germacrone 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

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

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

Germacrone, curdione, and furanodiene have been shown to be useful in the treatment of breast cancer but the pharmacological mechanism of action is unclear. In this paper, we explored a new method to study the molecular network and function of Traditional Chinese Medicine (TCM) herbs and their corresponding ingredients with bioinformatics tools, including PubChem Compound Database, BATMAN-TCM, SystemsDock, Coremine Medical, Gene ontology, and KEGG. Eleven targeted genes/proteins, 4 key pathways, and 10 biological processes were identified to participate in the mechanism of action in treating breast cancer with germacrone, curdione, and furanodiene. The information achieved by the bioinformatics tools was useful to interpretation the molecular mechanism for the treatment of germacrone, curdione, and furanodiene on breast cancers.

Topics: Breast Neoplasms; Computational Biology; Drugs, Chinese Herbal; Female; Furans; Heterocyclic Compounds, 2-Ring; Humans; MCF-7 Cells; Medicine, Chinese Traditional; Molecular Targeted Therapy; Sesquiterpenes, Germacrane

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

A quantitative analysis of multiple components with a single-marker method was established for the simultaneous determination of five sesqutiterpenoids in Xingnaojing injection. This method was established with Xingnaojing injection determined by high-performance liquid chromatography coupled with diode array detection. The durability and system suitability of the established method were evaluated, and the reliable relative correction factors were obtained with curdione selected as an internal reference. The contents of the five components in all Xingnaojing injections were determined by external standard method and the contents of curcumenone, curcumenol, curzerenone, and germacrone were also calculated with the obtained relative correction factors. Then, relative error was investigated to estimate the difference of the two methods. As a result, the established new method possesses good adaptability, and there is no significant difference between the two methods, except for the content of curzerenone in eight samples. To put the established method into practice, the limits of quantitation of the established method of the five components were proposed and defined. Thus, the developed methodology can also be utilized to the quality evaluation of Xingnaojing injection, in spite of the difference found in the content of curzerenone between the external standard method and the newly established method.

Topics: Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Humans; Injections; Plant Extracts; Quality Control; Reference Standards; 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

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

High-speed counter-current chromatography (HSCCC) was applied to isolate and purify bioactive compounds in the essential oil of the rhizomes of Curcuma wenyujin. Two sesquiterpenes germacrone and curdione were successfully isolated and purified using two-phase solvent system composed of petroleum ether-ethanol-diethyl ether-water (5/4/0.5/1, v/v) in tail to head elution mode. 62 mg of germacrone and 93 mg of curdione were obtained from 658 mg of the essential oil each at over 95% purity. Their structures were identified by 1H NMR and EI MS.

Topics: Chromatography, High Pressure Liquid; Countercurrent Distribution; Indicators and Reagents; Magnetic Resonance Spectroscopy; Oils, Volatile; Sesquiterpenes, Germacrane; Spectrometry, Mass, Electrospray Ionization

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