Punicafolin

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Punicafolin
Punicafolin.png
Names
Other names
1,2,4-tri-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-β-D-glucose
Identifiers
3D model (JSmol)
ChEMBL
PubChem CID
Properties
C41H30O26
Molar mass 938.63 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Punicafolin is an ellagitannin from the leaves of Punica granatum (pomegranate) [1] and in Phyllanthus emblica . [2]

<i>Phyllanthus emblica</i> species of plant

Phyllanthus emblica, also known as emblic, emblic myrobalan, myrobalan, Indian gooseberry, Malacca tree, or amla from Sanskrit amalaki is a deciduous tree of the family Phyllanthaceae. It has edible fruit, referred to by the same name.

Punicafolin is an isomer of tellimagrandin II and nupharin A, but the hexahydroxydiphenoyl group is not attached to the same hydroxyl groups in the glucose molecule.

Tellimagrandin II chemical compound

Tellimagrandin II is the first of the ellagitannins formed from 1,2,3,4,6-pentagalloyl-glucose. It can be found in Geum japonicum and Syzygium aromaticum (clove).

Nupharin A chemical compound

Nupharin A is an ellagitannin found in Nuphar japonica. It is a molecule with three gallic acid units and one hexahydroxydiphenic acid unit attached to a glucose residue. It is an isomer of punicafolin and tellimagrandin II.

Punicafolin has been shown to have tumor suppressive effects in dogs. [3]

Related Research Articles

Punicalagin chemical compound

Punicalagin is an ellagitannin, a type of phenolic compound. It is found in forms alpha and beta in pomegranates, in Terminalia catappa and Terminalia myriocarpa, and in Combretum molle, the velvet bushwillow, a plant species found in South Africa. These three genera are all Myrtales and the last two are both Combretaceae.

Corilagin 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).

Gallagic acid 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.

1,2,3,4,6-Pentagalloyl glucose chemical compound

1,2,3,4,6-Pentagalloylglucose is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.

Punigluconin 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.

Punicacortein A chemical compound

Punicacortein A is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate) and in Osbeckia chinensis.

Punicalin 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.

Punicacortein C 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.

Punicacortein D 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.

Punicacortein B chemical compound

Punicacortein B is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate).

Granatin A chemical compound

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

Granatin B chemical compound

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

Pomegranate ellagitannin

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

Casuarinin 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.

Pedunculagin chemical compound

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

Sanguisorbic acid chemical compound

Sanguisorbic acid is a constituent of some ellagitannins. It is constituted by a hexahydroxydiphenic acid unit linked by an O-C bond to a gallic acid. The differences with its isomers, valoneic acid and nonahydroxytriphenic acid, are that the hydroxyl that links the hexahydroxydiphenoyl (HHDP) group to the galloyl group belongs to the galloyl group in valoneic acid, while in nonahydroxytriphenic acid, the hexahydroxydiphenic acid unit is linked by a C-C bond to gallic acid.

References

  1. ↑ Tanaka, T.; Nonaka, G. I.; Nishioka, I. (1985). "Punicafolin, an ellagitannin from the leaves of Punica granatum". Phytochemistry. 24 (9): 2075–2078. doi:10.1016/S0031-9422(00)83125-8.
  2. ↑ Zhang, Y. J.; Abe, T.; Tanaka, T.; Yang, C. R.; Kouno, I. (2001). "Phyllanemblinins A-F, new ellagitannins from Phyllanthus emblica". Journal of Natural Products. 64 (12): 1527–1532. doi:10.1021/np010370g. PMID   11754604.
  3. ↑ Tanimura S et al (2005) Suppression of tumor cell invasiveness by hydrolyzable tannins (plant polyphenols) via the inhibition of matrix metalloproteinase-2/-9 activity. Biochem Biophys Res Commun330(4):1306-1313


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