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1.
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
2.
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
3.
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
4.
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
5.
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
6.
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
7.
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
8.
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
9.
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
10.
Food Res Int ; 174(Pt 1): 113601, 2023 12.
Artigo em Inglês | MEDLINE | ID: mdl-37986463

RESUMO

Low temperature is the commonly used technique for maintaining the quality of table grapes during postharvest storage. However, this technique could strongly affect the aromatic flavor of fruit. Monoterpenes are the key compounds contributing to the Muscat aromas of grapes. The detailed information and molecular mechanisms underlying the changes in monoterpenes during postharvest low temperature storage have not been thoroughly characterized. In this study, the effects of low temperature storage on the free and bound monoterpene profiles in four cultivars of table grape were determined at both the transcriptomic and metabolomic levels. A total of 27 compounds in both free and bound forms were identified in the four cultivars and showed quantitative differences between the cultivars. Hierarchical cluster and principal component analysis indicated that the free and bound monoterpene profiles were remarkably affected by the low temperature storage. The monoterpenes in the same biosynthesis pathway were clustered together and showed similar evolution trends during low temperature storage. And the content of most of free monoterpenes underwent a rapid decline during low-temperature storage at a certain stage, but the time was different in 4 grape cultivars. Transcriptomic analysis revealed that the expression of DXS, HDR, GPPS and TPS genes involved in the monoterpene synthesis pathway were consistent with the changes in the accumulation of monoterpene compounds. While the expression of HMGS, HMGR genes in MVA pathway and branch genes GGPPS and FPPS were negatively correlated with the accumulation of monoterpenes. The findings provide new insights into the underlying mechanisms of the berry aroma flavor change during low temperature storage.


Assuntos
Monoterpenos , Vitis , Monoterpenos/análise , Vitis/genética , Vitis/metabolismo , Transcriptoma , Temperatura , Odorantes/análise
11.
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
12.
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
13.
Chem Biodivers ; 20(12): e202300827, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37884443

RESUMO

This work aimed to investigate the variability of the chemical composition of the aromatic halophyte Crithmum maritimum L. essential oils according to the geographical origin and separated organs, using a statistical approach based on the multiple analysis of variance and the Principal Component Analyses. One hundred twenty samples were collected from three distinct bioclimatic regions (10 samples×3 provenances×4 organs). Hydrodistillation of separated organs (roots, stems, leaves and flowers) yielded 0.13 to 1.75 % of the dry matter. Chemical investigation of the volatile compounds by Gas chromatography-mass spectrometry showed that C. maritimum essential oils were dominated by monoterpenes hydrocarbons, oxygenated monoterpenes, and phenylpropanoids varying, respectively, from 33.3 to 66.9, from 7.8 to 46.6 and from 4.5 to 57.2 % according to organs and localities. Statistical analyses identified three different chemotypes depending on the geographic origin as follow: γ-Terpinene-Thymol methyl ether / Dillapiole / Thymol methyl ether-Dillapiole.


Assuntos
Apiaceae , Éteres Metílicos , Óleos Voláteis , Timol , Óleos Voláteis/química , Apiaceae/química , Monoterpenos/análise
14.
Chem Biodivers ; 20(11): e202301098, 2023 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-37782764

RESUMO

In this study, the composition of the volatile oils obtained from the fruits of 8 Ferulago species (Ferulago cassia Boiss., F. isaurica Pesmen, F. humilis Boiss., F. macrosciadia Boiss. & Balansa, F. setifolia K.Koch, F. silaifolia (Boiss.) Boiss., F. syriaca Boiss., F. trojana Akalin & Pimenov) growing naturally in Türkiye were examined by means of GC/MS and GC-FID and α-pinene was determined to be present in the fruits of four species along with other monoterpenes as major components. Principal Component Analyses (PCA) and Hierarchical Cluster Analysis (HCA) was performed, utilizing ten major components in the eight essential oils. Also, a Venn diagram was used to demonstrate chemotaxonomical variations in the composition of the essential oils of eight Ferulago species.


Assuntos
Apiaceae , Óleos Voláteis , Frutas/química , Monoterpenos/análise , Cromatografia Gasosa-Espectrometria de Massas , Cromatografia Gasosa
15.
Molecules ; 28(14)2023 Jul 11.
Artigo em Inglês | MEDLINE | ID: mdl-37513200

RESUMO

Zangju (Citrus reticulata cv. Manau Gan) is the main citrus cultivar in Derong County, China, with unique aroma and flavour characteristics, but the use of Zangju peel (CRZP) is limited due to a lack of research on its peel. In this study, electronic nose, headspace-gas chromatography-ion mobility spectrometry (HS-GC-IMS), and partial least squares-discriminant analysis (PLS-DA) methods were used to rapidly and comprehensively evaluate the volatile compounds of dried CRZP and to analyse the role of dynamic changes at different maturation stages. The results showed that seventy-eight volatile compounds, mainly aldehydes (25.27%) and monoterpenes (55.88%), were found in the samples at four maturity stages. The contents of alcohols and aldehydes that produce unripe fruit aromas are relatively high in the immature stage (October to November), while the contents of monoterpenoids, ketones and esters in ripe fruit aromas are relatively high in the full ripening stage (January to February). The PLS-DA model results showed that the samples collected at different maturity stages could be effectively discriminated. The VIP method identified 12 key volatile compounds that could be used as flavour markers for CRZP samples collected at different maturity stages. Specifically, the relative volatile organic compounds (VOCs) content of CRZP harvested in October is the highest. This study provides a basis for a comprehensive understanding of the flavour characteristics of CRZP in the ripening process, the application of CRZP as a byproduct in industrial production (food, cosmetics, flavour and fragrance), and a reference for similar research on other C. reticulata varieties.


Assuntos
Citrus , Compostos Orgânicos Voláteis , Nariz Eletrônico , Citrus/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Álcoois/análise , Aldeídos/análise , Aromatizantes/análise , Monoterpenos/análise , Compostos Orgânicos Voláteis/análise
16.
J Nat Med ; 77(4): 792-816, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37432536

RESUMO

Peony root is an important herbal drug used as an antispasmodic analgesic. To evaluate peony roots with different botanical origins, producing areas, and post-harvest processing, 1H NMR-based metabolomics analysis was employed. Five types of monoterpenoids, including albiflorin (4), paeoniflorin (6), and sulfonated paeoniflorin (25), and six other compounds, including 1,2,3,4,6-penta-O-galloyl-ß-D-glucose (18), benzoic acid (21), gallic acid (22), and sucrose (26) were detected in the extracts of peony root samples. Among them, compounds 4, 6, 18, and total monoterpenoids including 21 were quantified by quantitative 1H NMR (qHNMR). Compound 25 was detected in 1H NMR spectra of sulfur-fumigated white peony root (WPR) extracts indicating that 1H NMR was a fast and effective method for identifying sulfur-fumigated WPR. The content of 26, the main factor affecting extract yield, increased significantly in peony root after low-temperature storage for one month, whereas that in WPR did not increase due to the boiling treatment after harvesting. We investigated the impact of preprocessing methods to such analysis for NMR data from commercial samples, resulting that the data matrix transformed from qHNMR spectra and normalized to internal standard were optimum for multivariate analysis. The multivariate analysis demonstrated that among commercial samples derived from P. lactiflora, peony root samples in Japanese market (PR) had high contents of 18 and 22, and red peony root (RPR) samples had high content of monoterpenoids represented by 6; and among RPR samples, those derived from P. veitchii showed higher contents of 18 and 22 than those from P. lactiflora. The 1H NMR-based metabolomics method coupled with qHNMR was useful for evaluation of peony root and would be applicable for other crude drugs.


Assuntos
Paeonia , Extratos Vegetais , Espectroscopia de Ressonância Magnética , Extratos Vegetais/análise , Monoterpenos/análise , Paeonia/química , Enxofre/análise , Metabolômica , Análise Multivariada , Raízes de Plantas/química
17.
Molecules ; 28(12)2023 Jun 16.
Artigo em Inglês | MEDLINE | ID: mdl-37375358

RESUMO

The genus Thymus L., belonging to the Lamiaceae family, contains about 220 species with a distribution that mainly extends in Europe, northwest Africa, Ethiopia, Asia, and southern Greenland. Due to their excellent biological properties, fresh and/or dried leaves and aerial parts of several Thymus ssp. have been utilized in the traditional medicine of many countries. To evaluate not only the chemical aspects but also the biological properties, the essential oils (EOs), obtained from the pre-flowering and flowering aerial parts of Thymus richardii subsp. nitidus (Guss.) Jalas, endemic to Marettimo Island (Sicily, Italy), were investigated. The chemical composition of the EOs, obtained by classical hydrodistillation and GC-MS and GC-FID analyses, showed the occurrence of similar amounts of monoterpene hydrocarbons, oxygenated monoterpenes, and sesquiterpene hydrocarbons. The main constituents of the pre-flowering oil were ß-bisabolene (28.54%), p-cymene (24.45%), and thymol methyl ether (15.90%). The EO obtained from the flowering aerial parts showed as principal metabolites ß-bisabolene (17.91%), thymol (16.26%), and limonene (15.59%). The EO of the flowering aerial parts, and its main pure constituents, ß-bisabolene, thymol, limonene, p-cymene, and thymol methyl ether were investigated for their antimicrobial activity against oral pathogens and for their antibiofilm and antioxidant properties.


Assuntos
Óleos Voláteis , Thymus (Planta) , Óleos Voláteis/química , Timol/farmacologia , Timol/análise , Limoneno/análise , Monoterpenos/análise , Thymus (Planta)/química , Etiópia , Sicília
18.
Molecules ; 28(9)2023 May 02.
Artigo em Inglês | MEDLINE | ID: mdl-37175263

RESUMO

Grindelia squarrosa is an arid lands herb that has been used in Native American traditional medicine, is a potential source of pharmacologically active compounds, and has been explored as a source of biofuel. The purpose of this work was to examine the essential oil composition of G. squarrosa from southern Idaho. Gas chromatographic methods revealed the essential oil of G. squarrosa var. serrulata to be rich in monoterpenoids, α-pinene (21.9%), limonene (17.1%), terpinolene (10.6%), and borneol (6.5%). The essential oil composition of G. squarrosa from Idaho is similar to that previously reported from specimens collected from Montana and confirms the volatile phytochemistry of plants growing in North America. The major essential oil components were screened for antimicrobial activity against respiratory and dermal pathogens. (-)-ß-Pinene showed strong antibacterial activity against Streptococcus pneumoniae (MIC 39.1 µg/mL) and (-)-borneol showed strong activity against Staphylococcus aureus (MIC 78.1 µg/mL).


Assuntos
Grindelia , Óleos Voláteis , Antibacterianos/análise , Antibacterianos/química , Antibacterianos/farmacologia , Grindelia/química , Idaho , Testes de Sensibilidade Microbiana , Óleos Voláteis/análise , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Monoterpenos/análise , Monoterpenos/química , Monoterpenos/farmacologia , Streptococcus pneumoniae/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacos , Antifúngicos/análise , Antifúngicos/química , Antifúngicos/farmacologia
19.
J Sci Food Agric ; 103(13): 6340-6351, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37195064

RESUMO

BACKGROUND: The ultraviolet-B (UV-B) radiation can alter grape metabolism during berry development, but little is known on the effect of postharvest UV-B exposure. In this study, we evaluated the effect of postharvest UV-B exposure on berry primary and secondary metabolites in four grapevine varieties (Aleatico, Moscato bianco, Sangiovese, and Vermentino) in order to evaluate the possibility to increase the grape quality and its nutraceutical properties. RESULTS: The treatment did not significantly affect the berry primary metabolism in terms of organic acids, carbohydrates, and amino acids profile, regardless of the variety. UV-B exposure reduced the total anthocyanin content, particularly the tri-substituted and di-substituted forms in Aleatico and Sangiovese, respectively. An overall negative effect of UV-B irradiation on the flavonols profile of Aleatico, Moscato bianco, and Vermentino berries was found, whereas it enhanced the quercetin, myricetin and kaempferol concentration in Sangiovese. The free fraction of berry volatile organic compounds increased in UV-B-treated Aleatico and Moscato bianco berries, especially C13 -norisoprenoids and volatile phenols, as well as key monoterpenes, such as the linalool derivatives. However, higher concentrations of glycosylated monoterpenes and C13 -norisoprenoids were measured in Sangiovese and Vermentino berries treated with UV-B. CONCLUSION: This study provides new insights on the effect of postharvest UV-B radiation on berry secondary metabolism, highlighting a different modulation between varieties and suggesting the potential use of this technique to increase some nutraceutical and quality characteristics of grape berry. © 2023 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.


Assuntos
Vitis , Vitis/química , Frutas/química , Norisoprenoides/metabolismo , Fenóis/química , Monoterpenos/análise
20.
Environ Pollut ; 327: 121569, 2023 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-37028792

RESUMO

To understand the source, formation, and seasonality of biogenic secondary organic aerosol (BSOA), a nine-stage cascade impactor was utilized to collect size-segregated particulate samples from April 2017 to January 2018 in Beijing, China. BSOA tracers derived from isoprene, monoterpene, and sesquiterpene were measured with gas chromatography-mass spectrometry. Isoprene and monoterpene SOA tracers exhibited significant seasonal variations, with a summer maximum and a winter minimum. Dominance of 2-methyltetrols (isoprene SOA tracers) with a good correlation with levoglucosan (a biomass burning tracer), which was combined with the detection of methyltartaric acids (possible indicators for aged isoprene) in summer, implies possible biomass burning and long-range transport. In contrast, sesquiterpene SOA tracer (ß-caryophyllinic acid) was dominant in winter and was probably associated with the local burning of biomass. Bimodal size distributions were observed for most isoprene SOA tracers, consistent with previous laboratory experiments and field studies showing that they can be formed not only in the aerosol phase but also in the gas phase. Monoterpene SOA tracers cis-pinonic acid and pinic acid showed a coarse-mode peak (5.8-9.0 µm) in four seasons due to their volatile nature. Sesquiterpene SOA tracer ß-caryophyllinic acid showed a unimodal pattern with a major fine-mode peak (1.1-2.1 µm), which is linked to local biomass burning. The tracer-yield method was used to quantify the contributions of isoprene, monoterpene, and sesquiterpene to secondary organic carbon (SOC) and SOA. The highest isoprene SOC and SOA concentrations occurred in summer (2.00 µgC m-3 and 4.93 µg m-3, respectively), contributing to 1.61% of OC and 5.22% of PM2.5, respectively. These results suggest that BSOA tracers are promising tracers for understanding the source, formation, and seasonality of BSOA.


Assuntos
Poluentes Atmosféricos , Sesquiterpenos , Poluentes Atmosféricos/análise , Pequim , Monoterpenos/análise , Sesquiterpenos/análise , Aerossóis/análise , Estações do Ano , Material Particulado/análise , Monitoramento Ambiental/métodos
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