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1.
Molecules ; 29(9)2024 Apr 25.
Artículo en Inglés | MEDLINE | ID: mdl-38731460

RESUMEN

Tanacetum parthenium L. (Asteraceae) is a perennial herbaceous plant with a long-standing historical use in traditional medicine. Recently Tanacetum parthenium L. essential oil has been associated with a promising potential for future applications in the pharmaceutical industry, in the cosmetics industry, and in agriculture. Investigations on the essential oil (EO) have indicated antimicrobial, antioxidant, and repellent activity. The present study aimed to evaluate the chemical composition of Bulgarian T. parthenium essential oil from two different regions, to compare the results to those reported previously in the literature, and to point out some of its future applications. The essential oils of the air-dried flowering aerial parts were obtained by hydrodistillation using a Clevenger-type apparatus. The chemical composition was evaluated using gas chromatography with mass spectrometry (GC-MS). It was established that the oxygenated monoterpenes were the predominant terpene class, followed by the monoterpene hydrocarbons. Significant qualitative and quantitative differences between both samples were revealed. Camphor (50.90%), camphene (16.12%), and bornyl acetate (6.05%) were the major constituents in the feverfew EO from the western Rhodope Mountains, while in the EO from the central Balkan mountains camphor (45.54%), trans-chrysanthenyl acetate (13.87%), and camphene (13.03%) were the most abundant components.


Asunto(s)
Cromatografía de Gases y Espectrometría de Masas , Aceites Volátiles , Tanacetum parthenium , Aceites Volátiles/química , Bulgaria , Tanacetum parthenium/química , Terpenos/química , Terpenos/análisis , Alcanfor/química , Alcanfor/análisis , Aceites de Plantas/química , Monoterpenos Bicíclicos
2.
Molecules ; 29(9)2024 Apr 25.
Artículo en Inglés | MEDLINE | ID: mdl-38731461

RESUMEN

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


Asunto(s)
Cromatografía de Gases y Espectrometría de Masas , Mentha spicata , Mentha , Aceites Volátiles , Aceites Volátiles/química , Mentha/química , Mentha spicata/química , Análisis Multivariante , Región Mediterránea , Monoterpenos Ciclohexánicos/química , Monoterpenos Ciclohexánicos/análisis , Monoterpenos/química , Monoterpenos/análisis , Limoneno/química , Terpenos/química , Terpenos/análisis , Mentol
3.
J Agric Food Chem ; 72(19): 11124-11139, 2024 May 15.
Artículo en Inglés | MEDLINE | ID: mdl-38698543

RESUMEN

Terpenes and pentene dimers are less studied volatile organic compounds (VOCs) but are associated with specific features of extra virgin olive oils (EVOOs). This study aimed to analyze mono- and sesquiterpenes and pentene dimers of Italian monovarietal EVOOs over 3 years (14 cultivars, 225 samples). A head space-solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS) method recently validated was used for terpene and pentene dimer quantitation. The quantitative data collected were used for both the characterization and clustering of the cultivars. Sesquiterpenes were the molecules that most characterized the different cultivars, ranging from 3.908 to 38.215 mg/kg; different groups of cultivars were characterized by different groups of sesquiterpenes. Pentene dimers (1.336 and 3.860 mg/kg) and monoterpenes (0.430 and 1.794 mg/kg) showed much lower contents and variability among cultivars. The application of Kruskal-Wallis test-PCA-LDA-HCA to the experimental data allowed defining 4 clusters of cultivars and building a predictive model to classify the samples (94.3% correct classification). The model was further tested on 33 EVOOs, correctly classifying 91% of them.


Asunto(s)
Cromatografía de Gases y Espectrometría de Masas , Olea , Aceite de Oliva , Control de Calidad , Microextracción en Fase Sólida , Terpenos , Compuestos Orgánicos Volátiles , Microextracción en Fase Sólida/métodos , Aceite de Oliva/química , Italia , Terpenos/química , Terpenos/análisis , Olea/química , Compuestos Orgánicos Volátiles/química , Quimiometría/métodos , Dimerización
4.
Food Res Int ; 186: 114347, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38729697

RESUMEN

Although Z. mioga flower buds are popular among consumers for its unique spicy flavor, high nutritional and medicinal value, there are few reports on the formation and changes of the flavor during its growth and maturation process. The understanding of the profile of volatile compounds would help to unravel the flavor formation for Z. mioga flower buds during growth. The volatile changes in Z. mioga flower buds were analyzed by GC-MS and a total of 182 volatile compounds identified, and the terpenoids accounted for the most abundant volatile substances. Almost all the identified volatiles presented an intuitive upward trend throughout the growth period and reached the maximum at the later stage of development (DS3 or DS4). Regarding the PCA and HCA results, there were significant differences found among the four stages, and the DS3 was the critical node. The top 50 differential volatiles screened by OPLS-DA and PLS-DA were all up-regulated, and the correlation analysis indicated that terpenoids might synergize with other chemical types of volatiles to jointly affect the flavor formation of Z. mioga flower buds during growth. The association network for flavor omics revealed that the most important sensory flavor for Z. mioga flower buds were woody and sweet, and the main contribution compounds for the unique flavor contained ß-guaiene, ß-farnesene, δ-cadinene and citronellyl isobutanoate. Taken together, the results of this study provided a reference for flavor quality evaluation of flower buds and determination of the best harvest period.


Asunto(s)
Flores , Cromatografía de Gases y Espectrometría de Masas , Compuestos Orgánicos Volátiles , Flores/crecimiento & desarrollo , Flores/metabolismo , Compuestos Orgánicos Volátiles/análisis , Compuestos Orgánicos Volátiles/metabolismo , Gusto , Terpenos/metabolismo , Terpenos/análisis
5.
Chem Commun (Camb) ; 60(43): 5598-5601, 2024 May 23.
Artículo en Inglés | MEDLINE | ID: mdl-38712724

RESUMEN

A simple aqueous host:guest sensing array can selectively discriminate between different types of citrus varietal from peel extract samples. It can also distinguish between identical citrus samples at varying stages of ripening. The discrimination effects stem from detection of changes in the terpenoid composition of the peel extracts by the host:guest array, despite the overwhelming excess of a single component, limonene, in each sample. The hosts are insensitive to limonene but bind other monoterpenes strongly, even though they are similar in structure to the major limonene component. This work demonstrates the capability of host:guest arrays in sensing target molecules in environments with the competing agents present at high abundances in the sample matrix.


Asunto(s)
Citrus , Terpenos , Citrus/química , Terpenos/química , Terpenos/análisis , Limoneno/química , Limoneno/análisis , Frutas/química
6.
Sci Total Environ ; 930: 172669, 2024 Jun 20.
Artículo en Inglés | MEDLINE | ID: mdl-38677435

RESUMEN

Isoprenoids (including isoprene (ISO) and monoterpenes (MTs)) are the majority of biogenic volatile organic compounds (BVOCs) which are important carbon-containing secondary metabolites biosynthesized by organisms, especially plant in terrestrial ecosystem. Results of the warming effects on isoprenoid emissions vary within species and warming facilities, and thus conclusions remain controversial. In this study, two typical subtropical tree species seedlings of Schima superba and Cunninghamia lanceolata were cultivated under three conditions, namely no warming (CK) and two warming facilities (with infrared radiators (IR) and heating wires (HW)) in open top chamber (OTC), and the isoprenoid emissions were measured with preconcentor-GC-MS system after warming for one, two and four months. The results showed that the isoprenoid emissions from S. superba and C. lanceolata exhibited uniformity in response to two warming facilities. IR and HW both stimulated isoprenoid emissions in two plants after one month of treatment, with increased ratios of 16.3 % and 72.5 % for S. superba, and 2.47 and 5.96 times for C. lanceolata. However, the emissions were suppressed after four months, with more pronounced effect for HW. The variation in isoprenoid emissions was primarily associated with the levels of Pn, Tr, monoterpene synthase (MTPS) activity. C. lanceolata predominantly released MTs (mainly α-pinene, α-terpene, γ-terpene, and limonene), with 39.7 % to 99.6 % of the total isoprenoid but ISO was only a very minor constituent. For S. superba, MTs constituted 24.7 % to 96.1 % of total isoprenoid. It is noteworthy that HW generated a greater disturbance to physiology activity in plants. Our study provided more comprehensive and more convincing support for integrating temperature-elevation experiments of different ecosystems and assessing response and adaptation of forest carbon cycle to global warming.


Asunto(s)
Cunninghamia , Terpenos , Terpenos/metabolismo , Terpenos/análisis , Contaminantes Atmosféricos/análisis , Compuestos Orgánicos Volátiles/análisis , Compuestos Orgánicos Volátiles/metabolismo , Calentamiento Global , Asteraceae/metabolismo , Asteraceae/fisiología , Calor , Hemiterpenos , Butadienos
7.
Molecules ; 29(8)2024 Apr 19.
Artículo en Inglés | MEDLINE | ID: mdl-38675683

RESUMEN

The vegetation of the Canary Islands is characterized by a large number of endemic species confined to different altitudinal levels. It can be assumed that these circumstances determine the characteristic features of the chemical composition of local beekeeping products, including propolis. We report, for the first time, the chemical composition of propolis from Tenerife (Canary Islands). The volatile emissions of three propolis samples collected from different apiaries are represented by 162 C1-C20 compounds, of which 144 were identified using the HS-SPME/GC-MS technique. The main group of volatiles, consisting of 72 compounds, is formed by terpenoids, which account for 42-68% of the total ion current (TIC) of the chromatograms. The next most numerous groups are formed by C6-C17 alkanes and alkenes (6-32% TIC) and aliphatic C3-C11 carbonyl compounds (7-20% TIC). The volatile emissions also contain C1-C6 aliphatic acids and C2-C8 alcohols, as well as their esters. Peaks of 138 organic C3-C34 compounds were recorded in the chromatograms of the ether extracts of the studied propolis. Terpene compounds form the most numerous group, but their number and content in different samples is within very wide limits (9-63% TIC), which is probably due to the origin of the samples from apiaries located at different altitudes. A peculiarity of the chemical composition of the extractive substances is the almost complete absence of phenylcarboxylic acids and flavonoids, characteristic of Apis mellifera propolis from different regions of Eurasia and North America. Aromatic compounds of propolis from Tenerife are represented by a group of nine isomeric furofuranoid lignans, as well as alkyl- and alkenyl-substituted derivatives of salicylic acid and resorcinol.


Asunto(s)
Cromatografía de Gases y Espectrometría de Masas , Própolis , Compuestos Orgánicos Volátiles , Própolis/química , Compuestos Orgánicos Volátiles/análisis , Compuestos Orgánicos Volátiles/química , España , Terpenos/química , Terpenos/análisis , Microextracción en Fase Sólida
8.
Molecules ; 29(6)2024 Mar 18.
Artículo en Inglés | MEDLINE | ID: mdl-38542978

RESUMEN

Essential oils are secondary metabolites in plants with a variety of biological activities. The flavor and quality of Zanthoxylum armatum DC. are mainly determined by the essential oil components in the Chinese prickly ash peels. In this study, the correlation between climate change in different regions and the content of essential oils of Z. armatum was investigated using gas chromatography-mass spectrometry (GC/MS) and multivariate statistical analysis. The Z1-24 refers to 24 batches of samples from different habitats. A total of 145 essential oils were detected in 24 batches of samples, with the highest number of terpene species and the highest content of alcohol. The relative odor activity (ROAV) values identified nine main flavor compounds affecting the odor of Z. armatum. Linalool, decanal, and d-limonene were the most critical main flavor compounds, giving Z. armatum a spicy, floral, oily, and fruity odor. The results of hierarchical cluster analysis (HCA) and principal component analysis (PCA) classified Z5 into a separate group, Z2 and Z7 were clustered into one group, and the rest of the samples were classified into another group. Correlation analysis and path analysis showed that temperature and precipitation were the main climatic factors affecting essential oils. Comparisons can be made with other plants in the genus Zanthoxylum to analyze differences in essential oil type and content. This study contributes to the identification of Z. armatum quality, promotes the accumulation of theories on the effects of climatic factors on essential oils, and enriches the site selection and breeding of Z. armatum under similar climatic conditions.


Asunto(s)
Aceites Volátiles , Zanthoxylum , Aceites Volátiles/química , Zanthoxylum/química , Fitomejoramiento , Terpenos/análisis , China
9.
Anal Biochem ; 689: 115503, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38453049

RESUMEN

Terpenes play a vital role in plant defense; tomato plants produce a diverse range of terpenes within specialized glandular trichomes, influencing interactions with herbivores, predators, and pollinators. This study employed two distinct methods, namely leaf dip and maceration, to extract trichomes from tomato leaves. Terpene quantification was carried out using Gas Chromatography-Mass Spectrometry (GC-MS). The leaf dip method proved effective in selectively targeting trichome content, revealing unique extraction patterns compared to maceration. The GC-MS method demonstrated high linearity, accuracy, sensitivity, and low limits of detection and quantification. Application of the method to different tomato species (Solanum pennellii, Solanum pimpinellifolium, Solanum galapagense, Solanum habrochaites, and Solanum lycopersicum) identified significant variation in terpene content among these species, highlighting the potential of specific accessions for breeding programs. Notably, the terpene α-zingiberene, known for its repellency against whiteflies, was found in high quantities (211.90-9155.13 µg g-1) in Solanum habrochaites accession PI209978. These findings provide valuable insights into terpenoid diversity for plant defense mechanisms, guiding future research on developing pest-resistant tomato cultivars. Additionally, the study underscores the broader applications of terpenes in agriculture.


Asunto(s)
Solanum lycopersicum , Solanum , Terpenos/análisis , Cromatografía de Gases y Espectrometría de Masas , Extractos Vegetales
10.
J Chromatogr A ; 1720: 464810, 2024 Apr 12.
Artículo en Inglés | MEDLINE | ID: mdl-38471299

RESUMEN

Nowadays, the higher peak capacity achievable by comprehensive two-dimensional liquid chromatography (LC×LC) for the analysis of vegetal samples is well-recognized. In addition, numerous compounds may be present in very different amounts. Cannabinoids and terpenes represent the main components of Cannabis sativa inflorescence samples, whose quantities are relevant for many application purposes. The analyses of both families are performed by different methods, at least two different separation methodologies, mainly according to their chemical characteristics and concentration levels. In this work, concentration differences and sample complexity issues were addressed using an LC×LC method that incorporates an optimized modulation strategy, namely smart active modulation, for the simultaneous analysis of cannabinoids and terpenes. The system was built by interposing an active flow splitter pump between both dimensions. This set up aimed to exploit the known advantages of LC×LC. In addition, here we proposed to use the splitter pump for online control over the splitting ratio to facilitate the selective dilution of different eluted fractions containing compounds with highly different concentrations. This work represents the first application and demonstration of smart active modulation (SAM) in LC×LC to simultaneously determine analytes with significant differences in concentration levels present in complex samples. The proposed method was tested with eight different strains, from which fingerprints were taken, and numerous cannabinoids and terpenes were identified in these samples. With this strategy, between 49 and 54 peaks were obtained in the LC×LC chromatograms corresponding to different strains. THCA-A was the main component in six strains, while CBDA was the main component in the other two strains. The main terpenes found were myrcene (in five strains), limonene (in two strains), and humulene (in one strain). Additionally, numerous other cannabinoids and terpenes were identified in these samples, providing valuable compositional information for growers, as well as medical and recreational users. The SAM strategy here proposed is simple and it can be extended to other complex matrices.


Asunto(s)
Cannabinoides , Cannabis , Humanos , Cannabinoides/análisis , Cannabis/química , Terpenos/análisis , Inflorescencia/química , Cromatografía de Gases y Espectrometría de Masas , Cromatografía Líquida de Alta Presión
11.
Biomed Chromatogr ; 38(5): e5838, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38342982

RESUMEN

Strobilanthes sarcorrhiza (CTS) is a medicinal plant with various pharmacological effects such as tonifying kidney and anti-inflammatory. However, the chemical composition and difference of its four parts (leaves, stems, rhizomes, and root tubers) have been rarely reported. In this study, ultrafast flow liquid chromatography coupled with quadrupole-time-of-flight MS was applied to analyze the chemical profile of CTS and identify 55 compounds, including terpenoids, phenylethanol glycosides, fatty acid derivatives, chain glycosides, flavonoid glycosides, and others. Among these compounds, 34 compounds were first identified in CTS. They were mainly terpenoids, phenylethanol glycosides, fatty acid derivatives, and so forth. Multivariate statistical analysis, such as principal component analysis and orthogonal partial least squares-discriminant analysis were also used to evaluate the difference in chemical compounds from the four parts of CTS. The results showed that phenylethanol glycosides were the main compounds of the underground parts, while terpenoids were the main compounds of the aboveground parts. This study revealed the chemical diversity and similarity of CTS and suggested that the rhizomes could be used as an alternative medicinal part to improve the resource utilization of CTS.


Asunto(s)
Espectrometría de Masas , Análisis Multivariante , Espectrometría de Masas/métodos , Cromatografía Liquida/métodos , Extractos Vegetales/química , Terpenos/análisis , Terpenos/química , Glicósidos/análisis , Glicósidos/química , Cromatografía Líquida de Alta Presión/métodos
12.
Rapid Commun Mass Spectrom ; 38(6): e9704, 2024 Mar 30.
Artículo en Inglés | MEDLINE | ID: mdl-38356092

RESUMEN

RATIONALE: The efficiency of selected ion monitoring (SIM) and selected reaction monitoring (SRM) analyses for the quantification of three mono-, di- and tri-unsaturated highly branched isoprenoid (HBI) alkenes (IP25 , IPSO25 and HBI III, respectively), often used as proxies for the occurrence of Arctic and Antarctic sea ice or the adjacent open waters, was compared. METHODS: Gas chromatography (GC)-mass spectrometry (MS)/SIM and GC/MS/MS/SRM analyses were carried out on dilute solutions made from purified standards of these three HBIs, and then on hydrocarbon fractions of several sediment and sea ice sample extracts. More efficient and specific SRM transitions were selected after collision-induced dissociation of each precursor ion at different collision energies. RESULTS: SRM analysis avoided any overestimation of IP25 resulting from the contribution of the coeluting 13 C mass isotopomer of IPSO25 (M+ ˙ + 2) to the SIM target ion. In contrast, SRM analysis is less reliable for IPSO25 quantification in cases where several regio-isomers are present, likely due to intense double bond migrations following electron impact. In the case of HBI III, SRM analysis constitutes a potentially suitable alternative to SIM analysis, especially in terms of improving limit of detection. CONCLUSIONS: Despite the intense migrations of HBI double bonds under electron ionization, the selected SRM transitions should be more suitable than SIM target ions for IP25 and HBI III quantification in complex hydrocarbon fractions of natural samples. However, the advantage is less evident for IPSO25 due to the presence of numerous regio-isomers.


Asunto(s)
Espectrometría de Masas en Tándem , Terpenos , Cromatografía de Gases y Espectrometría de Masas/métodos , Espectrometría de Masas en Tándem/métodos , Terpenos/análisis , Alquenos/análisis , Cubierta de Hielo , Biomarcadores/análisis
13.
BMC Plant Biol ; 24(1): 84, 2024 Feb 02.
Artículo en Inglés | MEDLINE | ID: mdl-38308239

RESUMEN

BACKGROUND: Cinnamomum cassia Presl, classified in the Lauraceae family, is widely used as a spice, but also in medicine, cosmetics, and food. Aroma is an important factor affecting the medicinal and flavoring properties of C. cassia, and is mainly determined by volatile organic compounds (VOCs); however, little is known about the composition of aromatic VOCs in C. cassia and their potential molecular regulatory mechanisms. Here, integrated transcriptomic and volatile metabolomic analyses were employed to provide insights into the formation regularity of aromatic VOCs in C. cassia bark at five different harvesting times. RESULTS: The bark thickness and volatile oil content were significantly increased along with the development of the bark. A total of 724 differentially accumulated volatiles (DAVs) were identified in the bark samples, most of which were terpenoids. Venn analysis of the top 100 VOCs in each period showed that twenty-eight aromatic VOCs were significantly accumulated in different harvesting times. The most abundant VOC, cinnamaldehyde, peaked at 120 months after planting (MAP) and dominated the aroma qualities. Five terpenoids, α-copaene, ß-bourbonene, α-cubebene, α-funebrene, and δ-cadinene, that peaked at 240 MAP could also be important in creating C. cassia's characteristic aroma. A list of 43,412 differentially expressed genes (DEGs) involved in the biosynthetic pathways of aromatic VOCs were identified, including phenylpropanoids, mevalonic acid (MVA) and methylerythritol phosphate (MEP). A gene-metabolite regulatory network for terpenoid and phenylpropanoid metabolism was constructed to show the key candidate structural genes and transcription factors involved in the biosynthesis of terpenoids and phenylpropanoids. CONCLUSIONS: The results of our research revealed the composition and changes of aromatic VOCs in C. cassia bark at different harvesting stages, differentiated the characteristic aroma components of cinnamon, and illuminated the molecular mechanism of aroma formation. These foundational results will provide technical guidance for the quality breeding of C. cassia.


Asunto(s)
Cinnamomum aromaticum , Cinnamomum aromaticum/química , Corteza de la Planta/genética , Fitomejoramiento , Perfilación de la Expresión Génica , Terpenos/análisis
14.
J Food Sci ; 89(2): 1058-1072, 2024 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-38221804

RESUMEN

Volatile organic compounds in honey are known for their considerable impact on the organoleptic properties of honey, such as aroma, flavor, taste, and texture. The type and composition of volatile organic compounds are influenced by entomological, geographical, and botanical origins; thus, these compounds have the potential to be chemical markers. Sixty-two volatile compounds were identified using gas chromatography-mass spectrometry from 30 Heterotrigona itama (H. itama) honey samples from 3 different geographical origins. Hydrocarbons and benzene derivatives were the dominant classes of volatile organic compounds in the samples. Both clustering and discriminant analyses demonstrated a clear separation between samples from distant origins (Kedah and Perak), and the volcano plot supported it. The reliability and predictability of the partial least squares-discriminant analysis model from the discriminant analysis were validated using cross-validation (R2 : 0.93; Q2 : 0.83; accuracy: 0.97) and the permutation test (p < 0.001), and the output depicted that the model is legitimate. In combination with the variable importance of projection (VIP > 1.0) and the Kruskal-Wallis test (p < 0.01), 19 volatile organic compounds (encompassed aldehydes, benzene derivatives, esters, hydrocarbons, and terpenoids) were sorted and named potent chemical markers in classifying honey samples from three geographical origins. In brief, this study illustrated that volatile organic compounds of stingless honey originated from the same bee species, but different geographical origins could be applied as chemical markers.


Asunto(s)
Miel , Compuestos Orgánicos Volátiles , Abejas , Animales , Miel/análisis , Cromatografía de Gases y Espectrometría de Masas/métodos , Compuestos Orgánicos Volátiles/análisis , Reproducibilidad de los Resultados , Malasia , Terpenos/análisis , Derivados del Benceno
15.
J Chromatogr A ; 1715: 464600, 2024 Jan 25.
Artículo en Inglés | MEDLINE | ID: mdl-38176352

RESUMEN

An automated implementation for a subfractionation of mineral oil aromatic hydrocarbons (MOAH) into a mono-/di-aromatic fraction (MDAF) and a tri-/poly-aromatic fraction (TPAF) is presented, which is highly demanded by the European Food Safety Authority (EFSA) respecting the genotoxic and carcinogenic potential of MOAH. For this, donor-acceptor-complex chromatography (DACC) was used as a selective stationary phase to extend the conventional instrumental setup for the analysis of mineral oil hydrocarbons via on-line coupled liquid chromatography-gas chromatography-flame ionization detection (LC-GC-FID). A set of six new internal standards was introduced for the verification of the MOAH fractionation and a quantification of MDAF and TPAF, respectively. The automated DACC approach was applied to representative petrochemical references as well as to food samples, such as rice and infant formula, generally showing well conformity with results obtained by state-of-the-art analysis using two-dimensional GC (GCxGC). Relative deviations of DACC/LC-GC-FID compared to GCxGC-FID methods regarding the ≥ 3 ring MOAH content ranged between -50 and +6 % (median: -2 %, all samples, only values above limit of quantification). However, crucial deviations mainly result from "border-crossing" substances, e.g., dibenzothiophenes or partially hydrogenated MOAH. These substances can cause overestimations of ≥ 3 ring MOAH fraction during GCxGC analysis due to co-elution, which is mostly avoided using the DACC approach. Furthermore, the DACC approach can help to minimize underestimations of toxicologically relevant ≥ 3 ring MOAH caused by an unavoidable loss of MOAH during epoxidation, since natural olefins, such as terpenes, predominantly elute in MDAF, which was exemplarily shown for an olive oil and a terpene reference. The presented approach can be implemented easily in existing LC-GC-FID setup for an automated and advanced screening of MOAH to lower the need for elaborate GCxGC analysis also in routine environments.


Asunto(s)
Hidrocarburos Aromáticos , Aceite Mineral , Humanos , Aceite Mineral/análisis , Contaminación de Alimentos/análisis , Hidrocarburos Aromáticos/análisis , Cromatografía de Gases/métodos , Cromatografía Liquida/métodos , Hidrocarburos/análisis , Terpenos/análisis
16.
J Agric Food Chem ; 72(5): 2813-2825, 2024 Feb 07.
Artículo en Inglés | MEDLINE | ID: mdl-38263713

RESUMEN

A head space-solid phase microextraction-gas chromatography-mass spectrometery (HS-SPME-GC-MS) method for the simultaneous analysis of pentene dimers from lipoxygenase (LOX) pathway, monoterpenes, and sesquiterpenes in extra virgin olive oil (EVOO) was proposed. A Doehlert design was performed; the conditions of the HS-SPME preconcentration step (extraction temperature, extraction time, sample amount, and desorption time) were optimized by response surface methodology, allowing defining the method operable design region. A quantitative method was set up using the multiple internal standard normalization approach: four internal standards were used, and the most suitable one was selected for area normalization of each external standard. The quantitative method was successfully validated and applied to a series of monocultivar EVOOs. This is the first paper in which a quantitative method using commercial standards has been proposed for the analysis of an important class of molecules of EVOO such as pentene dimers. The optimized method is suitable for routine analysis aimed at characterizing high quality EVOOs.


Asunto(s)
Terpenos , Compuestos Orgánicos Volátiles , Aceite de Oliva/análisis , Terpenos/análisis , Microextracción en Fase Sólida/métodos , Cromatografía de Gases y Espectrometría de Masas/métodos , Alquenos/análisis , Compuestos Orgánicos Volátiles/análisis , Hidrocarburos
17.
Environ Res ; 243: 117843, 2024 Feb 15.
Artículo en Inglés | MEDLINE | ID: mdl-38061588

RESUMEN

BACKGROUND: The utilization of short-term natural exposure as a health intervention has great potential in the field of public health. However, previous studies have mostly focused on outdoor urban green spaces, with limited research on indoor biophilic environments, and the physiological regulatory mechanisms involved remain unclear. OBJECTIVES: To explore the affective and physiological impact of short-term exposure to indoor biophilic environments and their potential regulatory mechanisms. METHODS: A between-group design experiment was conducted, and the psychophysiological responses of participants to the indoor plants (Vicks Plant) were measured by a method combined the subjective survey, electrophysiological measurements, and salivary biochemical analysis. Volatile organic compounds (VOCs) from plants were also detected to analyze the main substances that caused olfactory stimuli. RESULTS: Compared with the non-biophilic environment, short-term exposure to the indoor biophilic environment was associated with psychological and physiological relaxation, including reduced negative emotions, improved positive emotions, lower heart rate, skin conductance level, salivary cortisol and pro-inflammatory cytokines, and increased alpha brainwave power. Salivary metabolomics analysis revealed that the differential metabolites observed between the groups exhibited enrichment in two metabolic pathways related to neural function and immune response: phenylalanine, tyrosine and tryptophan biosynthesis, and ubiquinone and other terpenoid-quinone biosynthesis. These changes may be associated with the combined visual and olfactory stimuli of the biophilic environment, in which D-limonene was the dominant substance in plant-derived VOCs. CONCLUSION: This research demonstrated the benefits of short-term exposure to indoor biophilic environments on psychophysiological health through evidence from both the nervous and endocrine systems.


Asunto(s)
Contaminación del Aire Interior , Compuestos Orgánicos Volátiles , Humanos , Encuestas y Cuestionarios , Compuestos Orgánicos Volátiles/análisis , Terpenos/análisis , Contaminación del Aire Interior/análisis
18.
Microsc Res Tech ; 87(4): 790-799, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38071733

RESUMEN

Juniper species contain abundant compounds that are used in the medicine, cosmetic, and wood industry. Furthermore, these components protect the genus against herbivores, pathogens and detrimental abiotic conditions. Stains and specific reagents can be used individually or simultaneously to mark cell shape, arrangement and the material they are made from. Microchemical analyses using specific reagents and stains under light microscopy are helpful for the characterization of chemical compounds present in plant tissues. The autofluorescence of endogenous fluorophores is used to enable their localization in plant cells and tissues. This paper aims to investigate the cytochemical and histochemical traits of the shoots (leaves and stems) and female cones (berries) of Juniperus seravschanica. Light and florescent microscopy techniques were used to analyze the cytology and localization of different compounds for the first time. Microscopy-based histochemical analyses revealed various products in terms of composition and distribution among the shoots and female cones. These specific compounds contained lignin, tannins, polysaccharides, starch, phenolic compounds, chlorophyll, terpenoids, neutral lipids, and proteins. However, the anatomical position of each metabolite and its concentration was different among leaf, stem, and female cone. Phenolic cells of young cones were differentiated into sclereid cells during development. The density of phenolic cells, sclereid cells, and resin glans was higher in female cones than leaves and stems. The high levels of various components can be related to high resistance of the species against biotic and abiotic stresses, confirm its industrial, pharmaceutical and agricultural applications and is useful for identification of diagnostic taxonomic traits. RESEARCH HIGHLIGHTS: Microscopical and histochemical analyses showed various compounds in J. seravschanica The phenolic cells differentiated to sclereid cells during development High levels of idioblasts and various compounds show its high resistance and medicinal role.


Asunto(s)
Cupressaceae , Juniperus , Juniperus/química , Terpenos/análisis , Extractos Vegetales/química , Polisacáridos
19.
Evolution ; 78(1): 98-110, 2024 Jan 04.
Artículo en Inglés | MEDLINE | ID: mdl-37897499

RESUMEN

Floral volatiles play key roles as signaling agents that mediate interactions between plants and animals. Despite their importance, few studies have investigated broad patterns of volatile variation across groups of plants that share pollinators, particularly in a phylogenetic context. The "perfume flowers," Neotropical plant species exhibiting exclusive pollination by male euglossine bees in search of chemical rewards, present an intriguing system to investigate these patterns due to the unique function of their chemical phenotypes as both signaling agents and rewards. We leverage recently developed phylogenies and knowledge of biosynthesis, along with decades of chemical ecology research, to characterize axes of variation in the chemistry of perfume flowers, as well as understand their evolution at finer taxonomic scales. We detect pervasive chemical convergence, with many species across families exhibiting similar volatile phenotypes. Scent profiles of most species are dominated by compounds of either the phenylpropanoid or terpenoid biosynthesis pathways, while terpenoid compounds drive more subtle axes of variation. We find recapitulation of these patterns within two independent radiations of perfume flower orchids, in which we further detect evidence for the rapid evolution of divergent floral chemistries, consistent with the putative importance of scent in the process of adaptation and speciation.


Asunto(s)
Odorantes , Perfumes , Humanos , Abejas , Animales , Filogenia , Perfumes/análisis , Flores/química , Polinización , Feromonas , Terpenos/análisis
20.
Food Res Int ; 175: 113719, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-38128985

RESUMEN

Owing to the short picking period of the fresh Zanthoxylum bungeanum, the postharvest drying has become an essential operation before the storage and transportation of Z. bungeanum. To explore the effects of drying methods on volatile characteristics, the volatilomic profiling of five different dried Z. bungeanum was investigated by E-nose, HS-SPME-GC/MS, GC-IMS in combination with chemometrics. The results indicated that W1W, W2W and W5S sensors within E-nose analysis showed the strongest responses in both fresh and dried Z. bungeanum. According to the identification of volatile organic compounds (VOCs), terpenes, esters and alcohols played the major roles in the volatile formation of the fresh and dried Z. bungeanum. The samples derived from hot air drying showed the relatively similar features with the fresh sample based on the relative abundances of these major VOCs. According to the results of multiple factor analysis (MFA), GC-IMS showed the strongest ability in distinguishing the fresh and different dried samples. Compared with the high levels of terpenes in fresh group, the significant increasement of terpene alcohols and terpene esters from the degradation and transformation of bound terpenoids was the main characteristics of all dried Z. bungeanum. Using the GC-IMS datasets, a weighted correlation network analysis (WCNA) model was constructed to clarify the VOC characteristics in all detetected samples. Thereinto, 6 significantly correlated modules were identified in fresh and five different dried samples. Additionally, a total of 23 hub VOCs can be recognized as the potential biomarkers for better distinguishing the fresh and five different dried Z. bungeanum.


Asunto(s)
Compuestos Orgánicos Volátiles , Zanthoxylum , Quimiometría , Terpenos/análisis , Alcoholes/análisis , Cromatografía de Gases y Espectrometría de Masas/métodos , Compuestos Orgánicos Volátiles/análisis , Ésteres/análisis
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