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Current Opinion in Pharmacology Feb 2022Neurodegenerative diseases (NDDs) are a range of neurological disorders featured by neuronal degeneration and apoptosis. Cellular Calcium (Ca) and reactive oxygen... (Review)
Review
Neurodegenerative diseases (NDDs) are a range of neurological disorders featured by neuronal degeneration and apoptosis. Cellular Calcium (Ca) and reactive oxygen species (ROS) dyshomeostasis are the earliest and important events in the development of NDDs and may yield promising therapeutic targets for NDDs. Paeoniflorin, a water-soluble monoterpene glucoside, is the major bioactive monomer extracted from the root of Paeonia lactiflora pall. Increasing evidence has suggested that this natural compound might be used to treat various NDDs, and its potential molecular mechanisms are related to the modulation of Ca/ROS homeostasis in cells. In addition, paeoniflorin accounts for more than 40% of the total glucosides of herbaceous peonies with abundant herbaceous sources. Furthermore, it has also been validated as a safe extraction in clinical pharmacological research with a wide therapeutic window. Hence, it is rational to anticipate paeoniflorin being a promising candidate for the treatment of NDDs via regulating Ca/ROS dyshomeostasis.
Topics: Glucosides; Homeostasis; Humans; Monoterpenes; Neurodegenerative Diseases; Paeonia; Reactive Oxygen Species
PubMed: 34959127
DOI: 10.1016/j.coph.2021.11.009 -
European Journal of Medicinal Chemistry Sep 2019Carvacrol (CAR), a natural monoterpene particularly abundant in plants belonging to the Lamiaceae family, has recently attracted much attention for its many biological...
Carvacrol (CAR), a natural monoterpene particularly abundant in plants belonging to the Lamiaceae family, has recently attracted much attention for its many biological properties (antioxidant, anti-inflammatory, neuroprotective, antitumour, antibacterial, and several others). However, CAR has poor chemical-physical properties (low water solubility and high volatility), which hamper its potential pharmacological uses. In this paper, the synthesis and antimicrobial evaluation of 23 carvacrol derivatives (WSCP1-23) against a panel of selected gram-positive and gram-negative bacteria are reported. Using the prodrug approach, CAR hydrophilic (WSCP1-17) and lipophilic prodrugs (WSCP18-23) were prepared. Notably, CAR water solubility was increased by using polar neutral groups (such as natural amino acids) with the aim of improving oral drug delivery. On the other hand, CAR lipophilic prodrugs, obtained by prenylation of CAR hydroxyl group, were designed to promote membrane permeation and oral absorption. Our results revealed that WSCP1-3, showing the highest water solubility (>1700-fold compared to that of CAR), possessed good antibacterial activity against gram-negative bacteria with MIC values comparable to those of CAR and antifungal properties against different species of Candida. WSCP18-19 were the most promising prodrugs, showing good antibacterial profiles against gram-positive bacteria by interfering with the biofilm formation of Staphylococcus aureus and Staphylococcus epidermidis. Moreover, WSCP18-19 resulted more stable in simulated fluids and human plasma than WSCP1-3. Toxicity studies performed on human erythrocytes and HaCaT cells revealed that all WSCPs were not toxic at the tested concentrations.
Topics: Anti-Bacterial Agents; Antifungal Agents; Candida; Cymenes; Dose-Response Relationship, Drug; Gram-Negative Bacteria; Gram-Positive Bacteria; Microbial Sensitivity Tests; Molecular Structure; Monoterpenes; Prodrugs; Solubility; Structure-Activity Relationship
PubMed: 31207463
DOI: 10.1016/j.ejmech.2019.05.093 -
Phytomedicine : International Journal... Feb 2022Chronic orofacial pain is a serious public health problem with a prevalence of 7-11% in the population. This disorder has different etiologies and characteristics that...
Limonene, a citrus monoterpene, non-complexed and complexed with hydroxypropyl-β-cyclodextrin attenuates acute and chronic orofacial nociception in rodents: Evidence for involvement of the PKA and PKC pathway.
BACKGROUND
Chronic orofacial pain is a serious public health problem with a prevalence of 7-11% in the population. This disorder has different etiologies and characteristics that make pharmacological treatment difficult. Natural products have been shown to be a promising source of treatments for the management of chronic pain, as an example the terpenes.
PURPOSE
The aim of this study was to evaluate the anti-nociceptive and anti-inflammatory effects of one of these terpenes, d-limonene (LIM - a common monoterpene found in citrus fruits) alone and complexed with hydroxypropyl-β-cyclodextrin (LIM/HPβCD) in preclinical animal models.
METHODS
Orofacial pain was induced by the administration of hypertonic saline on the corneal surface, the injection of formalin into the temporomandibular joint (TMJ), or chronic constriction injury of the infraorbital nerve (CCI-IoN). The study used male Wistar rats and Swiss mice treated with LIM (50 mg/kg), LIM/HPβCD (50 mg/kg), vehicle (control), gabapentin or morphine, and eyes wiping (induced by hypertonic saline), face rubbing (formalin-induced in TMJ) or mechanical hyperalgesia (provoked by CCI-IoN) were assessed. Additionally, ELISA was used to measure TNF-α, and western blot analysis to assess levels of PKAcα, NFκB, p38MAPK and phosphorylated PKC substrates. Serum levels of aspartate aminotransferase (AST) and alanine transferase (ALT) were also evaluated.
RESULTS
LIM and LIM/HPβCD significantly reduced (p < 0.001) corneal nociception and formalin-induced TMJ nociception. In addition, both substances attenuated (p < 0.001) mechanical hyperalgesia in the CCI-IoN model. The antinociceptive effect induced by LIM and HPβCD/LIM was associated with decreased TNF-α levels, downregulation of the NFκB and p38MAPK signalling pathways and reduced PKC substrate phosphorylation and PKA immunocontent. Moreover, the results demonstrated that complexation with HPβCD was able to decrease the therapeutic dose of LIM.
CONCLUSION
LIM was found to be a promising molecule for the treatment of orofacial pain due to its capacity to modulate some important mediators essential to the establishment of pain, and HPβCD can be a key tool to improve the profile of LIM.
Topics: 2-Hydroxypropyl-beta-cyclodextrin; Animals; Citrus; Facial Pain; Hyperalgesia; Limonene; Male; Mice; Monoterpenes; Nociception; Rats; Rats, Wistar; Rodentia
PubMed: 35026511
DOI: 10.1016/j.phymed.2021.153893 -
Biomedicine & Pharmacotherapy =... Oct 2020Australian tea tree (Melaleuca alternifolia) oil (TTO) and its monoterpene constituents such as terpinen-4-ol (T4O), 1,8-cineole, limonene, p-cymene, and α-terpinene... (Review)
Review
Australian tea tree (Melaleuca alternifolia) oil (TTO) and its monoterpene constituents such as terpinen-4-ol (T4O), 1,8-cineole, limonene, p-cymene, and α-terpinene have been shown to be effective in controlling a wide range of parasitic infections. The anti-parasitic effects of these compounds are mainly due to their anti-histamine and anti-acetylcholinesterase activities as well as their ability to modulate host inflammatory responses. This review attempts to summarize recent advances in the uses of TTO and its 15 major monoterpene constituents in treating parasitic infections in both humans and animals. Activities against parasitic protozoans (Plasmodium falciparum, Leishmania spp., Trypanosoma spp., Acanthamoeba castellanii, Trichomonas vaginalis, Eimeria, and Ichthyophthirius multifiliis), nematodes (Haemonchus contortus and Anisakis simplex), cestode (Echinococcus ortleppi), and monogeneans (Gasterosteus spp. and Dactylogyrus minutus) have been reported, showing good potentials in treating parasitic infections. Further studies are necessary for developing anti-parasite therapies using TTO or its monoterpenes constituents.
Topics: Animals; Anti-Infective Agents, Local; Antiprotozoal Agents; Helminthiasis; Humans; Melaleuca; Monoterpenes; Protozoan Infections; Tea Tree Oil
PubMed: 33503761
DOI: 10.1016/j.biopha.2020.110624 -
Yakugaku Zasshi : Journal of the... 2022Olive weevils, Pimelocerus (Dyscerus) perforatus Roelofs, utilize olive trees as a host plant. The adult female uses an elongated snout to puncture the trunk and lay one...
Olive weevils, Pimelocerus (Dyscerus) perforatus Roelofs, utilize olive trees as a host plant. The adult female uses an elongated snout to puncture the trunk and lay one egg a day, resulting in dozens of eggs over its lifetime. The hatched larvae grow by eating the olive trunk. When olive trees die due to feeding damage, olive productivity is seriously impaired. Since there is no effective pesticide for olive weevils so far, the authors aimed to develop a repellent for adult olive weevils from the viewpoint of integrated pest management. We prepared a measurable apparatus for the repellent action against olive weevils and screened chemical substances by using the apparatus. When the repellent activity was measured using vanillin and its derivatives, a clear repellent effect could be confirmed for two types of vanillin derivatives, such as o-vanillin, and 2-hydroxy-4-methoxybenzaldehyde. In addition, when the repellent activity against olive weevils was measured using monoterpenes, four types of acyclic monoterpenes, geraniol, β-citronellol, citral, and linalool, and three types of monocyclic monoterpenes, (-)-limonene, (+)-limonene, and (-)-menthol, and a bicyclic monoterpene, (1R)-(+)-α-pinene, were found to have dose-dependent repellent activity with statistical significance. In the future, it is expected that the formulation for applying the repellent substances to olive trees and the study of their practicality in olive fields will progress.
Topics: Animals; Benzaldehydes; Monoterpenes; Olea; Weevils
PubMed: 36047212
DOI: 10.1248/yakushi.22-00086 -
Environmental Science & Technology Sep 2017We report novel in situ speciated observations of monoterpenes (α- and β-pinene, myrcene, δ3-carene, ocimene, limonene) in seawater and air during three cruises in...
We report novel in situ speciated observations of monoterpenes (α- and β-pinene, myrcene, δ3-carene, ocimene, limonene) in seawater and air during three cruises in the Arctic and Atlantic Oceans, in/over generally oligotrophic waters. Oceanic concentrations of the individual monoterpenes ranged from below the detection limit of <1 pmol L to 5 pmol L, with average concentrations of between 0.5 and 2.9 pmol L. After careful filtering for contamination, atmospheric mixing ratios varied from below the detection limit (<1 pptv) to 5 pptv, with averages of 0.05-5 pptv; these levels are up to 2 orders of magnitude lower than those reported previously. This could be at least partly due to sampling over waters with much lower biological activity than in previous studies. Unlike in previous studies, no clear relationships of the monoterpenes with biological variables were found. Based on our measured seawater concentrations and a global model simulation, we estimate total global marine monoterpene emissions of 0.16 Tg C yr, similar to a previous bottom-up estimate based on laboratory monoculture studies but 2 orders of magnitude lower than a previous top-down estimate of 29.5 Tg C yr.
Topics: Arctic Regions; Atlantic Ocean; Bridged Bicyclo Compounds; Environmental Monitoring; Monoterpenes
PubMed: 28752764
DOI: 10.1021/acs.est.7b02240 -
Recent Advances in Anti-infective Drug... 2023Pulegone ((R)-5-Methyl-2-(1-methylethylidine) cyclohexanone) is a pharmacologically active, natural monoterpene ketone obtained from leaves and flowering tops of the... (Review)
Review
Pulegone ((R)-5-Methyl-2-(1-methylethylidine) cyclohexanone) is a pharmacologically active, natural monoterpene ketone obtained from leaves and flowering tops of the mint family (Lamiaceae). The aim is to comprise the physicochemical and biological aspects of pulegone. All significant databases were collected via electronic search using Pubmed, Scopus, Web of Science, and Science Direct and were compiled. This review presents the occurrence, chemistry, and modifications of pulegone structure and its effect on the biological system. Pulegone represents various pharmacological properties, i.e., antioxidant, antimicrobial, anti-feeding, antifungal, antiviral, and pesticide activities, and has a significant role as an abortifacient and emmenagogue. Thus, this present review concludes the knowledgeable erudition on pulegone that paves the way for further work.
Topics: Monoterpenes; Monoterpene Aldehydes and Ketones; Ketones; Cyclohexane Monoterpenes; Lamiaceae
PubMed: 36263486
DOI: 10.2174/2772434418666221018090507 -
Molecules (Basel, Switzerland) Mar 2023The essential oils yield of , and was different. gave a relatively higher yield (2.1 ± 0.1%), while that of was low (1.0 ± 0.1%) and that of was lower (0.75 ±...
The essential oils yield of , and was different. gave a relatively higher yield (2.1 ± 0.1%), while that of was low (1.0 ± 0.1%) and that of was lower (0.75 ± 0.1% of dry matter). The active ingredients of the essential oils and some of their biological effects were also determined. The characterization of their chemical compositions showed that the three essences have different chemical profiles: was richer in sesquiterpenes (β-Himachalene (54.21%) and γ -Himachalene (15.54%)), was very rich in monoterpene peroxides and monoterpenes (α-Terpinene (53.4%), ascaridole (17.7%) and ρ-Cymene (12.1%)) and was very rich in monoterpene compounds and monoterpenols (p-cymene (35.11%), γ-Eudesmol (11.9%), L-linalool (11.51%) and piperitone (10.28%)). The in vitro measurement of antioxidant activity by the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) reduction assay showed a significant performance of the eucalyptus oil and average performance of the other two ( and . The in vitro bio-test for their antimicrobial effects showed that the antibacterial activity differed depending on the essential oil and the concentration used, and that their bactericidal efficacy was similar or superior to that of synthetic antibiotics. The toxicity test on rats revealed that the LD of the three essential oils was 500 mg/kg body weight, which classifies them as category four cytotoxic natural products at high doses.
Topics: Rats; Animals; Antioxidants; Eucalyptus; Chenopodium ambrosioides; Cedrus; Eucalyptus Oil; Anti-Bacterial Agents; Monoterpenes; Oils, Volatile; Plant Oils
PubMed: 37049738
DOI: 10.3390/molecules28072974 -
Physical Chemistry Chemical Physics :... Oct 2022Limonene, a monoterpene, found in cleaning products and air fresheners can interact with a variety of surfaces in indoor environments. An oxidation product of limonene,...
Limonene, a monoterpene, found in cleaning products and air fresheners can interact with a variety of surfaces in indoor environments. An oxidation product of limonene, carvone, has been reported to cause contact allergens. In this study, we have investigated the interactions of limonene and carvone with TiO, a component of paint and self-cleaning surfaces, at 297 ± 1 K with FTIR spectroscopy and force field-based molecular dynamics and simulations. The IR absorption spectra and computational methods show that limonene forms π-hydrogen bonds with the surface O-H groups on the TiO surface and that carvone adsorbs on the TiO surface through a variety of molecular interactions including through carbonyl oxygen atoms with Ti surface atoms, O-H hydrogen bonding (carbonyl O⋯HO) and π-hydrogen bonds with surface O-H groups. Furthermore, we investigated the effects of relative humidity (RH) on the adsorption of limonene and carvone on the TiO surface. The spectroscopic results show that the adsorbed limonene can be completely displaced by water at a relative humidity of 50% RH (∼2 MLs of water) and that 25% of carvone is displaced at 67% RH, which agrees with the calculated free energies of adsorption which show carvone more strongly adsorbs on the surface relative to limonene and thus would be harder to displace from the surface. Overall, this study shows how a monoterpene and its oxidation product interact with TiO and the impact of relative humidity on these interactions.
Topics: Cyclohexane Monoterpenes; Limonene; Monoterpenes; Oxygen; Titanium; Water
PubMed: 36165087
DOI: 10.1039/d2cp03021g -
Acta Tropica Sep 2020This review aims to describe essential oils with bioactivity on adult snails of the genera Bulinus and Biomphalaria, which are intermediate hosts of schistosomes, and... (Review)
Review
This review aims to describe essential oils with bioactivity on adult snails of the genera Bulinus and Biomphalaria, which are intermediate hosts of schistosomes, and brings together information relating to the importance of molluscicides and the chemical composition and toxicity of such oils for other aquatic species. Analysis of the data of original articles revealed that 50 essential oils obtained from 46 plant species were evaluated for molluscicidal activity against the genera cited. More than 80% of the volatile oils studied were active, according to the criteria of the World Health Organization (LC or LC ≤100 µg/mL or LC <40 µg/mL), and most of the oils came from plants belonging to the Rutaceae, Lamiaceae and Pinaceae. Around 37% of the surveyed plant species were obtained in Brazil and 88% of these plants were collected in the northeast of the country, a region with a high prevalence of schistosomiasis mansoni. The essential oils with the highest toxicity against host snails had high levels of hydrocarbon monoterpenes and oxygenated monoterpenes, which may be responsible for the molluscicidal activity. Some volatile components were subjected to molluscicidal evaluation, and the monoterpene compounds exhibited a significant molluscicide effect. This review confirmed the importance of essential oils as a promising alternative for the development of natural molluscicide products. However, in order to be safe for use at sites where schistosome intermediate hosts are found, information on ecotoxicity is required and, to date, few oils have been tested against non-target aquatic species.
Topics: Animals; Humans; Molluscacides; Monoterpenes; Oils, Volatile; Schistosomiasis; Snails
PubMed: 32404294
DOI: 10.1016/j.actatropica.2020.105489