Afzelechin

Afzelechin
IUPAC name (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 Epiafzelechin
Identifiers
PubChem	443639
ChemSpider	391781 Y
KEGG	C12128 Y
ChEBI	CHEBI:31028 Y
ChEMBL	CHEMBL159303 Y
Jmol-3D images	Image 1 Image 2
SMILES 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
InChI 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
Properties
Molecular formula	C15H14O5
Molar mass	274.26 g/mol
Exact mass	274.084124
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Afzelechin is a flavan-3ol, a type of flavonoids. 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 Arthromeris mairei^[3].

(+)-afzelechin-O-β-4'-D-glucopyranoside can be isolated from the rhizomes of 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 a A type proanthocyanidin.

References

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; Yang Lei; 1992
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.; Kinghorn A.D., Phytochemistry, 1994, vol. 36, no2, pp. 513-518 (19 ref.)
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.