The pomegranate ellagitannins, which include
punicalagin
Punicalagin is an ellagitannin, a type of phenolic compound. It is found as alpha and beta isomers in pomegranates (''Punica granatum''), ''Terminalia catappa'', ''Terminalia myriocarpa'', and in ''Combretum molle'', the velvet bushwillow, a plant ...
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 group ...
s found in the
sarcotesta
The sarcotesta is a fleshy seedcoat, a type of testa. Examples of seeds with a sarcotesta are pomegranate and some cycad seeds. The sarcotesta of pomegranate seeds consists of epidermal cells derived from the integument
In biology, an integu ...
s, 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
Terminalia may refer to:
* Terminalia (festival), a Roman festival to the god of boundaries Terminus
* ''Terminalia'' (plant), a tree genus
* Terminalia (insect anatomy), the terminal region of the abdomen in insects
* ''Polyscias terminalia'', a ...
'', species ''
chebula'' Retz. (“Fructus Chebulae”), ''
myriocarpa'', ''
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''. ...
'' (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 (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients either extr ...
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. Aggre ...
of the pomegranate (''Punica granatum'').
*
Punicacortein A
Punicacortein A is an ellagitannin, a polyphenol compound. It is found in the bark of ''Punica granatum
The pomegranate (''Punica granatum'') is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punicoideae, that grows betwe ...
, 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
Punicacortein A is an ellagitannin, a polyphenol compound. It is found in the bark of ''Punica granatum
...
''
*
Punicacortein B, a compound found in the bark of ''P. granatum''
*
Punicacortein C
Punicacortein C is an ellagitannin, a phenolic compound. It is found in the bark of ''Punica granatum'' (pomegranate).Tannins and Related Compounds. XLI. : Isolation and Characterization of Novel Ellagitannins, Punicacorteins A, B, C, and D, and Pu ...
, 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''.
Punicafolin is an isomer of tellimagrandin II and nupharin A, but the hexahydroxydiphenoyl
Hexahydroxydiphenic acid is an organ ...
, 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 gluconi ...
, a compound found in the bark of ''P. granatum'' and in ''
Emblica officinalis
''Phyllanthus emblica'', also known as emblic, emblic myrobalan, myrobalan, Indian gooseberry, Malacca tree, or amla, from the Sanskrit आमलकी (āmalakī), is a deciduous tree of the family Phyllanthaceae. Its native range is tropical a ...
''
*
Punicalagin
Punicalagin is an ellagitannin, a type of phenolic compound. It is found as alpha and beta isomers in pomegranates (''Punica granatum''), ''Terminalia catappa'', ''Terminalia myriocarpa'', and in ''Combretum molle'', the velvet bushwillow, a plant ...
, a compound found in the pericarps of ''P. granatum''
*
Punicalin
Punicalin is an ellagitannin. It can be found in ''Punica granatum'' (pomegranate) or in the leaves of ''Terminalia catappa'', a plant used to treat dermatitis and hepatitis. It is also reported in '' Combretum glutinosum'', all three species bein ...
, 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 ...
, a compound found in the pericarp of ''P. granatum''[
* Gallagyldilactone, a compound found in the pericarp of ''P. granatum''][
* ]Corilagin
Corilagin is an ellagitannin. Corilagin was first isolated in 1951 from Dividivi extract and from ''Caesalpinia coriaria'', hence the name of the molecule. It can also be found in '' Alchornea glandulosa'' and in the leaves of ''Punica granatum'' ( ...
, a compound found in the leaves of ''P. granatum'' and other species
* Strictinin
Strictinin is a bioactive chemical of the ellagitannin family of hydrolyzable tannins. This compound shows activity against influenza virus
''Orthomyxoviridae'' (from Greek ὀρθός, ''orthós'' 'straight' + μύξα, ''mýxa'' 'mucus') is a ...
, 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 ob ...
, a constitutive compound of ellagitannins
* Gallagic acid
Gallagic acid is a polyphenolic chemical compound that can be found in the ellagitannins, a type of tannin, found in ''Punica granatum'' (pomegranate).Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins an ...
, a compound found in many ellagitannins
* 1,2,4,6-tetra-O-galloyl-β-D-glucose
Onekama ( ) is a village in Manistee County, Michigan, Manistee County in the U.S. state of Michigan. The population was 411 at the 2010 United States Census, 2010 census. The village is located on the shores of Portage Lake (Michigan), Portage Lak ...
, 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 yran-6-one">,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