Afzelechin
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| Names | |
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| IUPAC name
(2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
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| Other names
3,5,7,4'-Tetrahydroxyflavan
3,4',5,7-Flavantetrol Epiafzelechin |
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| Identifiers | |
| ChEBI | CHEBI:31028  |
| ChEMBL | ChEMBL159303 |
| ChemSpider | 391781 |
| Jmol 3D model | Interactive image Interactive image |
| KEGG | C12128 |
| PubChem | 443639 |
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| Properties | |
| C15H14O5 | |
| Molar mass | 274.26 g/mol |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Afzelechin is a flavan-3-ol, a type of flavonoid. It can be found in Bergenia ligulata (aka Paashaanbhed in Ayurveda traditional Indian medicine).[1]
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
- ↑ 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
- ↑ (2R,3S)-catechin:NADP+ 4-oxidoreductase on nashua.case.edu
- ↑ 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
- ↑ 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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
