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The pomegranate ellagitannins, which include punicalagin isomers, are
ellagitannin The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl ...
s found in the sarcotestas, rind (peel), bark or heartwood of
pomegranate The pomegranate (''Punica granatum'') is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punicoideae, that grows between tall. The pomegranate was originally described throughout the Mediterranean Basin, Mediterranean re ...
s (''Punica granatum'').


Chemistry

As the chemistry of punicalagins became known it was found to be not unique to pomegranate. Punicalagins are present in numerous species of the genus '' Terminalia'', species '' chebula'' Retz. (“Fructus Chebulae”), ''
myriocarpa ''Myriocarpa'' is a genus woody plant which ranges in size from shrubs to small trees and is Endemism, endemic to Central America, Central and South America. Within the Urticaceae, ''Myriocarpa'' is characterized by long pendulous string-like fe ...
'', '' catappa'' and citrina (tropical flowering trees historically used in African traditional medicine for antibiotic and antifungal purposes). They have also been isolated from '' Cistus salvifolius'' (a Mediterranean shrub) and ''
Combretum molle ''Combretum molle'', the velvet bushwillow, is a medium to large tree species in the genus '' Combretum'' found in western, eastern and southern Africa. The larvae of ''Parosmodes morantii'' and ''Acalyptris molleivora'' feed on ''C. molle''. I ...
'' (an African shrub). Pomegranate fruits natural phenols can be extracted with
ethyl acetate Ethyl acetate ( systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula , simplified to . This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues ...
and fractionation can afford the ellagitannin punicalagins.


Dietary supplementation

A few
dietary supplements A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...
and nutritional ingredients are available that contain extracts of whole pomegranate and/or are standardized to punicalagins, the marker compound of pomegranate. Extracts of pomegranate are also 'Generally Recognized As Safe' (GRAS) by the United States.


List of compounds

*
Pedunculagin Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group. Natural occurrence Pedunculagin is found in plants in orders in the clade Rosidae. It can be found the pericarp of pomegranates (''Punica granatum'' ...
, a compound found in the
pericarp Fruit anatomy is the plant anatomy of the internal structure of fruit. Fruits are the mature ovary or ovaries of one or more flowers. They are found in three main anatomical categories: aggregate fruits, multiple fruits, and simple fruits. Ag ...
of the pomegranate (''Punica granatum''). * Punicacortein A, a compound found in the bark of ''P. granatum'' and in ''
Osbeckia chinensis ''Osbeckia chinensis'' is a plant species in the genus '' Osbeckia''. ''Osbeckia chinensis'' contains the ellagitanin punicacortein A.Tannin antioxidants from Osbeckia chinensis. Jeng-De Su, Toshihiko Osawa, Shunro Kawakishi and Mitsuo Namiki, ...
'' * Punicacortein B, a compound found in the bark of ''P. granatum'' * Punicacortein C, a compound found in the bark of ''P. granatum'' * Punicacortein D, a compound found in the bark and heartwood of ''P. granatum'' *
Punicafolin Punicafolin is an ellagitannin from the leaves of '' Punica granatum'' (pomegranate) and in ''Phyllanthus emblica ''Phyllanthus emblica'', also known as emblic, emblic myrobalan, myrobalan, Indian gooseberry, Malacca tree, or amla, from the San ...
, a compound found in the leaves of ''Punica granatum'' *
Punigluconin Punigluconin is an ellagitannin, a polyphenol compound. It is found in the bark of ''Punica granatum'' (pomegranate) and in '' Emblica officinalis''. It is a molecule having a hexahydroxydiphenic acid group and two gallic acids attached to a glucon ...
, a compound found in the bark of ''P. granatum'' and in '' Emblica officinalis'' * Punicalagin, a compound found in the pericarps of ''P. granatum'' * Punicalin, a compound found in pomegranates or in the leaves of ''
Terminalia catappa ''Terminalia catappa'' is a large tropical tree in the leadwood tree family, Combretaceae, native to Asia, Australia, the Pacific, Madagascar and Seychelles. Common names in English include country almond, Indian almond, Malabar almond, sea almon ...
'' * Granatin A, a compound found in the pericarp of ''P. granatum'' * Granatin B, a compound found in the fruit of ''P. granatum'' * Diellagic acid rhamnosyl (1→4) glucopyranoside * 5-O-galloylpunicacortein D * 2-O-galloylpunicalin *
Casuarinin Casuarinin is an ellagitannin. It is found in the pericarp of pomegranates (''Punica granatum''). It is also found in ''Casuarina'' and '' Stachyurus'' species and in '' Alnus sieboldiana''. It is an isomer of casuarictin. It is a highly active ca ...
, a compound found in the pericarp of ''P. granatum'' * Gallagyldilactone, a compound found in the pericarp of ''P. granatum'' * Corilagin, a compound found in the leaves of ''P. granatum'' and other species * Strictinin, a compound found in the leaves of ''P. granatum'' ; other phenolics *
Ellagic acid Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid. Name The name comes from the French term ''acide ellagique'', from the word ''galle'' spelled backwards because it can be o ...
, a constitutive compound of ellagitannins * Gallagic acid, a compound found in many ellagitannins * 1,2,4,6-tetra-O-galloyl-β-D-glucose, a compound found in the leaves of ''P. granatum'' * 1,2,3,4,6-penta-O-galloyl-β-D-glucose, a compound found in the leaves of ''P. granatum'' and the common precursor of gallotannins and the related ellagitannins * Brevifolin, a compound found in the leaves of ''P. granatum'' * Brevifolin carboxylic acid, a compound found in the leaves of ''P. granatum'' * 3,6-(R)-hexahydroxydiphenoyl-(α/β)-C-glucopyranose, a compound found in the leaves of ''P. granatum'' * 1,2,6-tri-O-galloyl-β-C-glucopyranose, a compound found in the leaves of ''P. granatum'' * 1,4,6-tri-O-galloyl-β-C-glucopyranose, a compound found in the leaves of ''P. granatum'' * 3,4,8,9,10-pentahydroxydibenzo ,dyran-6-one, a compound found in the leaves of ''P. granatum''


See also

*
List of antioxidants in food This is a list of antioxidants naturally occurring in food. Vitamin C and vitamin E – which are ubiquitous among raw plant foods – are confirmed as dietary antioxidants, whereas vitamin A becomes an antioxidant following metabolism of p ...


References

{{Pomegranate ellagitannin Plants used in traditional African medicine