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 2 major epimers (afzelechin and epi-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 | |
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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 | |
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3D model (JSmol) |
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ChEBI | |
ChEMBL | |
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KEGG | |
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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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-(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).[5]
- Trimers
Selligueain A (epiafzelechin-(4β-8,2β-0-7)-epiafzelechin-(4β-8)-afzelechin) is an A type proanthocyanidin.
References
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