{{short description|Ellagitannins found in the pomegranate fruit}} {{Notability|date=May 2023}} thumb|Pomegranate fruit, opened. 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 == 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'', ''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''<ref>{{Cite journal |last1=Barrajón-Catalán |first1=Enrique |last2=Fernández-Arroyo |first2=Salvador |last3=Roldán |first3=Cristina |last4=Guillén |first4=Emilio |last5=Saura |first5=Domingo |last6=Segura-Carretero |first6=Antonio |last7=Micol |first7=Vicente |year=2011 |title=A systematic study of the polyphenolic composition of aqueous extracts deriving from several Cistus genus species: Evolutionary relationship |journal=Phytochemical Analysis |volume=22 |issue=4 |pages=303–12 |doi=10.1002/pca.1281 |pmid=21259376|bibcode=2011PChAn..22..303B }}</ref><ref>{{Cite journal |last1=Saracini |first1=E. |last2=Tattini |first2=M. |last3=Traversi |first3=M. L. |last4=Vincieri |first4=F. F. |last5=Pinelli |first5=P. |year=2005 |title=Simultaneous LC-DAD and LC-MS Determination of Ellagitannins, Flavonoid Glycosides, and Acyl-Glycosyl Flavonoids in Cistus salvifolius L. Leaves |journal=Chromatographia |volume=62 |issue=5–6 |pages=245 |doi=10.1365/s10337-005-0623-7|s2cid=93426386 }}</ref> (a Mediterranean shrub) and ''Combretum molle'' (an African shrub).<ref name="Asres2">{{Cite journal |last1=Asres |first1=K. |last2=Bucar |first2=F. |last3=Knauder |first3=E. |last4=Yardley |first4=V. |last5=Kendrick |first5=H. |last6=Croft |first6=S. L. |year=2001 |title=In vitro antiprotozoal activity of extract and compounds from the stem bark of Combretum molle |journal=Phytotherapy Research |volume=15 |issue=7 |pages=613–7 |doi=10.1002/ptr.897 |pmid=11746844|s2cid=24511496 }}</ref>
Pomegranate fruits natural phenols can be extracted with ethyl acetate and fractionation can afford the ellagitannin punicalagins.<ref>{{Cite journal |last1=Machado |first1=Thelma de B. |last2=Leal |first2=Ivana C. R. |last3=Amaral |first3=Ana Claudia F. |last4=Santos |first4=Kátia R. N. dos |last5=Silva |first5=Marlei G. da |last6=Kuster |first6=Ricardo M. |year=2002 |title=Antimicrobial Ellagitannin of Punica granatum Fruits |journal=Journal of the Brazilian Chemical Society |volume=13 |issue=5 |pages=606 |doi=10.1590/S0103-50532002000500010 |doi-access=free}}</ref>
== 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.{{cn|date=August 2014}}
== List of compounds ==
=== Ellagitannins === * Pedunculagin, a compound found in the pericarp of the pomegranate (''Punica granatum'').<ref name="Satomi">{{Cite journal |last1=Satomi |first1=H. |last2=Umemura |first2=K. |last3=Ueno |first3=A. |last4=Hatano |first4=T. |last5=Okuda |first5=T. |last6=Noro |first6=T. |year=1993 |title=Carbonic anhydrase inhibitors from the pericarps of Punica granatum L |journal=Biological & Pharmaceutical Bulletin |volume=16 |issue=8 |pages=787–790 |doi=10.1248/bpb.16.787 |pmid=8220326 |doi-access=free}}</ref> * 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<ref name="Toumy">{{Cite journal |last1=El-Toumy |first1=Sayed A.A |last2=Rauwald |first2=Hans W |year=2002 |title=Two ellagitannins from Punica granatum heartwood |journal=Phytochemistry |volume=61 |issue=8 |pages=971–4 |doi=10.1016/S0031-9422(02)00435-1 |pmid=12453528|bibcode=2002PChem..61..971E }}</ref> * 5-O-galloylpunicacortein D<ref name=Toumy/> * 2-O-galloylpunicalin<ref name=Toumy/> * Casuarinin, a compound found in the pericarp of ''P. granatum''<ref name=Satomi/> * Gallagyldilactone, a compound found in the pericarp of ''P. granatum''<ref name=Satomi/> * Corilagin, a compound found in the leaves of ''P. granatum'' and other species * Strictinin, a compound found in the leaves of ''P. granatum''<ref name="Tanaka">{{Cite journal |last1=Tanaka |first1=Takashi |last2=Nonaka |first2=Gen-Ichiro |last3=Nishioka |first3=Itsuo |year=1985 |title=Punicafolin, an ellagitannin from the leaves of Punica granatum |journal=Phytochemistry |volume=24 |issue=9 |pages=2075 |doi=10.1016/S0031-9422(00)83125-8|bibcode=1985PChem..24.2075T }}</ref>
=== 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''<ref name=Tanaka/> * 1,2,3,4,6-penta-O-galloyl-β-D-glucose, a compound found in the leaves of ''P. granatum''<ref name=Tanaka/> and the common precursor of gallotannins and the related ellagitannins * Brevifolin, a compound found in the leaves of ''P. granatum''<ref name="Nawwar">{{Cite journal |last1=Nawwar |first1=Mahmoud A.M. |last2=Hussein |first2=Sahar A.M. |last3=Merfort |first3=Irmgard |year=1994 |title=NMR spectral analysis of polyphenols from Punica granatum |journal=Phytochemistry |volume=36 |issue=3 |pages=793 |doi=10.1016/S0031-9422(00)89820-9|bibcode=1994PChem..36..793N }}</ref> * Brevifolin carboxylic acid, a compound found in the leaves of ''P. granatum''<ref name=Nawwar/> * 3,6-(R)-hexahydroxydiphenoyl-(α/β)-C-glucopyranose, a compound found in the leaves of ''P. granatum''<ref name=Nawwar/> * 1,2,6-tri-O-galloyl-β-C-glucopyranose, a compound found in the leaves of ''P. granatum''<ref name=Nawwar/> * 1,4,6-tri-O-galloyl-β-C-glucopyranose, a compound found in the leaves of ''P. granatum''<ref name=Nawwar/> * [[3,4,8,9,10-pentahydroxydibenzo-b,d-pyran-6-one|3,4,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one]], a compound found in the leaves of ''P. granatum''<ref name=Nawwar/>
== See also == * List of antioxidants in food
== References == {{Reflist|30em}}
{{Ellagitannin}} {{Pomegranate ellagitannin}}
Category:Plants used in traditional African medicine Category:Pomegranate ellagitannins