curdione and curcumol

Influenza virus is one of the most widespread infectious diseases in the world. It poses a serious public health threat to humans. With the emergence of drug-resistant virus strains, antiviral drugs are urgently needed to control virus transmission and disease progression. In this study, three main active substances-curcumol, curdione and germacrone-were isolated from the traditional Chinese medicine zedoary. They inhibited the replication of influenza A (H1N1) virus in a dose-dependent manner. After treatment with these compounds, the expression of viral protein and RNA synthesis were inhibited. In vivo, these compounds also reduced H1N1-induced lung damage and the load of virus in serum as well as whole blood cells. In a proteomic analysis, after treatment with germacrone, the expression of antiviral protein and the amount of intracellular virus were significantly reduced, further proving that germacrone can inhibit viral replication. Our experiments have shown that curcumol, curdione and germacrone can inhibit the replication of H1N1 virus; in particular, germacrone shows potential both in vitro and in vivo as a therapeutic drug.

Topics: A549 Cells; Animals; Antiviral Agents; Cell Proliferation; Drugs, Chinese Herbal; HEK293 Cells; Humans; Influenza A Virus, H1N1 Subtype; Mice; Mice, Inbred BALB C; Molecular Structure; Oils; Orthomyxoviridae Infections; Sesquiterpenes; Sesquiterpenes, Germacrane; Specific Pathogen-Free Organisms

Topics: Animals; Anoctamin-1; Cell Line; Chloride Channel Agonists; Chloride Channels; Epithelial Cells; Furans; HT29 Cells; Humans; Male; Mice; Mice, Inbred C57BL; Neoplasm Proteins; Rats; 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

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

A sensitive, specific, convenient and endogenous interference-free microdialysis sampling method coupled with RRLC-MS was successfully developed and applied to the determination of protein-unbound curdione and curcumol in biological samples. Microdialysis probes were simultaneously inserted into the jugular vein toward heart and the median lobe near the center of liver of rats under anesthesia. The separation was accomplished on a Zorbax SB-C18 column (2.1 mm × 50 mm, 1.8 μm) with a gradient elution and chromatography was conducted with RRLC system. Analytes were detected by positive ion electrospray tandem mass spectrometry and quantified on the basis of extracted ion chromatography (EIC) peak area signal. The calibration curves were linear over the range of 3.3-213.2 ng/mL for curdione and 8.1-519.2 ng/mL for curcumol. All the validation data, such as accuracy, precision, stability and matrix effect were satisfactory and within the required limits. The validated method was successfully applied to the pharmacokinetic study of curdione and curcumol in rat blood and liver after oral administration of Rhizoma Curcumae extracts. The results could provide a meaningful basis for better understanding of the intracorporal process of Rhizoma Curcumae, which would be helpful for further study both in clinic and laboratory.

Topics: Animals; Chromatography, High Pressure Liquid; Liver; Male; Microdialysis; Rats; Rats, Sprague-Dawley; Sesquiterpenes; Sesquiterpenes, Germacrane; Tandem Mass Spectrometry

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

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