• Journal of Society of Preventive Korean Medicine
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• v.12 no.3
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• pp.67-80
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• 2008

The pathobiologic process of arterial stenosis following balloon angioplasty continues to be an enigmatic problem in clinical settings. This study investigates the ability of demethoxycurcumin, a curcuminoid isolated from Radix Curcumae, to attenuate balloon injury-induced neointima(NI) formation in the rat carotid artery. It was found that demethoxycurcumin induced inducible heme oxygenase(HO-1) expression and inhibited dose-dependently cellular proliferation in rat vascular smooth muscle cells. Perivascular application of demethoxycurcumin immediately following injury significantly reduced NI area and NI thickness 2 weeks post-injury. Interestingly, treatment with tin-protoporphyrin IX, a HO inhibitor, reversed the effects of demethoxycurcumin on NI formation. These results implicate demethoxycurcumin as a potent new therapeutic agent that is capable of reducing post-angioplasty arterial stenosis through induction of the HO-1 expression.

• Korean Journal of Pharmacognosy
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• v.38 no.2 s.149
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• pp.139-147
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• 2007

The aim of this study was to investigate the protective activity of curcumin, demethoxycurcumin and bisdemethoxycurcumin, isolated from Curcuma longa Linne, on hepatocyte injury induced by carbon tetrachloride (CCl$_4$,10 mM), t-butyl hydroperoxide (TBH, 0.5 mM) and D-galactosamine (GaIN,30 mM). Primary cultures of rat hepatocyte (18 h culture) were treated with CCl$_4$, TBH or GaIN and various concentrations (0.1, 1, 10 and 100 ${\mu}$M) of curcumin, demethoxycurcumin and bisdemethoxycurcumin CCl$_4$ significantly increased the levels of lactate dehydrogenase (LDH), alanine aminotransferase (ALT) and aspartate aminotransferase (AST). The increases in LDH, ALT and AST levels were inhibited by curcumin. Demethoxycurcumin and bisdemethoxycurcumin decreased the levels of AST. Curcumin inhibited the increases in ALT and AST levels induced by TBH. The increased levels of LDH, ALT and AST induced by TBH were inhibited by bisdemethoxycurcumin. GaIN markedly increased the levels of LDH, ALT and AST. These increases were significantly inhibited by bisdemethoxycurcumin. The increase in AST level was inhibited by curcumin. These results suggest that curcumin and bisdemethoxycurcumin have potent hepatoprotective activities.

• Journal of Korean Medicine Rehabilitation
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• v.20 no.2
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• pp.51-61
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• 2010

Objectives : The purpose of this study was to investigate antioxidant effects of curcumin from Curcumae Longae Radix. Methods : Using HepG2 Iiver-like cells, the antioxidant effects of curcumin, one of main components from Curcumae Longae Radix, and its analogues have been evaluated by measuring their effects on cytotoxicity induced by $H_2O_2$. Results : The pre-incubation for 6 hours with curcumin, bis-demethoxycurcumin, or dimethoxycurcumin protected HepG2 cells from $H_2O_2$-induced toxicity in a dose-dependent manner. However, tetrahydrocurcumin, one of curcumin metabolites, did not protect HepG2 cells from $H_2O_2$-induced toxicity. Interestingly, curcumin, bis-demethoxycurcumin, and dimethoxycurcumin were increased in the protein levels of heme oxygenase-1(HO-1) at concentrations that were also effective in cellular protection. In contrast, tetrahydrocurcumin did not induce HO-1 expression. Tin protoporphyrin-IX, an inhibitor of HO-1 activity, significantly abolished cytoprotection afforded by curcumin, bis-demethoxycurcumin and dimethoxycurcumin. Conclusions : These results demonstrate that curcumin, bis-demethoxycurcumin, and dimethoxycurcumin with two conjugated doble bonds on their structures may reduce $H_2O_2$-induced oxidative stress through HO-1 expression. HO-1 induction may be one of antioxidant pathways by which curcumin protects from oxidative stress-induced cytotoxicity.

• Journal of Society of Preventive Korean Medicine
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• v.11 no.1
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• pp.1-8
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• 2007

Curcumin and its analogues(Tetrahydrocurcumin THC, demethoxycurcumin ; BDMC and dimethoxycurcumin DiMC) were compared for their ability to inhibit the growth of human leukemia HL-60 cells. The growth of HL-60 cells was inhibited by curcumin, DeMC and DiMC, but not by THC lacking ${\alpha},{\beta}-unsaturated$ carbonyl groups thus suggesting that ${\alpha},{\beta}-unsaturated$ carbonyl groups are crucial for antiproliferative activity. The order of antiproliferative activity was DiMC, curcumin and BDMC indicating that the number of methoxy groups on the aromatic rings of the active compounds plays an important role in enhancing anti-proliferating activity. In comparison with cellular uptake of the active compounds, uptake capacity was found to be highest with DiMC, followed by curcumin and BDMC. Therefore, it is most likely that the differential antiproliferative activities of DiMC, curcumin and BDMC are associated with their capacities of cellular uptake resulting in building up of enough concentration inside the cells.

• Journal of Applied Biological Chemistry
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• v.61 no.2
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• pp.187-190
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• 2018

Two curcumin derivatives, demethoxycurcumin (DMC) and bisdemethoxycurcumin (BDMC), isolated from Curcuma longa were analyzed for their inhibitory activities against two isoforms of monoamine oxidase (MAO), which is involved in the catalysis of neurotransmitting monoamines. In the study, DMC and BDMC potently inhibited human MAO-B, with $IC_{50}$ values of 2.45 and $2.59{\mu}M$, respectively, and both compounds showed effective inhibitory activities against human MAO-A, with $IC_{50}$ values of 3.24 and $3.09{\mu}M$, respectively. The inhibitory activities of the two compounds were higher than those of curcumin. The removal of the methoxy or dimethoxy groups in curcumin might increase the inhibitory activities against human MAO-A and MAO-B. The inhibited activities were recovered to almost the values of the reversible references in the dialysis experiments with DMC and BDMC. DMC and BDMC showed competitive inhibition for MAO-A and MAO-B, respectively, with $K_i$ values of 0.91 and $0.80{\mu}M$, respectively. These results suggest that the two curcumin derivatives may be useful or lead compounds in the treatment of related disorders as potent reversible MAO inhibitors.

• Journal of Applied Biological Chemistry
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• v.56 no.3
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• pp.137-139
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• 2013

Free radical scavengers in the bisdemethoxycurcumin (BDMC), demethoxycurcumin (DMC) and curcumin of turmeric (Curcuma longa) were screened, identified, quantified and isolation using coupled off-line-2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) and on-line screening high-performance liquid chromatography (HPLC)-ABTS assay. There was a very small margin of error between the off-line-ABTS method and the on-line screening HPLC-ABTS method.

• International Journal of Oral Biology
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• v.46 no.1
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• pp.23-29
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• 2021

Demethoxycurcumin (DMC), which is a curcuminoid found in turmeric, has anti-proliferative effects on cancer cells. However, the effect of DMC on osteosarcoma has not been established. The aim of this study was to examine the effects of DMC on cell growth and apoptosis induction in MG-63 human osteosarcoma cells. This study was investigated using 3-[4, 5-dimethylthiazol-2-yl]-2, 5 diphenyl tetrazolium bromid assay, Live/Dead cell assay, 4', 6-diamidino-2-phenylindole staining, and immunoblotting in MG-63 cells. DMC induced MG-63 cell death in a dose-dependent manner, with an estimated IC50 value of 54.4 µM. DMC treatment resulted in nuclear condensation in MG-63 cells. DMC-induced apoptosis in MG-63 cells was mediated by the expression of Fas and activation of caspase-8, caspase-3, and poly (ADP-ribose) polymerase. Immunoblotting results showed that Bcl-2 and Bcl-xL were downregulated, while Bax and Bad were upregulated by DMC in MG-63 cells. These results indicated that DMC inhibits cell proliferation and induces apoptotic cell death in MG-63 human osteosarcoma cells via the death receptor-mediated extrinsic apoptotic pathway and mitochondria-mediated intrinsic apoptotic pathway.

• Journal of Pharmacopuncture
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• v.17 no.4
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• pp.36-49
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• 2014

Objectives: Quercetin and curcuminoids are important bioactive compounds found in many herbs. Previously reported high performance liquid chromatography ultraviolet (HPLC-UV) methods for the detection of quercetin and curcuminoids have several disadvantages, including unsatisfactory separation times and lack of validation according the standard guidelines of the International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use. Methods: A rapid, specific, reversed phase, HPLC-UV method with an isocratic elution of acetonitrile and 2% v/v acetic acid (40% : 60% v/v) (pH 2.6) at a flow rate of 1.3 mL/minutes, a column temperature of $35^{\circ}C$, and ultraviolet (UV) detection at 370 nm was developed. The method was validated and applied to the quantification of different types of market available Chinese medicine extracts, pills and tablets. Results: The method allowed simultaneous determination of quercetin, bisdemethoxycurcumin, demethoxycurcumin and curcumin in the concentration ranges of $0.00488-200{\mu}g/mL$, $0.625-320{\mu}g/mL$, $0.07813-320{\mu}g/mL$ and $0.03906-320{\mu}g/mL$, respectively. The limits of detection and quantification, respectively, were 0.00488 and $0.03906{\mu}g/mL$ for quercetin, 0.62500 and $2.50000{\mu}g/mL$ for bisdemethoxycurcumin, 0.07813 and $0.31250{\mu}g/mL$ for demethoxycurcumin, and 0.03906 and $0.07813{\mu}g/mL$ for curcumin. The percent relative intra day standard deviation (% RSD) values were $0.432-0.806{\mu}g/mL$, $0.576-0.723{\mu}g/mL$, $0.635-0.752{\mu}g/mL$ and $0.655-0.732{\mu}g/mL$ for quercetin, bisdemethoxycurcumin, demethoxycurcumin and curcumin, respectively, and those for intra day precision were $0.323-0.968{\mu}g/mL$, $0.805-0.854{\mu}g/mL$, $0.078-0.844{\mu}g/mL$ and $0.275-0.829{\mu}g/mL$, respectively. The intra day accuracies were 99.589%-100.821%, 98.588%-101.084%, 9.289%-100.88%, and 98.292%-101.022% for quercetin, bisdemethoxycurcumin, demethoxycurcumin and curcumin, respectively, and the inter day accuracy were 99.665%-103.06%, 97.669%-103.513%, 99.569%-103.617%, and 97.929%-103.606%, respectively. Conclusion: The method was found to be simple, accurate and precise and is recommended for routine quality control analysis of commercial Chinese medicine products containing the flour flavonoids as their principle components in the extracts.

• Biomedical Science Letters
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• v.19 no.2
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• pp.147-152
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• 2013

17-${\beta}$-hydroxysteroid dehydrogenase type 1 ($17{\beta}$-HSD type 1) mediates the reaction of $17{\beta}$-estradiol (E2) production from estrone (E1). Inhibitory effects of curcuminoids on $17{\beta}$-HSD type 1 activity were investigated to find a lead compound for treating estrogen-dependent diseases including breast cancer. Among curcuminoids, demethoxycurcumin showed potent inhibitory effect ($IC_{50}=2.7{\mu}M$) on mouse $17{\beta}$-HSD type 1. Curcuminoids also displayed their inhibitory effects on the production of $17{\alpha}$-estradiol which is a carcinogenic metabolite produced by the enzyme. Bisdemethoxycurcumin ($IC_{50}=1.3{\mu}M$) showed potent inhibitory effect on the $17{\alpha}$-estradiol production by chicken $17{\beta}$-HSD type 1. Curcuminoids did not inhibit ERE transcriptional activity with and without E2. Taken together, curcuminoids can be used for treating and preventing E2-dependent diseases via inhibition on $17{\beta}$-HSD type 1 activity.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.50 no.spc1
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• pp.211-215
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• 2005

Three curcuminoids [curcumin (CUR), demethoxycurcumin(DEM), bisdemethoxycurcu in (BIS)] are major yellow pigments in turmleric (Curcuma longa L.) root. Contents of curcuminoids in turmeric roots collected from 6 locations were analyzed using, high performance liquid chromatography (HPLC) equipped with reversed-phase column, an UV-Vis detector at 420nm, and eluted with a mixture of acetonitrile: $0.1\%$ acetic acid in water (50 : 50, v/v) as mobile phase. The stability of curcuminoid pigments in $80\%$ methanol extract solution were investigated during storage in a freezer at $-20^{\circ}C$, room temperature in the dark, and light condition. Calibration curves for the determination of curcuminoids were made with significant linearity $(r^2=0.999**)$. Average content of total curcuminoids was 171.5 mg/g, with 91.6 mg/g of CUR, 56.9 mg/g of DEM, and 23.0 mg/g of BIS. Amount of curcuminoids during storage in a freezer was almost not changed while those in room temperature wert reduced and rapid degradation appeared after 60 days. Within 90 days, about $50\%$ curcuminoid decreased in the dark and about $70\%$ in the light condition, indicating the decomposition of curcuminoid pigments followed under light and heat.