Afzelechin is a

flavan-3-ol Flavan-3-ols (sometimes referred to as flavanols) are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2''H''-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compo ...

, a type of flavonoid. It can be found in ''

Bergenia ligulata ''Bergenia ligulata'' (''Paashaanbhed'', ''Prashanbheda'', and other spellings in Ayurveda traditional Indian medicine) is a plant belonging to the family Saxifragaceae and the genus '' Bergenia''. It is plant is sometimes treated as a form of ' ...

'' ( ''paashaanbhed'' in

Ayurveda Ayurveda (; ) is an alternative medicine system with historical roots in the Indian subcontinent. It is heavily practised throughout India and Nepal, where as much as 80% of the population report using ayurveda. The theory and practice of ayur ...

traditional Indian medicine). It exists as at least two major

epimer In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have opposite configuration at only one stereogenic center out of at least two. All other stereogenic centers in the molecules are the same in each. Epimerization is t ...

s (afzelechin and epiafzelechin).

Metabolism

(2''R'',3''S'')-Catechin:NADP⁺ 4-oxidoreductase transforms ''cis''-3,4-

leucopelargonidin Leucopelargonidin is a colorless chemical compound related to leucoanthocyanins. It can be found in ''Albizia lebbeck'' (East Indian walnut), in the fruit of ''Anacardium occidentale'' (Cashew), in the fruit of ''Areca catechu'' (Areca nut), in th ...

into afzelechin.

Glycosides

Arthromerin A (afzelechin-3-''O''-β-D-xylopyranoside) and arthromerin B (afzelechin-3-''O''-β-D-glucopyranoside) are afzelechin

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...

s isolated from the roots of the fern ''

Arthromeris mairei ''Arthromeris mairei'' is a fern species in the genus '' Arthromeris''. Two afzelechin Afzelechin is a flavan-3-ol, a type of flavonoid. It can be found in '' Bergenia ligulata'' ( ''paashaanbhed'' in Ayurveda traditional Indian medicine). It e ...

''. (+)-Afzelechin-''O''-β-4′-D-glucopyranoside can be isolated from the rhizomes of the fern ''

Selliguea feei ''Selliguea feei'' is a fern belonging to the genus '' Selliguea'' in the family Polypodiaceae. This fern can be collected in Indonesia. The species name ''feei'' commemorates the botanist Antoine Laurent Apollinaire Fée Antoine Laurent Apolli ...

''.

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 B type proanthocyanidins are a specific type of proanthocyanidin, which are a class of flavanoids. They are oligomers of flavan-3-ols. Dimeric B type proanthocyanidins These molecules have the molecular formula C30H26O12 (molar mass : 578.52 g/m ...

. ''ent''-Epiafzelechin-3-''O''-''p''-hydroxybenzoate-(4α→8,2α→''O''→7)-epiafzelechin is an

A-type proanthocyanidin A type proanthocyanidins are a specific type of proanthocyanidins, which are a class of flavonoid. Proanthocyanidins fall under a wide range of names in the nutritional and scientific vernacular, including oligomeric proanthocyanidins, flavonoids, ...

found in

apricot An apricot (, ) is a fruit, or the tree that bears the fruit, of several species in the genus ''Prunus''. Usually an apricot is from the species '' P. armeniaca'', but the fruits of the other species in ''Prunus'' sect. ''Armeniaca'' are also ...

s (''Prunus armeniaca'').

Trimers

Selligueain A Selligueain A is an A type proanthocyanidin trimer of the propelargonidin type. It can be extracted from the rhizome of the fern ''Selliguea feei'' collected in Indonesia. It has sweetener A sweetener is a substance added to food or drink to ...

(epiafzelechin-(4β→8,2β→''O''→7)-epiafzelechin-(4β→8)-afzelechin) is an

A type proanthocyanidin A type proanthocyanidins are a specific type of proanthocyanidins, which are a class of flavonoid. Proanthocyanidins fall under a wide range of names in the nutritional and scientific vernacular, including oligomeric proanthocyanidins, flavonoids, ...

References

{{Flavanol Flavanols Resorcinols