Deciphering the chemical origin of the semen-like floral scents in three angiosperm plants

Zhang, Xiaoping; Chingin, Konstantin; Zhong, Dacai; Li, Luo; Frankevich, Vladimir; Chen, Huanwen

doi:10.1016/j.phytochem.2017.11.001

Cited by 13 publications

(7 citation statements)

References 47 publications

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“…Ambient ionization corona discharge ionization MS of VOCs occurs in a ladder‐like fashion in which protons are gradually transferred from compounds with lower PA values to compounds with high‐PA values, which favors the observation of high‐PA compounds, such as N ‐(2‐hydroxyethyl) octanamide, even when present at a trace level undetectable by GC/MS. Similarly, in our previous study using ambient corona discharge ionization MS we identified eleven nitrogenous volatiles emitted by the flowers of three different angiosperm plants with semen‐like fragrance, including 1‐pyrroline, 1‐piperidine, 4‐aminobutanal, and 2‐ethylpyridine, which have not been reported in earlier GC/MS studies . Altogether, this shows good prospects for ambient floral VOCs analysis as an alternative or complement to GC/MS.…”

Section: Resultssupporting

confidence: 71%

“…MS experiments were performed on an Orbitrap‐XL mass spectrometer (Thermo Scientific, San Jose, CA, USA) using a home‐made APCI source as detailed in our earlier studies coupled to a home‐made ambient neutral desorption (ND) device, which is used to extract the fragrance compounds from the O. fragrans flowers. The experimental ND‐EAPCI‐MS protocol is shown schematically in Figure .…”

Section: Methodsmentioning

confidence: 99%

“…MS experiments were performed on an Orbitrap-XL mass spectrometer (Thermo Scientific, San Jose, CA, USA) using a homemade APCI source as detailed in our earlier studies 20,21,23,24 coupled to a home-made ambient neutral desorption (ND) device, which is…”

Section: Instruments and Working Conditionsmentioning

confidence: 99%

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Floral volatiles identification and molecular differentiation of Osmanthus fragrans by neutral desorption extractive atmospheric pressure chemical ionization mass spectrometry

Zhang

Liu

Wang

et al. 2019

Rapid Comm Mass Spectrometry

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Rationale Floral volatiles are commonly present only at trace amounts and can be degraded or lost during vapor collection, which is often challenging from the analytical standpoint. Osmanthus fragrans Lour. is a widely cultivated plant known for the highly distinct fragrance of its flowers. The identification of specific volatile organic compounds (VOCs) and molecular differentiation of O. fragrans without any chemical pretreatment and VOC collection are important. Methods Twenty‐eight VOCs released by the flowers from ten different cultivars of O. fragrans were identified using neutral desorption extractive atmospheric pressure chemical ionization mass spectrometry (ND‐EAPCI‐MS) without any chemical pretreatment or VOC collection. Chemical identification was performed by high‐resolution MSn analysis and whenever possible was confirmed by the analysis of standards. Results According to our literature search, nine of the identified VOCs, 3‐buten‐2‐one, cyclohexadiene, 2‐methylfuran, 3‐allylcyclohexene, cuminyl alcohol, hotrienol oxide, epoxy‐linalool oxide, N‐(2‐hydroxyethyl) octanamide, and 3‐hydroxy‐dihydro‐β‐ionone, have not been reported in O. fragrans in earlier studies. Confident differentiation between ten different cultivars of O. fragrans was achieved by the principal component analysis of the mass spectrometric results. Conclusions The results of our ND‐EAPCI‐MS analysis substantially increase our knowledge about the chemistry of the O. fragrans floral fragrance and demonstrate the power of this technique for direct molecular profiling for plant recognition or in biotechnological applications.

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Section: Resultssupporting

confidence: 71%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Floral volatiles identification and molecular differentiation of Osmanthus fragrans by neutral desorption extractive atmospheric pressure chemical ionization mass spectrometry

Zhang

Liu

Wang

et al. 2019

Rapid Comm Mass Spectrometry

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“…It also showed four methylene protons at δ H 4.05 (2H, m, H-8), 2.66 (2H, m, H-9), 1.95 (m, 1H, H-15a) and 1.75 (m, 1H, H-15b), five methine protons at 5.85 (1H, s, H-2), 4.83 (1H, m, H-5), 3.6 (1H, m, H-7), 3.6 (1H, m, H-7), 2.92 (1H, brs, H-16); The 13 C NMR spectra (Table 2) indicated the presence of two carbonyl carbons ( δ C 174.3 and 193.0), a pair of olefinic carbons ( δ C 174.3 and 193.0), five methyl carbons ( δ C 22.2*2, 20.7, 13.4 and 8.2), one oxygenated methylene proton carbon ( δ C 58.9), three methylene carbons ( δ C 46.4, 32.4 and 23.5). The 1 H and 13 C NMR spectra of 2 were similar to those of 4-methyl-5,6-dihydro-2H-pyran-2-one except for the absence of two side chains 25,26 . The planar structure of 2 (Fig.…”

Section: Resultsmentioning

confidence: 73%

New antimicrobial compounds produced by Seltsamia galinsogisoli sp. nov., isolated from Galinsoga parviflora as potential inhibitors of FtsZ

Zhang

et al. 2019

Sci Rep

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A total amount of 116 fungal strains, belonging to 30 genera, were acquired from the rhizosphere soil and plant of Galinsoga parviflora . A strain SYPF 7336, isolated from the rhizospheric soil, was identified as Seltsamia galinsogisoli sp. nov., by morphological and molecular analyses, which displayed high antibacterial activity. In order to study the secondary metabolites of Seltsamia galinsogisoli sp. nov., nine compounds were successfully seperated from the strain fermentation broth, including two new compounds and seven known compounds. Their structures were elucidated based on spectral analysis including 1D and 2D NMR. All the seperated compounds were evaluated for their antimicrobial activities. Compounds 2, 5 and 1 displayed antimicrobial activities against Staphylococcus aureus with MIC values of 25, 32 and 75 μg/mL, respectively. Moreover, morphological observation showed the coccoid cells of S. aureus to be swollen to a volume of 1.4 to 1.7-fold after treatment with compounds 1 , 2 and 5 , respectively. Molecular docking was carried out to investigate interactions of filamentous temperature-sensitive protein Z (FtsZ) with compounds 1 , 2 and 5 .

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“…In the investigation of VOCs originating in plants, a remarkable example is a study that employed direct ambient corona discharge ionization mass spectrometry for the characterization of volatiles coming from flowers of selected species ( Photinia serrulata , Castanopsis sclerophylla and Stemona japonica ) with insect semen-like odor without any further sample preparation. Such research found some compounds that were not previously identified by GC-MS for the species under investigation [123].…”

Section: Instrumental Analytical Techniquesmentioning

confidence: 99%

Tools in the Investigation of Volatile Semiochemicals on Insects: From Sampling to Statistical Analysis

Barbosa-Cornelio

Cantor

Coy-Barrera

et al. 2019

Insects

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The recognition of volatile organic compounds (VOCs) involved in insect interactions with plants or other organisms is essential for constructing a holistic comprehension of their role in ecology, from which the implementation of new strategies for pest and disease vector control as well as the systematic exploitation of pollinators and natural enemies can be developed. In the present paper, some of the general methods employed in this field are examined, focusing on their available technologies. An important part of the investigations conducted in this context begin with VOC collection directly from host organisms, using classical extraction methods, by the employment of adsorption materials used in solid-phase micro extraction (SPME) and direct-contact sorptive extraction (DCSE) and, subsequently, analysis through instrumental analysis techniques such as gas chromatography (GC), nuclear magnetic resonance (NMR) and mass spectrometry (MS), which provide crucial information for determining the chemical identity of volatile metabolites. Behavioral experiments, electroantennography (EAG), and biosensors are then carried out to define the semiochemicals with the best potential for performing relevant functions in ecological relationships. Chemical synthesis of biologically-active VOCs is alternatively performed to scale up the amount to be used in different purposes such as laboratory or field evaluations. Finally, the application of statistical analysis provides tools for drawing conclusions about the type of correlations existing between the diverse experimental variables and data matrices, thus generating models that simplify the interpretation of the biological roles of VOCs.

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Deciphering the chemical origin of the semen-like floral scents in three angiosperm plants

Cited by 13 publications

References 47 publications

Floral volatiles identification and molecular differentiation of Osmanthus fragrans by neutral desorption extractive atmospheric pressure chemical ionization mass spectrometry

Floral volatiles identification and molecular differentiation of Osmanthus fragrans by neutral desorption extractive atmospheric pressure chemical ionization mass spectrometry

New antimicrobial compounds produced by Seltsamia galinsogisoli sp. nov., isolated from Galinsoga parviflora as potential inhibitors of FtsZ

Tools in the Investigation of Volatile Semiochemicals on Insects: From Sampling to Statistical Analysis

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