Characterization of chemical compounds susceptible to be extracted from cork by the wine using GC-MS and 1H NMR metabolomic approaches

Pinto, Joana; Oliveira, Ana Sofia; Lopes, Paulo; Roseira, Isabel; Cabral, Miguel; Bastos, Maria de Lourdes; Pinho, Paula Guedes de

doi:10.1016/j.foodchem.2018.07.222

Cited by 29 publications

(31 citation statements)

References 25 publications

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“…The neutral fraction of the MeOH/CH 2 Cl 2 (1:1) extract of stem bark of B. obscura was subjected to column chromatography (CC) over silica gel to afford beilschmiedol B ( 1 ), beilschmiedol C ( 2 ), and obscurene A ( 3 ). In addition, four known compounds including pentacosan-1-ene ( 4 ) [ 9 , 10 ], 15-phenylpentadecanoic acid ( 5 ) [ 11 ], (3 S ,4 R ,5 S )-4-hydroxy-5-methyl-3-(11′-phenyl-1′- n -undecyl)-butanolide ( 6 ), and (3 S ,4 R ,5 S )-4-hydroxy-5-methyl-3-(13′-phenyl-1′- n -tridecyl)-butanolide ( 7 ) [ 12 ] were isolated.…”

Section: Resultsmentioning

confidence: 99%

“…Phytochemical investigation of the MeOH/CH 2 Cl 2 (1:1) extract of the roots and leaves of Beilschmiedia louisii and B. obscura, which showed potent antitrypanosomal activity during preliminary screening on T. brucei led to the isolation of a mixture of two new endiandric acid derivatives 1 and 2, and one new phenylalkene (3) along with twelve known compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15). In addition, four new derivatives (11a, 11b, 11c, and 11d) were synthesized from compound 11.…”

Section: Discussionmentioning

confidence: 99%

“…Its molecular formula was assigned as C 25 H 50 (one degree of unsaturation) according to HRESIMS, which showed a deprotonated molecular ion peak [M − H] + at m/z 349.1892. The broad band decoupled 13 C-NMR spectrum (Table 4; Figure S31 and from the cork of the wine through gas chromatography-mass spectrometry (GCMS) [9,10] is isolated here for the first time and its NMR data reported.…”

Section: Structure Elucidationmentioning

confidence: 97%

“…The neutral fraction of the MeOH/CH 2 Cl 2 (1:1) extract of roots of B. louisii was subjected to CC over silica gel to afford eight known compounds including beilschmiedic acid A (8), beilschmiedic acid C (9), beilschmiedic acid D (10), beilschmiedic acid E (11) [13,14], methylenedioxyendiandric acid A (12) [15], β-sitosterol (13) [16], epicatechin (14) [17], and β-sitosterol-3-O-β-D-glucopyranoside (15) [18]. Furthermore, four new derivatives (11a, 11b, 11c, and 11d) were prepared from compound 11.…”

Section: Structure Elucidationmentioning

confidence: 99%

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Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae)

et al. 2020

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The MeOH/CH2Cl2 (1:1) extracts of the roots and leaves of Beilschmiedia louisii and B. obscura showed potent antitrypanosomal activity during preliminary screening on Trypanosoma brucei brucei. Phytochemical investigation of these extracts led to the isolation of a mixture of two new endiandric acid derivatives beilschmiedol B (1) and beilschmiedol C (2), and one new phenylalkene obscurene A (3) together with twelve known compounds (4–15). In addition, four new derivatives (11a–11d) were synthesized from compound 11. Their structures were elucidated based on their NMR and MS data. Compounds 5, 6, and 7 were isolated for the first time from the Beilschmiedia genus. Additionally, the NMR data of compound 4 are given here for the first time. The isolates were evaluated for their antitrypanosomal and antimalarial activities against Tb brucei and the Plasmodium falciparum chloroquine-resistant strain Pf3D7 in vitro, respectively. From the tested compounds, the mixture of new compounds 1 and 2 exhibited the most potent antitrypanosomal activity in vitro with IC50 value of 4.91 μM.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Structure Elucidationmentioning

confidence: 97%

Section: Structure Elucidationmentioning

confidence: 99%

See 2 more Smart Citations

Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae)

et al. 2020

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“…The unique properties of cork, including long-lasting flexibility, hydrophobicity and gas permeability, make it still today the first choice for wine producers as a closure for bottled wine [ 1 , 2 ]. The complex chemical composition of cork, together with its importance in the wine industry, has resulted in the investigation of extractable compounds that can be released from the cork into the solution having become a subject of great interest [ 3 , 4 , 5 ]. Within the extractable components, volatiles including terpenes, alcohols, aldehydes and pyrazines, among others, deserve special attention [ 6 , 7 , 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Investigation of Volatiles in Cork Samples Using Chromatographic Data and the Superposing Significant Interaction Rules (SSIR) Chemometric Tool

Besalú

Prat²,

Anticó

2020

Biomolecules

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This study describes a new chemometric tool for the identification of relevant volatile compounds in cork by untargeted headspace solid phase microextraction and gas chromatography mass spectrometry (HS-SPME/GC-MS) analysis. The production process in cork industries commonly includes a washing procedure based on water and temperature cycles in order to reduce off-flavors and decrease the amount of trichloroanisole (TCA) in cork samples. The treatment has been demonstrated to be effective for the designed purpose, but chemical changes in the volatile fraction of the cork sample are produced, which need to be further investigated through the chemometric examination of data obtained from the headspace. Ordinary principal component analysis (PCA) based on the numerical description provided by the chromatographic area of several target compounds was inconclusive. This led us to consider a new tool, which is presented here for the first time for an application in the chromatographic field. The superposing significant interaction rules (SSIR) method is a variable selector which directly analyses the raw internal data coming from the spectrophotometer software and, combined with PCA and discriminant analysis, has been able to separate a group of 56 cork samples into two groups: treated and non-treated. This procedure revealed the presence of two compounds, furfural and 5-methylfurfural, which are increased in the case of treated samples. These compounds explain the sweet notes found in the sensory evaluation of the treated corks. The model that is obtained is robust; the overall sensitivity and specificity are 96% and 100%, respectively. Furthermore, a leave-one-out cross-validation calculation revealed that all of the samples can be correctly classified one at a time if three or more PCA descriptors are considered.

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Chemometrics Applied to Nuclear Magnetic Resonance Analysis

Beavis

Rusilowicz

Donarski

et al. 2019

Encyclopedia of Analytical Chemistry

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Nuclear magnetic resonance (NMR) spectroscopy provides information about the physical and chemical properties of atoms within a sample and has become an essential tool in metabolomics. Although less sensitive than mass spectrometry, NMR spectroscopy is highly reproducible and gives wider coverage in comparison to other techniques used for the analysis of complex mixtures. Recent advances in technology, advances in methodology, and increased computer power have increased the need to develop mathematical and statistical methods to analyze and interpret the complex datasets acquired. This has resulted in developments in the field of chemical informatics known as chemometrics . In contrast to targeted analyses, chemometric approaches do not initially attempt to identify particular metabolites. Instead, statistical techniques and pattern recognition methods are used to identify spectral features that show consistent trends or provide discrimination between classes. These features can provide a fingerprint for a metabolic state to be used, for example, for disease diagnostics, and individual features of interest can then be related to specific compounds and metabolic pathways using database searches. NMR‐based chemometric methods are now used in a wide range of applications including clinical diagnostics, food science and traceability, process control, monitoring genetic modification, and predicting the side effects of pharmaceuticals and their environmental effects.

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Characterization of chemical compounds susceptible to be extracted from cork by the wine using GC-MS and 1H NMR metabolomic approaches

Cited by 29 publications

References 25 publications

Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae)

Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae)

Investigation of Volatiles in Cork Samples Using Chromatographic Data and the Superposing Significant Interaction Rules (SSIR) Chemometric Tool

Chemometrics Applied to Nuclear Magnetic Resonance Analysis

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