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PubMed2005

Chemopreventive properties of curcumin.

Inhibition of defined molecular steps of tumorigenesis by natural nontoxic compounds may be an efficient means to tackle the population cancer burden. Extensive research has addressed the chemotherapeutic potential of curcumin (diferuloylmethane), a relatively nontoxic plant-derived polyphenol. This review considers the following properties of curcumin: anticancer effects in animal model systems; metabolism; biological structure and pharmacokinetics; biological properties implicated in chemoprevention; antioxidant properties; influences upon Phase I and II carcinogen-metabolizing enzymes; signal transduction properties and the neoplastic phenotype; apoptosis evasion, cell proliferation, de-differentiation, migration and invasion and clinical studies. This review will summarize the unique properties of curcumin that may be exploited for successful clinical cancer prevention.

Antineoplastic Agents↗

PubMed2005

Effects of dietary quillaja saponin and curcumin on the performance and immune status of weaned piglets.

The objective of this study was to determine whether dietary quillaja saponin and curcumin (extract of turmeric) can modify piglet immune status and performance immediately after weaning. Piglets (n = 192) were weaned at 29 +/- 0.1 d and allocated to treatment (six replicates of eight pig per treatment) accounting for weight, litter, and gender, using a 2 x 2 factorial arrangement. Factors were diets with or without (as-fed basis) quillaja saponin (750 mg/kg during wk 1, 300 mg/kg during wk 2 to 3) and with or without dietary curcumin (200 mg/kg). Diets were fed ad libitum for 20 d after weaning. Feed intake was measured daily. Piglets were weighed at weaning, d 7, 14, and 20 after weaning. On each of d 6 and 20 after weaning, eight pigs per treatment were sacrificed for blood and tissue collection. Treatment had no effect on piglet growth. The ADFI and G:F were similar for all treatments between d 0 and 14 of the trial. Between d 15 and 20, ADFI and G:F were lower in quillaja-supplemented piglets (ADFI = 621 vs. 572 g/d; G:F = 0.75 vs. 0.85; P < 0.05). Serum immunoglobulin (Ig) G, IgA, interferon-gamma, and C-reactive protein (CRP) did not differ among treatments on d 6 after weaning. On d 20, IgG and CRP were greater (P < 0.05) in saponin-supplemented pigs (IgG = 17.5 vs. 11.4 mg/mL; CRP = 26.98 vs. 12.5 mg/mL). Small intestine villus and crypt measurements did not differ among treatments on either d 6 or 20. Saponin supplementation during the postweaning period seemed to potentiate an immune response in the weaned piglet but had a detrimental effect on the utilization of feed. Dietary curcumin had no influence on any measured aspect of pig performance or immune status.

Animal Feed↗

PubMed1978

The metabolism and excretion of curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) in the rat.

Curcumin labelled with deuterium and tritium was prepared. Oral and intraperitoneal doses of [3H]curcumin led to the faecal excretion of most of the radioactivity. 2. Intravenous and intraperitoneal doses of [3H]curcumin were well excreted in the bile of cannulated rats. 3. The major biliary metabolites were glucuronides of tetrahydrocurcumin and hexahydrocurcumin. A minor biliary metabolite was dihydroferulic acid together with traces of ferulic acid. Metabolites were identified using chemical ionization mass spectrometry.

Animals↗

PubMed1976

The influence of turmeric and curcumin on cholesterol concentration of eggs and tissues.

An experiment was conducted in order to study the hypocholesteremic effect of tumeric and its coloring principle namely curcumin both in the presence and absence of dietary cholesterol. Laying hens were used as the experimental animals and they were fed the experimental diets for a duration of 8 weeks. The results of the experiment showed that tumeric or various levels of curcumin had no adverse effect on egg production, egg weight and feed to egg ratio. Moreover tumeric or various levels of curcumin both in the presence and absence of dietary cholesterol did not reduce the fat or cholesterol levels of plasma, liver or the egg yolk. An interesting finding from this experiment was that the egg yolk cholesterol levels of cholesterol fed groups sharply increased at the beginning of the experiment, and thereafter they gradually decreased and tended to approach the normal levels at the termination of the experiment. The possible reasons for variation in egg yolk cholesterol levels of cholesterol-fed groups with time is discussed.

Animals↗

PubMed1998

Protective effect of curcumin, ellagic acid and bixin on radiation induced genotoxicity.

Induction of micronuclei and chromosomal aberrations produced by whole body exposure of r-radiation (1.5-3.0 Gy) in mice was found to be significantly inhibited by oral administration of natural antioxidants, curcumin (400 micro moles), ellagic acid (200 micro moles) and bixin (200 micro moles) per kilogram body weight. These antioxidants induced inhibition of micronucleated polychromatic and normochromatic erythrocytes, was comparable with alpha-tocopherol (200 micro moles) administration. Curcumin and ellagic acid were also found to significantly reduce the number of bone marrow cells with chromosomal aberrations and chromosomal fragments as effectively as alpha-tocopherol. Moreover, administration of antioxidants inhibited the DNA strand breaks produced in rat lymphocytes upon radiation as seen from the DNA unwinding studies. These results indicated that antioxidant curcumin, ellagic acid and bixin provide protection against chromosome damage produced by radiation.

Animals↗

PubMed2003

Structure of curcumin in complex with lipoxygenase and its significance in cancer.

Scientific research provides documented evidence that fatty acid metabolites have profound impact on carcinogenesis. Intervention into dioxygenase pathways might therefore effect development, metastasis and progression of many types of cancers. This work delivers the first 3D structural data and explains how curcumin interacts with the fatty acid metabolizing enzyme, soybean lipoxygenase. Curcumin binds to lipoxygenase in a non-competitive manner. Trapped in that complex, it undergoes photodegradation in the X-rays, but utilizes enzyme catalytic ability to form the peroxy complex Enz-Fe-O-O-R as 4-hydroperoxy-2-methoxy-phenol, that later transforms into 2-methoxycyclohexa-2,5-diene-1,4-dione. Our observations about this radiation and time-dependent inhibition add new information to the role that curcumin might play in cancer prevention and treatment.

Animals↗

PubMedDate not supplied

Curcumin and resveratrol induce apoptosis and nuclear translocation and activation of p53 in human neuroblastoma.

BACKGROUND: Neuroblastoma (NB) is an aggressive childhood cancer of the peripheral nervous system arising from neural crest sympathoadrenal progenitor cells. Despite current rigorous treatment protocols, prognosis for high stage NB patients is poor and so there remains a need for more effective, less cytotoxic treatments. Curcumin and resveratrol possess anti-tumor properties in adult cancer models and negligible toxicity in normal cells, but little is known about the effect of these agents on pediatric cancers. MATERIALS AND METHODS: Stage 4 MYCN-amplified NB cell lines, with wild-type or mutant p53, were treated with curcumin and resveratrol and analyzed for effects on proliferation, cell cycle, induction of apoptosis and p53 function. RESULTS: Treatment induced a dose- and time-dependent decrease in cell viability, cell cycle arrest and induction of apoptosis. Treatment transiently up-regulated p53 expression and induced nuclear translocation of p53, followed by induction of p21(WAF-1/CIP-1) and Bax expression. CONCLUSION: Observations suggest that the cytotoxicity, cell cycle arrest and apoptosis induced by curcumin and resveratrol in NB cells may be mediated via functionally activated p53 and merit further study.

Antineoplastic Agents↗

PubMed1999

Curcumin damages DNA in human gastric mucosa cells and lymphocytes.

The naturally occurring pigment curcumin, a major component of the spice turmeric, is reported to be a potent inhibitor of the initiation and promotion of many cancers. Due to its presence in the diet, one of its primary targets is the human gastric mucosa (GM) cells. Using the sensitive single cell electrophoresis method (comet assay), we found that curcumin at of 15, 25, and 50 microM caused DNA damage in GM cells and human peripheral blood lymphocytes. There was no difference between the extent of the damage in both types of cells. Damaged cells were able to recover within a period of 120 minutes. Our results indicate that curcumin may play a dual role in carcinogenesis.

Antineoplastic Agents↗

PubMed2004

Interactive effects of saffron with garlic and curcumin against cyclophosphamide induced genotoxicity in mice.

Saffron is a well-known spice and food colorant commonly consumed in different parts of the world. Recently, much attention has been focused on the biological and medicinal properties of saffron. In the present study the interactive effects of saffron with two commonly consumed dietary agents, garlic and curcumin was evaluated for anti-genotoxic effects against cyclophosphamide (CPH) in the mouse bone marrow micronucleus test. Experimental animals were orally pretreated with saffron (100 mg/kg body weight), garlic (250 mg/kg body weight) and curcumin (10 mg/kg body weight), either alone or in combination for five consecutive days, 2h prior to the administration of CPH. Maximum reduction in the frequencies of micronucleated polychromatic erythrocytes (Mn PCEs) induced by CPH was observed when all the three test compounds were administered together. Furthermore, the protective effects were more pronounced in the garlic-administered groups compared to curcumin and/or saffron administered groups.

Administration, Oral↗

PubMed2004

Comparison of the anti-proliferation and apoptosis-induction activities of sulindac, celecoxib, curcumin, and nifedipine in mismatch repair-deficient cell lines.

BACKGROUND AND PURPOSE: The adenomatous polyposis coli (APC) and mismatch repair (MMR) pathways are both involved in the tumorigenesis of hereditary colorectal cancers. Chemoprevention focuses on the APC pathway in the absence of information concerning MMR targets. This study compared the anticancer effects of sulindac, celecoxib, curcumin, and nifedipine in MMR-deficient cell lines, in order to determine the most appropriate chemopreventive agent for long-term use in patients with hereditary colorectal cancer. METHODS: Five human colorectal cell lines (SW480, HCT116, LoVo, SW48, and HCT15) and an endometrial cancer cell line (HEC-1-A) were used for susceptibility testing. Tests included assays for growth inhibition, cell-cycle arrest, and apoptosis. RESULTS: Sulindac, celecoxib, curcumin, and nifedipine all displayed dose- and time-dependent anti-proliferation activities. Celecoxib was the most effective anti-proliferative agent, and increased the G0/G1 phase proportion in the cell cycle after treatment more significantly than the other agents in all cell lines. Curcumin displayed a more potent apoptosis-inducing activity than the other agents in treated cells. CONCLUSIONS: The tested drugs were effective against colorectal and endometrial cancer cell lines. Celecoxib is more potent with fewer side effects than sulindac. Nifedipine's observed chemopreventive efficacy may complement its known therapeutic application in patients with hypertension.

Antineoplastic Agents↗

PubMed2004

[Studies on photoluminescence characteristics of curcumin in acrylamide polymer].

A photoluminescence polymer was prepared using acrylamide as a monomer, a large excess of ethyleneglycol dimethacrylate as the cross-linking agent, and curcumin as a fluorescence additive. The polymer was ground into powder and screened in order to get even powder, whose diameter was from 40 to 75 microm. The emission spectra of curcumin in solid powder polymer show a strong blue shift compared with that of curcumin in C2H5OH solution. Meanwhile, rhodamine 6G, tetraiodofluorescein and phloxin have the same phenomenon of blue shift. Based on these facts, we speculate that the mechanism is probably singlemolecular luminescence because of the limit effect in three dimension space of the polymer. The molecule fluorescence peak was also depending on its environment because the surrounding electron field affected the molecule luminescence in polymer.

Acrylamide↗

PubMed2005

Antiangiogenic activity of curcumin in hepatocellular carcinoma cells implanted nude mice.

Antiangiogenic activity of curcumin on the tumor neogenesis was investigated by evaluating the density of neocapillaries induced by Hepatocellular carcinoma cells (HepG2) in mice, using intravital fluorescence videomicroscopy. Male BALB/c nude mice (20-25 g) were used, and a dorsal skin-fold chamber was implanted. HepG2 (30 microl of 2 x 10(6) cells) were inoculated on the upper surface of the skin within the chamber. The mice were divided into two groups as follows. Dimethyl sulfoxide solution (0.1%) was fed (HepG2 group, n=5) or curcumin solution (3000 mg/kg bw) was fed oral daily (HepG2-Cur group, n=5), one day after the inoculation of HepG. On days 7 and 14 post-tumor-inoculation, the tumor microvasculature was visualized by injecting 0.1 ml of 0.5% rhodamine B isothiocyanate-labeled dextran intravenously, and observed under an intravital fluorescence videomicroscope. Based on the recorded videoimage, the tumor neocapillary density and microvasculature were evaluated using a digital image analysis and correlated with the tumor area. The image analysis demonstrated that in the HepG2-group the neocapillary densities were significantly increased on day 7, and day 14, compared to the aged-matched Sham-group (P<0.05). In the HepG2-Cur group, the increase of tumor neocapillary density was attenuated significantly. It was suggested that high dose of curcumin might be an effective anti-angiogenic drug in the treatment against tumor.

Angiogenesis Inhibitors↗

PubMed2005

[Preventive role of curcumin in lung cancer].

Carcinogens from cigarette smoke form the link between nicotine addiction and lung cancer, which is the leading cause of cancer-related mortality in the world. One of the most frequently studied chemopreventive agents is a curcumin, a natural compound extracted from turmeric that inhibits cell proliferation and induces apoptosis in human leukaemia, prostate cancer, and non-small cell lung cancer. Curcumin (diferuoylmethane) is a major yellow pigment in turmeric (Curcuma longa) and is widely used as a spice. Curcumin exhibits a variety of pharmacological effects, and has been reported to have anti-inflammatory and anti-tumor activities.

Curcumin↗

PubMed1989

[Spectrophotometric determination of boric acid by the curcumin method].

We have contrived an improved curcumin method for a spectrophotometric determination of the boric acid content, suitable for use on biologic materials to determine cases of poisoning. The use of this method enables detection of boric acid from a level of 10 micrograms/ml up to 5 mg/ml. The steps of this measurement method follow. Initially, boric acid was extracted by using a modification of Agazzi's method, i.e., to 1 ml of the sample solution, 0.2 ml of a 50% solution of sulfuric acid is added, along with 4 ml of 10 v/v% 2-ethyl-1,3-hexanediol/chloroform (an EHD solution). This mixture was then shaken for 5 min and then centrifuged for 10 min at 3,000 rpm. The extract of this chloroform phase was dehydrated with anhydrous sodium sulfate and used for the coloring reaction sample. The colorimetry procedure for determining the boric acid content follows. Fifty microliters of the extract solution was placed into a dry tube, to which 0.5 ml of a 0.3% curcumin/acetic acid solution and 50 microliters concentrated sulfuric acid were added, and the contents mixed thoroughly. The reaction mixture was then allowed to stand for 30 min at room temperature. (Rosocyanin is formed by the reaction of boric acid and protonated curcumin). Next, ethanol (3-138 ml) was added to the reaction mixture to decompose the excess protonated curcumin. Then, the absorbancy of the resulting solution was measured at 550 nm against a blank test solution. Ethanol was added to enable the measurement of the absorbancy (ethanol amounts tested were 3, 6, 12, 24, and 138 ml).(ABSTRACT TRUNCATED AT 250 WORDS)

Boric Acids↗

PubMed1999

Free radical scavenging ability and antioxidant efficiency of curcumin and its substituted analogue.

Free radical reactions of curcumin and its ethoxy substituted derivative (C1) 1,7-bis-(4-hydroxy-3-ethoxy phenyl)-1,6-heptadiene-3,5-dione have been studied using a pulse radiolysis technique in homogeneous aqueous-organic solutions like acetonitrile-water and isopropanol-water mixtures, as well as in neutral TX-100 and cationic CTAB micellar solutions. The phenoxyl radicals of curcumin or C1 were generated by one-electron transfer to several oxidants like N(3)(.), Br(2)(-.), CCl(3)O(2)(.), glutathione radicals which exhibit absorption from a 300-600-nm wavelength region with the maximum at 490-500 nm. Other important properties of the phenoxyl radicals such as extinction coefficient, radical lifetime and their formation and decay rate constants were also determined in these systems. The antioxidant property of curcumin and C1 were estimated in terms of their ability to inhibit the lipid peroxidation in liposomes and also in terms of trolox equivalent antioxidant capacity (TEAC). The results were compared with alpha-tocopherol.

Journal Article↗

PubMed2000

Changes in the prostaglandin levels in alcohol toxicity: effect of curcumin and N-acetylcysteine.

The present study was undertaken to evaluate the potential role of curcumin, the antioxidant principal from Curcuma longa Linn., and the sulphur-containing amino acid N-acetylcysteine against ethanol-induced changes in the levels of prostanoids. Biochemical assessment of liver damage was done by measuring the activities of serum enzymes (i.e., aspartate transaminase and alkaline phosphatase), which were significantly increased in rats fed ethanol, whereas the elevated levels of these enzymes were decreased after curcumin and N-acetylcysteine treatment to rats fed ethanol. We observed a significant increase in the levels of prostaglandins E(1), E(2), F(2alpha), and D(2) in liver, kidney, and brain. Administration of curcumin and N-acetylcysteine was shown to decrease the level of these prostanoids in the tissue studied.

Journal Article↗

PubMed2005

Synthesis and antitumor activity of some curcumin analogs.

In this study, four new curcurmin analogs (compounds 1, 2, 17 and 18) were synthesized. 17 [3,5-bis(4-hydroxy-3-methoxy-5-methylcinnamyl)N-methylpiperidone] showed high activity with GI50, TGI, and LC50 MG-MID values of 21.3, 70.7, and 97.7 microM, respectively. 18 [3,5-bis(4-hydroxy-3-methoxy-5-methylcinnamyl)-N-ethylpiperidone] showed the highest activity in this study with GI50, TGI, LC50 MG-MID values of 4.4, 33.8, 89.1 microM, respectively. 18 is even more active than curcumin with GI50, TGI, LC50 MG-MID values of 38.4, 35.6, 66.0 microM; respectively. 8 showed moderate selectivity towards Leukemia cell line-subpanel with a ratio of 5.6 (curcumin ratio: 1.2 for the same subpanel). The in vitro anti-tumor screening reveals that the results go hand in hand with the in vitro free radical scavenging effects. The antioxidant effect of these compounds depends mainly on the stabilization of the formed phenoxy free radical for which the p-hydroxy phenyl moiety is essential. o-substitution by electron-donating groups like the o-methoxy group (and to a even higher degree by the ethoxy group) increases the stability of phenoxy free radical, hence increasing both free scavenging and anti-tumor effects. Increasing the alkyl group chain on the N in the series of substituted N-alkyl piperidones as well as the extension of conjugation, increases the stabilization of phenoxy free radical and thereby the activity towards both free radical scavenging and anti-tumor effects. This may be attributed to an increased positive inductive effect and/or increased lipophilicity of the new compounds, a fact which is proven by the superior activities of compounds 17 and 18.

Antineoplastic Agents, Phytogenic↗

PubMed2006

Curcumin analogs as potent aldose reductase inhibitors.

In the present study, curcuminoids isolated from curcuma longa were demonstrated to possess inhibitory activities on bovine lens aldose reductase. In order to find more potent aldose reductase inhibitor, curcumin analogs were synthesized and evaluated for their ability to inhibit bovine lens aldose reductase enzyme. The results indicated that the compounds with tetrahydroxyl groups, 2,6-bis(3,4-dihydroxybenzylidene)cyclohexanone (A(2)), 2,5-bis(3,4-dihydroxybenzylidene)cyclopentanone (B(2)), 1,5-bis(3,4-dihydroxyphenyl)-1,4-pentadiene-3-one (C(2)), and 3,5-bis(3,4-dihydroxybenzylidene)-4-piperidone (D(2)) showed remarkably potent inhibitory effects on aldose reductase with IC(50) of 2.9 microM, 2.6 microM, 3.4 microM, and 4.9 microM, respectively. The structure-activity relationship revealed that the curcumin analogs with ortho-dihydroxyl groups could form a more tight affinity with aldose reductase to exert more potential inhibitory activities.

Aldehyde Reductase↗