curcumin and curdione

Turmeric, a dried powder derived from the rhizome of Curcuma longa, has been used for centuries in certain parts of the world and has been linked to numerous biological activities including antioxidant, anti-inflammatory, anticancer, antigrowth, anti-arthritic, anti-atherosclerotic, antidepressant, anti-aging, antidiabetic, antimicrobial, wound healing, and memory-enhancing activities. One component of turmeric is curcumin, which has been extensively studied, as indicated by more than 5600 citations, most of which have appeared within the past decade. Recent research has identified numerous chemical entities from turmeric other than curcumin. It is unclear whether all of the activities ascribed to turmeric are due to curcumin or whether other compounds in turmeric can manifest these activities uniquely, additively, or synergistically with curcumin. However, studies have indicated that turmeric oil, present in turmeric, can enhance the bioavailability of curcumin. Studies over the past decade have indicated that curcumin-free turmeric (CFT) components possess numerous biological activities including anti-inflammatory, anticancer, and antidiabetic activities. Elemene derived from turmeric is approved in China for the treatment of cancer. The current review focuses on the anticancer and anti-inflammatory activities exhibited by CFT and by some individual components of turmeric, including turmerin, turmerone, elemene, furanodiene, curdione, bisacurone, cyclocurcumin, calebin A, and germacrone.

Topics: Animals; Anti-Inflammatory Agents; Antineoplastic Agents; Antioxidants; Clinical Trials as Topic; Curcuma; Curcumin; Cyclohexanols; Disease Models, Animal; Furans; Heterocyclic Compounds, 2-Ring; Humans; Hypoglycemic Agents; Inflammation; Neoplasms; Sesquiterpenes; Sesquiterpenes, Germacrane

Phytophthora capsici is a plant oomycete pathogen, which causes many devastating diseases on a broad range of hosts. Zedoary turmeric oil (ZTO) is a kind of natural plant essential oil that has been widely used in pharmaceutical applications. However, the antifungal activity of ZTO against phytopathogens remains unknown. In this study, we found ZTO could inhibit P. capsici growth and development in vitro and in detached cucumber and Nicotiana benthamiana leaves. Besides, ZTO treatment resulted in severe damage to the cell membrane of P. capsici, leading to the leakage of intracellular contents. ZTO also induced a significant increase in relative conductivity, malondialdehyde concentration and glycerol content. Furthermore, we identified 50 volatile organic compounds from ZTO, and uncovered Curcumol, β-elemene, curdione and curcumenol with strong inhibitory activities against mycelial growth of P. capsici. Overall, our results not only shed new light on the antifungal mechanism of ZTO, but also imply a promising alternative for the control of phytophthora blight caused by P. capsici.

Topics: Antifungal Agents; Cell Membrane; Curcuma; Oils, Volatile; Phytophthora; Plant Extracts; Plant Oils; Sesquiterpenes; Sesquiterpenes, Germacrane

Curdione, a sesquiterpene compound isolated from the essential oil of Curcuma aromatica Salisb. inhibits platelet aggregation, suggesting its significant anticoagulant and antithrombotic effects. However, the mechanisms have not been fully elucidated.. We hypothesized that curdione inhibits thrombin-induced platelet aggregation via regulating the AMP-activated protein kinase-vinculin/talin-integrin αIIbβ3 signaling pathway.. We performed in vitro assays to evaluate the effect of curdione on thrombin-induced expression levels of the AMPK signaling molecule and integrin αIIbβ3 signaling pathway components.. Platelet proteins were extracted from washed human platelets, and the effects of curdione on thrombin-induced platelet aggregation were evaluated. The expression levels of the AMPK signaling molecule and integrin αIIbβ3 signaling pathway-related proteins were examined using western blot and RT-PCR. The binding of vinculin and talin were studied using immunoprecipitation, double immunofluorescence staining and microscale thermophoresis.. Platelet aggregation analysis showed that 0.02 U/ml thrombin significantly induces platelet aggregation. Western blot and RT-PCR analysis revealed that AMPK inhibits the vinculin/talin-mediated integrin αIIbβ3 signaling pathway, and curdione downregulates the thrombin-induced expression of phosphorylated AMPK (P-AMPK) and P-integrin at both the protein and mRNA levels and downregulates vinculin and talin at the protein level. Furthermore, microscale thermophoresis experiments showed that curdione inhibits the binding of vinculin and talin. The results from the immunoprecipitation and double immunofluorescence staining were consistent with the results of the microscale thermophoresis experiments.. Curdione inhibits thrombin-induced platelet aggregation via regulating the AMP-activated protein kinase-vinculin/talin-integrin αIIbβ3 signaling pathway, which suggests its therapeutic potential in ethnomedicinal applications as an anti-platelet and anti-thrombotic compound to prevent thrombotic diseases.

Topics: AMP-Activated Protein Kinases; Curcuma; Drug Evaluation, Preclinical; Humans; Platelet Aggregation; Platelet Aggregation Inhibitors; Platelet Glycoprotein GPIIb-IIIa Complex; Sesquiterpenes, Germacrane; Signal Transduction; Talin; Thrombin; Vinculin

Topics: Curcuma; Glucose; Hep G2 Cells; Humans; Molecular Structure; Plant Tubers; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes

Rhizoma Curcumae, the dry rhizomes derived from Curcuma aromatica Salisb., are a classical Chinese medicinal herb used to activate blood circulation, remove blood stasis and alleviate pain. Our previous study proved that curdione, a sesquiterpene compound isolated from the essential oil of Curcuma aromatica Salisb. can inhibit platelet activation suggesting its significant anticoagulant and antithrombotic effects. However, the underlying mechanism of curdione mediated anti-platelet effect has not been fully elucidated. Platelet proteins extracted from washed human platelets, including normal group (treated with normal saline), thrombin group and curdione group were digested and analysed by nano ESI-LC-MS/MS. UniProt database and SIEVE software were employed to identify and reveal the differentially expressed proteins. Furthermore, possible mechanisms involved were explored by Ingenuity Pathway Analysis (IPA) Software and validated by western blot experiments. Twenty-two differentially expressed proteins between the normal and thrombin group were identified. Compared with the thrombin group, the curdione treatment was significantly down-regulated only 2 proteins (Talin1 and β1-tubulin). Bioinformatics analysis showed that Talin1 and β1-tubulin could be involved in the integrin signal pathway. The results of western blot analysis were consistent with that of the proteomics data. Vinculin, identified in IPA database was involved in the formation of cell cytoskeletal. The down-regulation of β1-tubulin facilitated the decrease in vinculin/Talin1. Curdione regulated the expression of vinculin and Talin1 by β1-tubulin affecting the integrin signalling pathway and eventually inhibiting platelet activation. The β1-tubulin may be a potential target of curdione, which attenuates thrombin-induced human platelet activation.

Topics: Blood Platelets; Curcuma; Down-Regulation; Humans; Oils, Volatile; Platelet Activation; Proteome; Rhizome; Sesquiterpenes, Germacrane; Signal Transduction; Talin; Thrombin; Tubulin; Vinculin

A simple, rapid and sensitive method was developed for the simultaneous quantification of curdione, furanodiene and germacrone in rabbit plasma using a LC-MS/MS analysis. The plasma sample preparation was a simple deproteinization by the addition of 3 vols of acetonitrile followed by centrifugation. The analytes and internal standard (IS) costunolide were separated on a Zorbax SB-C18 column (3.5 µm, 2.1 × 100 mm) with mobile phase of methanol-water (90:10, v/v) containing 0.1% formic acid at a flow rate of 0.3 mL/min with an operating temperature of 25°C. Detection was carried out by atmospheric pressure chemical ionization in positive ion selected reaction monitoring mode. Linear detection responses were obtained for the three test compounds ranging from 5 to 5000 ng/mL and the lower limits of quantitation were 5-10 ng/mL. The intra- and inter-day precisions (relative standard deviations) were within 9.4% for all analytes, while the deviation of assay accuracies was within ±10.0%. The average recoveries of analytes were >80.0%. All analytes were proved to be stable during all sample storage, preparation and analytical procedures. The method was successfully applied to the pharmacokinetic study of the three compounds after vaginal drug delivery of Baofukang suppository to rabbit.

Topics: Animals; Chromatography, High Pressure Liquid; Curcuma; Drugs, Chinese Herbal; Furans; Heterocyclic Compounds, 2-Ring; Rabbits; Sesquiterpenes, Germacrane; Tandem Mass Spectrometry

The sesquiterpenoid curdione is one of the main bioactive components in the essential oil of Rhizoma Curcumae (Curcuma wenyujin, Curcuma phaeocaulis, and Curcuma kwangsiensis), which has been clinically used for the treatment of cancer in mainland China. Recently it was reported that natural curdione could be hydroxylated by Aspergillus niger and transferred to its corresponding curcumalactones under acidic conditions. Based on this study, the development of a sesquiterpenoid library through the "mirror-image" manipulation of bioactive (non)natural curdione scaffolds by chemical and biological approaches is presented herein. A. niger induced the hydroxylation of two pairs of curdione enantiomers, yielding the corresponding mirror-image hydroxylated curdiones. Simultaneously, the acid-mediated intramolecular "ene" rearrangements of these curdiones and hydroxylated curdione enantiomers yielded the corresponding mirror-image curcumalactones and hydroxylated curcumalactones. Among the 16 pairs of enantiomers obtained in this study, 23 compounds are new sesquiterpenoids. These curdione and curcumalactone derivatives are of particular interest, as they have the potential to be used as lead compounds and scaffolds in drug discovery.

Topics: Aspergillus niger; China; Combinatorial Chemistry Techniques; Curcuma; Drug Discovery; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oils, Volatile; Rhizome; Sesquiterpenes; Sesquiterpenes, Germacrane; Stereoisomerism

This study aims to develop a method for determination of beta-elemene, curcumol, germacrone and neocurdione in the volatile oil of Curcuma phaeocaulis, and to provide the basis of the quality control method for the volatile oil of C. phaeocaulis and the related preparations. Based on GC-MS, the 4 main compounds were simultaneously determined, with the internal standard n-tridecane. The Agilent 19091S-433 column (0.25 microm x 250 microm x 30 m) was adopted at the temperature of 250 degrees C, the programmed temperature method (60 degrees C for 1 min, 5 degrees C x min x to 110 degrees C for 5 min, 1 degrees C x min(-1) to 140 degrees C, 5 degrees C x min(-1) to 160 degrees C, 10 degrees C x min(-1) to 240 degrees C) was used. Helium gas was used as the carrier gas at a constant flow rat of 1 mL x min(-1), with an injection volume of 1 RL. Mass spectra were taken at 70 eV; the ion-source temperature was 200 degrees C. The relation time and character acteristic ions for each target compound were determined by full scan mode and SIM, and m/z 85.1, 93.1, 121.1, 107.1 and 180.1 were the detection ions of n-tridecane, beta-elemene, curcumol, germacrone and neocurdione. As a result, beta-elemene, curcumol, germacrone and neocurdione were all detected with good separation. They were all in a good linear relationship within each concentration scope. The average recovery rates were in the range of 98.2%-101%. So, the method can be used to control the quality of the volatile of C. phaeocaulis Val. and the preparations related.

Topics: Acetic Acid; Curcuma; Drugs, Chinese Herbal; Gas Chromatography-Mass Spectrometry; Oils, Volatile; Plant Oils; Sesquiterpenes; Sesquiterpenes, Germacrane

Curdione (1), a sesquiterpene with a germacrane skeleton from rhizomes of Curcuma wenyujin, has attracted attention due to its important pharmacological properties. Herein, we investigated the chemo-biotransformation of curdione (1) systematically using Aspergillus niger AS 3.739. Regio- and stereoselective hydroxylation of curdione with filamentous fungus A. niger AS 3.739 led to seven metabolites including four new compounds 3α-hydroxycurcumalactone, 2β-hydroxycurcumalactone, (10S)-9,10-dihydroxy-curcumalactone and (10R)-9,10-dihydroxy-curcumalactone. Their structures were determined by spectroscopic techniques including two-dimensional NMR and TOF-MS (Time of Flight Mass Spectrometry). Based upon the analysis of biological and chemical conversions of curdione, a tentative metabolic pathway via chemo-bio cascade reactions is proposed in A. niger system, which provides an insight into the corresponding metabolism of curdione in animal systems. In addition, experiments with selected monooxygenase inhibitors suggest that cytochrome P450 monooxygenase played a crucial role in the hydroxylation of curdione.

Topics: Animals; Aspergillus niger; Curcuma; Cytochrome P-450 Enzyme System; Nuclear Magnetic Resonance, Biomolecular; Sesquiterpenes; Sesquiterpenes, Germacrane; Stereoisomerism

A selective and sensitive liquid chromatography tandem mass spectrometry method was developed for the first time for the identification and quantification of curdione in rabbit plasma after vaginal drug administration and intravenous administration of zedoary turmeric oil (ZTO) solution (10 mg/kg). The analysis was performed on a triple-quadrupole tandem mass spectrometer with multiple reaction monitoring mode via electrospray ionization source in positive ionization mode. After mixing with internal standard diazepam, plasma samples were extracted with ethyl ether-acetic ether (1:1, v/v). Chromatographic separation was carried out on a C18 column with gradient elution using a mixture of water and acetonitrile (both containing 0.1% formic acid) as mobile phases. Linearity ranged over 1.06-106 and 10.6-530 ng/mL (r ≥ 0.995) with the lower limit of quantfication 1.06 ng/mL. The intra- and inter-day precision relative standard deviation values were <12% and the accuracy relative error was from -10.6 to -6.1% at all quality control sample levels. The method was applied to a study of the pharmacokinetics of curdione after vaginal drug administration and intravenous administration of ZTO.

Topics: Administration, Intravaginal; Animals; Chromatography, Liquid; Curcuma; Drug Stability; Female; Linear Models; Plant Extracts; Rabbits; Reproducibility of Results; Sensitivity and Specificity; Sesquiterpenes, Germacrane; Tandem Mass Spectrometry

An ultra-performance liquid chromatography-quadrupole time-of-flight/mass spectrometry (UPLC/QTOF/MS) method was established to determine the chemical components of curcuma rhizomes (Ezhu) and their pharmacokinetics. Chromatographic separation was performed by UPLC using a 1.8 µm column in order to obtain good resolution and increase the sensitivity of analysis. Accurate mass measurement within 5 ppm error for each ion produced in positive mode electrospray ionization and the subsequent QTOF product ions enabled 12 compounds to be identified. Several of the identified components, including β-elemene, curcumol, germacrone and curdione, are thought to be the biologically active ingredients. Quantitative pharmacokinetic analysis was also carried out by UPLC/QTOF/MS. Using 20(S)-protopanoxadiol as an internal standard, samples were prepared by protein precipitation with methanol. Chromatographic separation was performed on an Agilent Extend-C18 column (2.1 × 50 mm, 1.8 µm) with acetonitrile (0.1% formic acid)-water (0.1% formic acid) for gradient elution. Curdione calibration plots were linear over the range of 0.1-12.2 µg/mL for curdione in plasma with the lower quantification limit being 6.5 ng/mL, and the recovery from plasma was about 105.2%. The RSD for both intra- and inter-day precision was <9.9%.

Topics: Animals; Chromatography, High Pressure Liquid; Curcuma; Male; Plant Extracts; Rats; Rats, Sprague-Dawley; Rhizome; Sesquiterpenes, Germacrane; Tandem Mass Spectrometry

To analyze the essential oil from the rhizome of Curcuma aromatica of different growth periods, and to provide the scientific reference for reasonable cultivation and quality control of this plant.. The essential oil was extracted by hydrodistillation and analyzed with GC-MS. The relative contents were determined with area normalization method.. The main volatile constituents in the rhizome of Curcuma aromatica were basically the same. Among these volatile constituents, curdione was the major. The relative content of curdione was 16.35% in the rhizome of wild plant in Hengxian county, and 15.81% in the rhizome of one-year-old plant in Mingyang farm, Nanning city. The relative content of eucalyptol in the 2-year-old cultivated rhizome in Hengxian county was 15.40%, and 14.59% in the rhizome of wild plant in Hengxian county. beta-Elemene, beta-caryophyllene,eugenol and germacrone were also the main constituents in the rhizome essential oil.. Volatile constituents in the rhizome of Curcuma aromatica are similar to each other,but the relative content of each component is different. This result can provide the scientific foundation for the cultivation of Curcuma aromatica.

Topics: Curcuma; Cyclohexanols; Eucalyptol; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Plant Oils; Quality Control; Rhizome; Sesquiterpenes; Sesquiterpenes, Germacrane; Time Factors

Some Curcuma species are widely used as herbal medicines. Sesquiterpenes are their important bioactive compounds and their quantitative analysis is generally accomplished by gas chromatography (GC) or high performance liquid chromatography (HPLC), but the instability and high cost of some sesquiterpene reference standards have limited their application. It is necessary to find a practicable means to control the quality of herbal medicines. Using one stable component contained in Curcuma species to determine multiple analogues should be a practical option. In this study, a simple HPLC method for determination of sesquiterpenes using relative response factors (RRFs) has been developed. The easily available and stable active component curdione was selected as the reference compound for calculating the RRFs of the other eight sesquiterpenes, including zedoarondiol (Zedo), isozedoarondiol (Isoz), aerugidiol (Aeru), (4S,5S)-(+)-germacrone-4,5-epoxide (Epox), curcumenone (Curc), neocurdione (Neoc), germacrone (Germ) and furanodiene (Fura). Their RRFs against curdione were between 0.131-1.301, with a good reproducibility. By using the RRFs, the quantification of sesquiterpenes in Curcuma wenyujin herbal medicines and related products was carried out. The method is especially useful for the determination of (4S,5S)-(+)-germacrone-4,5-epoxide, curcumenone, germacrone and furanodiene, which often are regarded as the principle components in Curcuma species, but unstable when were purified. It is an ideal means to analyze the components for which reference standards are not readily available.

Topics: Chromatography, High Pressure Liquid; Curcuma; Lactones; Plants, Medicinal; Reference Standards; Regression Analysis; Reproducibility of Results; Sesquiterpenes; Sesquiterpenes, Germacrane

Curdione, one of the major sesquiterpene compounds from Rhizoma Curcumae, has been shown to exhibit multiple bioactive properties. In this study, we investigated the anti-platelet aggregation and antithrombotic activities of curdione with different methods both in vitro and in vivo. The purpose of the study was to explore an inhibitor of platelet aggregation, which promised to be a preventive or therapeutic agent for various vascular diseases.. Curdione was isolated from the essential oil of Curcuma wenyujin using the silica gel column chromatography method. The effects of curdione on human platelet aggregation induced by thrombin (0.3 U/ml), platelet-activating factor (PAF, 0.375 μg/ml), adenosine diphosphate (ADP, 10 μM) and arachidonic acid (AA, 0.1mg/ml) were tested in vitro, and the potential mechanisms underlying such activities were investigated. We also tested the antithrombotic effect of curdione in a tail thrombosis model.. Curdione preferentially inhibited PAF- and thrombin- induced platelet aggregation in a concentration-dependent manner (IC(50): 60-80 μM), whereas much higher concentrations of curdione were required to inhibit platelet aggregation induced by ADP and AA. Curdione also inhibited P-selectin expression in PAF-activated platelets. Moreover, curdione caused an increase in cAMP levels and attenuated intracellular Ca(2+) mobilization in PAF-activated platelets. In vivo, we also found that curdione showed significant antithrombotic activity. Therefore, we conclude that the inhibitory mechanism of curdione on platelet aggregation may increase cAMP levels and subsequently inhibit intracellular Ca(2+) mobilization. Furthermore, the effect observed in the tail thrombosis model might be explained completely by increased vasodilation. These results indicate that curdione may be one of the main bioactive constituents in Rhizoma Curcumae that removes blood stasis.

Topics: Animals; Blood Platelets; Cells, Cultured; Curcuma; Dose-Response Relationship, Drug; Male; Mice; Oils, Volatile; Plant Oils; Platelet Aggregation; Platelet Aggregation Inhibitors; Sesquiterpenes, Germacrane; Treatment Outcome; Venous Thrombosis

To establish a HPLC method for determination of 4 components in different varieties of vinegar backed Rhizoma Curcuma.. The method was established by using an Elite Hypersil ODS2 column (4.6 mm x 250 mm, 5 microm). The mobile phase comprising acetonitrile (A) and water (B) was used to elute the targets in gradient elution mode. Flow rate and detection wavelength were set at 1 mL x min(-1) and 214 nm, respectively. The column temperature was 25 degrees C and the injection volume was 10 microL.. All calibration curves showed good linearity with r > 0.999 5. Recoveries measured at three concentrations were in the range of 97.27% - 99.27% with RSD < 3%.. The validated method is simple, reliable, and successfully applied to determine the contents of the selected compounds in vinegar backed Rhizoma Curcuma. The results of the determination showed that contents of the four components in vinegar backed Curcuma wenyujin were relatively high.

Topics: China; Chromatography, High Pressure Liquid; Curcuma; Drugs, Chinese Herbal; Rhizome; Sesquiterpenes; Sesquiterpenes, Germacrane

From the dried rhizomes of Curcuma comosa cultivating in Thailand, 26 known sesquiterpenes were isolated: zederone, zederone epoxide, furanodienone, isofuranodienone, 1(10)Z,4Z-furanodiene-6-one, glechomanolide, dehydrocurdione, neocurdione, curdione, 7 alpha-hydroxyneocurdione, 7 beta-hydroxycurdione, germacrone-1(10),4-diepoxide, germacrone, 13-hydroxygermacrone, curzerenone, curcolonol, alismol, alismoxide, zedoarondiol, isozedoarondiol, procurcumenol, isoprocurcumenol, aerugidiol, zedoalactone B, curcumenone, and curcumadione. Their structures were elucidated on the basis of physicochemical evidence. Among them, glechomanolide, curzerenone, curcolonol, alismol, alismoxide, and zedoarondiol showed no significant optical activities, so they may be artifact products during the isolation or drying process.

Topics: Curcuma; Furans; Heterocyclic Compounds, 2-Ring; Plant Extracts; Sesquiterpenes; Sesquiterpenes, Germacrane

To provide the scientific basis for the reasonable development and use of the leaves of Rhizoma Curcumae.. To extract the volatile oil from roots and leaves of three species Rhizoma Curcumae by steam distillation and isolate these products with the method of gas chromatography-mass spectrum. Taking Nist98 standard mass spectrometer database and contrast as control, the structure of the mass spectrogram was identified, and the relative contents of the components were determined with area normalization method.. The anti-tumor active constituents such as curdione and germacrone in the leaves had the greater content than in its rhizome.. The varieties of volatile components in different parts of three species of Rhizoma Curcumae are similar, but their contents are obviously various. We can make the leaves of Rhizoma Curcumae for recycling use.

Topics: Curcuma; Gas Chromatography-Mass Spectrometry; Oils, Volatile; Plant Leaves; Plants, Medicinal; Rhizome; Sesquiterpenes; Sesquiterpenes, Germacrane

The rhizomes of Curcuma phaeocaulis, Curcuma kwangsiensis, Curcuma wenyujin and Curcuma longa are used as Ezhu or Jianghuang in traditional Chinese medicine for a long time. Due to their similar morphological characters, it is difficult to distinguish their origins of raw materials used in clinic. In this study, a simple, rapid and reliable twice development TLC method was developed for qualitative and quantitative analysis of the four species of Curcuma rhizomes. The chromatography was performed on silica gel 60F(254) plate with chloroform-methanol-formic acid (80:4:0.8, v/v/v) and petroleum ether-ethyl acetate (90:10, v/v) as mobile phase for twice development. The TLC markers were colorized with 1% vanillin-H(2)SO(4) solution. The four species of Curcuma were easily discriminated based on their characteristic TLC profiles, and simultaneous quantification of eight compounds, including bisdemethoxycurcumin, demethoxycurcumin, curcumine, curcumenol, curcumol, curdione, furanodienone and curzerene, in Curcuma were also performed densitometrically at lambda(scan)=518nm and lambda(reference)=800 nm. The investigated compounds had good linearity (r(2)>0.9905) within test ranges. Therefore, the developed TLC method can be used for quality control of Curcuma rhizomes.

Topics: Acetates; Alkanes; Benzaldehydes; Chloroform; Chromatography, Thin Layer; Curcuma; Curcumin; Diarylheptanoids; Formates; Gels; Methanol; Plant Roots; Reference Standards; Reproducibility of Results; Sesquiterpenes; Sesquiterpenes, Germacrane; Silicon Dioxide; Solutions; Species Specificity; Sulfuric Acids; Time Factors

Overproduction of prostaglandins has been considered in mediation of inflammation and carcinogenic process. On this line, the inhibitors of prostaglandin biosynthetic enzyme cyclooxygenase (COX) have played a role of anti-inflammatory and cancer chemopreventive agents. In our continuous efforts to search anti-inflammatory and chemopreventive agents from natural products, bioassay-guided fractionation led to the isolation of curdione from the rhizome of Curcuma zedoaria with the inhibitory effect on the production of prostaglandin E2 in lipopolysaccharide (LPS)-stimulated mouse macrophage RAW 264.7 cells in a concentration-dependent manner (IC50 = 1.1 microM). Mechanistic studies suggest that the suppression of cyclooxygenase-2 (COX-2) mRNA expression is, at least in part, involved in this inhibitory activity of curdione.

Topics: Animals; Cell Line; Curcuma; Cyclooxygenase 2; Cyclooxygenase 2 Inhibitors; Dinoprostone; Dose-Response Relationship, Drug; Down-Regulation; Gene Expression Regulation, Enzymologic; Lipopolysaccharides; Macrophages; Mice; Plant Extracts; Rhizome; RNA, Messenger; Sesquiterpenes, Germacrane

Curcumol, germacrone and curdione are the main active ingredients in a common traditional Chinese medicine (TCM) of Rhizoma Curcuma, and commonly used as the TCM quality control markers. In the present work, microwave-assisted extraction (MAE) followed by headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS) was developed for the quantitative analysis of curcumol, curdione and germacrone in Rhizoma Curcuma. The MAE and HS-SPME parameters were studied, and the method was validated. The optimal MAE conditions obtained were: microwave power of 700 W and irradiation time of 4 min, and HS-SPME optimal conditions were: fiber coating of 100 microm PDMS, extraction temperature of 80 degrees C, extraction time of 20 min, stirring rate of 1,100 rpm, and salt concentration of 30% NaCl. The proposed method provided good precision (RSD less than 12%) and recoveries between 86% and 93%. The proposed method was applied to the determination of the three marker compounds in three species of Curcuma rhizomes (Curcuma wenyujin, Curcuma phaeocaulis, and Curcuma kwangsiensis). To demonstrate the proposed method reliability, a conventional technique of steam distillation was also used for the analysis of curcumol, germacrone and curdione in the TCMs. The results show that MAE-HS-SPME is a simple, rapid, solvent-free and reliable method for the determination of curdione, curcumol and germacrone in TCM, and also a potential and powerful tool for quality assessment of Rhizoma Curcuma.

Topics: Curcuma; Gas Chromatography-Mass Spectrometry; Microwaves; Reproducibility of Results; Sesquiterpenes; Sesquiterpenes, Germacrane

In this paper, GC-MS and pressurized liquid extraction (PLE) was developed for identification and quantitative determination/estimation 11 sesquiterpenes including germacrene D, curzerene, gamma-elemene, furanodienone, curcumol, isocurcumenol, furanodiene, germacrone, curdione, curcumenol and neocurdione in Ezhu which are derived from three species of Curcuma, i.e., Curcuma phaeocaulis, Curcuma wenyujin and Curcuma kwangsiensis by using an analogue as standard. The results showed the methodology could quantitatively compare the quality of three species of Curcuma. The contents of investigated sesquiterpenes in three species of Curcuma were high variant. Hierarchical clustering analysis based on characteristics of 11 identified peaks in GC profiles showed that 18 samples were divided into two main clusters, C. phaeocaulis and C. wenyujin, respectively. C. kwangsiensis showed the characters closed to C. phaeocaulis or C. wenyujin based on its location. Five components such as furanodienone, germacrone, curdione, curcumenol and neocurdione were optimized as markers for quality control of Ezhu.

Topics: Chemistry, Pharmaceutical; Chromatography; Chromatography, Ion Exchange; Chromatography, Liquid; Curcuma; Drug Industry; Furans; Gas Chromatography-Mass Spectrometry; Heterocyclic Compounds, 2-Ring; Magnetic Resonance Spectroscopy; Models, Chemical; Phylogeny; Quality Control; Sesquiterpenes; Sesquiterpenes, Germacrane

To study the fingerprint of Ezhu by GC-MS.. GC-MS analysis was performed for 18 samples of three species of Curcuma used as Ezhu. TIC profiles were evaluated by "Computer Aided Similarity Evaluation System" (MATLAB5.3 based, Ver. 1.240, developed by Research Center for Modernization of Chinese Medicine, Central South University). The characteristic peaks in chromatograms were identified by comparing mass data with literatures. Hierarchical clustering analysis was performed by SPSS based on the relative peak area (RPA) of identified peak to germacrone in 18 samples.. Resemblance values of 18 samples of Ezhu were pretty low. The mutual mode fingerprint plots of Ezhu were failed to develop. However, 18 samples were divided into two main clusters based on hierarchical clustering analysis, Curcuma wenyujin cluster and Curcuma phaeocaulis cluster, but the samples of Curcuma kwangsiensis were dispersive. Therefore, based on hierarchical clustering analysis, two mutual mode fingerprint plots of Curcuma wenyujin and Curcuma phaeocaulis were developed. But that of Curcuma kwangsiensis was failed because of low resemblance among samples.. The mutual mode fingerprint is the basis for quality control of Chinese materia medica from multi-origins. Development of GC-MS fingerprint of Ezhu was failed, which indicates that the chemical components in different species of herbs used as one Chinese materia medica may be significantly different. The relationship of chemical components and pharmacological activities should be further studied so as to elucidate the rationality of Chinese materia medica from multi-origins.

Topics: Cluster Analysis; Curcuma; Gas Chromatography-Mass Spectrometry; Phylogeny; Plant Roots; Plants, Medicinal; Quality Control; Reproducibility of Results; Sesquiterpenes; Sesquiterpenes, Germacrane