Fragmentation and Reaction Rate Constants of Terpenoids Determined by Proton Transfer Reaction-mass Spectrometry

Tani, Atsushi

doi:10.2525/ecb.51.23

Cited by 32 publications

(28 citation statements)

References 27 publications

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“…Significant fragmentation was observed in the PTR-TOF upon injection of starting materials into a clean reactor. α-Phellandrene was detected at m/z 137 at 32-34 % depending on drift tube conditions, consistent with fragmentation observed in the PTR-MS studies of Misztal et al (2012) and Tani (2013) (Supplement Sect. S2).…”

Section: Characterisation Of Gas and Particle Phasessupporting

confidence: 59%

“…PTR-TOF spectra were collected at a time resolution of 2 s. Data were processed using the PTR-TOF data analyser (Müller et al, 2013), with 30 spectra averaged to improve counts of trace species. A generic H 3 O + rate constant of 2×10 −9 cm 3 s −1 was used for conversion into ppb, except for those species where experimental or theoretical data exist (Cappellin et al, 2012;Tani, 2013).…”

Section: Characterisation Of Gas and Particle Phasesmentioning

confidence: 99%

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Ozonolysis of <i>α</i>-phellandrene – Part 1: Gas- and particle-phase characterisation

et al. 2017

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Abstract. The ozonolysis of α-phellandrene, a highly reactive conjugated monoterpene largely emitted by Eucalypt species, is characterised in detail for the first time using a smog chamber at the Guangzhou Institute of Geochemistry, Chinese Academy of Sciences. Gas-phase species were monitored by a proton-transfer-reaction time-of-flight mass spectrometer (PTR-TOF), with yields from a large number of products obtained, including formaldehyde (5-9 %), acetaldehyde (0.2-8 %), glyoxal (6-23 %), methyl glyoxal (2-9 %), formic acid (22-37 %) and acetic acid (9-22 %). Higher m/z second-generation oxidation products were also observed, with products tentatively identified according to a constructed degradation mechanism. OH yields from α-phellandrene and its first-generation products were found to be 35 ± 12 and 15 ± 7 %, respectively, indicative of prominent hydroperoxide channels. An average first-generation rate coefficient was determined as 1.0 ± 0.7 × 10 −16 cm 3 molecule −1 s −1 at 298 K, showing ozonolysis as a dominant loss process for both α-phellandrene and its first-generation products in the atmosphere. Endocyclic conjugation in α-phellandrene was also found to be conducive to the formation of highly condensible products with a large fraction of the carbon mass partitioning into the aerosol phase, which was monitored with a scanning mobility particle sizer (SMPS) and a high-resolution timeof-flight aerosol mass spectrometer (AMS). Nucleation was observed almost instantaneously upon ozonolysis, indicating the rapid formation of extremely low-volatility compounds. Particle nucleation was found to be suppressed by the addition of either NO 2 or a Criegee scavenger, with it being proposed that stabilised Criegee intermediates are important for new particle formation in the system. Aerosol yields ranged from 25 to 174 % depending on mass loadings, with both first-and second-generation products identified as large contributors to the aerosol mass. In short, with a high chemical reactivity and aerosol-forming propensity, α-phellandrene is expected to have an immediate impact on the local environment to which it is emitted, with ozonolysis likely to be an important contributor to the significant blue haze and frequent nocturnal nucleation events observed over Eucalypt forests.

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Section: Characterisation Of Gas and Particle Phasessupporting

confidence: 59%

Section: Characterisation Of Gas and Particle Phasesmentioning

confidence: 99%

Ozonolysis of <i>α</i>-phellandrene – Part 1: Gas- and particle-phase characterisation

et al. 2017

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“…Concentration (ppbv) of signals belonging to the terpene group detected in 12 different essential oils extracted from each resin. (A) Signal intensity of the masses m/z 69 (isoprene), m/z 137 (monoterpenes), m/z 205 (sesquiterpenes) and m/z 273 (diterpenes); (B ) signal intensity of oxygenated monoterpenes ( m/z 151, m/z 153, m/z 155 and m/z 157) and oxygenated sesquiterpenes ( m/z 221); (C ) the principal terpene fragments following the main terpene pattern fragmentation showed in []…”

Section: Resultsmentioning

confidence: 99%

“…Peak shape and quantification, fitting algorithms for each spectrum, and acquisition of raw data were performed according to a procedure discussed by Cappellin et al A threshold of 0.50 ppbv was set to eliminate all compounds present in the background. After processing and filtering, a total of 142 different peaks were obtained and putatively identified, based on both: (a) the high mass accuracy provided by the PTR‐ToF‐MS, which was sufficient for the sum formula identification, and (b) comparison of the measured masses with those reported in the literature on the composition and quantification of plant volatiles …”

Section: Methodsmentioning

confidence: 91%

Correlation between VOC fingerprinting and antimicrobial activity of several essential oils extracted by plant resins against A. tumefaciens and P. savastanoi

Caparrotta

Comparini

Marone

et al. 2019

Flavour & Fragrance J

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The present work aimed to assess the antimicrobial activity of twelve essential oils extracted from plant resins of trees that grow in several tropical and subtropical regions of the world. Eleven essential oils were extracted from resins of plant belonging to the Burseraceae family (the genera Boswellia, Commiphora, Canarium and Bursera); the remaining oil was extracted from a resinous plant belonging to the Fabaceae family (genus Hymenea). The extraction was carried out using a conventional distillation method. The volatile organic compounds (VOCs) of each essential oil were analyzed with PTR‐ToF‐MS (proton transfer reaction time‐of‐flight mass spectrometry) and the antimicrobial activity was evaluated against the phytopathogens Agrobacterium tumefaciens and Pseudomonas savastanoi pv. savastanoi. The essential oils obtained from Boswellia papyrifera, B. dalzielii, B. frereana and B. rivae were the most abundant in terms of signal intensity and VOC number in comparison with the other analyzed essential oils. Furthermore, B. neglecta shared a common volatile profile with the Canarium species, as was demonstrated previously in the literature. Greater bacterial growth inhibition of A. tumefaciens was detected with the essential oils extracted from plants belonging to Boswellia species while less action was observed against P. savastanoi. Finally, a positive correlation was found between terpenes and terpenoid compounds and bacterial growth inhibition, suggesting these essential oils as a new source of bioactive compounds for the prevention, protection and treatment of plant diseases.

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“…Graus et al 33 monoterpenes and isoprene) using the models of fragmentation available in the literature ( Table 2). [35][36][37][38][39][40][41] Subsequently, all signals were converted on the basis of primary ion signal from cps to ppbv. 42 Finally, the dataset was cleaned and all peaks ascribed to water chemistry or other interfering ions (e.g.…”

Section: Ptr-tof-ms Data Analysismentioning

confidence: 99%

Volatome analysis approach for the taxonomic classification of tree exudate collection using Proton Transfer Reaction Time of Flight Mass Spectrometry

Taiti

Costa²,

Figorilli³

et al. 2018

Flavour & Fragrance J

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Natural resins exude from trees as viscous liquids, which subsequently harden by evaporation and/or oxidation. Their compositions and textures are complex and vary during the solidification processes, producing a typical volatile fragrant fraction. Many techniques have been applied to the study of resins in order to obtain considerable chemical information but no exploratory work has been conducted using Proton Transfer Reaction Time of Flight Mass Spectrometry (PTR‐ToF‐MS). For this reason its potential to rapidly obtain the Volatiles Organic Compounds (VOCs) mass profiles of several natural resins has been tested. A Partial Least Squares Discriminant Analysis (PLSDA) have been performed to classify all samples based on their species, family or order on the basis of the VOCs emission profiles of 31 natural resins derived from different tree species. The sensitivities and specificities obtained were higher than 95% whilst a correct classification was higher for family (94.23% on 7 classes) and order (94.12% on 6 classes), than that of species (89.06% on 31 classes). Finally confusion matrices based on PLSDA models were produced to observe and draw conclusions about non‐correct classifications. In our study we successfully determined the volatile profiles for 31 different tree natural resins assessing the possibility of correctly identify the taxonomic position of the trees by the analysis of their aromatic profiles. This preliminary study could lay down the bases for future studies on the VOC emissions of resins, by qualifying PTR‐ToF‐MS as a promising tool for a fast resin identification of complex matrix.

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Fragmentation and Reaction Rate Constants of Terpenoids Determined by Proton Transfer Reaction-mass Spectrometry

Cited by 32 publications

References 27 publications

Ozonolysis of <i>α</i>-phellandrene – Part 1: Gas- and particle-phase characterisation

Ozonolysis of <i>α</i>-phellandrene – Part 1: Gas- and particle-phase characterisation

Correlation between VOC fingerprinting and antimicrobial activity of several essential oils extracted by plant resins against A. tumefaciens and P. savastanoi

Volatome analysis approach for the taxonomic classification of tree exudate collection using Proton Transfer Reaction Time of Flight Mass Spectrometry

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Fragmentation and Reaction Rate Constants of Terpenoids Determined by Proton Transfer Reaction-mass Spectrometry

Cited by 32 publications

References 27 publications

Ozonolysis of &lt;i&gt;α&lt;/i&gt;-phellandrene – Part 1: Gas- and particle-phase characterisation

Ozonolysis of &lt;i&gt;α&lt;/i&gt;-phellandrene – Part 1: Gas- and particle-phase characterisation

Correlation between VOC fingerprinting and antimicrobial activity of several essential oils extracted by plant resins against A. tumefaciens and P. savastanoi

Volatome analysis approach for the taxonomic classification of tree exudate collection using Proton Transfer Reaction Time of Flight Mass Spectrometry

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Ozonolysis of <i>α</i>-phellandrene – Part 1: Gas- and particle-phase characterisation

Ozonolysis of <i>α</i>-phellandrene – Part 1: Gas- and particle-phase characterisation