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 2 major epimers (afzelechin and epi-afzelechin).

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-(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.

Related Research Articles

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<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

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<span class="mw-page-title-main">Taxifolin</span> Chemical compound

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Procyanidin C2 is a B type proanthocyanidin trimer, a type of condensed tannin.

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Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape, in Lysimachia congestiflora and in Vaccinium uliginosum. It is one of the phenolic compounds present in wine.

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<span class="mw-page-title-main">Procyanidin C1</span> Chemical compound

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<span class="mw-page-title-main">Bergenin</span> Chemical compound

Bergenin, alias cuscutin, is trihydroxybenzoic acid glycoside. It is the C-glycoside of 4-O-methyl gallic acid. It possesses an O-demethylated derivative called norbergenin. These are chemical compounds and drugs of Ayurveda, commonly known as Paashaanbhed. It shows a potent immunomodulatory effect.

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In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<span class="mw-page-title-main">Cucurbitane</span> Chemical compound

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30
H
54
. It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane, from which it differs by the formal shift of a methyl group from the 10 to the 9β position in the standard steroid numbering scheme.

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Kaempferol 3-<i>O</i>-rutinoside Chemical compound

Kaempferol-3-O-rutinoside is a bitter-tasting flavonol glycoside. It can be isolated from the rhizomes of the fern Selliguea feei.

Catechin-7-<i>O</i>-glucoside Chemical compound

Catechin-7-O-glucoside is a flavan-3-ol glycoside formed from catechin.

Arthromeris mairei is a fern species in the genus Arthromeris.

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 [ 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.