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Chemical Compound Review

Genistin     5-hydroxy-3-(4- hydroxyphenyl)-7- [(2S,3R,4S...

Synonyms: Genistine, Genistoside, AC1NQYEA, Genistin (8CI), SureCN62148, ...
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Disease relevance of NSC 5112

  • Dietary genistin stimulates growth of estrogen-dependent breast cancer tumors similar to that observed with genistein [1].
  • The present study was designed to determine if a diet enriched in the phytoestrogen isoflavones, genistin and daidzin, would alter the antigen-induced cellular infiltration, particularly eosinophilia, characteristic of a guinea pig model of asthma [2].
  • RESULTS: In male SCID mice orthotopically implanted with the androgen-sensitive human prostate cell line LNCaP, dietary supplements of soy protein, genistin, and SPC reduced primary tumor weight by 42% (P = 0.07), 57% (P < 0.05) and 70% (P < 0.005), respectively [3].
  • Thus, the present data suggest that genistin and daidzin possess anti-cancer effects at relatively early stages of prostate cancer development, providing experimental support for epidemiological findings [4].
  • The enzymatic modification of genistin to enhance its water solubility was studied using two glycosyltransferases, cyclodextrin glucanotransferase from alkalophilic Bacillus sp. I-5 and 4-alpha-glucanotransferase from Thermus scotoductus [5].

High impact information on NSC 5112


Biological context of NSC 5112


Anatomical context of NSC 5112


Associations of NSC 5112 with other chemical compounds


Gene context of NSC 5112

  • The relative expression of pS2, progesterone receptor and cyclin D1 was increased in animals consuming the Novasoy(R), mixed isoflavones and genistin [21].
  • Genistin showed inhibitory effects on IL-5 and IL-3 bioactivities, but did not inhibit GM-CSF and IL-6 bioactivities [22].
  • The aim of this study was to investigate the effect of phloridzin, an inhibitor of the sodium-dependent glucose transporter (SGLT1), on genistin absorption and metabolism [17].
  • The temperature dependence of genistin loss followed the Arrhenius relation with activation energies of 7.2 kcal/mol at ambient temperatures and 17.6 kcal/mol at elevated temperatures [23].
  • Genistin has antioxidant activities; however, its insolubility in water often limits its biological availability in vivo [24].

Analytical, diagnostic and therapeutic context of NSC 5112


  1. Dietary genistin stimulates growth of estrogen-dependent breast cancer tumors similar to that observed with genistein. Allred, C.D., Ju, Y.H., Allred, K.F., Chang, J., Helferich, W.G. Carcinogenesis (2001) [Pubmed]
  2. Dietary phytoestrogens have anti-inflammatory activity in a guinea pig model of asthma. Regal, J.F., Fraser, D.G., Weeks, C.E., Greenberg, N.A. Proc. Soc. Exp. Biol. Med. (2000) [Pubmed]
  3. Inhibition of orthotopic growth and metastasis of androgen-sensitive human prostate tumors in mice by bioactive soybean components. Zhou, J.R., Yu, L., Zhong, Y., Nassr, R.L., Franke, A.A., Gaston, S.M., Blackburn, G.L. Prostate (2002) [Pubmed]
  4. Suppressive effects of dietary genistin and daidzin on rat prostate carcinogenesis. Kato, K., Takahashi, S., Cui, L., Toda, T., Suzuki, S., Futakuchi, M., Sugiura, S., Shirai, T. Jpn. J. Cancer Res. (2000) [Pubmed]
  5. Glycosylation of genistin into soluble inclusion complex form of cyclic glucans by enzymatic modification. Li, D., Roh, S.A., Shim, J.H., Mikami, B., Baik, M.Y., Park, C.S., Park, K.H. J. Agric. Food Chem. (2005) [Pubmed]
  6. Soy phytochemicals prevent orthotopic growth and metastasis of bladder cancer in mice by alterations of cancer cell proliferation and apoptosis and tumor angiogenesis. Singh, A.V., Franke, A.A., Blackburn, G.L., Zhou, J.R. Cancer Res. (2006) [Pubmed]
  7. Inhibition of murine bladder tumorigenesis by soy isoflavones via alterations in the cell cycle, apoptosis, and angiogenesis. Zhou, J.R., Mukherjee, P., Gugger, E.T., Tanaka, T., Blackburn, G.L., Clinton, S.K. Cancer Res. (1998) [Pubmed]
  8. Erythropoietin receptor-mediated inhibition of exocytotic glutamate release confers neuroprotection during chemical ischemia. Kawakami, M., Sekiguchi, M., Sato, K., Kozaki, S., Takahashi, M. J. Biol. Chem. (2001) [Pubmed]
  9. Interleukin-1-induced calcium flux in human fibroblasts is mediated through focal adhesions. Arora, P.D., Ma, J., Min, W., Cruz, T., McCulloch, C.A. J. Biol. Chem. (1995) [Pubmed]
  10. Evidence for lack of absorption of soy isoflavone glycosides in humans, supporting the crucial role of intestinal metabolism for bioavailability. Setchell, K.D., Brown, N.M., Zimmer-Nechemias, L., Brashear, W.T., Wolfe, B.E., Kirschner, A.S., Heubi, J.E. Am. J. Clin. Nutr. (2002) [Pubmed]
  11. Flavonoid glucosides are hydrolyzed and thus activated in the oral cavity in humans. Walle, T., Browning, A.M., Steed, L.L., Reed, S.G., Walle, U.K. J. Nutr. (2005) [Pubmed]
  12. Soybean isoflavones, genistein and genistin, inhibit rat myoblast proliferation, fusion and myotube protein synthesis. Ji, S., Willis, G.M., Frank, G.R., Cornelius, S.G., Spurlock, M.E. J. Nutr. (1999) [Pubmed]
  13. Absorption and metabolism of genistin in the isolated rat small intestine. Andlauer, W., Kolb, J., Fürst, P. FEBS Lett. (2000) [Pubmed]
  14. Effects of a standardized soy extract on hot flushes: a multicenter, double-blind, randomized, placebo-controlled study. Faure, E.D., Chantre, P., Mares, P. Menopause (New York, N.Y.) (2002) [Pubmed]
  15. Vascular effects of a soy leaves (Glycine max) extract and kaempferol glycosides in isolated rat carotid arteries. Ho, H.M., Chen, R., Huang, Y., Chen, Z.Y. Planta Med. (2002) [Pubmed]
  16. Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver beta-glucosidase activity. Day, A.J., DuPont, M.S., Ridley, S., Rhodes, M., Rhodes, M.J., Morgan, M.R., Williamson, G. FEBS Lett. (1998) [Pubmed]
  17. Phloridzin improves absorption of genistin in isolated rat small intestine. Andlauer, W., Kolb, J., Fürst, P. Clinical nutrition (Edinburgh, Scotland) (2004) [Pubmed]
  18. Interactions of genistein and related isoflavones with lipid micelles. Whaley, W.L., Rummel, J.D., Kastrapeli, N. Langmuir : the ACS journal of surfaces and colloids. (2006) [Pubmed]
  19. Isoflavone levels in five soybean (Glycine max) genotypes are altered by phytochrome-mediated light treatments. Kirakosyan, A., Kaufman, P., Nelson, R.L., Kasperbauer, M.J., Duke, J.A., Seymour, E., Chang, S.C., Warber, S., Bolling, S. J. Agric. Food Chem. (2006) [Pubmed]
  20. Selective inhibitors of terminal deoxyribonucleotidyltransferase (TdT): baicalin and genistin. Uchiyama, Y., Tagami, J., Kamisuki, S., Kasai, N., Oshige, M., Chiku, H., Ibe, S., Koiwai, O., Sugawara, F., Sakaguchi, K. Biochim. Biophys. Acta (2005) [Pubmed]
  21. Soy processing influences growth of estrogen-dependent breast cancer tumors. Allred, C.D., Allred, K.F., Ju, Y.H., Goeppinger, T.S., Doerge, D.R., Helferich, W.G. Carcinogenesis (2004) [Pubmed]
  22. Differential inhibitory effects of sophoricoside analogs on bioactivity of several cytokines. Yun, J., Lee, C.K., Chang, I.M., Takatsu, K., Hirano, T., Min, K.R., Lee, M.K., Kim, Y. Life Sci. (2000) [Pubmed]
  23. Stability of isoflavones in soy milk stored at elevated and ambient temperatures. Eisen, B., Ungar, Y., Shimoni, E. J. Agric. Food Chem. (2003) [Pubmed]
  24. Water-soluble genistin glycoside isoflavones up-regulate antioxidant metallothionein expression and scavenge free radicals. Chung, M.J., Kang, A.Y., Lee, K.M., Oh, E., Jun, H.J., Kim, S.Y., Auh, J.H., Moon, T.W., Lee, S.J., Park, K.H. J. Agric. Food Chem. (2006) [Pubmed]
  25. Stabilities of daidzin, glycitin, genistin, and generation of derivatives during heating. Xu, Z., Wu, Q., Godber, J.S. J. Agric. Food Chem. (2002) [Pubmed]
  26. Oral administration of soy-derived genistin suppresses lipopolysaccharide-induced acute liver inflammation but does not induce thymic atrophy in the rat. Zhao, J.H., Arao, Y., Sun, S.J., Kikuchi, A., Kayama, F. Life Sci. (2006) [Pubmed]
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