ABSTRACT
In this study, three new germacranolide sesquiterpenes (1-3), together with six related known analogues (4-9) were isolated from the whole plant of Carpesium cernuum. Their structures were established by a combination of extensive NMR spectroscopic analysis, HR-ESIMS data, and ECD calculations. The anti-leukemia activities of all compounds towards three cell lines (HEL, KG-1a, and K562) were evaluated in vitro. Compounds 1-3 exhibited moderate cytotoxicity with IC
Subject(s)
Humans , Antineoplastic Agents, Phytogenic/pharmacology , Asteraceae/chemistry , Drug Screening Assays, Antitumor , K562 Cells , Phytochemicals/pharmacology , Sesquiterpenes, Germacrane/pharmacologyABSTRACT
The aim of this work was to evaluate the potential of the essential oil (EO) from Ocotea pulchella leaves as an alternative in the control of schistosomiasis. It was tested O. pulchella EO nanoformulation to assess its activity against adult Biomphalaria glabrata, their spawning and Schistossoma mansoni cercariae. Additionally, the EO chemical composition was investigated by gas-chromatography. Nanoemulsion were elaborated by the low energy method. The adult mollusks, their spawning and cercariae were placed in contact with nanoemulsion to calculate lethal concentrations. Myristicin, bicyclogermacrene and α-Pinene were the main substances in the EO. Nanoemulsion caused mortality of adult B. glabrata, its egg embryos and S. mansoni. These results suggest the use of this nanoemulsion as an alternative in the control of the schistosomiasis cycle.
El objetivo de este trabajo fue evaluar el potencial de los aceites esenciales (AE) de las hojas de Ocotea pulchellacomo una alternativa en el control de esquistosomiasis. Se probó una nanoformulación de AE de O. pulchellapara evaluar su actividad ante adultos de Biomphalaria glabrata, sus huevos y cercarías de Schistossoma mansoni. La nanoemulsión fue elaborada por el método de baja energía. Los moluscos adultos, sus huevos y cercarías se colocaron en contacto con la nanoemulsión para calcular concentraciones letales. Los compuestos mayoritarios en el AE fueron miristicina, biciclogermacreno y α-pineno. La nanoemulsión causó mortalidad en adultos de B. glabrata, sus huevos y a S. mansoni. Los resultados sugieren el uso de esta nanoemulsión como una alternativa en el control del ciclo de esquistosomiasis.
Subject(s)
Animals , Schistosomiasis/prevention & control , Oils, Volatile/administration & dosage , Ocotea/chemistry , Emulsions/administration & dosage , Mollusca/drug effects , Schistosoma mansoni/drug effects , Biomphalaria/drug effects , Oils, Volatile/pharmacology , Oils, Volatile/chemistry , Pest Control, Biological , Chromatography, Gas , Sesquiterpenes, Germacrane/analysis , Dioxolanes/analysis , Emulsions/pharmacology , Cercaria/drug effects , Hydrophobic and Hydrophilic Interactions , Allylbenzene Derivatives/analysis , Bicyclic Monoterpenes/analysisABSTRACT
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.
Subject(s)
Acetic Acid , Chemistry , Curcuma , Chemistry , Drugs, Chinese Herbal , Gas Chromatography-Mass Spectrometry , Methods , Oils, Volatile , Chemistry , Plant Oils , Chemistry , Sesquiterpenes , Sesquiterpenes, GermacraneABSTRACT
Herb combination has been very popular in traditional medical prescriptions such as Traditional Chinese Medicine [TCM]. Persistent efforts and attempts have been made to dissect the action mode of TCM in recent years, which has provided certain evidence for inter-herbal interactions. However, the interactions among different components in a single herb have been largely neglected. In this experimental study, the interactions among different components of a single herb were explored. The effect of three main sesquiterpenes [germacrone, curdione, furanodiene] isolated from Curcuma WenyujinY.H. Chenet C Ling on MDA-MB-231 and MCF-7 breast cancer cell proliferation alone or in combination with a fixed-dose-combination was investigated. Furanodiene significantly inhibited cancer cell proliferation while germacrone and curdione showed no effect. Germacrone enhanced furanodiene's anti-proliferative effect. Curdione showed no effect on furanodiene's anti-proliferative effect but partly reversed the anti-proliferative effect of germacrone and furanodiene combined. The morphological and mitochondrial membrane potential [delta [PSI]m] changes showed similar results. However, they demonstrated complicated interactions on the expression of apoptotic-related proteins and key signal transduction proteins. Unpredictable and complex interactions among different components in Curcuma WenyujinY.H.Chenet C Ling may exist. The intra-herb interactions should be taken into consideration when attempts are made to interpret the art of TCM formulation or other similar recipes
Subject(s)
Humans , Sesquiterpenes, Germacrane , Furans , Heterocyclic Compounds, 2-Ring , Cell Proliferation , Herb-Drug Interactions , Medicine, Chinese TraditionalABSTRACT
Previous studies have shown that STAT3 plays a vital role in the genesis and progression of cancer. In this study, we investigated the relationship between the JAK2/STAT3 signalling pathway and germacrone-induced apoptosis in HepG2 cells. HepG2 cells were incubated with germacrone for 24 h, the protein expression of p-STAT3, STAT3, p-JAK2 and JAK2 was detected by Western Blotting, and RT-PCR was used to determine the expression of STAT3, p53, Bcl-2 and Bax at transcriptional levels. Besides that, HepG2 cells were pre-treated with AG490 or IL-6 for 2 h, and then incubated with germacrone for 24 h. The expression of p-JAK2, JAK2, p-STAT3, STAT3, p53, Bax and Bcl-2 was detected by Western blotting. The activity of HepG2 cells was tested by MTT assay. The apoptosis of HepG2 cells and levels of reactive oxygen species (ROS) were flow cytometrically measured. The results showed that germacrone exposure decreased p-STAT3 and p-JAK2 and regulated expression of p53 and Bcl-2 family members at the same time. Moreover, IL-6 enhanced the activation of the JAK2/STAT3 signalling pathway and therefore attenuated the germacrone-induced apoptosis. Suppression of JAK2/STAT3 signalling pathway by AG490, an inhibitor of JAK2, resulted in apoptosis and an increase in ROS in response to germacrone exposure. We therefore conclude that germacrone induces apoptosis through the JAK2/STAT3 signalling pathway.
Subject(s)
Humans , Apoptosis , Dose-Response Relationship, Drug , Drugs, Chinese Herbal , Hep G2 Cells , Janus Kinase 2 , Metabolism , STAT3 Transcription Factor , Metabolism , Sesquiterpenes, Germacrane , Signal TransductionABSTRACT
<p><b>OBJECTIVE</b>To study zedoary turmeric oil (ZTO) and the pharmacokinetics of its homemade compound antiviral preparation in New Zealand rabbits.</p><p><b>METHOD</b>RP-HPLC was used to determinate the content of germacrone in rabbit plasma after oral administration.</p><p><b>RESULT</b>After oral administration of ZTO and its homemade compound antiviral preparation, the plasma concentration-time curve of germacrone is in conformity to two-compartment open model. The pharmacokinetic parameters of ZTO: t1/2alpha, t1/2beta, Vd, CL, AUC and Ka were (1.52 +/- 0.59), (1.97 +/- 0.27) h, (47.59 +/- 2.29) L x kg(-1), (176.77 +/- 7.65) L x h(-1) x kg(-1), (5.70 +/- 0.70) mg x h x L(-1) and (0.97 +/- 0.11) h(-1), respectively, while those of compound preparation were (0.41 +/- 0.03), (1.47 +/- 0.35) h, (75.21 +/- 5.21) L x kg(-1), (287.79 +/- 6.39) L x h(-1) x kg(-1), (3.91 +/- 0.53) mg x h x L(-1) and (5.14 +/- 1.26) h(-1), respectively. There was no significant difference between the above two groups of pharmacokinetic parameters, expect that Ka of compound preparation was significantly higher than that of ZTO (P < 0.05).</p><p><b>CONCLUSION</b>Hypericum perforatum in compound preparation doesn't impact the distribution and elimination of active ingredients of ZTO in New Zealand rabbits, but it improves the absorption speed, and shortens the time of drug absorption, which contributes to rapid efficacy of ZTO in rabbits.</p>
Subject(s)
Animals , Male , Rabbits , Antiviral Agents , Pharmacokinetics , Curcuma , Chemistry , Drug Compounding , Drug Interactions , Drugs, Chinese Herbal , Pharmacology , Hypericum , Chemistry , Plant Oils , Pharmacokinetics , Sesquiterpenes, Germacrane , PharmacokineticsABSTRACT
Lutzomyia longipalpis s.l. is the primary vector of Leishmania (L.) infantum in the New World. In this study, male Lutzomyia longipalpis specimens from Posadas, Argentina were characterized for two polymorphic markers: the male sex pheromone and the period (per) gene. The male sex pheromone was identified as (S)-9-methylgermacrene-B, the same compound produced by Lu. longipalpis from Paraguay and many populations from Brazil. The analysis of per gene sequences revealed that the population from Argentina is significantly differentiated from previously studied Brazilian populations. Marker studies could contribute to the understanding of the distribution and spread of urban American visceral leishmaniasis, thus aiding in the design of regional surveillance and control strategies.
Subject(s)
Animals , Male , Insect Vectors , Psychodidae , Sesquiterpenes, Germacrane , Sex Attractants , ArgentinaABSTRACT
OBJECTIVE: The sesquiterpene, mikanolide, was found to possess antibacterial activity. As a result, a structure-activity relationship study was carried out on mikanolide and eleven of its derivatives. METHODS: Mikanolide and two of its derivatives were isolated from organic extract of Mikania micrantha using chromatographic methods. Nine additional derivatives were synthesized and all were investigated for their antibacterial activity against the Gram positive pathogen Staphylococcus aureus and beta haemolytic Streptococcus group A (BHSA) as well as the Gram negative Escherichia coli using the disk diffusion assay. RESULTS: The investigation revealed that only four of the derivatives displayed antibacterial activity and only pathogens Staphylococcus aureus and beta haemolytic Streptococcus group A were susceptible at a concentration of 100 µg per disk. However, there was an increase in activity for three of the derivatives in comparison to mikanolide. CONCLUSION: This study underscores the potential for phytochemicals from locally available plants to be further investigated and developed as antibacterial agents.
OBJETIVO: Se halló que el sesquiterpene - mikanolida - posee actividad antibacteriana. Como resultado, se llevó a cabo un estudio de la relación estructura-actividad de la mikanolida y once de sus derivados. MÉTODOS: La mikanolida y dos de sus derivados fueron aislados a partir de un extracto orgánico de Mikania micrantha, mediante métodos cromatográficos. Se sintetizaron otros nueve derivados adicionales, y se investigó la actividad antibacteriana de todos sobre el patógeno Gram positivo Staphylococcus aureus y el Streptococcus beta hemolítico grupo A (BHSA) así como Escherichia coli Gram negativo, usando el ensayo de difusión en disco. RESULTADOS: La investigación reveló que sólo cuatro de los derivados mostraban actividad antibacteriana y sólo los patógenos Staphylococcus aureus y Streptococcus beta hemolítico grupo A eran susceptibles a una concentración de 100 µg por disco. Sin embargo, se produjo un aumento en la actividad de tres de los derivados en comparación con la mikanolida. CONCLUSIÓN: Este estudio subraya el potencial que poseen los fotoquímicos a partir de plantas localmente disponibles, para ser objeto de investigación ulterior y ser desarrollados como agentes antibacterianos.
Subject(s)
Humans , Lactones/pharmacology , Sesquiterpenes, Germacrane/pharmacology , Anti-Bacterial Agents/pharmacology , Disk Diffusion Antimicrobial Tests , Staphylococcus aureus/drug effects , Streptococcus pyogenes/drug effects , Structure-Activity RelationshipABSTRACT
<p><b>OBJECTIVE</b>To establish a HPLC method for determination of 4 components in different varieties of vinegar backed Rhizoma Curcuma.</p><p><b>METHOD</b>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.</p><p><b>RESULT</b>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%.</p><p><b>CONCLUSION</b>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.</p>
Subject(s)
China , Chromatography, High Pressure Liquid , Methods , Curcuma , Chemistry , Drugs, Chinese Herbal , Rhizome , Chemistry , Sesquiterpenes , Sesquiterpenes, GermacraneABSTRACT
The chemical components of the essential oil obtained from Chrysanthemum indicum L. were analyzed by GC-MS. Seventy-three compounds accounting for 96.65% of the extracted essential oil were identified. The main compounds in the oil were alpha-pinene (4.4%), 1,8-cineole (10.4%), alpha-thujone (6.05%), camphor (10.12%), terpinen-4-ol (3.4%), bornyl acetate (6.1%), borneol (3.6%), cis-chrysanthenol (3.4%), beta-caryophyllene (5.1%), germacrene D (10.6%), and alpha-cadinol (3.0%). The essential oil of C. indicum exhibited stronger antibacterial activity against all oral bacteria tested (MICs, 0.1 to 1.6 mg/ml; MBCs, 0.2 to 3.2 mg/ml) than their major compounds. Furthermore, the MICs/MBCs were reduced to one half ~ one sixteenth as a result of the combinations included the essential oil with ampicillin or gentamicin for all oral bacteria. A strong bactericidal effect was exerted in drug combinations. The in vitro data suggest that the essential oil of C. indicum with other antibiotics may be microbiologically beneficial and synergistic.
Subject(s)
Accounting , Ampicillin , Anti-Bacterial Agents , Bacteria , Camphanes , Camphor , Chrysanthemum , Cyclohexanols , Drug Combinations , Gentamicins , Monoterpenes , Sesquiterpenes , Sesquiterpenes, Germacrane , TerpenesABSTRACT
O presente trabalho descreve a avaliação da atividade antimicrobiana de uma fração sesquiterpênica, obtida a partir do extrato CH2Cl2 de Senecio desiderabilis Vellozo (Asteraceae), e do germacreno D, isolado a partir desta. A fração e o germacreno D foram obtidos mediante cromatografia em coluna e analisados por CG-EM e também por RMN, no caso da substância isolada. A atividade antimicrobiana foi avaliada frente a leveduras e bactérias pelo método de microdiluição em caldo, conforme preconizado pelo NCCLS, nos documentos M27-A2 para fungos leveduriformes, e M7-A4 para bactérias. A fração sesquiterpênica evidenciou moderada atividade antimicrobiana, enquanto que o germacreno D não inibiu o crescimento dos microrganismos testados.
The present work describes the evaluation of the antimicrobial activity of a sesquiterpene fraction obtained from CH2Cl2 extract of Senecio desiderabilis Vellozo (Asteraceae), and of germacrene D isolated from it. The sesquiterpene fraction and the isolated substance were obtained by column chromatography and analysed by GC-MS. Substance identification was carried out by NMR. The antimicrobial activity was assayed by broth microdilution method, as preconized by NCCLS in the documents M27-A for yeasts and M7-A4 for bacteria. The sesquiterpene fraction showed moderated antimicrobial activity, and germacrene D did not inhibit the tested microorganisms.
Subject(s)
Anti-Bacterial Agents , Asteraceae , Plant Extracts , Senecio , Sesquiterpenes, GermacraneABSTRACT
Neste trabalho é relatada a avaliação da atividade antimicrobiana dos extratos diclorometânico e etanólico, obtidos por maceração das partes aéreas de S. heterotrichius pelo método de microdiluição em caldo, frente a patógenos bacterianos e fúngicos. O extrato diclorometânico evidenciou boa atividade inibitória frente a Candida krusei (CIM de 0,25 mg/mL) e moderada atividade frente a Staphylococcus aureus (CIM de 2,5 mg/mL). O extrato etanólico mostrou-se inativo frente aos microrganismos testados. Também foi isolado o constituinte majoritário do extrato diclorometânico, cuja análise espectroscópica indicou tratar-se de um sesquiterpeno, identificado como germacreno D.
This work describes the evaluation of the antimicrobial activity of CH2Cl2 and EtOH extracts obtained by the maceration of the aerial parts of Senecio heterotrichius DC. against bacterial and fungal pathogens by broth microdilution method. The CH2Cl2 extract showed the best activity against Candida krusei (MIC 0.25 mg/mL) and a moderate activity against Staphyllococcus aureus (MIC 2.5 mg/mL). The EtOH extract was inactive against the tested microorganisms. Besides, one of the main constituents of CH2Cl2 extract was isolated, and its spectroscopic analysis indicated the presence of a sesquiterpene identified as germacrene D.
Subject(s)
Asteraceae , Plant Extracts , Senecio/microbiology , Hydrocarbons , Sesquiterpenes, GermacraneABSTRACT
Volatile components of three parts of Pimpinella tragium Vill. [Umbelliferae family] from Iran were investigated qualitatively and quantitatively for the first time. Essential oils were isolated by hydro-distillation from stems plus leaves, inflorescence and seeds of P. tragium individually. The plant materials were collected from Polour [Northeast of Tehran Province]. The yields of the stems plus leaves, inflorescence and seed oils were 0.08%, 0.37% and 1.33%w/w, respectively. Eighteen constituents in the stems plus leaves oil, twenty-six constituents in the inflorescence oil and twenty-three constituents in the seed oil were identified. Major constituents of the stems plus leaves oil were: germacrene D [34.7%], germacrene B [18.3%], bornyl acetate [15.8%], beta-caryophyllene [5.6%] and beta-pinene [4.5%]. Major constituents of the inflorescence oil were: beta-pinene [23.8%], germacrene B [14.1%], hexadecanol [10.3%], beta-caryophyllene [7.3%], germacrene D [6.2%] and bornyl acetate [4.1%]. Main components of the seed oil were: beta-pinene [25.3%], germacrene B [17.8%], sabinene [13.6%], beta-caryophyllene [4.8%] and hexadecanol [4.7%]
Subject(s)
Oils, Volatile , Apiaceae , Sesquiterpenes, Germacrane , MonoterpenesABSTRACT
<p><b>AIM</b>To study the fingerprint of Ezhu by GC-MS.</p><p><b>METHODS</b>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.</p><p><b>RESULTS</b>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.</p><p><b>CONCLUSION</b>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.</p>
Subject(s)
Cluster Analysis , Curcuma , Chemistry , Classification , Gas Chromatography-Mass Spectrometry , Phylogeny , Plant Roots , Chemistry , Plants, Medicinal , Chemistry , Classification , Quality Control , Reproducibility of Results , Sesquiterpenes , Sesquiterpenes, GermacraneABSTRACT
<p><b>AIM</b>To study the absorption of zedoary oil in intestine of rat.</p><p><b>METHODS</b>In situ single pass perfusion model was used and the concentrations of three components in perfusate were determined by HPLC in combination with diode array detection.</p><p><b>RESULTS</b>The P(app) s of curcumol, curdione and germacrone were all low and had no significant difference (P > 0.05) at zedoary oil concentration of 0.4, 0.8 and 1.2 mg x mL(-1) in transmucosal fluid or in four different regions of intestine of rat [duodenum, jejunum, ileum, colon]. The absorption rates of germacrone and curdione were faster than curcumol's in this study.</p><p><b>CONCLUSION</b>The zedoary oil concentration in transmucosal fluid had no significant effect on the P(app) s within the scope of 0.4-1.2 mg x mL(-1). The absorption of curcumol, curdione and germacrone showed the passive diffusion process, and didn't contain a special absorption window.</p>