Isoflavone research towards healthcare applications

Abstract

A survey of the current literature on natural isoflavones and their biological activity is presented. This subcategory of a large group of plant polyphenolics has particular characteristics, structural as well as pharmacological, which makes it suitable for discussion of pleiotropic activities of phytochemicals and their exploitation in healthcare, beyond the concept of selectively targeted new drugs for narrow therapeutic indication.

Keywords

Isoflavones / phytoestrogens / genistein / novel drugs / nutraceuticals / functional food

References

[1] Siegel RL,Jemal A.Cancer statistics, 2019..CA A Cancer J Clin2018;69:7-34

[2] Ferlay J,Soerjomataram I.Estimating the global cancer incidence and mortality in 2018: GLOBOCAN sources and methods..Int J Cancer2019;144:1941-53

[3] Cragg GM.Natural products: a continuing source of novel drug leads..Biochimica et Biophysica Acta (BBA) - General Subjects2013;1830:3670-95 PMCID:PMC3672862

[4] Newman DJ.Natural products as sources of new drugs from 1981 to 2014..J Nat Prod2015;79:629-61

[5] Kaur V,Kumar A,Dhillon VS.Pharmacotherapeutic potential of phytochemicals: implications in cancer chemoprevention and future perspectives..Biomed Pharmacother2018;97:564-86

[6] Sharifi-Rad J,Boyunegmez Tumer T.Natural products and synthetic analogs as a source of antitumor drugs..Biomolecules2019;9:679 PMCID:PMC6920853

[7] Dias DA,Roessner U.A historical overview of natural products in drug discovery..Metabolites2012;2:303-36 PMCID:PMC3901206

[8] Harvey AL,Quinn RJ.The re-emergence of natural products for drug discovery in the genomics era..Nat Rev Drug Discov2015;14:111-29

[9] Ertl P.Cheminformatics analysis of natural product scaffolds: comparison of scaffolds produced by animals, plants, fungi and bacteria..Mol Inform2020;39:2000017

[10] Chen Y.Cheminformatics in natural product-based drug discovery..Mol Inform2020;2000171

[11] Chen Y,Friedrich NO.Characterization of the chemical space of known and readily obtainable natural products..J Chem Inf Model2018;58:1518-32

[12] Ntie-kang F,Ayimele GA.“Drug-likeness” properties of natural compounds..Phys Sci Rev2019;4:

[13] Saldívar-gonzález FI,Medina-franco JL.Chemical space of naturally occurring compounds..Phys Sci Rev2019;4:

[14] Luo Y,Zhao H.Recent advances in natural product discovery..Curr Opin Biotechnol2014;30:230-7 PMCID:PMC4253731

[15] Lagunin AA,Gawande DY.Chemo- and bioinformatics resources for in silico drug discovery from medicinal plants beyond their traditional use: a critical review..Nat Prod Rep2014;31:1585-611

[16] Biasutto L,Sassi N.Improving the efficacy of plant polyphenols..Anticancer Agents Med Chem2014;14:1332-42

[17] Grynkiewicz G,Krzeczyński P.Hexenoses in design of glycoconjugates - from chemistry to function biological activity of genistein derivatives..Chem Biol Interface2014;4:301-20

[18] Blakemore DC,Churcher I.Organic synthesis provides opportunities to transform drug discovery..Nature Chem2018;10:383-94

[19] Messina MA.Brief historical overview of the past two decades of soy and isoflavone research..J Nutr2010;140:1350S-4

[20] Ko KP.Isoflavones: chemistry, analysis, functions and effects on health and cancer..Asian Pac J Cancer Prev2014;15:7001-10

[21] Szeja W,Rusin A.Isoflavones, their glycosides and glycoconjugates. Synthesis and biological activity..Curr Org Chem2017;21:218-35 PMCID:PMC5427819

[22] Venkataraman K.Flavones and isoflavones..Progr Chem Org Nat Prod1959;17:2-69

[23] Wong E.Structural and biogenetic relationships of isoflavonoids..Progr Chem Org Nat Prod1970;28:1-73

[24] Catherine A,Lester Packer L.Flavonoids in Health and Disease2003;Second EditionBoca Raton, FLCRC Press

[25] Grotewold E.The Science of Flavonoids.2006;New YorkSpringer Science + Business Media

[26] Andersen OM.Flavonoids Chemistry, Biochemistry and Applications.2006;Boca Raton, FLCRC Taylor & Francis

[27] Keller RB.Flavonoids: Biosynthesis, Biological Effects and Dietary Sources.2009;New YorkNova Science Publishers, Inc.

[28] Vicente O.Flavonoids: antioxidant compounds for plant defence...and for a healthy human diet..Not Bot Horti Agrobo2018;46:14-21

[29] Panche AN,Chandra SR.Flavonoids: an overview..J Nutr Sci2016;5:e47 PMCID:PMC5465813

[30] Kumar S.Chemistry and biological activities of flavonoids: an overview..Sci World J2013;2013:1-16 PMCID:PMC3891543

[31] Perez-vizcaino F.Research trends in flavonoids and health..Arch Biochem Biophys2018;646:107-12

[32] Naoumkina MA,Gallego-giraldo L,Zhao PX.Genome-wide analysis of phenylpropanoid defence pathways: phenylpropanoid defence pathways..Mol Plant Pathol2010;11:829-46 PMCID:PMC6640277

[33] Prasad S,Yadav V,Aggarwal B.Targeting inflammatory pathways by flavonoids for prevention and treatment of cancer..Planta Med2010;76:1044-63

[34] Procházková D,Wilhelmová N.Antioxidant and prooxidant properties of flavonoids..Fitoterapia2011;82:513-23

[35] Romano B,Montanaro V,Milic N.Novel insights into the pharmacology of flavonoids: pharmacology of flavonoids..Phytother Res2013;27:1588-96

[36] Tungmunnithum D,Pholboon A.Flavonoids and other phenolic compounds from medicinal plants for pharmaceutical and medical aspects: an overview..Medicines (Basel)2018;5:93 PMCID:PMC6165118

[37] Ravishankar D,Greco F.Flavonoids as prospective compounds for anti-cancer terapy..Int J Biochem Cell Biol2013;45:2821-31

[38] Raffa D,Raimondi MV,Daidone G.Recent discoveries of anticancer flavonoids..Eur J Med Chem2017;142:213-28

[39] Rodríguez-garcía C,Gaforio JJ.Dietary flavonoids as cancer chemopreventive agents: an updated review of human studies..Antioxidants2019;8:137 PMCID:PMC6562590

[40] Abotaleb M,Varghese E.Flavonoids in cancer and apoptosis..Cancers2019;11:28 PMCID:PMC6357032

[41] Kopustinskiene DM,Savickas A.Flavonoids as anticancer agents..Nutrients2020;12:457 PMCID:PMC7071196

[42] Thilakarathna S.Flavonoid bioavailability and attempts for bioavailability enhancement..Nutrients2013;5:3367-87 PMCID:PMC3798909

[43] Rodriguez-mateos A,Krueger CG.Bioavailability, bioactivity and impact on health of dietary flavonoids and related compounds: an update..Arch Toxicol2014;88:1803-53

[44] Nicolle E,Faure P.Flavonoids as promising lead compounds in type 2 diabetes mellitus: molecules of interest and structure-activity relationship..Curr Med Chem2011;18:2661-72

[45] Mueckler M.The SLC2 (GLUT) family of membrane transporters..Mol Asp Med2013;34:121-38 PMCID:PMC4104978

[46] Aguillón AR,Segretti ND.Synthetic strategies toward SGLT2 Inhibitors..Org Process Res Dev2018;22:467-88

[47] Balentine DA,Erdman JW.Recommendations on reporting requirements for flavonoids in research..Am J Clin Nutr2015;101:1113-25

[48] Harnly J.Importance of accurate measurements in nutrition research: dietary flavonoids as a case study..Adv Nutr2016;7:375-82 PMCID:PMC4785473

[49] Maggiora G,Stumpfe D.Molecular similarity in medicinal chemistry miniperspective..J Med Chem2014;57:3186-204

[50] Popelier P.QSAR models based on quantum topological molecular similarity..Eur J Med Chem2006;41:862-73

[51] Renner S.Scaffold-hopping potential of ligand-based similarity concepts..ChemMedChem2006;1:181-5

[52] Scalbert A,Arita M.Databases on food phytochemicals and their health-promoting effects..J Agric Food Chem2011;59:4331-48

[53] Wishart DS,Stanislaus A.Cancer metabolomics and the human metabolome database..Metabolites2016;6:10 PMCID:PMC4812339

[54] Sebastian RS,Goldman JD.New, publically available flavonoid data products: valuable resources for emerging science..J Food Compos Anal2017;64:68-72

[55] Veitch NC.Isoflavonoids of the leguminosae..Nat Prod Rep2007;24:417-64

[56] Adams NR.Permanent infertility in ewes exposed to plant oestrogens..Aust Vet J1990;67:197-201

[57] Adams NR.Detection of the effects of phytoestrogens on sheep and cattle..J Anim Sci1995;73:1509-15

[58] Jefferson WN,Williams CJ.Reproductive consequences of developmental phytoestrogen exposure..Reproduction2012;143:247-60 PMCID:PMC3443604

[59] Douglas C,Arjmandi B.Soy and its isoflavones: the truth behind the science in breast cancer..Anticancer Agents Med Chem2013;13:1178-87

[60] Zaheer K.An updated review of dietary isoflavones: nutrition, processing, bioavailability and impacts on human health..Crit Rev Food Sci Nutr2016;57:1280-93

[61] Xiao CW.Health effects of soy protein and isoflavones in humans.J Nutr2008;138:1244S-9

[62] Ososki AL.Phytoestrogens: a review of the present state of research..Phytother Res2003;17:845-69

[63] Hooper L,Kurzer M.Effects of soy protein and isoflavones on circulating hormone concentrations in pre- and post-menopausal women: a systematic review and meta-analysis..Hum Reprod Update2009;15:423-40 PMCID:PMC2691652

[64] Douglas C,Arjmandi B.Soy and its isoflavones: the truth behind the science in breast cancer..Anticancer Agents Med Chem2013;13:1178-87

[65] Chae HS,Won JY,Yim H.Molecular targets of genistein and its related flavonoids to exert anticancer effects..Int J Mol Sci2019;20:2420 PMCID:PMC6566427

[66] Sacks FM,Van Horn L.Soy protein, isoflavones, and cardiovascular health..Circulation2006;113:1034-44

[67] Ullmann U,Flühmann B.Bonistein (synthetic genistein) a food component in development for a bone health nutraceutical..J Physiol Pharmacol2005;56:79-95

[68] Křížová L,Kašparovská J.Isoflavones..Molecules2019;24:1076 PMCID:PMC6470817

[69] Jian L.Soy, isoflavones, and prostate cancer..Mol Nutr Food Res2009;53:217-26

[70] Banecka-Majkutewicz Z,Gabig-Cimińska M,Węgrzyn G.Putative biological mechanism of efficiency of substrate reduction therapies for mucopolisaccharidoses..Arch Immunol Ther Exp2012;60:461-8

[71] Ferrari SM,Guidi P.Genotoxicity evaluation of the soybean isoflavone genistein in human papillary thyroid cancer cells. Study of its potential use in thyroid cancer therapy..Nutr Cancer2019;71:1335-44

[72] Rusin A,Grynkiewicz G.Synthetic derivatives of genistein, their properties and possible applications..Acta Biochim Polon2010;57:23-34

[73] Landauer MR,Kaytor MD.Mechanism and therapeutic window of genistein nanosuspension to protect against hematopoietic-acute radiation syndrome..J Rad Res2019;2019:308-17 PMCID:PMC6530628

[74] Singh VK.Bio 300: a promising radiation countermeasure under advanced development for acute radiation syndrome and the delayed effects of acute radiation exposure..Exp Opin Investig Drugs2020;29:429-41

[75] Cheema AK,Santiago PT.Pharmacokinetic and metabolomics studies with BIO 300, a nanosuspension of genistein in a nonhuman primate model..Int J Mol Sci2019;20:1231 PMCID:PMC6429499