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A Comprehensive HPLC-DAD-ESI-MS Validated Method for The A comprehensive HPLC‐DAD‐ESI‐MS validated method for the quantification of sixteen phytoestrogens in food, serum and urine Supporting Information Susana Alejandra Palma‐Duran1,2, Graciela Caire‐Juvera3, Melissa María Campa‐Siqueiros3, Karina María Chávez‐Suárez3, María del Refugio Robles‐ Burgueño2, María Lourdes Gutiérrez‐Coronado2, María del Carmen Bermúdez‐Almada2, María del Socorro Saucedo‐Tamayo3, Patricia Grajeda‐Cota2 and Ana Isabel Valenzuela‐Quintanar2* 1 Biomolecular Medicine, Division of Systems Medicine, Department of Metabolism, Digestion, and Reproduction, Imperial College London, London, United Kingdom. Department of Food Science, Centro de Investigación en Alimentación y Desarrollo, A.C. Hermosillo, Sonora, México; 83004. Tel: +52 (662) 2892400 ext 344. 2 Department of Food Science, Centro de Investigación en Alimentación y Desarrollo, A.C. Hermosillo, Sonora, México; 83004. Tel: +52 (662) 2892400 ext 344. 3 Department of Nutrition, Centro de Investigación en Alimentación y Desarrollo, A.C. Hermosillo, Sonora, México; 83004. Tel: + 52 (662) 2892400 ext 395. * Correspondence: [email protected], Tel: + 52 (662) 2892400 ext 344. Supplement Table 1. Comparison of relevant methods for the quantification of phytoestrogens in food, including matrix (g), system (injection volume), extraction (reconstitution) used, phytoestrogens analysed, limits of detection / limits of quantification (LOD/LOQ, ng/mL), recoveries (RE%), accuracy (%), and inter / intra‐ precision (%) Author, Matrix System Extraction Phytoestrogens LOD/LOQ RE% Accuracy Inter/Intra‐assay year Palma‐ Boiled rice and LC‐DAD‐ESI‐MS SPE (200 µL, Resveratrol 0.025/0.084 44 4 8.36/7.11 Duran et potato (100 mg F‐D) (50 µL) MeOH/mobile Biochanin A 0.006/0.022 74 7 3.13/1.97 al. 2020 phase, 40/60, v/v) Secoisolariciresinol 0.023/0.078 66 6 1.5/2.9 Luteolin 0.009/0.033 20 5 5.53/11.56 Coumestrol 0.003/0.117 88 10 9.83/5.99 Formononetin 0.007/0.023 78 1 7.24/4.08 Daidzein 0.011/0.037 67 12 2.86/6.93 Enterodiol 0.043/0.144 72 18 3.12/5.96 Equol 1.061/3.541 94 6 8.47/6.34 Kaempferol 0.008/0.029 15 9 11.16/13.16 Glycitein 0.212/0.709 92 9 10.91/6.94 Matairesinol 0.012/0.041 87 13 11.21/5.61 Naringenin 0.014/0.041 70 10 4.06/9.19 Quercetin 0.011/0.036 80 8 10.08/11.21 Enterolactone 0.002/0.008 85 8 2.72/5.7 Genistein 0.006/0.021 113 8 0.44/4.44 Kuhnle et Buffer, celery, red LC‐MS/MS SPE (200 µL, 40% Buffer 1 89‐107 al. 2007 cabbage & orange MeOH) biochanin A 1/3 [1] (100 mg F‐D) dadizein 6/13 formononetin 1/1 genistein 4/3 glycitein 4/12 matairesinol 3/3 secoisolariciresinol 4/4 coumestrol 5/9 Milder et Bread (1g, F‐D) LC‐APCI‐MS/MS L‐L (1 mL, 30% Matairesinol 2.4 55‐102 al. 2004 Tea (1mL) (50 µL) MeOH) Secoisolariciresinol 2.3 82‐77 21/33 [2] Vila‐Donat Lentil & other pulses LC‐ESI‐MS/MS SPE (4 mL, MeOH) Daidzein 0.33/1 88‐114 4‐12/0.4‐1 et al. 2015 (1g) (5 µL) Genistein 0.33/1 91‐106 [3] Bioachanin A 0.03/0.01 69‐105 Shim et al. Black, red bean, soy LC‐PDA (3 µL) DMSO (12 mL, 70% Daidzein 0.5/2 mg/100g 94‐104 6‐12/5‐8 2015 [4] bean & soybean MeOH) Glycitein 1/3 mg/100g 91‐94 4‐9/3‐4 paste (1g) Genistein 0.6/2 mg/100g 92‐106 3‐8/3‐5 Angeloni Coffee (2 mL) LC‐ESI‐MS/MS Enzymatic hydrolysis Secoisolariciresinol 2‐5 70‐98 6‐12/2‐7 et al. 2018 (2 µL) (2.5 mL) Matairesinol 3‐10 53‐93 [5] Nørskov et Bread (20‐25 mg) LC‐ESI‐MS/MS SPE (1.6 mL, 25% Secoisolariciresinol 0.246/0.76 85‐99 1‐14 /0.2‐5 al. 2016 (5 µL) ACN) Enterodiol [6] Matairesinol 0.17/0.366 79‐109 Enterolactone ACN; acetonitrile, APCI; atmospheric pressure chemical ionization, DAD; diode‐array detector, DMSO; dimethyl sulfoxide, ESI; electrospray ionization, F‐ D; freeze‐dried, LC; liquid chromatography, L‐L; liquid‐liquid extraction, MeOH; methanol, MS(/MS); mass spectrometry (tandem), PDA; photo diode array detector, SPE; solid‐phase extraction. This table is not exhaustive and relevant information has been included in order to compare with the validated HPLC‐DAD‐ESI‐MS method with previously developed methods. Supplement Table 2. Comparison of relevant methods for the quantification of phytoestrogens in serum, including matrix (g), system (injection volume), extraction (reconstitution) used, phytoestrogens analysed, limits of detection / limits of quantification (LOD/LOQ, ng/mL), recoveries (RE%), accuracy (%), and inter / intra‐ precision (%) Author, Matrix System Extraction Phytoestrogens LOD/LOQ RE% Accuracy Inter/Intra‐ year assay Palma‐ serum, human LC‐DAD‐ESI‐ SPE (200 µL, Resveratrol 0.018/0.06 92 5 9.43/6.67 Duran et al. (1 mL) MS (50 µL) MeOH/mobile Biochanin A 0.002/0.008 77 11 8.5/3.87 2020 phase, 40/60, v/v Secoisolariciresinol 0.008/0.027 99 4 3.73/2.05 Luteolin 0.028/0.096 82 6 10.55/5.92 Coumestrol 0.001/0.003 30 13 14.46/2.33 Formononetin 0.003/0.011 73 12 11.03/3.2 Daidzein 0.042/0.141 102 0.3 11.79/11.31 Enterodiol 0.039/0.133 98 9 6.09/3.73 Equol 0.068/0.227 104 1 4.11/0.88 Kaempferol 0.003/0.012 76 10 14.25/3.9 Glycitein 0.075/0.251 90 12 14.84/2.72 Matairesinol 0.059/0.198 93 1 4.14/1.27 Naringenin 0.005/0.019 84 2 12.21/4.75 Quercetin 0.061/0.206 83 15 14.87/3.18 Enterolactone 0.001/0.003 80 0.5 6.08/5.61 Genistein 0.001/0.006 101 2 14.05/3.74 Grace et al. Serum, LC‐MS/MS (10 SPE (100 µL, 40% Daidzein <0.010 96‐101 3.6/3.7 2003 [7] human (200 µL) MeOH) Enterodiol <0.010 96‐97 3.7/3.2 µL) Equol 0.100 96 3.5/5.6 Glycitein <0.010 94‐96 4.3/5.7 Enterolactone <0.010 98‐101 3.3/2.8 Genistein <0.010 96‐99 3/2.9 Jian et al. Serum, rat LC‐MS/MS (50 L‐L (120 µL, 2% ACN) Biochanin A 0.1 62‐107 2016 [8] (100 µL) µL) Coumestrol 0.7 28‐52 Daidzein 1.4 108‐123 Enterodiol 1.3 75‐94 Equol 1.5 84‐89 Glycitein 3.5 60 Matairesinol 0.6 84‐89 Naringenin 1.5 63‐79 Enterolactone 2.2 73‐91 Genistein 1.3 105‐123 L‐L (80% MeOH) Biochanin A 2 65.6 5 4.5/4.7 Prasain et Serum, LC‐ESI‐MS/MS Coumestrol 77.1 6.1 7.7/8.2 al. 2010 [9] human (200 (10 µL) Formononetin 85.2 2.5 5.6/5.6 µL) Daidzein 82.1 1.1 6.6/6.3 Enterodiol 86.7 7 7.1/7.3 Equol 83.2 4.3 3.7/3.8 Glycitein 86.2 10.3 8.6/9.0 Enterolactone 81.4 5.1 5.6/5.8 Genistein 57.5 4.5 4.9/4.7 Valentin‐ Serum, LC‐APCI‐ SPE (100 µL, 10mM Daidzein 0.5 100.8 <13 9.8 Blasini et al. human, fetal MS/MS (25 µL) ammonium Enterodiol 1.1 90.9 5.1 2000 [10] bovine serum acetate/ACN/MeOH, Equol 2.4 96 13.7 (1 mL) 70/15/15, v/v/v) Matairesinol 0.5 88.2 7.9 Enterolactone 0.1 89.5 4.5 Genistein 0.6 93 19.3 Wyns et al. Serum, LC‐APCI‐MS SPE (100 µL, MeOH) Secoisolariciresinol 132.6 95.8 14.8 15.7/2.8 2010 [11] human (800 (25 & 50 µL) Coumestrol 6.2 19.7 14.4 13.1/9.3 µL) Daidzein 1.9 95.2 4 12.8/2.9 Enterodiol 3.1 95.6 15 11.2/3.2 Equol 13.8 95.5 1.7 11/3.3 Matairesinol 17.8 98 12.9 13.4/2.9 Enterolactone 2.4 95 17.3 10.5/3.2 Genistein 2.2 90.6 3.1 13.7/3.0 Soukup et Plasma, LC‐ESI‐MS/MS SPE (200 µL, 30% Daidzein 0.076/0.25 91 1 5.2/2.6 al. 2014 human (500 (20 µL) MeOH) Equol 9.6/319 88 7 5.1/4.3 [12] µL) Genistein 0.03/0.1 87 3 6.1/3.4 Nørskov et Plasma, LC‐ESI‐MS/MS SPE (600 µL, 25% Secoisolariciresinol /0.067 86.3 2.1 3 al. 2015 human & pig ACN) Enterodiol /0.081 93 4.9 4.2 [13] (500 µL) Matairesinol /0.068 96.5 2.9 2.8 Enterolactone /0.16 101.9 5.9 7.6 Cao et al. Plasma, LC‐DAD (30 SPE (100 µL, Luteolin 0.62‐0.70 97.26 5.77 2010 [14] human (1 mL) µL) MeOH/0.1% Kaempferol 97.31 6.01 Phosphoric acid, Quercetin 104.25 6.84 3/2, v/v) Preindl et Serum, LC‐ESI‐MS/MS Protein precipitation Resveratrol 4.8/16 81 20/36 al.
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