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Corilagin

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Corilagin
Chemical structure of corilagin
Names
IUPAC name oxan-4-yl] 3,4,5-trihydroxybenzoate
Other names beta-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-d-glucose
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: RNKMOGIPOMVCHO-SJMVAQJGBQ
SMILES
  • O12COC(=O)c3cc(O)c(O)c(O)c3c4c(O)c(O)c(O)cc4C(=O)O1(O)(OC(=O)c5cc(O)c(O)c(O)c5)O2
  • c1c(cc(c(c1O)O)O)C(=O)OC2((((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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

It is a weak carbonic anhydrase inhibitor.

Ellagic acid and corilagin inhibit TGF-β1–dependent EMT and has been shown to attenuate fibrogenesis in a mouse model. Fibrosis is also indicated in many health conditions, including skin aging and MRSA susceptibility.

References

  1. Schmidt OT, Lademann R (1951). "Corilagin, ein weiterer kristallisierter Gerbstoff aus Dividivi. X. Mitteilung über natürliche Gerbstoffe". Justus Liebigs Annalen der Chemie. 571 (3): 232–237. doi:10.1002/jlac.19515710305.
  2. Schmidt OT, Schmidt DM (1952). "Die Umwandlung von Chebulagsäure in Corilagin XIV. Mitteilung über natürliche Gerbstoffe". Justus Liebigs Annalen der Chemie. 578: 25–30. doi:10.1002/jlac.19525780105.
  3. Tanaka T, Nonaka GI, 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.
  4. Satomi H, Umemura K, Ueno A, Hatano T, Okuda T, Noro T (August 1993). "Carbonic anhydrase inhibitors from the pericarps of Punica granatum L". Biological & Pharmaceutical Bulletin. 16 (8): 787–90. doi:10.1248/bpb.16.787. PMID 8220326.
  5. Wei Y, Kim TJ, Peng DH, Duan D, Gibbons DL, Yamauchi M, et al. (October 2017). "Fibroblast-specific inhibition of TGF-β1 signaling attenuates lung and tumor fibrosis". The Journal of Clinical Investigation. 127 (10): 3675–3688. doi:10.1172/JCI94624. PMC 5617667. PMID 28872461.
  6. "Researchers identify how skin ages, loses fat and immunity". medicalxpress.com. Retrieved 5 January 2019.
Types of ellagitannins
Moieties
Lactones
Monomers
C-glycosidic ellagitannins
Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)
Transformed ellagitannins
molecules with chebulic acid
molecules with Elaeocarpusinic acid
Oligomers
Dimers
Agrimoniin
Cornusiin E (dimer of tellimagrandin II)
Lambertianin A and B
Nobotanin B
Roburin A, B, C and D
Sanguiin H-6
Trimers
Lambertianin C
Raspberry ellagitannin
Tetramers
Lambertianin D
Nobotanin S
Pentamer
Melastoflorin A
Other
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