Jump to content

Punicalagin: Difference between revisions

Browse history interactively
Page 1
Page 2
← Previous edit
Content deleted Content added
VisualWikitext
→Research: use wikimarkup
 
(61 intermediate revisions by 26 users not shown)
Line 1: Line 1:
{{chembox
{{chembox
| Verifiedfields = changed
⚫
| Name = Punicalagin
| verifiedrevid = 400995112
⚫
| ImageFile = Punicalagin.PNG
⚫
| Name = Punicalagin
| ImageSize = 250px
⚫
| ImageFile = Punicalagin1.png
⚫
| ImageName = Chemical structure of punicalagin
| IUPACName =
| ImageSize = 228px
⚫
| ImageName = Chemical structure of punicalagin
⚫
| OtherNames = 2,3-(S)-hexahydroxydiphenoyl-4,6-(S,S)-[[gallagyl]]-D-glucose
| IUPACName =
⚫
| Section1= {{Chembox Identifiers
⚫
| OtherNames = 2,3-(S)-hexahydroxydiphenoyl-4,6-(S,S)-[[gallagyl]]-D-glucose<br>α-punicalagin<br>β-punicalagin
⚫
| CASNo = 65995-63-3
⚫
|Section1={{Chembox Identifiers
⚫
| PubChem = 16129869
| CASNo_Ref = {{cascite|correct|??}}
⚫
| SMILES = C1C(C(OC(=O)C2=CC(=C(C(=C2C3=C(C(=C4C5=C3C(=O)OC6=C(C(=C(C7=C(C(=C(C=C7C(=O)O1)O)O)O)C(=C56)C(=O)O4)O)O)O)O)O)O)O)C8C(OC(=O)C9=CC(=C(C(=C9C1=C(C(=C(C=C1C(=O)O8)O)O)O)O)O)O)C=O)O
⚫
| CASNo = 65995-63-3
⚫
| PubChem = 16129869
| KEGG = C22601
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 506814
⚫
| SMILES = C1C(C(OC(=O)C2=CC(=C(C(=C2C3=C(C(=C4C5=C3C(=O)OC6=C(C(=C(C7=C(C(=C(C=C7C(=O)O1)O)O)O)C(=C56)C(=O)O4)O)O)O)O)O)O)O)C8C(OC(=O)C9=CC(=C(C(=C9C1=C(C(=C(C=C1C(=O)O8)O)O)O)O)O)O)C=O)O
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>48</sub>H<sub>28</sub>O<sub>30</sub>
| Formula = C<sub>48</sub>H<sub>28</sub>O<sub>30</sub>
| MolarMass = 1084.71 g/mol
| MolarMass = 1084.71 g/mol
⚫
| Appearance =
| ExactMass = 1084.06654
| Density=
⚫
| Appearance =
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
⚫
| Solubility =
| BoilingPt=
⚫
| Solubility =
}}
}}
|Section3= {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}
'''Punicalagin''' (''Pyuni-cala-jen'') is an [[ellagitannin]], a type of [[phenolic compound]]. It is found as alpha and beta isomers in [[pomegranate]]s (''Punica granatum''), ''[[Terminalia catappa]]'', ''[[Terminalia myriocarpa]]'',<ref>{{Cite journal | last1 = Marzouk | first1 = M. S. A. | last2 = El-Toumy | first2 = S. A. A. | last3 = Moharram | first3 = F. A. | last4 = Shalaby | first4 = N. M. | last5 = Ahmed | first5 = A. A. | title = Pharmacologically Active Ellagitannins from Terminalia myriocarpa | doi = 10.1055/s-2002-32549 | journal = Planta Medica | url = https://pubmed.ncbi.nlm.nih.gov/12094296/ | volume = 68 | issue = 6 | pages = 523–527 | year = 2002 | pmid = 12094296}}</ref> and in ''[[Combretum molle]]'', the velvet bushwillow, a plant species found in South Africa.<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. | url = https://pubmed.ncbi.nlm.nih.gov/11746844/ | doi = 10.1002/ptr.897 | title = In vitro antiprotozoal activity of extract and compounds from the stem bark of Combretum molle | journal = Phytotherapy Research | volume = 15 | issue = 7 | pages = 613–617 | year = 2001 | pmid = 11746844| s2cid = 24511496 }}</ref> These three genera are all [[Myrtales]] and the last two are both [[Combretaceae]].
'''Punicalagins''' are [[tannins]], large polyphenol compounds 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 [[pomegranate]]s. Punicalagins are the largest molecule found intact in rat plasma after oral ingestion<ref>Cerda et al. Eur J Nutr. 2003 Jan;42(1):18-28.
</ref> and were found to show no toxic effects in rats who were given a 6% diet of punicalagins for 37 days.<ref>Cerda et al. J. Agric. Food Chem. 2003, 51, 3493-3501
</ref> Punicalagins are also found to be the major component responsible for [[pomegranate]] juice's antioxidant and health benefits.<ref>Gil et al. J Agric Food Chem 2000 48 (10) 4581-89
⚫
</ref>


== Research ==
Punicalagins are water soluble and have high bioavailability. They are known to hydrolyze into smaller polyphenols such as [[ellagic acid]] in vivo where one potential mechanism is hydrolysis across the [[Mitochondrion|mitochondrial]] membrane of cultured human colon cells.<ref>Seeram et al. Clin Chim Acta. 2004 Oct;348(1-2):63-8.</ref><ref>Larrosa et al. J Nutr Biochem. 2006 Sep;17(9):611-25.</ref>
Punicalagins are water-soluble and [[hydrolyze]] into smaller phenolic compounds, such as [[ellagic acid]].


There were no toxic effects in rats on a 6% diet of punicalagins for 37 days.<ref>{{cite journal|pmid=12744688|year=2003|last1=Cerdá|url=https://pubmed.ncbi.nlm.nih.gov/12744688/|first1=B|title=Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic|journal=Journal of Agricultural and Food Chemistry|volume=51|issue=11|pages=3493–501|last2=Cerón|first2=J. J|last3=Tomás-Barberán|first3=F. A|last4=Espín|first4=J. C|doi=10.1021/jf020842c}}</ref> In laboratory research, punicalagins had [[carbonic anhydrase inhibitor]] activity.<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. |title = Carbonic anhydrase inhibitors from the pericarps of Punica granatum L |journal = Biological & Pharmaceutical Bulletin |volume = 16 |issue = 8 |pages = 787–790 |year = 1993 |pmid = 8220326 |doi=10.1248/bpb.16.787|doi-access = free
A study in Taiwan showed that [[punicalagin alpha]] shows potential as strong cancer suppressors.{{Fact|date=February 2009}}
⚫
}}</ref>


==Extract==
==See also==
* [[Ellagic acid]]
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|date=March 2009}} 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.<ref>Seeram et al. J Nutr Biochemistry 2005 (16) 360-367.</ref>
* [[ Punicic acid]]


⚫
== References ==
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 [[Oxygen radical absorbance capacity|ORAC]] was also noted in this study.<ref>Mertens-Talcott et al. J Agric Food Chem. 2006 Nov 15;54(23):8956-8961</ref>
{{Reflist}}


{{ellagitannin}}
==Plants==
{{pomegranate ellagitannin}}
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 (plant)|Terminalia]], species [[Terminalia chebula|chebula]] Retz. (“Fructus Chebulae”), [[Terminalia myriocarpa|myriocarpa]], [[Terminalia catappa|catappa]] and [[Terminalia citrina|citrina]] (tropical flowering trees historically used in African traditional medicine for antiobiotic and antifungal purposes). They have also been isolated from [[Cistus salvifolius]] (Mediterranean shrub) and [[Combretum molle]] (African shrub).


[[Category:Pomegranate ellagitannins]]
⚫
==References==
[[Category:Carbonic anhydrase inhibitors]]
<references/>

==External links==
* [http://www.pomextract.com] Pomella

{{Hydrolysable tannin}}

[[category:Tannins]]
[[Category:Nutrition]]
[[Category:Pyrogallols]]
Retrieved from "https://en.wikipedia.org/wiki/Special:ComparePages"