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Afzelechin

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Afzelechin

Chemical structure of Afzelechin (2R,3S)

Chemical structure of Afzelechin (2R,3S) in ball-and-stick format

Chemical structure of Epiafzelechin (2R,3R)

Chemical structure of Epiafzelechin (2R,3R) in ball-and-stick format
Names
IUPAC name Afzelechin - (2R,3S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Epiafzelechin - (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Other names 3,5,7,4'-Tetrahydroxyflavan
3,4',5,7-Flavantetrol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1Key: RSYUFYQTACJFML-UKRRQHHQSA-N
  • InChI=1/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1Key: RSYUFYQTACJFML-UKRRQHHQBG
SMILES
  • C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O
  • Oc1ccc(cc1)3Oc2cc(O)cc(O)c2C3O
Properties
Chemical formula C15H14O5
Molar mass 274.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Afzelechin is a flavan-3-ol, a type of flavonoid. It can be found in Bergenia ligulata (a.k.a. Paashaanbhed in Ayurveda traditional Indian medicine). It exists as at least 2 major epimers (afzelechin and epi-afzelechin).

Metabolism

(2R,3S)-catechin:NADP+ 4-oxidoreductase transforms cis-3,4-leucopelargonidin into afzelechin.

Glycosides

Arthromerin A (afzelechin-3-O-β-D-xylopyranoside) and arthromerin B (afzelechin-3-O-β-D-glucopyranoside) are afzelechin glycosides isolated from the roots of the fern Arthromeris mairei. (+)-afzelechin-O-β-4'-D-glucopyranoside can be isolated from the rhizomes of the fern Selliguea feei.

Proanthocyanidins

dimers

Afzelechin-(4alpha→8)-afzelechin (molecular formula : C30H26O10, molar mass : 546.52 g/mol, exact mass : 546.152597, CAS number : 101339-37-1, Pubchem CID : 12395) is a B type proanthocyanidin.
Ent-epiafzelechin-3-O-p-hydroxybenzoate-(4α→8,2α→O→7)-epiafzelechin) is an A-type proanthocyanidin found in apricots (Prunus armeniaca).

Trimers

Selligueain A (epiafzelechin-(4β-8,2β-0-7)-epiafzelechin-(4β-8)-afzelechin) is an A type proanthocyanidin.

References

  1. High pressure liquid chromatographic determination of bergenin and (+) -afzelechin from different parts of Paashaanbhed (Bergenia ligulata yeo). Umashankar D. Chandra Reddy, Amrik S. Chawla, Mundkinajeddu Deepak, Deepa Singh, Sukhdev S. Handa, 1997
  2. (2R,3S)-catechin:NADP+ 4-oxidoreductase on nashua.case.edu
  3. Two afzelechin glycosides from Arthromeris mairei. Yu Wen-Sheng, Li Hong, Chen Xin-Min and Yang Lei, Phytochemistry, December 1992, Volume 31, Issue 12, pages 4385–4386, doi:10.1016/0031-9422(92)80488-Z, INIST 4682275
  4. Flavonoids and a proanthrocyanidin from rhizomes of Selliguea feei. Baek Nam-In, Kennelly E.J, Kardono L.B.S, Tsauri S, Padmawinata K, Soejarto D.D and Kinghorn A.D, Phytochemistry, 1994, vol. 36, no 2, pages 513-518, INIST 3300075
  5. Prasad, D; Joshi, RK; Pant, G; Rawat, MS; Inoue, K; Shingu, T; He, ZD (1998). "An A-type proanthocyanidin from Prunus armeniaca". Journal of Natural Products. 61 (9): 1123–5. doi:10.1021/np970383n. PMID 9748379.
Flavan-3-ols and their glycosides
Flavan-3-ols
O-methylated flavan-3ols
Glycosides
AcetylatedPhylloflavan
Gallate esters
Misc.
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