Abstract
Genistin is a type of isoflavone glycoside and has a broad range of health benefits. It is found in a variety of dietary plants, such as soybean, kudzu (Japanese arrowroot), and other plant-based products. Genistin has been described to have several beneficial health impacts, such as decreasing the risk of osteoporosis and post-menopausal symptoms, as well as anti-cancer, anti-oxidative, cardioprotective, anti-apoptotic, neuroprotective, hepatoprotective, and anti-microbial activities. It may also assist individuals with metabolic syndrome. This review summarizes some of the molecular impacts and prospective roles of genistin in maintaining and treatment of health disorders. The review could help to develop novel genistin medicine with significant health benefits for application in the nutraceutical and pharmaceutical fields.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Abdallah HM, Al-Abd AM, Asaad GF, Abdel-Naim AB, El-halawany AM (2014) Isolation of antiosteoporotic compounds from seeds of Sophora japonica. PLoS ONE 9:e98559. https://doi.org/10.1371/journal.pone.0098559
Abel J, de Ruiter N (1989) Inhibition of hydroxyl-radical-generated DNA degradation by metallothionein. Toxicol Lett 47:191–196. https://doi.org/10.1016/0378-4274(89)90075-1
Akanda MR, Uddin MN, Kim IS, Ahn D, Tae HJ, Park BY (2019) The biological and pharmacological roles of polyphenol flavonoid tilianin. Eur J Pharmacol 842:291–297. https://doi.org/10.1016/j.ejphar.2018.10.044
Andres S, Hansen U, Niemann B, Palavinskas R, Lampen A (2015) Determination of the isoflavone composition and estrogenic activity of commercial dietary supplements based on soy or red clover. Food Funct 6:2017–2025. https://doi.org/10.1039/c5fo00308c
Appel GB, Appel AS (1990) Lipid-lowering agents in proteinuric diseases. Am J Nephrol 10(Suppl 1):110–115. https://doi.org/10.1159/000168204
Arnold M, Sierra MS, Laversanne M, Soerjomataram I, Jemal A, Bray F (2017) Global patterns and trends in colorectal cancer incidence and mortality. Gut 66:683–691. https://doi.org/10.1136/gutjnl-2015-310912
Ballistreri G, Arena E, Fallico B (2009) Influence of ripeness and drying process on the polyphenols and tocopherols of Pistacia vera L. Molecules 14:4358–4369. https://doi.org/10.3390/molecules14114358
Bayazit V (2004) Cytotoxic effects of some animal and vegetable extracts and some chemicals on liver and colon carcinoma and myosarcoma. Saudi Med J 25:156–163
Bebrevska L, Foubert K, Hermans N, Chatterjee S, Van Marck E, De Meyer G, Vlietinck A, Pieters L, Apers S (2010) In vivo antioxidative activity of a quantified Pueraria lobata root extract. J Ethnopharmacol 127:112–117. https://doi.org/10.1016/j.jep.2009.09.039
Benedetti MS, Whomsley R, Poggesi I, Cawello W, Mathy FX, Delporte ML, Papeleu P, Watelet JB (2009) Drug metabolism and pharmacokinetics. Drug Metab Rev 41:344–390. https://doi.org/10.1080/10837450902891295
Benlhabib E, Baker JI, Keyler DE, Singh AK (2004) Kudzu root extract suppresses voluntary alcohol intake and alcohol withdrawal symptoms in P rats receiving free access to water and alcohol. J Med Food 7:168–179. https://doi.org/10.1089/1096620041224210
Bhatt PC, Pandey P, Panda BP, Anwar F, Kumar V (2017) Commentary: L-3-n-butylphthalide rescues hippocampal synaptic failure and attenuates neuropathology in aged APP/PS1 mouse model of Alzheimer's disease. Front Aging Neurosci 9:4. https://doi.org/10.3389/fnagi.2017.00004
Bhatt PC, Pathak S, Kumar V, Panda BP (2018) Attenuation of neurobehavioral and neurochemical abnormalities in animal model of cognitive deficits of Alzheimer's disease by fermented soybean nanonutraceutical. Inflammopharmacology 26:105–118. https://doi.org/10.1007/s10787-017-0381-9
Bian QQ, Yang ZP, Liu JQ, Liu SM (2005) Simultaneous determination of the four effective components in Huaijiao pill by HPLC. Zhongguo Zhong Yao Za Zhi 30:1513–1515
Boue SM, Wiese TE, Nehls S, Burow ME, Elliott S, Carter-Wientjes CH, Shih BY, McLachlan JA, Cleveland TE (2003) Evaluation of the estrogenic effects of legume extracts containing phytoestrogens. J Agric Food Chem 51:2193–2199. https://doi.org/10.1021/jf021114s
Browning AM, Walle UK, Walle T (2005) Flavonoid glycosides inhibit oral cancer cell proliferation–role of cellular uptake and hydrolysis to the aglycones. J Pharm Pharmacol 57:1037–1042. https://doi.org/10.1211/0022357056514
Bustamante-Rangel M, Delgado-Zamarreno MM, Carabias-Martinez R, Dominguez-Alvarez J (2012) Analysis of isoflavones in soy drink by capillary zone electrophoresis coupled with electrospray ionization mass spectrometry. Anal Chim Acta 709:113–119. https://doi.org/10.1016/j.aca.2011.10.015
Caligiani A, Palla G, Maietti A, Cirlini M, Brandolini V (2010) 1H NMR fingerprinting of soybean extracts, with emphasis on identification and quantification of isoflavones. Nutrients 2:280–289. https://doi.org/10.3390/nu2030280
Cameron JS (1990) Proteinuria and progression in human glomerular diseases. Am J Nephrol 10(Suppl 1):81–87. https://doi.org/10.1159/000168199
Carrara VS, Amato AA, Neves FA, Bazotte RB, Mandarino JM, Nakamura CV, Filho BP, Cortez DA (2009) Effects of a methanolic fraction of soybean seeds on the transcriptional activity of peroxisome proliferator-activated receptors (PPAR). Braz J Med Biol Res 42:545–550. https://doi.org/10.1590/s0100-879x2009000600011
Chang L, Ren Y, Cao L, Sun Y, Sun Q, Sheng N, Yuan L, Zhi X, Zhang L (2012) Simultaneous determination and pharmacokinetic study of six flavonoids from Fructus sophorae extract in rat plasma by LC-MS/MS. J Chromatogr B Anal Technol Biomed Life Sci 904:59–64. https://doi.org/10.1016/j.jchromb.2012.07.015
Chao WW, Chen SJ, Peng HC, Liao JW, Chou ST (2019) Antioxidant activity of Graptopetalum paraguayense E. Walther leaf extract counteracts oxidative stress induced by ethanol and carbon tetrachloride co-induced hepatotoxicity in rats. Antioxidants (Basel). https://doi.org/10.3390/antiox8080251
Chen TR, Chen LA, Wei QK (2010) Evaluation of quality of Radix Puerariae herbal medicine by isoflavonoids. J Pharm Pharmacol 62:644–650. https://doi.org/10.1211/jpp/62.05.0013
Cheng J, Wang J, Liang H, Wang Y, Zhao Y (2009) Constituents of Millettia nitida var. hirsutissima. Zhongguo Zhong Yao Za Zhi 34:1921–1926
Cherdshewasart W, Sriwatcharakul S (2007) Major isoflavonoid contents of the 1-year-cultivated phytoestrogen-rich herb, Pueraria mirifica. Biosci Biotechnol Biochem 71:2527–2533. https://doi.org/10.1271/bbb.70316
Cherdshewasart W, Subtang S, Dahlan W (2007) Major isoflavonoid contents of the phytoestrogen rich-herb Pueraria mirifica in comparison with Pueraria lobata. J Pharm Biomed Anal 43:428–434. https://doi.org/10.1016/j.jpba.2006.07.013
Chin YP, Tsui KC, Chen MC, Wang CY, Yang CY, Lin YL (2012) Bactericidal activity of soymilk fermentation broth by in vitro and animal models. J Med Food 15:520–526. https://doi.org/10.1089/jmf.2011.1918
Chiou RY, Cheng SL (2001) Isoflavone transformation during soybean koji preparation and subsequent miso fermentation supplemented with ethanol and NaCl. J Agric Food Chem 49:3656–3660. https://doi.org/10.1021/jf001524l
Choi EJ, Kim T, Lee MS (2007a) Pro-apoptotic effect and cytotoxicity of genistein and genistin in human ovarian cancer SK-OV-3 cells. Life Sci 80:1403–1408. https://doi.org/10.1016/j.lfs.2006.12.031
Choi I, Kim Y, Park Y, Seog H, Choi H (2007b) Anti-obesity activities of fermented soygerm isoflavones by Bifidobacterium breve. BioFactors 29:105–112
Christopoulos DC, Nicolaides AN, Belcaro G, Kalodiki E (1991) Venous hypertensive microangiopathy in relation to clinical severity and effect of elastic compression. J Dermatol Surg Oncol 17:809–813. https://doi.org/10.1111/j.1524-4725.1991.tb03264.x
Chu Q, Fu L, Wu T, Ye J (2005) Simultaneous determination of phytoestrogens in different medicinal parts of Sophora japonica L. by capillary electrophoresis with electrochemical detection. Biomed Chromatogr 19:149–154. https://doi.org/10.1002/bmc.431
Chung MJ, Kang AY, Lee KM, Oh E, Jun HJ, Kim SY, Auh JH, Moon TW, Lee SJ, Park KH (2006) Water-soluble genistin glycoside isoflavones up-regulate antioxidant metallothionein expression and scavenge free radicals. J Agric Food Chem 54:3819–3826. https://doi.org/10.1021/jf060510y
Clark H (2013) NCDs: a challenge to sustainable human development. Lancet 381:510–511. https://doi.org/10.1016/S0140-6736(13)60058-6
Cowherd RM, Lyle RE, McGehee RE Jr (1999) Molecular regulation of adipocyte differentiation. Semin Cell Dev Biol 10:3–10
Crews FT, Bechara R, Brown LA, Guidot DM, Mandrekar P, Oak S, Qin L, Szabo G, Wheeler M, Zou J (2006) Cytokines and alcohol. Alcohol Clin Exp Res 30:720–730. https://doi.org/10.1111/j.1530-0277.2006.00084.x
Cushnie TP, Lamb AJ (2005) Antimicrobial activity of flavonoids. Int J Antimicrob Agents 26:343–356
Dalal PK, Agarwal M (2015) Postmenopausal syndrome. Indian J Psychiatry 57:S222–S232. https://doi.org/10.4103/0019-5545.161483
Delgado-Zamarreno MM, Perez-Martin L, Bustamante-Rangel M, Carabias-Martinez R (2012) Pressurized liquid extraction as a sample preparation method for the analysis of isoflavones in pulses. Anal Bioanal Chem 404:361–366. https://doi.org/10.1007/s00216-012-5912-z
Du Q, Lib Z, Ito Y (2001) Preparative separation of isoflavone components in soybeans using high-speed counter-current chromatography. J Chromatogr A 923:271–274. https://doi.org/10.1016/s0021-9673(01)01031-7
Duke SO, Rimando AM, Pace PF, Reddy KN, Smeda RJ (2003) Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds of glyphosate-treated, glyphosate-resistant soybean. J Agric Food Chem 51:340–344. https://doi.org/10.1021/jf025908i
Fayed AE (2015) Review article: health benefits of some physiologically active ingredients and their suitability as yoghurt fortifiers. J Food Sci Technol 52:2512–2521. https://doi.org/10.1007/s13197-014-1393-8
Fukutake M, Takahashi M, Ishida K, Kawamura H, Sugimura T, Wakabayashi K (1996) Quantification of genistein and genistin in soybeans and soybean products. Food Chem Toxicol 34:457–461. https://doi.org/10.1016/0278-6915(96)87355-8
Gacek M (2014) Soy and legume seeds as sources of isoflavones: selected individual determinants of their consumption in a group of perimenopausal women. Menopause Rev-Przeglad Menopauzalny 13:27–31. https://doi.org/10.5114/pm.2014.41081
Gomuttapong S, Pewphong R, Choeisiri S, Jaroenporn S, Malaivijitnond S (2012) Testing of the estrogenic activity and toxicity of Stephania venosa herb in ovariectomized rats. Toxicol Mech Methods 22:445–457. https://doi.org/10.3109/15376516.2012.668573
Green DR, Kroemer G (2005) Pharmacological manipulation of cell death: clinical applications in sight? J Clin Invest 115:2610–2617. https://doi.org/10.1172/JCI26321
Greiner LL, Stahly TS, Stabel TJ (2001) The effect of dietary soy genistein on pig growth and viral replication during a viral challenge. J Anim Sci 79:1272–1279. https://doi.org/10.2527/2001.7951272x
Greiser KH, Kluttig A, Schumann B, Kors JA, Swenne CA, Kuss O, Werdan K, Haerting J (2005) Cardiovascular disease, risk factors and heart rate variability in the elderly general population: design and objectives of the cardiovascular disease, living and ageing in Halle (CARLA) study. BMC Cardiovasc Disord 5:33. https://doi.org/10.1186/1471-2261-5-33
Grun IU, Adhikari K, Li C, Li Y, Lin B, Zhang J, Fernando LN (2001) Changes in the profile of genistein, daidzein, and their conjugates during thermal processing of tofu. J Agric Food Chem 49:2839–2843. https://doi.org/10.1021/jf010028+
Gu M, Zheng AB, Jin J, Cui Y, Zhang N, Che ZP, Wang Y, Zhan J, Tu WJ (2016) Cardioprotective effects of genistin in rat myocardial ischemia-reperfusion injury studies by regulation of P2X7/NF-kappaB pathway. Evid Based Complement Altern Med 2016:5381290. https://doi.org/10.1155/2016/5381290
Hamalainen M, Nieminen R, Asmawi MZ, Vuorela P, Vapaatalo H, Moilanen E (2011) Effects of flavonoids on prostaglandin E2 production and on COX-2 and mPGES-1 expressions in activated macrophages. Planta Med 77:1504–1511. https://doi.org/10.1055/s-0030-1270762
Hamdy SM, Latif AK, Drees EA, Soliman SM (2012) Prevention of rat breast cancer by genistin and selenium. Toxicol Ind Health 28:746–757. https://doi.org/10.1177/0748233711422732
Hasumuma R, Kawaguchi K, Kikuchi S, Sugiyama T, Kumazawa Y (2007) Effects of isoflavones and soybeans fermented with Bacillus subtilis on lipopolysaccharide-induced production of tumor necrosis factor-alpha and fibrinolysis in vivo. Immunopharmacol Immunotoxicol 29:323–333. https://doi.org/10.1080/08923970701513526
Hellstrom AC, Muntzing J (2012) The pollen extract femal—a nonestrogenic alternative to hormone therapy in women with menopausal symptoms. Menopause 19:825–829. https://doi.org/10.1097/gme.0b013e31824017bc
Hidaka S, Okamoto Y, Miyazaki K, Uesugi T (2003) Evaluation of a soybean product fujiflavone P40 as an antiosteoporotic agent in rats. Phytother Res 17:112–119. https://doi.org/10.1002/ptr.1047
Ho HM, Chen R, Huang Y, Chen ZY (2002) Vascular effects of a soy leaves (Glycine max) extract and kaempferol glycosides in isolated rat carotid arteries. Planta Med 68:487–491. https://doi.org/10.1055/s-2002-32545
Hooshmand S, Khalil DA, Murillo G, Singletary K, Kamath SK, Arjmandi BH (2008) The combination of genistin and ipriflavone prevents mammary tumorigenesis and modulates lipid profile. Clin Nutr 27:643–648. https://doi.org/10.1016/j.clnu.2008.04.012
Hooshmand S, Juma S, Arjmandi BH (2010) Combination of genistin and fructooligosaccharides prevents bone loss in ovarian hormone deficiency. J Med Food 13:320–325. https://doi.org/10.1089/jmf.2009.0059
Hu Y, Ge C, Yuan W, Zhu R, Zhang W, Du L, Xue J (2010) Characterization of fermented black soybean natto inoculated with Bacillus natto during fermentation. J Sci Food Agric 90:1194–1202. https://doi.org/10.1002/jsfa.3947
Huang RY, Chou CC (2009) Stability of isoflavone isomers in steamed black soybeans and black soybean koji stored under different conditions. J Agric Food Chem 57:1927–1932. https://doi.org/10.1021/jf803702x
Indran IR, Tufo G, Pervaiz S, Brenner C (2011) Recent advances in apoptosis, mitochondria and drug resistance in cancer cells. Biochim Biophys Acta 1807:735–745. https://doi.org/10.1016/j.bbabio.2011.03.010
Ingawale DK, Mandlik SK, Naik SR (2014) Models of hepatotoxicity and the underlying cellular, biochemical and immunological mechanism(s): a critical discussion. Environ Toxicol Pharmacol 37:118–133. https://doi.org/10.1016/j.etap.2013.08.015
Ishwarya M, Narendhirakannan RT (2016) The advances in neurobiology. Adv Neurobiol 12:293–306. https://doi.org/10.1007/978-3-319-28383-8_15
Islam MA, Punt A, Spenkelink B, Murk AJ, Rolaf van Leeuwen FX, Rietjens IM (2014) Conversion of major soy isoflavone glucosides and aglycones in in vitro intestinal models. Mol Nutr Food Res 58:503–515. https://doi.org/10.1002/mnfr.201300390
Ji MX, Yu Q (2015) Primary osteoporosis in postmenopausal women. Chronic Dis Transl Med 1:9–13. https://doi.org/10.1016/j.cdtm.2015.02.006
Jin SE, Son YK, Min BS, Jung HA, Choi JS (2012) Anti-inflammatory and antioxidant activities of constituents isolated from Pueraria lobata roots. Arch Pharm Res 35:823–837. https://doi.org/10.1007/s12272-012-0508-x
Jung HA, Kim AR, Chung HY, Choi JS (2002) In vitro antioxidant activity of some selected Prunus species in Korea. Arch Pharm Res 25:865–872
Kao TK, Ou YC, Raung SL, Chen WY, Yen YJ, Lai CY, Chou ST, Chen CJ (2010) Graptopetalum paraguayense E. Walther leaf extracts protect against brain injury in ischemic rats. Am J Chin Med 38:495–516. https://doi.org/10.1142/S0192415X10008019
Kasparova M, Siatka T, Klimesova V, Dusek J (2012) New synthetic pyridine derivate as potential elicitor in production of isoflavonoids and flavonoids in Trifolium pratense L. suspension culture. Sci World J 2012:746412. https://doi.org/10.1100/2012/746412
Kato K, Takahashi S, Cui L, Toda T, Suzuki S, Futakuchi M, Sugiura S, Shirai T (2000) Suppressive effects of dietary genistin and daidzin on rat prostate carcinogenesis. Jpn J Cancer Res 91:786–791. https://doi.org/10.1111/j.1349-7006.2000.tb01014.x
Kelly RR, McDonald LT, Jensen NR, Sidles SJ, LaRue AC (2019) Impacts of psychological stress on osteoporosis: clinical implications and treatment interactions. Front Psychiatry 10:200. https://doi.org/10.3389/fpsyt.2019.00200
Kim JM, Yun-Choi HS (2008) Anti-platelet effects of flavonoids and flavonoid-glycosides from Sophora japonica. Arch Pharm Res 31:886–890. https://doi.org/10.1007/s12272-001-1242-1
Kim AR, Cho JY, Zou Y, Choi JS, Chung HY (2005) Flavonoids differentially modulate nitric oxide production pathways in lipopolysaccharide-activated RAW264.7 cells. Arch Pharm Res 28:297–304. https://doi.org/10.1007/bf02977796
Kim EY, Hong KB, Suh HJ, Choi HS (2015) Protective effects of germinated and fermented soybean extract against tert-butyl hydroperoxide-induced hepatotoxicity in HepG2 cells and in rats. Food Funct 6:3512–3521. https://doi.org/10.1039/c5fo00785b
Kirakosyan A, Kaufman PB, Chang SC, Warber S, Bolling S, Vardapetyan H (2006) Regulation of isoflavone production in hydroponically grown Pueraria montana (kudzu) by cork pieces, XAD-4, and methyl jasmonate. Plant Cell Rep 25:1387–1391. https://doi.org/10.1007/s00299-006-0198-2
Klejdus B, Mikelova R, Petrlova J, Potesil D, Adam V, Stiborova M, Hodek P, Vacek J, Kizek R, Kuban V (2005a) Determination of isoflavones in soy bits by fast column high-performance liquid chromatography coupled with UV-visible diode-array detection. J Chromatogr A 1084:71–79. https://doi.org/10.1016/j.chroma.2005.05.070
Klejdus B, Mikelova R, Petrlova J, Potesil D, Adam V, Stiborova M, Hodek P, Vacek J, Kizek R, Kuban V (2005b) Evaluation of isoflavone aglycon and glycoside distribution in soy plants and soybeans by fast column high-performance liquid chromatography coupled with a diode-array detector. J Agric Food Chem 53:5848–5852. https://doi.org/10.1021/jf0502754
Klejdus B, Vacek J, Benesova L, Kopecky J, Lapcik O, Kuban V (2007) Rapid-resolution HPLC with spectrometric detection for the determination and identification of isoflavones in soy preparations and plant extracts. Anal Bioanal Chem 389:2277–2285. https://doi.org/10.1007/s00216-007-1606-3
Ko EA, Park WS, Son YK, Kim DH, Kim N, Kim HK, Choi TH, Jung ID, Park YM, Han J (2009) The effect of tyrosine kinase inhibitor genistein on voltage-dependent K+ channels in rabbit coronary arterial smooth muscle cells. Vascul Pharmacol 50:51–56. https://doi.org/10.1016/j.vph.2008.09.004
Kojima T, Uesugi T, Toda T, Miura Y, Yagasaki K (2002) Hypolipidemic action of the soybean isoflavones genistein and genistin in glomerulonephritic rats. Lipids 37:261–265. https://doi.org/10.1007/s11745-002-0889-z
Kreutzberg GW (1996) Microglia: a sensor for pathological events in the CNS. Trends Neurosci 19:312–318
Krizova L, Dadakova K, Kasparovska J, Kasparovsky T (2019) Isoflavones. Molecules. https://doi.org/10.3390/molecules24061076
Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA (1998) Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 139:4252–4263. https://doi.org/10.1210/endo.139.10.6216
Lai HH, Yen GC (2002) Inhibitory effect of isoflavones on peroxynitrite-mediated low-density lipoprotein oxidation. Biosci Biotechnol Biochem 66:22–28. https://doi.org/10.1271/bbb.66.22
Lanou AJ (2011) Soy foods: are they useful for optimal bone health? Ther Adv Musculoskelet Dis 3:293–300. https://doi.org/10.1177/1759720X11417749
Lapcik O, Honys D, Koblovska R, Mackova Z, Vitkova M, Klejdus B (2006) Isoflavonoids are present in Arabidopsis thaliana despite the absence of any homologue to known isoflavonoid synthases. Plant Physiol Biochem 44:106–114. https://doi.org/10.1016/j.plaphy.2005.11.006
Lazo JS, Kondo Y, Dellapiazza D, Michalska AE, Choo KH, Pitt BR (1995) Enhanced sensitivity to oxidative stress in cultured embryonic cells from transgenic mice deficient in metallothionein I and II genes. J Biol Chem 270:5506–5510. https://doi.org/10.1074/jbc.270.10.5506
Lee SJ, Ahn JK, Khanh TD, Chun SC, Kim SL, Ro HM, Song HK, Chung IM (2007) Comparison of isoflavone concentrations in soybean (Glycine max (L.) Merrill) sprouts grown under two different light conditions. J Agric Food Chem 55:9415–9421. https://doi.org/10.1021/jf071861v
Lee GA, Crawford GW, Liu L, Sasaki Y, Chen X (2011) Archaeological soybean (Glycine max) in East Asia: does size matter? PLoS ONE 6:e26720. https://doi.org/10.1371/journal.pone.0026720
Li XH, Zhang JC, Sui SF, Yang MS (2005) Effect of daidzin, genistin, and glycitin on osteogenic and adipogenic differentiation of bone marrow stromal cells and adipocytic transdifferentiation of osteoblasts. Acta Pharmacol Sin 26:1081–1086. https://doi.org/10.1111/j.1745-7254.2005.00161.x
Li G, Zhang Q, Wang Y (2010) Chemical constituents from roots of Pueraria lobata. Zhongguo Zhong Yao Za Zhi 35:3156–3160
Lian Z, Niwa K, Gao J, Tagami K, Onczi K, Mori H, Tamaya T (2004) Soybean isoflavones inhibit estrogen-stimulated gene expression in mouse uteri. Eur J Gynaecol Oncol 25:311–314
Liu Y, Zhang X, Kelsang N, Tu G, Kong D, Lu J, Zhang Y, Liang H, Tu P, Zhang Q (2018) Structurally diverse cytotoxic dimeric chalcones from Oxytropis chiliophylla. J Nat Prod 81:307–315. https://doi.org/10.1021/acs.jnatprod.7b00736
Loos RJ, Rankinen T (2005) Gene-diet interactions on body weight changes. J Am Diet Assoc 105:S29–34. https://doi.org/10.1016/j.jada.2005.02.015
MacDougald OA, Lane MD (1995) Transcriptional regulation of gene expression during adipocyte differentiation. Annu Rev Biochem 64:345–373. https://doi.org/10.1146/annurev.bi.64.070195.002021
Maggioni S, Bagnati R, Pandelova M, Schramm KW, Benfenati E (2013) Genistein and dicarboximide fungicides in infant formulae from the EU market. Food Chem 136:116–119. https://doi.org/10.1016/j.foodchem.2012.07.094
Meng M, Yan L, Song X, Zhang Q, Wang Z (2011) HPLC characteristic fingerprint of Moghania philippinensis root. Zhongguo Zhong Yao Za Zhi 36:1202–1206
Messina M (2016) Soy and health update: evaluation of the clinical and epidemiologic literature. Nutrients. https://doi.org/10.3390/nu8120754
Mishra SI, Dickerson V, Najm W (2003) Phytoestrogens and breast cancer prevention: what is the evidence? Am J Obstet Gynecol 188:S66–70. https://doi.org/10.1067/mob.2003.405
Mittal N, Hota D, Dutta P, Bhansali A, Suri V, Aggarwal N, Marwah RK, Chakrabarti A (2011) Evaluation of effect of isoflavone on thyroid economy & autoimmunity in oophorectomised women: a randomised, double-blind, placebo-controlled trial. Indian J Med Res 133:633–640
Morrison JH, Brinton RD, Schmidt PJ, Gore AC (2006) Estrogen, menopause, and the aging brain: how basic neuroscience can inform hormone therapy in women. J Neurosci 26:10332–10348. https://doi.org/10.1523/JNEUROSCI.3369-06.2006
Mun SC, Mun GS (2015) Dynamics of phytoestrogen, isoflavonoids, and its isolation from stems of Pueraria lobata (Willd.) Ohwi growing in Democratic People's Republic of Korea. J Food Drug Anal 23:538–544. https://doi.org/10.1016/j.jfda.2015.04.003
Nakazawa K, Ohno Y (2003) Block by phytoestrogens of recombinant human neuronal nicotinic receptors. J Pharmacol Sci 93:118–121
Nih Consensus Development Panel on Osteoporosis Prevention D, Therapy (2001) Osteoporosis prevention, diagnosis, and therapy. JAMA 285:785–795. https://doi.org/10.1001/jama.285.6.785
Norbury CJ, Hickson ID (2001) Cellular responses to DNA damage. Annu Rev Pharmacol Toxicol 41:367–401. https://doi.org/10.1146/annurev.pharmtox.41.1.367
Ondricek AJ, Kashyap AK, Thamake SI, Vishwanatha JK (2012) A comparative study of phytoestrogen action in mitigating apoptosis induced by oxidative stress. In Vivo 26:765–775
Panche AN, Diwan AD, Chandra SR (2016) Flavonoids: an overview. J Nutr Sci 5:e47. https://doi.org/10.1017/jns.2016.41
Park M, Jeong MK, Kim M, Lee J (2012) Modification of isoflavone profiles in a fermented soy food with almond powder. J Food Sci 77:C128–C134. https://doi.org/10.1111/j.1750-3841.2011.02504.x
Phromnoi K, Yodkeeree S, Anuchapreeda S, Limtrakul P (2009) Inhibition of MMP-3 activity and invasion of the MDA-MB-231 human invasive breast carcinoma cell line by bioflavonoids. Acta Pharmacol Sin 30:1169–1176. https://doi.org/10.1038/aps.2009.107
Plewa MJ, Berhow MA, Vaughn SF, Woods EJ, Rundell M, Naschansky K, Bartolini S, Wagner ED (2001) Isolating antigenotoxic components and cancer cell growth suppressors from agricultural by-products. Mutat Res 480–481:109–120. https://doi.org/10.1016/s0027-5107(01)00174-9
Pongkitwitoon B, Sakamoto S, Tanaka H, Tsuchihashi R, Kinjo J, Morimoto S, Putalun W (2010) Enzyme-linked immunosorbent assay for total isoflavonoids in Pueraria candollei using anti-puerarin and anti-daidzin polyclonal antibodies. Planta Med 76:831–836. https://doi.org/10.1055/s-0029-1240725
Qu LP, Fan GR, Peng JY, Mi HM (2007) Isolation of six isoflavones from Semen sojae praeparatum by preparative HPLC. Fitoterapia 78:200–204. https://doi.org/10.1016/j.fitote.2006.11.002
Quan J, Yin X, Kanazawa T (2009) Effect of soybean hypocotyl extract on lipid peroxidation in GK rats. J Clin Biochem Nutr 44:212–217. https://doi.org/10.3164/jcbn.07-53
Ramana KV, Srivastava S, Singhal SS (2017) Lipid peroxidation products in human health and disease 2016. Oxid Med Cell Longev 2017:2163285. https://doi.org/10.1155/2017/2163285
Reiter E, Beck V, Medjakovic S, Mueller M, Jungbauer A (2009) Comparison of hormonal activity of isoflavone-containing supplements used to treat menopausal complaints. Menopause 16:1049–1060. https://doi.org/10.1097/gme.0b013e31819c146c
Rizk ML, Zou L, Savic RM, Dooley KE (2017) Importance of drug pharmacokinetics at the site of action. Clin Transl Sci 10:133–142. https://doi.org/10.1111/cts.12448
Rostagno MA, Palma M, Barroso CG (2003) Ultrasound-assisted extraction of soy isoflavones. J Chromatogr A 1012:119–128. https://doi.org/10.1016/s0021-9673(03)01184-1
Russo A, Cardile V, Lombardo L, Vanella L, Acquaviva R (2006) Genistin inhibits UV light-induced plasmid DNA damage and cell growth in human melanoma cells. J Nutr Biochem 17:103–108. https://doi.org/10.1016/j.jnutbio.2005.05.011
Sacks FM, Lichtenstein A, Van Horn L, Harris W, Kris-Etherton P, Winston M, American Heart Association Nutrition C (2006) Soy protein, isoflavones, and cardiovascular health: an American Heart Association Science Advisory for professionals from the Nutrition Committee. Circulation 113:1034–1044. https://doi.org/10.1161/CIRCULATIONAHA.106.171052
Sepehr E, Robertson P, Gilani GS, Cooke G, Lau BP (2006) An accurate and reproducible method for the quantitative analysis of isoflavones and their metabolites in rat plasma using liquid chromatography/mass spectrometry combined with photodiode array detection. J AOAC Int 89:1158–1167
Serrano-Pozo A, Frosch MP, Masliah E, Hyman BT (2011) Neuropathological alterations in Alzheimer disease. Cold Spring Harb Perspect Med 1:a006189. https://doi.org/10.1101/cshperspect.a006189
Setchell KD, Brzezinski A, Brown NM, Desai PB, Melhem M, Meredith T, Zimmer-Nechimias L, Wolfe B, Cohen Y, Blatt Y (2005) Pharmacokinetics of a slow-release formulation of soybean isoflavones in healthy postmenopausal women. J Agric Food Chem 53:1938–1944. https://doi.org/10.1021/jf0488099
Sherrill JD, Sparks M, Dennis J, Mansour M, Kemppainen BW, Bartol FF, Morrison EE, Akingbemi BT (2010) Developmental exposures of male rats to soy isoflavones impact Leydig cell differentiation. Biol Reprod 83:488–501. https://doi.org/10.1095/biolreprod.109.082685
Shi H, Nam PK, Ma Y (2010) Comprehensive profiling of isoflavones, phytosterols, tocopherols, minerals, crude protein, lipid, and sugar during soybean (Glycine max) germination. J Agric Food Chem 58:4970–4976. https://doi.org/10.1021/jf100335j
Sibao C, Dajian Y, Shilin C, Hongx X, Chan AS (2007) Seasonal variations in the isoflavonoids of radix Puerariae. Phytochem Anal 18:245–250
Siegel RL, Miller KD, Jemal A (2016) Cancer statistics, 2016. CA Cancer J Clin 66:7–30. https://doi.org/10.3322/caac.21332
Singh AV, Franke AA, Blackburn GL, Zhou JR (2006) Soy phytochemicals prevent orthotopic growth and metastasis of bladder cancer in mice by alterations of cancer cell proliferation and apoptosis and tumor angiogenesis. Cancer Res 66:1851–1858. https://doi.org/10.1158/0008-5472.CAN-05-1332
Son E, Yoon JM, An BJ, Lee YM, Cha J, Chi GY, Kim DS (2019) Comparison among activities and isoflavonoids from Pueraria thunbergiana aerial parts and root. Molecules. https://doi.org/10.3390/molecules24050912
Spinelli MG (2004) Depression and hormone therapy. Clin Obstet Gynecol 47:428–436. https://doi.org/10.1097/00003081-200406000-00019
Sun YG, Wang SS, Feng JT, Xue XY, Liang XM (2008) Two new isoflavone glycosides from Pueraria lobata. J Asian Nat Prod Res 10:729–733. https://doi.org/10.1080/10286020802016198
Szeja W, Grynkiewicz G, Rusin A (2017) Isoflavones, their glycosides and glycoconjugates. Synthesis and biological activity. Curr Org Chem 21:218–235. https://doi.org/10.2174/1385272820666160928120822
Tang YP, Zhu HX, Duan JA (2008) Two new isoflavone triglycosides from the small branches of Sophora japonica. J Asian Nat Prod Res 10:65–70. https://doi.org/10.1080/10286020701273858
Tsai HS, Huang LJ, Lai YH, Chang JC, Lee RS, Chiou RY (2007) Solvent effects on extraction and HPLC analysis of soybean isoflavones and variations of isoflavone compositions as affected by crop season. J Agric Food Chem 55:7712–7715. https://doi.org/10.1021/jf071010n
Uesugi T, Toda T, Tsuji K, Ishida H (2001) Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin. Biol Pharm Bull 24:368–372. https://doi.org/10.1248/bpb.24.368
Vitor RF, Mota-Filipe H, Teixeira G, Borges C, Rodrigues AI, Teixeira A, Paulo A (2004) Flavonoids of an extract of Pterospartum tridentatum showing endothelial protection against oxidative injury. J Ethnopharmacol 93:363–370. https://doi.org/10.1016/j.jep.2004.04.003
Wang Z, Li W, Gao Y, Liu J (2010) Simultaneous determination of nine isoflavonoids in Huangqi Gegen decoction by high performance liquid chromatography. Zhongguo Zhong Yao Za Zhi 35:2689–2692
Wang BS, Juang LJ, Yang JJ, Chen LY, Tai HM, Huang MH (2012) Antioxidant and antityrosinase activity of Flemingia macrophylla and glycine tomentella roots. Evid Based Complement Alternat Med 2012:431081. https://doi.org/10.1155/2012/431081
Wang DJ, Khan MS, Cui L, Song XY, Zhu H, Ma TY, Li XY, Sun R (2019) A novel method for the highly efficient biotransformation of genistein from genistin using a high-speed counter-current chromatography bioreactor. RSC Adv 9:4892–4899. https://doi.org/10.1039/c8ra10629k
Wong RW, Rabie AB (2010) Effect of genistin on bone formation. Front Biosci (Elite Ed) 2:764–770
Xue Y, Yu J, Song X (2009) Hydrolysis of soy isoflavone glycosides by recombinant beta-glucosidase from hyperthermophile Thermotoga maritima. J Ind Microbiol Biotechnol 36:1401–1408. https://doi.org/10.1007/s10295-009-0626-8
Yang X, Deng Z, Wang J, Ding M (2006) Preparation of soybean isoflavone glucosides by reversed-phase high performance liquid chromatography. Se Pu 24:363–366
Yasuda T, Endo M, Kon-no T, Kato T, Mitsuzuka M, Ohsawa K (2005) Antipyretic, analgesic and muscle relaxant activities of pueraria isoflavonoids and their metabolites from Pueraria lobata Ohwi-a traditional Chinese drug. Biol Pharm Bull 28:1224–1228. https://doi.org/10.1248/bpb.28.1224
Yeom SJ, Kim BN, Kim YS, Oh DK (2012) Hydrolysis of isoflavone glycosides by a thermostable beta-glucosidase from Pyrococcus furiosus. J Agric Food Chem 60:1535–1541. https://doi.org/10.1021/jf204432g
You J, Jiang D (2010) Effect of genistin on proliferative vitreoretinopathy. Zhong Nan Da Xue Xue Bao Yi Xue Ban 35:749–753. https://doi.org/10.3969/j.issn.1672-7347.2010.07.017
Yu J, Bi X, Yu B, Chen D (2016) Isoflavones: anti-inflammatory benefit and possible caveats. Nutrients. https://doi.org/10.3390/nu8060361
Yuan D, Xie YY, Bai X, Wu X, Yang JY, Wu CF (2009) Inhibitory activity of isoflavones of Pueraria flowers on nitric oxide production from lipopolysaccharide-activated primary rat microglia. J Asian Nat Prod Res 11:471–481. https://doi.org/10.1080/10286020902819822
Zaheer K, Humayoun Akhtar M (2017) An updated review of dietary isoflavones: Nutrition, processing, bioavailability and impacts on human health. Crit Rev Food Sci Nutr 57:1280–1293. https://doi.org/10.1080/10408398.2014.989958
Zhang D, Ren Y, Dai S, Liu W, Li G (2009) Isoflavones from vines of Pueraria lobata. Zhongguo Zhong Yao Za Zhi 34:3217–3220
Zhang Z, Li S, Jiang J, Yu P, Liang J, Wang Y (2010) Preventive effects of Flos perariae (Gehua) water extract and its active ingredient puerarin in rodent alcoholism models. Chin Med 5:36. https://doi.org/10.1186/1749-8546-5-36
Zhang HY, Wang HL, Zhong GY, Zhu JX (2018) Molecular mechanism and research progress on pharmacology of traditional Chinese medicine in liver injury. Pharm Biol 56:594–611. https://doi.org/10.1080/13880209.2018.1517185
Zhao C, Chan HY, Yuan D, Liang Y, Lau TY, Chau FT (2011) Rapid simultaneous determination of major isoflavones of Pueraria lobata and discriminative analysis of its geographical origins by principal component analysis. Phytochem Anal 22:503–508. https://doi.org/10.1002/pca.1308
Zhao L, Chen Q, Diaz Brinton R (2002) Neuroprotective and neurotrophic efficacy of phytoestrogens in cultured hippocampal neurons. Exp Biol Med (Maywood) 227:509–519. https://doi.org/10.1177/153537020222700716
Zhao JH, Arao Y, Sun SJ, Kikuchi A, Kayama F (2006) Oral administration of soy-derived genistin suppresses lipopolysaccharide-induced acute liver inflammation but does not induce thymic atrophy in the rat. Life Sci 78:812–819. https://doi.org/10.1016/j.lfs.2005.05.104
Zhou JR, Yu L, Zhong Y, Nassr RL, Franke AA, Gaston SM, Blackburn GL (2002) Inhibition of orthotopic growth and metastasis of androgen-sensitive human prostate tumors in mice by bioactive soybean components. Prostate 53:143–153. https://doi.org/10.1002/pros.10141
Zhou YY, Luo SH, Yi TS, Li CH, Luo Q, Hua J, Liu Y, Li SH (2011) Secondary metabolites from Glycine soja and their growth inhibitory effect against Spodoptera litura. J Agric Food Chem 59:6004–6010. https://doi.org/10.1021/jf200821p
Zhu Y, Yao Y, Shi Z, Everaert N, Ren G (2018) Synergistic effect of bioactive anticarcinogens from soybean on anti-proliferative activity in MDA-MB-231 and MCF-7 human breast cancer cells in vitro. Molecules. https://doi.org/10.3390/molecules23071557
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Islam, A., Islam, M.S., Uddin, M.N. et al. The potential health benefits of the isoflavone glycoside genistin. Arch. Pharm. Res. 43, 395–408 (2020). https://doi.org/10.1007/s12272-020-01233-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-020-01233-2