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1.
Chem Biodivers ; 21(3): e202301259, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38157454

RESUMEN

Cupressus torulosa is an evergreen tree with a wide distribution in north-western Himalayan region of India. Its needles have long been used in traditional medicine for anti-inflammatory, antimicrobial, and wound-healing properties. This study aimed to scientifically validate the traditional claim of the needles to treat inflammation by evaluating the chemical composition, antioxidant potential, and anti-inflammatory activity of the essential oil extracted from the needles (CTEO) using hydro-distillation. Qualitative and quantitative chemical composition of the CTEO was determined with the aid of GC-MS and GC-FID techniques. The major constituents of the CTEO were terpinen-4-ol (393.8±12.5 µg/mg), totarol (55.0±17.2 µg/mg), and sabinene (43.7±2.8 µg/mg). CTEO exhibited significant antioxidant activity when evaluated using DPPH free radical scavenging and reducing power assays. Furthermore, the CTEO demonstrated good anti-inflammatory behavior in in vitro egg albumin denaturation assay, with an IC50 of 27.32 µg/mL. In vivo tests using carrageenan-induced paw edema and xylene-induced ear edema in rats showed significant effects at doses of 30 mg/kg for up to 1 hour. The significant discoveries not only support the established assertions about the anti-inflammatory properties of C. torulosa needles but also highlight their potential as a useful resource in the growing herbal, complementary, and alternative medicine sectors.


Asunto(s)
Antiinfecciosos , Cupressus , Aceites Volátiles , Ratas , Animales , Aceites Volátiles/farmacología , Aceites Volátiles/uso terapéutico , Cupressus/química , Antiinflamatorios/farmacología , Antiinflamatorios/uso terapéutico , Antiinfecciosos/farmacología , Antioxidantes/farmacología , Antioxidantes/química , Extractos Vegetales/química , Edema/inducido químicamente , Edema/tratamiento farmacológico
2.
Biomed Pharmacother ; 167: 115609, 2023 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-37801906

RESUMEN

Cupressus sempervirens is a known traditional plant used to manage various ailments, including cancer, inflammatory and infectious diseases. In this investigation, we aimed to explore the chemical profile of Cupressus sempervirens essential oil (CSEO) as well as their antibacterial mode of action. The volatile components were characterized using gas chromatography coupled to a mass spectrometer (GC-MS). The results revealed remarkable antibacterial properties of EO derived from C. sempervirens. GC-MS analysis indicated that C. sempervirens EO characterized by δ-3-carene (47.72%), D-limonene (5.44%), ß-pinene (4.36%), ß-myrcene (4.02%). The oil exhibited significant inhibitory effects against a range of bacteria, including Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC 13048, Bacillus cereus (Clinical isolate), Pseudomonas aeruginosa ATCC 27853, and Escherichia coli ATCC 25922. These inhibitory effects surpassed those of conventional antibiotics. Furthermore, the EO demonstrated low minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs), indicating its bactericidal nature (MBC/MIC < 4.0). Time-kill kinetics analysis showed that CSEO was particularly effective at 2 × MIC doses, rapidly reduced viable count of B. subtilis and P. aeruginosa within 8 h. This suggests that the oil acts quickly and efficiently. The cell membrane permeability test further demonstrated the impact of CSEO on the relative conductivity of B. subtilis and P. aeruginosa, both at 2 × MIC concentrations. These observations suggest that EO disrupts the bacterial membrane, thereby influencing their growth and viability. Additionally, the cell membrane integrity test indicated that the addition of CSEO to bacterial cultures resulted in the significant release of proteins from the bacterial cells. This suggests that EO affects the structural integrity of the bacterial cells. Furthermore, the anti-biofilm assay confirmed the efficacy of CSEO as a potent anti-biofilm agent. It demonstrated the oil's ability to inhibit quorum sensing, a crucial mechanism for biofilm formation, and its competitive performance compared to the tested antibiotics.


Asunto(s)
Cupressus , Aceites Volátiles , Bacillus subtilis , Pseudomonas aeruginosa , Cupressus/química , Antibacterianos/farmacología , Antibacterianos/química , Aceites Volátiles/farmacología , Aceites Volátiles/química , Pruebas de Sensibilidad Microbiana
3.
Naturwissenschaften ; 110(2): 13, 2023 Mar 27.
Artículo en Inglés | MEDLINE | ID: mdl-36971882

RESUMEN

Several sawfly species (Hymenoptera: Symphyta) possess larval stages with oesophageal diverticula in which plant compounds are sequestered and used for defence against predators. These organs are present in the larvae of Susana (Tenthredinidae) but remain poorly studied. Here, the aim was to analyse the diverticula extract of Susana cupressi by gas chromatography-mass spectrometry to better understand the ecology of this species. The foliage of the hostplant (Cupressus sempervirens), as well as the larval foregut, midgut, and haemolymph were also analysed. Complementary data were gathered by morphological observations, bioassays using ants, and genetic analyses to identify the studied Susana species. Altogether, 48 terpenes were identified, 30 being sesquiterpenes. The terpenes were generally detected in the foliage, but also in the diverticula, foregut, and midgut, whereas none of them in the haemolymph. The main compounds were alpha-cedrene, alpha-fenchene, alpha-pinene, alpha-terpinyl acetate, beta-myrcene, beta-pinene, cedrol, delta 3-carene, epi-bicyclosesquiphellandrene, germacrene D, limonene, sabinene, and terpinolene. The chemical profiles of these 13 compounds were significantly correlated between foliage-diverticula, diverticula-foregut and foregut-midgut, but not correlated for the three remaining possible comparisons. Alpha-pinene decreased and germacrene D increased from the foliage to the diverticula, which may reflect a specific sequestration of the latter terpene and its known deleterious effects on insects. We conclude that larvae of S. cupressi, similarly to those of diprionids, are well defended against predatory attacks by sequestering and regurgitating hostplant terpenes, including germacrene D.


Asunto(s)
Hormigas , Cupressus , Divertículo , Himenópteros , Animales , Cupressus/química , Larva , Terpenos/análisis
4.
Naunyn Schmiedebergs Arch Pharmacol ; 396(3): 389-403, 2023 03.
Artículo en Inglés | MEDLINE | ID: mdl-36385684

RESUMEN

The roles of plants and its products in all forms of life cannot be overemphasized. The medicinal products from plant are phytochemicals, drugs, food supplements, beauty products, etc. In ethnomedicine, leaves, fruits, stem, bark, root and fluids from plants are used in the cure, management and prevention of several diseases. Cupressus sempervirens, sometimes called Italian or Mediterranean cypress, is found in subtropical Asia, North America and eastern Mediterranean region. Pharmacological investigations of Cupressus sempervirens showed biological properties such as aromatherapeutic, antiseptic, astringent, balsamic or anti-inflammatory, astringent, antiperspirant, diuretic and antispasmodic. Chemical analysis of Cupressus sempervirens gives phytochemicals like monoterpenes, diterpenes, flavonoid glycosides and bioflavonoids. The current review highlights interactions, conventional uses and biological actions of Cupressus sempervirens plant and plant products.


Asunto(s)
Cupressus , Diterpenos , Cupressus/química , Astringentes , Monoterpenos , Frutas , Flavonoides/farmacología
5.
Nat Prod Res ; 37(14): 2408-2414, 2023 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-36448408

RESUMEN

The hydrodistilled volatile essential oils extracted from the female cones of Cupressus arizonica Greene that harvested in winter and spring seasons were analysed for their chemical composition by using gas chromatography-mass spectrometry (GC/MS). Twenty-four and seventeen components were identified, accounting for winter (95.5%) and spring (96.9%) of the total oils volume, respectively. Monoterpenoids (winter 93.7% and spring 95.0%) dominated the identified components in the essential oils, followed by a small portion of sesquiterpenoids (winter 1.8% and spring 1.9%). Monoterpene hydrocarbons (MH) (winter 90.9% and spring 94.9%) were the principal subclasses of components with α-pinene (winter 42% and spring 72%), ß-myrcene (winter 18.5% and spring 7.7%), δ-3-carene (winter 11.3% and spring 5.1%), limonene (9.4% for winter), and ß-pinene (5.3% for spring) as main constituents. Limonene (9.4%), camphor (0.2%), exo-methylcamphenilol (0.2%), terpinene-4-ol (0.6%), ß-citronellol (0.9%), and bornyl acetate (0.3%) were representative of the monoterpene hydrocarbon and oxygen-containing monoterpenoids (OM) in winter essential oil.


Asunto(s)
Cupressaceae , Cupressus , Aceites Volátiles , Aceites Volátiles/química , Cupressus/química , Limoneno , Monoterpenos/análisis
6.
Molecules ; 27(9)2022 Apr 19.
Artículo en Inglés | MEDLINE | ID: mdl-35565980

RESUMEN

Nowadays, increasing interest has recently been given to the exploration of new food preservatives to avoid foodborne outbreaks or food spoilage. Likewise, new compounds that substitute the commonly used synthetic food preservatives are required to restrain the rising problem of microbial resistance. Accordingly, the present study was conducted to examine the chemical composition and the mechanism(s) of action of the Cupressus sempervirens essential oil (CSEO) against Salmonella enterica Typhimuriumand Staphyloccocus aureus. The gas chromatography analysis revealed α-pinene (38.47%) and δ-3-carene (25.14%) are the major components of the CSEO. By using computational methods, such as quantitative structure-activity relationship (QSAR), we revealed that many CSEO components had no toxic effects. Moreover, findings indicated that α-pinene, δ-3-carene and borneol, a minor compound of CSEO, could inhibit the AcrB-TolC and MepR efflux pump activity of S. enterica Typhimurium and S. aureus, respectively. In addition, our molecular docking predictions indicated the high affinity of these three compounds with active sites of bacterial DNA and RNA polymerases, pointing to plausible impairments of the pathogenic bacteria cell replication processes. As well, the safety profile was developed through the zebrafish model. The in vivo toxicological evaluation of (CSEO) exhibited a concentration-dependent manner, with a lethal concentration (LC50) equal to 6.6 µg/mL.


Asunto(s)
Cupressus , Aceites Volátiles , Animales , Antibacterianos/farmacología , Cupressus/química , Conservantes de Alimentos , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , Aceites Volátiles/química , Aceites Volátiles/farmacología , Staphylococcus aureus , Pez Cebra
7.
Molecules ; 27(2)2022 Jan 06.
Artículo en Inglés | MEDLINE | ID: mdl-35056664

RESUMEN

Monterey cypress (Cupressus macrocarpa) is a decorative plant; however, it possesses various pharmacological activities. Therefore, we explored the phytochemical profile of C. macrocarpa root methanol extract (CRME) for the first time. Moreover, we investigated its antidiarrheal (in vivo), antibacterial, and antibiofilm (in vitro) activities against Salmonella enterica clinical isolates. The LC-ESI-MS/MS analysis of CRME detected the presence of 39 compounds, besides isolation of 2,3,2″,3″-tetrahydro-4'-O-methyl amentoflavone, amentoflavone, and dihydrokaempferol-3-O-α-l-rhamnoside for the first time. Dihydrokaempferol-3-O-α-l-rhamnoside presented the highest antimicrobial activity and the range of values of MICs against S. enterica isolates was from 64 to 256 µg/mL. The antidiarrheal activity of CRME was investigated by induction of diarrhea using castor oil, and exhibited a significant reduction in diarrhea and defecation frequency at all doses, enteropooling (at 400 mg/kg), and gastrointestinal motility (at 200, 400 mg/kg) in mice. The antidiarrheal index of CRME increased in a dose-dependent manner. The effect of CRME on various membrane characters of S. enterica was studied after typing the isolates by ERIC-PCR. Its impact on efflux and its antibiofilm activity were inspected. The biofilm morphology was observed using light and scanning electron microscopes. The effect on efflux activity and biofilm formation was further elucidated using qRT-PCR. A significant increase in inner and outer membrane permeability and a significant decrease in integrity and depolarization (using flow cytometry) were detected with variable percentages. Furthermore, a significant reduction in efflux and biofilm formation was observed. Therefore, CRME could be a promising source for treatment of gastrointestinal tract diseases.


Asunto(s)
Antibacterianos/farmacología , Antidiarreicos/farmacología , Cupressus/química , Diarrea/tratamiento farmacológico , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Salmonella enterica/efectos de los fármacos , Animales , Aceite de Ricino/toxicidad , Catárticos/toxicidad , Diarrea/inducido químicamente , Diarrea/patología , Motilidad Gastrointestinal , Técnicas In Vitro , Masculino , Ratones
8.
Molecules ; 26(24)2021 Dec 10.
Artículo en Inglés | MEDLINE | ID: mdl-34946554

RESUMEN

Cupressus sempervirens L., Juniperus communis L. and Cistus ladanifer L. are Mediterranean arboreal and shrub species that possess essential oils (EO) in their leaves and branches. This study aimed at characterizing the EOs obtained by steam distillation from the three species collected in different locations from Spain (Almazán, Andévalo, Barriomartín, Cerezal, Ermitas and Huéscar). For this purpose, volatiles composition was determined by GC-MS, and different bioactivities were evaluated. The highest content in terpenes was observed in C. sempervirens (Huéscar origin) followed by J. communis (Almazán origin), corresponding to 92% and 91.9% of total compounds, respectively. With exception of C. ladanifer from Cerezal that presented viridiflorol as the most abundant compound, all the three species presented in common the α-pinene as the major compound. The EOs from C. ladanifer showed high antibacterial potential, presenting MIC values from 0.3 to 1.25 mg/mL. Concerning other bioactivities, C. ladanifer EO revealed an oxidation inhibition of 83%, while J. communis showed cytotoxicity in the MCF-7 cell line, and C. sempervirens and C. ladanifer EOs exhibited the highest potential on NCI-H460 cell lines. Nevertheless, some EOs revealed toxicity against non-tumoral cells but generally presented a GI50 value higher than that of the tumor cell lines.


Asunto(s)
Antibacterianos/farmacología , Antineoplásicos Fitogénicos/farmacología , Antioxidantes/farmacología , Cistus/química , Cupressus/química , Juniperus/química , Aceites Volátiles/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Línea Celular , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Bacterias Gramnegativas/efectos de los fármacos , Humanos , Pruebas de Sensibilidad Microbiana , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Picratos/antagonistas & inhibidores
9.
J Microbiol Biotechnol ; 31(12): 1656-1666, 2021 Dec 28.
Artículo en Inglés | MEDLINE | ID: mdl-34489380

RESUMEN

Dental pathogens lead to chronic diseases like periodontitis, which causes loss of teeth. Here, we examined the plausible antibacterial efficacy of copper nanoparticles (CuNPs) synthesized using Cupressus macrocarpa extract (CME) against periodontitis-causing bacteria. The antimicrobial properties of CME-CuNPs were then assessed against oral microbes (M. luteus. B. subtilis, P. aerioginosa) that cause periodontal disease and were identified using morphological/ biochemical analysis, and 16S-rRNA techniques. The CME-CuNPs were characterized, and accordingly, the peak found at 577 nm using UV-Vis spectrometer showed the formation of stable CME-CuNPs. Also, the results revealed the formation of spherical and oblong monodispersed CME-CuNPs with sizes ranged from 11.3 to 22.4 nm. The FTIR analysis suggested that the CME contains reducing agents that consequently had a role in Cu reduction and CME-CuNP formation. Furthermore, the CME-CuNPs exhibited potent antimicrobial efficacy against different isolates which was superior to the reported values in literature. The antibacterial efficacy of CME-CuNPs on oral bacteria was compared to the synergistic solution of clindamycin with CME-CuNPs. The solution exhibited a superior capacity to prevent bacterial growth. Minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and fractional inhibitory concentration (FIC) of CME-CuNPs with clindamycin recorded against the selected periodontal disease-causing microorganisms were observed between the range of 2.6-3.6 µg/ml, 4-5 µg/ml and 0.312-0.5, respectively. Finally, the synergistic antimicrobial efficacy exhibited by CME-CuNPs with clindamycin against the tested strains could be useful for the future development of more effective treatments to control dental diseases.


Asunto(s)
Antibacterianos/farmacología , Cobre/química , Nanopartículas del Metal/química , Periodontitis/microbiología , Antibacterianos/química , Bacterias/clasificación , Bacterias/efectos de los fármacos , Bacterias/genética , Bacterias/aislamiento & purificación , Cobre/farmacología , Cupressus/química , Farmacorresistencia Bacteriana/efectos de los fármacos , Sinergismo Farmacológico , Tecnología Química Verde , Humanos , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/química
10.
Nanotechnology ; 32(21)2021 Mar 03.
Artículo en Inglés | MEDLINE | ID: mdl-33657016

RESUMEN

Background. The development of dental caries is associated with various microorganisms and secondary caries formation is the main cause of restorations failure. The advice for restorative dental materials that have antimicrobial properties has stimulated the introduction of materials containing different antibacterial agents.Objectives. The present study has been designed to synthesize silver nanoparticles (AgNPs) and incorporate AgNPs and amoxicillin into glass ionomer cement (GIC) to synergize its effect on oral microbes. The effect of the added antimicrobial agents on compressive strength (CS) of GIC was also evaluated.Material and methods. Biosynthesis of AgNPs was done usingCupressus macrocarpaextract and AgNPs were characterized. A total of 120 disc-shaped specimens were prepared and classified into 4 main groups where Group A includes conventional GIC, Groups B and C include GIC with AgNPs or amoxicillin, respectively, while Group D included GIC with both AgNPs and amoxicillin. Each group was tested for the antimicrobial activity against bothStreptococcus mutans(S. mutans) andStaphylococcus aureus(S. aureus). The distribution of biofilm was examined via a scanning electron microscope. The CS of the tested material was measured using a Material Test System.Results. The UV-visible spectrum showed a peak of 429 nm. Transmission electron microscopy, x-ray diffraction pattern and Fourier transform infrared analysis confirmed the formation of AgNPs with spherical to oblong polydispersed particles of diameter in the range of 13.5-25.8 nm. The maximum inhibitory zone was recorded for group D against both tested bacteria with a mean of 29 mm at first 24 h period to 15 mm at three weeks and showed antimicrobial rate 92.2% and 92.56%, against both strains, respectively. Additionally, group D disintegrated the structure ofS. aureusbiofilm and even kill bacteria in the biofilms. The addition of AgNPs and amoxicillin caused an insignificant effect on CS of GIC.Conclusion.TheAgNPs showed a synergistic effect in combination with amoxicillin and GIC dental restorative material against studied microorganisms. The agents can be safely added with minimal effect on the mechanical properties of the original cement.


Asunto(s)
Amoxicilina/farmacología , Antiinfecciosos/química , Cementos de Ionómero Vítreo/química , Nanopartículas del Metal/química , Plata/química , Staphylococcus aureus/efectos de los fármacos , Streptococcus mutans/efectos de los fármacos , Antiinfecciosos/metabolismo , Antiinfecciosos/farmacología , Cupressus/química , Cupressus/metabolismo , Tecnología Química Verde , Nanopartículas del Metal/toxicidad , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/química
11.
Anal Biochem ; 621: 114123, 2021 05 15.
Artículo en Inglés | MEDLINE | ID: mdl-33549546

RESUMEN

In the present study, a simple, cheaply and environmental friendly method was evaluated for the synthesis of silver nanoparticle via Cupressus sempervirens L. (CSPE) pollen extract as reducing and stabilizing agent. Various parameters such as volume of CSPE, temperature and reaction time on AgNPs formation were investigated spectrophotometrically to optimize reaction conditions. The electrochemical behavior of the biosynthesized AgNPs were investigated by cyclic voltammetry and square wave voltammetry techniques. An electrosensor based on AgNPs modified glassy carbon electrode were constructed and tested on electro reduction of hydrogen peroxide in phosphate buffer medium. The prepared electrosensor could detect the H2O2 in the range of 5.0 µM - 2.5 mM with a detection limit of 0.23 µM. In addition, the antioxidant activity of biosynthesized AgNPs were evaluated against DPPH free radical. Results obtained from the antioxidant study suggested that CSPE mediated AgNPs exhibit a good antioxidant effect.


Asunto(s)
Antioxidantes/análisis , Técnicas Electroquímicas/instrumentación , Nanopartículas del Metal/química , Extractos Vegetales/química , Polen/química , Plata/química , Cupressus/química , Técnicas Electroquímicas/métodos , Electrodos , Radicales Libres/análisis , Peróxido de Hidrógeno/análisis , Tamaño de la Partícula , Fitoquímicos/química , Reproducibilidad de los Resultados , Espectroscopía Infrarroja por Transformada de Fourier , Temperatura , Difracción de Rayos X
12.
Chemosphere ; 260: 127521, 2020 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-32688310

RESUMEN

The Punchuncaví Valley is one of the most polluted areas in central Chile affected by anthropogenic emissions from the Ventanas Industrial Complex (IC) where the most important industry is the copper smelter and refinery. In this context, this research aims were to assess the usefulness of the Cupressus macrocarpa as a biomonitor. The leaf samples were taken from five selected sites, located between 0.8 and 15 km away from the source. A total of 34 elements were analyzed in leaf samples by ICP-MS and examined by enrichment factor (EF), hierarchical cluster analysis (HCA), and principal component analysis (PCA). Leaf concentration of As, Ca, Cd, Cu, Dy, Er, Gd, K, Li, Mg, Mn, Mo, Na, Nd, P, Pb, Pr, S, Sb, Sr, Ti, Yb and Zn showed statistically significant differences between sampling sites (p-value < 0.05). A clear trend to increase the concentration of Cu, Sb, S, As, Cd and Pb with the proximity to the IC. Besides, high values of Cu (93.4-369 mg kg-1) and As (7.6-12.7 mg kg-1) were observed near to industrial area exceed the phytotoxic levels reported in plants with EF > 3000% for Cu and >1300% for As. The application of PCA and HCA identified 6 factors related to the industrial complex, traffic and geogenic sources, providing the greatest variance the component related to industrial activity mainly with copper smelter and refinery. According to the results, the C. macrocarpa leaves are a good biomonitor to evaluate the high pollution load for anthropogenic elements in industrial areas.


Asunto(s)
Contaminantes Atmosféricos , Monitoreo Biológico/métodos , Cupressus/química , Metalurgia , Hojas de la Planta/química , Contaminantes Atmosféricos/análisis , Contaminantes Atmosféricos/toxicidad , Chile , Cupressus/crecimiento & desarrollo , Metales/análisis , Metales/toxicidad , Hojas de la Planta/crecimiento & desarrollo , Análisis de Componente Principal , Oligoelementos/análisis , Oligoelementos/toxicidad
13.
Bioorg Chem ; 100: 103850, 2020 07.
Artículo en Inglés | MEDLINE | ID: mdl-32460177

RESUMEN

Two known polyphenols named apigenin 7-O-ß-d-glucopyranoside (S1) and querctine-3-O-glucoside (S2), along with another two new compounds apigenin 4'-geranyl-8-glucopyranosyl-7-O-α-glucopyranoside (S3) and apigenin 4'-pernyl-8-glucopyranosyl -7-O-α-glucopyranoside (S4), were isolated from the leaves of Cupressus sempervirens. Structure elucidation of the isolated polyphenols was established on the basis of detailed spectroscopic analysis like 1D and 2D NMR analyses including 1H NMR, 13C NMR, COSY, DEPT, HMQC, UV, and Electron Spray Ionization Mass Spectroscopy (ESI-MS). Density Functional Theory (DFT) of computational, Petra/Osiris/Molinspiration (POM), and docking analyses methods were applied in the structural validation of new isolated compounds. The isolated compounds S1-S4 showed significant cytotoxicity against human hepatocellular liver carcinoma HepG2 cells, MCF-7, HC116 and A549.


Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Cupressus/química , Flavonoides/química , Flavonoides/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Teoría Funcional de la Densidad , Flavonoides/aislamiento & purificación , Humanos , Simulación del Acoplamiento Molecular , Neoplasias/tratamiento farmacológico , Hojas de la Planta/química
14.
Bioorg Med Chem Lett ; 30(10): 127127, 2020 05 15.
Artículo en Inglés | MEDLINE | ID: mdl-32223924

RESUMEN

Cupressus macrocarpa is a windbreak tree and is reported to have various cytotoxic effects. A natural product study on the leaves of C. macrocarpa has yielded ten secondary metabolites, including three new diterpenoids (1-3), four known diterpenoids (4-7), and three known lignans (8-10). The structures of all isolated compounds were elucidated via the interpretation of spectroscopic methods, especially 2D NMR and mass analyses. In the cytotoxic assays, compounds 1-3 and 7-10 showed inhibition effect against HepG2, MDA-MB-231, and A549 cells with IC50 values ranging from 0.004 to 19.9 µg/mL. Moreover, the anti-inflammatory assays revealed that (-)-matairesinol (8) had significant inhibitory activities on superoxide anion generation (IC50 = 2.7 ± 0.3 µM) and elastase release (IC50 = 6.6 ± 0.7 µM).


Asunto(s)
Antiinflamatorios/química , Cupressus/química , Diterpenos/química , Lignanos/química , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Cupressus/metabolismo , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Humanos , Lignanos/aislamiento & purificación , Lignanos/farmacología , Espectroscopía de Resonancia Magnética , Conformación Molecular , Neutrófilos/citología , Neutrófilos/efectos de los fármacos , Neutrófilos/metabolismo , Elastasa Pancreática/metabolismo , Hojas de la Planta/química , Hojas de la Planta/metabolismo , Superóxidos/metabolismo
15.
Nat Prod Res ; 34(6): 816-822, 2020 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-30398365

RESUMEN

The chemical constituents of Cupressus macrocarpa were investigated. A new neolignan glycoside (1) in addition to nine known compounds were isolated. The acetylcholinesterase (AChE) inhibitory activity and antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) of different fractions and isolates of C. macrocarpa were evaluated. The light petroleum fraction showed the highest activity in both assays with IC50 value of 88.79 µg/ml and 152.58 µg/ml for the AChE inhibitory activity and MRSA antibacterial activities, respectively. Weak to moderate activity were detected for the isolated compounds.


Asunto(s)
Antibacterianos/aislamiento & purificación , Inhibidores de la Colinesterasa/aislamiento & purificación , Cupressus/química , Antibacterianos/farmacología , Inhibidores de la Colinesterasa/farmacología , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Lignanos/aislamiento & purificación , Lignanos/farmacología , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos , Extractos Vegetales/química , Hojas de la Planta/química
16.
Sci Rep ; 9(1): 14860, 2019 10 16.
Artículo en Inglés | MEDLINE | ID: mdl-31619690

RESUMEN

Mulching with organic materials is a management practice with long history for weed suppression, soil water conservation and erosion control. Its potential impact on crop pests is less well explored. Here we report its utility for reducing crop damage by the serious pest, sweetpotato weevil (Cylas formicarius). Laboratory bioassays measured the response of adult female weevils to sweetpotato storage roots beneath mulches of fresh or dried plant materials. Weevils were significant repelled by fresh basil, catnip, basil lime and dry eucalyptus, cypress, lucerne and sugarcane. A subsequent field study found that mulches of dry cypress, eucalyptus and lucerne reduced movement of weevils from a release point to reach sweetpotato plants and lowered level of damage to storage roots. Results demonstrate that mulching with organic materials merits further testing as part of the integrated management of sweetpotato weevil, particularly to protect developing storage roots during dry periods when soil cracking can facilitate access by pests.


Asunto(s)
Compostaje/métodos , Productos Agrícolas/parasitología , Ipomoea batatas/parasitología , Hojas de la Planta/química , Raíces de Plantas/parasitología , Gorgojos/patogenicidad , Animales , Cupressus/química , Eucalyptus/química , Femenino , Herbivoria/fisiología , Medicago sativa/química , Nepeta/química , Ocimum basilicum/química , Dinámica Poblacional , Saccharum/química , Gorgojos/fisiología
17.
Mol Immunol ; 114: 189-195, 2019 10.
Artículo en Inglés | MEDLINE | ID: mdl-31376732

RESUMEN

The presence in cypress pollen of an important allergen, belonging to the gibberellin-regulated protein (GRP) family, has been suggested for many years. However, it has never been isolated and sometimes the homologous peach allergen, Pru p 7, has been used as a surrogate to perform immunological investigations. The aim of this study has been the isolation and molecular characterization of the GRP contained in the Cupressus sempervirens pollen. This protein, named Cypmaclein, has been purified from the natural source using conventional biochemical methods consisting in different chromatographic separations. Cypmaclein has been identified by direct protein sequencing of the N-terminal region and of internal fragments of the molecule. In SDS-PAGE, its apparent molecular mass is slightly higher than that of Pru p 7. Nevertheless, the mass spectrometry experiments reveal that the exact molecular mass of Cypmaclein (6821.88 Da) is very close to that of Pru p 7 (6909.90 Da). Two regions of Cypmaclein have been sequenced providing 50% of its primary structure. A high overall sequence identity of Cypmaclein with all the analyzed GRP has been observed, although in the N-terminal region the high identity is limited to the homolog of Cryptomeria japonica. In circular dichroism experiments Cypmaclein produced a spectrum overlapping that of Pru p 7. However, the comparative analysis of Cypmaclein, Pru p 7 and Pun g 7 IgE reactivity revealed a behavior that was not completely overlapping, thus suggesting that the IgE epitopes are only partially shared. In single point highest inhibition achievable assays performed with the FABER test, Cypmaclein efficiently competed with the allergenic peach and pomegranate GRP in the binding of specific IgE of patients sensitized to Pru p 7. In conclusion, the natural cypress pollen GRP has been isolated for the first time, its structural features have been investigated and its cross-reactivity with Pru p 7 and Pun g 7 has been demonstrated. This protein is now available for further investigations aimed at understanding its clinical relevance in the allergy to cypress pollen. In addition, the prevalence of sensitization directly to Cypmaclein, and not limited to the homologs, can be defined.


Asunto(s)
Cupressus/química , Cupressus/inmunología , Giberelinas/química , Giberelinas/inmunología , Inmunoglobulina E/inmunología , Proteínas de Plantas/química , Proteínas de Plantas/inmunología , Adolescente , Adulto , Secuencia de Aminoácidos , Antígenos de Plantas/química , Antígenos de Plantas/inmunología , Niño , Reacciones Cruzadas/inmunología , Epítopos/química , Epítopos/inmunología , Femenino , Humanos , Masculino , Polen/química , Polen/inmunología , Rinitis Alérgica Estacional/inmunología , Adulto Joven
18.
Microb Pathog ; 135: 103604, 2019 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-31247257

RESUMEN

The present study describes the possibility of using some essential oils and monoterpens as bioagents against the growth of Ralstonia solanacearum, a causal bacterium of potato brown rot disease. Eight isolates of the bacterium were recovered from infected potato tubers, showing typical symptoms of the disease, Isolates were identified as R.solanacearum phylotype II, based on biochemical and physiological characteristics, as well as, at the molecular level through PCR analysis. Three essential oils extracted from Corymbia citriodora (leaves), Cupressus sempervirens (aerial parts), and Lantana camara (aerial parts) were evaluated for their antibacterial activity against eight isolates of R. solanacearum phylotype II. Results demonstrated that L. camara essential oil (concentration 5000 µg/mL) had the highest effects against the RsMo2, RsSc1 and Rs48, with inhibition zone (IZ) values of 17.33, 16.33, and 17.50 mm, respectively, also against Rs2 (IZ 14.33 mm), and RsIs2 (IZ 16 mm). C. citriodora oil showed the highest activity against RsBe2 (IZ 14 mm), RsFr4 (IZ 13.66 mm) and RsNe1 (IZ 13.66 mm). Gas Chromatography-Mass Spectrometry (GC-MS-FID) analyzed the chemical composition of these essential oils. It was proved that L. camara leaves contains mainly trans-caryophyllene (16.24%) and α-humulene (9.55%), in C. citriodora oil were α-citronellal (56.55%), α-citronellol (14.89%), and citronellol acetate (13.04%), and in Cup. sempervirens aerial parts were cedrol (22.17%), and Δ3-carene (18.59%). Five monoterpenes were evaluated against the most resistance Ralstonia isolate RsFr5 to the three studied essential oils and found that limonene had the highest effect against it compared with the lowest thymol. The results proved the strong bio effects of the essential oil from L. camara leaves as a natural product contained monoterpenes that can inhibit the growth of tested R. solanacearum phylotype II isolates.


Asunto(s)
Antibacterianos/farmacología , Monoterpenos/farmacología , Aceites Volátiles/farmacología , Extractos Vegetales/farmacología , Ralstonia solanacearum/efectos de los fármacos , Solanum tuberosum/microbiología , Monoterpenos Acíclicos , Aldehídos/aislamiento & purificación , Aldehídos/farmacología , Antibacterianos/aislamiento & purificación , Cupressus/química , ADN Bacteriano/análisis , Cromatografía de Gases y Espectrometría de Masas , Lantana/química , Pruebas de Sensibilidad Microbiana , Sesquiterpenos Monocíclicos , Monoterpenos/aislamiento & purificación , Myrtaceae/química , Octanoles/aislamiento & purificación , Octanoles/farmacología , Aceites Volátiles/aislamiento & purificación , Enfermedades de las Plantas/microbiología , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Ralstonia solanacearum/crecimiento & desarrollo , Ralstonia solanacearum/aislamiento & purificación , Ralstonia solanacearum/fisiología , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología
19.
Bioorg Chem ; 78: 436-443, 2018 08.
Artículo en Inglés | MEDLINE | ID: mdl-29702360

RESUMEN

The plant diastereoisomeric diterpenes ent-pimara-8(14)-15-dien-19-oic acid, obtained from Viguiera arenaria, and isopimara-8(14)-15-dien-18-oic acid, isolated from Cupressus lusitanica, were distinctly functionalized by the enzymes produced in whole cell cultures of the fungus Preussia minima, isolated from surface sterilized stems of C. lusitanica. The ent-pimaradienoic acid was transformed into the known 7ß-hydroxy-ent-pimara-8(14)-15-dien-19-oic acid, and into the novel diterpenes 7-oxo-8 ß-hydroxy-ent-pimara-8(14)-15-dien-19-oic and 7-oxo-9ß-hydroxy-ent-pimara-8(14)-15-dien-19-oic acids. Isopimara-8(14)-15-dien-18-oic acid was converted into novel diterpenes 11α-hydroxyisopimara-8(14)-15-dien-18-oic acid, 7ß,11α-dihydroxyisopimara-8(14)-15-dien-18-oic acid, and 1ß,11α-dihydroxyisopimara-8(14)-15-dien-18-oic acid, along with the known 7ß-hydroxyisopimara-8(14)-15-dien-18-oic acid. All compounds were isolated and fully characterized by 1D and 2D NMR, especially 13C NMR. The diterpene bioproduct 7-oxo-9ß-hydroxy-ent-pimara-8(14)-15-dien-19-oic acid is an isomer of sphaeropsidin C, a phytotoxin that affects cypress trees produced by Shaeropsis sapinea, one of the main phytopathogen of Cupressus. The differential metabolism of the diterpene isomers used as substrates for biotransformation was interpreted with the help of computational molecular docking calculations, considering as target enzymes those of cytochrome P450 group.


Asunto(s)
Ascomicetos/química , Cupressus/microbiología , Diterpenos/química , Biotransformación , Cupressus/química , Diterpenos/aislamiento & purificación , Diterpenos/metabolismo , Conformación Molecular , Simulación del Acoplamiento Molecular , Estereoisomerismo
20.
BMC Complement Altern Med ; 18(1): 23, 2018 Jan 22.
Artículo en Inglés | MEDLINE | ID: mdl-29357851

RESUMEN

BACKGROUND: Cupressus macrocarpa Hartw and Corymbia citriodora (Hook.) K.D. Hill & L.A.S. Johnson, widely grown in many subtropical areas, are used for commercial purposes, such as in perfumery, cosmetics, and room fresheners. Their potential as a source of antimicrobial compounds may be useful in different applications. METHODS: The chemical composition of essential oils (EOs) from C. macrocarpa branchlets and C. citriodora leaves was analyzed by using gas chromatography-mass spectrometry (GC/MS). Antibacterial and antifungal activities were assessed by the micro-dilution method to determine the minimum inhibitory concentrations (MICs), and minimum fungicidal concentrations (MFCs), and minimum bactericidal concentrations (MBCs). Further, the antioxidant capacity of the EOs was determined via 2,2'-diphenypicrylhydrazyl (DPPH) and ß-carotene-linoleic acid assays. RESULTS: Terpinen-4-ol (23.7%), α-phellandrene (19.2%), α-citronellol (17.3%), and citronellal were the major constituents of EO from C. macrocarpa branchlets, and α-citronellal (56%), α-citronellol (14.7%), citronellol acetate (12.3%), isopulegol, and eucalyptol were the primary constituents of EO from C. citriodora leaves. Antibacterial activity with MIC values of EO from C. citriodora leaves was ranged from 0.06 mg/mL to 0.20 mg/mL, and MBC from 0.12 mg/mL against E. coli to 0.41 mg/mL. EO from C. macrocarpa branchlets showed less activity against bacterial strains. The MIC values against tested fungi of the EO from C. citriodora ranged from 0.11 to 0.52 mg/mL while for EO from C. macrocarpa from 0.29 to 3.21 mg/mL. The MIC and MFC values of EOs against P. funiculosum were lower than those obtained from Ketoconazole (KTZ) (0.20; 0.45; 0.29 and 0.53 mg/mL, respectively, vs 0.21 and 0.41 mg/mL. Antioxidant activity of the EO from C. citriodora was higher than that of the positive control but lower than that of the standard butylhydroxytoluene (BHT) (IC50 = 5.1 ± 0.1 µg/mL). CONCLUSION: The results indicate that the EO from Egyptian trees such as C. citriodora leaves may possesses strong bactericidal and fungicidal activities and can be used as an agrochemical for controlling plant pathogens and in human disease management which will add crop additive value.


Asunto(s)
Cupressus/química , Myrtaceae/química , Aceites Volátiles/farmacología , Extractos Vegetales/farmacología , Antibacterianos/química , Antibacterianos/farmacología , Antifúngicos/química , Antifúngicos/farmacología , Antioxidantes/química , Antioxidantes/farmacología , Bacterias/efectos de los fármacos , Egipto , Hongos/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Aceites Volátiles/química , Extractos Vegetales/química , Hojas de la Planta/química
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