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1.
Food Chem ; 426: 136584, 2023 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-37329800

RESUMO

Food safety concerns caused by the application of spice allergens to fish anaesthesia. In this paper, a chitosan-reduced graphene oxide/polyoxometalates/poly-l-lysine (CS-rGO/P2Mo17Cu/PLL) modified electrode was constructed by electrodeposition and successfully applied to the quantitative analysis of eugenol (EU). The detection limit was 0.4490 µM in the linear range of 2x10-6 M to 1.4x10-5 M. It was applied to the determination of EU residues in kidney, liver and meat tissues of perch with recoveries ranging from 85.43 to 93.60%. Besides, the electrodes demonstrate high stability (2.56% drop in current value after 70 days at room temperature), high reproducibility (RSD of 4.87% for 6 parallel electrodes) and extremely fast response time. This study provided a new material for the electrochemical detection of EU.


Assuntos
Grafite , Percas , Elementos de Transição , Animais , Oxirredução , Eugenol/análise , Reprodutibilidade dos Testes , Grafite/química , Técnicas Eletroquímicas/métodos , Eletrodos , Limite de Detecção
2.
Chem Biodivers ; 20(7): e202300252, 2023 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-37366263

RESUMO

The chemical composition of the volatile fraction of Ocimum gratissimum concrete (romba) from Madagascar has been determined for the first time by GC/MS and GC-FID. A methyl cinnamate chemotype has been determined for this material, along with a set of compounds typical in essential oils and extracts from plants of the Ocimum genus. Variability was mostly observed on terpenes and terpenoids components. GC-O-MS was also used for a sensory evaluation of this material performed by a master perfumer. The chemical composition of this O. gratissimum extract was then compared with literature data to assess subtle differences between chemotypes of the same species and other species of the same genus within natural variability. A mapping illustrates the occurrence of the cinnamate chemotype in Eastern Africa, India and now Madagascar, while other origins generally present eugenol, thymol, camphor, or linalool chemotypes.


Assuntos
Ocimum , Óleos Voláteis , Ocimum/química , Madagáscar , Óleos Voláteis/química , Eugenol/análise , Timol/análise , Óleos de Plantas/química
3.
Reprod Sci ; 30(9): 2591-2614, 2023 09.
Artigo em Inglês | MEDLINE | ID: mdl-37040058

RESUMO

Clove with the scientific name of Syzygium aromaticum (L.) Merr. & L.M. Perry is an evergreen tree in which its buds are used for medicinal purposes. Traditional medicine manuscripts as well as recent studies reported its effects on male and female reproductive systems. The aim of this study is to investigate the reported contradictory effects of clove and its phytochemicals on the reproductive system of both males and females. All types of in vitro, animal, and human studies of clove and its main constituents in the field of reproductive systems were collected via searching electronic databases including PubMed and Scopus from the onset till 2021. In this review, 76 articles were included, of which 25 were related to male reproduction, 32 were related to female reproduction, and 19 were related to reproductive malignancies. Analysis of the literature indicates the effects of clove and its constituents especially eugenol and ß-caryophyllene on the level of sex hormones, fertility, sperm abnormalities, endometriosis, menstrual cycle, as well as gynecological infections, and reproductive tumors. The main mechanism of clove has not been understood yet but it seems that different parameters affect its pharmacological activity including the type of extract, dose, and duration of administration as well as the primary cause of the disorder. According to the effects of clove on different parts of the reproductive system, it seems that it can be a suitable candidate for related disorders, provided that more and more detailed studies are done on it.


Assuntos
Syzygium , Animais , Feminino , Masculino , Humanos , Sementes/química , Eugenol/análise , Reprodução , Genitália/química
4.
Talanta ; 257: 124397, 2023 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-36858010

RESUMO

Gas chromatography-ion mobility spectrometry (GC-IMS) has recently gained increasing attention for the analysis of volatile compounds due to its high sensitivity, selectivity, and robust design. Peak shape distortion, including peak tailing or broadening, are well known challenges in chromatographic analysis that result in peak asymmetry and decreased resolution. However, in IMS analysis peak tailing, which is independent on the column separation technique, have also been observed. As high boiling substances, such as monoterpenes, are mainly affected by enlarged peak tailing in GC-IMS, we propose that condensation or adsorption effects within the "cold" IMS cell, which is commonly operated at 45 °C-90 °C, are the root cause. To avoid condensation and to decrease peak tailing, we used a prototypic high temperature ion mobility spectrometry (HTIMS) in this work, which allows an increase of the IMS drift tube temperature up to 180 °C. This HTIMS was coupled to a GC column separation and used to analyse the peak shape of homologues series of ketones, alcohols, aldehydes, as well as high boiling fragrance compounds, such as monoterpenes and phenylpropanoids. While we were able to show that an increased IMS drift tube temperatures correlates well with improved peak shapes, the GC parameters of the HS-GC-HTIMS method, however, were found to have little effect on the peak shapes in IMS spectra. In particular monoterpenes, which display intense peak tailing at lower IMS drift tube temperatures, show significant improvement of the peak shape at higher IMS drift tube temperatures. This leads to the assumption that high boiling substances indeed undergo condensation effects within the IMS cell at low drift tube temperatures. For many separation tasks, such as the separation of the phenylpropanoids eugenol and isoeugenol, comparably low IMS temperatures of 120 °C are already sufficient to achieve a resolution above 1.5. However, the optimal drift tube temperature is dependent on the substance class. While the aspect ratio increases steadily for most monoterpenes, phenylpropanoids and aldehyde monomer peaks investigated, an optimal aspect ratio was found for ketones between 140 °C and 160 °C and alcohols between 120 °C and 140 °C. Lastly, the change of the reduced mobility K0 with the increase of drift tube temperature was analysed. Compounds with similar chemical structure, such as the alcoholic monoterpenes citronellol and geraniol or the phenylpropanoids eugenol and isoeugenol show similar shifts of the K0 value. Substances which differ in their chemical structure, such as the aldehyde monoterpenes citral and cinnamal have substantially different shifts of the K0 value. With a future large substance database, the temperature dependant slope of the K0 value of a substance could be used to identify the substance groups of unknown molecules. Furthermore, substances with the same drift time but different chemical composition could be separable through a change in drift tube temperature.


Assuntos
Cosméticos , Óleos Voláteis , Eugenol/análise , Temperatura , Cromatografia Gasosa-Espectrometria de Massas/métodos , Alérgenos/análise , Odorantes/análise , Cosméticos/química , Monoterpenos/análise , Álcoois/análise , Aldeídos/análise , Cetonas/análise
5.
Food Chem ; 402: 134160, 2023 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-36194944

RESUMO

Bottling regular wines following aromatized wines on the same filling lines bears the risk of unintentional aroma carryover, which has led to accusations of illegal aromatization. Obeying guidelines of good manufacturing practice, aroma carryover with no sensory relevance shall be considered as a technical unavoidable transfer having no legal consequences. To detect sensory relevance, odor activity values greater than one are proposed. Odor detection thresholds (OTs) were determined in water, model wine, and white wine for three lactones, α-ionone, ethyl 2-methylbutanoate, trans-cinnamaldehyde, and eugenol. Using different matrices OTs varied by factors of 2 for α-ionone and up to 23000 for ethyl 2-methylbutanoate. For α-ionone, being most prone for carryover, the three times higher OT of consumers did not trigger any preference for the aromatized wines, but rejection at 300 µg/L. Assessing α-ionone spiked wines by descriptive analysis, significant changes in sensory attributes only occurred at concentrations 10 times above OT.


Assuntos
Compostos Orgânicos Voláteis , Vinho , Eugenol/análise , Cromatografia Gasosa-Espectrometria de Massas , Lactonas/análise , Odorantes/análise , Compostos Orgânicos Voláteis/análise , Água/análise , Vinho/análise
6.
Arch Microbiol ; 204(11): 674, 2022 Oct 18.
Artigo em Inglês | MEDLINE | ID: mdl-36255521

RESUMO

Spices are widely used in daily life such as diet and have certain activity. Especially in China, spices have been mainly used as condiments for thousands of years in order to improve the sensory quality of food; in addition, they and their derivatives can also be used as preservatives. In this study, three spices with unique Chinese characteristics widely used were selected: cassia bark (bark of Cinnamomum camphora Presl), bay fruits (Laurus nobilis), and cloves (Syzygiumaromaticum). The main components and antibacterial ability of these three spices were analyzed by simulated extraction method. Through headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS) analysis, it was determined that the main active compounds in the essential oils of cassia bark, bay fruits and cloves were cinnamaldehyde (78.11%), cinnamaldehyde (61.78%) and eugenol (75.23%), respectively. The agar plate diffusion test and the simulated food culture medium experiment confirmed that the essential oils extracted from the three flavors have antibacterial effects on Listeria monocytogenes, Listeria innocua, Listeria welshimeri, Listeria ivanovii, Listeria grayi and Vibrio parahaemolyticus. The antibacterial activity of different strains has different optimal extraction conditions. Generally speaking, cinnamon essential oil has the strongest antibacterial activity, while laurel fruit has the lowest antibacterial activity. The study proved the antibacterial activity of these three Chinese-specific spices and provided some new ideas and methods for the subsequent research and preparation of natural food additives and food antibacterial agents.


Assuntos
Antibacterianos , Óleos Voláteis , Óleos de Plantas , Especiarias , Ágar , Antibacterianos/farmacologia , Cassia/química , Cinnamomum aromaticum/química , Eugenol/análise , Aditivos Alimentares , Frutas/química , Óleos Voláteis/farmacologia , Casca de Planta/química , Especiarias/análise , Syzygium/química , Óleos de Plantas/farmacologia
7.
J Agric Food Chem ; 70(38): 12156-12163, 2022 Sep 28.
Artigo em Inglês | MEDLINE | ID: mdl-36112412

RESUMO

White leaf mountain mint, Pycnanthemum albescens Torrey & A. Gray, also known as white mountain mint or white leaved mountain mint, is a species endemic in the American Southeast. In the present study, 24 odorants were identified using solvent-assisted flavor evaporation, aroma extract dilution analysis, and gas chromatography-mass spectrometry. Nine odorants with flavor dilution factors ≥16 were quantitated by stable isotope dilution assays, and odor activity values (OAVs) were calculated. In addition, the enantiomeric proportions of several chiral odorants were determined by chiral chromatography. Odorants with OAV ≥1 included 1,8-cineole (eucalyptus; OAV 9200), myrcene (terpeny; OAV 1400), linalool (floral, citrus; OAV 370), ß-ionone (floral, violet; OAV 64), borneol (earthy; OAV 55), bornyl acetate (earthy, fruity; OAV 19), and eugenol (clove; OAV 3.1). Odor simulation experiments revealed that a mixture of the odorants with OAV ≥1 successfully mimicked the odor of an aqueous extract of the plant when combined in their natural concentrations. This study lays the groundwork for future studies aimed at determining the natural aroma variation within different populations of P. albescens and aids in the future development of selections and hybrids with targeted aroma profiles of commercial interest.


Assuntos
Lamiaceae , Mentha , Compostos Orgânicos Voláteis , Eucaliptol , Eugenol/análise , Aromatizantes/química , Odorantes/análise , Olfatometria , Solventes , Compostos Orgânicos Voláteis/química
8.
J Agric Food Chem ; 70(40): 12916-12924, 2022 Oct 12.
Artigo em Inglês | MEDLINE | ID: mdl-36174191

RESUMO

Conradina verticillata Jennison, commonly known as Cumberland Rosemary, is an endangered plant from the mint family Lamiaceae. This species is a flowering, perennial shrub found only in a few counties in Kentucky and Tennessee. Although the odorants responsible for Cumberland Rosemary's unique aroma have not been previously characterized, in this study, a total of 32 odorants were identified using gas chromatography-olfactometry (GC-O) and gas chromatography-mass spectrometry (GC-MS). Odorant flavor dilution (FD) factors were determined through the application of aroma extract dilution analysis (AEDA). Seven odorants with FD factors ≥64 were quantitated by stable isotope dilution assays (SIDA), and their odor activity values (OAV) were calculated. Odorants with OAV ≥1 included 1-octen-3-one (earthy-mushroom, OAV 2,900,000), 1,8-cineole (eucalyptus, OAV 510,000), borneol (earthy, OAV 10,000), bornyl acetate (earthy-fruity, OAV 3,700), eugenol (spicy, OAV 2,200), menthone (mint, OAV 130), and camphor (herbaceous, OAV 72). Sensory analysis revealed that an odor simulation model based on the quantitative data was a close match to the aroma of the plant. Omission studies determined that 1-octen-3-one, 1,8-cineole, and eugenol were the key odorants critical to Cumberland Rosemary's distinct aroma profile. The stereochemistry of selected odorants was also determined by chiral chromatography. This study established a foundation for future experiments on the aroma chemistry of C. verticillata and the other six members of the Conradina genus.


Assuntos
Lamiaceae , Rosmarinus , Compostos Orgânicos Voláteis , Cânfora/análise , Eucaliptol/análise , Eugenol/análise , Cromatografia Gasosa-Espectrometria de Massas , Cetonas , Odorantes/análise , Olfatometria , Compostos Orgânicos Voláteis/química
9.
BMC Plant Biol ; 22(1): 395, 2022 Aug 09.
Artigo em Inglês | MEDLINE | ID: mdl-35945501

RESUMO

BACKGROUND: Mei (Prunus mume) is the only woody plant in the genus Prunus with a floral fragrance, but the underlying mechanisms of aroma compound biosynthesis are unclear despite being a matter of considerable interest. RESULTS: The volatile contents of the petals of two cultivars with significantly different aromas, Prunus mume 'Xiao Lve' and Prunus mume 'Xiangxue Gongfen', were characterised by GC-MS at different flowering periods, and a total of 44 volatile compounds were detected. Among these, the main substances forming the typical aroma of P. mume were identified as eugenol, cinnamyl acetate, hexyl acetate and benzyl acetate, with variations in their relative concentrations leading to sensory differences in the aroma of the two cultivars. We compiled a transcriptome database at key stages of floral fragrance formation in the two cultivars and used it in combination with differential analysis of floral volatiles to construct a regulatory network for the biosynthesis of key aroma compounds. The results indicated that PmPAL enzymes and PmMYB4 transcription factors play important roles in regulating the accumulation of key biosynthetic precursors to these compounds. Cytochrome P450s and short-chain dehydrogenases/reductases might also influence the biosynthesis of benzyl acetate by regulating production of key precursors such as benzaldehyde and benzyl alcohol. Furthermore, by analogy to genes with verified functions in Arabidopsis, we predicted that three PmCAD genes, two 4CL genes, three CCR genes and two IGS genes all make important contributions to the synthesis of cinnamyl acetate and eugenol in P. mume. This analysis also suggested that the downstream genes PmBGLU18-like, PmUGT71A16 and PmUGT73C6 participate in regulation of the matrix-bound and volatile states of P. mume aroma compounds. CONCLUSIONS: These findings present potential new anchor points for further exploration of floral aroma compound biosynthesis pathways in P. mume, and provide new insights into aroma induction and regulation mechanisms in woody plants.


Assuntos
Prunus , Eugenol/análise , Eugenol/metabolismo , Perfilação da Expressão Gênica , Odorantes/análise , Prunus/genética , Prunus/metabolismo , Transcriptoma
10.
Inhal Toxicol ; 34(11-12): 319-328, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-35913821

RESUMO

Aim: The cardiovascular toxicity of unheated and heated flavorants and their products as commonly present in electronic cigarette liquids (e-liquids) was evaluated previously in vitro. Based on the results of in vitro assays, cinnamaldehyde, eugenol, menthol, and vanillin were selected to conduct a detailed chemical analysis of the aerosol generated following heating of each compound both at 250 and 750 °C. Materials and Methods: Each flavoring was heated in a drop-tube furnace within a quartz tube. The combustion atmosphere was captured using different methods to enable analysis of 308 formed compounds. Volatile organic compounds (VOCs) were captured with an evacuated Summa canister and assayed via gas chromatography interfaced with mass spectrometry (GC-MS). Carbonyls (aldehydes and ketones) were captured using a 2,4-dinitrophenylhydrazine (DNPH) cartridge and assayed via a high-performance liquid chromatography-ultra-violet (HPLC-UV) assay. Polyaromatic hydrocarbons (PAHs) were captured using an XAD cartridge and filter, and extracts were assayed using GC-MS/MS. Polar compounds were assayed after derivatization of the XAD/filter extracts and analyzed via GC-MS. Conclusion: At higher temperature, both cinnamaldehyde and menthol combustion significantly increased formaldehyde and acetaldehyde levels. At higher temperature, cinnamaldehyde, eugenol, and menthol resulted in increased benzene concentrations. At low temperature, all four compounds led to higher levels of benzoic acid. These data show that products of thermal degradation of common flavorant compounds vary by flavorant and by temperature and include a wide variety of harmful and potentially harmful constituents (HPHCs).


Assuntos
Aerossóis , Sistemas Eletrônicos de Liberação de Nicotina , Aromatizantes , Temperatura Alta , Produtos do Tabaco , Acetaldeído/análise , Acroleína/análise , Aerossóis/química , Benzeno/análise , Ácido Benzoico/análise , Eugenol/análise , Formaldeído/análise , Cetonas/análise , Mentol/análise , Espectrometria de Massas em Tandem , Produtos do Tabaco/análise , Compostos Orgânicos Voláteis/análise , Aromatizantes/química
11.
Biochim Biophys Acta Biomembr ; 1864(11): 184035, 2022 11 01.
Artigo em Inglês | MEDLINE | ID: mdl-35987463

RESUMO

Dehydrodieugenol, a neolignan isolated from the Brazilian plant Nectandra leucantha (Lauraceae) with reported antiprotozoal and anticancer activity, was incorporated in Langmuir monolayers of selected lipids as cell membrane models, aiming to comprehend its action mechanism at the molecular level. The interaction of this compound with the lipids dipalmitoylphosphatidylcholine (DPPC), dipalmitoylphosphatidylethanolamine (DPPE), dipalmitoylphosphatidylserine (DPPS), and dipalmitoylphosphatidylglycerol (DPPG) was inferred through tensiometry, infrared spectroscopy, and Brewster angle microscopy. The interactions had different effects depending on the chemical nature of the lipid polar head, with expansion for DPPC monolayers, condensation for DPPE, and expansion (at low surface pressures) followed by the overlap of the isotherms (at high surface pressure values) for DPPS and DPPG. Effects caused by dehydrodieugenol in the negatively charged lipids were distinctive, which was also reflected in the hysteresis assays, surface potential-area isotherms, and rheological measurements. Infrared spectroscopy indicated that the drug interaction with the monolayer affects not only the polar groups, but also the acyl lipid chains for all lipids. These results pointed to the fact that the interaction of the drug with lipid monolayers at the air-water interface is modulated by the lipid composition, mainly considering the polar head of the lipids, as well as the hydrophobicity of the lipids and the drug. As negatively charged lipids pointed to distinctive interaction, we believe this can be related to the antiprotozoal and anticancer properties of the compound.


Assuntos
Lauraceae , Lignanas , Membrana Celular/química , Eugenol/análogos & derivados , Eugenol/análise , Lignanas/análise
12.
Molecules ; 27(9)2022 Apr 27.
Artigo em Inglês | MEDLINE | ID: mdl-35566129

RESUMO

Ocimum campechianum Mill. (Peruvian basil) is an essential oil-bearing plant of the Lamiaceae family. Volatile oil produced through steam distillation of Peruvian basil was examined to establish the aromatic and stable isotope profiles of samples (n = 9) from three different cultivated plots in Peru. The resulting essential oils were analyzed by GC/FID, GC/MS, and GC/IRMS. In accordance with findings from other researchers, multiple chemotypes, defined by the most abundant aromatic compounds, exist within these populations. Overall, 55% of samples are the eugenol chemotype (values ranging 15.4-30.2%), 33% are the methyl eugenol chemotype (values ranging 68.1-68.7%), and a single sample is a mixture of both chemotypes, containing high levels of both eugenol (38.1%) and methyl eugenol (8.6%). Stable isotope ratios, δ2H and δ13C, performed on prominent compounds provide supporting data for distinguishing chemotypes. Complete aromatic profiles, stable isotope ratios, and essential oil yield are established for each sample. This study confirms the existence of multiple chemotypes and, for the first time, to the author's best knowledge, establishes stable isotope ratios for O. campechianum essential oil, which proves a useful tool in further investigating plant metabolism and determining essential oil authenticity.


Assuntos
Lamiaceae , Ocimum basilicum , Ocimum , Óleos Voláteis , Eugenol/análise , Isótopos , Peru , Óleos de Plantas/análise
13.
Bol. latinoam. Caribe plantas med. aromát ; 21(2): 207-214, mar. 2022. tab
Artigo em Inglês | LILACS | ID: biblio-1395229

RESUMO

In this study, we investigated the main constituent, the predominant class and biological activity of the essential oil extracted from the leaves of Pimenta dioica and the pattern of the major constituent against larvae in the third stage of Aedes aegypti. For this reason, we extracted the oil by hydrodistillation, identified its components by gas chromatography coupled with mass spectrometry (GC/MS) and calculated the lethal concentration (LC50) of the larvicidal activity using the Reed-Muench method. The results show that the oil consists mainly of eugenol, in which the phenylpropanoid class predominated and the lethal concentration, LC50, was 38.86 µg mL-1at a confidence level of 2.25 µg mL-1, while the eugenol standard presented LC5079.75 µg mL-1at a confidence level of 2.10 µg mL-1. Given the facts, we conclude that the oil is more active than the standard and that it has the potential to replace chemical larvicides.


En este estudio, investigamos el constituyente principal, la clase predominante y la actividad biológica del aceite esencial extraído de las hojas de Pimenta dioica y el patrón del constituyente principal contra las larvas en la tercera etapa de Aedes aegypti. Por este motivo, extrajimos el aceite por hidrodestilación, identificamos sus componentes mediante cromatografía de gases acoplada a espectrometría de masas (GC/MS) y calculamos la concentración letal (CL50) de la actividad larvicida mediante el método Reed-Muench. Los resultados muestran que el aceite está constituido principalmente por eugenol, en el que predominó la clase fenilpropanoide y la concentración letal, CL50, fue de 38,86 µg.mL-1 a un nivel de confianza de 2,25 µg.mL-1, mientras que el estándar de eugenol presentó CL50 79,75 µg.mL -1 a un nivel de confianza de 2,10 µg.mL-1. Dados los hechos, concluimos que el aceite es más activo que el estándar y que tiene el potencial de reemplazar los larvicidas químicos.


Assuntos
Óleos Voláteis/farmacologia , Óleos Voláteis/química , Aedes/efeitos dos fármacos , Pimenta/química , Larvicidas , Bioensaio , Produtos Biológicos , Eugenol/análise , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Folhas de Planta , Monoterpenos/análise , Larva , Cromatografia Gasosa-Espectrometria de Massas
14.
Chem Pharm Bull (Tokyo) ; 70(1): 37-42, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-34980731

RESUMO

Eugenols (Eugs) such as eugenol (Eug), methyleugenol (MeEug), and linalool (Lin) in basil product are the main bioactive components of basil products and have a terminal double-bond. A sensitive HPLC-fluorescence method for Eugs derivatized with 4-(4,5-diphenyl-1H-imidazol-2-yl)iodobenzene (DIBI) was developed. Good separation of DIB-Eugs was achieved within 20 min on an Atlantis T3 column (50 × 2.1 mm i.d., 3 µm) with a mobile phase of methanol-water. The calibration curves obtained with Eug standards showed good linearities in the range of 0.1-50 µM (r ≥ 0.999). The limits of detection at a signal-to-noise ratio (S/N) = 3 for Eug, MeEug, and Lin were 1.0, 6.0, and 4.8 nM, respectively. The limits of quantitation (S/N = 10) of the Eugs were lower than 19.9 nM. The accuracies for the Eugs were within 96.8-104.6%. The intra- and inter-day precisions as relative standard deviations for the Eugs were less than 1.2 and 9.6% (n = 3). The recoveries of Eug, MeEug, and Lin were 99.0 ± 0.1, 98.0 ± 0.2, and 96.0 ± 0.4% (n = 3), respectively. The DIB-Eugs were confirmed to be stable for 2 h (>90%) at room temperature and 24 h (>95%) at 4 °C. These parameters of the proposed method were useful for the simultaneous determination of Eugs in basil products. Therefore, the developed method may be a powerful tool for the quality evaluation of dried commercially available basil products.


Assuntos
Eugenol/análise , Fluorescência , Ocimum basilicum/química , Cromatografia Líquida de Alta Pressão , Imidazóis/análise , Iodobenzenos/análise , Estrutura Molecular
15.
J Sci Food Agric ; 102(8): 3325-3335, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-34820846

RESUMO

BACKGROUND: Terpene, eugenol and polyphenolic contents of basil are major determinants of quality, which is affected by genetics, weather, growing practices, pests and diseases. Here, we aimed to develop a simple predictive analytical method for determining the polyphenol, eugenol and terpene content of the leaves of major Israeli sweet basil cultivars grown hydroponically, as a function of harvest time, through the use of near-infrared (NIR) spectroscopy, liquid/gas chromatography, and chemometric methods. We also wanted to identify the harvest time associated with the highest terpene, eugenol and polyphenol content. RESULTS: Six different cultivars and four different harvest times were analyzed. Partial least square regression (PLS-R) analysis yielded an accurate, predictive model that explained more than 93% of the population variance for all of the analyzed compounds. The model yielded good/excellent prediction (R2 > 0.90, R2 cv and R2 pre > 0.80) and very good residual predictive deviation (RPD > 2) for all of the analyzed compounds. Concentrations of rosmarinic acid, eugenol and terpenes increased steadily over the first 3 weeks, peaking in the fourth week in most of the cultivars. Our PLS-discriminant analysis (PLS-DA) model provided accurate harvest classification and prediction as compared to cultivar classification. The sensitivity, specificity and accuracy of harvest classification were larger than 0.82 for all harvest time points, whereas the cultivar classification, resulted in sensitivity values lower than 0.8 in three cultivars. CONCLUSION: The PLS-R model provided good predictions of rosmarinic acid, eugenol and terpene content. Our NIR coupled with a PLS-DA demonstrated reasonable solution for harvest and cultivar classification. © 2021 Society of Chemical Industry.


Assuntos
Ocimum basilicum , Quimiometria , Cromatografia Gasosa , Eugenol/análise , Ocimum basilicum/química , Polifenóis/análise , Espectroscopia de Luz Próxima ao Infravermelho/métodos , Terpenos/análise
16.
Artigo em Inglês | MEDLINE | ID: mdl-34339956

RESUMO

Ylang-ylang (YY) essential oil (EO) is distilled from the fresh-mature flowers of the Annonaceae family tropical tree Cananga odorata [Lam.] Hook. f. & Thomson, and is widely used in perfume and cosmetic industries for its fragrant character. Herein, two different metabolomic profiles obtained using high-performance thin-layer chromatography (HPTLC), applying different stains, namely 2,2-diphenyl-1-picrylhydrazyl (DPPH·) and p-anisaldehyde, were used for discrimination of 52 YY samples across geographical origins and distillation grades. The first profile is developed using the DPPH· stain based on the radical scavenging activity (RSA) of YY EOs. Results of the HPTLC-DPPH· assay confirmed that RSA of YY EOs is in proportion to the length of distillation times. Major components contributing to the RSA of YY EOs were tentatively identified as germacrene D and α-farnesene, eugenol and linalool, by gas chromatography-mass spectrometry (GC-MS) and GC-flame ionisation detector (GC-FID). The second profile was developed using the general-purpose p-anisaldehyde stain based on the general chemical composition of YY EOs. Untargeted metabolomic discrimination of YY EOs from different geographical origins was performed based on the HPTLC-p-anisaldehyde profiles, followed by principal component analysis (PCA). A discrimination and prediction model for identification of YY distillation grade was developed using PCA and partial least squares regression (PLS) based on binned HPTLC-ultraviolet (254 nm) profiles, which was successfully applied to distillation grade determination of blended YY Complete EOs.


Assuntos
Cananga/química , Cromatografia em Camada Delgada/métodos , Sequestradores de Radicais Livres/química , Óleos Voláteis/química , Óleos de Plantas/química , Compostos de Bifenilo/análise , Compostos de Bifenilo/metabolismo , Cromatografia Líquida de Alta Pressão , Destilação , Eugenol/análise , Eugenol/química , Eugenol/metabolismo , Sequestradores de Radicais Livres/metabolismo , Metabolômica , Análise Multivariada , Óleos Voláteis/metabolismo , Picratos/análise , Picratos/metabolismo , Óleos de Plantas/metabolismo , Sesquiterpenos/análise , Sesquiterpenos/química , Sesquiterpenos/metabolismo
17.
Molecules ; 26(13)2021 Jul 02.
Artigo em Inglês | MEDLINE | ID: mdl-34279396

RESUMO

The main strategies against Triatoma infestans (primary vector responsible for the Chagas disease transmission) are the elimination or reduction of its abundance in homes through the application of insecticides or repellents with residual power, and environmental management through the improvement of housing. The use of plant-derived compounds as a source of therapeutic agents (i.e., essential oils from aromatic plants and their components) is a valuable alternative to conventional insecticides and repellents. Essential oil-based insect repellents are environmentally friendly and provide reliable personal protection against the bites of mosquitoes and other blood-sucking insects. This study investigates, for the first time to our knowledge, the potential repellent activity of Zuccagnia punctata essential oil (ZEO) and poly(ε-caprolactone) matrices loaded with ZEO (ZEOP) prepared by solvent casting. The analysis of its essential oil from aerial parts by GC-FID and GC-MS, MS allowed the identification of 25 constituents representing 99.5% of the composition. The main components of the oil were identified as (-)-5,6-dehydrocamphor (62.4%), alpha-pinene (9.1%), thuja-2, 4 (10)-diene (4.6%) and dihydroeugenol (4.5%). ZEOP matrices were homogeneous and opaque, with thickness of 800 ± 140 µm and encapsulation efficiency values above 98%. ZEO and ZEOP at the lowest dose (0.5% wt./wt., 96 h) showed a repellency of 33 and 73% respectively, while at the highest dose (1% wt./wt., 96 h) exhibited a repellent activity of 40 and 66 %, respectively. On the other hand, until 72 h, ZEO showed a strong repellent activity against T. infestans (88% repellency average; Class V) to both concentrations, compared with positive control N-N diethyl-3-methylbenzamide (DEET). The essential oils from the Andean flora have shown an excellent repellent activity, highlighting the repellent activity of Zuccagnia punctata. The effectiveness of ZEO was extended by its incorporation in polymeric systems and could have a potential home or peridomiciliary use, which might help prevent, or at least reduce, Chagas' disease transmission.


Assuntos
Fabaceae/química , Repelentes de Insetos/farmacologia , Mosquitos Vetores/efeitos dos fármacos , Óleos Voláteis/farmacologia , Triatoma/efeitos dos fármacos , Animais , Cânfora/análogos & derivados , Cânfora/análise , Eugenol/análogos & derivados , Eugenol/análise , Repelentes de Insetos/química , Óleos Voláteis/química , Poliésteres/química
18.
J Sep Sci ; 44(16): 3146-3157, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-34101986

RESUMO

Divya-Swasari-Vati is a calcium containing polyherbal ayurvedic medicine prescribed for the lung-related ailments observed in the current pandemic of Severe Acute Respiratory Syndrome Coronavirus 2 infections. The formulation is a unique quintessential blend of nine herbs cited in Ayurvedic texts for chronic cough and lung infection. Analytical standardization of herbal medicines is the pressing need of the hour to ascertain the quality compliance. This persuaded us to develop a simple, rapid, and selective high-performance thin-layer chromatographic method for Divya-Swasari-Vati quality standardization. The developed method was validated for the quantification of marker components, gallic acid, cinnamic acid, piperine, eugenol and glycyrrhizin, against reference standards in five different batches of Divya-Swasari-Vati. The analytes were identified by visualization at 254 nm, and by matching their retention factor with authentic standards. The developed method was validated as per the guidelines recommended by the International Council for Harmonization for parameters like, linearity, limit of detection, limit of quantification, accuracy, and precision. Therefore, the developed novel high-performance thin-layer chromatographic process could be employed for rapid standardization of Divya-Swasari-Vati and other related herbal formulation, which would aid in quality manufacturing and product development.


Assuntos
Alcaloides/análise , Benzodioxóis/análise , Cinamatos/análise , Eugenol/análise , Ácido Gálico/análise , Ácido Glicirrízico/análise , Piperidinas/análise , Extratos Vegetais/análise , Alcamidas Poli-Insaturadas/análise , Alcaloides/uso terapêutico , Benzodioxóis/uso terapêutico , Cromatografia em Camada Delgada , Cinamatos/uso terapêutico , Eugenol/uso terapêutico , Ácido Gálico/uso terapêutico , Ácido Glicirrízico/uso terapêutico , Humanos , Pneumopatias/tratamento farmacológico , Ayurveda , Estrutura Molecular , Piperidinas/uso terapêutico , Extratos Vegetais/uso terapêutico , Plantas Medicinais/química , Alcamidas Poli-Insaturadas/uso terapêutico
19.
Molecules ; 26(6)2021 Mar 17.
Artigo em Inglês | MEDLINE | ID: mdl-33802719

RESUMO

Plant diseases reduce crop yield and quality, hampering the development of agriculture. Fungicides, which restrict chemical synthesis in fungi, are the strongest controls for plant diseases. However, the harmful effects on the environment due to continued and uncontrolled utilization of fungicides have become a major challenge in recent years. Plant-sourced fungicides are a class of plant antibacterial substances or compounds that induce plant defenses. They can kill or inhibit the growth of target pathogens efficiently with no or low toxicity, they degrade readily, and do not prompt development of resistance, which has led to their widespread use. In this study, the growth inhibition effect of 24 plant-sourced ethanol extracts on rice sprigs was studied. Ethanol extract of gallnuts and cloves inhibited the growth of bacteria by up to 100%. Indoor toxicity measurement results showed that the gallnut and glove constituents inhibition reached 39.23 µg/mL and 18.82 µg/mL, respectively. Extract treated rice sprigs were dry and wrinkled. Gallnut caused intracellular swelling and breakage of mitochondria, disintegration of nuclei, aggregation of protoplasts, and complete degradation of organelles in hyphae and aggregation of cellular contents. Protection of Rhizoctonia solani viability reached 46.8% for gallnut and 37.88% for clove in water emulsions of 1000 µg/mL gallnut and clove in the presence of 0.1% Tween 80. The protection by gallnut was significantly stronger than that of clove. The data could inform the choice of plant-sourced fungicides for the comprehensive treatment of rice sprig disease. The studied extract effectively protected rice sprigs and could be a suitable alternative to commercially available chemical fungicides. Further optimized field trials are needed to effectively sterilize rice paddies.


Assuntos
Misturas Complexas/farmacologia , Oryza/efeitos dos fármacos , Extratos Vegetais/farmacologia , Rhizoctonia/efeitos dos fármacos , Rhus/química , Syzygium/química , Cromatografia por Troca Iônica , Misturas Complexas/toxicidade , Etanol/química , Eugenol/análise , Fungicidas Industriais/farmacologia , Ácidos Láuricos/análise , Espectrometria de Massas , Microscopia Eletrônica de Varredura , Microscopia Eletrônica de Transmissão , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/ultraestrutura , Micélio/efeitos dos fármacos , Micélio/ultraestrutura , Oryza/microbiologia , Doenças das Plantas/microbiologia , Extratos Vegetais/toxicidade
20.
Molecules ; 26(7)2021 Apr 03.
Artigo em Inglês | MEDLINE | ID: mdl-33916710

RESUMO

A wide range of analytical techniques are reported for the determination of cinnamaldehyde (CCHO) and eugenol (EOH) in plant extracts and herbal formulations either alone or in combination. Nevertheless, sustainable/green analytical techniques for the estimation of CCHO and EOH either alone or in combination are scarce in the literature. Accordingly, the present research was carried out to establish a rapid, highly sensitive, and sustainable high-performance thin-layer chromatography (HPTLC) technique for the simultaneous estimation of CCHO and EOH in the traditional and ultrasound-assisted methanolic extracts of Cinnamomum zeylanicum,C. burmannii, and C. cassia and their essential oils. The simultaneous estimation of CCHO and EOH was performed through NP-18 silica gel 60 F254S HPTLC plates. The cyclohexane/ethyl acetate (90:10, v v-1) solvent system was optimized as the mobile phase for the simultaneous estimation of CCHO and EOH. The greenness score of the HPTLC technique was predicted using AGREE software. The entire analysis was carried out at a detection wavelength of 296 nm for CCHO and EOH. The sustainable HPTLC technique was observed as linear in the range 10-2000 ng band-1 for CCHO and EOH. The proposed technique was found to be highly sensitive, rapid, accurate, precise, and robust for the simultaneous estimation of CCHO and EOH. The content of CCHO in traditional methanolic extracts of C. zeylanicum,C. burmannii, and C. cassia was found to be 96.36, 118.49, and 114.18 mg g-1, respectively. However, the content of CCHO in ultrasound-assisted methanolic extracts of C. zeylanicum,C. burmannii, and C. cassia was found to be 111.57, 134.39, and 129.07 mg g-1, respectively. The content of CCHO in essential oils of C. zeylanicum,C. burmannii, and C. cassia was found to be 191.20, 214.24, and 202.09 mg g-1, respectively. The content of EOH in traditional methanolic extracts of C. zeylanicum,C. burmannii, and C. cassia was found to be 73.38, 165.41, and 109.10 mg g-1, respectively. However, the content of EOH in ultrasound-assisted methanolic extracts of C. zeylanicum,C. burmannii, and C. cassia was found to be 87.20, 218.09, and 121.85 mg g-1, respectively. The content of EOH in essential oils of C. zeylanicum,C. burmannii, and C. cassia was found to be 61.26, 79.21, and 69.02 mg g-1, respectively. The amounts of CCHO and EOH were found to be significantly higher in ultrasound-assisted extracts of all species compared to its traditional extraction and hence ultrasound extraction has been proposed as a superior technique for the extraction of CCHO and EOH. The AGREE analytical score of the present analytical technique was predicted as 0.75, suggesting excellent greenness profile of the proposed analytical technique. Based on all these observations and results, the proposed sustainable HPTLC technique can be successfully used for the simultaneous estimation of CCHO and EOH in different plant extracts and herbal products.


Assuntos
Acroleína/análogos & derivados , Cromatografia em Camada Delgada , Cinnamomum zeylanicum/química , Eugenol/análise , Química Verde , Óleos Voláteis/química , Extratos Vegetais/química , Ultrassom , Acroleína/análise , Análise dos Mínimos Quadrados , Padrões de Referência , Análise de Regressão , Reprodutibilidade dos Testes , Espectrofotometria Ultravioleta
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