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CORILAGIN

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CORILAGIN Basic information

Product Name:
CORILAGIN
Synonyms:
  • 1-O-Galloyl-3-O,6-O-[2,2',3,3',4,4'-hexahydroxy[1,1'-biphenyl]-6,6'-diylbiscarbonyl]-β-D-glucopyranose
  • Galloyl 3-O,6-O-[(4,4',5,5',6,6'-hexahydroxy-1,1'-biphenyl-2,2'-diyl)biscarbonyl]-β-D-glucopyranoside
  • CORILAGIN(SH)
  • CORILAGIN
  • B-D-GLUCOPYRANOSE, CYCLIC 3,6-(4,4',5,5',6,6'-HEXAHYDROXY[1,1'-BIPHENYL]-2,2'-DICARBOXYLATE)1-(3,4,5-TRIHYDROXYBENZOATE), (R)-
  • 1-O-GALLOYL-3,6-HEXAHYDROXYDIPHENOYL-BETA-D-GLUCOPYRANOSE
  • CORILAGIN: B-D-GLUCOPYRANOSE, CYCLIC3,6-(4,4',5,5',6,6'-HEXAHYDROXY[1,1'-BIPHENYL]-2,2'-DICARBOXYLATE)1-(3,4,5-TRIHYDROXYBENZOATE), (R)-,
  • 1-O-Galloyl-3,6-hexahydroxydiphenol-b-D-Glucopyranose
CAS:
23094-69-1
MF:
C27H22O18
MW:
634.46
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Carbohydrates & Derivatives
  • Miscellaneous Natural Products
Mol File:
23094-69-1.mol
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CORILAGIN Chemical Properties

Melting point:
>200°C dec
Boiling point:
1280.8±65.0 °C(Predicted)
Density 
2.11±0.1 g/cm3(Predicted)
storage temp. 
Inert atmosphere,2-8°C
solubility 
H2O: soluble1mg/mL, clear, colorless
pka
7.53±0.70(Predicted)
form 
Solid
color 
Off-White
Water Solubility 
H2O: 1mg/mL, clear, colorless
Stability:
Hygroscopic
InChIKey
TUSDEZXZIZRFGC-XIGLUPEJSA-N
SMILES
OC1C(=C(O)C=C2C(OC3C(O)C(OC(OC(C4C=C(O)C(O)=C(O)C=4)=O)C3O)COC(=O)C3=CC(O)=C(O)C(O)=C3C=12)=O)O
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Safety Information

WGK Germany 
3
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CORILAGIN Usage And Synthesis

Description

Corilagin is a polyphenol and hydrolyzable tannin that can be isolated from a variety of plants. It inhibits squalene epoxidase (IC50 = 4.0 μM), a key enzyme in cholesterol synthesis. Corilagin also has various anti-inflammatory and anti-cancer effects.

Chemical Properties

Off-White Solid

Uses

Thrombolytic.

Definition

ChEBI: An ellagitannin with a hexahydroxydiphenoyl group bridging over the 3-O and 6-O of the glucose core.

in vivo

Corilagin (15 mg/kg, i.p., for 7 days) shows anti-tumor activity in Hep3B hepatocellular carcinoma[4].
Corilagin (0-20 mg/kg, i.p.) prevents APAP-induced hepatotoxicity in mice[5].
Corilagin (10 and 100 mg/kg, i.p.) ameliorates Bleomycin-induced pulmonary fibrosis in mice[6].

Animal Model:Hep3B hepatocellular carcinoma mouse model[4].
Dosage:15 mg/kg
Administration:Intraperitoneal injection (i.p.)
Result:Inhibited tumor growth without toxic effects.
Animal Model:APAP-induced hepatotoxicity in mice[5]
Dosage:0, 1, 5, 10, 20 mg/kg
Administration:Intraperitoneal injection (i.p.)
Result:Decreased APAP-induced serum ALT level, hepatic myeloperoxidase (MPO) activity, cytokines (TNF-α, IL-1β, and IL-6) production, malondialdehyde (MDA) activity, and ERK/JNK MAPK and NF-κB protein expressions.

References

[1] IKURO ABE. Ellagitannins and Hexahydroxydiphenoyl Esters as Inhibitors of Vertebrate Squalene Epoxidase[J]. Journal of Natural Products , 2001, 64 8: 1010-1014. DOI: 10.1021/np010100y
[2] ROBERTO GAMBARI . Corilagin is a potent inhibitor of NF-kappaB activity and downregulates TNF-alpha induced expression of IL-8 gene in cystic fibrosis IB3-1 cells[J]. International immunopharmacology, 2012, 13 3: Pages 308-315. DOI: 10.1016/j.intimp.2012.04.010
[3] HAI-TAO XIAO. Inhibitory Effect of the Gallotannin Corilagin on Dextran Sulfate Sodium-Induced Murine Ulcerative Colitis[J]. Journal of Natural Products , 2013, 76 11: 2120-2125. DOI: 10.1021/np4006772
[4] LUOQI JIA. A potential anti-tumor herbal medicine, Corilagin, inhibits ovarian cancer cell growth through blocking the TGF-β signaling pathways.[J]. BMC Complementary and Alternative Medicine, 2013: 33. DOI: 10.1186/1472-6882-13-33
[5] ROBERTO GAMBARI. Sensitization of Hep3B hepatoma cells to cisplatin and doxorubicin by corilagin.[J]. Phytotherapy Research, 2014, 28 5: 781-783. DOI: 10.1002/ptr.5049

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