[1] Yang, X.; Jiang, Y.; Yang, J.; He, J.; Sun, J.; Chen, F.; Zhang, M.; Yang, B. Prenylated flavonoids, promising nutraceuticals with impressive biological activities. Trends Food Sci. Technol. 2015, 44 (1), 93–104.
[2] Gonzales, G. B.; Smagghe, G.; Grootaert, C.; Zotti, M.; Raes, K.; Camp, J. Van. 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 (2), 175–190.
[3] Boozari, M.; Soltani, S.; Iranshahi, M. Biologically active prenylated flavonoids from the genus sophora and their structure–activity relationship-a review. Phyther. Res. 2019, 33 (3), 546–560.
[4] Bamji, S. F.; Corbitt, C. Glyceollins: soybean phytoalexins that exhibit a wide range of health-promoting effects. J. Funct. Foods 2017, 34, 98–105.
[5] Yoneyama, K.; Akashi, T.; Aoki, T. Molecular characterization of soybean pterocarpan 2-dimethylallyltransferase in glyceollin biosynthesis: local gene and whole-genome duplications of prenyltransferase genes led to the structural diversity of soybean prenylated isoflavonoids. Plant Cell Physiol. 2016, 57 (12), 2497–2509.
[6] Van De Schans, M. G. M.; Bovee, T. F. H.; Stoopen, G. M.; Lorist, M.; Gruppen, H.; Vincken, J. P. Prenylation and backbone structure of flavonoids and isoflavonoids from licorice and hop influence their phase I and II metabolism. J. Agric. Food Chem. 2015, 63 (49), 10628–10640.
[7] Pham, T. H.; Lecomte, S.; Efstathiou, T.; Ferriere, F.; Pakdel, F. An update on the effects of glyceollins on human health: possible anticancer effects and underlying mechanisms. Nutrients 2019, 11 (1), 79–103.
[8] Simons, R.; Vincken, J. P.; Roidos, N.; Bovee, T. F. H.; Van Iersel, M.; Verbruggen, M. A.; Gruppen, H. Increasing soy isoflavonoid content and diversity by simultaneous malting and challenging by a fungus to modulate estrogenicity. J. Agric. Food Chem. 2011, 59 (12), 6748–6758.
[9] Wang, K.; Peng, Q.; Qiao, Y.; Li, Y.; Suo, D.; Shi, B. Different glyceollin synthesis- related metabolic content and gene expressions in soybean callus suspension cultures and cotyledon tissues induced by alginate oligosaccharides. Process Biochem. 2018, 73 (7), 188–196.
[10] Kim, H. J.; Suh, H. J.; Kim, J. H.; Park, S.; Joo, Y. C.; Kim, J. S. Antioxidant activity of glyceollins derived from soybean elicited with Aspergillus sojae. J. Agric. Food Chem. 2010, 58 (22), 11633–11638.
[11] Boué, S. M.; Isakova, I. A.; Burow, M. E.; Cao, H.; Bhatnagar, D.; Sarver, J. G.; Shinde, K. V.; Erhardt, P. W.; Heiman, M. L. Glyceollins, soy isoflavone phytoalexins, improve oral glucose disposal by stimulating glucose uptake. J. Agric. Food Chem. 2012, 60 (25), 6376–6382.
[12] Kim, H. J.; Sung, M. K.; Kim, J. S. Anti-inflammatory effects of glyceollins derived from soybean by elicitation with Aspergillus sojae. Inflamm. Res. 2011, 60 (10), 909–917.
[13] Zimmermann, M. C.; Tilghman, S. L.; Boué, S. M.; Salvo, V. A.; Elliott, S.; Williams, K. Y.; Skripnikova, E. V.; Ashe, H.; Payton-Stewart, F.; Vanhoy-Rhodes, L.; Fonseca, J. P.; Corbitt, C.; Collins-Burow, B. M.; Howell, M. H.; Lacey, M.; Shih, B. Y.; Carter-Wientjes, C.; Cleveland, T. E.; McLachlan, J. A.; Wiese, T. E.; Beckman, B. S.; Burow, M. E. Glyceollin I, a novel antiestrogenic phytoalexin isolated from activated soy. J. Pharmacol. Exp. Ther. 2010, 332 (1), 35–45.
[14] Bamji, S. F.; Rouchka, E.; Zhang, Y.; Li, X.; Kalbfleisch, T.; Corbitt, C. Next generation sequencing analysis of soy glyceollins and 17-β estradiol: effects on transcript abundance in the female mouse brain. Mol. Cell. Endocrinol. 2018, 471, 15–21.
[15] Burow, M. E.; Boue, S. M.; Collins-Burow, B. M.; Melnik, L. I.; Duong, B. N.; Carter-Wientjes, C. H.; Li, S.; Wiese, T. E.; Cleveland, T. E.; Mclachlan, J. A. Phytochemical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor α and β. J. Clin. Endocrinol. Metab. 2001, 86 (4), 1750–1758.
[16] Nikov, G. N.; Hopkins, N. E.; Boue, S.; Alworth, W. L. Interactions of dietary estrogens with human estrogen receptors and the effect on estrogen receptor-estrogen response element complex formation. Environ. Health Perspect. 2000, 108 (9), 867–872.
[17] Yamamoto, T.; Sakamoto, C.; Tachiwana, H.; Kumabe, M.; Matsui, T.; Yamashita, T.; Shinagawa, M.; Ochiai, K.; Saitoh, N.; Nakao, M. Endocrine therapy-resistant breast cancer model cells are inhibited by soybean glyceollin I through eleanor non- coding RNA. Sci. Rep. 2018, 8 (1), 1–12.
[18] Farrell, K.; Jahan, M. A.; Kovinich, N. Distinct mechanisms of biotic and chemical elicitors enable additive elicitation of the anticancer phytoalexin glyceollin I. Molecules 2017, 22 (8),1261–1274.
[19] Seo, J. Y.; Kim, B. R.; Oh, J.; Kim, J. S. Soybean-derived phytoalexins improve cognitive function through activation of Nrf2/HO-1 signaling pathway. Int. J. Mol. Sci. 2018, 19 (1), 1–12.
[20] Bamji, S. F.; Page, R. B.; Patel, D.; Sanders, A.; Alvarez, A. R.; Gambrell, C.; Naik, K.; Raghavan, A. M.; Burow, M. E.; Boue, S. M.; Klinge, C. M.; Ivanova, M.; Corbitt, C. Soy glyceollins regulate transcript abundance in the female mouse brain. Funct. Integr. Genomics 2015, 15 (5), 549–561.
[21] Yoon, E. K.; Kim, H. K.; Cui, S.; Kim, Y. H.; Lee, S. H. Soybean glyceollins mitigate inducible nitric oxide synthase and cyclooxygenase-2 expression levels via suppression of the NF-ΚB signaling pathway in RAW 264.7 cells. Int. J. Mol. Med. 2012, 29 (4), 711–717.
[22] Lee, W.; Ku, S. K.; Lee, Y. M.; Bae, J. S. Anti-septic effects of glyceollins in HMGB1-induced inflammatory responses in vitro and in vivo. Food Chem. Toxicol. 2014, 63, 1–8.
[23] Kim, H. J.; Cha, B. Y.; Choi, B.; Lim, J. S.; Woo, J. T.; Kim, J. S. Glyceollins inhibit platelet-derived growth factor-mediated human arterial smooth muscle cell proliferation and migration. Br. J. Nutr. 2012, 107 (1), 24–35.
[24] Song, M. J.; Baek, I.; Jeon, S. B.; Seo, M.; Kim, Y. H.; Cui, S.; Jeong, Y. S.; Lee, I. J.; Shin, D. H.; Hwang, Y. H.; Kim, I. K. Effects of glyceollin I on vascular contraction in rat aorta. Naunyn. Schmiedebergs. Arch. Pharmacol. 2010, 381 (6), 517–528.
[25] Lee, Y. S.; Kim, H. K.; Lee, K. J.; Jeon, H. W.; Cui, S.; Lee, Y. M.; Moon, B. J.; Kim, Y. H.; Lee, Y. S. Inhibitory effect of glyceollin isolated from soybean against melanogenesis in B16 melanoma cells. BMB Rep. 2010, 43 (7), 461–467.
[26] Shin, S. H.; Lee, Y. M. Glyceollins, a novel class of soybean phytoalexins, inhibit SCF-induced melanogenesis through attenuation of SCF/c-Kit downstream signaling pathways. Exp. Mol. Med. 2013, 45 (2), 1–9.
[27] Bateman, M. E.; Strong, A. L.; Hunter, R. S.; Bratton, M. R.; Komati, R.; Sridhar, J.; Riley, K. E.; Wang, G.; Hayes, D. J.; Boue, S. M.; Burow, M. E.; Bunnell, B. A. Osteoinductive effects of glyceollins on adult mesenchymal stromal/stem cells from adipose tissue and bone marrow. Phytomedicine 2017, 27, 39–51.
[28] Park, S.; Ahn, I. S.; Kim, J. H.; Lee, M. R.; Kim, J. S.; Kim, H. J. Glyceollins, one of the phytoalexins derived from soybeans under fungal stress, enhance insulin sensitivity and exert lnsulinotropic actions. J. Agric. Food Chem. 2010, 58 (3), 1551–1557.
[29] Park, S.; Kim, D. S.; Kim, J. H.; Kim, J. S.; Kim, H. J. Glyceollin-containing fermented soybeans improve glucose homeostasis in diabetic mice. Nutrition 2012, 28 (2), 204–211.
[30] Huang, H.; Xie, Z.; Boue, S. M.; Bhatnagar, D.; Yokoyama, W.; Yu, L.; Wang, T. T. Y. Cholesterol-lowering activity of soy-derived glyceollins in the golden syrian hamster model. J. Agric. Food Chem. 2013, 61 (24), 5772–5782.
[31] Wood, C. E.; Boue, S. M.; Collins-Burow, B. M.; Rhodes, L. V.; Register, T. C.; Cline, J. M.; Dewi, F. N.; Burow, M. E. Glyceollin-elicited soy protein consumption induces distinct transcriptional effects as compared to standard soy protein. J. Agric. Food Chem. 2012, 60 (1), 81–86.
[32] Kim, H. J.; di Luccio, E.; Kong, A. N. T.; Kim, J. S. Nrf2-mediated induction of phase II detoxifying enzymes by glyceollins derived from soybean exposed to Aspergillus sojae. Biotechnol. J. 2011, 6 (5), 525–536.
[33] Kim, B. R.; Seo, J. Y.; Sung, M. K.; Park, J. H. Y.; Suh, H. J.; Liu, K. H.; Kim, J. S. Suppression of 7,12-dimethylbenz(a)anthracene-induced mammary tumorigenesis by glyceollins. Mol. Nutr. Food Res. 2015, 59 (5), 907–917.
[34] Kretzschmar, G.; Zierau, O.; Wober, J.; Tischer, S.; Metz, P.; Vollmer, G. Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein. J. Steroid Biochem. Mol. Biol. 2010, 118, 1–6.
[35] Mukai, R.; Fujikura, Y.; Murota, K.; Uehara, M.; Minekawa, S.; Matsui, N.; Kawamura, T.; Nemoto, H.; Terao, J. Prenylation enhances quercetin uptake and reduces efflux in caco-2 cells and enhances tissue accumulation in mice fed long- term. J. Nutr. 2013, 143 (10), 1558–1564.
[36] Terao, J.; Mukai, R. Prenylation modulates the bioavailability and bioaccumulation of dietary flavonoids. Arch. Biochem. Biophys. 2014, 559, 12–16.
[37] Gu, L.; Laly, M.; Chang, H. C.; Prior, R. L.; Fang, N.; Ronis, M. J. J.; Badger, T. M. Isoflavone conjugates are underestimated in tissues using enzymatic hydrolysis. J. Agric. Food Chem. 2005, 53 (17), 6858–6863.
[38] Chang, H. C.; Churchwell, M. I.; Delclos, K. B.; Newbold, R. R.; Doerge, D. R. Mass spectrometric determination of genistein tissue distribution diet-exposed Sprague-Dawley rats. J. Nutr. 2000, 130 (8), 1963–1970.
[39] Soucy, N. V.; Parkinson, H. D.; Sochaski, M. A.; Borghoff, S. J. Kinetics of genistein and its conjugated metabolites in pregnant Sprague-Dawley rats following single and repeated genistein administration. Toxicol. Sci. 2006, 90 (1), 230–240.
[40] Liu, C. S.; Chen, L.; Hu, Y. N.; Dai, J. L.; Ma, B.; Tang, Q. F.; Tan, X. M. Self-microemulsifying drug delivery system for improved oral delivery and hypnotic efficacy of ferulic acid. Int. J. Nanomedicine 2020, 15, 2059–2070.
[41] Chen, X. Q.; Wei, L. T.; Pu, X. P.; Wang, Y. L.; Xu, Y. J. Pharmacokinetics and tissue distribution study of 15 ingredients of polygonum chinense linn extract in rats by UHPLC–MS/MS. Biomed. Chromatogr.2021, 35(2), 4975-4989.
[42] Shi, X.; Tang, Y.; Zhu, H.; Li, W.; Li, Z.; Li, W.; Duan, J. ao. Comparative tissue distribution profiles of five major bio-active components in normal and blood deficiency rats after oral administration of danggui buxue decoction by UPLC- TQ/MS. J. Pharm. Biomed. Anal. 2014, 88, 207–215.
[43] Li, S. Y.; Pei, W. H.; Guo, T.; Zhang, H. Distributions of eight bioactive components in rat tissues administered marsdenia tenacissima extract orally detected through UPLC–MS/MS. Biomed. Chromatogr. 2021, 35 (4), 1–15.
[44] Zeng, X.; Su, W.; Zheng, Y.; He, Y.; He, Y.; Rao, H.; Peng, W.; Yao, H. Pharmacokinetics, tissue distribution, metabolism, and excretion of naringin in aged rats. Front. Pharmacol. 2019, 9 (1), 1–12.
[45] Chen, X.; Zhu, P.; Liu, B.; Wei, L.; Xu, Y. Simultaneous determination of fourteen compounds of hedyotis diffusa willd extract in rats by UHPLC–MS/MS method: application to pharmacokinetics and tissue distribution study. J. Pharm. Biomed. Anal. 2018, 159, 490–512.
[46] Prasain, J. K.; Wang, C. C.; Barnes, S. Mass spectrometric methods for the determination of flavonoids in biological samples. Free Radic. Biol. Med. 2004, 37 (9), 1324–1350.
[47] Mukai, R.; Horikawa, H.; Fujikura, Y.; Kawamura, T.; Nemoto, H.; Nikawa, T.; Terao, J. Prevention of disuse muscle atrophy by dietary ingestion of 8- prenylnaringenin in denervated mice. PLoS One 2012, 7 (9), 1–11.
[48] Arung, E. T.; Shimizu, K.; Tanaka, H.; Kondo, R. 3-Prenyl luteolin, a new prenylated flavone with melanin biosynthesis inhibitory activity from wood of artocarpus heterop. Fitoterapia 2010, 81 (6), 640–643.
[49] Wood, C. E.; Clarkson, T. B.; Appt, S. E.; Franke, A. A.; Boue, S. M.; Burow, M. E.; McCoy, T.; Cline, J. M. Effects of soybean glyceollins and estradiol in postmenopausal female monkeys. Nutr. Cancer 2006, 56 (1), 74–81.
[50] Lo, Y. L. Relationships between the hydrophilic-lipophilic balance values of pharmaceutical excipients and their multidrug resistance modulating effect in Caco- 2 cells and rat intestines. J. Control. Release 2003, 90 (1), 37–48.
[51] 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.
[52] Chimezie, C.; Ewing, A.; Schexnayder, C.; Bratton, M.; Glotser, E.; Skripnikova, E.; Sá, P.; Boué, S.; Stratford, R. E. Glyceollin effects on MRP2 and BCRP in Caco-2 cells, and implications for metabolic and transport interactions. J. Pharm. Sci. 2016, 105 (2), 972–981.
[53] Schexnayder, C.; Stratford, R. E. Genistein and glyceollin effects on ABCC2 (MRP2) and ABCG2 (BCRP) in Caco-2 cells. Int. J. Environ. Res. Public Health 2015, 13 (1), 17–30.
[54] Demeule, M.; Régina, A.; Jodoin, J.; Laplante, A.; Dagenais, C.; Berthelet, F.; Moghrabi, A.; Béliveau, R. Drug transport to the brain: key roles for the efflux pump P-glycoprotein in the blood-brain barrier. Vasc. Pharmacol. 2002, 38 (6), 339–348.
[55] Drennen, C.; Gorse, E.; Stratford, R. E. Cellular pharmacokinetic model-based analysis of genistein, glyceollin, and MK-571 effects on 5 (and 6)-carboxy-2′,7′- dichloroflourescein disposition in Caco-2 cells. J. Pharm. Sci. 2018, 107 (4), 1194–1203.
[56] Zhang, J.; Guo, Q.; Wei, M.; Bai, J.; Huang, J.; Liu, Y.; Su, Z.; Qiu, X. Metabolite identification and pharmacokinetic profiling of isoflavones from black soybean in rats using ultrahigh-performance liquid chromatography with linear-ion-trap-orbitrap and triple-quadrupole tandem mass spectrometry. J. Agric. Food Chem. 2018, 66 (49), 12941–12952.
[57] Barnes, S.; Prasain, J.; D’Alessandro, T.; Arabshahi, A.; Botting, N.; Lila, M. A.; Jackson, G.; Janle, E. M.; Weaver, C. M. The metabolism and analysis of isoflavones and other dietary polyphenols in foods and biological systems. Food Funct. 2011, 2 (5), 235–244.
[58] Legette, L. L.; Prasain, J.; King, J.; Arabshahi, A.; Barnes, S.; Weaver, C. M. Pharmacokinetics of equol, a soy isoflavone metabolite, changes with the form of equol (dietary versus intestinal production) in ovariectomized rats. J. Agric. Food Chem. 2014, 62 (6), 1294–1300.
[59] Houghton, M. J.; Kerimi, A.; Mouly, V.; Tumova, S.; Williamson, G. Gut microbiome catabolites as novel modulators of muscle cell glucose metabolism. FASEB J. 2019, 33 (2), 1887–1898.
[60] Van Rymenant, E.; Van Camp, J.; Pauwels, B.; Boydens, C.; Vanden Daele, L.; Beerens, K.; Brouckaert, P.; Smagghe, G.; Kerimi, A.; Williamson, G.; Grootaert, C.; Van de Voorde, J. Ferulic acid-4-O-sulfate rather than ferulic acid relaxes arteries and lowers blood pressure in mice. J. Nutr. Biochem. 2017, 44, 44–51.
[61] Gu, L.; Laly, M.; Chang, H. C.; Prior, R. L.; Fang, N.; Ronis, M. J. J.; Badger, T. M. Isoflavone conjugates are underestimated in tissues using enzymatic hydrolysis. J. Agric. Food Chem. 2005, 53 (17), 6858–6863.
[62] Chang, H. C.; Churchwell, M. I.; Delclos, K. B.; Newbold, R. R.; Doerge, D. R. Mass spectrometric determination of genistein tissue distribution diet-exposed Sprague-Dawley rats. J. Nutr. 2000, 130 (8), 1963–1970.
[63] Soucy, N. V.; Parkinson, H. D.; Sochaski, M. A.; Borghoff, S. J. Kinetics of genistein and its conjugated metabolites in pregnant Sprague-Dawley rats following single and repeated genistein administration. Toxicol. Sci. 2006, 90 (1), 230–240.
[64] Urpi-Sarda, M.; Morand, C.; Besson, C.; Kraft, G.; Viala, D.; Scalbert, A.; Besle, J. M.; Manach, C. Tissue distribution of isoflavones in ewes after consumption of red clover silage. Arch. Biochem. Biophys. 2008, 476 (2), 205–210.
[65] Domínguez-Avila, J. A.; Wall-Medrano, A.; Velderrain-Rodríguez, G. R.; Chen, C. Y. O.; Salazar-López, N. J.; Robles-Sánchez, M.; González-Aguilar, G. A. Gastrointestinal interactions, absorption, splanchnic metabolism and pharmacokinetics of orally ingested phenolic compounds. Food Funct. 2017, 8 (1), 15–38.
[66] Simmons, A. L.; Chitchumroonchokchai, C.; Vodovotz, Y.; Failla, M. L. Isoflavone retention during processing, bioaccessibility, and transport by Caco-2 cells: effects of source and amount of fat in a soy soft pretzel. J. Agric. Food Chem. 2012, 60 (49), 12196–12203.
[67] Liu, Y.; Hu, M. Absorption and metabolism of flavonoids in the Caco-2 cell culture model and a perfused rat intestinal model. Drug Metab. Dispos. 2002, 30 (4), 370– 377.
[68] Miyake, M.; Kondo, S.; Koga, T.; Yoda, N.; Nakazato, S.; Emoto, C.; Mukai, T.; Toguchi, H. Evaluation of intestinal metabolism and absorption using the Ussing chamber system equipped with intestinal tissue from rats and dogs. Eur. J. Pharm. Biopharm. 2018, 122 (2), 49–53.
[69] Nguyen, H. N.; Tanaka, M.; Li, B.; Ueno, T.; Matsuda, H.; Matsui, T. Novel in situ visualisation of rat intestinal absorption of polyphenols via matrix-assisted laser desorption/ionisation mass spectrometry imaging. Sci. Rep. 2019, 9 (1), 5–8.
[70] Tanaka, M.; Hong, S. M.; Akiyama, S.; Hu, Q. Q.; Matsui, T. Visualized absorption of anti-atherosclerotic dipeptide, Trp-His, in Sprague-Dawley rats by LC-MS and MALDI-MS imaging analyses. Mol. Nutr. Food Res. 2015, 59 (8), 1541–1549.
[71] Yang, W.; Yu, X. C.; Chen, X. Y.; Zhang, L.; Lu, C. T.; Zhao, Y. Z. Pharmacokinetics and tissue distribution profile of icariin propylene glycol-liposome intraperitoneal injection in mice. J. Pharm. Pharmacol. 2012, 64 (2), 190–198.
[72] Chen, L.; Cao, H.; Huang, Q.; Xiao, J.; Teng, H. Absorption, metabolism and bioavailability of flavonoids: a review. Crit. Rev. Food Sci. Nutr. 2021, 1–13.
[73] Yuan, J. P.; Wang, J. H.; Liu, X. Metabolism of dietary soy isoflavones to equol by human intestinal microflora-implications for health. Mol. Nutr. Food Res. 2007, 51 (7), 765–781.
[74] Abe, C.; Zhang, Y.; Takao, K.; Sasaki, K.; Ochiai, K.; Matsui, T. Visualization analysis of glyceollin production in germinating soybeans by matrix-assisted laser desorption/ionization mass spectrometric imaging technique. J. Agric. Food Chem. 2021, 69 (25), 7057–7063.
[75] Nectoux, A. M.; Abe, C.; Huang, S. W.; Ohno, N.; Tabata, J.; Miyata, Y.; Tanaka, K.; Tanaka, T.; Yamamura, H.; Matsui, T. Absorption and metabolic behavior of hesperidin (rutinosylated hesperetin) after single oral administration to Sprague- Dawley rats. J. Agric. Food Chem. 2019, 67 (35), 9812–9819.
[76] Nagata, C.; Takatsuka, N.; Kawakami, N.; Shimizu, H. Soy product intake and hot flashes in Japanese women: results from a community-based prospective study. Am. J. Epidemiol. 2001, 153 (8), 790–793.
[77] Wang, H. J.; Murphy, P. A. Isoflavone composition of American and Japanese soybeans in iowa: effects of variety, crop year, and location. J. Agric. Food Chem. 1994, 42 (8), 1674–1677.
[78] Matthies, A.; Loh, G.; Blaut, M.; Braune, A. Daidzein and genistein are converted to equol and 5-hydroxy-equol by human intestinal slackia isoflavoniconvertens in gnotobiotic rats. J. Nutr. 2012, 142 (1), 40–46.
[79] Soukup, S. T.; Helppi, J.; Müller, D. R.; Zierau, O.; Watzl, B.; Vollmer, G.; Diel, P.; Bub, A.; Kulling, S. E. Phase II metabolism of the soy isoflavones genistein and daidzein in humans, rats and mice: a cross-species and sex comparison. Arch. Toxicol. 2016, 90 (6),1335–1347.
[80] Shelnutt, S. R.; Cimino, C. O.; Wiggins, P. A.; Ronis, M. J. J.; Badger, T. M. Pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein in men and women after consumption of a soy beverage. Am. J. Clin. Nutr. 2002, 76 (3), 588–594.
[81] Beckman, B. S.; Burow, M. E. Transport and metabolism of equol by Caco-2 human intestinal cells. J. Agric. Food Chem. 2001, 57 (1), 2921–2927.
[82] Rüfer, C. E.; Maul, R.; Donauer, E.; Fabian, E. J.; Kulling, S. E. In vitro and in vivo metabolism of the soy isoflavone glycitein. Mol. Nutr. Food Res. 2007, 51 (7), 813– 823.
[83] John, K. M. M.; Jung, E. S.; Lee, S.; Kim, J. S.; Lee, C. H. Primary and secondary metabolites variation of soybean contaminated with Aspergillus sojae. Food Res. Int. 2013, 54 (1), 487–494.
[84] Ge, J.; Tan, B. X.; Chen, Y.; Yang, L.; Peng, X. C.; Li, H. Z.; Lin, H. J.; Zhao, Y.; Wei, M.; Cheng, K.; Li, L. H.; Dong, H.; Gao, F.; He, J. P.; Wu, Y.; Qiu, M.; Zhao, Y. L.; Su, J. M.; Hou, J. M.; Liu, J. Y. Interaction of green tea polyphenol epigallocatechin-3-gallate with sunitinib: potential risk of diminished sunitinib bioavailability. J. Mol. Med. 2011, 89 (6), 595–602.
[85] Yang, C.; Wang, Q.; Yang, S.; Yang, Q.; Wei, Y. An LC–MS/MS method for quantitation of cyanidin-3-O-glucoside in rat plasma: application to a comparative pharmacokinetic study in normal and streptozotocin-induced diabetic rats. Biomed. Chromatogr. 2018, 32 (2), 1–6.
[86] Li, X.; Choi, J. S. Effect of genistein on the pharmacokinetics of paclitaxel administered orally or intravenously in rats. Int. J. Pharm. 2007, 337, 188–193.
[87] 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 (7), 1956–1961.
[88] Sugawara, T.; Kushiro, M.; Zhang, H.; Nara, E.; Ono, H.; Nagao, A. Lysophosphatidylcholine enhances carotenoid uptake from mixed micelles by Caco- 2 human intestinal cells. J. Nutr. 2001, 131 (11), 2921–2927.
[89] Hosoda, K.; Furuta, T.; Yokokawa, A.; Ishii, K. Identification and quantification of daidzein-7-glucuronide-4′-sulfate, genistein-7-glucuronide-4′-sulfate and genistein- 4′,7-diglucuronide as major metabolites in human plasma after administration of kinako. Anal. Bioanal. Chem. 2010, 397, 1563-1572.
[90] Zhang, Y.; Song, T. T.; Cunnick, J. E.; Murphy, P. A.; Hendrich, S. Daidzein and genistein glucuronides in vitro are weakly estrogenic and activate human natural killer cells at nutritionally relevant concentrations. J. Nutr. 1999, 129 (2), 399–405.
[91] Cao, Y. X.; Yang, X. J.; Liu, J.; Li, K. X. Effects of daidzein sulfates on blood pressure and artery of rats. Basic Clin. Pharmacol. Toxicol. 2006, 99, 425–430.
[92] Mukai, R. Prenylation enhances the biological activity of dietary flavonoids by altering their bioavailability. Biosci. Biotechnol. Biochem. 2018, 82 (2), 207–215.
[93] Barbhaiya, R. H.; Dandekar, K. A., Greene, D. S. Pharmacokinetics, absolute bioavailability, and disposition of [14C] nefazodone in humans. Drug Metab. Dispos.1996, 24(1), 91–95.
[94] Kida, K.; Suzuki, M.; Matsumoto, N.; Nanjo, F.; Hara, Y. Identification of biliary metabolites of (-)-epigallocatechin gallate in rats. J. Agric. Food Chem. 2000, 48 (9), 4151–4155.
[95] Bijsterbosch, M. K.; Duursma, A. M.; Bouma, J. M. W.; Gruber, M. The plasma volume of the Wistar rat in relation to the body weight. Experientia 1981, 37 (4), 381–382.
[96] Quadri, S. S.; Stratford, R. E.; Boué, S. M.; Cole, R. B. Screening and identification of glyceollins and their metabolites by electrospray ionization tandem mass spectrometry with precursor ion scanning. Anal. Chem. 2013, 85 (3), 1727–1733.
[97] Quadri, S. S.; Stratford, R. E.; Boué, S. M.; Cole, R. B. Identification of glyceollin metabolites derived from conjugation with glutathione and glucuronic acid in male ZDSD rats by online liquid chromatography-electrospray ionization tandem mass spectrometry. J. Agric. Food Chem. 2014, 62 (12), 2692–2700.
[98] Wang, Q.; Morris, M. E. Flavonoids modulate monocarboxylate transporter-1- mediated transport of γ-hydroxybutyrate in vitro and in vivo. Pharmacology 2007, 35 (2), 201–208.
[99] An, G.; Wang, X.; Morris, M. E. Flavonoids are inhibitors of human Organic Anion Transporter 1 (OAT1)-mediated transport. Drug Metab. Dispos. 2014, 42 (9), 1357–1366.
[100] Wang, X.; Wolkoff, A. W.; Morris, M. E. Flavonoids as a novel class of human organic anion-transporting polypeptide OATP1B1 (OATP-C) modulators. Drug Metab. Dispos. 2005, 33 (11), 1666–1672.
[101] Tipoe, G. L.; Leung, T. M.; Liong, E. C.; Lau, T. Y. H.; Fung, M. L.; Nanji, A. A. Epigallocatechin-3-gallate (EGCG) reduces liver inflammation, oxidative stress and fibrosis in carbon tetrachloride (CCl4)-induced liver injury in mice. Toxicology 2010, 273 (1), 45–52.
[102] Mokni, M.; Limam, F.; Elkahoui, S.; Amri, M.; Aouani, E. Strong cardioprotective effect of resveratrol, a red wine polyphenol, on isolated rat hearts after ischemia/reperfusion injury. Arch. Biochem. Biophys. 2007, 457 (1), 1–6.
[103] Lee, S. J.; Vuong, T. A.; Go, G. Y.; Song, Y. J.; Lee, S.; Lee, S. Y.; Kim, S. W.; Lee, J.; Kim, Y. K.; Seo, D. W.; Kim, K. H.; Kang, J. S.; Bae, G. U. An isoflavone compound daidzein elicits myoblast differentiation and myotube growth. J. Funct. Foods 2017, 38, 438–446.
論文の公開元へ
