Pomegranate ellagitannin

From Wikipedia, the free encyclopedia
  (Redirected from Punicalagins)
Jump to: navigation, search
Pomegranate fruit, opened.

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

Occurrence in other plants[edit]

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 antiobiotic and antifungal purposes). They have also been isolated from Cistus salvifolius[1][2] (a Mediterranean shrub) and Combretum molle (an African shrub).[3]

Extracts and health effects[edit]

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. It has been recommended[who?] to look for pomegranate ingredients that mimic the polyphenol ratio of the fruit, as potent synergistic effects have been observed in 'natural spectrum' extracts, especially pomegranate concentrate normalized to punicalagins.[4]

A pomegranate extract standardized to punicalagins marketed under the name Pomella was found to absorb into the bloodstream after consumption in humans. A maximum 32% increase in plasma antioxidant status measured by ORAC was also noted in this study.[5]

Pomegranate fruits natural phenols can be extracted with ethyl acetate and fractionation can afford the ellagitannin punicalagins. The substance was found to be active against methicillin-resistant Staphylococcus aureus strains.[6]

Pomegranate ellagitannins may have an impact on human gut flora, inhibiting the growth of pathogenic clostridia and Staphylococcus aureus, while probiotic lactobacilli and bifidobacteria are generally not affected by ellagitannins.[7] Urolithins are microflora human metabolites produced from ellagic acid derivatives.

Punicalagins are the largest molecules found intact in rat plasma after oral ingestion[8] and were found to show no toxic effects in rats who were given a 6% diet of punicalagins for 37 days.[9] Punicalagins are also found to be the major component responsible for pomegranate juice's antioxidant and health benefits.[10]

In vitro studies shows that ellagitannins extracted from the fruit rind of P. granatum may be helpful against malaria.[11]

List of compounds[edit]

other phenolics

See also[edit]

References[edit]

  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. 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. 
  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. 
  4. ^ Seeram, NP; Adams, LS; Henning, SM; Niu, Y; Zhang, Y; Nair, MG; Heber, D (2005). "In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice". The Journal of nutritional biochemistry 16 (6): 360–7. doi:10.1016/j.jnutbio.2005.01.006. PMID 15936648. 
  5. ^ Mertens-Talcott, SU; Jilma-Stohlawetz, P; Rios, J; Hingorani, L; Derendorf, H (2006). "Absorption, metabolism, and antioxidant effects of pomegranate (Punica granatum l.) polyphenols after ingestion of a standardized extract in healthy human volunteers". Journal of agricultural and food chemistry 54 (23): 8956–61. doi:10.1021/jf061674h. PMID 17090147. 
  6. ^ Machado, Thelma de B.; Leal, Ivana C. R.; Amaral, Ana Claudia F.; Santos, Kátia R. N. dos; Silva, Marlei G. da; Kuster, Ricardo M. (2002). "Antimicrobial Ellagitannin of Punica granatum Fruits". Journal of the Brazilian Chemical Society 13 (5): 606. doi:10.1590/S0103-50532002000500010. 
  7. ^ Bialonska, Dobroslawa; Kasimsetty, Sashi G.; Schrader, Kevin K.; Ferreira, Daneel (2009). "The Effect of Pomegranate (Punica granatumL.) Byproducts and Ellagitannins on the Growth of Human Gut Bacteria". Journal of Agricultural and Food Chemistry 57 (18): 8344–9. doi:10.1021/jf901931b. PMID 19705832. 
  8. ^ Scalbert A, Morand C, Manach C, Rémésy C (August 2002). "Absorption and metabolism of polyphenols in the gut and impact on health". Biomed. Pharmacother. 56 (6): 276–82. doi:10.1016/S0753-3322(02)00205-6. PMID 12224598. 
  9. ^ Cerdá B, Cerón JJ, Tomás-Barberán FA, Espín JC (May 2003). "Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic". J. Agric. Food Chem. 51 (11): 3493–501. doi:10.1021/jf020842c. PMID 12744688. 
  10. ^ Gil MI, Tomás-Barberán FA, Hess-Pierce B, Holcroft DM, Kader AA (October 2000). "Antioxidant activity of pomegranate juice and its relationship with phenolic composition and processing". J. Agric. Food Chem. 48 (10): 4581–9. doi:10.1021/jf000404a. PMID 11052704. 
  11. ^ Dell'Agli, Mario; Galli, Germana V; Bulgari, Michela; Basilico, Nicoletta; Romeo, Sergio; Bhattacharya, Deepak; Taramelli, Donatella; Bosisio, Enrica (2010). "Ellagitannins of the fruit rind of pomegranate (Punica granatum) antagonize in vitro the host inflammatory response mechanisms involved in the onset of malaria". Malaria Journal 9: 208. doi:10.1186/1475-2875-9-208. PMC 2912927. PMID 20642847. 
  12. ^ a b c 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.  edit
  13. ^ a b c El-Toumy, Sayed A.A; Rauwald, Hans W (2002). "Two ellagitannins from Punica granatum heartwood". Phytochemistry 61 (8): 971–4. doi:10.1016/S0031-9422(02)00435-1. PMID 12453528. 
  14. ^ a b c Tanaka, Takashi; Nonaka, Gen-Ichiro; Nishioka, Itsuo (1985). "Punicafolin, an ellagitannin from the leaves of Punica granatum". Phytochemistry 24 (9): 2075. doi:10.1016/S0031-9422(00)83125-8. 
  15. ^ a b c d e f Nawwar, Mahmoud A.M.; Hussein, Sahar A.M.; Merfort, Irmgard (1994). "NMR spectral analysis of polyphenols from Punica granatum". Phytochemistry 36 (3): 793. doi:10.1016/S0031-9422(00)89820-9.