Afzelechin Explained

Afzelechin is a flavan-3-ol, a type of flavonoid. It can be found in Bergenia ligulata (Paashaanbhed in Ayurveda traditional Indian medicine).^[1] It exists as at least 2 major epimers (afzelechin and epi-afzelechin).

Metabolism

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

dimersAfzelechin-(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]

TrimersSelligueain A (epiafzelechin-(4β-8,2β-0-7)-epiafzelechin-(4β-8)-afzelechin) is an A type proanthocyanidin.

Notes and References

1. https://archive.today/20100828130830/http://www3.interscience.wiley.com/journal/40002039/abstract?CRETRY=1&SRETRY=0 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. http://nashua.case.edu/PathwaysKegg/Web/?viewID=eba2bc98-9e49-42ee-a6c9-de25d42109bc&pwgid=92e3f03e-9433-4b3e-a82c-3d82d40c45a4 (2R,3S)-catechin:NADP+ 4-oxidoreductase on nashua.case.edu
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,,
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,
5. 9748379 . 1998 . Prasad . D . Joshi . Pant . Rawat . Inoue . Shingu . He . An A-type proanthocyanidin from Prunus armeniaca . 61 . 9 . 1123–5 . 10.1021/np970383n . Journal of Natural Products . RK . G . MS . K . T . ZD.