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Chemical Compound Review

AGN-PC-00Q48W     4-(7-hydroxychroman-3-yl)-2- methoxy...

Synonyms: AC1NS0BY
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Disease relevance of Isoflavonoid

  • Activation of the cell cycle machinery and the isoflavonoid biosynthesis pathway by active Rhizobium meliloti Nod signal molecules in Medicago microcallus suspensions [1].
  • Genistein, a natural isoflavonoid found in soybean products, has been proposed to be associated with a lower rate of breast cancer in Asian women [2].
  • Thus, isoflavonoid-induced inhibition of bone resorption may contribute to the low risk of osteoporosis in Asian women [3].
  • Isoflavones are synthesized by 1,2-elimination of water from 2-hydroxyisoflavanones, the first intermediate with the isoflavonoid skeleton, but details of this dehydration have been unclear [4].
  • According to our measurements, with adjustment for body weight, isoflavonoid exposure is 4-6 times higher in infants fed soy-based formula than in adults eating a diet rich in soyfoods (approximately 30 g/d) [5].

Psychiatry related information on Isoflavonoid

  • All three isoflavonoid compounds were effective in suppressing voluntary alcohol consumption by the P rats [6].
  • Effects of the estrogenic plant isoflavonoid coumestrol (COUM) on locomotor activity and fear-related behaviors in both the absence and the presence of estradiol benzoate (EB) were examined in adult ovariectomized Swiss-Webster mice [7].

High impact information on Isoflavonoid


Chemical compound and disease context of Isoflavonoid


Biological context of Isoflavonoid


Anatomical context of Isoflavonoid


Associations of Isoflavonoid with other chemical compounds


Gene context of Isoflavonoid


Analytical, diagnostic and therapeutic context of Isoflavonoid

  • Furthermore, protein gel blot analysis and confocal microscopy of a transiently expressed IOMT-green fluorescent protein fusion in alfalfa leaves show that the operationally soluble IOMT localizes to endomembranes after elicitation of the isoflavonoid pathway [37].
  • The phytoestrogenic isoflavonoid equol is known to protect against solar-simulated UV radiation-induced inflammation, immunosuppression, and skin carcinogenesis [38].
  • Capillary electrophoresis was examined as an alternative to current high-performance liquid chromatography (HPLC) methods to generate isoflavonoid profiles [39].
  • Soy isoflavonoids have well-established estrogenic properties in cell culture and rodent models, raising concerns that high isoflavonoid intake may promote development of uterine and breast cancers [40].
  • HPLC analysis of isoflavonoid-derived metabolites of the phenylpropanoid pathway revealed similar total constitutive levels, but varying relative proportions and types, in roots of the resistant and susceptible plants [41].


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  2. Inactivation of NF-kappaB by genistein is mediated via Akt signaling pathway in breast cancer cells. Gong, L., Li, Y., Nedeljkovic-Kurepa, A., Sarkar, F.H. Oncogene (2003) [Pubmed]
  3. Effects of phytoestrogens on bone turnover in postmenopausal women with a history of breast cancer. Nikander, E., Metsä-Heikkilä, M., Ylikorkala, O., Tiitinen, A. J. Clin. Endocrinol. Metab. (2004) [Pubmed]
  4. Molecular and biochemical characterization of 2-hydroxyisoflavanone dehydratase. Involvement of carboxylesterase-like proteins in leguminous isoflavone biosynthesis. Akashi, T., Aoki, T., Ayabe, S. Plant Physiol. (2005) [Pubmed]
  5. Isoflavones in human breast milk and other biological fluids. Franke, A.A., Custer, L.J., Tanaka, Y. Am. J. Clin. Nutr. (1998) [Pubmed]
  6. Isoflavonoid compounds extracted from Pueraria lobata suppress alcohol preference in a pharmacogenetic rat model of alcoholism. Lin, R.C., Guthrie, S., Xie, C.Y., Mai, K., Lee, D.Y., Lumeng, L., Li, T.K. Alcohol. Clin. Exp. Res. (1996) [Pubmed]
  7. Effects of the phytoestrogen coumestrol on locomotor and fear-related behaviors in female mice. Garey, J., Morgan, M.A., Frohlich, J., McEwen, B.S., Pfaff, D.W. Hormones and behavior. (2001) [Pubmed]
  8. Molecular cloning, characterization, and elicitation of acetyl-CoA carboxylase from alfalfa. Shorrosh, B.S., Dixon, R.A., Ohlrogge, J.B. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  9. Flavonoids, dietary-derived inhibitors of cell proliferation and in vitro angiogenesis. Fotsis, T., Pepper, M.S., Aktas, E., Breit, S., Rasku, S., Adlercreutz, H., Wähälä, K., Montesano, R., Schweigerer, L. Cancer Res. (1997) [Pubmed]
  10. Arabidopsis thaliana NADPH oxidoreductase homologs confer tolerance of yeasts toward the thiol-oxidizing drug diamide. Babiychuk, E., Kushnir, S., Belles-Boix, E., Van Montagu, M., Inzé, D. J. Biol. Chem. (1995) [Pubmed]
  11. A binuclear zinc transcription factor binds the host isoflavonoid-responsive element in a fungal cytochrome p450 gene responsible for detoxification. Khan, R., Tan, R., Mariscal, A.G., Straney, D. Mol. Microbiol. (2003) [Pubmed]
  12. Transcriptome Analysis Reveals a Critical Role of CHS7 and CHS8 Genes for Isoflavonoid Synthesis in Soybean Seeds. Dhaubhadel, S., Gijzen, M., Moy, P., Farhangkhoee, M. Plant Physiol. (2007) [Pubmed]
  13. Activities and mechanisms of action of halogen-substituted flavanoids against poliovirus type 2 infection in vitro. Conti, C., Genovese, D., Santoro, R., Stein, M.L., Orsi, N., Fiore, L. Antimicrob. Agents Chemother. (1990) [Pubmed]
  14. Metabolic engineering: prospects for crop improvement through the genetic manipulation of phenylpropanoid biosynthesis and defense responses--a review. Dixon, R.A., Lamb, C.J., Masoud, S., Sewalt, V.J., Paiva, N.L. Gene (1996) [Pubmed]
  15. Isoliquiritigenin, a strong nod gene- and glyceollin resistance-inducing flavonoid from soybean root exudate. Kape, R., Parniske, M., Brandt, S., Werner, D. Appl. Environ. Microbiol. (1992) [Pubmed]
  16. Inhibition of cellular phosphatidylinositol turnover by psi-tectorigenin. Imoto, M., Yamashita, T., Sawa, T., Kurasawa, S., Naganawa, H., Takeuchi, T., Bao-quan, Z., Umezawa, K. FEBS Lett. (1988) [Pubmed]
  17. Competitive inhibition by genistein and ATP dependence of daunorubicin transport in intact MRP overexpressing human small cell lung cancer cells. Versantvoort, C.H., Broxterman, H.J., Lankelma, J., Feller, N., Pinedo, H.M. Biochem. Pharmacol. (1994) [Pubmed]
  18. Free radical scavenging action of the natural polyamine spermine in rat liver mitochondria. Sava, I.G., Battaglia, V., Rossi, C.A., Salvi, M., Toninello, A. Free Radic. Biol. Med. (2006) [Pubmed]
  19. Indole-3-carbinol is a negative regulator of estrogen. Auborn, K.J., Fan, S., Rosen, E.M., Goodwin, L., Chandraskaren, A., Williams, D.E., Chen, D., Carter, T.H. J. Nutr. (2003) [Pubmed]
  20. Inhibition of in vitro microsomal lipid peroxidation by isoflavonoids. Jha, H.C., von Recklinghausen, G., Zilliken, F. Biochem. Pharmacol. (1985) [Pubmed]
  21. Isoflavonoids do not inhibit in vivo lipid peroxidation in subjects with high-normal blood pressure. Hodgson, J.M., Puddey, I.B., Croft, K.D., Mori, T.A., Rivera, J., Beilin, L.J. Atherosclerosis (1999) [Pubmed]
  22. Absorption and metabolism of genistein in isolated rat small intestine. Andlauer, W., Kolb, J., Stehle, P., Fürst, P. J. Nutr. (2000) [Pubmed]
  23. Soy isoflavonoid equol modulates the growth of benign and malignant prostatic epithelial cells in vitro. Hedlund, T.E., Johannes, W.U., Miller, G.J. Prostate (2003) [Pubmed]
  24. Stress responses in alfalfa (Medicago sativa L.) XIX. Transcriptional activation of oxidative pentose phosphate pathway genes at the onset of the isoflavonoid phytoalexin response. Fahrendorf, T., Ni, W., Shorrosh, B.S., Dixon, R.A. Plant Mol. Biol. (1995) [Pubmed]
  25. Daidzein enhances osteoblast growth that may be mediated by increased bone morphogenetic protein (BMP) production. Jia, T.L., Wang, H.Z., Xie, L.P., Wang, X.Y., Zhang, R.Q. Biochem. Pharmacol. (2003) [Pubmed]
  26. 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]
  27. Effect of dietary soy isoflavone aglycones on the urinary 16alpha-to-2-hydroxyestrone ratio in C3H/HeJ mice. Kishida, T., Beppu, M., Nashiki, K., Izumi, T., Ebihara, K. Nutrition and cancer. (2000) [Pubmed]
  28. Partial reconstruction of flavonoid and isoflavonoid biosynthesis in yeast using soybean type I and type II chalcone isomerases. Ralston, L., Subramanian, S., Matsuno, M., Yu, O. Plant Physiol. (2005) [Pubmed]
  29. Urinary lignan and isoflavonoid excretion in premenopausal women consuming flaxseed powder. Lampe, J.W., Martini, M.C., Kurzer, M.S., Adlercreutz, H., Slavin, J.L. Am. J. Clin. Nutr. (1994) [Pubmed]
  30. Cloning and functional expression of a cytochrome P450 cDNA encoding 2-hydroxyisoflavanone synthase involved in biosynthesis of the isoflavonoid skeleton in licorice. Akashi, T., Aoki, T., Ayabe, S. Plant Physiol. (1999) [Pubmed]
  31. Urinary isoflavonoid excretion in humans is dose dependent at low to moderate levels of soy-protein consumption. Karr, S.C., Lampe, J.W., Hutchins, A.M., Slavin, J.L. Am. J. Clin. Nutr. (1997) [Pubmed]
  32. Androgen receptor regulation by physiological concentrations of the isoflavonoid genistein in androgen-dependent LNCaP cells is mediated by estrogen receptor beta. Bektic, J., Berger, A.P., Pfeil, K., Dobler, G., Bartsch, G., Klocker, H. Eur. Urol. (2004) [Pubmed]
  33. Isoflavonoid from Viola hondoensis, regulates the expression of matrix metalloproteinase-1 in human skin fibroblasts. Moon, H.I., Lee, J., Kwak, J.H., Zee, O.P., Chung, J.H. Biol. Pharm. Bull. (2005) [Pubmed]
  34. Inhibition of cholesterol ester transfer protein CGS 25159 and changes in lipoproteins in hamsters. Kothari, H.V., Poirier, K.J., Lee, W.H., Satoh, Y. Atherosclerosis (1997) [Pubmed]
  35. p53-independent induction of p21 (WAF1/CIP1), reduction of cyclin B1 and G2/M arrest by the isoflavone genistein in human prostate carcinoma cells. Choi, Y.H., Lee, W.H., Park, K.Y., Zhang, L. Jpn. J. Cancer Res. (2000) [Pubmed]
  36. Genistein is an effective stimulator of sex hormone-binding globulin production in hepatocarcinoma human liver cancer cells and suppresses proliferation of these cells in culture. Mousavi, Y., Adlercreutz, H. Steroids (1993) [Pubmed]
  37. Elicitor-induced association of isoflavone O-methyltransferase with endomembranes prevents the formation and 7-O-methylation of daidzein during isoflavonoid phytoalexin biosynthesis. Liu, C.J., Dixon, R.A. Plant Cell (2001) [Pubmed]
  38. Estrogen receptor signaling protects against immune suppression by UV radiation exposure. Widyarini, S., Domanski, D., Painter, N., Reeve, V.E. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  39. Profiling isoflavonoids found in legume root extracts using capillary electrophoresis. Baggett, B.R., Cooper, J.D., Hogan, E.T., Carper, J., Paiva, N.L., Smith, J.T. Electrophoresis (2002) [Pubmed]
  40. Effects of high-dose soy isoflavones and equol on reproductive tissues in female cynomolgus monkeys. Wood, C.E., Appt, S.E., Clarkson, T.B., Franke, A.A., Lees, C.J., Doerge, D.R., Cline, J.M. Biol. Reprod. (2006) [Pubmed]
  41. Alfalfa (Medicago sativa L.) resistance to the root-lesion nematode, Pratylenchus penetrans: defense-response gene mRNA and isoflavonoid phytoalexin levels in roots. Baldridge, G.D., O'Neill, N.R., Samac, D.A. Plant Mol. Biol. (1998) [Pubmed]
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