Afzelechin

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Afzelechin
Afzelechin.svg
Chemical structure of Afzelechin (2R,3S)
Afzelechin 3D BS.png
Chemical structure of Afzelechin (2R,3S) in ball-and-stick format
Epiafzelechin.svg
Chemical structure of Epiafzelechin (2R,3R)
Epiafzelechin 3D BS.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: RSYUFYQTACJFML-UKRRQHHQSA-N Yes check.svgY
  • 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
  • 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
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 two major epimers (afzelechin and epiafzelechin).

Contents

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-(4α→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.[ citation needed ]

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→O→7)-epiafzelechin-(4β→8)-afzelechin) is an A type proanthocyanidin.[ citation needed ]

References

  1. ↑ Chandra Reddy UD, Chawla AS, Deepak M, Singh D, Handa SS (January 1999). "High pressure liquid chromatographic determination of bergenin and (+)-afzelechin from different parts of Paashaanbhed (Bergenia ligulata yeo)". Phytochemical analysis. 10 (1): 44–47. doi:10.1002/(SICI)1099-1565(199901/02)10:1<44::AID-PCA424>3.0.CO;2-4.
  2. ↑ (2R,3S)-catechin:NADP+ 4-oxidoreductase on nashua.case.edu [ permanent dead link ]
  3. ↑ Yu W, Li H, Chen X, Yang L (December 1992). "Two afzelechin glycosides from Arthromeris mairei". Phytochemistry. 31 (12): 4385–4386. doi:10.1016/0031-9422(92)80488-Z. INIST   4682275
  4. ↑ Baek N, Kennelly EJ, Kardono LB, Tsauri S, Padmawinata K, Soejarto DD, Kinghorn AD (May 1994). "Flavonoids and a proanthrocyanidin from rhizomes of Selliguea feei". Phytochemistry. 36 (2): 513–518. doi:10.1016/S0031-9422(00)97105-X. INIST   3300075
  5. ↑ Prasad D, Joshi RK, Pant G, Rawat MS, Inoue K, Shingu T, He ZD (August 1998). "An A-type proanthocyanidin from Prunus armeniaca". Journal of Natural Products. 61 (9): 1123–1125. doi:10.1021/np970383n. PMID   9748379.
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