Punicalagin

Punicalagin
Other names

2,3-(S)-hexahydroxydiphenoyl-4,6-(S,S)-gallagyl-D-glucose
Identifiers
CAS number 65995-63-3 Y
PubChem 16129869
ChEMBL CHEMBL506814 N
Jmol-3D images Image 1
Properties
Molecular formula C48H28O30
Molar mass 1084.71 g/mol
Exact mass 1084.06654
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Punicalagin is an ellagitannin, a polyphenol compound which are isomers of 2,3-(S)-hexahydroxydiphenoyl-4,6-(S,S)-gallagyl-D-glucose, hydrolysable tannins with a molecular weight of 1084. They are found in forms alpha and beta in pomegranates. Punicalagins are the largest molecule found intact in rat plasma after oral ingestion[1] and were found to show no toxic effects in rats who were given a 6% diet of punicalagins for 37 days.[2] Punicalagins are also found to be the major component responsible for pomegranate juice's antioxidant and health benefits.[3]

Punicalagin is water soluble and has high bioavailability. They are known to hydrolyze into smaller polyphenols such as ellagic acid in vivo where one potential mechanism is hydrolysis across the mitochondrial membrane of cultured human colon cells.[4][5]

Contents

Extract

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 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.[6]

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.[7]

Plants

As the chemistry of punicalagin became known it was found to be not unique to pomegranate. Punicalagin is 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 (a Mediterranean shrub) and Combretum molle (an African shrub).

References

  1. ^ Cerda et al. Eur J Nutr. 2003 Jan;42(1), pp. 18-28
  2. ^ Cerda et al. J. Agric. Food Chem. 2003, 51, pp. 3493-3501
  3. ^ Gil et al. J Agric Food Chem 2000 48 (10), pp. 4581-4589
  4. ^ Seeram et al. Clin Chim Acta. 2004 Oct;348(1-2), pp. 63-68
  5. ^ Larrosa et al. J Nutr Biochem. 2006 Sep;17(9), pp. 611-625
  6. ^ Seeram et al. J Nutr Biochemistry 2005 (16), pp. 360-367
  7. ^ Mertens-Talcott et al. J Agric Food Chem. 2006 Nov 15, 54(23), pp. 8956-8961

External links

Types of ellagitannins
Aglycones
Examples
Acetonyl geraniin | Castalagin (Vescalagin) | Castalin | Casuarictin | Casuariin | Casuarinin | Cornusiin E | Elaeocarpusin | Euphorscopin | Geraniin | Grandinin | Helioscopin B, Helioscopinin A | Helioscopinin B | Jolkinin | Lambertianin C | Macranganin | Pedunculagin | Punicacortein C | Punigluconin | Punicalagin | 1-alpha-O-galloylpunicalagin | Punicalin | 2-O-galloyl-punicalin | Raspberry ellagitannin | Roburin A | Roburin B | Roburin C | Roburin D | Roburin E | Rugosin E | Sanguiin H-6 | Stachyurin | Strictinin | Supinanin | Tellimagrandin II | Teracatain | Terchebulin | Terflavin A | Terflavin B
Other