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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

FLAVANE     2-phenylchroman

Synonyms: Flavan, CHEMBL444299, SureCN123287, AG-F-65553, CHEBI:38691, ...
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High impact information on Flavan

  • The use of in situ hybridization established that chalcone synthase transcripts accumulate in flavan-containing cells at the apex of the nodule lobe [1].
  • We succeeded in a first total synthesis of flavocommelin (1), a component of the blue supramolecular pigment, commelinin (2), from Commelina communis, by direct 6-C-glycosylation of the flavan 4 using perbenzylglucosyl fluoride 8 in the presence of MS 5 angstroms in CH2Cl2 and a catalytic amount of BF3 x Et2O [2].
  • Epicatechin, a flavan 3-ol present in the peel of unripe avocado fruit, had a Ki of 3.4 microM for inhibition of PL activity in vitro [3].
  • Two flavonoid glycosides and a miscellaneous flavan from the bark of Guibourtia coleosperma [4].
  • A monoprenylated flavan and two monoterpenoid substituted furanocoumarins were isolated from the twigs of Dorstenia elliptica along with 3-(3,3-dimethylallyl)-4,2',4'-trihydroxylchalcone, psoralen, bergapten, O-[3-(2,2-dimethyl-3-oxo-2H-furan-5-yl)butyl]bergaptol, beta-sitosterol and its beta-D-glucopyranoside [5].

Biological context of Flavan

  • The chemical structure-activity relationship shows that the anti-oxidative action advanced with the condensation of two molecules of flavan-3-ols as well as with 3-O-acylation in the flavan skeleton such as that by galloyl, (3'-O-methyl)-galloyl, and p-coumaroyl groups [6].

Associations of Flavan with other chemical compounds

  • Melacacidin, known to be the main constituent of these flavan derivatives in the heartwood, was isolated and its sensitizing capacity in guinea pigs determined [7].


  1. Flavan-containing cells delimit Frankia-infected compartments in Casuarina glauca nodules. Laplaze, L., Gherbi, H., Frutz, T., Pawlowski, K., Franche, C., Macheix, J.J., Auguy, F., Bogusz, D., Duhoux, E. Plant Physiol. (1999) [Pubmed]
  2. Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan. Oyama, K., Kondo, T. J. Org. Chem. (2004) [Pubmed]
  3. Purification of pectate lyase produced by Colletotrichum gloeosporioides and its inhibition by epicatechin: a possible factor involved in the resistance of unripe avocado fruits to anthracnose. Wattad, C., Dinoor, A., Prusky, D. Mol. Plant Microbe Interact. (1994) [Pubmed]
  4. Two flavonoid glycosides and a miscellaneous flavan from the bark of Guibourtia coleosperma. Bekker, M., Bekker, R., Brandt, V.E. Phytochemistry (2006) [Pubmed]
  5. Prenylated flavonoids, monoterpenoid furanocoumarins and other constituents from the twigs of Dorstenia elliptica (Moraceae). Abegaz, B.M., Ngadjui, B.T., Folefoc, G.N., Fotso, S., Ambassa, P., Bezabih, M., Dongo, E., Rise, F., Petersen, D. Phytochemistry (2004) [Pubmed]
  6. Evaluation of the anti-oxidative effect (in vitro) of tea polyphenols. Hashimoto, F., Ono, M., Masuoka, C., Ito, Y., Sakata, Y., Shimizu, K., Nonaka, G., Nishioka, I., Nohara, T. Biosci. Biotechnol. Biochem. (2003) [Pubmed]
  7. Contact allergy to Australian blackwood (Acacia melanoxylon R.Br.): isolation and identification of new hydroxyflavan sensitizers. Hausen, B.M., Bruhn, G., Tilsley, D.A. Contact Derm. (1990) [Pubmed]
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