean samples by liquid Embrapa Recursos Genéticos chromatography/tandem mass spectrometry (LC/MS/MS). The best separation of e Biotecnologia, daidzein, genistein, glycitein, daidzin, genistin, genistein, and rutin was obtained on a Brasília, Brazil reversed-phase C18 column (Agilent ZORBAX Eclipse Plus C18, 2.1 mm × 100 mm, 1.8 µm, p/n 959758-902) under gradient elution. The proposed method is simple, Claudimir Lucio do Lago fast, and presented a linear calibration with correlation coefficients greater than Department of Fundamental 0.998. The limits of detection (LODs) and limits of quantification (LOQs), based on Chemistry, the signal-to-noise ratio (S/N), were in the range of 0.7 to 6.7 and 2.3 to 22.5 ppb, Institute of Chemistry, respectively. The method was successfully used to determine isoflavones in University of São Paulo, Brazil soybean samples. Daniela Daniel Agilent Technologies, Inc. Introduction In addition, immunoassays are adopted seven isoflavones (daidzin, glycitin, to analyze isoflavones in food products rutin, genistin, daidzein, glycitein, Soybean (Glycine max) is a complex and biological samples. Each method and genistein) in soybean samples food matrix containing low starch, has its own advantages and limitations. using LC/MS/MS. Figure 1 shows the approximately 20 % oil, and 40 % This study develops and validates molecular structures of isoflavones high‑quality protein, in addition to a method for the determination of analyzed in this work. several important bioactive compounds. Soybean products are consumed worldwide as both foods and food OH additives. They can be cooked and eaten, HO O or used to make other products such as HO O HO O O tofu, soy milk, and soy sauce. Soybean OH is also used as an additive in processed O O foods to enhance texture, flavor, or OH OH nutritional content. It is commonly Daidzein (pKa 6.48) Daidzin (pKa 8.96) used as a vegetarian alternative to conventional products to produce OH soy infant formula, soy yogurt, veggie HO O burgers, and so forth. In addition to high HO O HO O O protein and nutrient content, soybean OH also contains isoflavones, compounds O O similar to the female hormone OH OH OH OH estrogen. Isoflavones may be present Genistein (pKa 6.55) Genistin (pKa 7.27) in soybean foods and supplements as aglycones (daidzein, genistein, OH and glycitein), glycosides (daidzin, HO O OH HO O O genistin, and genistein), or malonyl‑ and O OH acetyl-glycosides. The potential impact H3CO H CO of phytoestrogens on humans and 3 O animals has fueled an ever‑increasing HO O OH interest in the study of these compounds Glycitein (pKa 6.92) Glycitin (pKa 8.96) in foods, especially in soybean. These compounds also have an influence on a plants insect resistance and can therefore in certain situations allow crop OH yields to be increased, ensuring greater HO O OH food security. OH HO Analytical methods for the O O OH O determination of phytoestrogens in OH O edible plants, plant products, and H C HO3 O biological matrices include gas HO chromatography (GC), high performance OH liquid chromatography (HPLC), and Rutin (pKa 6.37) capillary electrophoresis (CE). These Figure 1. Molecular structure of isoflavones analyzed with predicted pKa values can be coupled with various techniques (calculated at www.chemicalize.org (accessed July, 2018). such as ultraviolet absorption (UV), electrochemical detection (ED), fluorescence detection, mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopy. 2 Experimental LC conditions Instrument Agilent 1290 Infinity II LC The mass spectrometer was operated Column ZORBAX Eclipse Plus C18 2.1 mm × 100 mm, 1.8 µm (p/n 959758-902) in positive multiple reaction monitoring (MRM) mode using two specific Column temperature 40 °C transitions for each isoflavone. The Injection volume 1 µL A) Water with 0.1 % formic acid most intense transition was used for Mobile phase B) Acetonitrile quantification, and the other was used as Time (min) %A %B a qualifying ion. Table 1 lists the retention 0.0 90 10 time (RT), monitored ions, and other 0.5 90 10 Gradient 6.0 50 50 MS/MS acquisition parameters used for 7.0 10 90 the identification and quantification of 8.0 10 90 8.01 90 10 isoflavones in soybean. Stop time 9 minutes Sample preparation Flow rate 0.300 mL/min Samples of soybean seeds from two different cultivars, Dowling (resistant MS conditions to sucking insects) and Silvania Instrument Agilent 6470 triple quadrupole LC/MS (susceptible to sucking insects), were Ion mode AJS-ESI, positive ionization obtained from the Embrapa Cerrados Capillary Voltage 4,000 V Research Center (Brasília, DF, Brazil). The Sheath gas heater 300 °C samples were homogenized using liquid nitrogen in a porcelain mortar and pestle Sheath gas flow 10 L/min Drying gas flow (N ) 10 L/min to obtain a fine flour. An aliquot of 2.0 g 2 was weighed and added to a glass vial Drying gas temperature 300 °C (15-mL) containing 10 mL of methanol Nebulizer pressure 20 psi and 2 mL of aqueous 0.1 M HCl. VCharging 500 V The samples were sonicated for 20 minutes at room temperature. Then, the Table 1. RT and MS/MS acquisition parameters used for the identification and supernatant was separated and filtered quantification of isoflavones in soybean. through a filter paper, followed by a Compound RT (min) Q1a (m/z) Q3b (m/z) CEc (V) FEd (V) second filtration step using a syringe 255.0* 20 Daidzin 3.54 417.1 101 filter with a 0.45 µm PTFE membrane. 199.0 52 The solvent was removed under low 285.0* 12 Glycitin 3.64 447.2 101 pressure using a rotary evaporator, and 270.0 52 303.0* 24 the final volume was adjusted to 2 mL of Rutin 3.88 611.2 101 85.1 56 methanol. 271.0* 20 Genistin 4.23 433.1 96 153.0 60 199.0* 28 Daidzein 5.47 255.1 125 91.1 44 270.0* 28 Glycitein 5.62 285.1 125 118.0 52 153.0* 32 Genistein 6.43 271.1 135 91.1 44 a = precursor ion (Q1); b = fragment ion (Q3); c = collision energy; d = fragmentor energy. 3 100 Results and discussion ) 50 Isoflavones have acidic‑basic TIC MRM ounts (% characteristics, with pKa values ranging 0 from 6.37 to 8.96 (see Figure 1). 3.544 )C 100 Accordingly, the mobile phase was acidified with 0.1 % aqueous formic 50 Daidzid ounts (% acid to prevent the deprotonation of 0 analytes, and to improve the shape 3.641 of the chromatographic peaks. The )C 100 mobile phase composition, gradient 50 Glycitin composition, and injected volume were ounts (% 0 optimized for separation efficiency 3.881 and sensitivity. Figure 2 shows a )C 100 representative dMRM chromatogram 50 obtained for isoflavone standards Rutin ounts (% under optimized conditions using the 0 Agilent MassHunter Qualitative software 4.228 )C 100 (B.08.00). 50 The developed method has the potential Genistin ounts (% to quantify isoflavones in soybean 0 by standard addition, since it is not 5.472 )C 100 possible to find a blank for soybean. To check the linearity of the isoflavones 50 Daidzein standards, calibration curves were ounts (% 0 constructed with at least nine distinct 5.618 levels of concentration with each )C 100 measured in triplicate. Calibration 50 Glycitein curves were constructed with standard ounts (% solutions with at least nine distinct 0 6.431 levels of concentration in triplicate. The )C 100 correlation coefficients of calibration 50 curves were greater than 0.998, with Genistein relative standard deviations (RSDs) Counts (% 0 ranging from 0.2 to 3.6 % for run-to-run 3.4 3.8 4.2 4.6 5.0 5.4 5.8 6.2 6.6 7.0 precision. The LODs and LOQs were Acquisition time (min) determined with reference to the Figure 2. Normalized dMRM chromatogram at optimum conditions for the isoflavone standards at 40 ppb corresponding concentration to three each, using the MassHunter qualitative software (B.08.00). and ten times, respectively, the baseline noise, in a time close to the RT measured around each isoflavone in matrix. 4 Table 2 shows the regression equations Table 2. Figures of interest from the method developed for the determination of isoflavones in soybean by LC/MS/MS. and other characteristic parameters for the developed method, while Figure 3 Compound Linear range (ppm) y = ax + b R2 LOD (ppb) LOQ (ppb) shows the calibration curve for genistin, Daidzin 0.01 – 2.5 y = 664.2x – 5,044.9 0.998 0.7 2.4 using the MassHunter quantitative Glycitin 0.01 – 2.5 y = 265.6x – 4,880.2 0.998 0.7 2.3 software (B.08.00). Rutin 0.04 – 5.0 y = 230.9x – 2,3876.8 0.999 6.7 22.5 Genistin 0.01 – 4.0 y = 155.5x – 173.3 0.998 0.7 2.3 Daidzein 0.01 – 1.3 y = 380.9x + 8215.7 0.998 1.3 4.4 Glycitein 0.01 – 2.5 y = 51.6x + 524.9 0.998 1.5 5.0 Genistein 0.01 – 1.3 y = 314.7x + 1,600.8 0.998 1.6 5.4 a = slope; b = intercept; R2 = determination coefficient Figure 3. Calibration curve for genistin using MassHunter quantitative software (B.08.00). 5 To determine isoflavones in four soybean Table 3.
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