Natural products are widely used in different aspects of our lives - from household cleaners and food production, via cosmetics and aromatherapy, to both alternative and traditional medicine. In our research group, we have recently described several monoterpenoids with potential in the antiviral and anticancer therapy by allosteric targeting of aryl hydrocarbon receptor (AhR). Prior to any practical application, biological effects on human organism must be taken in concern. This review article is focused on the biological effects of 5 monoterpenoids on the human health previously identified as AhR antagonists with a therapeutic potential as antiviral and anticancer agents. We have thoroughly described cytotoxic, anti-inflammatory, anti-proliferative, and anticancer effects, as well as known interactions with nuclear receptors. As clearly demonstrated, monoterpenoids in general represent almost an inexhaustible reservoir of natural compounds possessing the ability to influence, modulate and improve human health.
- MeSH
- antitumorózní látky farmakologie terapeutické užití MeSH
- antivirové látky farmakologie terapeutické užití chemie MeSH
- lidé MeSH
- monoterpeny * farmakologie chemie terapeutické užití MeSH
- nádory farmakoterapie metabolismus MeSH
- receptory aromatických uhlovodíků * metabolismus MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- přehledy MeSH
In this review, we collected and presented evidence from the scientific literature regarding the biotechnological production and applications of limonene and its oxidative derivates in various fields such as food, pharmaceutical, cosmetic or polymer industries. Limonene biotransfor-mations may be regarded as biotechnological processes aligned to sustainable development. Advantages associated with these bioprocesses include the use of by-products as raw materials, mild reaction conditions, high regio-and stereoselectivity and the production of value-added prod-ucts. The biological activities of limonene and its oxidative derivates, such as carveol, carvone, limonene-1,2-diol, α-terpineol, or perillyl alcohol, suggest that the terpene biotechnology is becoming a promising and prosperous science.
Skin penetration/permeation enhancers are compounds that improve (trans)dermal drug delivery. We designed hybrid terpene-amino acid enhancers by conjugating natural terpenes (citronellol, geraniol, nerol, farnesol, linalool, perillyl alcohol, menthol, borneol, carveol) or cinnamyl alcohol with 6-(dimethylamino)hexanoic acid through a biodegradable ester linker. The compounds were screened for their ability to increase the delivery of theophylline and hydrocortisone through and into human skin ex vivo. The citronellyl, bornyl and cinnamyl esters showed exceptional permeation-enhancing properties (enhancement ratios up to 82) while having low cellular toxicities. The barrier function of enhancer-treated skin (assessed by transepidermal water loss and electrical impedance) recovered within 24 h. Infrared spectroscopy suggested that these esters fluidized the stratum corneum lipids. Furthermore, the citronellyl ester increased the epidermal concentration of topically applied cidofovir, which is a potent antiviral and anticancer drug, by 15-fold. In conclusion, citronellyl 6-(dimethylamino)hexanoate is an outstanding enhancer with an advantageous combination of properties, which may improve the delivery of drugs that have a limited ability to cross biological barriers.
- MeSH
- alkoholy chemie farmakologie MeSH
- aplikace kožní MeSH
- buňky 3T3 MeSH
- chemie farmaceutická MeSH
- cidofovir aplikace a dávkování chemie farmakokinetika MeSH
- epidermis účinky léků metabolismus MeSH
- estery chemie farmakologie MeSH
- farmaceutické pomocné látky chemie farmakologie MeSH
- hydrokortison aplikace a dávkování chemie farmakokinetika MeSH
- keratinocyty MeSH
- lidé MeSH
- metabolismus lipidů účinky léků MeSH
- monoterpeny chemie MeSH
- myši MeSH
- permeabilita účinky léků MeSH
- perspiratio insensibilis účinky léků MeSH
- příprava léků metody MeSH
- terpeny chemie farmakologie MeSH
- testy akutní toxicity MeSH
- theofylin aplikace a dávkování chemie farmakokinetika MeSH
- vztahy mezi strukturou a aktivitou MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Bark beetles kill apparently vigorous conifers during epidemics by means of pheromone-mediated aggregation. During non-endemic conditions the beetles are limited to use trees with poor defense, like wind-thrown. To find olfactory cues that help beetles to distinguish between trees with strong or weak defense, we collected volatiles from the bark surface of healthy felled or standing Picea abies trees. Furthermore, living trees were treated with methyl jasmonate in order to induce defense responses. Volatiles were analyzed by combined gas chromatography and electroantennographic detection (GC-EAD) on Ips typographus antennae. Compounds eliciting antennal responses were characterized by single sensillum recording for identification of specific olfactory sensory neurons (OSN). Release of monoterpene hydrocarbons decreased, while oxygenated compounds increased, from spring to early summer in felled trees. In both beetle sexes particular strong EAD activity was elicited by trace amounts of terpene alcohols and ketones. 4-Thujanol gave a very strong response and the absolute configuration of the tested natural product was assigned to be (+)-trans-(1R,4S,5S)-thujanol by stereoselective synthesis and enantioselective gas chromatography. One type of OSN responded to all ketones and five other OSN were characterized by the type of compounds that elicited responses. Three new OSN classes were found. Of the eight EAD-active compounds found in methyl jasmonate-treated bark, the known anti-attractant 1,8-cineole was the one most strongly induced. Our data support the hypothesis that highly active oxygenated host volatiles could serve as positive or negative cues for host selection in I. typographus and in other bark beetles.
- MeSH
- acetáty farmakologie MeSH
- brouci fyziologie MeSH
- cyklopentany farmakologie MeSH
- elektrofyziologické jevy účinky léků MeSH
- kůra rostlin chemie účinky léků metabolismus MeSH
- monoterpeny chemická syntéza chemie farmakologie MeSH
- oxylipiny farmakologie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- smrk chemie metabolismus MeSH
- stereoizomerie MeSH
- styren chemie farmakologie MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
Every year Chile exports about 2000 tons of boldo folium (Peumus boldus), which is used around the world as a traditional herbal medicinal product (THMP), mostly to relieve gastrointestinal disorders. This biomass may be a resource for the agrochemical industry to manufacture botanical insecticides. In this regard, the insecticidal potential of boldo has been poorly investigated. In the present work, hydrodistillation of a commercial boldo folium gave 1.5% (w/w) of a yellowish essential oil (boldo essential oil, BEO) containing 1,8-cineole (20.7%), p-cymene (18.5%), limonene (9.1%), ascaridole (9.1%) and β-phellandrene (6.4%) as the main constituents, as determined by gas chromatography-mass spectrometry (GC-MS). NMR analysis allowed us to determine that ascaridole was mainly represented by the cis-isomer. BEO was toxic to larvae of the filariasis vector Culex quinquefasciatus and adults of the housefly Musca domestica, showing LC50/LD50 values of 67.9 mg·L-1 and 98.5 µg·adult-1, respectively. On the other hand, lower insecticidal activity was observed against larvae of the moth pest Spodoptera littoralis (LD50 of 268.9 µg·larva-1). It is worth noting that, when tested at LC90 concentration, BEO was significantly less toxic to aquatic microcrustacean Daphnia magna than the conventional insecticide α-cypermethrin. Finally, in the attempt to explore the BEO mode of action, we tested it for acetylcholinesterase (AChE) inhibitory properties using the Ellman method, obtaining negligible effects (IC50 = 0.45 mg·mL-1). Taken together, these results gave new insights into the potential of BEO as a future ingredient of botanical insecticides.
- MeSH
- Culex účinky léků MeSH
- cyklohexeny chemie MeSH
- Daphnia účinky léků MeSH
- insekticidy chemie farmakologie MeSH
- komáří přenašeči účinky léků MeSH
- larva účinky léků MeSH
- LD50 MeSH
- lidé MeSH
- monoterpeny chemie MeSH
- moucha domácí účinky léků MeSH
- můry účinky léků MeSH
- oleje prchavé chemie farmakologie MeSH
- peroxidy chemie MeSH
- Peumus chemie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- pyrethriny chemie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
In the attempt to exploit the potential of the monoecious fiber hemp cv. Futura 75 in new fields besides textile, cosmetics and food industry, its crop-residue given by leaves and inflorescences was subjected to hydrodistillation to obtain the essential oils. These are niche products representing an ideal candidate for the development of natural insecticides for the control and management of mosquito vectors, houseflies and moth pests. After GC-MS analysis highlighting a safe and legal chemical profile (THC in the range 0.004-0.012% dw), the leaf and inflorescence essential oils were investigated for the insecticidal potential against three insect targets: the larvae of Culex quinquefasciatus and Spodoptera littoralis and the adults of Musca domestica. The essential oil from inflorescences, showing (E)-caryophyllene (21.4%), myrcene (11.3%), cannabidiol (CBD, 11.1%), α-pinene (7.8%), terpinolene (7.6%), and α-humulene (7.1%) as the main components, was more effective than leaf oil against these insects, with LD50 values of 65.8 μg/larva on S. littoralis, 122.1 μg/adult on M. domestica, and LC50 of 124.5 μl/l on C. quinquefasciatus larvae. The hemp essential oil moderately inhibited the acetylcholinesterase (AChE), which is a target enzyme in pesticide science. Overall, these results shed light on the future application of fiber hemp crop-residue for the development of effective, eco-friendly and sustainable insecticides.
- MeSH
- alkeny chemie MeSH
- Cannabis chemie MeSH
- Culex účinky léků MeSH
- insekticidy chemie MeSH
- larva účinky léků MeSH
- monoterpeny chemie MeSH
- moucha domácí chemie MeSH
- odpadní produkty MeSH
- oleje prchavé chemie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- seskviterpeny chemie MeSH
- Spodoptera účinky léků MeSH
- terpeny chemie MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
Helichrysum faradifani (Asteraceae) is a perennial shrub growing in rocky and sandy places of Madagascar. The plant is used in the Malagasy traditional medicine as a wound-healing agent, disinfectant and for the treatment of syphilis, diarrhea, cough and headache. In the present work, we analysed the chemical composition of the essential oil distilled from the aerial parts of H. faradifani by GC-MS and evaluated its insecticidal activity against 2nd, 3rd and 4th instar larvae of the lymphatic filariasis vector Culex quinquefasciatus by acute toxicity assays. The most sensitive were 2nd instar (LC50 = 85.7 μL L-1) larvae. For the 3rd and 4th instar larvae, the estimated LC50 were 156.8 and 134.1 μL L-1, respectively. Monoterpene hydrocarbons (51.6%) were the major fraction of the essential oil, with the bicyclic α-fenchene (35.6%) as the predominant component. Sesquiterpene hydrocarbons (34.0%) were the second major group characterising the oil, with γ-curcumene (17.7%) as the most abundant component.
- MeSH
- Culex účinky léků MeSH
- Helichrysum chemie MeSH
- insekticidy chemie farmakologie MeSH
- komáří přenašeči účinky léků MeSH
- larva účinky léků MeSH
- monoterpeny analýza chemie MeSH
- nadzemní části rostlin chemie MeSH
- oleje prchavé chemie farmakologie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- rostlinné extrakty chemie MeSH
- seskviterpeny analýza chemie MeSH
- testy akutní toxicity MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Madagaskar MeSH
Dysphania ambrosioides (L.) Mosyakin & Clemants (Amaranthaceae) and Clausena anisata (Willd.) Hook. f. ex Benth. (Rutaceae) are two aromatic species traditionally used in Cameroon to repel and kill insects. The present work was carried out to substantiate this traditional use and to evaluate the possible incorporation in commercial botanical insecticides of their essential oils (EOs). The EOs were distilled from leaves of C. anisata and aerial parts of D. ambrosioides and analyzed by gas chromatography-mass spectrometry (GC-MS). The insecticidal activity of both EOs was investigated against the filariasis vector, Culex quinquefasciatus, and the housefly, Musca domestica. As possible mode of action, the inhibition of acetylcholinesterase (AChE) by the two EOs was investigated as well. The D. ambrosioides EO was characterized by the monoterpene peroxide ascaridole (61.4%) and the aromatic p-cymene (29.0%), whereas the C. anisata EO was dominated by the phenylpropanoids (E)-anethole (64.6%) and (E)-methyl isoeugenol (16.1%). The C. anisata EO proved to be very toxic to third instar larvae of C. quinquefasciatus showing LC50 of 29.3 μl/l, whereas D. ambrosioides EO was more toxic to adults of M. domestica showing a LD50 of 51.7 μg/adult. The mixture of both EOs showed a significant synergistic effect against mosquito larvae with LC50 estimated as 19.3 μl/l, whereas this phenomenon was not observed upon application to M. domestica adults (LD50 = 75.9 μg/adult). Of the two EOs, the D. ambrosioides one provided a good inhibition of AChE (IC50 = 77 μg/ml), whereas C. anisata oil was not effective. These findings provide new evidences supporting the ethno-botanical use of these two Cameroonian plants, and their possible application even in synergistic binary blends, to develop new eco-friendly, safe and effective herbal insecticides.
- MeSH
- Clausena chemie MeSH
- Culex účinky léků MeSH
- insekticidy analýza MeSH
- komáří přenašeči MeSH
- larva účinky léků MeSH
- listy rostlin chemie MeSH
- monoterpeny chemie MeSH
- moucha domácí účinky léků MeSH
- oleje prchavé chemie MeSH
- peroxidy chemie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Kamerun MeSH
Public interest in natural therapies has increased significantly over past decades. Herbs and herbal products are extensively consumed worldwide and they are generally considered as safe. However, this may not always be true as many cases of herb-induced liver injury are reported every year. The liver is a frequent target tissue of toxicity from all classes of toxicants as liver structure and function predispose it to high sensitivity to xenobiotics. The present review is focused on the hepatotoxic properties of monoterpenes and sesquiterpenes, plant secondary metabolites that represent the major components of essential oils wildly used in folk medicines, pharmaceutical industry and cosmetics. Most of these terpenes easily enter the human body by oral absorption, penetration through the skin, or inhalation leading to measurable blood concentrations. Several studies showed that some monoterpenes (e.g., pulegone, menthofuran, camphor, and limonene) and sesquiterpenes (e.g., zederone, germacrone) exhibited liver toxicity, which is mainly based on reactive metabolites formation, increased concentration of reactive oxygen species and impaired antioxidant defense. There is a high probability that many other terpenes, without sufficiently known metabolism and effects in human liver, could also exert hepatotoxicity. Especially terpenes, that are important components of essential oils with proved hepatotoxicity, should deserve more attention. Intensive research in terpenes metabolism and toxicity represent the only way to reduce the risk of liver injury induced by essential oils and other terpenes-containing products.
- MeSH
- játra účinky léků metabolismus MeSH
- lékové postižení jater etiologie MeSH
- lidé MeSH
- monoterpeny chemie toxicita MeSH
- oleje prchavé chemie toxicita MeSH
- reaktivní formy kyslíku metabolismus MeSH
- rostliny chemie metabolismus MeSH
- seskviterpeny chemie toxicita MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- přehledy MeSH
With aim to develop effective proof-of-concept approach which can be used in a development of new preparations for the inhalation therapy, we designed a new screening method for simple and rapid simultaneous determination of antibacterial potential of plant volatiles in the liquid and the vapour phase at different concentrations. In addition, EVA (ethylene vinyl acetate) capmat™ as vapour barrier cover was used as reliable modification of thiazolyl blue tetrazolium bromide (MTT) assay for cytotoxicity testing of volatiles on microtiter plates. Antibacterial activity of carvacrol, cinnamaldehyde, eugenol, 8-hydroxyquinoline, thymol and thymoquinone was determined against Haemophilus influenzae, Staphylococcus aureus, and Streptococcus pneumoniae using new broth microdilution volatilization method. The cytotoxicity of these compounds was evaluated using MTT test in lung fibroblast cells MRC-5. The most effective antibacterial agents were 8-hydroxyquinoline and thymoquinone with the lowest minimum inhibitory concentrations (MICs) ranging from 2 to 128μg/mL, but they also possessed the highest toxicity in lung cell lines with half maximal inhibitory concentration (IC50) values 0.86-2.95μg/mL. The lowest cytotoxicity effect was identified for eugenol with IC50 295.71μg/mL, however this compound produced only weak antibacterial potency with MICs 512-1024μg/mL. The results demonstrate validity of our novel broth microdilution volatilization method, which allows cost and labour effective high-throughput antimicrobial screening of volatile agents without need of special apparatus. In our opinion, this assay can also potentially be used for development of various medicinal, agricultural, and food applications that are based on volatile antimicrobials.
- MeSH
- akrolein analogy a deriváty chemie MeSH
- antibakteriální látky chemie MeSH
- benzochinony chemie MeSH
- buněčné linie MeSH
- eugenol chemie MeSH
- fytonutrienty chemie MeSH
- Haemophilus influenzae účinky léků MeSH
- lidé MeSH
- mikrobiální testy citlivosti metody MeSH
- monoterpeny chemie MeSH
- oxychinolin chemie MeSH
- Staphylococcus aureus účinky léků MeSH
- Streptococcus pneumoniae účinky léků MeSH
- těkavé organické sloučeniny chemie MeSH
- tetrazoliové soli MeSH
- thiazoly MeSH
- thymol chemie MeSH
- volatilizace * MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
