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Progress in Volatile Organic Compounds Research

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 October 2019) | Viewed by 83408

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Department of Organic Chemistry, Faculty of Chemistry and Technology, University of Split, HR-21000 Split, Croatia
Interests: volatile organic compounds (terpenes, norisoprenoids, aliphatic and aromatic compounds, others); glycosidically bound volatiles; chemical biomarkers; chemical biodiversity; gas chromatography and mass spectrometry; organic chemistry
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Special Issue Information

Dear Colleagues,

Volatile organic compounds (VOCs) have been intensively investigated in last few decades. Their origins could be different: Plant secondary metabolites, food/beverages aroma, fungal/bacterial volatiles, and others. VOCs typically occur as a complex mixture of compounds (e.g., monoterpenes, sesquiterpenes, norisoprenoids, aliphatic/aromatic compounds, sulfur containing compounds, others). They are formed through different biochemical pathways and could be modified or created during drying or maturation, thermal treatment, and others. Different conventional or modern methods of VOCs isolation followed by the analysis with chromatographic and spectroscopic techniques usually provide different chemical profiles and have been under constant modification and upgrading. The ecological interactions are mediated by VOCs (inter- and intra-organismic communication) and they can act as pheromones, attractants or alleochemicals. Among them, chemical biomarkers of botanical origin or chemotaxonomic markers can be found. Many VOCs possess different biological activities, such as antioxidant, antimicrobial, antiviral, anticancer, and others.

There is still great need to research VOCs from different sources, to report their distribution, chemical profiles, and to discover new compounds. This Special Issue aims to attract up-to-date contributions on all aspects of VOCs chemistry (from challenges in their isolation, analysis to synthesis) and on unlocking their biological activities or other useful properties.

Prof. Dr. Igor Jerković
Guest Editor

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Keywords

  • volatile organic compounds
  • essential oils
  • headspace compounds
  • modern methods of volatiles isolation, analysis or synthesis
  • chemical or chemotaxonomic biomarkers
  • pheromones, attractants, alleochemicals
  • biological activity
  • GC-MS

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Published Papers (15 papers)

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Research

16 pages, 3030 KiB  
Article
Discrimination of Cultivated Regions of Soybeans (Glycine max) Based on Multivariate Data Analysis of Volatile Metabolite Profiles
by So-Yeon Kim, So Young Kim, Sang Mi Lee, Do Yup Lee, Byeung Kon Shin, Dong Jin Kang, Hyung-Kyoon Choi and Young-Suk Kim
Molecules 2020, 25(3), 763; https://doi.org/10.3390/molecules25030763 - 10 Feb 2020
Cited by 10 | Viewed by 4145
Abstract
Soybean (Glycine max) is a major crop cultivated in various regions and consumed globally. The formation of volatile compounds in soybeans is influenced by the cultivar as well as environmental factors, such as the climate and soil in the cultivation areas. [...] Read more.
Soybean (Glycine max) is a major crop cultivated in various regions and consumed globally. The formation of volatile compounds in soybeans is influenced by the cultivar as well as environmental factors, such as the climate and soil in the cultivation areas. This study used gas chromatography-mass spectrometry (GC-MS) combined by headspace solid-phase microextraction (HS-SPME) to analyze the volatile compounds of soybeans cultivated in Korea, China, and North America. The multivariate data analysis of partial least square-discriminant analysis (PLS-DA), and hierarchical clustering analysis (HCA) were then applied to GC-MS data sets. The soybeans could be clearly discriminated according to their geographical origins on the PLS-DA score plot. In particular, 25 volatile compounds, including terpenes (limonene, myrcene), esters (ethyl hexanoate, butyl butanoate, butyl prop-2-enoate, butyl acetate, butyl propanoate), aldehydes (nonanal, heptanal, (E)-hex-2-enal, (E)-hept-2-enal, acetaldehyde) were main contributors to the discrimination of soybeans cultivated in China from those cultivated in other regions in the PLS-DA score plot. On the other hand, 15 volatile compounds, such as 2-ethylhexan-1-ol, 2,5-dimethylhexan-2-ol, octanal, and heptanal, were related to Korean soybeans located on the negative PLS 2 axis, whereas 12 volatile compounds, such as oct-1-en-3-ol, heptan-4-ol, butyl butanoate, and butyl acetate, were responsible for North American soybeans. However, the multivariate statistical analysis (PLS-DA) was not able to clearly distinguish soybeans cultivated in Korea, except for those from the Gyeonggi and Kyeongsangbuk provinces. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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15 pages, 2102 KiB  
Article
The Antibacterial Activity of Lavender Essential Oil Alone and In Combination with Octenidine Dihydrochloride against MRSA Strains
by Paweł Kwiatkowski, Łukasz Łopusiewicz, Mateusz Kostek, Emilia Drozłowska, Agata Pruss, Bartosz Wojciuk, Monika Sienkiewicz, Hanna Zielińska-Bliźniewska and Barbara Dołęgowska
Molecules 2020, 25(1), 95; https://doi.org/10.3390/molecules25010095 - 26 Dec 2019
Cited by 43 | Viewed by 8259
Abstract
In the post-antibiotic era the issue of bacterial resistance refers not only to antibiotics themselves but also to common antiseptics like octenidine dihydrochloride (OCT). This appears as an emerging challenge in terms of preventing staphylococcal infections, which are both potentially severe and easy [...] Read more.
In the post-antibiotic era the issue of bacterial resistance refers not only to antibiotics themselves but also to common antiseptics like octenidine dihydrochloride (OCT). This appears as an emerging challenge in terms of preventing staphylococcal infections, which are both potentially severe and easy to transfer horizontally. Essential oils have shown synergisms both with antibiotics and antiseptics. Therefore the aim of this study was to investigate the impact of lavender essential oil (LEO) on OCT efficiency towards methicillin-resistant S. aureus strains (MRSA). The LEO analyzed in this study increased the OCT’s susceptibility against MRSA strains. Subsequent FTIR analysis revealed cellular wall modifications in MRSA strain cultured in media supplemented with OCT or LEO/OCT. In conclusion, LEO appears to be a promising candidate for an efficient enhancer of conventional antiseptics. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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12 pages, 1095 KiB  
Article
Volatilomic Analysis of Four Edible Flowers from Agastache Genus
by Basma Najar, Ilaria Marchioni, Barbara Ruffoni, Andrea Copetta, Laura Pistelli and Luisa Pistelli
Molecules 2019, 24(24), 4480; https://doi.org/10.3390/molecules24244480 - 6 Dec 2019
Cited by 31 | Viewed by 3831
Abstract
Volatilomes emitted from edible flowers of two species of Agastache (A. aurantiaca (A.Gray) Lint & Epling, and A. mexicana (Kunth) Lint & Epling) and from two hybrids (Agastache ‘Arcado Pink’ and Agastache ‘Blue Boa’) were investigated using a solid-phase microextraction technique [...] Read more.
Volatilomes emitted from edible flowers of two species of Agastache (A. aurantiaca (A.Gray) Lint & Epling, and A. mexicana (Kunth) Lint & Epling) and from two hybrids (Agastache ‘Arcado Pink’ and Agastache ‘Blue Boa’) were investigated using a solid-phase microextraction technique as well as the extraction of its essential oils. Oxygenated monoterpenes were almost always the predominant class (>85%) of volatile organic compounds (VOCs) in each sample of A. aurantiaca, A. ‘Blue Boa’ and A. mexicana, with the exception of A. ‘Arcado Pink’ (38.6%). Pulegone was the main compound in A. aurantiaca (76.7%) and A. ‘Blue Boa’ (82.4%), while geranyl acetate (37.5%) followed by geraniol (16%) and geranial (17%) were the principal ones in A. mexicana. The essential oil composition showed the same behavior as the VOCs both for the main class as well as the major constituent (pulegone) with the same exception for A. mexicana. Total soluble sugars, secondary metabolites (polyphenols, flavonoids and anthocyanins) and antioxidant activity were also investigated to emphasize the nutraceutical properties of these edible flowers. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
12 pages, 780 KiB  
Communication
Composition of Essential Oils from Roots and Aerial Parts of Carpesium divaricatum, a Traditional Herbal Medicine and Wild Edible Plant from South-East Asia, Grown in Poland
by Anna Wajs-Bonikowska, Janusz Malarz and Anna Stojakowska
Molecules 2019, 24(23), 4418; https://doi.org/10.3390/molecules24234418 - 3 Dec 2019
Cited by 9 | Viewed by 4249
Abstract
Carpesium divaricatum Sieb. and Zucc. has long been used both as traditional medicine and seasonal food. The most extensively studied specialized metabolites synthesized by the plant are sesquiterpene lactones of germacrane-type. Low-molecular and volatile terpenoids produced by C. divaricatum, however, have never [...] Read more.
Carpesium divaricatum Sieb. and Zucc. has long been used both as traditional medicine and seasonal food. The most extensively studied specialized metabolites synthesized by the plant are sesquiterpene lactones of germacrane-type. Low-molecular and volatile terpenoids produced by C. divaricatum, however, have never been explored. In this work, compositions of essential oils distilled from roots and shoots of C. divaricatum plants, cultivated either in the open field or in the glasshouse have been studied by GC-MS-FID supported by NMR spectroscopy. The analyses led to the identification of 145 compounds in all, 112 of which were localized in aerial parts and 80 in roots of the plants grown in the open field. Moreover, remarkable differences in composition of oils produced by aerial and underground parts of C. divaricatum have been observed. The major volatiles found in the shoots were: α-pinene (40%), nerol (4%) and neryl-isobutyrate (3%), whereas predominant components of the root oil were 10-isobutyryloxy-8,9-epoxythymyl-isobutyrate (29%), thymyl-isobutyrate (6%) and 9-isobutyryloxythymyl-isobutyrate (6%). In the analyzed oils, seventeen thymol derivatives were identified. Among them eight compounds were specific for roots. Roots of the plants cultivated in the glasshouse were, in general, a poor source of essential oil in comparison with those of the plants grown in the open field. Chemophenetic relationships with other taxa of the Inuleae-Inulineae were also briefly discussed. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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17 pages, 11211 KiB  
Article
Antimicrobial Activity of Chamomile Essential Oil: Effect of Different Formulations
by Sourav Das, Barbara Horváth, Silvija Šafranko, Stela Jokić, Aleksandar Széchenyi and Tamás Kőszegi
Molecules 2019, 24(23), 4321; https://doi.org/10.3390/molecules24234321 - 26 Nov 2019
Cited by 42 | Viewed by 8402
Abstract
Essential oils (EOs) are highly lipophilic, which makes the measurement of their biological action difficult in an aqueous environment. We formulated a Pickering nanoemulsion of chamomile EO (CPe). Surface-modified Stöber silica nanoparticles (20 nm) were prepared and used as a stabilizing [...] Read more.
Essential oils (EOs) are highly lipophilic, which makes the measurement of their biological action difficult in an aqueous environment. We formulated a Pickering nanoemulsion of chamomile EO (CPe). Surface-modified Stöber silica nanoparticles (20 nm) were prepared and used as a stabilizing agent of CPe. The antimicrobial activity of CPe was compared with that of emulsion stabilized with Tween 80 (CT80) and ethanolic solution (CEt). The antimicrobial effects were assessed by their minimum inhibitory concentration (MIC90) and minimum effective (MEC10) concentrations. Besides growth inhibition (CFU/mL), the metabolic activity and viability of Gram-positive and Gram-negative bacteria as well as Candida species, in addition to the generation of oxygen free radical species (ROS), were studied. We followed the killing activity of CPe and analyzed the efficiency of the EO delivery for examined formulations by using unilamellar liposomes as a cellular model. CPe showed significantly higher antibacterial and antifungal activities than CT80 and CEt. Chamomile EOs generated superoxide anion and peroxide related oxidative stress which might be the major mode of action of Ch essential oil. We could also demonstrate that CPe was the most effective in donation of the active EO components when compared with CT80 and CEt. Our data suggest that CPe formulation is useful in the fight against microbial infections. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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14 pages, 546 KiB  
Article
Fingerprinting, Antimicrobial, Antioxidant, Anticancer, Cyclooxygenase and Metabolic Enzymes Inhibitory Characteristic Evaluations of Stachys viticina Boiss. Essential Oil
by Nidal Jaradat and Nawaf Al-Maharik
Molecules 2019, 24(21), 3880; https://doi.org/10.3390/molecules24213880 - 28 Oct 2019
Cited by 19 | Viewed by 3319
Abstract
The present study aimed to identify the chemical constituents and to assess the in-vitro, antimicrobial, anticancer, antioxidant, metabolic enzymes and cyclooxygenase (COX) inhibitory properties of essential oil (EO) of Stachys viticina Boiss. leaves. The S. viticina EO was isolated and identified using microwave-ultrasonic [...] Read more.
The present study aimed to identify the chemical constituents and to assess the in-vitro, antimicrobial, anticancer, antioxidant, metabolic enzymes and cyclooxygenase (COX) inhibitory properties of essential oil (EO) of Stachys viticina Boiss. leaves. The S. viticina EO was isolated and identified using microwave-ultrasonic and GC-MS techniques, respectively. Fifty-two compounds were identified, of which endo-borneol was the major component, followed by eucalyptol and epizonarene. The EO was evaluated against a panel of in-vitro bioassays. The EO displayed antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli and Epidermophyton floccosum, with MIC values of 0.039, 0.078 and 0.78 mg/mL, respectively. The EO exhibited cytotoxicity against HeLa (cervical adenocarcinoma) and Colo-205 (colon) cancer cell lines with percentages of inhibition of 95% and 90%, for EO concentrations of 1.25 and 0.5 mg/mL, respectively. Furthermore, it showed metabolic enzyme (α-amylase, α-glucosidase, and lipase) inhibitory (IC50 = 45.22 ± 1.1, 63.09 ± 0.26, 501.18 ± 0.38 µg/mL, respectively) and antioxidant activity, with an IC50 value of 19.95 ± 2.08 µg/mL. Moreover, the S. viticina EO showed high cyclooxygenase inhibitory activity against COX-1 and COX-2 with IC50 values of 0.25 and 0.5 µg/mL, respectively, similar to those of the positive control (the NSAID etodolac). Outcomes amassed from this investigation illustrate that S. viticina EO represents a rich source of pharmacologically active molecules which can be further validated and explored clinically for its therapeutic potential and for the development and design of new natural therapeutic preparations. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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11 pages, 3637 KiB  
Article
β-Caryophyllene in the Essential Oil from Chrysanthemum Boreale Induces G1 Phase Cell Cycle Arrest in Human Lung Cancer Cells
by Kyung-Sook Chung, Joo Young Hong, Jeong-Hun Lee, Hae-Jun Lee, Ji Yeon Park, Jung-Hye Choi, Hee-Juhn Park, Jongki Hong and Kyung-Tae Lee
Molecules 2019, 24(20), 3754; https://doi.org/10.3390/molecules24203754 - 18 Oct 2019
Cited by 32 | Viewed by 3433
Abstract
Chrysanthemum boreale is a plant widespread in East Asia, used in folk medicine to treat various disorders, such as pneumonia, colitis, stomatitis, and carbuncle. Whether the essential oil from C. boreale (ECB) and its active constituents have anti-proliferative activities in lung cancer is [...] Read more.
Chrysanthemum boreale is a plant widespread in East Asia, used in folk medicine to treat various disorders, such as pneumonia, colitis, stomatitis, and carbuncle. Whether the essential oil from C. boreale (ECB) and its active constituents have anti-proliferative activities in lung cancer is unknown. Therefore, we investigated the cytotoxic effects of ECB in A549 and NCI-H358 human lung cancer cells. Culture of A549 and NCI-H358 cells with ECB induced apoptotic cell death, as revealed by an increase in annexin V staining. ECB treatment reduced mitochondrial membrane potential (MMP), disrupted the balance between pro-apoptotic and anti-apoptotic Bcl-2 proteins, and activated caspase-8, -9, and -3, as assessed by western blot analysis. Interestingly, pretreatment with a broad-spectrum caspase inhibitor (z-VAD-fmk) significantly attenuated ECB-induced apoptosis. Furthermore, gas chromatography–mass spectrometry (GC/MS) analysis of ECB identified six compounds. Among them, β-caryophyllene exhibited a potent anti-proliferative effect, and thus was identified as the major active compound. β- Caryophyllene induced G1 cell cycle arrest by downregulating cyclin D1, cyclin E, cyclin-dependent protein kinase (CDK) -2, -4, and -6, and RB phosphorylation, and by upregulating p21CIP1/WAF1 and p27KIP1. These results indicate that β-caryophyllene exerts cytotoxic activity in lung cancer cells through induction of cell cycle arrest. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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11 pages, 1396 KiB  
Communication
Characterization of Volatile Compounds in Four Different Rhododendron Flowers by GC×GC-QTOFMS
by Chen-Yu Qian, Wen-Xuan Quan, Zhang-Min Xiang and Chao-Chan Li
Molecules 2019, 24(18), 3327; https://doi.org/10.3390/molecules24183327 - 12 Sep 2019
Cited by 18 | Viewed by 3975
Abstract
Volatile compounds in flowers of Rhododendron delavayi, R. agastum, R. annae, and R. irroratum were analyzed using comprehensive two-dimensional gas chromatography-mass spectrometry (GC×GC) coupled with high-resolution quadrupole time-of-flight mass spectrometry (QTOFMS). A significantly increased number of compounds was separated by [...] Read more.
Volatile compounds in flowers of Rhododendron delavayi, R. agastum, R. annae, and R. irroratum were analyzed using comprehensive two-dimensional gas chromatography-mass spectrometry (GC×GC) coupled with high-resolution quadrupole time-of-flight mass spectrometry (QTOFMS). A significantly increased number of compounds was separated by GC×GC compared to conventional one-dimensional GC (1DGC), allowing more comprehensive understanding of the volatile composition of Rhododendron flowers. In total, 129 volatile compounds were detected and quantified. Among them, hexanal, limonene, benzeneacetaldehyde, 2-nonen-1-ol, phenylethyl alcohol, citronellal, isopulegol, 3,5-dimethoxytoluene, and pyridine are the main compounds with different content levels in all flower samples. 1,2,3-trimethoxy-5-methyl-benzene exhibits significantly higher content in R. irroratum compared to in the other three species, while isopulegol is only found in R. irroratum and R. agastum. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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17 pages, 2371 KiB  
Article
Chemical Composition of Two Different Lavender Essential Oils and Their Effect on Facial Skin Microbiota
by Marietta Białoń, Teresa Krzyśko-Łupicka, Ewa Nowakowska-Bogdan and Piotr P. Wieczorek
Molecules 2019, 24(18), 3270; https://doi.org/10.3390/molecules24183270 - 8 Sep 2019
Cited by 74 | Viewed by 11462
Abstract
Lavender oil is one of the most valuable aromatherapy oils, its anti-bacterial and anti-fungal activities can be explained by main components such as linalool, linalyl acetate, lavandulol, geraniol, or eucalyptol. The aim of the study was to assess the anti-microbial effects of two [...] Read more.
Lavender oil is one of the most valuable aromatherapy oils, its anti-bacterial and anti-fungal activities can be explained by main components such as linalool, linalyl acetate, lavandulol, geraniol, or eucalyptol. The aim of the study was to assess the anti-microbial effects of two different lavender oils on a mixed microbiota from facial skin. The commercial lavender oil and essential lavender oil from the Crimean Peninsula, whose chemical composition and activity are yet to be published, were used. Both oils were analysed by gas chromatography coupled to mass spectrometry. The composition and properties of studied oils were significantly different. The commercial ETJA lavender oil contained 10% more linalool and linalyl acetate than the Crimean lavender oil. Both oils also had different effects on the mixed facial skin microbiota. The Gram-positive bacilli were more sensitive to ETJA lavender oil, and Gram-negative bacilli were more sensitive to Crimean lavender oil. However, neither of the tested oils inhibited the growth of Gram-positive cocci. The tested lavender oils decreased the cell number of the mixed microbiota from facial skin, but ETJA oil showed higher efficiency, probably because it contains higher concentrations of monoterpenoids and monoterpenes than Crimean lavender oil does. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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13 pages, 3287 KiB  
Article
Identification and Allelopathy of Green Garlic (Allium sativum L.) Volatiles on Scavenging of Cucumber (Cucumis sativus L.) Reactive Oxygen Species
by Fan Yang, Xiaoxue Liu, Hui Wang, Rui Deng, Hanhan Yu and Zhihui Cheng
Molecules 2019, 24(18), 3263; https://doi.org/10.3390/molecules24183263 - 7 Sep 2019
Cited by 16 | Viewed by 3850
Abstract
Garlic and formulations containing allicin are used widely as fungicides in modern agriculture. However, limited reports are available on the allelopathic mechanism of green garlic volatile organic compounds (VOCs) and its component allelochemicals. The aim of this study was to investigate VOCs of [...] Read more.
Garlic and formulations containing allicin are used widely as fungicides in modern agriculture. However, limited reports are available on the allelopathic mechanism of green garlic volatile organic compounds (VOCs) and its component allelochemicals. The aim of this study was to investigate VOCs of green garlic and their effect on scavenging of reactive oxygen species (ROS) in cucumber. In this study, green garlic VOCs were collected by HS-SPME, then analyzed by GS-MS. Their biological activity were verified by bioassays. The results showed that diallyl disulfide (DADS) is the main allelochemical of green garlic VOCs and the DADS content released from green garlic is approximately 0.08 mg/g. On this basis, the allelopathic effects of green garlic VOCs in vivo and 1 mmol/L DADS on scavenging of ROS in cucumber seedlings were further studied. Green garlic VOCs and DADS both reduce superoxide anion and increase the accumulation of hydrogen peroxide of cucumber seedlings. They can also regulate active antioxidant enzymes (SOD, CAT, POD), antioxidant substances (MDA, GSH and ASA) and genes (CscAPX, CsGPX, CsMDAR, CsSOD, CsCAT, CsPOD) responding to oxidative stress in cucumber seedlings. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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16 pages, 2446 KiB  
Article
A Mass Spectrometry-Based Study Shows that Volatiles Emitted by Arthrobacter agilis UMCV2 Increase the Content of Brassinosteroids in Medicago truncatula in Response to Iron Deficiency Stress
by Idolina Flores-Cortez, Robert Winkler, Arturo Ramírez-Ordorica, Ma. Isabel Cristina Elizarraraz-Anaya, María Teresa Carrillo-Rayas, Eduardo Valencia-Cantero and Lourdes Macías-Rodríguez
Molecules 2019, 24(16), 3011; https://doi.org/10.3390/molecules24163011 - 20 Aug 2019
Cited by 4 | Viewed by 3326
Abstract
Iron is an essential plant micronutrient. It is a component of numerous proteins and participates in cell redox reactions; iron deficiency results in a reduction in nutritional quality and crop yields. Volatiles from the rhizobacterium Arthrobacter agilis UMCV2 induce iron acquisition mechanisms in [...] Read more.
Iron is an essential plant micronutrient. It is a component of numerous proteins and participates in cell redox reactions; iron deficiency results in a reduction in nutritional quality and crop yields. Volatiles from the rhizobacterium Arthrobacter agilis UMCV2 induce iron acquisition mechanisms in plants. However, it is not known whether microbial volatiles modulate other metabolic plant stress responses to reduce the negative effect of iron deficiency. Mass spectrometry has great potential to analyze metabolite alterations in plants exposed to biotic and abiotic factors. Direct liquid introduction-electrospray-mass spectrometry was used to study the metabolite profile in Medicago truncatula due to iron deficiency, and in response to microbial volatiles. The putatively identified compounds belonged to different classes, including pigments, terpenes, flavonoids, and brassinosteroids, which have been associated with defense responses against abiotic stress. Notably, the levels of these compounds increased in the presence of the rhizobacterium. In particular, the analysis of brassinolide by gas chromatography in tandem with mass spectrometry showed that the phytohormone increased ten times in plants grown under iron-deficient growth conditions and exposed to microbial volatiles. In this mass spectrometry-based study, we provide new evidence on the role of A. agilis UMCV2 in the modulation of certain compounds involved in stress tolerance in M. truncatula. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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11 pages, 693 KiB  
Article
The Profile of Urinary Headspace Volatile Organic Compounds After 12-Week Intake of Oligofructose-Enriched Inulin by Children and Adolescents with Celiac Disease on a Gluten-Free Diet: Results of a Pilot, Randomized, Placebo-Controlled Clinical Trial
by Natalia Drabińska, Elżbieta Jarocka-Cyrta, Norman Mark Ratcliffe and Urszula Krupa-Kozak
Molecules 2019, 24(7), 1341; https://doi.org/10.3390/molecules24071341 - 5 Apr 2019
Cited by 9 | Viewed by 3870
Abstract
The concentration of volatile organic compounds (VOCs) can inform about the metabolic condition of the body. In the small intestine of untreated persons with celiac disease (CD), chronic inflammation can occur, leading to nutritional deficiencies, and consequently to functional impairments of the whole [...] Read more.
The concentration of volatile organic compounds (VOCs) can inform about the metabolic condition of the body. In the small intestine of untreated persons with celiac disease (CD), chronic inflammation can occur, leading to nutritional deficiencies, and consequently to functional impairments of the whole body. Metabolomic studies showed differences in the profile of VOCs in biological fluids of patients with CD in comparison to healthy persons; however, there is scarce quantitative and nutritional intervention information. The aim of this study was to evaluate the effect of the supplementation of a gluten-free diet (GFD) with prebiotic oligofructose-enriched inulin (Synergy 1) on the concentration of VOCs in the urine of children and adolescents with CD. Twenty-three participants were randomized to the group receiving Synergy 1 (10 g per day) or placebo for 12 weeks. Urinary VOCs were analyzed using solid-phase microextraction and gas chromatography–mass spectrometry. Sixteen compounds were identified and quantified in urine samples. The supplementation of GFD with Synergy 1 resulted in an average concentration drop (36%) of benzaldehyde in urine samples. In summary, Synergy 1, applied as a supplement of GFD for 12 weeks had a moderate impact on the VOC concentrations in the urine of children with CD. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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12 pages, 885 KiB  
Article
GC-MS Analysis of the Composition of the Extracts and Essential Oil from Myristica fragrans Seeds Using Magnesium Aluminometasilicate as Excipient
by Inga Matulyte, Mindaugas Marksa, Liudas Ivanauskas, Zenona Kalvėnienė, Robertas Lazauskas and Jurga Bernatoniene
Molecules 2019, 24(6), 1062; https://doi.org/10.3390/molecules24061062 - 18 Mar 2019
Cited by 37 | Viewed by 8339
Abstract
Myristica fragrans (f. Myristicaceae) seeds are better known as a spice, but their chemical compounds may have a pharmacological effect. The yield of their composition of extracts and essential oils differs due to different methodologies. The aim of this study was to evaluate [...] Read more.
Myristica fragrans (f. Myristicaceae) seeds are better known as a spice, but their chemical compounds may have a pharmacological effect. The yield of their composition of extracts and essential oils differs due to different methodologies. The aim of this study was to evaluate an excipient material—magnesium aluminometasilicate—and to determine its influence on the qualitative composition of nutmeg extracts and essential oils. Furthermore, we wanted to compare the yield of essential oil. The extracts were prepared by maceration (M) and ultrasound bath-assisted extraction (UAE), and the essential oil—by hydrodistillation (HD). Conventional methods (UAE, HD) were modified with magnesium aluminometasilicate. The samples were analyzed by gas chromatography-mass spectrometry (GC-MS) method. From 16 to 19 chemical compounds were obtained using UAE with magnesium aluminometasilicate, while only 8 to 13 compounds were obtained using UAE without an excipient. Using our conditions and plant material, for the first time eight new chemical compounds in nutmeg essential oil were identified. Two of these compounds (γ-amorphene and cis-α-bergamotene) were obtained with the use of excipient, the other six (β-copaene, bergamotene, citronellyl decanoate, cubebol, cubenene, orthodene) by conventional hydrodistillation. Magnesium aluminometasilicate significantly increased the quantity of sabinene (from 6.53% to 61.42%) and limonene (from 0% to 5.62%) in essential oil. The yield of the essential oil from nutmeg seeds was significantly higher using magnesium aluminometasilicate; it increased from 5.25 ± 0.04% to 10.43 ± 0.09%. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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19 pages, 2602 KiB  
Article
Yeast Smell Like What They Eat: Analysis of Volatile Organic Compounds of Malassezia furfur in Growth Media Supplemented with Different Lipids
by Mabel Gonzalez, Adriana M. Celis, Marcela I. Guevara-Suarez, Jorge Molina and Chiara Carazzone
Molecules 2019, 24(3), 419; https://doi.org/10.3390/molecules24030419 - 24 Jan 2019
Cited by 13 | Viewed by 6357
Abstract
Malassezia furfur is part of the human skin microbiota. Its volatile organic compounds (VOCs) possibly contribute to the characteristic odour in humans, as well as to microbiota interaction. The aim of this study was to investigate how the lipid composition of the liquid [...] Read more.
Malassezia furfur is part of the human skin microbiota. Its volatile organic compounds (VOCs) possibly contribute to the characteristic odour in humans, as well as to microbiota interaction. The aim of this study was to investigate how the lipid composition of the liquid medium influences the production of VOCs. Growth was performed in four media: (1) mDixon, (2) oleic acid (OA), (3) oleic acid + palmitic acid (OA+PA), and (4) palmitic acid (PA). The profiles of the VOCs were characterized by HS-SPME/GC-MS in the exponential and stationary phases. A total number of 61 VOCs was found in M. furfur, among which alkanes, alcohols, ketones, and furanic compounds were the most abundant. Some compounds previously reported for Malassezia (γ-dodecalactone, 3-methylbutan-1-ol, and hexan-1-ol) were also found. Through our experiments, using univariate and multivariate unsupervised (Hierarchical Cluster Analysis (HCA) and Principal Component Analysis (PCA)) and supervised (Projection to Latent Structures Discriminant Analysis (PLS-DA)) statistical techniques, we have proven that each tested growth medium stimulates the production of a different volatiles profile in M. furfur. Carbon dioxide, hexan-1-ol, pentyl acetate, isomer5 of methyldecane, dimethyl sulphide, undec-5-ene, isomer2 of methylundecane, isomer1 of methyldecane, and 2-methyltetrahydrofuran were established as differentiating compounds among treatments by all the techniques. The significance of our findings deserves future research to investigate if certain volatile profiles could be related to the beneficial or pathogenic role of this yeast. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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Article
Volatile Compounds of Selected Raw and Cooked Brassica Vegetables
by Martyna N. Wieczorek and Henryk H. Jeleń
Molecules 2019, 24(3), 391; https://doi.org/10.3390/molecules24030391 - 22 Jan 2019
Cited by 41 | Viewed by 4904
Abstract
Brassica vegetables are a significant component of the human diet and their popularity is systematically increasing. The interest in plants from this group is growing because of numerous reports focused on their pro-health properties. However, some consumers are not enthusiastic about these vegetables [...] Read more.
Brassica vegetables are a significant component of the human diet and their popularity is systematically increasing. The interest in plants from this group is growing because of numerous reports focused on their pro-health properties. However, some consumers are not enthusiastic about these vegetables because of their specific bitter taste and sharp, sulfurous aroma. In this study, the volatile composition of 15 Brassica cultivars (five Brussels sprouts, four kohlrabi, three cauliflower and three broccoli), both raw and cooked, was analyzed by solid phase microextraction and comprehensive two-dimensional gas chromatography with time of flight mass spectrometry (SPME-GC×GC-ToFMS). Differences were found between the analyzed vegetables, as well as different cultivars of the same vegetable. Moreover, the influence of cooking on the composition of volatile compounds was evaluated. All the vegetables were frozen before analyses, which is why the impact of this process on the volatile organic compounds (VOCs) was included. The most abundant groups of compounds were sulfur components (including bioactive isothiocyanates), nitriles, aldehydes and alcohols. Cooking in general caused a decrease in the abundance of main volatiles. However, the amount of bioactive isothiocyanates increased in most cultivars after cooking. The effect of freezing on the volatile fraction was presented based on the Brussels sprout cultivars. Most of the changes were closely related to the activity of the lipoxygenase (LOX) pathway enzymes. These are characterized by a marked reduction in alcohol contents and an increment in aldehyde contents. Moreover, important changes were noted in the concentrations of bioactive components, e.g., isothiocyanates. This research included a large set of samples consisting of many cultivars of each analyzed vegetable, which is why it provides a considerable body of general information concerning volatiles in Brassica vegetables. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
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