Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H16O4 |
| Molecular Weight | 308.3279 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(C=C1)\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2
InChI
InChIKey=PREBVFJICNPEKM-YDWXAUTNSA-N
InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
| Molecular Formula | C19H16O4 |
| Molecular Weight | 308.3279 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23873854 | https://www.ncbi.nlm.nih.gov/pubmed/26546528 | https://www.ncbi.nlm.nih.gov/pubmed/26546528 | https://www.ncbi.nlm.nih.gov/pubmed/26777574
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23873854 | https://www.ncbi.nlm.nih.gov/pubmed/26546528 | https://www.ncbi.nlm.nih.gov/pubmed/26546528 | https://www.ncbi.nlm.nih.gov/pubmed/26777574
Bisdemethoxycurcumin (BDMC) is a minor constituent (approximately 3%) of curcuminoids that has been shown to be more stable than the other two main curcuminoids, that is, curcumin and desmethoxycurcumin. Bisdemethoxycurcumin inhibits the proliferation and survival of several types of tumor cells including colon cancer cells, breast cancer cells, leukemia cells, and glioma cells. In addition, Bisdemethoxycurcumin suppresses cancer invasion and has the highest anti-metastatic potency in HT1080 human fibrosarcoma cells among the three curcuminoids. Bisdemethoxycurcumin has been reported to possess anti-oxidant and anti-inflammatory activities. However, the underlying molecular mechanisms responsible for the inhibitory action of Bisdemethoxycurcumin on tumor invasion and migration have remained largely unknown. More interestingly, the anti-cancer effects of Bisdemethoxycurcumin are comparable to and sometimes more potent than those of curcumin in different conditions.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Curcuminoids distinctly exhibit antioxidant activities and regulate expression of scavenger receptors and heme oxygenase-1. | 2013-09 |
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| Evaluation in vitro of synthetic curcumins as agents promoting monocytic gene expression related to β-amyloid clearance. | 2012-01-13 |
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| Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. | 2010-10 |
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| Optimized turmeric extracts have potent anti-amyloidogenic effects. | 2009-12 |
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| Induction of antioxidant enzymes by curcumin and its analogues in human islets: implications in transplantation. | 2009-05 |
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| Comparative antiulcer effect of bisdemethoxycurcumin and curcumin in a gastric ulcer model system. | 2009-04 |
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| Inhibitory effect of curcuminoids on acetylcholinesterase activity and attenuation of scopolamine-induced amnesia may explain medicinal use of turmeric in Alzheimer's disease. | 2009-02 |
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| Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit cancer cell invasion through the down-regulation of MMPs and uPA. | 2009-02 |
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| Comparison of inhibitory potency of three different curcuminoid pigments on nitric oxide and tumor necrosis factor production of rat primary microglia induced by lipopolysaccharide. | 2008-12-05 |
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| Immune defects in Alzheimer's disease: new medications development. | 2008-12-03 |
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| Dimethoxycurcumin, a synthetic curcumin analogue with higher metabolic stability, inhibits NO production, inducible NO synthase expression and NF-kappaB activation in RAW264.7 macrophages activated with LPS. | 2008-09 |
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| Effect of pure curcumin, demethoxycurcumin, and bisdemethoxycurcumin on WT1 gene expression in leukemic cell lines. | 2008-09 |
|
| Comparison of suppressive effects of demethoxycurcumin and bisdemethoxycurcumin on expressions of inflammatory mediators in vitro and in vivo. | 2008-04 |
|
| Regulation of heme oxygenase-1 expression by demethoxy curcuminoids through Nrf2 by a PI3-kinase/Akt-mediated pathway in mouse beta-cells. | 2007-09 |
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| Curcuminoids purified from turmeric powder modulate the function of human multidrug resistance protein 1 (ABCC1). | 2006-02 |
|
| Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds. | 2005-06-15 |
|
| Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice. | 2005-02-23 |
|
| Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. | 1997-09-12 |
Patents
Sample Use Guides
Mice were treated with Bisdemethoxycurcumin as a dose of either 1 or 5 g/kg diet for 15 weeks.
Route of Administration:
Oral
NCI-H460 cells at a density of 5Ч105 cells/ml were maintained on 12-well plates with RPMI-1640 medium for 24 h and then incubated with or without 35 μM of Bisdemethoxycurcumin for 24 h. At the end of incubation, cells were collected from each treatment and total RNA was extracted by using the Qiagen RNeasy Mini Kit (Qiagen, Inc, Valencia, CA, USA)
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:06:11 GMT 2025
by
admin
on
Mon Mar 31 18:06:11 GMT 2025
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| Record UNII |
2EFO1BP34R
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| Record Status |
Validated (UNII)
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| Record Version |
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3710 (Number of products:81)
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Curcumin III
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