Stereochemistry | ACHIRAL |
Molecular Formula | C21H20O6 |
Molecular Weight | 368.3799 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O
InChI
InChIKey=VFLDPWHFBUODDF-FCXRPNKRSA-N
InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+
Curcumin is a bright yellow chemical produced by some plants, for example, it is the principal curcuminoid of turmeric. It is sold as a food flavoring, food colorant, herbal supplement, and cosmetic ingredient. Although curcumin has been widely studied it has not been officially endorsed for any pharmaceutical use due to issues of stability and bioavailability; although it continues to b marketed as a health supplement. Curcumin has been investigated for the treatment of a number of cancers, asthma, mucositis, schizophrenia, mild cognitive impairment, and depression.
CNS Activity
Approval Year
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Drug as perpetrator
Drug as victim
Tox targets
PubMed
Patents
Sample Use Guides
Patients with a history of stable persistent asthma and allergic sensitivities received oral supplementation of 2000 mg of curcumin.
Route of Administration:
Oral
Human colorectal adenocarcinoma cells (Caco-2) were grown at 37 deg-C under a 5% CO2 were plated at a density of 40,000 cells per well in minimum essential medium, supplemented with 20% fetal bovine serum, 1 mM sodium pyruvate, 0.1 mM nonessential amino acids, 100 units/mL penicillin and 100 micro-g/mL streptomycin. Transfection was conducted with each well receiving 1 μL of Lipofectamine Reagent, 2 μL of Plus Reagent, 500 ng of pTZ18U carrier DNA plasmid, and 20 ng of pRL-null. Each well also received 250 ng of pLuc-MCS plasmid containing an oligonucleotide with two copies of a nuclear receptor responsive element upstream of the firefly luciferase gene. In addition to the responsive element reporter constructs, cells were also cotransfected with 50 ng of a pSG5-based expression plasmid containing the appropriate nuclear receptor. The cells received both 50 ng of pSG5-VDR (vitamin D receptor), and 20 ng of pSG5-RXRα when the VDRE-containing reporter was employed. The cells were treated with known nuclear receptor ligands or curcumin (6.7 and 10 microM), 18 hours after completion of transfection; treatment times ranged from 24 to 30 hours. After incubation with ligands, cells were collected and the amount of reporter gene product (luciferase) produced in the cells was measured using the Dual-Luciferase® Reporter Assay System. Cells treated with 6.7 and 10 microM curcumin demonstrated a dose-dependent increase in the level of transcription of the VDRE-reporter plasmid of 2.1 and 5.0 fold respectively.