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1.
Chemosphere ; 359: 142344, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38754484

RESUMO

Burning incenses and scented candles may provide harmful chemicals. Although many studies have evaluated volatile organic chemicals emitted by their use and related health risks, extension of our understanding for guiding appropriate use under various use conditions is necessary. In this study, emission characteristics of commercial incenses and scented candles were evaluated in a laboratory chamber using real-time measurement and the time-weighted average exposure concentrations of monoaromatic compounds and monoterpenes were assessed using passive samplers while volunteers living in a studio apartment use them. After burning incense, the average levels of benzene increased from 1.4 to 100 µg m-3. The presence of a wood core in commercial incense products was the main cause of high benzene emission by burning them although the increase in benzene was also influenced by factors such as the brand of the products, the number of incense sticks burned, the duration of each burning session, and ventilation period. Electrical warming of scented candles increased the levels of monoterpenes by factors of 16-30 on average. Considering the emission characteristics found in this study, exposure to benzene and monoterpenes could be mitigated by cautious use of those products in residential areas.


Assuntos
Poluentes Atmosféricos , Poluição do Ar em Ambientes Fechados , Benzeno , Monitoramento Ambiental , Compostos Orgânicos Voláteis , Compostos Orgânicos Voláteis/análise , Poluição do Ar em Ambientes Fechados/análise , Poluição do Ar em Ambientes Fechados/estatística & dados numéricos , Monitoramento Ambiental/métodos , Benzeno/análise , Poluentes Atmosféricos/análise , Habitação , Humanos , Monoterpenos/análise , Odorantes/análise
2.
Molecules ; 29(9)2024 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-38731461

RESUMO

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.


Assuntos
Cromatografia Gasosa-Espectrometria de Massas , Mentha spicata , Mentha , Óleos Voláteis , Óleos Voláteis/química , Mentha/química , Mentha spicata/química , Análise Multivariada , Região do Mediterrâneo , Monoterpenos Cicloexânicos/química , Monoterpenos Cicloexânicos/análise , Monoterpenos/química , Monoterpenos/análise , Limoneno/química , Terpenos/química , Terpenos/análise , Mentol
3.
J Pharm Biomed Anal ; 245: 116184, 2024 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-38692214

RESUMO

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.


Assuntos
Glucosídeos , Monoterpenos , Paeonia , Raízes de Plantas , Espectrometria de Massas em Tandem , Paeonia/química , Raízes de Plantas/química , Animais , Camundongos , Espectrometria de Massas em Tandem/métodos , Cromatografia Líquida de Alta Pressão/métodos , Glucosídeos/análise , Glucosídeos/química , Masculino , Monoterpenos/farmacologia , Monoterpenos/análise , Monoterpenos/química , Microdissecção/métodos , Ácido Gálico/análise , Ácido Gálico/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Lasers , Analgésicos/farmacologia , Analgésicos/química , Analgésicos/análise , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Espectrometria de Massas por Ionização por Electrospray/métodos , Espectrometria de Massa com Cromatografia Líquida , Hidrocarbonetos Aromáticos com Pontes
4.
PLoS One ; 19(5): e0302714, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38805412

RESUMO

With the increasing frequencies of extreme weather events caused by climate change, the risk of forest damage from insect attacks grows. Storms and droughts can damage and weaken trees, reduce tree vigour and defence capacity and thus provide host trees that can be successfully attacked by damaging insects, as often observed in Norway spruce stands attacked by the Eurasian spruce bark beetle Ips typographus. Following storms, partially uprooted trees with grounded crowns suffer reduced water uptake and carbon assimilation, which may lower their vigour and decrease their ability to defend against insect attack. We conducted in situ measurements on windthrown and standing control trees to determine the concentrations of non-structural carbohydrates (NSCs), of phenolic defences and volatile monoterpene emissions. These are the main storage and defence compounds responsible for beetle´s pioneer success and host tree selection. Our results show that while sugar and phenolic concentrations of standing trees remained rather constant over a 4-month period, windthrown trees experienced a decrease of 78% and 37% of sugar and phenolic concentrations, respectively. This strong decline was especially pronounced for fructose (-83%) and glucose (-85%) and for taxifolin (-50.1%). Windthrown trees emitted 25 times greater monoterpene concentrations than standing trees, in particular alpha-pinene (23 times greater), beta-pinene (27 times greater) and 3-carene (90 times greater). We conclude that windthrown trees exhibited reduced resources of anti-herbivore and anti-pathogen defence compounds needed for the response to herbivore attack. The enhanced emission rates of volatile terpenes from windthrown trees may provide olfactory cues during bark beetle early swarming related to altered tree defences. Our results contribute to the knowledge of fallen trees vigour and their defence capacity during the first months after the wind-throw disturbance. Yet, the influence of different emission rates and profiles on bark beetle behaviour and host selection requires further investigation.


Assuntos
Monoterpenos , Fenóis , Picea , Picea/parasitologia , Picea/metabolismo , Monoterpenos/análise , Monoterpenos/metabolismo , Fenóis/análise , Fenóis/metabolismo , Animais , Carboidratos/análise , Besouros/fisiologia , Noruega , Mudança Climática , Vento
5.
J Agric Food Chem ; 72(22): 12478-12488, 2024 Jun 05.
Artigo em Inglês | MEDLINE | ID: mdl-38769753

RESUMO

Pseudococcus longispinus (Targioni-Tozzetti) (Hemiptera: Coccoidea: Pseudococcidae), a polyphagous and cosmopolitan pest native to Australia, is a highly damaging pest for numerous crops of economic importance. The sex pheromone of this species (2-(1,5,5-trimethylcyclopent-2-en-1-yl)ethyl acetate), currently used for pest monitoring purposes, was not attractive to males in field experiments conducted in Spanish persimmon orchards infested with this mealybug. The virgin and mated female volatile profiles of these P. longispinus populations were studied by the volatile collection of effluvia in Porapak-Q. The resulting extracts were analyzed by gas chromatography coupled to mass spectrometry (GC-MS), revealing a new compound specific to virgin females and different from the previously described sex pheromone. Based on GC-MS data and nuclear magnetic resonance experiments, we envisaged monoterpene 2-(1,5-dimethyl-4-methylenecyclopent-2-en-1-yl)ethyl acetate as the new sex pheromone candidate, which was synthesized and shown to be attractive in the field to P. longispinus males of the Spanish population.


Assuntos
Cromatografia Gasosa-Espectrometria de Massas , Hemípteros , Monoterpenos , Atrativos Sexuais , Animais , Hemípteros/química , Atrativos Sexuais/química , Feminino , Masculino , Espanha , Monoterpenos/análise , Monoterpenos/química
6.
J Pharm Biomed Anal ; 246: 116222, 2024 Aug 15.
Artigo em Inglês | MEDLINE | ID: mdl-38763106

RESUMO

Zhenwu Decoction (ZWD), a classic formula from Zhang Zhongjing's "Treatise on Typhoid Fever" in the Han Dynasty, consists of five traditional Chinese medicines: Aconiti Lateralis Radix Praeparata (ALRP), Paeoniae Radix Alba, Poria Cocos, Ginger, and Rhizoma Atractylodis Macrocephalae. To evaluate the chemical constituent consistency of ZWD before and after compatibility, an ultra-performance liquid chromatography-electrospray ionization-quadrupole time-of-flight mass spectrometry was established to comprehensively study the constituents of ZWD. By normalizing the peak area, the pairwise compatibility of ALRP and the other four medicinal herbs, as well as the compatibility of the entire formula were studied, respectively. Multivariate statistical analysis was used to identify the differences. The processed data were analyzed by principal component analysis and supervised orthogonal partial least squared discriminant analysis, and an S-plot was generated to compare the differences in the chemical composition of the two types of decoction samples. The results showed that during the decoction process of ZWD, a total of seven components were recognized as differential compounds before and after compatibility of ZWD, namely 6-gingerol, zingerone, benzoylhypaconine, hypaconitine, benzoylaconine, paeoniflorin and fuziline. The results of this study provide basic data reference for understanding the law of ZWD compatibility and are valuable for the compatibility study of other herbal medicines.


Assuntos
Medicamentos de Ervas Chinesas , Metabolômica , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em Tandem , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/análise , Espectrometria de Massas por Ionização por Electrospray/métodos , Cromatografia Líquida de Alta Pressão/métodos , Espectrometria de Massas em Tandem/métodos , Metabolômica/métodos , Álcoois Graxos/análise , Álcoois Graxos/química , Análise de Componente Principal , Catecóis/análise , Catecóis/química , Zingiber officinale/química , Glucosídeos/análise , Glucosídeos/química , Monoterpenos/análise , Monoterpenos/química , Benzoatos/análise , Benzoatos/química , Hidrocarbonetos Aromáticos com Pontes/análise , Hidrocarbonetos Aromáticos com Pontes/química , Análise Multivariada , Paeonia/química , Aconitum/química , Aconitina/análogos & derivados
7.
J Chromatogr A ; 1723: 464716, 2024 May 24.
Artigo em Inglês | MEDLINE | ID: mdl-38640881

RESUMO

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.


Assuntos
Medicamentos de Ervas Chinesas , Glucosídeos , Monoterpenos , Ratos Sprague-Dawley , Saponinas , Espectrometria de Massas em Tandem , Triterpenos , Animais , Glucosídeos/farmacocinética , Glucosídeos/análise , Glucosídeos/química , Glucosídeos/farmacologia , Saponinas/farmacocinética , Saponinas/farmacologia , Saponinas/química , Saponinas/análise , Monoterpenos/análise , Triterpenos/farmacologia , Triterpenos/farmacocinética , Triterpenos/química , Triterpenos/análise , Cães , Ratos , Células Madin Darby de Rim Canino , Espectrometria de Massas em Tandem/métodos , Masculino , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Medicamentos de Ervas Chinesas/farmacocinética , Cromatografia Líquida de Alta Pressão/métodos , Apiaceae/química , Interações Ervas-Drogas , Interações Medicamentosas , Reprodutibilidade dos Testes
8.
Sci Rep ; 14(1): 5752, 2024 03 08.
Artigo em Inglês | MEDLINE | ID: mdl-38459176

RESUMO

Herbal spices are widely consumed as food additives owing to their distinct aroma and taste as well as a myriad of economic and health value. The aroma profile of four major spices including bay leaf, black pepper, capsicum, and fennel was tested using HS-SPME/GC-MS and in response to the most widely used spices´ processing methods including autoclaving and γ-radiation at low and high doses. Additionally, the impact of processing on microbial contamination of spices was tested using total aerobic count. GC-MS analysis led to the identification of 22 volatiles in bay leaf, 34 in black pepper, 23 in capsicum, and 24 in fennel. All the identified volatiles belonged to oxides/phenols/ethers, esters, ketones, alcohols, sesquiterpene and monoterpene hydrocarbons. Oxides/phenol/ethers were detected at high levels in all tested spices at ca. 44, 28.2, 48.8, 61.1%, in bay leaves, black pepper, capsicum, and fennel, respectively of the total blend and signifying their typical use as spices. Total oxides/phenol/ethers showed an increase in bay leaf upon exposure to γ-radiation from 44 to 47.5%, while monoterpene hydrocarbons were enriched in black pepper upon autoclaving from 11.4 in control to reach 65.9 and 82.6% for high dose and low dose of autoclaving, respectively. Cineole was detected in bay leaf at 17.9% and upon exposure to autoclaving at high dose and γ-radiation (both doses) its level increased by 29-31%. Both autoclaving and γ-radiation distinctly affected aroma profiles in examined spices. Further, volatile variations in response to processing were assessed using multivariate data analysis (MVA) revealing distinct separation between autoclaved and γ-radiated samples compared to control. Both autoclaving at 115 °C for 15 min and radiation at 10 kGy eliminated detected bioburden in all tested spices i.e., reduced the microbial counts below the detection limit (< 10 cfu/g).


Assuntos
Foeniculum , Piper nigrum , Compostos Orgânicos Voláteis , Cromatografia Gasosa-Espectrometria de Massas/métodos , Odorantes/análise , Fenol/análise , Microextração em Fase Sólida/métodos , Quimiometria , Especiarias , Monoterpenos/análise , Éteres , Óxidos , Compostos Orgânicos Voláteis/análise
9.
Molecules ; 29(6)2024 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-38543021

RESUMO

As part of our interest in the volatile phytoconstituents of aromatic plants of the Great Basin, we have obtained essential oils of Ambrosia acanthicarpa (three samples), Artemisia ludoviciana (12 samples), and Gutierrezia sarothrae (six samples) from the Owyhee Mountains of southwestern Idaho. Gas chromatographic analyses (GC-MS, GC-FID, and chiral GC-MS) were carried out on each essential oil sample. The essential oils of A. acanthicarpa were dominated by monoterpene hydrocarbons, including α-pinene (36.7-45.1%), myrcene (21.6-25.5%), and ß-phellandrene (4.9-7.0%). Monoterpene hydrocarbons also dominated the essential oils of G. sarothrae, with ß-pinene (0.5-18.4%), α-phellandrene (2.2-11.8%), limonene (1.4-25.4%), and (Z)-ß-ocimene (18.8-39.4%) as major components. The essential oils of A. ludoviciana showed wide variation in composition, but the relatively abundant compounds were camphor (0.1-61.9%, average 14.1%), 1,8-cineole (0.1-50.8%, average 11.1%), (E)-nerolidol (0.0-41.0%, average 6.8%), and artemisia ketone (0.0-46.1%, average 5.1%). This is the first report on the essential oil composition of A. acanthicarpa and the first report on the enantiomeric distribution in an Ambrosia species. The essential oil compositions of A. ludoviciana and G. sarothrae showed wide variation in composition in this study and compared with previous studies, likely due to subspecies variation.


Assuntos
Artemisia , Óleos Voláteis , Óleos Voláteis/química , Artemisia/química , Ambrosia , Idaho , Monoterpenos/análise
10.
Plant Foods Hum Nutr ; 79(2): 410-416, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38492174

RESUMO

Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is the latest arisen contagious respiratory pathogen related to the global outbreak of atypical pneumonia pandemic (COVID-19). The essential oils (EOs) of Eucalyptus camaldulensis, E. ficifolia F. Muell., E. citriodora Hook, E. globulus Labill, E. sideroxylon Cunn. ex Woolls, and E. torquata Luehm. were investigated for its antiviral activity against SARS-CoV-2. The EOs phytochemical composition was determined using GC/MS analysis. Correlation with the explored antiviral activity was also studied using multi-variate data analysis and Pearson's correlation. The antiviral MTT and cytopathic effect inhibition assays revealed very potent and promising anti SARS-CoV-2 potential for E. citriodora EO (IC50 = 0.00019 µg/mL and SI = 26.27). The multivariate analysis revealed α-pinene, α-terpinyl acetate, globulol, γ -terpinene, and pinocarvone were the main biomarkers for E. citriodora oil. Pearson's correlation revealed that globulol is the top positively correlated compound in E. citriodora oil to its newly explored potent anti SARS-CoV-2 potential. A molecular simulation was performed on globulol via docking in the main active sites of both SARS-CoV-2 viral main protease (Mpro) and spike protein (S). In silico predictive ADMET study was also developed to investigate the pharmacokinetic profile and predict globulol toxicity. The obtained in silico, in vitro and Pearson's correlation results were aligned showing promising SARS-CoV-2 inhibitory activity of E. citriodora and globulol. This study is a first record for E. citriodora EO as a novel lead exhibiting potent in vitro, and in silico anti SARS-CoV-2 potential and suggesting its component globulol as a promising candidate for further extensive in silico, in vitro and in vivo anti-COVID studies.


Assuntos
Antivirais , Eucalyptus , Simulação de Acoplamento Molecular , Óleos Voláteis , Compostos Fitoquímicos , SARS-CoV-2 , Antivirais/farmacologia , SARS-CoV-2/efeitos dos fármacos , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Eucalyptus/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/análise , Células Vero , Chlorocebus aethiops , Óleo de Eucalipto/farmacologia , Proteases 3C de Coronavírus , Simulação por Computador , Humanos , COVID-19 , Cromatografia Gasosa-Espectrometria de Massas , Monoterpenos/farmacologia , Monoterpenos/análise , Monoterpenos Bicíclicos/farmacologia , Monoterpenos Cicloexânicos , Tratamento Farmacológico da COVID-19 , Glicoproteína da Espícula de Coronavírus , Animais
11.
J AOAC Int ; 107(3): 506-511, 2024 May 02.
Artigo em Inglês | MEDLINE | ID: mdl-38400759

RESUMO

BACKGROUND: Myrcene and cymene, aromatic monoterpenes found in plants and essential oils, possess distinctive aromatic qualities. However, their volatility and limited solubility pose challenges in precise handling and formulation. Meanwhile, nanoemulsions emerge as promising drug delivery systems, improving the bioavailability and stability of these active ingredients. OBJECTIVE: This article aimed to develop an HPLC method for the quantification of two monoterpenoids, p-cymene and myrcene, in nanoemulsions. METHOD: The method used a Phenomenex® Synergi™ Fusion-RP column (150 mm × 4.6 mm id, 4 µm particle size) on an HPLC system with isocratic elution. The mobile phase was composed of acetonitrile and water (60:40, v/v) and was validated in terms of specificity, linearity, accuracy, precision, robustness, and selectivity. RESULTS: The method provided accurate and precise results with a correlation coefficient of 0.999 and RSD values of less than 2%. The method can be used for quality control of nanoemulsions containing these monoterpenoids and as a reference for future studies on their efficacy and stability. CONCLUSIONS: The study demonstrates the feasibility of using HPLC for the quantification of monoterpenoids in nanoemulsions and its potential as a quality control tool for nanoemulsion-based drug delivery systems. HIGHLIGHTS: The method's accuracy, precision, and reliability, as evidenced by high correlation coefficients and low RSD values, underscore its suitability for ensuring the consistent formulation of these monoterpenoid-containing nanoemulsions, while also serving as a reference point for future research endeavors in this field.


Assuntos
Monoterpenos Acíclicos , Alcenos , Cimenos , Emulsões , Monoterpenos , Cromatografia Líquida de Alta Pressão/métodos , Cimenos/química , Cimenos/análise , Emulsões/química , Monoterpenos/análise , Monoterpenos/química , Alcenos/análise , Alcenos/química , Monoterpenos Acíclicos/análise , Monoterpenos Acíclicos/química
12.
Chem Biodivers ; 21(2): e202301949, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38326086

RESUMO

Five new iridoids, valeralides A-E (1-5), two new acyclic monoterpenoids, valeralides F (6) and G (7), together with two known iridoids (8 and 9), were isolated from the roots and rhizomes of Valeriana officinalis var. latifolia. Their structures were elucidated based on 1D and 2D NMR, as well as HR-ESI-MS spectroscopic data. The absolute configuration of compounds 1-4 were elucidated based on electronic circular dichroism (ECD) calculation. In addition, all the isolates were evaluated for their inhibition on nitric oxide production, cytotoxicity and anti-influenza A virus activity.


Assuntos
Rizoma , Valeriana , Estrutura Molecular , Valeriana/química , Iridoides/química , Monoterpenos/análise , Raízes de Plantas/química
13.
Phytochemistry ; 219: 113984, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38266953

RESUMO

Thirty-nine thymol and acetophenone derivatives, including eight pairs of enantiomers, were isolated from the aerial parts of Eupatorium fortunei. Their structures were assigned by detailed analyses of spectroscopic data and NMR calculations based on density functional theory, with 18 ones (1a/1b-14) being previously undescribed compounds. While the absolute configurations of 1a/1b, 2a/2b, 4, 6a/6b, 7, 11a/11b and 15a/15b-18a/18b were established by calculations of electronic circular dichroism data, that of 14 was determined by modified Mosher's method. Compounds 1a/1b and 2a/2b represent a previously unreported type of monoterpenoid dimers via an amide linkage, and compound 3 is a monoterpene-phenylpropanoid hybrid connected through an ester bond. Among the known molecules, the formerly mis-assigned structures of 15a/15b and 22 were revised, and pure natural enantiomers of 16a/16b-18a/18b were reported for the first time. Selective compounds showed antiradical and NO production inhibitory activities in the preliminary biological screening. Compound 31 was further demonstrated to alleviate oxidative stress by activating Nrf2 signaling pathway.


Assuntos
Eupatorium , Eupatorium/química , Monoterpenos/farmacologia , Monoterpenos/análise , Estrutura Molecular , Componentes Aéreos da Planta/química , Acetofenonas/análise
14.
J Agric Food Chem ; 72(4): 1949-1958, 2024 Jan 31.
Artigo em Inglês | MEDLINE | ID: mdl-37172217

RESUMO

Liquid chromatography/high-resolution mass spectrometry (LC/HRMS) can provide identification of grape metabolites which are variety markers. White grapes are poorer in polyphenolics, and the main secondary metabolites which contribute the sensorial characteristics of wines are the glycosidically bound volatile precursors and their aglycones. The profiles of three white grape juices (Pinot grigio, Garganega, and Trebbiano) were characterized by LC/HRMS, and 70 signals of putative glycosidic terpenols, norisoprenoids, and benzenoids were identified. Four signals found only in Pinot grigio corresponded to a norisoprenoid hexose-hexose, 3-oxo-α-ionol (or 3-hydroxy-ß-damascone) rhamnosyl-hexoside, monoterpene-diol hexosyl-pentosyl-hexoside, and hexose-norisoprenoid; three signals were found only in Garganega (putative isopropyl alcohol pentosyl-hexoside, phenylethanol rhamnosyl-hexoside, and norisoprenoid hexose-hexose isomers), and a monoterpenol pentosyl-hexoside isomer only in Trebbiano. These variety markers were then investigated in juice blends of the three varieties. This approach can be used to develop control methods to reveal not-allowed grape varieties and practices in white wines winemaking.


Assuntos
Vitis , Vinho , Frutas/química , Hexoses , Norisoprenoides/análise , Vitis/química , Vinho/análise , Monoterpenos/análise , Monoterpenos/química
15.
Molecules ; 28(23)2023 Nov 24.
Artigo em Inglês | MEDLINE | ID: mdl-38067470

RESUMO

In this study, a validated quality evaluation method with peony flower fingerprint chromatogram combined with simultaneous determination of sixteen bioactive constituents was established using UPLC-DAD-MS/MS. The results demonstrated that the method was stable, reliable, and accurate. The UPLC chemical fingerprints of 12 different varieties of peonies were established and comprehensively evaluated by similarity evaluation (SE), hierarchical cluster analysis (HCA), principal component analysis (PCA), and quantification analysis. The results of SE indicated that similar chemical components were present in these samples regardless of variety, but there were significant differences in the content of chemical components and material basis characteristics. The results of HCA and PCA showed that 12 varieties of samples were divided into two groups. Four flavonoids (11, 12, 13, and 16), five monoterpenes and their glycosides (3, 4, 6, 14, and 15), three tannins (7, 9, and 10), three phenolic acids (1, 2, and 5), and one aromatic acid (8) were identified from sixteen common peaks by standards and liquid chromatography-mass spectrometry (LC-MS). The simultaneous quantification of six types of components was conducted with the 12 samples, it was found that the sum contents of analytes varied obviously for peony flower samples from different varieties. The content of flavonoids, tannins, and monoterpenes (≥19.34 mg/g) was the highest, accounting for more than 78.45% of the total compounds. The results showed that the flavonoids, tannins, and monoterpenes were considered to be the key indexes in the classification and quality assessment of peony flower. The UPLC-DAD-MS/MS method coupled with multiple compounds determination and fingerprint analysis can be effectively applied as a feature distinguishing method to evaluate the compounds in peony flower raw material for product quality assurance in the food, pharmaceutical, and cosmetic industries. Moreover, this study provides ideas for future research and the improvement of products by these industries.


Assuntos
Medicamentos de Ervas Chinesas , Paeonia , Espectrometria de Massas em Tandem/métodos , Paeonia/química , Cromatografia Líquida de Alta Pressão/métodos , Taninos/análise , Medicamentos de Ervas Chinesas/química , Flavonoides/química , Monoterpenos/análise
16.
Molecules ; 28(23)2023 Nov 27.
Artigo em Inglês | MEDLINE | ID: mdl-38067521

RESUMO

Achillea millefolium L. herb and flowers have high biological activity; hence, they are used in medicine and cosmetics. The aim of this study was to perform morpho-anatomical analyses of the raw material, including secretory tissues, histochemical assays of the location of lipophilic compounds, and quantitative and qualitative analysis of essential oil (EO). Light and scanning electron microscopy techniques were used to analyse plant structures. The qualitative analyses of EO were carried out using gas chromatography-mass spectrometry (GC/MS). The results of this study showed the presence of exogenous secretory structures in the raw material, i.e., conical cells (papillae) on the adaxial surface of petal teeth and biseriate glandular trichomes on the surface flowers, bracts, stems, and leaves. Canal-shaped endogenous secretory tissue was observed in the stems and leaves. The histochemical assays revealed the presence of total, acidic, and neutral lipids as well as EO in the glandular trichome cells. Additionally, papillae located at the petal teeth contained neutral lipids. Sesquiterpenes were detected in the glandular trichomes and petal epidermis cells. The secretory canals in the stems were found to contain total and neutral lipids. The phytochemical assays demonstrated that the A. millefolium subsp. millefolium flowers contained over 2.5-fold higher amounts of EO (6.1 mL/kg) than the herb (2.4 mL/kg). The EO extracted from the flowers and herb had a similar dominant compounds: ß-pinene, bornyl acetate, (E)-nerolidol, 1,8-cineole, borneol, sabinene, camphor, and α-pinene. Both EO samples had greater amounts of monoterpenes than sesquiterpenes. Higher amounts of oxygenated monoterpenes and oxygenated sesquiterpenoids were detected in the EO from the herb than from the flowers.


Assuntos
Achillea , Óleos Voláteis , Sesquiterpenos , Óleos Voláteis/química , Achillea/química , Flores/química , Folhas de Planta/química , Sesquiterpenos/análise , Monoterpenos/análise
17.
Molecules ; 28(24)2023 Dec 05.
Artigo em Inglês | MEDLINE | ID: mdl-38138428

RESUMO

Lily is one of the most important cut flowers in the world, with a rich floral fragrance. To further explore the fragrance emission mechanisms of lily cultivars, headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS) and organic solvent extraction-gas chromatography-mass spectrometry (OSE-GC-MS) were used to unveil the volatile organic compounds (VOCs) and endogenous extracts of seven lily cultivars. Furthermore, real-time quantitative PCR (qRT-PCR) was used to determine the expression levels of two key genes (TPS and BSMT) related to the biosynthesis of monoterpenoids and methyl benzoate. The results show that forty-five VOCs were detected in the petals of seven lily cultivars, and the main compounds were monoterpenoids and phenylpropanoids/benzenoids. Dichloromethane was the best solvent for extracting the endogenous extracts of Lilium 'Viviana' petals and eighteen endogenous extracts were detected using dichloromethane to extract the petals of seven lily cultivars. Each compound's emission ratio (natural logarithm of the ratio of VOC content to endogenous extract content) was calculated, and linear regression analyses between emission ratios and boiling points were conducted. Significant linear negative correlations existed between the emission ratios and boiling points of compounds, and the regression equations' coefficients of determination (R2) were all greater than 0.7. TPS was expressed highly in 'Viviana', 'Pink News', and 'Palazzo', and BSMT was expressed highly in 'Pink News' and 'Palazzo'. Correlation analyses between the gene expression levels and the monoterpenoids and methyl benzoate contents found that the TPS expression levels have strong positive correlations with monoterpenoids content, while no correlations were found between the expression levels of BSMT and the contents of methyl benzoate. This study lays the foundation for research on the release patterns of VOCs in the flowers of Lilium, and the breeding of lilies for their floral fragrance.


Assuntos
Lilium , Compostos Orgânicos Voláteis , Lilium/genética , Compostos Orgânicos Voláteis/análise , Cloreto de Metileno , Melhoramento Vegetal , Flores/química , Microextração em Fase Sólida , Solventes/análise , Monoterpenos/análise
18.
Molecules ; 28(21)2023 Oct 26.
Artigo em Inglês | MEDLINE | ID: mdl-37959695

RESUMO

Liverworts contain a large number of biologically active compounds that are synthesised and stored in their oil bodies. However, knowledge about the chemical composition of individual species is still incomplete. The subject of the study was Calypogeia integristipula, a species representing leafy liverworts. Plant material for chemotaxonomic studies was collected from various locations in Poland. The chemical composition was determined in 74 samples collected from the natural environment in 2021 and 2022 in three growing seasons: spring, summer and autumn, and for comparison with samples originating from in vitro culture. The plants were classified as Calypogeia integristipula on the basis of morphological characteristics, oil bodies, and DNA markers. The volatile organic compounds (VOCs) from the biological material were extracted by headspace solid phase microextraction (HS-SPME). The samples were then analysed by gas chromatography-mass spectrometry (GC-MS). A total of 79 compounds were detected, of which 44 compounds were identified. The remaining compounds were described using the MS fragmentation spectrum. Cyclical changes in the composition of compounds associated with the growing season of Calypogeia integristipula were observed. Moreover, samples from in vitro culture and samples taken from the natural environment were shown to differ in the composition of chemical compounds. In terms of quantity, among the volatile compounds, compounds belonging to the sesquiterpene group (46.54-71.19%) and sesqiuterpenoid (8.12-22.11%) dominate. A smaller number of compounds belong to aromatic compounds (2.30-10.96%), monoterpenes (0.01-0.07%), monoterpenoids (0.02-0.33%), and aliphatic hydrocarbons (1.11-6.12%). The dominant compounds in the analysed liverworts were: anastreptene (15.27-31.14%); bicyclogermacrene (6.99-18.09%), 4,5,9,10-dehydro-isolongifolene (2.00-8.72%), palustrol (4.95-9.94%), spathulenol (0.44-5.11%).


Assuntos
Hepatófitas , Compostos Orgânicos Voláteis , Estações do Ano , Cromatografia Gasosa-Espectrometria de Massas/métodos , Monoterpenos/análise , Compostos Orgânicos Voláteis/análise , Microextração em Fase Sólida/métodos
19.
Ecotoxicol Environ Saf ; 268: 115695, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37976932

RESUMO

Widespread use of spray-type consumer products can raise significant concerns regarding their effects on indoor air quality and human health. In this study, we conducted non-target screening using gas chromatography-mass spectrometry (GC-MS) to analyze VOCs in 48 different spray-type consumer products. Using this approach, we tentatively identified a total of 254 VOCs from the spray-type products. Notably, more VOCs were detected in propellant-type products which are mostly solvent-based than in trigger-type ones which are mostly water-based. The VOCs identified encompass various chemical classes including alkanes, cycloalkanes, monoterpenoids, carboxylic acid derivatives, and carbonyl compounds, some of which arouse concerns due to their potential health effects. Alkanes and cycloalkanes are frequently detected in propellant-type products, whereas perfumed monoterpenoids are ubiquitous across all product categories. Among the identified VOCs, 12 compounds were classified into high-risk groups according to detection frequency and signal-to-noise (S/N) ratio, and their concentrations were confirmed using reference standards. Among the identified VOCs, D-limonene was the most frequently detected compound (freq. 21/48), with the highest concentration of 1.80 mg/g. The risk assessment was performed to evaluate the potential health risks associated with exposure to these VOCs. The non-carcinogenic and carcinogenic risks associated with the assessed VOC compounds were relatively low. However, it is important not to overlook the risk faced by occupational exposure to these VOCs, and the risk from simultaneous exposure to various VOCs contained in the products. This study serves as a valuable resource for the identification of unknown compounds in the consumer products, facilitating the evaluation of potential health risks to consumers.


Assuntos
Poluentes Atmosféricos , Cicloparafinas , Compostos Orgânicos Voláteis , Humanos , Poluentes Atmosféricos/análise , Compostos Orgânicos Voláteis/toxicidade , Compostos Orgânicos Voláteis/análise , Cicloparafinas/análise , Alcanos/análise , Monoterpenos/análise , Monitoramento Ambiental/métodos
20.
Chem Biodivers ; 20(12): e202300823, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37917799

RESUMO

Myrtaceae is one of the most diverse and abundant botanical families, exhibiting wide diversity in the chemical composition of essential oils (EOs). EOs have various biotechnological applications such as controlling the populations of organisms that negatively impact humans. This study aimed to extract EOs from Myrtaceae species, chemically characterize them, and evaluate their larvicidal and fungicidal effects. EOs were extracted from the leaves of Eugenia brasiliensis, Eugenia uniflora, Psidium cattleyanum, Psidium guajava, and Syzygium cumini by hydrodistillation for 3 h and characterized by chromatographic analysis. Larvaes of Aedes aegypti and colonies of Fusarium oxysporum were subjected to increasing EO concentrations to determine the larvicidal and fungicidal potential. The EOs of Eugenia and Psidium species are primarily composed of sesquiterpenes (>80 %), whereas S. cumini EO is rich in monoterpenes (more than 60 %). The Eugenia species had similar amounts of oxygenated monoterpenes, which may explain their higher larvicidal potential compared to other species, with CL50 of 86.68 and 147.46 PPM, respectively. In addition to these two study species, S. cumini showed a high inhibition of fungal growth, with more than 65 % inhibition. We demonstrated that the actions of five EOs from Myrtaceae with different biological activities are associated with chemical diversity.


Assuntos
Aedes , Eugenia , Inseticidas , Myrtaceae , Óleos Voláteis , Psidium , Syzygium , Humanos , Animais , Óleos Voláteis/química , Syzygium/química , Psidium/química , Folhas de Planta/química , Monoterpenos/análise , Inseticidas/química , Larva
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