Compounds isolated from botanical sources represent innovative and promising alternatives to conventional insecticides. Carlina oxide is a compound isolated from Carlina acaulis L. (Asteraceae) essential oil (EO) with great potential as bioinsecticide, being effective on various arthropod vectors and agricultural pests, with moderate toxicity on non-target species. Since the production from the wild source is limited, there is the need of exploring new synthetic routes for obtaining this compound and analogues with improved bioactivity and lower toxicity. Herein, the chemical synthesis of carlina oxide analogues was developed. Their insecticidal activity was assessed on the vectors Musca domestica L. and Culex quinquefasciatus Say, and their cytotoxicity was evaluated on a human keratinocyte cell line (HaCaT). The compounds' activity was compared with that of the natural counterparts EO and carlina oxide. In housefly tests, the analogues were comparably effective to purified carlina oxide. In Cx. quinquefasciatus assays, the meta-chloro analogue provided a significantly higher efficacy (LC50 of 0.71 μg mL-1) than the EO and carlina oxide (LC50 1.21 and 1.31 μg mL-1, respectively) and a better safety profile than carlina oxide on keratinocytes. Overall, this study can open the way to an agrochemical production of carlina oxide analogues employable as nature-inspired insecticides.
- MeSH
- Asteraceae * chemie MeSH
- Culex * MeSH
- insekticidy * farmakologie MeSH
- komáří přenašeči MeSH
- larva MeSH
- lidé MeSH
- oleje prchavé * farmakologie chemie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Essential oils can be used in a variety of ways to treat microorganisms that have evolved antibiotic resistance. The research assessed the antimicrobial and antioxidant activities of essential oil obtained from Citrus Limonum, Citrus reticulate, and Citrus sinensis fresh peels using the hydro-distillation method. Their chemical compositions were analyzed by Gas Chromatography-Mass Spectrometer. Citrus oils had antimicrobial and antioxidant properties and their activity was increased with increasing concentrations. Oils had a significant antimicrobial effect on tested bacteria except on P. aeruginosa only C. Limonum had significant (p≤0.05) inhibitory effects at both 100 and 200 mg/ml. There was no significant (p>0.05) difference in the inhibition zone of tested oils against A. baumannii and ciprofloxacin at 25 mg/ml, which was the same as against E. coli at 200 mg/ml. The oil inhibitory effect on K. pneumoniae, P. mirabilis, and S. aureus was less than that obtained from ciprofloxacin at concentrations used. At 100 mg/mL, C. reticulate oil had a 23 mm inhibitory zone, while C. sinensis oil had a 23 mm inhibitory zone at 200 mg/mL, which was the same as the inhibitory area of ciprofloxacin against S. marcescens. Oils had convergent antifungal activity against Candida albicans that increased with increasing concentrations. The extracts competed favorably with voriconazole being used as a positive control. Citrus oils had convergent scavenging activities at the concentrations used. The studies confirmed the medicinal and industrial use of citrus essential oils as a therapeutic and antioxidant agent.
- MeSH
- antifungální látky analýza chemie farmakologie MeSH
- antiinfekční látky analýza chemie farmakologie MeSH
- antioxidancia analýza chemie farmakologie MeSH
- biomedicínský výzkum MeSH
- chemické techniky analytické metody přístrojové vybavení MeSH
- Citrus * chemie MeSH
- destilace metody přístrojové vybavení MeSH
- epidermis rostlin chemie MeSH
- farmakologické účinky MeSH
- fytonutrienty analýza chemie farmakologie MeSH
- oleje prchavé * analýza chemie farmakologie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- scavengery volných radikálů MeSH
- Geografické názvy
- Irák MeSH
As a component of drinks, food, cosmetics, and spice, hops yields a plethora of biologically active compounds. This plant, which was valued by gods and kings through the history, may serve as a basis for pharmaceutical ex-ploitation: not only as a healthy folk medicine but also in asearch for the effective sedative, estrogenic, antimicro-bial, antidiabetic, and cancerostatic compounds.Full text English translation is available in the on-line version.
- MeSH
- Humulus * chemie MeSH
- léčivé rostliny chemie MeSH
- oleje prchavé chemie MeSH
- pivo MeSH
- tradiční lékařství MeSH
- Publikační typ
- přehledy MeSH
As a component of drinks, food, cosmetics, and spice, hops yields a plethora of biologically active compounds. This plant, which was valued by gods and kings through the history, may serve as a basis for pharmaceutical ex-ploitation: not only as a healthy folk medicine but also in asearch for the effective sedative, estrogenic, antimicro-bial, antidiabetic, and cancerostatic compounds.
- MeSH
- Humulus * chemie MeSH
- léčivé rostliny chemie MeSH
- oleje prchavé chemie MeSH
- pivo MeSH
- tradiční lékařství MeSH
- Publikační typ
- přehledy MeSH
α-Terpineol, terpinen-4-ol, and δ-terpineol, isomers of terpineol, are among the compounds that give Cinnamomum longepaniculatum leaf oil its distinguished pleasant smell. The objective of this study was to evaluate the antimicrobial activity of these three isomeric terpineols. The determination of antibacterial activity was based on the minimum inhibition concentration (MIC) and minimum bactericide concentration (MBC). Changes in time-kill curve, alkaline phosphatase (AKP), UV-absorbing material, membrane potential, and scanning electron microscopy (SEM) were measured to elucidate the possible antimicrobial mechanism. α-Terpineol, terpinen-4-ol, and δ-terpineol demonstrated good inhibitory effects against several gram-negative bacteria, particularly Shigella flexneri. MIC and MBC of α-terpineol and terpinen-4-ol were similar (0.766 mg/mL and 1.531 mg/mL, respectively) for S. flexneri, while the MIC and MBC values of δ-terpineol were 0.780 mg/mL and 3.125 mg/mL, respectively. Time-kill curves showed that the antibacterial activities of the tested compounds were in a concentration-dependent manner. Release of nucleic acids and proteins along with a decrease in membrane potential proved that α-terpineol, terpinen-4-ol, and δ-terpineol could increase the membrane permeability of Shigella flexneri. Additionally, the release of AKP suggested that the cell wall was destroyed. SEM analysis further confirmed that S. flexneri cell membranes were damaged by α-terpineol, terpinen-4-ol, and δ-terpineol. Our research suggests that these three isomeric terpineols have the potential of being used as natural antibacterial agents by destroying the cell membrane and wall, resulting in cell death. However, the specific antibacterial activity differences need further investigation.
- MeSH
- antibakteriální látky chemie farmakologie MeSH
- buněčná stěna účinky léků MeSH
- gramnegativní bakterie účinky léků MeSH
- isomerie MeSH
- listy rostlin chemie MeSH
- membránové potenciály účinky léků MeSH
- mikrobiální testy citlivosti MeSH
- oleje prchavé chemie farmakologie MeSH
- skořicovník chemie MeSH
- terpeny chemie farmakologie MeSH
- Publikační typ
- časopisecké články MeSH
The chemical composition, and antioxidant activity of the essential oils of the endemic Phlomis leucophracta P. H. Davis et Hub.-Mor. was investigated. The major compounds of the essential oil were linalool (36.4%), spathulenol (8.4%) and caryophyllene oxide (8.4%). The composition of the oil differs with published data, suggesting other chemotype. Moreover, the oil of this species was analysed for its antioxidant activity for the first time and results indicate it possess strong antioxidant activity comparable with already known antioxidants, such as ascorbic acid, BHT, or Trolox. Presented results suggest that this endemic species has strong potential to be used in food and pharmacological industries, and therefore they need to be further investigated.
- MeSH
- acyklické monoterpeny analýza MeSH
- antioxidancia * farmakologie MeSH
- oleje prchavé chemie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- polycyklické seskviterpeny analýza MeSH
- sápa chemie MeSH
- seskviterpeny analýza MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Turecko MeSH
Essential oils obtained via the hydrodistillation of two Asian herbs (Houttuynia cordata and Persicaria odorata) were analyzed by gas chromatography coupled to mass spectrometry (GC-MS) and gas chromatography with flame ionization detector (GC-FID). Additionally, both the liquid and vapor phase of essential oil were tested on antimicrobial activity using the broth microdilution volatilization method. Antimicrobial activity was tested on Gram-negative and Gram-positive bacteria-Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Enterococcus faecalis, Streptococcus pyogenes, Klebsiella pneumoniae, Seratia marcescense and Bacillus subtilis. Hydrodistillation produced a yield of 0.34% (Houttuynia cordata) and 0.40% (Persicaria odorata). 41 compounds were identified in both essential oils. Essential oils contained monoterpenes and their oxidized forms, sesquiterpenes and their oxidized forms, oxidized diterpenes, derivates of phenylpropene and other groups, such as, for example, aldehydes, alcohols or fatty acids. Both essential oils were antimicrobial active in both vapor and liquid phases at least in case of one bacterium. They expressed various antimicrobial activity in the range of 128-1024 μg∙mL-1, 512-1024 μg∙mL-1 in broth and 1024 μg∙mL-1, 512-1024 μg∙mL-1 in agar, respectively. Research showed new interesting information about P. odorata and H. cordata essential oils and demonstrated that both essential oils could be possibly used in the field of natural medicine or natural food preservation.
- MeSH
- antibakteriální látky chemie farmakologie MeSH
- bakteriální infekce farmakoterapie mikrobiologie MeSH
- extrakce kapalina-kapalina MeSH
- grampozitivní bakterie účinky léků MeSH
- Houttuynia chemie MeSH
- lidé MeSH
- mikrobiální testy citlivosti MeSH
- oleje prchavé chemie farmakologie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- Polygonaceae chemie MeSH
- rostlinné extrakty chemie farmakologie MeSH
- Staphylococcus aureus účinky léků patogenita MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
Dyslipidemias are lipid metabolism alterations that cause increased levels of serum lipoprotein, cholesterol, and triglycerides. These alterations are associated with a higher incidence of cardiovascular diseases and are a risk factor for atherosclerosis development. This study aimed to evaluate the effect of Rosmarinus officinalis essential oil (EORO, 100 mg/kg) and its nanoemulsion (NEORO, 500 µg/kg) on Triton and coconut saturated-fat-induced (CSF) dyslipidemias using Wistar rats. The phytochemical evaluation of EORO performed by gas chromatography-mass spectroscopy (GC-MS) revealed 1,8-cineole (33.70%), camphor (27.68%), limonene (21.99%), and α-pinene (8.13%) as its major compounds. Triton-induced dyslipidemia significantly increased total cholesterol, LDL, and triglycerides levels. On the other hand, the groups treated with EORO and NEORO had significantly reduced total cholesterol, LDL, and triglycerides compared to the group treated only with Triton. Similar results were observed on the positive control treated with simvastatin. Dyslipidemia induced with coconut saturated-fat (CSF) caused abdominal fat gain, hypercholesterolemia, hypertriglyceridemia, increased LDL levels, and atherogenesis in the aorta. In contrast, the groups treated with EORO, NEORO, and simvastatin had significantly reduced hypercholesterolemia and hypertriglyceridemia, reduced abdominal fat gain, and absence of atherogenesis in the vascular endothelium. Overall, in the Triton-induced dyslipidemia model, EORO treatment had superior values than NEORO's (and simvastatin), although the differences were not too high, while in the CSF model, the values were mixed. In this manner, our results show an anti-dyslipidemic and anti-atherogenic activity effect by EORO and NEORO.
- Klíčová slova
- nanoemulze,
- MeSH
- aorta thoracica diagnostické zobrazování patologie MeSH
- ateroskleróza farmakoterapie komplikace MeSH
- chromatografie statistika a číselné údaje MeSH
- dyslipidemie * farmakoterapie komplikace MeSH
- mikroskopie elektronová rastrovací MeSH
- modely u zvířat MeSH
- nanostruktury statistika a číselné údaje terapeutické užití MeSH
- oleje prchavé * analýza aplikace a dávkování chemie MeSH
- potkani Wistar MeSH
- rozmarýn MeSH
- simvastatin terapeutické užití MeSH
- tuky škodlivé účinky MeSH
- výsledek terapie MeSH
- Publikační typ
- klinická studie MeSH
- práce podpořená grantem MeSH
Comprehensive oncology research suggests an important role of phytochemicals or whole plant foods in the modulation of signaling pathways associated with anticancer action. The goal of this study is to assess the anticancer activities of Cinnamomum zeylanicum L. using rat, mouse, and cell line breast carcinoma models. C. zeylanicum (as bark powder) was administered in the diet at two concentrations of 0.1% (w/w) and 1% (w/w) during the whole experiment in chemically induced rat mammary carcinomas and a syngeneic 4T1 mouse model. After autopsy, histopathological and molecular evaluations of mammary gland tumors in rodents were carried out. Moreover, in vitro analyses using MCF-7 and MDA-MB-231 cells were performed. The dominant metabolites present in the tested C. zeylanicum essential oil (with relative content over 1%) were cinnamaldehyde, cinnamaldehyde dimethyl acetal, cinnamyl acetate, eugenol, linalool, eucalyptol, limonene, o-cymol, and α-terpineol. The natural mixture of mentioned molecules demonstrated significant anticancer effects in our study. In the mouse model, C. zeylanicum at a higher dose (1%) significantly decreased tumor volume by 44% when compared to controls. In addition, treated tumors showed a significant dose-dependent decrease in mitotic activity index by 29% (0.1%) and 45.5% (1%) in comparison with the control group. In rats, C. zeylanicum in both doses significantly reduced the tumor incidence by 15.5% and non-significantly suppressed tumor frequency by more than 30% when compared to controls. An evaluation of the mechanism of anticancer action using valid oncological markers showed several positive changes after treatment with C. zeylanicum. Histopathological analysis of treated rat tumor specimens showed a significant decrease in the ratio of high-/low-grade carcinomas compared to controls. In treated rat carcinomas, we found caspase-3 and Bax expression increase. On the other hand, we observed a decrease in Bcl-2, Ki67, VEGF, and CD24 expressions and MDA levels. Assessment of epigenetic changes in rat tumor cells in vivo showed a significant decrease in lysine methylation status of H3K4m3 and H3K9m3 in the high-dose treated group, a dose-dependent increase in H4K16ac levels (H4K20m3 was not changed), down-regulations of miR21 and miR155 in low-dose cinnamon groups (miR22 and miR34a were not modulated), and significant reduction of the methylation status of two out of five gene promoters-ATM and TIMP3 (PITX2, RASSF1, PTEN promoters were not changed). In vitro study confirmed results of animal studies, in that the essential oil of C. zeylanicum displayed significant anticancer efficacy in MCF-7 and MDA-MB-231 cells (using MTS, BrdU, cell cycle, annexin V/PI, caspase-3/7, Bcl-2, PARP, and mitochondrial membrane potential analyses). As a conclusion, C. zeylanicum L. showed chemopreventive and therapeutic activities in animal breast carcinoma models that were also significantly confirmed by mechanistic evaluations in vitro and in vivo.
- MeSH
- antitumorózní látky fytogenní aplikace a dávkování chemie farmakologie MeSH
- histony metabolismus MeSH
- krysa rodu rattus MeSH
- kůra rostlin chemie MeSH
- lidé MeSH
- MFC-7 buňky MeSH
- mikro RNA genetika MeSH
- myši MeSH
- nádorové buněčné linie MeSH
- nádory prsu farmakoterapie genetika metabolismus MeSH
- oleje prchavé aplikace a dávkování chemie farmakologie MeSH
- oleje rostlin aplikace a dávkování chemie farmakologie MeSH
- proliferace buněk účinky léků MeSH
- skořicovník ceylonský chemie MeSH
- viabilita buněk účinky léků MeSH
- vztah mezi dávkou a účinkem léčiva MeSH
- xenogenní modely - testy antitumorózní aktivity MeSH
- zvířata MeSH
- Check Tag
- krysa rodu rattus MeSH
- lidé MeSH
- myši MeSH
- ženské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
Terpenoids, one of the major components of essential oils, are known to exert potent antifungal activity against yeast Saccharomyces cerevisiae. They have been the subject of a considerable number of investigations that uncovered extensive pharmacological properties, including antifungal and antibacterial effects. However, their mechanism of action remains elusive. In order to use terpenoids as the antimicrobial and antifungal agents in food preservation in a rational way, a good knowledge of their mode of action is required. We hypothesized that the cellular membrane is the main target site for the antifungal agents, and that structural properties of these agents are key to penetrate and act upon phospholipid bilayers. In this study, we thus aimed to study the effect of terpenoids on the cell membrane integrity, with the focus on both their structural properties, such as the presence of aromatic ring or hydroxyl group; and their hydrophobicity, as a consequence of these structural features. We first uncovered the antifungal properties of phenolic terpenoids thymol, carvacrol and eugenol, cyclic terpenes limonene, carveol, and α-pinene, in addition to the closely related compounds of different chemical structures. We then examined the cell membrane deterioration upon the addition of these reagents. Our results demonstrate that the presence of a phenolic -OH moiety is crucial, and hydrophobicity gained by the aromatic ring structure contributes to the ability of penetration and damaging yeast plasma membrane to achieve high antifungal activity.
- MeSH
- antifungální látky chemie farmakologie MeSH
- buněčná membrána účinky léků metabolismus MeSH
- hydrofobní a hydrofilní interakce MeSH
- mikrobiální testy citlivosti MeSH
- molekulární struktura MeSH
- oleje prchavé chemie farmakologie MeSH
- permeabilita buněčné membrány účinky léků MeSH
- Saccharomyces cerevisiae účinky léků metabolismus MeSH
- terpeny chemie farmakologie MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Publikační typ
- časopisecké články MeSH
