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Chemical Compound Review

Isoflavanone     3-phenylchroman-4-one

Synonyms: iso-flavanone, SureCN72983, AG-J-60410, CHEMBL2011171, CHEBI:27945, ...
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Disease relevance of Isoflavanone


High impact information on Isoflavanone

  • Functional analysis of members of the isoflavone and isoflavanone O-methyltransferase enzyme families from the model legume Medicago truncatula [3].
  • Analysis of circular dichroism (CD) spectra of the reduction product sophorol obtained using the recombinant enzyme indicated that the isoflavanone possessed the 3R stereochemistry, in contrast to previous reports indicating a 3S-isoflavanone as the product of the pea IFR [4].
  • These findings show that 4'-hydroxylation results in either no change or very little change in IC50 for flavanone, isoflavone and isoflavanone as well as other ring A hydroxylated flavones [5].
  • Bioassay-guided fractionation of the extract using a GAL-4-PPAR-gamma chimera assay method resulted in the isolation of two isoflavenes, one of which is a new compound named dehydroglyasperin D, an isoflavan, two 3-arylcoumarins, and an isoflavanone as the PPAR-gamma ligand-binding active ingredients of licorice [6].
  • Three minor flavonoids, licofuranocoumarin, isotrifoliol and glisoflavanone, were isolated from licorice (underground part of Glycyrrhiza uralensis), and their structures with 3-arylcoumarin, coumestan and isoflavanone skeletons were respectively elucidated on the basis of spectroscopic data [7].

Associations of Isoflavanone with other chemical compounds

  • In addition to the two known compounds neotautenol [2] and erythrinassinate B [4], two new compounds, an isoflavanone named sigmoidin J [1] and a coumestan derivative named sigmoidin K [3], have been isolated and characterized from the root bark of the Cameroonian medicinal plant Erythrina sigmoidea [8].
  • A novel prenylated isoflavanone, sigmoidin I, has been isolated from the roots of Erythrina sigmoidea, in addition to the known isoflavones, corylin and neobavaisoflavone and the known pterocarpan, phaseollidin [9].
  • Dou-chi, a traditional soybean food fermented with Aspergillus sp., is usually used as a seasoning in Chinese food, and has also been used as a folk medicine in China and Taiwan. As 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavengers, four phenol compounds, one isoflavanone, eight isoflavones and one 4-pyrone have been isolated from dou-chi [10].


  1. WS-7528, a new isoflavanone with estrogen activity isolated from Streptomyces sp. No. 7528. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities. Nakayama, O., Yagi, M., Tanaka, M., Kiyoto, S., Uchida, I., Hashimoto, M., Okuhara, M., Kohsaka, M. J. Antibiot. (1990) [Pubmed]
  2. Synergistic effects of mupirocin and an isoflavanone isolated from Erythrina variegata on growth and recovery of methicillin-resistant Staphylococcus aureus. Sato, M., Tanaka, H., Yamaguchi, R., Kato, K., Etoh, H. Int. J. Antimicrob. Agents (2004) [Pubmed]
  3. Functional analysis of members of the isoflavone and isoflavanone O-methyltransferase enzyme families from the model legume Medicago truncatula. Deavours, B.E., Liu, C.J., Naoumkina, M.A., Tang, Y., Farag, M.A., Sumner, L.W., Noel, J.P., Dixon, R.A. Plant Mol. Biol. (2006) [Pubmed]
  4. Molecular cloning of isoflavone reductase from pea (Pisum sativum L.): evidence for a 3R-isoflavanone intermediate in (+)-pisatin biosynthesis. Paiva, N.L., Sun, Y., Dixon, R.A., VanEtten, H.D., Hrazdina, G. Arch. Biochem. Biophys. (1994) [Pubmed]
  5. Aromatase inhibition by flavonoids. Ibrahim, A.R., Abul-Hajj, Y.J. J. Steroid Biochem. Mol. Biol. (1990) [Pubmed]
  6. Phenolics with PPAR-gamma ligand-binding activity obtained from licorice (Glycyrrhiza uralensis roots) and ameliorative effects of glycyrin on genetically diabetic KK-A(y) mice. Kuroda, M., Mimaki, Y., Sashida, Y., Mae, T., Kishida, H., Nishiyama, T., Tsukagawa, M., Konishi, E., Takahashi, K., Kawada, T., Nakagawa, K., Kitahara, M. Bioorg. Med. Chem. Lett. (2003) [Pubmed]
  7. Minor flavonoids from licorice. Hatano, T., Aga, Y., Shintani, Y., Ito, H., Okuda, T., Yoshida, T. Phytochemistry (2000) [Pubmed]
  8. Sigmoidins J and K, two new prenylated isoflavonoids from Erythrina sigmoidea. Nkengfack, A.E., Vouffo, T.W., Vardamides, J.C., Fomum, Z.T., Bergendorff, O., Sterner, O. J. Nat. Prod. (1994) [Pubmed]
  9. Prenylated isoflavanone from the roots of Erythrina sigmoidea. Nkengfack, A.E., Vouffo, T.W., Fomum, Z.T., Meyer, M., Bergendorff, O., Sterner, O. Phytochemistry (1994) [Pubmed]
  10. DPPH radical-scavenging compounds from dou-chi, a soybean fermented food. Chen, Y.C., Sugiyama, Y., Abe, N., Kuruto-Niwa, R., Nozawa, R., Hirota, A. Biosci. Biotechnol. Biochem. (2005) [Pubmed]
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