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).
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
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]
Proanthocyanidinsedit
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]
^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, INIST4682275
^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, INIST3300075
afzelechin, flavan, type, flavonoid, found, bergenia, ligulata, paashaanbhed, ayurveda, traditional, indian, medicine, exists, least, major, epimers, afzelechin, afzelechin, chemical, structure, chemical, structure, ball, stick, format, chemical, structure, ep. 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 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 Tetrahydroxyflavan3 4 5 7 Flavantetrol Identifiers CAS Number 2545 00 8 Afzelechin Y24808 04 6 Epiafzelechin N490 61 9 Racemate N 3D model JSmol Interactive imageInteractive image ChEBI CHEBI 31028 Y ChEMBL ChEMBL159303 Y ChemSpider 391781 Y KEGG C12128 Y PubChem CID 443639 UNII W782YDV47U Afzelechin Y 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 YKey RSYUFYQTACJFML UKRRQHHQSA N YInChI 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 s1Key RSYUFYQTACJFML UKRRQHHQBG SMILES C1C C OC2 CC CC C21 O O C3 CC C C C3 O OOc1ccc 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 Y N Infobox references Contents 1 Metabolism 2 Glycosides 3 Proanthocyanidins 4 ReferencesMetabolism edit 2R 3S catechin NADP 4 oxidoreductase transforms cis 3 4 leucopelargonidin into afzelechin 2 Glycosides editArthromerin A afzelechin 3 O b D xylopyranoside and arthromerin B afzelechin 3 O b D glucopyranoside are afzelechin glycosides isolated from the roots of the fern Arthromeris mairei 3 afzelechin O b 4 D glucopyranoside can be isolated from the rhizomes of the fern Selliguea feei 4 Proanthocyanidins editdimers 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 4a 8 2a O 7 epiafzelechin is an A type proanthocyanidin found in apricots Prunus armeniaca 5 Trimers Selligueain A epiafzelechin 4b 8 2b 0 7 epiafzelechin 4b 8 afzelechin is an A type proanthocyanidin References edit 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 Retrieved from https en wikipedia org w index php title Afzelechin amp oldid 1129126515, wikipedia, wiki, book, books, library,
