Afzelechin
Chemical compound
From Wikipedia, the free encyclopedia
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).
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
3,5,7,4â²-Tetrahydroxyflavan 3,4â²,5,7-Flavantetrol | |
| Identifiers | |
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3D model (JSmol) |
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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-4â²-D-glucopyranoside can be isolated from the rhizomes of the fern Selliguea feei.[4]
Proanthocyanidins
Dimers
Afzelechin-(4뱉8)-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-(4αâ8,2αâOâ7)-epiafzelechin is an A-type proanthocyanidin found in apricots (Prunus armeniaca).[5]
Trimers
Selligueain A (epiafzelechin-(4βâ8,2βâOâ7)-epiafzelechin-(4βâ8)-afzelechin) is an A type proanthocyanidin.[citation needed]