Afzelechin

Afzelechin
Names
Chemical structure of Afzelechin (2R,3S)
Chemical structure of Epiafzelechin (2R,3R)
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
CAS Number	2545-00-8 Afzelechin^N 24808-04-6 Epiafzelechin^N 490-61-9 (Racemate)^N
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:31028^Y
ChEMBL	ChEMBL159303^Y
ChemSpider	391781^Y
KEGG	C12128^Y
PubChem	443639
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
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
Properties
Chemical formula	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).
N verify (what is ^YN ?)
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] It exists as at least 2 major epimers (afzelechin and epi-afzelechin).

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
↑ 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.

Flavan-3-ols and their glycosides

Flavan-3-ols	Afzelechin Catechin (Epicatechin) Epicatechin gallate Epigallocatechin Epigallocatechin gallate Fisetinidol Gallocatechin Gallocatechin gallate Guibourtinidol Mesquitol Robinetinidol

O-methylated flavan-3ols	Meciadanol (3-O-methylcatechin) Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)

Glycosides	Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside) Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside) Catechin-3-O-glucoside Catechin-3'-O-glucoside Catechin-4'-O-glucoside Catechin-5-O-glucoside Catechin-7-O-glucoside (+)-Catechin 7-O-β-D-xylopyranoside Epicatechin-3′-O-glucoside Glochiflavanoside A, B, C D Polydine ((+)-catechin 7-0-α-L-arabinoside) Symplocoside (3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)

Acetylated	Phylloflavan

Misc.	Thearubigins

This article is issued from Wikipedia - version of the 11/15/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.