Afzelechin

Afzelechin
	; 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
	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) ; 24808-04-6 (Epiafzelechin) ; 490-61-9 (Racemate) ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:31028 ;
ChEMBL	ChEMBL159303 ;
ChemSpider	391781 ;
KEGG	C12128 ;
PubChem CID	443639;
UNII	W782YDV47U (Afzelechin) ;
CompTox Dashboard (EPA)	DTXSID60300139 ;
	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 Key: RSYUFYQTACJFML-UKRRQHHQSA-N ; 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). verify (what is ?) Infobox references

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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 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^{[permanent dead link‍]}
^ 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.

[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^{[permanent dead link‍]}

[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.

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[5]

v t e Flavan-3-ols and their glycosides
Flavan-3-ols	Afzelechin Catechin (Epicatechin) Epicatechin gallate Epigallocatechin Fisetinidol Gallocatechin Guibourtinidol Mesquitol Oritin 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-O-α-L-arabinoside) Symplocoside (3'-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
Acetylated	Phylloflavan
Gallate esters	Epigallocatechin gallate Gallocatechin gallate
Misc.	Thearubigins