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Afzelechin

Chemical compound From Wikipedia, the free encyclopedia

Afzelechin

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).[1] It exists as at least two major epimers (afzelechin and epiafzelechin).

Quick Facts Names, Identifiers ...
Afzelechin
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Chemical structure of Afzelechin (2R,3S)
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Chemical structure of Afzelechin (2R,3S) in ball-and-stick format
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Chemical structure of Epiafzelechin (2R,3R)
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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • 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/s1 Y
    Key: RSYUFYQTACJFML-UKRRQHHQSA-N Y
  • 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/s1
    Key: RSYUFYQTACJFML-UKRRQHHQBG
  • C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O
  • Oc1ccc(cc1)[C@H]3Oc2cc(O)cc(O)c2C[C@H]3O
Properties
C15H14O5
Molar mass 274.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Metabolism

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

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.[3] (+)-Afzelechin-O-β-4′-D-glucopyranoside can be isolated from the rhizomes of the fern Selliguea feei.[4]

Proanthocyanidins

Dimers

Afzelechin-(4α→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.[citation needed]

ent-Epiafzelechin-3-O-p-hydroxybenzoate-(4α→8,2α→O→7)-epiafzelechin is an A-type proanthocyanidin found in apricots (Prunus armeniaca).[5]

Trimers

Selligueain A (epiafzelechin-(4β→8,2β→O→7)-epiafzelechin-(4β→8)-afzelechin) is an A type proanthocyanidin.[citation needed]

References

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