punicalagin
{{chembox
| Verifiedfields = changed
| verifiedrevid = 400995112
| Name = Punicalagin
| ImageFile = Punicalagin1.png
| ImageSize = 228px
| ImageName = Chemical structure of punicalagin
| IUPACName =
| OtherNames = 2,3-(S)-hexahydroxydiphenoyl-4,6-(S,S)-gallagyl-D-glucose
α-punicalagin
β-punicalagin
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 65995-63-3
| PubChem = 16129869
| KEGG = C22601
| ChEBI = 167695
| 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
| Formula = C48H28O30
| MolarMass = 1084.71 g/mol
| Appearance =
| Density=
| MeltingPt=
| BoilingPt=
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
Punicalagin (Pyuni-cala-jen) is an ellagitannin, a type of phenolic compound. It is found as alpha and beta isomers in pomegranates (Punica granatum), Terminalia catappa, Terminalia myriocarpa,{{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}} and in Combretum molle, the velvet bushwillow, a plant species found in South Africa.{{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 }} These three genera are all Myrtales and the last two are both Combretaceae.
Research
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.{{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}} In laboratory research, punicalagins had carbonic anhydrase inhibitor activity.{{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
}}