Bioaccessibility and Bioavailability of Soybean Isoflavones: An In Vitro Study

References

• Food and Agriculture Organization (FAO) Online Database, Crops and Livestock Products. Rome, Italy, 2020. (accessed July 28, 2023) https://www.fao.org/faostat/en/#data/QCL.
   Google Scholar
• Zaheer, K.; Akhtar, M. H. An Updated Review of Dietary Isoflavones: Nutrition, Processing, Bioavailability and Impacts on Human Health. Crit. Rev. Food Sci. Nutr. 2017, 57, 1280–1293. DOI: 10.1080/10408398.2014.989958.
   PubMed Web of Science ®Google Scholar
• Liu, H.; Wang, Y.; Zhu, D.; Xu, J.; Xu, X.; Liu, J. Bioaccessibility and Application of Soybean Isoflavones: A Review. Food Rev. Int. in press. DOI: 10.1080/87559129.2022.2103824.
   Google Scholar
• Andres, S.; Hansen, U.; Niemann, B.; Palavinskas, R.; Lampen, A. Determination of the Isoflavone Composition and Estrogenic Activity of Commercial Dietary Supplements Based on Soy or Red Clover. Food Funct. 2015, 6(6), 2017–2025. DOI: 10.1039/c5fo00308c.
   PubMed Web of Science ®Google Scholar
• Hsiao, Y.-H.; Ho, C.-T.; Pan, M.-H. Bioavailability and Health Benefits of Major Isoflavone Aglycones and Their Metabolites. J. Funct. Foods. 2020, 74, 104164. DOI: 10.1016/j.jff.2020.104164.
   Web of Science ®Google Scholar
• Visvanathan, R.; Williamson, G. Review of Factors Affecting Citrus Polyphenol Bioavailability and Their Importance in Designing in Vitro, Animal, and Intervention Studies. Compr. Rev. Food Sci. Food Saf. 2022, 21, 4509–4545. DOI: 10.1111/1541-4337.13057.
   PubMed Web of Science ®Google Scholar
• Aboushanab, S. A.; Khedr, S. M.; Gette, I. F.; Danilova, I. G.; Kolberg, N. A.; Ravishankar, G. A.; Ambati, R. R.; Kovaleva, E. G. Isoflavones Derived from Plant Raw Materials: Bioavailability, Anti-Cancer, Anti-Aging Potentials, and Microbiome Modulation. Crit. Rev. Food Sci. Nutr. 2023, 63, 261–287. DOI: 10.1080/10408398.2021.1946006.
   PubMed Web of Science ®Google Scholar
• Kim, M.-S.; Jung, Y. S.; Jang, D.; Cho, C. H.; Lee, S.-H.; Han, N. S.; Kim, D.-O. Antioxidant Capacity of 12 Major Soybean Isoflavones and Their Bioavailability Under Simulated Digestion and in Human Intestinal Caco-2 Cells. Food Chem. 2022, 374, 131493. DOI: 10.1016/j.foodchem.2021.131493.
   PubMed Web of Science ®Google Scholar
• Nielsen, I. L. F.; Williamson, G. Review of the Factors Affecting Bioavailability of Soy Isoflavones in Humans. Nutr. Cancer. 2007, 57(1), 1–10. DOI: 10.1080/01635580701267677.
   PubMed Web of Science ®Google Scholar
• Larkin, T.; Price, W. E.; Astheimer, L. The Key Importance of Soy Isoflavone Bioavailability to Understanding Health Benefits. Crit. Rev. Food Sci. Nutr. 2008, 48, 538–552. DOI: 10.1080/10408390701542716.
   PubMed Web of Science ®Google Scholar
• Messina, M. Soybean Isoflavone Exposure Does Not Have Feminizing Effects on Men: A Critical Examination of the Clinical Evidence. Fertil. Steril. 2010, 93, 2095–2104. DOI: 10.1016/j.fertnstert.2010.03.002.
   PubMed Web of Science ®Google Scholar
• Xiao, Y.; Zhang, S.; Tong, H.; Shi, S. Comprehensive Evaluation of the Role of Soy and Isoflavone Supplementation in Humans and Animals Over the Past Two Decades. Phytother. Res. 2017, 32, 384–394. DOI: 10.1002/ptr.5966.
   PubMed Web of Science ®Google Scholar
• Hu, C.; Wong, W.-T.; Wu, R.; Lai, W.-F. Biochemistry and Use of Soybean Isoflavones in Functional Food Development. Crit. Rev. Food Sci. Nutr. 2020, 60, 2098–2112. DOI: 10.1080/10408398.2019.1630598.
   PubMed Web of Science ®Google Scholar
• Rizzo, G.; Feraco, A.; Storz, M. A.; Lombardo, M. The Role of Soy and Soy Isoflavones on Women’s Fertility and Related Outcomes: An Update. J. Nutri. Sci. 2022, 11, 1–17. DOI: 10.1017/jns.2022.15.
   Web of Science ®Google Scholar
• Shah, P.; Fritz, J. V.; Glaab, E.; Desai, M. S.; Greenhalgh, K.; Frachet, A.; Niegowska, M.; Estes, M.; Jäger, C.; Seguin-Devaux, C., et al. A Microfluidics-Based In Vitro Model of the Gastrointestinal Human–Microbe Interface. Nat. Commun. 2016, 7, 11535. DOI: 10.1038/ncomms11535.
   PubMed Web of Science ®Google Scholar
• Li, Y.; Kong, F. Simulating Human Gastrointestinal Motility in Dynamic In Vitro Models. Compr. Rev. Food Sci. Food Saf. 2022, 21, 3804–3833. DOI: 10.1111/1541-4337.13007.
   PubMed Web of Science ®Google Scholar
• Mackie, A.; Mulet-Cabero, A.-I.; Torcello-Gómez, A. Simulating Human Digestion: Developing Our Knowledge to Create Healthier and More Sustainable Foods. Food Funct. 2020, 11, 9397. DOI: 10.1039/D0FO01981J.
   PubMed Web of Science ®Google Scholar
• Jung, Y. S.; Rha, C.-S.; Baik, M.-Y.; Baek, N.-I.; Kim, D.-O. A Brief History and Spectroscopic Analysis of Soy Isoflavones. Food Sci. Biotechnol. 2020, 29, 1605–1617. DOI: 10.1007/s10068-020-00815-6.
   PubMed Web of Science ®Google Scholar
• Cho, C.-H.; Jung, Y. S.; Nam, T. G.; Rha, C.-S.; Ko, M.-J.; Jang, D.; Kim, H.-S.; Kim, D.-O. pH-Adjusted Solvent Extraction and Reversed-Phase HPLC Quantification of Isoflavones from Soybean (Glycine Max (L.) Merr.). J. Food Sci. 2020, 85, 673–681. DOI: 10.1111/1750-3841.15051.
   PubMed Web of Science ®Google Scholar
• Lee, S. K.; Row, K. H. Estimation for Retention Factor of Isoflavones in Physico-Chemical Properties. Bull. Korean Chem. Soc. 2003, 24, 1265–1268. DOI: 10.5012/bkcs.2003.24.9.1265.
   Web of Science ®Google Scholar
• Jung, Y. S.; Kim, H.-G.; Oh, S. M.; Lee, D. Y.; Park, C.-S.; Kim, D.-O.; Baek, N.-I. Synthesis of Alpha-Linked Glucosides from Soybean Isoflavone Aglycones Using Amylosucrase from Deinococcus Geothermalis. J. Agric. Food. Chem. 2023, 71, 2430–2437. DOI: 10.1021/acs.jafc.2c07778.
   PubMedGoogle Scholar
• Vacek, J.; Klejdus, B.; Lojková, L.; Kubáň, V. Current Trends in Isolation, Separation, Determination and Identification of Isoflavones: A Review. J. Sep. Sci. 2008, 31, 2051–2067. DOI: 10.1002/jssc.200700569.
   Web of Science ®Google Scholar
• Walsh, K. R.; Zhang, Y. C.; Vodovotz, Y.; Schwartz, S. J.; Failla, M. L. Stability and Bioaccessibility of Isoflavones from Soy Bread During In Vitro Digestion. J. Agric. Food. Chem. 2003, 51, 4603–4609. DOI: 10.1021/jf0342627.
   PubMed Web of Science ®Google Scholar
• Fang, Y.; Cao, W.; Xia, M.; Pan, S.; Xu, X. Study of Structure and Permeability Relationship of Flavonoids in Caco-2 Cells. Nutrients. 2017, 9, 1301. DOI: 10.3390/nu9121301.
   PubMed Web of Science ®Google Scholar
• Murota, K.; Shimizu, S.; Miyamoto, S.; Izumi, T.; Obata, A.; Kikuchi, M.; Terao, J. Unique Uptake and Transport of Isoflavone Aglycones by Human Intestinal Caco-2 Cells: Comparison of Isoflavonoids and Flavonoids. J. Nutr. 2002, 132, 1956–1961. DOI: 10.1093/jn/132.7.1956.
   PubMed Web of Science ®Google Scholar
• Babić, S.; Horvat, A. J. M.; Pavlović, D. M.; Kaštelan-Macan, M. Determination of pKa Values of Active Pharmaceutical Ingredients. TrAC-Trend. Anal. Chem. 2007, 26, 1043–1061. DOI: 10.1016/j.trac.2007.09.004.
   Web of Science ®Google Scholar
• Rodríguez-Roque, M. J.; Rojas-Graü, M. A.; Elez-Martínez, P.; Martín-Belloso, O. Soymilk Phenolic Compounds, Isoflavones and Antioxidant Activity as Affected by In Vitro Gastrointestinal Digestion. Food Chem. 2013, 136, 206–212. DOI: 10.1016/j.foodchem.2012.07.115.
   PubMed Web of Science ®Google Scholar
• Ningtyas, D. W.; Hati, S.; Prakash, S. Bioconversion and Bioaccessibility of Isoflavones from Sogurt During In Vitro Digestion. Food Chem. 2021, 343, 128553. DOI: 10.1016/j.foodchem.2020.128553.
   PubMed Web of Science ®Google Scholar
• Chen, P.; Sun, J.; Liang, Z.; Xu, H.; Du, P.; Li, A.; Meng, Y.; Reshetnik, E. I.; Liu, L.; Li, C. The Bioavailability of Soy Isoflavones In Vitro. Food. Res. Int. 2022, 152, 110868. DOI: 10.1016/j.foodres.2021.110868.
   PubMed Web of Science ®Google Scholar
• Almeida, I.; Rodrigues, F.; Sarmento, B.; Alves, R. C.; Oliveira, M. Isoflavones in Food Supplements: Chemical Profile, Label Accordance and Permeability Study in Caco-2 Cells. Food Funct. 2015, 6, 938–946. DOI: 10.1039/C4FO01144A.
   PubMed Web of Science ®Google Scholar
• de Pascual-Teresa, S.; Hallund, J.; Talbot, D.; Schroot, J.; Williams, C. M.; Bugel, S.; Cassidy, A. Absorption of Isoflavones in Humans: Effects of Food Matrix and Processing. J. NUTR BIOCHEM. 2006, 17, 257–264. DOI: 10.1016/j.jnutbio.2005.04.008.
   PubMed Web of Science ®Google Scholar
• Ji, H.; Hu, J.; Zuo, S.; Zhang, S.; Li, M.; Nie, S. In Vitro Gastrointestinal Digestion and Fermentation Models and Their Applications in Food Carbohydrates. Crit. Rev. Food Sci. Nutr. 2022, 62, 5349–5371. DOI: 10.1080/10408398.2021.1884841.
   PubMed Web of Science ®Google Scholar
• Miller, D. D.; Schricker, B. R.; Rasmussen, R. R.; Campen, D. V. An In Vitro Method for Estimation of Iron Availability from Meals. Am. J. Clin. Nutr. 1981, 34, 2248–2256. DOI: 10.1093/ajcn/34.10.2248.
   PubMed Web of Science ®Google Scholar
• Santana, M. G.; Freitas-Silva, O.; Mariutti, L. R. B.; Teodoro, A. J. A Review of In Vitro Methods to Evaluate the Bioaccessibility of Phenolic Compounds in Tropical Fruits. Crit. Rev. Food Sci. Nutr. in press. DOI: 10.1080/10408398.2022.2119203.
   Web of Science ®Google Scholar
• Minekus, M.; Marie, A.; Alvito, P. C.; Ballance, S.; Bohn, T.; Bourlieu, C.; Carrière, F.; Boutrou, R.; Corredig, M.; Dupont, D., et al. A Standardised Static In Vitro Digestion Method Suitable for Food–An International Consensus. Food Funct. 2014, 5, 1113–1124. DOI: 10.1039/C3FO60702J.
   PubMed Web of Science ®Google Scholar
• Sabet, S.; Kirjoranta, S. J.; Lampi, A.-M.; Lehtonen, M.; Pulkkinen, E.; Valoppi, F. Addressing Criticalities in the INFOGEST Static In Vitro Digestion Protocol for Oleogel Analysis. Food. Res. Int. 2022, 160, 111633. DOI: 10.1016/j.foodres.2022.111633.
   PubMed Web of Science ®Google Scholar
• Brodkorb, A.; Egger, L.; Alminger, M.; Alvito, P.; Assunção, R.; Ballance, S.; Bohn, T.; Bourlieu-Lacanal, C.; Boutrou, R.; Carrière, F., et al. INFOGEST Static In Vitro Simulation of Gastrointestinal Food Digestion. Nat. Protoc. 2019, 14, 991–1014. DOI: 10.1038/s41596-018-0119-1.
   PubMed Web of Science ®Google Scholar
• de Melo, E. L.; Pinto, A. M.; Baima, C. L. B.; da Silva, H. R.; da Silva, I. S.; Sanchez-Ortiz, B. L.; de Lima, A. V. T.; Pereira, A. C. M.; Barbosa, R. S.; Carvalho, H. O., et al. Evaluation of the In Vitro Release of Isoflavones from Soybean Germ Associated with Kefir Culture in the Gastrointestinal Tract and Anxiolytic and Antidepressant Actions in Zebrafish (Danio rerio). J. Funct. Foods. 2020, 70, 103986. doi: 10.1016/j.jff.2020.103986.
   Web of Science ®Google Scholar
• Kiers, J. L.; Nout, R. M. J.; Rombouts, F. M. In Vitro Digestibility of Processed and Fermented Soya Bean, Cowpea and Maize. J. Sci. Food Agric. 2000, 80, 1325–1331. DOI: 10.1002/1097-0010(200007)80:9<1325:AID-JSFA648>3.0.CO;2-K.
   Web of Science ®Google Scholar
• Seok, J. S.; Kim, J. S.; Kwak, H. S. Microencapsulation of Water-Soluble Isoflavone and Physico-Chemical Property in Milk. Arch. Pharm. Res. 2003, 26, 426–431. DOI: 10.1007/BF02976702.
   PubMed Web of Science ®Google Scholar
• Kim, N. C.; Jeon, B. J.; Ahn, J.; Kwak, H. S. In Vitro Study of Microencapsulated Isoflavone and β-Galactosidase. J. Agric. Food. Chem. 2006, 54, 2582–2586. DOI: 10.1021/jf052369j.
   PubMed Web of Science ®Google Scholar
• Sanz, T.; Luyten, H. Release, Partitioning and Stability of Isoflavones from Enriched Custards During Mouth, Stomach and Intestine In Vitro Simulations. Food Hydrocol. 2006, 20, 892–900. DOI: 10.1016/j.foodhyd.2005.09.003.
   Web of Science ®Google Scholar
• Islam, M. A.; Punt, A.; Spenkelink, B.; Murk, A. J.; van Leeuwen, F. X. R.; Rietjens, I. M. C. M. Conversion of Major Soy Isoflavone Glucosides and Aglycones in In Vitro Intestinal Models. Mol. Nutr Food Res. 2014, 58, 503–515. DOI: 10.1002/mnfr.201300390.
   PubMed Web of Science ®Google Scholar
• da Silva Fernandes, M.; Lima, F. S.; Rodrigues, D.; Handa, C.; Guelf, M.; Garcia, S.; Ida, E. I. Evaluation of the Isoflavone and Total Phenolic Contents of Kefir-Fermented Soymilk Storage and After the In Vitro Digestive System Simulation. Food Chem. 2017, 229, 373–380. DOI: 10.1016/j.foodchem.2017.02.095.
   PubMed Web of Science ®Google Scholar
• Wyspiańska, D.; Kucharska, A. Z.; Sokół-Łętowska, A.; Kolniak-Ostek, J. Effect of Microencapsulation on Concentration of Isoflavones During Simulated In Vitro Digestion of Isotonic Drink. Food Sci. Nutr. 2019, 7, 805–816. DOI: 10.1002/fsn3.929.
   PubMed Web of Science ®Google Scholar
• Rodríguez-Roque, M. J.; Ancos, B. D.; Sánchez-Vega, R.; Sánchez-Moreno, C.; Elez-Martínez, P.; Martín-Belloso, O. In Vitro Bioaccessibility of Isoflavones from a Soymilk-Based Beverage as Affected by Thermal and Non-Thermal Processing. Innov. Food Sci. Emerg. Technol. 2020, 66, 102504. DOI: 10.1016/j.ifset.2020.102504.
   Web of Science ®Google Scholar
• de Queirós, L. D.; Dias, F. F. G.; de Ávila, A. R. A.; Macedo, J. A.; Macedo, G. A.; de Moura, M. L. N. B. Effects of Enzyme-Assisted Extraction on the Profile and Bioaccessibility of Isoflavones from Soybean Flour. Food. Res. Int. 2021, 147, 110474. DOI: 10.1016/j.foodres.2021.110474.
   PubMed Web of Science ®Google Scholar
• Mosele, J. I.; Macià, A.; Romero, M.-P.; Motilva, M.-J.; Rubió, L. Application of In Vitro Gastrointestinal Digestion and Colonic Fermentation Models to Pomegranate Products (Juice, Pulp and Peel Extract) to Study the Stability and Catabolism of Phenolic Compounds. J. Funct. Foods. 2015, 14, 529–540. DOI: 10.1016/j.jff.2015.02.026.
   Web of Science ®Google Scholar
• Kong, F.; Singh, R. P. A Human Gastric Simulator (HGS) to Study Food Digestion in Human Stomach. J. Food Sci. 2010, 75, E627–E635. DOI: 10.1111/j.1750-3841.2010.01856.x.
   PubMed Web of Science ®Google Scholar
• Alminger, M.; Aura, A.-M.; Bohn, T.; Dufour, C.; El, S. N.; Gomes, A.; Karakaya, S.; Martínez-Cuesta, M. C.; Mcdougall, G. J.; Requena, T., et al. In Vitro Models for Studying Secondary Plant Metabolite Digestion and Bioaccessibility. Compr. Rev. Food Sci. Food Saf. 2014, 13, 413–436. DOI: 10.1111/1541-4337.12081.
   PubMed Web of Science ®Google Scholar
• Laurent, C.; Besançon, P.; Caporiccio, B. Flavonoids from a Grape Seed Extract Interact with Digestive Secretions and Intestinal Cells as Assessed in an In Vitro Digestion/caco-2 Cell Culture Model. Food Chem. 2007, 100, 1704–1712. DOI: 10.1016/j.foodchem.2005.10.016.
   Web of Science ®Google Scholar
• Velickovic, T. D. C.; Stanic-Vucinic, D. J. The Role of Dietary Phenolic Compounds in Protein Digestion and Processing Technologies to Improve Their Antinutritive Properties. Compr. Rev. Food Sci. Food Saf. 2018, 17, 82–103. DOI: 10.1111/1541-4337.12320.
   PubMed Web of Science ®Google Scholar
• Perez-Gregorio, M. R.; Días, R.; Mateusa, N.; de Freitas, V. Identification and Characterization of Proteolytically Resistant Gluten-Derived Peptides. Food Funct. 2018, 9, 1726–1735. DOI: 10.1039/C7FO02027A.
   PubMed Web of Science ®Google Scholar
• Sy, C.; Gleize, B.; Dangles, O.; Landrier, J. F.; Veyrat, C. C.; Borel, P. Effects of Physicochemical Properties of Carotenoids on Their Bioaccessibility, Intestinal Cell Uptake, and Blood and Tissue Concentrations. Mol. Nutr Food Res. 2012, 56, 1385–1397. DOI: 10.1002/mnfr.201200041.
   PubMed Web of Science ®Google Scholar
• Kobayashi, S.; Shinohara, M.; Nagai, T.; Konishi, Y. Transport Mechanisms for Soy Isoflavones and Microbial Metabolites Dihydrogenistein and Dihydrodaidzein Across Monolayers and Membranes. Biosci. Biotechnol., Biochem. 2013, 77, 2210–2217. DOI: 10.1271/bbb.130404.
   PubMed Web of Science ®Google Scholar
• Osakwe, O. Social Aspects of Drug Discovery, Development and Commercialization. In Preclinical in vitro Studies: Development and Applicability, Osakwe, O. and Rizvi, S., Eds.; Academic Press:London, UK, 2016; pp. 129–148. DOI:10.1016/B978-0-12-802220-7.00006-5.
   Google Scholar
• Rao, A. L.; Sankar, G. G. Caco-2 Cells: An Overview. Asian J. Pharmaceut. Res. Health Care. 2009, 1, 260–275.
   Google Scholar
• Lea, T. The Impact of Food Bioactives on Gut Health. In Caco-2 Cell Line, Verhoeckx, K., Ed.; Springer International Publishing AG:Cham, Switzerland, 2015; pp. 103–111. doi:10.1007/978-3-319-16104-4_10.
   Google Scholar
• Oitate, M.; Nakaki, R.; Koyabu, N.; Takanaga, H.; Matsuo, H.; Ohtani, H.; Sawada, Y. Transcellular Transport of Genistein, a Soybean-Derived Isoflavone, Across Human Colon Carcinoma Cell Line. Biopharm. Drug Dispos. 2001, 22, 23–29. DOI: 10.1002/bdd.253.
   PubMed Web of Science ®Google Scholar
• Hubatsch, I.; Ragnarsson, E. G. E.; Artursson, P. Determination of Drug Permeability and Prediction of Drug Absorption in Caco-2 Monolayers. Nat. Protoc. 2007, 2, 2111–2119. DOI: 10.1038/nprot.2007.303.
   PubMed Web of Science ®Google Scholar
• Gonzales, G. B.; Smagghe, G.; Grootaert, C.; Zotti, M.; Raes, K.; van Camp, J. Flavonoid Interactions During Digestion, Absorption, Distribution and Metabolism: A Sequential Structure–Activity/property Relationship-Based Approach in the Study of Bioavailability and Bioactivity. Drug Metab. Rev. 2015, 47, 175–190. DOI: 10.3109/03602532.2014.1003649.
   PubMed Web of Science ®Google Scholar
• Steensma, A.; Noteborn, H. P. J. M.; Kuipera, H. A. Comparison of Caco-2, IEC-18 and HCEC Cell Lines as a Model for Intestinal Absorption of Genistein, Daidzein and Their Glycosides. Environ. Toxicol. Pharmacol. 2004, 16, 131–139. DOI: 10.1016/j.etap.2003.11.008.
   PubMed Web of Science ®Google Scholar
• Srinivasan, B.; Kolli, A. R.; Esch, M. B.; Abaci, H. E.; Shuler, M. L.; Hickman, J. J. TEER Measurement Techniques for In Vitro Barrier Model Systems. J. Lab. Autom. 2015, 20, 107–126. DOI: 10.1177/2211068214561025.
   PubMedGoogle Scholar
• Toro-Funes, N.; Morales-Gutiérrez, F. J.; Veciana-Nogués, M. T.; Vidal-Carou, M. C.; Spencer, J. P. E.; Rodriguez-Mateos, A. The Intracellular Metabolism of Isoflavones in Endothelial Cells. Food Funct. 2015, 6, 98–108. DOI: 10.1039/c4fo00772g.
   PubMed Web of Science ®Google Scholar
• Fang, Y.; Liang, F.; Liu, K.; Qaiser, S.; Pan, S.; Xu, X. Structure Characteristics for Intestinal Uptake of Flavonoids in Caco-2 Cells. Food. Res. Int. 2018, 105, 335–360. DOI: 10.1016/j.foodres.2017.11.045.
   Web of Science ®Google Scholar
• Wang, J.; Han, C.; Ta, W.; Liu, R.; He, X.; Lu, W. Development a Multicellular Model to Investigate the Intestinal-Vascular Transport Barrier of Drug. J. Drug Deliv. Sci. Technol. 2021, 62, 102366. DOI: 10.1016/j.jddst.2021.102366.
   Web of Science ®Google Scholar
• Steensma, A.; Mengelers, M. J. B.; Noteborn, H. P. J. M.; Kuiper, H. A. Kinetic Models Describing In Vitro Transport and Metabolism of Isoflavones and Their Glycosides in Human Caco-2 Cells. In Dietary Anticarcinogens and Antimutagens: Chemical and Biological Aspects, Johnson, I.T. and Fenwick, G.R., Eds.; Elsevier Science:Amsterdam, Netherlands, 2000; pp. 58–63. DOI:10.1533/9781845698188.2.58.
   Google Scholar
• Liu, Y.; Hu, M. Absorption and Metabolism of Flavonoids in the Caco-2 Cell Culture Model and a Perused Rat Intestinal Model. Drug Metab. Dispos. 2002, 30, 370–377. DOI: 10.1124/dmd.30.4.370.
   PubMed Web of Science ®Google Scholar
• Chen, J.; Lin, H.; Hu, M. Absorption and Metabolism of Genistein and Its Five Isoflavone Analogs in the Human Intestinal Caco-2 Model. Cancer Chemother. Pharmacol. 2005, 55, 159–169. DOI: 10.1007/s00280-004-0842-x.
   PubMed Web of Science ®Google Scholar
• Daruházia, Á. E.; Kiss, T.; Vecsernyés, M.; Szentec, L.; Szőkea, É.; Lemberkovics, É. Investigation of Transport of Genistein, Daidzein and Their Inclusion Complexes Prepared with Different Cyclodextrins on Caco-2 Cell Line. J. Pharm. Biomed. Anal. 2013, 84, 113–116. DOI: 10.1016/j.jpba.2013.05.012.
   Web of Science ®Google Scholar
• Papaj, K.; Rusin, A.; Szeja, W.; Grynkiewicz, G. Absorption and Metabolism of Biologically Active Genistein Derivatives in Colon Carcinoma Cell Line (Caco-2). Acta. Pol. Pharm-Drug Res. 2014, 71, 1037–1044. https://pubmed.ncbi.nlm.nih.gov/25745776.
   PubMed Web of Science ®Google Scholar
• Papaj, K.; Kasprzycka, A.; Góra, A.; Grajoszek, A.; Rzepecka, G.; Stojko, J.; Barski, J.-J.; Szeja, W.; Rusin, A. Structure–Bioavailability Relationship Study of Genistein Derivatives with Antiproliferative Activity on Human Cancer Cell. J. Pharm. Biomed. Anal. 2020, 185, 113216. DOI: 10.1016/j.jpba.2020.113216.
   PubMed Web of Science ®Google Scholar
• Kawahara, I.; Nishikawa, S.; Yamamoto, A.; Kono, Y.; Fujita, T. The Impact of Breast Cancer Resistance Protein (BCRP/ABCG2) on Drug Transport Across Caco-2 Cell Monolayers. Drug Metab. Dispos. 2000, 48, 491–498. DOI: 10.1124/dmd.119.088674.
   Google Scholar
• Rani, D.; Vimolmangkang, S. Trends in the Biotechnological Production of Isoflavonoids in Plant Cell Suspension Cultures. Phytochem Rev. 2022, 21, 1843–1862. DOI: 10.1007/s11101-022-09811-6.
   Web of Science ®Google Scholar
• Wells, C. L.; Jechorek, R. P.; Kinneberg, K. M.; Debol, S. M.; Erlandsen, S. L. The Isoflavone Genistein Inhibits Internalization of Enteric Bacteria by Cultured Caco-2 and HT-29 Enterocytes. J. Nutr. 1999, 129, 634–640. DOI: 10.1093/jn/129.3.634.
   PubMed Web of Science ®Google Scholar
• Rostagno, M. A.; Palma, M.; Barroso, C. G. Short-Term Stability of Soy Isoflavones Extracts: Sample Conservation Aspects. Food Chem. 2005, 93, 557–564. DOI: 10.1016/j.foodchem.2004.12.035.
   Web of Science ®Google Scholar
• Vilela, D.; González, M. C.; Escarpa, A. (Bio)-Synthesis of Au NPs from Soy Isoflavone Extracts as a Novel Assessment Tool of Their Antioxidant Capacity. R.S.C. Adv. 2014, 4, 3075–3081. DOI: 10.1039/c3ra45180a.
   Web of Science ®Google Scholar
• Walgren, R. A.; Lin, J.-T.; Kinne, R. K.-H.; Walle, T. Cellular Uptake of Dietary Flavonoid Quercetin 4′-β-Glucoside by Sodium-Dependent Glucose Transporter SGLT1. J. Pharmacol. Exp. Ther. 2000, 294, 837–843.
   PubMed Web of Science ®Google Scholar
• Ding, X.; Hu, X.; Chen, Y.; Xie, J.; Ying, M.; Wang, Y.; Yu, Q. Differentiated Caco-2 Cell Models in Food-Intestine Interaction Study: Current Applications and Future Trends. Trends Food Sci. Technol. 2021, 107, 455–465. DOI: 10.1016/j.tifs.2020.11.015.
   Web of Science ®Google Scholar
• Sekine, T.; Cha, S. H.; Endou, H. The Multispecific Organic Anion Transporter (OAT) Family. Pflugers Arch. 2000, 440, 337–350. DOI: 10.1007/s004240000297.
   PubMed Web of Science ®Google Scholar
• King, R. A.; Bursill, D. B. Plasma and Urinary Kinetics of the Isoflavones Daidzein and Genistein After a Single Soy Meal in Humans. Am. J. Clin. Nutr. 1998, 67, 867–872. DOI: 10.1093/ajcn/67.5.867.
   PubMed Web of Science ®Google Scholar
• Setchell, K. D. R.; Brown, N. M.; Desai, P.; Zimmer-Nechemias, L.; Wolfe, B. E.; Brashear, W. T.; Kirschner, A. S.; Cassidy, A.; Heubi, J. E. Bioavailability of Pure Isoflavones in Healthy Humans and Analysis of Commercial Soy Isoflavone Supplements. J. Nutr. 2001, 131, 1362S–1375S. DOI: 10.1093/jn/131.4.1362S.
   PubMed Web of Science ®Google Scholar