Pomegranate ellagitannin

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

Chemistry

Punicalagins are not unique to pomegranate, as they are present in numerous species of the genus Terminalia, species chebula Retz., myriocarpa, catappa, and from Cistus salvifolius and Combretum molle.

Dietary supplementation

A few dietary supplements 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.^{[citation needed]}

List of compounds

Ellagitannins

Pedunculagin, a compound found in the pericarp of the pomegranate (Punica granatum).
Punicacortein A, a compound found in the bark of P. granatum and in Osbeckia chinensis
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, a compound found in the leaves of Punica granatum
Punigluconin, 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
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, 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, 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[b,d]pyran-6-one, a compound found in the leaves of P. granatum

References

↑ Barrajón-Catalán, Enrique; Fernández-Arroyo, Salvador; Roldán, Cristina; Guillén, Emilio; Saura, Domingo; Segura-Carretero, Antonio; Micol, Vicente (2011). "A systematic study of the polyphenolic composition of aqueous extracts deriving from several Cistus genus species: Evolutionary relationship". Phytochemical Analysis. 22 (4): 303–12. Bibcode:2011PChAn..22..303B. doi:10.1002/pca.1281. PMID 21259376.
↑ Saracini, E.; Tattini, M.; Traversi, M. L.; Vincieri, F. F.; Pinelli, P. (2005). "Simultaneous LC-DAD and LC-MS Determination of Ellagitannins, Flavonoid Glycosides, and Acyl-Glycosyl Flavonoids in Cistus salvifolius L. Leaves". Chromatographia. 62 (5–6): 245. doi:10.1365/s10337-005-0623-7. S2CID 93426386.
↑ 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): 613–7. doi:10.1002/ptr.897. PMID 11746844. S2CID 24511496.
1 2 3 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.
1 2 3 El-Toumy, Sayed A.A; Rauwald, Hans W (2002). "Two ellagitannins from Punica granatum heartwood". Phytochemistry. 61 (8): 971–4. Bibcode:2002PChem..61..971E. doi:10.1016/S0031-9422(02)00435-1. PMID 12453528.
1 2 3 Tanaka, Takashi; Nonaka, Gen-Ichiro; Nishioka, Itsuo (1985). "Punicafolin, an ellagitannin from the leaves of Punica granatum". Phytochemistry. 24 (9): 2075. Bibcode:1985PChem..24.2075T. doi:10.1016/S0031-9422(00)83125-8.
1 2 3 4 5 6 Nawwar, Mahmoud A.M.; Hussein, Sahar A.M.; Merfort, Irmgard (1994). "NMR spectral analysis of polyphenols from Punica granatum". Phytochemistry. 36 (3): 793. Bibcode:1994PChem..36..793N. doi:10.1016/S0031-9422(00)89820-9.

[1] Barrajón-Catalán, Enrique; Fernández-Arroyo, Salvador; Roldán, Cristina; Guillén, Emilio; Saura, Domingo; Segura-Carretero, Antonio; Micol, Vicente (2011). "A systematic study of the polyphenolic composition of aqueous extracts deriving from several Cistus genus species: Evolutionary relationship". Phytochemical Analysis. 22 (4): 303–12. Bibcode:2011PChAn..22..303B. doi:10.1002/pca.1281. PMID 21259376.

[2] Saracini, E.; Tattini, M.; Traversi, M. L.; Vincieri, F. F.; Pinelli, P. (2005). "Simultaneous LC-DAD and LC-MS Determination of Ellagitannins, Flavonoid Glycosides, and Acyl-Glycosyl Flavonoids in Cistus salvifolius L. Leaves". Chromatographia. 62 (5–6): 245. doi:10.1365/s10337-005-0623-7. S2CID 93426386.

[Asres2-3] 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): 613–7. doi:10.1002/ptr.897. PMID 11746844. S2CID 24511496.

[Satomi-4] 1 2 3 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.

[Toumy-5] 1 2 3 El-Toumy, Sayed A.A; Rauwald, Hans W (2002). "Two ellagitannins from Punica granatum heartwood". Phytochemistry. 61 (8): 971–4. Bibcode:2002PChem..61..971E. doi:10.1016/S0031-9422(02)00435-1. PMID 12453528.

[Tanaka-6] 1 2 3 Tanaka, Takashi; Nonaka, Gen-Ichiro; Nishioka, Itsuo (1985). "Punicafolin, an ellagitannin from the leaves of Punica granatum". Phytochemistry. 24 (9): 2075. Bibcode:1985PChem..24.2075T. doi:10.1016/S0031-9422(00)83125-8.

[Nawwar-7] 1 2 3 4 5 6 Nawwar, Mahmoud A.M.; Hussein, Sahar A.M.; Merfort, Irmgard (1994). "NMR spectral analysis of polyphenols from Punica granatum". Phytochemistry. 36 (3): 793. Bibcode:1994PChem..36..793N. doi:10.1016/S0031-9422(00)89820-9.

v t e Types of pomegranate ellagitannins
Aglycones	Ellagic acid Gallagic acid Gallic acid Hexahydroxydiphenic acid
Sugars	Glucose Gluconic acid
Examples	Casuarinin Gallagyldilactone Granatin A and B Pedunculagin Punicacortein A, B, C and D 5-O-galloylpunicacortein D Punicafolin Punigluconin Punicalagin 1-alpha-O-Galloylpunicalagin Punicalin 2-O-galloyl-punicalin Strictinin
Category