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1.
Molecules ; 29(9)2024 Apr 25.
Artículo en Inglés | MEDLINE | ID: mdl-38731461

RESUMEN

This present study aims to characterize the essential oil compositions of the aerial parts of M. spicata L. and endemic M. longifolia ssp. cyprica (Heinr. Braun) Harley by using GC-FID and GC/MS analyses simultaneously. In addition, it aims to perform multivariate statistical analysis by comparing with the existing literature, emphasizing the literature published within the last two decades, conducted on both species growing within the Mediterranean Basin. The major essential oil components of M. spicata were determined as carvone (67.8%) and limonene (10.6%), while the major compounds of M. longifolia ssp. cyprica essential oil were pulegone (64.8%) and 1,8-cineole (10.0%). As a result of statistical analysis, three clades were determined for M. spicata: a carvone-rich chemotype, a carvone/trans-carveol chemotype, and a pulegone/menthone chemotype, with the present study result belonging to the carvone-rich chemotype. Carvone was a primary determinant of chemotype, along with menthone, pulegone, and trans-carveol. In M. longifolia, the primary determinants of chemotype were identified as pulegone and menthone, with three chemotype clades being pulegone-rich, combined menthone/pulegone, and combined menthone/pulegone with caryophyllene enrichment. The primary determinants of chemotype were menthone, pulegone, and caryophyllene. The present study result belongs to pulegone-rich chemotype.


Asunto(s)
Cromatografía de Gases y Espectrometría de Masas , Mentha spicata , Mentha , Aceites Volátiles , Aceites Volátiles/química , Mentha/química , Mentha spicata/química , Análisis Multivariante , Región Mediterránea , Monoterpenos Ciclohexánicos/química , Monoterpenos Ciclohexánicos/análisis , Monoterpenos/química , Monoterpenos/análisis , Limoneno/química , Terpenos/química , Terpenos/análisis , Mentol
2.
J Agric Food Chem ; 72(19): 10958-10969, 2024 May 15.
Artículo en Inglés | MEDLINE | ID: mdl-38703118

RESUMEN

Demand for the exploration of botanical pesticides continues to increase due to the detrimental effects of synthetic chemicals on human health and the environment and the development of resistance by pests. Under the guidance of a bioactivity-guided approach and HSQC-based DeepSAT, 16 coumarin derivatives were discovered from the leaves of Ailanthus altissima (Mill.) Swingle, including seven undescribed monoterpenoid coumarins, three undescribed monoterpenoid phenylpropanoids, and two new coumarin derivatives. The structure and configurations of these compounds were established and validated via extensive spectroscopic analysis, acetonide analysis, and quantum chemical calculations. Biologically, 5 exhibited significant antifeedant activity toward the Plutella xylostella. Moreover, tyrosinase being closely related to the growth and development of larva, the inhibitory potentials of 5 against tyrosinase was evaluated in vitro and in silico. The bioactivity evaluation results highlight the prospect of 5 as a novel category of botanical insecticide.


Asunto(s)
Ailanthus , Cumarinas , Insecticidas , Extractos Vegetales , Hojas de la Planta , Hojas de la Planta/química , Animales , Cumarinas/farmacología , Cumarinas/química , Ailanthus/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Insecticidas/química , Insecticidas/farmacología , Estructura Molecular , Larva/efectos de los fármacos , Larva/crecimiento & desarrollo , Mariposas Nocturnas/efectos de los fármacos , Mariposas Nocturnas/crecimiento & desarrollo , Monofenol Monooxigenasa/antagonistas & inhibidores , Monofenol Monooxigenasa/metabolismo , Bioensayo , Monoterpenos/farmacología , Monoterpenos/química , Conducta Alimentaria/efectos de los fármacos , Inhibidores Enzimáticos/farmacología , Inhibidores Enzimáticos/química
3.
Food Res Int ; 187: 114458, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38763690

RESUMEN

This study examines the antimicrobial and antibiofilm effectiveness of baicalin and carvacrol against Salmonella enterica ser. Typhimurium on food contact surfaces and chicken meat. The minimum inhibitory concentrations (MIC) for baicalin and carvacrol were found to be 100 µg/mL and 200 µg/mL, respectively, which aligns with findings from previous studies. The compounds exhibited a concentration-dependent decrease in microbial populations and biofilm formation. When used together, they displayed a remarkable synergistic effect, greatly augmenting their antibacterial activity. The assessment of food quality demonstrated that these treatments have no negative impact on the sensory characteristics of chicken meat. The impact of the structure on biofilms was observed through the use of Field Emission Scanning Electron Microscopy (FE-SEM) and Confocal Laser Scanning Microscopy (CLSM), revealing disrupted biofilm architectures and decreased cell viability. Crucially, RT-PCR analysis revealed a marked downregulation of quorum sensing (luxS), virulence (hilA), and stress response (rpoS) genes, highlighting the multifaceted antimicrobial mechanism of action. This gene-specific suppression suggests a targeted disruption of bacterial communication and virulence pathways, offering insight into the comprehensive antibiofilm strategy. This provides further insight into the molecular mechanisms that contribute to their antibiofilm effects.


Asunto(s)
Antibacterianos , Biopelículas , Pollos , Cimenos , Flavonoides , Microbiología de Alimentos , Pruebas de Sensibilidad Microbiana , Salmonella typhimurium , Biopelículas/efectos de los fármacos , Cimenos/farmacología , Salmonella typhimurium/efectos de los fármacos , Flavonoides/farmacología , Antibacterianos/farmacología , Animales , Percepción de Quorum/efectos de los fármacos , Carne/microbiología , Monoterpenos/farmacología , Microscopía Electrónica de Rastreo
4.
Planta ; 260(1): 3, 2024 May 20.
Artículo en Inglés | MEDLINE | ID: mdl-38767800

RESUMEN

MAIN CONCLUSION: Transcription factors MhMYB1 and MhMYB2 correlate with monoterpenoid biosynthesis pathway in l-menthol chemotype of Mentha haplocalyx Briq, which could affect the contents of ( -)-menthol and ( -)-menthone. Mentha haplocalyx Briq., a plant with traditional medicinal and edible uses, is renowned for its rich essential oil content. The distinct functional activities and aromatic flavors of mint essential oils arise from various chemotypes. While the biosynthetic pathways of the main monoterpenes in mint are well understood, the regulatory mechanisms governing different chemotypes remain inadequately explored. In this investigation, we identified and cloned two transcription factor genes from the M. haplocalyx MYB family, namely MhMYB1 (PP236792) and MhMYB2 (PP236793), previously identified by our research group. Bioinformatics analysis revealed that MhMYB1 possesses two conserved MYB domains, while MhMYB2 contains a conserved SANT domain. Yeast one-hybrid (Y1H) analysis results demonstrated that both MhMYB1 and MhMYB2 interacted with the promoter regions of MhMD and MhPR, critical enzymes in the monoterpenoid biosynthesis pathway of M. haplocalyx. Subsequent virus-induced gene silencing (VIGS) of MhMYB1 and MhMYB2 led to a significant reduction (P < 0.01) in the relative expression levels of MhMD and MhPR genes in the VIGS groups of M. haplocalyx. In addition, there was a noteworthy decrease (P < 0.05) in the contents of ( -)-menthol and ( -)-menthone in the essential oil of M. haplocalyx. These findings suggest that MhMYB1 and MhMYB2 transcription factors play a positive regulatory role in ( -)-menthol biosynthesis, consequently influencing the essential oil composition in the l-menthol chemotype of M. haplocalyx. This study serves as a pivotal foundation for unraveling the regulatory mechanisms governing monoterpenoid biosynthesis in different chemotypes of M. haplocalyx.


Asunto(s)
Regulación de la Expresión Génica de las Plantas , Mentha , Mentol , Monoterpenos , Proteínas de Plantas , Factores de Transcripción , Factores de Transcripción/genética , Factores de Transcripción/metabolismo , Mentha/genética , Mentha/metabolismo , Monoterpenos/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Mentol/metabolismo , Aceites Volátiles/metabolismo , Vías Biosintéticas/genética , Regiones Promotoras Genéticas/genética
5.
Int J Mol Sci ; 25(9)2024 Apr 23.
Artículo en Inglés | MEDLINE | ID: mdl-38731832

RESUMEN

Cancer is a disease that encompasses multiple and different malignant conditions and is among the leading causes of death in the world. Therefore, the search for new pharmacotherapeutic options and potential candidates that can be used as treatments or adjuvants to control this disease is urgent. Natural products, especially those obtained from plants, have played an important role as a source of specialized metabolites with recognized pharmacological properties against cancer, therefore, they are an excellent alternative to be used. The objective of this research was to evaluate the action of the monoterpene isoespintanol (ISO) against the human tumor cell lines MDA-MB-231, A549, DU145, A2780, A2780-cis and the non-tumor line MRC-5. Experiments with 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and fluorescence with propidium iodide (PI), 4',6-diamidino-2-phenylindole dilactate (DAPI) and green plasma revealed the cytotoxicity of ISO against these cells; furthermore, morphological and chromogenic studies revealed the action of ISO on cell morphology and the inhibitory capacity on reproductive viability to form colonies in MDA-MB-231 cells. Likewise, 3D experiments validated the damage in these cells caused by this monoterpene. These results serve as a basis for progress in studies of the mechanisms of action of these compounds and the development of derivatives or synthetic analogues with a better antitumor profile.


Asunto(s)
Monoterpenos , Humanos , Línea Celular Tumoral , Monoterpenos/farmacología , Supervivencia Celular/efectos de los fármacos , Antineoplásicos/farmacología , Proliferación Celular/efectos de los fármacos , Apoptosis/efectos de los fármacos
6.
Sci Rep ; 14(1): 10650, 2024 05 09.
Artículo en Inglés | MEDLINE | ID: mdl-38724532

RESUMEN

Avoiding fatigue is a long-standing challenge in both healthy and diseased individuals. Establishing objective standard markers of fatigue is essential to evaluate conditions in spatiotemporally different locations and individuals and identify agents to fight against fatigue. Herein, we introduced a novel method for evaluating fatigue using nervous system markers (including dopamine, adrenaline, and noradrenaline), various cytokine levels (such as interleukin [IL]-1ß, tumor necrosis factor [TNF]-α, IL-10, IL-2, IL-5 and IL-17A), and oxidative stress markers (such as diacron-reactive oxygen metabolites [d-ROMs] and biological antioxidant potential [BAP]) in a rat fatigue model. Using this method, the anti-fatigue effects of methyl dihydrojasmonate (MDJ) and linalool, the fragrance/flavor compounds used in various products, were assessed. Our method evaluated the anti-fatigue effects of the aforementioned compounds based on the changes in levels of the nerves system markers, cytokines, and oxidative stress markers. MDJ exerted more potent anti-fatigue effects than linalool. In conclusion, the reported method could serve as a useful tool for fatigue studies and these compounds may act as effective therapeutic agents for abrogating fatigue symptoms.


Asunto(s)
Monoterpenos Acíclicos , Citocinas , Modelos Animales de Enfermedad , Fatiga , Estrés Oxidativo , Animales , Estrés Oxidativo/efectos de los fármacos , Monoterpenos Acíclicos/farmacología , Ratas , Fatiga/tratamiento farmacológico , Fatiga/metabolismo , Citocinas/metabolismo , Masculino , Ciclopentanos/farmacología , Antioxidantes/farmacología , Biomarcadores , Monoterpenos/farmacología , Oxilipinas/farmacología , Ratas Sprague-Dawley
7.
J Pharm Biomed Anal ; 245: 116184, 2024 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-38692214

RESUMEN

The plant of Paeonia lactiflora Pall. belongs to Ranunculaceae, and its root can be divided into two categories according to different processing methods, which included that one was directly dried without peeling the root of the P. lactiflora (PR), and the other was peeled the root of the P. lactiflora (PPR) after boiled and dried. To evaluate the difference of chemical components, UPLC-ESI-Q-Exactive Focus-MS/MS and UPLC-QQQ-MS were applied. The distribution of chemical components in different tissues was located by laser microdissection (LMD), especially the different ingredients. A total of 86 compounds were identified from PR and PPR. Four kind of tissues were isolated from the fresh root of the P. lactiflora (FPR), and 54 compounds were identified. Especially the content of gallic acid, albiflorin, and paeoniflorin with high biological activities were the highest in the cork, but they were lower in PR than that in PPR, which probably related to the process. To illustrate the difference in pharmacological effects of PR and PPR, the tonifying blood and analgesic effects on mice were investigated, and it was found that the tonifying blood and analgesic effects of PPR was superior to that of PR, even though PR had more constituents. The material basis for tonifying blood and analgesic effect of the root of P. lactiflora is likely to be associated with an increase in constituents such as paeoniflorin and paeoniflorin lactone after boiled and peeled. The study was likely to provide some theoretical support for the standard and clinical application.


Asunto(s)
Glucósidos , Monoterpenos , Paeonia , Raíces de Plantas , Espectrometría de Masas en Tándem , Paeonia/química , Raíces de Plantas/química , Animales , Ratones , Espectrometría de Masas en Tándem/métodos , Cromatografía Líquida de Alta Presión/métodos , Glucósidos/análisis , Glucósidos/química , Masculino , Monoterpenos/farmacología , Monoterpenos/análisis , Monoterpenos/química , Microdisección/métodos , Ácido Gálico/análisis , Ácido Gálico/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Rayos Láser , Analgésicos/farmacología , Analgésicos/química , Analgésicos/análisis , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Espectrometría de Masa por Ionización de Electrospray/métodos , Cromatografía Líquida con Espectrometría de Masas , Hidrocarburos Aromáticos con Puentes
8.
Chem Biol Interact ; 395: 111032, 2024 May 25.
Artículo en Inglés | MEDLINE | ID: mdl-38705442

RESUMEN

Particulate matter (PM), the main component of air pollutants, emerges as a research hotspot, especially in the area of respiratory diseases. Paeoniflorin (PAE), known as anti-inflammatory and immunomodulatory effects, has been reported to alleviate acute lung injury (ALI). However, the effect of PAE on PM-induced ALI and the underlying mechanisms are still unclear yet. In this study, we established the PM-induced ALI model using C57BL/6J mice and BEAS-2B cells to explore the function of PAE. In vivo, mice were intraperitoneally injected with PAE (100 mg/kg) or saline 1 h before instilled with 4 mg/kg PM intratracheally and were euthanized on the third day. For lung tissues, HE staining and TUNEL staining were used to evaluate the degree of lung injury, ELISA assay was used to assess inflammatory mediators and oxidative stress level, Immunofluorescence staining and western blotting were applied to explore the role of pyroptosis and Nrf2 signaling pathway. In vitro, BEAS-2B cells were pretreated with 100 µM PAE before exposure to 200 µg/ml PM and were collected after 24h for the subsequent experiments. TUNEL staining, ROS staining, and western blotting were conducted to explore the underlying mechanisms of PAE on PM-induced ALI. According to the results, PAE can attenuate the degree of PM-induced ALI in mice and reduce PM-induced cytotoxicity in BEAS-2B cells. PAE can relieve PM-induced excessive oxidative stress and NLRP3 inflammasome-mediated pyroptosis. Additionally, PAE can also activate Nrf2 signaling pathway and inhibition of Nrf2 signaling pathway can impair the protective effect of PAE by aggravating oxidative stress and pyroptosis. Our findings demonstrate that PAE can attenuate PM-induced ALI by inhibiting oxidative stress and NLRP3 inflammasome-mediated pyroptosis, which is mediated by Nrf2 signaling pathway.


Asunto(s)
Lesión Pulmonar Aguda , Glucósidos , Inflamasomas , Ratones Endogámicos C57BL , Monoterpenos , Factor 2 Relacionado con NF-E2 , Proteína con Dominio Pirina 3 de la Familia NLR , Estrés Oxidativo , Material Particulado , Piroptosis , Transducción de Señal , Animales , Factor 2 Relacionado con NF-E2/metabolismo , Lesión Pulmonar Aguda/inducido químicamente , Lesión Pulmonar Aguda/tratamiento farmacológico , Lesión Pulmonar Aguda/metabolismo , Lesión Pulmonar Aguda/patología , Lesión Pulmonar Aguda/prevención & control , Proteína con Dominio Pirina 3 de la Familia NLR/metabolismo , Piroptosis/efectos de los fármacos , Estrés Oxidativo/efectos de los fármacos , Material Particulado/toxicidad , Glucósidos/farmacología , Glucósidos/uso terapéutico , Transducción de Señal/efectos de los fármacos , Ratones , Monoterpenos/farmacología , Inflamasomas/metabolismo , Masculino , Humanos , Línea Celular
9.
J Appl Microbiol ; 135(4)2024 Apr 01.
Artículo en Inglés | MEDLINE | ID: mdl-38587823

RESUMEN

AIM: In this study, it was aimed to examine the antibacterial activity of the essential oil components (EOCs), carvacrol (CAR), cinnamaldehyde (CIN), thymol (TH), alpha pinene (α-PN), eucalyptol (EU), limonene (LIM), and the antibiotics, linezolid (LZD), vancomycin (VAN), gentamicin (GEN), ciprofloxacin (CIP), clindamycin (CLN), and penicillin (PEN) against 50 multidrug resistant Corynebacterium striatum strains, and the synergistic interactions of CAR and CIN with the antibiotics against 10 randomly selected Coryne. striatum strains to explore synergistic interactions to determine if their combined use could enhance antibiotic activity and potentially reduce resistance. METHODS AND RESULTS: The activity of the EOCs and the antibiotics against Coryne. striatum strains isolated from clinical specimens, was examined by broth microdilution method. The synergistic interactions of the EOCs with the antibiotics against 10 randomly selected Coryne. striatum strains were determined by checkerboard method. EOCs, CIN, and CAR and antibiotics, LZD, VAN, GEN, CIP, and CLN were detected to have antibacterial activity against Coryne. striatum strains alone and either synergistic interactions were observed in combinations of the antibiotics with EOCs. CONCLUSIONS: All Coryne. striatum strains were determined to be susceptible to VAN and LZD and resistant to GEN, PEN, CIP, and CLN. Synergistic interactions were observed in all combinations of antibiotics tested with CAR and CIN.


Asunto(s)
Acroleína , Acroleína/análogos & derivados , Antibacterianos , Corynebacterium , Farmacorresistencia Bacteriana Múltiple , Sinergismo Farmacológico , Pruebas de Sensibilidad Microbiana , Monoterpenos , Aceites Volátiles , Antibacterianos/farmacología , Corynebacterium/efectos de los fármacos , Aceites Volátiles/farmacología , Farmacorresistencia Bacteriana Múltiple/efectos de los fármacos , Acroleína/farmacología , Monoterpenos/farmacología , Cimenos/farmacología , Ciprofloxacina/farmacología , Gentamicinas/farmacología , Vancomicina/farmacología , Linezolid/farmacología , Limoneno/farmacología , Eucaliptol/farmacología , Timol/farmacología , Clindamicina/farmacología , Humanos , Penicilinas/farmacología , Terpenos/farmacología , Ciclohexenos/farmacología , Infecciones por Corynebacterium/microbiología
10.
Int J Mol Sci ; 25(7)2024 Mar 31.
Artículo en Inglés | MEDLINE | ID: mdl-38612715

RESUMEN

Breast cancer (BC) represents one of the most prevalent malignant threats to women globally. Tumor relapse or metastasis is facilitated by BC stemness progression, contributing to tumorigenicity. Therefore, comprehending the characteristics of stemness progression and the underlying molecular mechanisms is pivotal for BC advancement. Hinokitiol (ß-thujaplicin), a tropolone-related compound abundant in the heartwood of cupressaceous plants, exhibits antimicrobial activity. In our study, we employed three BC cell lines (MDA-MB-231, MCF-7, and T47D) to assess the expression of stemness-, apoptosis-, and autophagy-related proteins. Hinokitiol significantly reduced the viability of cancer cells in a dose-dependent manner. Furthermore, we observed that hinokitiol enhances apoptosis by increasing the levels of cleaved poly-ADP-ribose polymerase (PARP) and phospho-p53. It also induces dysfunction in autophagy through the upregulation of LC3B and p62 protein expression. Additionally, hinokitiol significantly suppressed the number and diameter of cancer cell line spheres by reducing the expression of cluster of differentiation44 (CD44) and key transcription factors. These findings underscore hinokitiol's potential as a therapeutic agent for breast cancer, particularly as a stemness-progression inhibitor. Further research and clinical studies are warranted to explore the full therapeutic potential of hinokitiol in the treatment of breast cancer.


Asunto(s)
Neoplasias de la Mama , Monoterpenos , Tropolona , Tropolona/análogos & derivados , Humanos , Femenino , Tropolona/farmacología , Neoplasias de la Mama/tratamiento farmacológico , Recurrencia Local de Neoplasia , Apoptosis , Autofagia , Células MCF-7 , Receptores de Hialuranos , Factores de Transcripción SOXB1
11.
Int J Mol Sci ; 25(8)2024 Apr 15.
Artículo en Inglés | MEDLINE | ID: mdl-38673947

RESUMEN

Phyllotreta striolata, the striped flea beetle, is one of the most destructive pests in Brassicaceae plants worldwide. Given the drawbacks associated with long-term use of chemical insecticides, green strategies based on chemical ecology are an effective alternative for beetle control. However, the lack of information on beetle ecology has hindered the development of effective biocontrol strategies. In this report, we identified two odorants, (S)-cis-verbenol and (-)-verbenone, which displayed significant attraction for P. striolata (p < 0.05), indicating their great potential for P. striolata management. Using the Drosophila "empty neuron" system, an antenna-biased odorant receptor, PstrOR17, was identified as responsible for the detection of (-)-verbenone and (S)-cis-verbenol. Furthermore, the interactions between PstrOR17 and (-)-verbenone or (S)-cis-verbenol were predicted via modeling and molecular docking. Finally, we used RNAi to confirm that PstrOR17 is essential for the detection of (-)-verbenone and (S)-cis-verbenol to elicit an attraction effect. Our results not only lay a foundation for the development of new and effective nonchemical insecticide strategies based on (S)-cis-verbenol and (-)-verbenone, but also provide new insight into the molecular basis of odorant recognition in P. striolata.


Asunto(s)
Monoterpenos Bicíclicos , Escarabajos , Receptores Odorantes , Animales , Antenas de Artrópodos/efectos de los fármacos , Antenas de Artrópodos/metabolismo , Monoterpenos Bicíclicos/farmacología , Escarabajos/efectos de los fármacos , Escarabajos/metabolismo , Proteínas de Insectos/genética , Proteínas de Insectos/metabolismo , Proteínas de Insectos/química , Simulación del Acoplamiento Molecular , Monoterpenos/química , Monoterpenos/farmacología , Odorantes , Receptores Odorantes/genética , Receptores Odorantes/metabolismo
12.
Mol Nutr Food Res ; 68(8): e2300831, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38602198

RESUMEN

SCOPE: The excretion of dietary odorants into urine and milk is evaluated and the impact of possible influencing factors determined. Furthermore, the metabolic relevance of conjugates for the excretion into milk is investigated. METHODS AND RESULTS: Lactating mothers (n = 20) are given a standardized curry dish and donated one milk and urine sample each before and 1, 2, 3, 4.5, 6, and 8 h after the intervention. The concentrations of nine target odorants in these samples are determined. A significant transition is observed for linalool into milk, as well as for linalool, cuminaldehyde, cinnamaldehyde, and eugenol into urine. Maximum concentrations are reached within 1 h after the intervention in the case of milk and within 2-3 h in the case of urine. In addition, the impact of glucuronidase treatment on odorant concentrations is evaluated in a sample subset of twelve mothers. Linalool, eugenol, and vanillin concentrations increased 3-77-fold in milk samples after treatment with ß-glucuronidase. CONCLUSION: The transfer profiles of odorants into milk and urine differ qualitatively, quantitatively, and in temporal aspects. More substances are transferred into urine and the transfer needs a longer period compared with milk. Phase II metabolites are transferred into urine and milk.


Asunto(s)
Acroleína/análogos & derivados , Monoterpenos Acíclicos , Benzaldehídos , Eugenol , Leche Humana , Odorantes , Humanos , Leche Humana/química , Femenino , Odorantes/análisis , Eugenol/orina , Eugenol/metabolismo , Eugenol/análogos & derivados , Adulto , Benzaldehídos/orina , Monoterpenos Acíclicos/orina , Glucuronidasa/metabolismo , Lactancia , Acroleína/orina , Acroleína/metabolismo , Monoterpenos/orina
13.
PLoS One ; 19(4): e0299218, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38662654

RESUMEN

To enhance the yield of the one-step synthesis of terpinyl acetate from α-pinene and acetic acid, this study evaluated α-hydroxycarboxylic acid (HCA)-boric acid composite catalysts based on orthogonal experimental design. The most important factor affecting the terpinyl acetate content in the product was the HCA content. The catalytic performance of the composite catalyst was related to the pKa1 of HCA. The tartaric acid-boric acid composite catalyst showed the highest catalytic activity. The α-pinene conversion reached 91.8%, and the terpinyl acetate selectivity reached 45.6%. When boric acid was replaced with B2O3, the HCA composite catalyst activity was enhanced, which reduced the use of HCA. When the lactic acid and B2O3 content accounted for 10% and 4% of the α-pinene mass content, respectively, the α-pinene conversion reached 93.2%, and the terpinyl acetate selectivity reached up to 47.1%. In addition, the presence of water was unfavorable to HCA-boric acid composite catalyst. However, a water content less than 1% of the α-pinene mass content improved the catalytic activity of HCA-B2O3. When the tartaric acid-B2O3 was used as catalyst, and the water content was 1% of the α-pinene mass content, the α-pinene conversion was 89.6%, and the terpinyl acetate selectivity was 47.5%.


Asunto(s)
Monoterpenos Bicíclicos , Ácidos Bóricos , Monoterpenos , Catálisis , Monoterpenos Bicíclicos/química , Ácidos Bóricos/química , Monoterpenos/química , Tartratos/química , Acetatos/química , Ácidos Carboxílicos/química , Terpenos/química , Terpenos/síntesis química
14.
J Chromatogr A ; 1723: 464716, 2024 May 24.
Artículo en Inglés | MEDLINE | ID: mdl-38640881

RESUMEN

Saposhnikoviae Radix (SR) may enhance the pharmacodynamics of Huangqi Chifeng Tang (HQCFT) in the treatment of cerebral infarction according to our previous research, but the underlying mechanism is unknown. Herein, an in vivo pharmacokinetic assay in rats and in vitro MDCK-MDR1 cell assays were used to investigate the possible mechanism of SR, its main components, and its interactions with Astragali Radix (AR) and Paeoniae Radix (PR). An ultrahigh-performance liquid chromatography-tandem mass spectrometry (UPLC‒MS/MS)-based analytical method for quantifying astragaloside IV (ASIV) and paeoniflorin (PAE) in microdialysis and transport samples was developed. The pharmacokinetic parameters of SR were determined using noncompartmental analyses CCK-8 assays were used to detect the cytotoxicity of ASIV, PAE, cimifugin (CIM), prim-o-glucosylcimifugin (POG) and their combinations. Moreover, drug transport was studied using MDCK-MDR1 cells. Western blotting was performed to measure the protein expression levels of P-GP and MRP1. Claudin-5, ZO-1, and F-actin expression was determined via immunohistochemical staining of MDCK-MDR1 cells. harmacokinetic studies revealed that, compared with those of Huangqi Chifeng Tang-Saposhnikoviae Radix (HQCFT-SR), the Tmax of ASIV increased by 11.11 %, and the MRT0-t and Tmax of PAE increased by 11.19 % and 20 %, respectively, in the HQCFT group. Transport studies revealed that when ASIV was coincubated with 28 µM CIM or POG, the apparent permeability coefficient (Papp) increased by 71.52 % and 50.33 %, respectively. Coincubation of PAE with 120 µM CIM or POG increased the Papp by 87.62 % and 60.95 %, respectively. Moreover, CIM and POG significantly downregulated P-gp and MRP1 (P < 0.05), inhibited the expression of Claudin-5, ZO-1, and F-actin (P < 0.05), and affected intercellular tight junctions (TJs). In conclusion, our study successfully established a selective, sensitive and reproducible UPLC‒MS/MS analytical method to detect drug‒drug interactions between SR, AR and PR in vivo and in vitro, which is beneficial for enhancing the therapeutic efficacies of AR and PR. Moreover, this study provides a theoretical basis for further research on the use of SR as a drug carrier.


Asunto(s)
Medicamentos Herbarios Chinos , Glucósidos , Monoterpenos , Ratas Sprague-Dawley , Saponinas , Espectrometría de Masas en Tándem , Triterpenos , Animales , Glucósidos/farmacocinética , Glucósidos/análisis , Glucósidos/química , Glucósidos/farmacología , Saponinas/farmacocinética , Saponinas/farmacología , Saponinas/química , Saponinas/análisis , Monoterpenos/análisis , Triterpenos/farmacología , Triterpenos/farmacocinética , Triterpenos/química , Triterpenos/análisis , Perros , Ratas , Células de Riñón Canino Madin Darby , Espectrometría de Masas en Tándem/métodos , Masculino , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Medicamentos Herbarios Chinos/farmacocinética , Cromatografía Líquida de Alta Presión/métodos , Apiaceae/química , Interacciones de Hierba-Droga , Interacciones Farmacológicas , Reproducibilidad de los Resultados
15.
Bioorg Med Chem Lett ; 105: 129737, 2024 Jun 01.
Artículo en Inglés | MEDLINE | ID: mdl-38599297

RESUMEN

A new monoterpenoid, neoroseoside (1), along with two previously reported compounds, 2″-O-α-l-rhamnosyl-6-C-fucosylluteolin (2) and farobin A (3) were isolated from the Zea mays. The structure of compound 1 was determined through the analysis spectroscopic data, including mass spectrometry (MS), infrared (IR) spectroscopy, and nuclear magnetic resonance (NMR) data. The absolute configurations of 1 were deduced from the comparing the values of optical rotations and from the interpretation of electronic circular dichroism (ECD) spectra. Compounds 2 and 3 displayed moderate antibacterial activity against Streptococcus mutans ATCC 25175 (inhibition rates 24 % and 28 %, respectively) and Streptococcus sobrinus ATCC 33478 (inhibition rate of 26 %), at a concentration of 100 µg/mL, whereas compound 1 did not have any significant antibacterial activities. The compounds 1-3 also showed anti-inflammatory activity on cytokine IL-6 and TNF-α.


Asunto(s)
Antibacterianos , Pruebas de Sensibilidad Microbiana , Monoterpenos , Zea mays , Zea mays/química , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Monoterpenos/farmacología , Monoterpenos/química , Monoterpenos/aislamiento & purificación , Antiinflamatorios/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Relación Estructura-Actividad , Estructura Molecular , Streptococcus mutans/efectos de los fármacos , Interleucina-6/metabolismo , Interleucina-6/antagonistas & inhibidores , Descubrimiento de Drogas , Factor de Necrosis Tumoral alfa/antagonistas & inhibidores , Factor de Necrosis Tumoral alfa/metabolismo , Relación Dosis-Respuesta a Droga , Streptococcus/efectos de los fármacos
16.
J Chromatogr A ; 1722: 464896, 2024 May 10.
Artículo en Inglés | MEDLINE | ID: mdl-38631224

RESUMEN

In this study, a novel magnetic bead-based ligand fishing method was developed for rapid discovery of monoterpene indoles as monoamine oxidase A inhibitors from natural products. In order to improve the screening efficiency, two different magnetic beads, i.e. amine and carboxyl terminated magnetic beads, were comprehensively compared in terms of their ability to immobilize monoamine oxidase A (MAOA), biocatalytic activity and specific adsorption rates for affinity ligands. Carboxyl terminated magnetic beads performed better for MAOA immobilization and demonstrated superior performance in ligand fishing. The MAOA immobilized magnetic beads were applied to screen novel monoamine oxidase inhibitors in an alkaloid-rich plant, Hunteria zeylanica. Twelve MAOA affinity ligands were screened out, and ten of them were identified as monoterpene indole alkaloids by HPLC-Obitrap-MS/MS. Among them, six ligands, namely geissoschizol, vobasinol, yohimbol, dihydrocorynanthenol, eburnamine and (+)-isoeburnamine which exhibited inhibitory activity against MAOA with low IC50 values. To further explore their inhibitory mechanism, enzyme kinetic analysis and molecular docking studies were conducted.


Asunto(s)
Simulación del Acoplamiento Molecular , Inhibidores de la Monoaminooxidasa , Monoaminooxidasa , Inhibidores de la Monoaminooxidasa/química , Inhibidores de la Monoaminooxidasa/farmacología , Inhibidores de la Monoaminooxidasa/aislamiento & purificación , Monoaminooxidasa/metabolismo , Monoaminooxidasa/química , Ligandos , Indoles/química , Monoterpenos/química , Monoterpenos/aislamiento & purificación , Cinética , Espectrometría de Masas en Tándem/métodos , Cromatografía Líquida de Alta Presión/métodos , Enzimas Inmovilizadas/química , Enzimas Inmovilizadas/metabolismo , Enzimas Inmovilizadas/antagonistas & inhibidores , Humanos , Extractos Vegetales/química
17.
Int J Mol Sci ; 25(8)2024 Apr 13.
Artículo en Inglés | MEDLINE | ID: mdl-38673908

RESUMEN

A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of the first type of aminodiols was achieved starting from (-)-8,9-dihydroperillaldehyde via reductive amination, followed by Boc protection and dihydroxylation with the OsO4/NMO system. Separation of formed stereoisomers resulted in a library of aminodiol diastereoisomers. The library of regioisomeric analogues was obtained starting from (-)-8,9-dihydroperillic alcohol, which was transformed into a mixture of allylic trichloroacetamides via Overman rearrangement. Changing the protecting group to a Boc function, the protected enamines were subjected to dihydroxylation with the OsO4/NMO system, leading to a 71:16:13 mixture of diastereoisomers, which were separated, affording the three isomers in isolated form. The obtained primary aminodiols were transformed into secondary derivatives. The regioselectivity of the ring closure of the N-benzyl-substituted aminodiols with formaldehyde was also investigated, resulting in 1,3-oxazines in an exclusive manner. To explain the stability difference between diastereoisomeric 1,3-oxazines, a series of comparative theoretical modelling studies was carried out. The obtained potential catalysts were applied in the reaction of aromatic aldehydes and diethylzinc with moderate to good enantioselectivities (up to 94% ee), whereas the opposite chiral selectivity was observed between secondary aminodiols and their ring-closed 1,3-oxazine analogues.


Asunto(s)
Monoterpenos , Compuestos Organometálicos , Estereoisomerismo , Catálisis , Monoterpenos/química , Benzaldehídos/química , Amino Alcoholes/química , Amino Alcoholes/síntesis química , Estructura Molecular , Aldehídos/química
18.
Food Chem ; 449: 139240, 2024 Aug 15.
Artículo en Inglés | MEDLINE | ID: mdl-38599109

RESUMEN

The study reports the efficacy of nanofabricated citronellal inside the chitosan biopolymer (NeCn) against Aspergillus flavus growth, aflatoxin B1 (AFB1) production, and active ingredient biodeterioration (Piperine) in Piper longum L. The prepared NeCn was characterized by Scanning Electron Microscopy (SEM), Dynamic Light Scattering (DLS), and Fourier Transform Infrared Spectroscopy (FTIR). The results revealed that the NeCn exhibited distantly improved antifungal (1.25 µL/mL) and AFB1 inhibition (1.0 µL/mL) compared to free Cn. The perturbances in membrane function, mitochondrial membrane potential, antioxidant defense system, and regulatory genes (Ver-1 and Nor-1) of AFB1 biosynthesis were reported as probable modes of action of NeCn. The NeCn (1.25 µL/mL) effectively protects the P. longum from A. flavus (78.8%), AFB1 contamination (100%), and deterioration of Piperine (62.39%), thus demonstrating its potential as a promising novel antifungal agent for food preservation.


Asunto(s)
Monoterpenos Acíclicos , Aflatoxina B1 , Aspergillus flavus , Quitosano , Piper , Aflatoxina B1/metabolismo , Aspergillus flavus/efectos de los fármacos , Aspergillus flavus/crecimiento & desarrollo , Aspergillus flavus/metabolismo , Quitosano/química , Quitosano/farmacología , Piper/química , Biopolímeros/química , Biopolímeros/farmacología , Monoterpenos Acíclicos/farmacología , Monoterpenos Acíclicos/química , Aldehídos/farmacología , Aldehídos/química , Antifúngicos/farmacología , Antifúngicos/química , Conservación de Alimentos/métodos , Monoterpenos/farmacología , Monoterpenos/química , Extractos Vegetales/química , Extractos Vegetales/farmacología
19.
Zhongguo Zhong Yao Za Zhi ; 49(5): 1369-1377, 2024 Mar.
Artículo en Chino | MEDLINE | ID: mdl-38621985

RESUMEN

A total of 11 active ingredients including psoralen, isopsoralen, bakuchiol, bavachalcone, bavachinin, corylin, coryfolin, isobavachalcone, neobavaisoflavone, bakuchalcone, and corylifol A from Psoraleae Fructus in the plasma samples of diabetic and normal rats were simultaneously determined by UHPLC-MS/MS. The pharmacokinetic parameters were calculated to elucidate the pharmacokinetic profiles of coumarins, flavonoids, and monoterpene phenols in normal and diabetic rats. The rat model of type 2 diabetes mellitus(T2DM) was induced by a high-sugar and high-fat diet combined with injection of 1% streptozotocin every two days. The plasma samples were collected at different time points after the rats were administrated with Psoraleae Fructus. The proteins in the plasma samples were precipitated by ethyl acetate, and the plasma concentrations of the 11 components of Psoraleae Fructus were determined by UHPLC-MS/MS. The pharmacokinetic parameters were calculated by DAS 3.0. The results showed that the pharmacokinetic beha-viors of 8 components including psoralen, isopsoralen, bakuchiol, and bavachinin from Psoraleae Fructus in both female and male mo-del rats were significantly different from those in normal rats. Among them, the coumarins including psoralen, isopsoralen, and corylin showed lowered levels in the blood of both female and male model rats. The flavonoids(bavachinin, corylifol A, and bakuchalcone) and the monoterpene phenol bakuchiol showed decreased levels in the female model rats but elevated levels in the male model rats. It is suggested that the dosage of Psoraleae Fructus should be reasonably adjusted for the patients of different genders at the time of clinical administration.


Asunto(s)
Diabetes Mellitus Experimental , Diabetes Mellitus Tipo 2 , Medicamentos Herbarios Chinos , Furocumarinas , Fenoles , Psoralea , Humanos , Ratas , Femenino , Masculino , Animales , Medicamentos Herbarios Chinos/farmacocinética , Espectrometría de Masas en Tándem/métodos , Diabetes Mellitus Experimental/tratamiento farmacológico , Flavonoides/farmacología , Ficusina , Cumarinas , Monoterpenos
20.
Pestic Biochem Physiol ; 201: 105886, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38685252

RESUMEN

This study evaluates the pediculicidal activity of nanoformulations containing different binary essential oil component mixtures (eugenol:linalool, 1,8 -cineole:linalool, and eugenol:thymol) using immersion bioassays. These have allowed us to evaluate the knockdown time affecting 50% of the individuals (KT50). In addition, the type of interaction between the components in each mixture was established in terms of the combination index (IC). The KT50 values were 6.07; 8.83; 7.17 and 27.23 h for linalool, 1,8 -cineole, eugenol, and thymol, respectively. For the eugenol:linalool mixtures, the efficacy was lower or equal to that obtained for the nanoformulations of the pure compounds, with values of KT50 about 13.33, 8.16 and 6.71 h for mixtures with ratios 3:1, 1:1 and 1:3, respectively. These mixtures present IC > 1, evidencing antagonistic interaction, which is enhanced with eugenol content. In the case of the binary mixtures of 1,8 -cineole: linalool, KT50 values were similar to those obtained for eugenol:linalool mixtures with similar ratios. In this case, IC assumes values close to unity, suggesting additive interactions independently of the mixture composition. On the other side, mixtures of eugenol:thymol with 1:1 and 1:3 ratios showed values of 9.40 and 32.93 h, while the mixture with a 3:1 ratio showed the greatest effectiveness (KT50 of 4.42 h). Eugenol:thymol mixtures show synergistic interaction (IC < 1) for combinations 3:1 and 1:1, while no interaction was observed for 1:3 combination. This indicates that eugenol enhances thymol activity. These results must be considered an important step forward to the development of effective pediculicidal nanoformulations based on botanical compounds.


Asunto(s)
Monoterpenos Acíclicos , Eucaliptol , Eugenol , Monoterpenos , Monoterpenos/farmacología , Monoterpenos/química , Animales , Eugenol/farmacología , Eugenol/química , Eucaliptol/farmacología , Monoterpenos Acíclicos/farmacología , Monoterpenos Acíclicos/química , Pediculus/efectos de los fármacos , Insecticidas/farmacología , Insecticidas/química , Timol/farmacología , Timol/química , Micelas , Aceites Volátiles/farmacología , Aceites Volátiles/química , Nanopartículas/química , Infestaciones por Piojos/tratamiento farmacológico
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