RESUMO
The family Asteraceae comprises many species that have medicinal importance in terms of their chemical components. Some species of the genus Lactuca have been used in folk medicine for a long time ago. One of them is L. serriola L., a wild plant that is a weed in agriculture. To date, few studies have been published on its chemical profile. In this research, we investigated the volatile compounds and fatty acids of L. serriola roots, leaves, and seeds. To this end, a microsteam distillation-solid phase microextraction technique (MSD-SPME) followed by a gas chromatography-mass spectrometry analysis was performed. Aldehydes and terpenoids were predominantly present in the leaves with phenylacetaldehyde as the major compound (up to 18%) while 2-ethyl hexanol (up to 36.9%) was the most abundant substance in the roots. Among the fatty acids, nonadecanoic acid (38.3%) was the main one detected in the leaves, while linoleic acid (57.7%) was predominant in the seeds. Some of the detected constituents have already demonstrated importance in medicinal and industrial areas. As a result, this species could be further investigated for its biological features and be considered as a source of ingredients beneficial in different fields, including pharmaceuticals.
Assuntos
Asteraceae , Compostos Orgânicos Voláteis , Asteraceae/química , Terpenos , Folhas de Planta/química , Ácidos Graxos , Aldeídos , Compostos Orgânicos Voláteis/análiseRESUMO
Grindelia squarrosa (Pursh) Dunal is used in traditional medicine for treating various diseases; however, little is known about the immunomodulatory activity of essential oils from this plant. Thus, we isolated essential oils from the flowers (GEOFl) and leaves (GEOLv) of G. squarrosa and evaluated the chemical composition and innate immunomodulatory activity of these essential oils. Compositional analysis of these essential oils revealed that the main components were α-pinene (24.7 and 23.2% in GEOFl and GEOLv, respectively), limonene (10.0 and 14.7%), borneol (23.4 and 16.6%), p-cymen-8-ol (6.1 and 5.8%), ß-pinene (4.0 and 3.8%), bornyl acetate (3.0 and 5.1%), trans-pinocarveol (4.2 and 3.7%), spathulenol (3.0 and 2.0%), myrtenol (2.5 and 1.7%), and terpinolene (1.7 and 2.0%). Enantiomer analysis showed that α-pinene, ß-pinene, and borneol were present primarily as (-)-enantiomers (100% enantiomeric excess (ee) for (-)-α-pinene and (-)-borneol in both GEOFl and GEOLv; 82 and 78% ee for (-)-ß-pinene in GEOFl and GEOLv), while limonene was present primarily as the (+)-enantiomer (94 and 96 ee in GEOFl and GEOLv). Grindelia essential oils activated human neutrophils, resulting in increased [Ca2+]i (EC50 = 22.3 µg/mL for GEOFl and 19.4 µg/mL for GEOLv). In addition, one of the major enantiomeric components, (-)-borneol, activated human neutrophil [Ca2+]i (EC50 = 28.7 ± 2.6), whereas (+)-borneol was inactive. Since these treatments activated neutrophils, we also evaluated if they were able to down-regulate neutrophil responses to subsequent agonist activation and found that treatment with Grindelia essential oils inhibited activation of these cells by the N-formyl peptide receptor 1 (FPR1) agonist fMLF and the FPR2 agonist WKYMVM. Likewise, (-)-borneol inhibited FPR-agonist-induced Ca2+ influx in neutrophils. Grindelia leaf and flower essential oils, as well as (-)-borneol, also inhibited fMLF-induced chemotaxis of human neutrophils (IC50 = 4.1 ± 0.8 µg/mL, 5.0 ± 1.6 µg/mL, and 5.8 ± 1.4 µM, respectively). Thus, we identified (-)-borneol as a novel modulator of human neutrophil function.
Assuntos
Grindelia , Óleos Voláteis , Canfanos , Grindelia/química , Humanos , Limoneno/análise , Neutrófilos , Óleos Voláteis/química , Folhas de Planta/química , Óleos de Plantas/químicaRESUMO
Rhododendron (Ericaceae) extracts contain flavonoids, chromones, terpenoids, steroids, and essential oils and are used in traditional ethnobotanical medicine. However, little is known about the immunomodulatory activity of essential oils isolated from these plants. Thus, we isolated essential oils from the flowers and leaves of R. albiflorum (cascade azalea) and analyzed their chemical composition and innate immunomodulatory activity. Compositional analysis of flower (REOFl) versus leaf (REOLv) essential oils revealed significant differences. REOFl was comprised mainly of monoterpenes (92%), whereas sesquiterpenes were found in relatively low amounts. In contrast, REOLv was primarily composed of sesquiterpenes (90.9%), with a small number of monoterpenes. REOLv and its primary sesquiterpenes (viridiflorol, spathulenol, curzerene, and germacrone) induced intracellular Ca2+ mobilization in human neutrophils, C20 microglial cells, and HL60 cells transfected with N-formyl peptide receptor 1 (FPR1) or FPR2. On the other hand, pretreatment with these essential oils or component compounds inhibited agonist-induced Ca2+ mobilization and chemotaxis in human neutrophils and agonist-induced Ca2+ mobilization in microglial cells and FPR-transfected HL60 cells, indicating that the direct effect of these compounds on [Ca2+]i desensitized the cells to subsequent agonist activation. Reverse pharmacophore mapping suggested several potential kinase targets for these compounds; however, these targets were not supported by kinase binding assays. Our results provide a cellular and molecular basis to explain at least part of the beneficial immunotherapeutic properties of the R. albiflorum essential oils and suggest that essential oils from leaves of this plant may be effective in modulating some innate immune responses, possibly by inhibition of neutrophil migration.
Assuntos
Óleos Voláteis/química , Rhododendron/química , Flores/química , Células HL-60 , Humanos , Fatores Imunológicos/isolamento & purificação , Fatores Imunológicos/metabolismo , Imunomodulação/efeitos dos fármacos , Monoterpenos/farmacologia , Neutrófilos/efeitos dos fármacos , Óleos Voláteis/farmacologia , Folhas de Planta/química , Receptores de Formil Peptídeo/efeitos dos fármacos , Receptores de Formil Peptídeo/metabolismo , Rhododendron/metabolismo , Sesquiterpenos/farmacologiaRESUMO
Hypericum L. (Hypericaceae) extracts have been used for their therapeutic effects; however, not much is known about the immunomodulatory activity of essential oils extracted from this plant. We isolated essential oils from the flowers and leaves of H. perforatum and analyzed their chemical composition and innate immunomodulatory activity. Analysis of flower (HEOFl) versus leaf (HEOLv) essential oils using gas chromatography-mass spectrometry revealed that HEOFl was comprised mainly of monoterpenes (52.8%), with an abundance of oxygenated monoterpenes, including cis-p-menth-3-en-1,2-diol (9.1%), α-terpineol (6.1%), terpinen-4-ol (7.4%), and limonen-4-ol (3.2%), whereas the sesquiterpenes were found in trace amounts. In contrast, HEOLv was primarily composed of sesquiterpenes (63.2%), including germacrene D (25.7%) and ß-caryophyllene (9.5%). HEOLv also contained oxygenated monoterpenes, including terpinen-4-ol (2.6%), while monoterpene hydrocarbons were found in trace amounts. Both HEOFl and HEOLv inhibited neutrophil Ca2+ mobilization, chemotaxis, and reactive oxygen species (ROS) production, with HEOLv being much more active than HEOFl. Furthermore, the pure sesquiterpenes germacrene D, ß-caryophyllene, and α-humulene also inhibited these neutrophil responses, suggesting that these compounds represented the active components of HEOLv. Although reverse pharmacophore mapping suggested that potential protein targets of germacrene D, ß-caryophyllene, bicyclogermacrene, and α-humulene could be PIM1 and mitogen-activated protein kinase (MAPK)-activated protein kinase 2 (MAPKAK2), a kinase binding affinity assay did not support this finding, implying that other biological targets are involved. Our results provide a cellular and molecular basis to explain at least part of the beneficial immunotherapeutic properties of the H. perforatum essential oils.
Assuntos
Hypericum/química , Imunomodulação/efeitos dos fármacos , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Movimento Celular/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Flores/química , Humanos , Imunomodulação/imunologia , Modelos Moleculares , Conformação Molecular , Neutrófilos/efeitos dos fármacos , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Células Tumorais CultivadasRESUMO
Chlorogenic (5-CQA), 1,5-, 3,5-, 4,5- and 3,4-dicaffeoylquinic (DCQA) acids were identified and quantified in the methanol extracts of Inula oculus-christi L., I. bifrons L., I. aschersoniana Janka var. aschersoniana, I. ensifolia L., I. conyza (Griess.) DC. and I. germanica L. by HPLC analysis. The amount of 5-CQA varied from 5.48 to 28.44â mg/g DE and the highest content was detected in I. ensifolia. 1,5-DCQA (4.05-55.25â mg/g DE) was the most abundant dicaffeoyl ester of quinic acid followed by 3,5-DCQA, 4,5-DCQA and 3,4-DCQA. The extract of I. ensifolia showed the highest total phenolic content (119.92±0.95â mg GAE/g DE) and exhibited the strongest DPPH radical scavenging activity (69.41±0.55 %). I. bifrons extract was found to be the most active sample against ABTS.+ (TEAC 0.257±0.012â mg/mL) and the best tyrosinase inhibitor. The studied extracts demonstrated a low inhibitory effect towards acetylcholinesterase and possessed low cytotoxicity in concentration range from 10 to 300â µg/mL toward non-cancer (MDCK II) and cancer (A 549) cells.
Assuntos
Acetilcolinesterase/química , Antioxidantes/química , Inibidores Enzimáticos/química , Inula/química , Monofenol Mono-Oxigenase/antagonistas & inibidores , Ácido Quínico/análogos & derivados , Acetilcolinesterase/metabolismo , Animais , Bulgária , Sobrevivência Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Cães , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Flores/química , Flores/metabolismo , Humanos , Inula/metabolismo , Células Madin Darby de Rim Canino , Monofenol Mono-Oxigenase/metabolismo , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Extratos Vegetais/química , Folhas de Planta/química , Folhas de Planta/metabolismo , Ácido Quínico/química , Ácido Quínico/isolamento & purificação , Ácido Quínico/farmacologiaRESUMO
Hexane extracts of Heracleum verticillatum, H. sibiricum, H. angustisectum, and H. ternatum were studied for their furanocoumarin content antioxidant potential and acetylcholinesterase and α-amylase inhibitory activities. Quantification of the furanocoumarins was performed by 1 H-NMR. Pimpinellin was found to be the main component in the roots of all studied species. Bergapten and imperatorin were the major compounds in the fruits of H. sibiricum and H. verticillatum, respectively, while byakangelicol dominated in H. angustisectum and H. ternatum fruits. The leaf and fruit extracts of H. angustisectum demonstrated the highest DPPH radical scavenging activity and TEAC (IC50 0.58â mg/mL and 1.83â mm, respectively). The root extracts of H. verticillatum and H. angustisectum were found to be the most effective against acetylcholinesterase (IC50 0.30 and 0.34â mg/mL, respectively). The studied extracts were not active or demonstrated a weak inhibitory effect (%Inh. up to 29.7) towards α-amylase.
Assuntos
Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Inibidores Enzimáticos/farmacologia , Furocumarinas/farmacologia , Heracleum/química , Hipoglicemiantes/farmacologia , Picratos/antagonistas & inibidores , Acetilcolinesterase/metabolismo , Doença de Alzheimer/tratamento farmacológico , Doença de Alzheimer/metabolismo , Animais , Antioxidantes/síntese química , Antioxidantes/química , Diabetes Mellitus Tipo 2/tratamento farmacológico , Electrophorus , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/química , Furocumarinas/síntese química , Furocumarinas/química , Humanos , Hipoglicemiantes/síntese química , Hipoglicemiantes/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Suínos , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/metabolismoRESUMO
Essential oils (EOs) were obtained by hydrodistillation of various parts of Ferula ovina (Boiss.) Boiss., Ferula iliensis Krasn. ex. Korovin, and Ferula akitschkensis B. Fedtsch. ex Koso-Pol., collected in the flowering/budding and fruiting stages. Eight samples of EOs isolated from F. ovina and four samples from F. akitsckensis were analyzed by gas chromatographyâ»mass spectrometry (GC-MS). The major constituents of F. ovina EOs were α-pinene (6.9â»47.8%), ß-pinene (1.5â»7.1%), sabinene (0.1â»20.5%), ß-phellandrene (0â»6.5%), trans-verbenol (0.9â»7.4%), eremophilene (3.1â»12%), and 6Z-2,5,5,10-tetramethyl-undeca-2,6,9-trien-8-one (0â»13.7%). The major constituents of F. akitsckensis EOs were α-pinene (0â»46.2%), ß-pinene (0â»47.9%), sabinene (0â»28.3%), eremophilene (0â»10.6), ß-caryophyllene (0â»7.5%), himachalen-7-ol (0â»28.2%), and an himachalol derivative (0â»8.3%). Samples of EOs from F. ovina, F. iliensis, and F. akitsckensis were evaluated for antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) pulse-field gel electrophoresis type USA300 (LAC). EOs from F. ovina exhibited the highest antibacterial activity compared to samples from other Ferula spp., with the most potent EOs being isolated from roots at the flowering and fruiting stages and stems at the fruiting stage (IC50 values of 19.1, 20.9, and 22.9 µg/mL, respectively). Although EOs demonstrated concentration-dependent inhibition of MRSA growth, analysis of the major constituents (α-pinene, ß-pinene, and sabinene) showed that they had low activity, suggesting that other components were likely responsible for the observed bioactivity of the unfractionated EOs. Indeed, correlation of the GC-MS data with antibacterial activity suggested that the putative components responsible for antibacterial activity were, either individually or in combination, eremophilene and trans-verbenol. Overall, these results suggest that the EOs from F. ovina could have potential for use as alternative remedies for the treatment of infectious diseases caused by MRSA.
Assuntos
Antibacterianos/química , Antibacterianos/farmacologia , Ferula/química , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Modelos Lineares , Testes de Sensibilidade MicrobianaRESUMO
CONTEXT: Almond oil is used in traditional and complementary therapies for its numerous health benefits due to high unsaturated fatty acids content. OBJECTIVES: This study investigated the composition and in vitro anticancer activity of almond oil from Northern Cyprus and compared with almond oil from Turkey. MATERIALS AND METHODS: Almond oil from Northern Cyprus was obtained by supercritical CO2 extraction and analyzed by GC-MS. Almond oil of Turkey was provided from Turkish pharmacies. Different concentrations of almond oils were incubated for 24 and 48 h with Colo-320 and Colo-741 cells. Cell growth and cytotoxicity were measured by MTT assays. Anticancer and antiprolifetarive activities of almond oils were investigated by immunocytochemistry using antibodies directed against to BMP-2, ß-catenin, Ki-67, LGR-5 and Jagged 1. RESULTS: Oleic acid (77.8%; 75.3%), linoleic acid (13.5%; 15.8%), palmitic acid (7.4%; 6.3%), were determined as the major compounds of almond oil from Northern Cyprus and Turkey, respectively. In the MTT assay, both almond oils were found to be active against Colo-320 and Colo-741 cells with 1:1 dilution for both 24 h and 48 h. As a result of immunohistochemical staining, while both almond oils exhibited significant antiproliferative and anticancer activity, these activities were more similar in Colo-320 cells which were treated with Northern Cyprus almond oil. DISCUSSION AND CONCLUSION: Almond oil from Northern Cyprus and Turkey may have anticancer and antiproliferative effects on colon cancer cells through molecular signalling pathways and, thus, they could be potential novel therapeutic agents.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Neoplasias do Colo/patologia , Ácidos Graxos/farmacologia , Óleos de Plantas/farmacologia , Prunus dulcis , Sementes , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/uso terapêutico , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Sobrevivência Celular/fisiologia , Neoplasias do Colo/tratamento farmacológico , Relação Dose-Resposta a Droga , Ácidos Graxos/isolamento & purificação , Ácidos Graxos/uso terapêutico , Humanos , Óleos de Plantas/isolamento & purificação , Óleos de Plantas/uso terapêuticoRESUMO
Essential oil extracts from Ferula iliensis have been used traditionally in Kazakhstan for treatment of inflammation and other illnesses. Because little is known about the biologic activity of these essential oils that contributes to their therapeutic properties, we analyzed their chemical composition and evaluated their phagocyte immunomodulatory activity. The main components of the extracted essential oils were (E)-propenyl sec-butyl disulfide (15.7-39.4%) and (Z)-propenyl sec-butyl disulfide (23.4-45.0%). Ferula essential oils stimulated [Ca2+]i mobilization in human neutrophils and activated ROS production in human neutrophils and murine bone marrow phagocytes. Activation of human neutrophil [Ca2+]i flux by Ferula essential oils was dose-dependently inhibited by capsazepine, a TRPV1 channel antagonist, indicating that TRPV1 channels mediate this response. Furthermore, Ferula essential oils stimulated Ca2+ influx in TRPV1 channel-transfected HEK293 cells and desensitized the capsaicin-induced response in these cells. Additional molecular modeling with known TRPV1 channel agonists suggested that the active component is likely to be (Z)-propenyl sec-butyl disulfide. Our results provide a cellular and molecular basis to explain at least part of the beneficial therapeutic properties of FEOs.
Assuntos
Ferula/química , Neutrófilos/imunologia , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Fagócitos/imunologia , Animais , Cálcio/metabolismo , Células Cultivadas , Células HEK293 , Humanos , Camundongos , Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Fagócitos/efeitos dos fármacos , Fagócitos/metabolismo , Canais de Cátion TRPV/metabolismoRESUMO
Essential oils were obtained by hydrodistillation of the umbels+seeds and stems of Ferula akitschkensis (FAEOu/s and FAEOstm, respectively) and analyzed by gas chromatography and gas chromatography-mass spectrometry. Fifty-two compounds were identified in FAEOu/s; the primary components were sabinene, α-pinene, ß-pinene, terpinen-4-ol, eremophilene, and 2-himachalen-7-ol, whereas the primary components of FAEOstm were myristicin and geranylacetone. FAEOu/s, ß-pinene, sabinene, γ-terpinene, geranylacetone, isobornyl acetate, and (E)-2-nonenal stimulated [Ca(2+)]i mobilization in human neutrophils, with the most potent being geranylacetone (EC50 = 7.6 ± 1.9 µM) and isobornyl acetate 6.4 ± 1.7 (EC50 = 7.6 ± 1.9 µM). In addition, treatment of neutrophils with ß-pinene, sabinene, γ-terpinene, geranylacetone, and isobornyl acetate desensitized the cells to N-formyl-Met-Leu-Phe (fMLF)- and interleukin-8 (IL-8)-induced [Ca(2+)]i flux and inhibited fMLF-induced chemotaxis. The effects of ß-pinene, sabinene, γ-terpinene, geranylacetone, and isobornyl acetate on neutrophil [Ca(2+)]i flux were inhibited by transient receptor potential (TRP) channel blockers. Furthermore, the most potent compound, geranylacetone, activated Ca(2+) influx in TRPV1-transfected HEK293 cells. In contrast, myristicin inhibited neutrophil [Ca(2+)]i flux stimulated by fMLF and IL-8 and inhibited capsaicin-induced Ca(2+) influx in TRPV1-transfected HEK293 cells. These findings, as well as pharmacophore modeling of TRP agonists, suggest that geranylacetone is a TRPV1 agonist, whereas myristicin is a TRPV1 antagonist. Thus, at least part of the medicinal properties of Ferula essential oils may be due to modulatory effects on TRP channels.
Assuntos
Ferula/química , Fatores Imunológicos/farmacologia , Neutrófilos/efeitos dos fármacos , Óleos Voláteis/farmacologia , Óleos de Plantas/farmacologia , Aldeídos/farmacologia , Canfanos/farmacologia , Capsaicina/farmacologia , Movimento Celular/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Células HEK293 , Células HL-60 , Humanos , Interleucina-8/metabolismo , N-Formilmetionina Leucil-Fenilalanina/análogos & derivados , N-Formilmetionina Leucil-Fenilalanina/metabolismo , Neutrófilos/metabolismo , Óleos Voláteis/química , Óleos de Plantas/química , Sementes/química , Canais de Cátion TRPV/metabolismo , Terpenos/farmacologia , Canais de Potencial de Receptor Transitório/metabolismoRESUMO
Leaves of Juglans regia L. collected from two different locations [Adana (A) and Ankara (B)] from Turkey were subjected to hydrodistillation in a Clevenger type apparatus to yield the essential oils (EOs). GC/MS and GC-FID analyses revealed that the A EO was rich in thymol (23.1%), while caryophyllene oxide (33.8%) was found as the main constituent of B EO. Both contained P-eudesmol (1.4% - 9.5 %), (E)-geranyl acetone (3.7% - 5.8%) and the eudesmane type constituent juglaterpene A (3.1% - 11.0%). Using a HP Innowax preparative capillary column connected to a preparative fraction collector, an unknown constituent, juglaterpene A (1, 1 l-hydroxy-2,4-cycloeudesmane), was isolated in a rapid one-step manner with > 94.0% purity. Structure determination was accomplished from ID- and 2D-NMR spectroscopic data. Oil B demonstrated significant larvicidal activity against 1st instar Aedes aegypti L.
Assuntos
Inseticidas/química , Juglans/química , Folhas de Planta/química , Óleos de Plantas/química , Sesquiterpenos/química , Aedes , Animais , Cromatografia Gasosa-Espectrometria de Massas , Inseticidas/farmacologia , Larva/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Óleos de Plantas/farmacologia , Sesquiterpenos/farmacologiaRESUMO
The chemical composition and mosquito larvicidal and adulticidal activity of five essential oils (EOs), Dracocephalum ruyschiana L. (DR), D. foetidum Bunge (DF), D. moldavica L. (DM), D. fruticulosum Steph. ex Willd. (DFr) and D. peregrinum L. (DP) were evaluated. Simultaneous GC-FID and GC-MS analyses revealed in the EOs of DR, DF and DM an unidentified compound (1) ([M'122], 5.4%, 57.9% and 74.0%, respectively). Therefore, we aimed to isolate compound 1 using Preparative Capillary GC (PCGC) connected to a Preparative Fraction Collector (PFC) system. Structure determination of 1 was determined by 'H- and 3C-NMR as p-mentha-1,8-dien-10-al (1, limonen-10-al). Other detected major constituents were thymol (34.0%) and carvacrol (6.1%) in DR; limonene (28.8%) in DF; cis-chrysanthenol acetate (29.1%) and trans-verbenol (5.0%) in DFr; and linalool (17.9%), trans-o-bergamotene (7.9%), (E)- nerolidol (7.7%) and eugenol (5.5%) in DP. The DFr, DP, DR and DM EOs produced 100% mortality to 1st instar larvae of Aedes aegypti L. at 250 ppm and DR and DM EO exhibited the strongest activity and killed 100% 1st instar larvae at 62.5 ppm. No adulticidal activity was observed against female Ae. aegypti. In the scope of the present study, for the first time isolation of limonen-I0-al (1) from DR, DM, and DP EOs and larvicidal activity of five Dracocephalum EOs were reported.
Assuntos
Aedes , Inseticidas , Lamiaceae/química , Larva/efeitos dos fármacos , Óleos Voláteis/química , Óleos Voláteis/toxicidade , Animais , Cromatografia Gasosa , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Espectroscopia de Ressonância Magnética , MongóliaRESUMO
Essential oils were obtained by hydrodistillation of the flowers+leaves and stems of Artemisia kotuchovii Kupr. (AKEO(f+l) and AKEO(stm), respectively) and analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The primary components of the oils were estragole, (E)- and (Z)-ß-ocimenes, methyleugenol, limonene, spathulenol, ß-pinene, myrcene, and (E)-methyl cinnamate. Seventy-four constituents were present at concentrations from 0.1 to 1.0%, and 34 compounds were identified in trace (<0.1%) amounts in one or both plant components. Screening of the essential oils for biological activity showed that AKEO(stm), but not AKEOf+l, inhibited N-formyl-Met-Leu-Phe (fMLF)-stimulated Ca(2+) flux and chemotaxis and phorbol-12-myristate-13-acetate (PMA)-induced reactive oxygen species (ROS) production in human neutrophils. Selected pure constituents, representing >96% of the AKEO(stm) composition, were also tested in human neutrophils and HL-60 cells transfected with N-formyl peptide receptor 1 (FPR1). One component, 6-methyl-3,5-heptadien-2-one (MHDO), inhibited fMLF- and interleukin 8 (IL-8)-stimulated Ca(2+) flux, fMLF-induced chemotaxis, and PMA-induced ROS production in human neutrophils. MHDO also inhibited fMLF-induced Ca(2+) flux in FPR1-HL60 cells. These results suggest that MHDO may be effective in modulating some innate immune responses, possibly by inhibition of neutrophil migration and ROS production.
Assuntos
Artemisia/química , Neutrófilos/efeitos dos fármacos , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Óleos de Plantas/farmacologia , Movimento Celular/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Células HL-60 , Humanos , Neutrófilos/citologia , Neutrófilos/imunologia , Óleos Voláteis/química , Extratos Vegetais/química , Folhas de Planta/química , Óleos de Plantas/químicaRESUMO
Gas chromatographic analysis revealed that the oil of Crinitaria tatarica was rich in sabinene (32.1%), ß-pinene (8.8%), and two unknown (M+200) compounds (I) and (II) (21.4% and 3.4%). One-step multiple fractionation of the oil and separation of two unknown constituents were performed using preparative capillary gas chromatography connected to preparative fraction collector system. This combination allowed separation and recover of sufficient quantities of two unknown compounds with high purity from complex oil matrix. Separation conditions (column temperature, cooling temperature, flow rate, injection volume, cut time) were optimized to achieve the best isolation and successful collection. The target compounds were separated from the oil using a HP Innowax (Walt & Jennings Scientific, Wilmington, DE, USA) preparative capillary column in rapid one-step manner with 95.0% purity. Trapping of the isolated compounds in collector system was facilitated by cooling with liquid nitrogen. Structure determination was accomplished by spectral analysis including ultraviolet, nuclear magnetic rezonance, and high-resolution electrospray ionization mass spectrometry. Z- (I) and E-artemidin (II) were isolated for the first time from this species. Crinitaria tatarica oil and Z- (I) and E-artemidin (II) were evaluated for biological activity.
Assuntos
Antifúngicos/isolamento & purificação , Asteraceae/química , Cromatografia Gasosa/métodos , Inseticidas/isolamento & purificação , Óleos de Plantas/isolamento & purificação , Óleos de Plantas/farmacologia , Aedes/efeitos dos fármacos , Animais , Antifúngicos/química , Monoterpenos Bicíclicos , Cromatografia Gasosa/instrumentação , Colletotrichum/efeitos dos fármacos , Inseticidas/química , Monoterpenos , Óleos de Plantas/química , Espectrometria de Massas por Ionização por Electrospray , Análise Espectral/métodosRESUMO
Four different isolation techniques, conventional hydrodistillation (HD), microwave-assisted hydrodistillation (MWHD), microdistillation (MD) and micro-steam distillation-solid-phase microextraction (MSD-SPME), have been used to analyze the volatile constituents from the aerial parts of Salvia rosifolia Sm. by gas chromatography and gas chromatography coupled to mass spectrometry. HD and MWHD techniques produced quantitatively (yield, 0.39% and 0.40%) and qualitatively (aromatic profile) similar essential oils. alpha-Pinene (15.7-34.8%), 1,8-cineole (16.6-25.1%), beta-pinene (6.7-13.5%), beta-caryophyllene (1.4-5.0%) and caryophyllene oxide (1.4-4.4%) were identified as major constituents of this Turkish endemic species. Besides, the hydrodistilled oil of S. rosifolia was evaluated for antibacterial, antifungal, anticancer, antioxidant and cytotoxic activities. The hydrodistilled oil of S. rosifolia showed antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) with a MIC value of 125microg/mL. Other human pathogenic microorganisms (Escherichia coli, Pseudomonas aeruginosa, Enterobacter aerogenes, Salmonella typhimurium, Staphylococcus epidermidis, Candida albicans) were also inhibited within a moderate range (MIC=125-1000microg/mL). Antifungal activity of the oil was also observed against the strawberry anthracnose-causing fungal plant pathogens Colletotrichum acutatum, C. fragariae and C. gloeosporioides. No cytotoxicity was observed for S. rosifolia oil up to 25mg/mL against malignant melanoma, epidermal, ductal and ovary carcinoma.
Assuntos
Bactérias/efeitos dos fármacos , Destilação/métodos , Cromatografia Gasosa-Espectrometria de Massas/métodos , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/farmacologia , Salvia/química , Animais , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Colletotrichum/efeitos dos fármacos , Humanos , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Componentes Aéreos da Planta/química , Extratos Vegetais/química , Microextração em Fase Sólida/métodosRESUMO
Bioassay-guided fractionation of the chloroform extract from the roots of Angelica sinensis led to isolation and characterization of (Z)-ligustilide using direct-bioautography with Colletotrichum species. The structure of (Z)-ligustilide was confirmed by (1)H and (13)C NMR spectroscopy and GC/MS. (Z)-Ligustilide deterred the biting of two mosquito species more effectively than DEET. Three different A. sinensis accessions and one Angelica archangelica root oil were evauated by GC and GC/MS, and the dominant component in A. sinensis was 61-69% (Z)-ligustilide. Two other prominent compounds in A. sinensis oils were 5.7-9.8% (E)-3-butylidene phthalide and 1.5-2.3% (Z)-3-butylidene phthalide. The main constituents that comprised A. archangelica oil were monoterpene hydrocarbons such as 24.5% alpha-pinene, 13.8% delta-3-carene, 10.1% beta-phellandrene, 8.8% p-cymene, 8.4% limonene, and 6.3% sabinene. Phthalides and monoterpene hydrocarbons were determined to be good systematic markers or chemical fingerprints for A. sinensis and A. archangelica root oils. Chemical fingerprinting by GC/MS of A. sinensis also confirmed the misidentification of one A. archangelica sample sold in the Chinese market.