Afzelechin

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Afzelechin
Chemical structure of Epiafzelechin.
Identifiers
PubChem 443639
ChemSpider 391781 YesY
KEGG C12128 YesY
ChEBI CHEBI:31028 YesY
ChEMBL CHEMBL159303 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C15H14O5
Molar mass 274.26 g/mol
Except where noted otherwise, 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[edit]

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

Glycosides[edit]

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[edit]

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[edit]

  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.