Punicalin - Misplaced Pages

Punicalin
Names

Other names 4,6-(S,S)-Gallagyl-D-glucose
Identifiers
CAS Number	65995-64-4
3D model (JSmol)	Interactive image
ChemSpider	28428695
PubChem CID	5388496
InChI InChI=1S/C34H22O22/c35-6-1-4-9(19(39)17(6)37)11-15-13-14-16(33(50)56-28(13)23(43)21(11)41)12(22(42)24(44)29(14)55-32(15)49)10-5(2-7(36)18(38)20(10)40)31(48)54-27-8(3-52-30(4)47)53-34(51)26(46)25(27)45/h1-2,8,25-27,34-46,51H,3H2/t8-,25-,26-,27-,34?/m1/s1Key: IQHIEHIKNWLKFB-OBOTWMKHSA-N InChI=1/C34H22O22/c35-6-1-4-9(19(39)17(6)37)11-15-13-14-16(33(50)56-28(13)23(43)21(11)41)12(22(42)24(44)29(14)55-32(15)49)10-5(2-7(36)18(38)20(10)40)31(48)54-27-8(3-52-30(4)47)53-34(51)26(46)25(27)45/h1-2,8,25-27,34-46,51H,3H2/t8-,25-,26-,27-,34?/m1/s1Key: IQHIEHIKNWLKFB-OBOTWMKHBV
SMILES c1c2c(c(c(c1O)O)O)-c3c4c5c6c(c(c(c(c6oc4=O)O)O)-c7c(cc(c(c7O)O)O)C(=O)O8(COC2=O)OC((8O)O)O)c(=O)oc5c(c3O)O
Properties
Chemical formula	C₃₄H₂₂O₂₂
Molar mass	782.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Punicalin is an ellagitannin. It can be found in Punica granatum (pomegranate) or in the leaves of Terminalia catappa, a plant used to treat dermatitis and hepatitis. It is also reported in Combretum glutinosum, all three species being Myrtales, the two last being Combretaceae.

Chemistry

The molecule contains a gallagic acid component linked to a glucose.

Zhang, Y.; Wang, D.; Lee, R. P.; Henning, S. M.; Heber, D. (2009). "Absence of Pomegranate Ellagitannins in the Majority of Commercial Pomegranate Extracts: Implications for Standardization and Quality Control". Journal of Agricultural and Food Chemistry. 57 (16): 7395–7400. doi:10.1021/jf9010017. PMID 20349921.
Lin, C. C.; Hsu, Y. F.; Lin, T. C.; Hsu, F. L.; Hsu, H. Y. (1998). "Antioxidant and hepatoprotective activity of punicalagin and punicalin on carbon tetrachloride-induced liver damage in rats". The Journal of Pharmacy and Pharmacology. 50 (7): 789–794. doi:10.1111/j.2042-7158.1998.tb07141.x. PMID 9720629. S2CID 8639399.
Lin, Chun-Ching; Hsu, YF; Lin, TC (1999). "Effects of punicalagin and punicalin on carrageenan-induced inflammation in rats". The American Journal of Chinese Medicine. 27 (3 & 4): 371–376. doi:10.1142/S0192415X99000422. PMID 10592846.
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.

Moieties

Lactones

Monomers

C-glycosidic ellagitannins

Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)

Transformed ellagitannins

molecules with chebulic acid	Chebulagic acid Chebulinic acid
molecules with Elaeocarpusinic acid	Elaeocarpusin Helioscopin B Mallojaponin (1-O-Galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-beta-D-glucose)

Oligomers

Dimers: Agrimoniin; Cornusiin E (dimer of tellimagrandin II); Lambertianin A and B; Nobotanin B; Roburin A, B, C and D; Sanguiin H-6

Other

v t e Types of pomegranate ellagitannins
Aglycones	Ellagic acid Gallagic acid Gallic acid Hexahydroxydiphenic acid
Sugars	Glucose Gluconic acid
Examples	Casuarinin Gallagyldilactone Granatin A and B Pedunculagin Punicacortein A, B, C and D 5-O-galloylpunicacortein D Punicafolin Punigluconin Punicalagin 1-alpha-O-Galloylpunicalagin Punicalin 2-O-galloyl-punicalin Strictinin

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