Corilagin

Corilagin

Names
IUPAC name [3,5-dihydroxy-2-(3,4,5-trihydroxybenzoyl)oxy-6-[(3,4,5-trihydroxybenzoyl)oxymethyl]oxan-4-yl] 3,4,5-trihydroxybenzoate
Other names beta-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-d-glucose
Identifiers
CAS Number	23094-69-1=
ChEMBL	ChEMBL449392
ChemSpider	4265734
Jmol interactive 3D	Image Image
PubChem	73568
InChI InChI=1S/C27H22O18/c28-9-1-6(2-10(29)16(9)32)24(39)45-27-22(38)23-19(35)13(43-27)5-42-25(40)7-3-11(30)17(33)20(36)14(7)15-8(26(41)44-23)4-12(31)18(34)21(15)37/h1-4,13,19,22-23,27-38H,5H2/t13-,19-,22-,23+,27+/m1/s1 Key: TUSDEZXZIZRFGC-XIGLUPEJSA-N InChI=1/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(39)42-7-17-21(37)23(44-25(40)9-3-13(30)19(35)14(31)4-9)22(38)27(43-17)45-26(41)10-5-15(32)20(36)16(33)6-10/h1-6,17,21-23,27-38H,7H2/t17-,21-,22-,23+,27+/m1/s1 Key: RNKMOGIPOMVCHO-SJMVAQJGBQ
SMILES O[C@@H]1[C@H]2COC(=O)c3cc(O)c(O)c(O)c3c4c(O)c(O)c(O)cc4C(=O)O[C@@H]1[C@@H](O)[C@H](OC(=O)c5cc(O)c(O)c(O)c5)O2 c1c(cc(c(c1O)O)O)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)c3cc(c(c(c3)O)O)O)O)OC(=O)c4cc(c(c(c4)O)O)O)O
Properties
Chemical formula	C27H22O18
Molar mass	634.45 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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Infobox references

Corilagin is an ellagitannin. Corilagin was first isolated in 1951 from Dividivi extract and from Caesalpinia coriaria,^[1][2] hence the name of the molecule. It can also be found in Alchornea glandulosa and in the leaves of Punica granatum (pomegranate).^[3]

It is a weak carbonic anhydrase inhibitor.^[4]

References

1. Schmidt, O. T. .; Lademann, R. (1951). "Corilagin, ein weiterer kristallisierter Gerbstoff aus Dividivi. X. Mitteilung über natürliche Gerbstoffe". Justus Liebigs Annalen der Chemie 571 (3): 232. doi:10.1002/jlac.19515710305.
2. Schmidt, O. T.; Schmidt, D. M. (1952). "Die Umwandlung von Chebulagsäure in Corilagin XIV. Mitteilung über natürliche Gerbstoffe". Justus Liebigs Annalen der Chemie 578: 25. doi:10.1002/jlac.19525780105.
3. Tanaka, T.; Nonaka, G. I.; Nishioka, I. (1985). "Punicafolin, an ellagitannin from the leaves of Punica granatum". Phytochemistry 24 (9): 2075. doi:10.1016/S0031-9422(00)83125-8.
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.