Punicalagin

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Punicalagin
Punicalagin1.png
Names
Other names
2,3-(S)-hexahydroxydiphenoyl-4,6-(S,S)-gallagyl-D-glucose
α-punicalagin
β-punicalagin
Identifiers
3D model (JSmol)
ChEMBL
KEGG
PubChem CID
  • C1C(C(OC(=O)C2=CC(=C(C(=C2C3=C(C(=C4C5=C3C(=O)OC6=C(C(=C(C7=C(C(=C(C=C7C(=O)O1)O)O)O)C(=C56)C(=O)O4)O)O)O)O)O)O)O)C8C(OC(=O)C9=CC(=C(C(=C9C1=C(C(=C(C=C1C(=O)O8)O)O)O)O)O)O)C=O)O
Properties
C48H28O30
Molar mass 1084.71 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Punicalagin (Pyuni-cala-jen) is an ellagitannin, a type of phenolic compound. It is found as alpha and beta isomers in pomegranates (Punica granatum), Terminalia catappa , Terminalia myriocarpa , [1] and in Combretum molle , the velvet bushwillow, a plant species found in South Africa. [2] These three genera are all Myrtales and the last two are both Combretaceae.

Contents

Research

Punicalagins are water-soluble and hydrolyze into smaller phenolic compounds, such as ellagic acid.
There were no toxic effects in rats on a 6% diet of punicalagins for 37 days. [3] In laboratory research, punicalagins had carbonic anhydrase inhibitor activity. [4]

See also

Related Research Articles

<span class="mw-page-title-main">Ellagic acid</span> Natural phenol antioxidant

Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.

<span class="mw-page-title-main">Carbonic anhydrase inhibitor</span> Class of pharmaceuticals

Carbonic anhydrase inhibitors are a class of pharmaceuticals that suppress the activity of carbonic anhydrase. Their clinical use has been established as anti-glaucoma agents, diuretics, antiepileptics, in the management of mountain sickness, gastric and duodenal ulcers, idiopathic intracranial hypertension, neurological disorders, or osteoporosis.

1-<i>alpha</i>-<i>O</i>-Galloylpunicalagin Chemical compound

1-α-O-Galloylpunicalagin is an ester of gallic acid and punicalagin, a type of ellagitannin. It is found in the pomegranate and in Combretum glutinosum.

A hydrolysable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids.

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 groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.

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

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 (pomegranate).

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

Gallagic acid is a polyphenolic chemical compound that can be found in the ellagitannins, a type of tannin, found in Punica granatum (pomegranate). It is a building block of the corresponding tannin punicalagin, punicalin, punicacortein C and 2-O-galloyl-punicalin.

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

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 gluconic acid core.

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

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 being Myrtales, the two last being Combretaceae.

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

Punicacortein C is an ellagitannin, a phenolic compound. It is found in the bark of Punica granatum (pomegranate). The molecule contains a gallagic acid component.

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

Punicacortein D is an ellagitannin, a type of phenolic compound. It is found in the bark and heartwood of Punica granatum (pomegranate). The molecule contains a gallagic acid component.

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

Granatin A is an ellagitannin found in the pericarp of Punica granatum (pomegranate). It is a weak carbonic anhydrase inhibitor.

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

Granatin B is an ellagitannin found in the fruit of Punica granatum (pomegranate). It is a molecule having an enantiomeric dehydrohexahydroxydiphenoyl group.

<span class="mw-page-title-main">Pomegranate ellagitannin</span> Ellagitannins found in the pomegranate fruit

The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the sarcotestas, rind (peel), bark or heartwood of pomegranates.

<i>Combretum molle</i> Species of tree

Combretum molle, the velvet bushwillow, is a medium to large tree species in the genus Combretum found in western, eastern and southern Africa.

<i>Terminalia myriocarpa</i> Species of tree

Terminalia myriocarpa, the East Indian almond, is a tree species in the genus Terminalia found in Southeast Asia.

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

Casuarinin is an ellagitannin. It is found in the pericarp of pomegranates. It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana.

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

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

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

Methyl gallate is a phenolic compound. It is the methyl ester of gallic acid.

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

Urolithin A is a metabolite compound resulting from the transformation of ellagitannins by the gut bacteria. It belongs to the class of organic compounds known as benzo-coumarins or dibenzo-α-pyrones. Its precursors – ellagic acids and ellagitannins – are ubiquitous in nature, including edible plants, such as pomegranates, strawberries, raspberries, walnuts, and others.

References

  1. Marzouk, M. S. A.; El-Toumy, S. A. A.; Moharram, F. A.; Shalaby, N. M.; Ahmed, A. A. (2002). "Pharmacologically Active Ellagitannins from Terminalia myriocarpa". Planta Medica. 68 (6): 523–527. doi:10.1055/s-2002-32549. PMID   12094296.
  2. Asres, K.; Bucar, F.; Knauder, E.; Yardley, V.; Kendrick, H.; Croft, S. L. (2001). "In vitro antiprotozoal activity of extract and compounds from the stem bark of Combretum molle". Phytotherapy Research. 15 (7): 613–617. doi:10.1002/ptr.897. PMID   11746844. S2CID   24511496.
  3. Cerdá, B; Cerón, J. J; Tomás-Barberán, F. A; Espín, J. C (2003). "Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic". Journal of Agricultural and Food Chemistry. 51 (11): 3493–501. doi:10.1021/jf020842c. PMID   12744688.
  4. Satomi, H.; Umemura, K.; Ueno, A.; Hatano, T.; Okuda, T.; Noro, T. (1993). "Carbonic anhydrase inhibitors from the pericarps of Punica granatum L". Biological & Pharmaceutical Bulletin. 16 (8): 787–790. doi: 10.1248/bpb.16.787 . PMID   8220326.