A major daidzin metabolite 7,8,4′-trihydroxyisoflavone found in the plasma of soybean extract-fed rats attenuates monocyte-endothelial cell adhesion

Food Chemistry

Volumn 240, Issue , 2018, Pages 607-614

  Lee, Charles C ^a   Dudonné, Stéphanie ^b   Kim, Jong Hun ^c,d   Kim, Ji Seung ^e   Dubé, Pascal ^b   Kim, Jong Eun ^f   Desjardins, Yves ^b   Park, Jung Han Yoon ^c,d   Lee, Ki Won ^c,d,e   Lee, Chang Yong ^a  

^a Cornell University ^*  (United States)

^b LAVAL UNIVERSITY   (Canada)

^c Seoul National University   (South Korea)

^d Seoul National University   (South Korea)

^e Seoul National University   (South Korea)

^f Dongguk University   (South Korea)

Author keywords

7,8,4 Trihydroxyisoflavone; Atherosclerosis prevention; Daidzein metabolite; Monocyte endothelial adhesion; Soy isoflavone phase I metabolism

Indexed keywords

AMINO ACIDS; BIOCHEMISTRY; BIOMOLECULES; BODY FLUIDS; CELL ADHESION; CELLS; CYTOLOGY; DISEASES; FLAVONOIDS; FUNCTIONAL FOOD; METABOLISM; METABOLITES; NITROGEN FIXATION; PHYSIOLOGY; RATS;

ATHEROSCLEROSIS PREVENTION; CARDIO-VASCULAR DISEASE; DAIDZEIN; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; MONOCYTE CHEMOTACTIC PROTEIN-1; PHASE I; TUMOR NECROSIS FACTOR ALPHA; VASCULAR CELL ADHESION MOLECULE-1;

ENDOTHELIAL CELLS;

7,8,4' TRIHYDROXYISOFLAVONE; ACETYLDAIDZIN; ACETYLGENISTIN; ACETYLGLYCITIN; COUMESTROL; DAIDZEIN; DAIDZIN; DIHYDROXYISOFLAVONE; DRUG METABOLITE; EQUOL; EQUOL GLUCUORNIDE; GENISTEIN; GENISTIN; GLYCITEIN; GLYCITIN; I KAPPA B KINASE; I KAPPA B KINASE ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; ISOFLAVONE DERIVATIVE; MALONYLDAIDZIN; MALONYLGENISTIN; MALONYLGLYCITIN; MONOCYTE CHEMOTACTIC PROTEIN 1; SOYBEAN EXTRACT; TUMOR NECROSIS FACTOR; UNCLASSIFIED DRUG; VASCULAR CELL ADHESION MOLECULE 1; 7,8,4'-TRIHYDROXYISOFLAVONE;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; ATHEROSCLEROSIS; CELL ADHESION; CELL ADHESION ASSAY; CELL VIABILITY; CONTROLLED STUDY; DOWN REGULATION; DRUG BLOOD LEVEL; ENDOTHELIUM CELL; ENZYME PHOSPHORYLATION; HUMAN; HUMAN CELL; MALE; METABOLOMICS; MONOCYTE; NONHUMAN; RAT; SIGNAL TRANSDUCTION; SINGLE DRUG DOSE; UMBILICAL VEIN ENDOTHELIAL CELL; ANIMAL; SOYBEAN;

ANIMALS; CELL ADHESION; HUMANS; ISOFLAVONES; MONOCYTES; RATS; SOYBEANS; TUMOR NECROSIS FACTOR-ALPHA;

EID: 85026764149     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2017.08.002     Document Type: Article

References (28)

1. Andrade, C.M., Sa, M.F., Toloi, M.R., Effects of phytoestrogens derived from soy bean on expression of adhesion molecules on HUVEC. Climacteric 15:2 (2012), 186–194.
2. Barnes, S., Prasain, J., D'Alessandro, T., Arabshahi, A., Botting, N., Lila, M.A.,.. Weaver, C.M., The metabolism and analysis of isoflavones and other dietary polyphenols in foods and biological systems. Food & Function 2:5 (2011), 235–244.
3. Cassidy, A., Minihane, A.M., The role of metabolism (and the microbiome) in defining the clinical efficacy of dietary flavonoids. American Journal of Clinical Nutrition 105:1 (2017), 10–22.
4. Chen, L., Zhang, Y.H., Huang, T., Cai, Y.D., Gene expression profiling gut microbiota in different races of humans. Scientific Reports, 6, 2016.
5. Chen, Z.J., Zheng, S.R., Li, L.P., Jiang, H.D., Metabolism of flavonoids in human: a comprehensive review. Current Drug Metabolism 15:1 (2014), 48–61.
6. Dudonne, S., Dube, P., Pilon, G., Marette, A., Jacques, H., Weisnagel, J., Desjardins, Y., Modulation of strawberry/cranberry phenolic compounds glucuronidation by co-supplementation with onion: characterization of phenolic metabolites in rat plasma using an optimized muSPE-UHPLC-MS/MS Method. Journal of Agricultural and Food Chemistry, 2014.
7. Esaki, H., Onozaki, H., Morimitsu, Y., Kawakishi, S., Osawa, T., Potent antioxidative isoflavones isolated from soybeans fermented with aspergillus saitoi. Bioscience, Biotechnology, and Biochemistry 62:4 (1998), 740–746.
8. U.S. Food and Drug Administration (FDA) (2005). Guidance for industry: estimating the maximum safe starting dose in initial clinical trials for therapeurics in adult healthy volunteers.
9. Granato, D., Branco, G.F., Nazzaro, F., Cruz, A.G., Faria, J.A.F., Functional foods and nondairy probiotic food development: trends, concepts, and products. Comprehensive Reviews in Food Science and Food Safety 9:3 (2010), 292–302.
10. Heinonen, S.M., Hoikkala, A., Wahala, K., Adlercreutz, H., Metabolism of the soy isoflavones daidzein, genistein and glycitein in human subjects. Identification of new metabolites having an intact isoflavonoid skeleton. Journal of Steroid Biochemistry and Molecular Biology 87:4–5 (2003), 285–299.
11. Heinonen, S.M., Wahala, K., Liukkonen, K.H., Aura, A.M., Poutanen, K., Adlercreutz, H., Studies of the in vitro intestinal metabolism of isoflavones aid in the identification of their urinary metabolites. Journal of Agriculture and Food Chemistry 52:9 (2004), 2640–2646.
12. Jia, Z., Babu, P.V., Si, H., Nallasamy, P., Zhu, H., Zhen, W.,.. Liu, D., Genistein inhibits TNF-alpha-induced endothelial inflammation through the protein kinase pathway A and improves vascular inflammation in C57BL/6 mice. International Journal of Cardiology 168:3 (2013), 2637–2645.
13. Kim, H., Kim, J.R., Kang, H., Choi, J., Yang, H., Lee, P.,.. Lee, K.W., 7,8,4'-Trihydroxyisoflavone attenuates DNCB-induced atopic dermatitis-like symptoms in NC/Nga mice. PLoS One, 9(8), 2014, e104938.
14. Kulling, S.E., Honig, D.M., Metzler, M., Oxidative metabolism of the soy isoflavones daidzein and genistein in humans in vitro and in vivo. Journal of Agriculture and Food Chemistry 49:6 (2001), 3024–3033.
15. Kulling, S.E., Honig, D.M., Simat, T.J., Metzler, M., Oxidative in vitro metabolism of the soy phytoestrogens daidzein and genistein. Journal of Agriculture and Food Chemistry 48:10 (2000), 4963–4972.
16. Lee, C.C., Dudonné, S., Dubé, P., Desjardins, Y., Kim, J.H., Kim, J.S.,.. Lee, C.Y., Comprehensive phenolic composition analysis and evaluation of Yak-Kong soybean (Glycine max) for the prevention of atherosclerosis. Food Chemistry 234 (2017), 486–493.
17. Libby, P., Inflammation and cardiovascular disease mechanisms. American Journal of Clinical Nutrition 83:2 (2006), 456S–460S.
18. Libby, P., Ridker, P.M., Maseri, A., Inflammation and atherosclerosis. Circulation 105:9 (2002), 1135–1143.
19. Manach, C., Williamson, G., Morand, C., Scalbert, A., Remesy, C., Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. American Journal of Clinical Nutrition 81:1 (2005), 230s–242s.
20. Nagarajan, S., Mechanisms of anti-atherosclerotic functions of soy-based diets. Journal of Nutritional Biochemistry 21:4 (2010), 255–260.
21. Nagarajan, S., Stewart, B.W., Badger, T.M., Soy isoflavones attenuate human monocyte adhesion to endothelial cell-specific CD54 by inhibiting monocyte CD11a. Journal of Nutrition 136:9 (2006), 2384–2390.
22. Peng, W.X., Wang, L.S., Li, H.D., Abd El-Aty, A.M., Chen, G.L., Zhou, H.H., Evidence for the involvement of human liver microsomes CYP1A2 in the mono-hydroxylation of daidzein. Clinica Chimica Acta 334:1–2 (2003), 77–85.
23. Poolsup, N., Po, A.L.W., Knight, T.L., Pharmacogenetics and psychopharmacotherapy. Journal of Clinical Pharmacy and Therapeutics 25:3 (2000), 197–220.
24. Ross, R., Atherosclerosis–an inflammatory disease. New England Journal of Medicine 340:2 (1999), 115–126.
25. Rufer, C.E., Bub, A., Moseneder, J., Winterhalter, P., Sturtz, M., Kulling, S.E., Pharmacokinetics of the soybean isoflavone daidzein in its aglycone and glucoside form: a randomized, double-blind, crossover study. American Journal of Clinical Nutrition 87:5 (2008), 1314–1323.
26. Tai, S.S., Lin, C.G., Wu, M.H., Chang, T.S., Evaluation of depigmenting activity by 8-hydroxydaidzein in mouse B16 melanoma cells and human volunteers. International Journal of Molecular Sciences 10:10 (2009), 4257–4266.
27. Tedgui, A., Mallat, Z., Cytokines in atherosclerosis: pathogenic and regulatory pathways. Physiological Reviews 86:2 (2006), 515–581.
28. Zhan, S., Ho, S.C., Meta-analysis of the effects of soy protein containing isoflavones on the lipid profile. American Journal of Clinical Nutrition 81:2 (2005), 397–408.