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Punicalagin

From Wikipedia, the free encyclopedia
Punicalagin
Chemical structure of punicalagin
Chemical structure of punicalagin
Names
Other names
2,3-(S)-hexahydroxydiphenoyl-4,6-(S,S)-gallagyl-D-glucose
α-punicalagin
β-punicalagin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C48H28O30/c49-10-1-6-17(31(59)27(10)55)19-23-21-22-24(47(70)76-38(21)35(63)33(19)61)20(34(62)36(64)39(22)75-46(23)69)18-9(4-13(52)28(56)32(18)60)43(66)74-37-14(5-72-42(6)65)73-48(71)41-40(37)77-44(67)7-2-11(50)25(53)29(57)15(7)16-8(45(68)78-41)3-12(51)26(54)30(16)58/h1-4,14,37,40-41,48-64,71H,5H2
    Key: ZJVUMAFASBFUBG-UHFFFAOYSA-N
  • 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
Properties
C48H28O30
Molar mass 1084.71 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Punicalagin (Pyuni-cala-jen) is an ellagitannin, a type of phenolic compound. It is occurs as alpha and beta isomers in pomegranates (Punica granatum), Terminalia catappa, Terminalia myriocarpa,[1] and in Combretum molle, the velvet bushwillow, a plant species found in South Africa.[2] These three genera are all Myrtales and the last two are both Combretaceae.

Research

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Punicalagins are water-soluble and hydrolyze into smaller phenolic compounds, such as ellagic acid.

In animal studies, no toxic effects were observed in rats fed a 6% diet containing punicalagins for 37 days.[3] In laboratory research, punicalagins exhibited carbonic anhydrase inhibitory activity.[4]

See also

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References

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  1. ↑ Marzouk, M. S. A.; El-Toumy, S. A. A.; Moharram, F. A.; Shalaby, N. M.; Ahmed, A. A. (2002). "Pharmacologically Active Ellagitannins from Terminalia myriocarpa". Planta Medica. 68 (6): 523–527. Bibcode:2002PlMed..68..523M. doi:10.1055/s-2002-32549. PMID 12094296.
  2. ↑ 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): 613–617. doi:10.1002/ptr.897. PMID 11746844. S2CID 24511496.
  3. ↑ Cerdá, B; Cerón, J. J; Tomás-Barberán, F. A; Espín, J. C (2003). "Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic". Journal of Agricultural and Food Chemistry. 51 (11): 3493–501. Bibcode:2003JAFC...51.3493C. doi:10.1021/jf020842c. PMID 12744688.
  4. ↑ 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.
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