Punicafolin

Punicafolin
	Chemical structure of punicafolin source ↗
Names
	Other names 1,2,4-tri-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-β-D-glucose
Identifiers
CAS Number	88847-11-4[1];
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL507308;
ChemSpider	4478779;
PubChem CID	5320800;
CompTox Dashboard (EPA)	DTXSID101030158 ;
	InChI InChI=1S/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)64-33-23-9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(8-22(49)30(54)32(25)56)40(61)65-34(33)35(66-37(58)11-3-17(44)27(51)18(45)4-11)41(63-23)67-38(59)12-5-19(46)28(52)20(47)6-12/h1-8,23,33-35,41-56H,9H2/t23-,33-,34+,35-,41+/m1/s1 Key: DPBVYZVSXAZMAY-UUUCSUBKSA-N;
	SMILES Oc4c(O)cc(cc4O)C(=O)OC6C(OC(=O)c(cc1O)c-5c(O)c1O)C(OC(=O)c(cc7O)cc(O)c7O)C(OC(=O)c(cc3O)cc(O)c3O)OC6COC(=O)c(cc(O)c2O)c-5c2O;
Properties
Chemical formula	C41H30O26
Molar mass	938.63 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Punicafolin is an ellagitannin from the leaves of Punica granatum (pomegranate)¹ and in Phyllanthus emblica.²

Punicafolin is an isomer of tellimagrandin II and nupharin A, but the hexahydroxydiphenoyl group is not attached to the same hydroxyl groups in the glucose molecule.

Punicafolin has been shown to have tumor suppressive effects in dogs.³

References

Tanaka, T.; Nonaka, G. I.; Nishioka, I. (1985). "Punicafolin, an ellagitannin from the leaves of Punica granatum". Phytochemistry. 24 (9): 2075–2078. Bibcode:1985PChem..24.2075T. doi:10.1016/S0031-9422(00)83125-8.
Zhang, Y. J.; Abe, T.; Tanaka, T.; Yang, C. R.; Kouno, I. (2001). "Phyllanemblinins A-F, new ellagitannins from Phyllanthus emblica". Journal of Natural Products. 64 (12): 1527–1532. doi:10.1021/np010370g. PMID 11754604.
Tanimura S et al (2005) Suppression of tumor cell invasiveness by hydrolyzable tannins (plant polyphenols) via the inhibition of matrix metalloproteinase-2/-9 activity. Biochem Biophys Res Commun 330(4):1306-1313