Microwave-assisted solvent extraction and analysis of shikimic acid from plant tissues

Matallo, Marcus Barifouse; Almeida, S.D.B.; Cerdeira, A. L.; Franco, Daniel Andrade de Siqueira; Blanco, Flavio Martins Garcia; Menezes, P. T. C.; Luchini, Luiz Carlos; Moura, M. A. M.; Duke, Stephen O.

doi:10.1590/s0100-83582009000500012

Cited by 29 publications

(36 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In the specific case of glyphosate resistance, the accumulation of shikimic acid has been studied to assess the sensitivity of the enzyme EPSPs to the herbicide using chromatography and spectrophotometry (Zelaya et al, 2011). However, the extraction of shikimic acid directly from the plant tissue requires a long time and large amounts of reagents, so the methods of extraction in water, using solvent extraction assisted by microwave, have been presented as a simple form of shikimic acid extraction (Matallo et al 2009). Another way to evaluate the resistance to glyphosate is the inhibitory effect of plant photosynthesis (Duke et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Glyphosate influence on the physiological parameters of Conyza bonariensis biotypes

et al. 2014

View full text Add to dashboard Cite

-The objective of this study was to determine changes in gas exchange and inhibition of EPSPs, based on the accumulation of shikimic acid in horseweed biotypes resistant and sensitive to glyphosate. Two experiments were conducted in a factorial model. The first one evaluated horseweed biotypes (one resistant and one susceptible to glyphosate), and herbicide rates (0 and 1,080 g a.e. ha 1 ) applied on the weed. In the second experiment, the horseweed biotypes (susceptible and resistant to glyphosate) were evaluated in five periods as following: 0, 3, 7, 10, and 14 days after herbicide application (DAH). The photosynthetic rate, transpiration, carboxylation efficiency, and water efficiency were determined using an infrared gas analyzer (IRGA), and shikimic acid concentration by HPLC. The application of glyphosate damaged the photosynthetic parameters of the susceptible biotype, causing complete inhibition of the photosynthetic rate, transpiration rate, carboxylation efficiency and water use efficiency, starting from the 7 DAH. On the other hand, total inhibition of the photosynthetic parameters was not observed for the resistant biotype. Shikimic acid accumulation occurred in both biotypes after glyphosate application but the susceptible biotype had the highest concentrations, indicating greater sensitivity of the enzyme EPSPs. The accumulation of shikimic acid in the resistant biotype indicates that the mechanism of resistance is not related to the total insensitivity of the enzyme EPSPs to glyphosate and/or that other resistance mechanisms may be involved.Keywords: hairy fleabane, resistance, photosynthesis, EPSPs, shikimic acid. RESUMO -Objetivou-se neste trabalho determinar alterações na fotossíntese e na inibição da EPSPs

show abstract

Section: Introductionmentioning

confidence: 99%

Glyphosate influence on the physiological parameters of Conyza bonariensis biotypes

et al. 2014

View full text Add to dashboard Cite

show abstract

“…al. [41]. At 3, 6, 9, and 12 days after treatments, the leaves were collected, always in the morning, dried in a forced air circulation oven at 60°C for 48 h, and then crushed at 25 000 rpm (IKA A11 Basic), frozen at temperatures ≤ 10°C, stored in polystyrene boxes, sealed, and transported to the laboratory.…”

Section: Samplesmentioning

confidence: 99%

Untitled

2017

Planta Med Lett

View full text Add to dashboard Cite

!Shikimic acid is a natural organic compound produced in the biochemical pathways of eukaryotic organisms and is generally utilized as a starting material of the antiviral drug Oseltamivir (Tamiflu ® ). This study shows the results of shikimic acid accumulation in Brachiaria plantaginea, an abundant, grassy plant found in Brazil and other countries in Africa and America, after glyphosate spraying at three different doses. B. plantaginea plants harvested after 6 days of exposure to the herbicide showed that shikimic acid accumulation increased by 345 %, on average, compared to unsprayed plants. The combination of near infrared spectroscopy and multivariate analysis using partial least square regression was applied for the quantification of shikimic acid in B. plantaginea. Spectra of 44 samples were obtained using the diffuse reflectance mode in the range of 4000 to 10 000 cm −1 with 4 cm −1 resolution. Different mathematical pretreatments were applied to the spectra. As preprocessing, the data were mean-centered. The calibration model with seven factors on twenty-nine samples (training set) exhibited a coefficient of determination = 0.9930 and a standard error of calibration = 84.05. For external validation (11 samples on the test set), the coefficient of determination = 0.9317 and the standard error of prediction = 154.91. The percent calibration error range was 1 to 10 % for most of the samples and only two samples presented an error greater than 20 %. For external validation, the mean prediction error was 10% and the range error ratio was 9.42, indicating that the model is qualified for screening calibration.

show abstract

“…The shikimic acid extraction technique of plant tissues of soybean and sugarcane using water and extraction assisted by microwave, developed by Matallo et al (2009), has promoted a high extraction efficiency, near 100%, and a high level of sensitivity without interference from other compounds and without the use of more toxic reagents such as sulfuric acid, hydrochloric acid and alcohols. …”

Section: Extraction Of Compoundsmentioning

confidence: 99%

“…Several methods for determination of some of these compounds are reported both by spectrophotometry (Zelaya et al, 2011) and by liquid chromatography coupled to mass spectrometry (Raji et al, 2014) and detection by fluorescence (Zhang et al, 2013), or arrangement of photodiodes (Matallo et al, 2009;Alcaide-Molina et al, 2013) and gas chromatography with mass detector (Catrinck et al, 2013). However, the adoption of only one method of extraction and quantification of glyphosate, AMPA (aminomethylphosphonic acid) and compounds related to the shikimic acid pathway has not been reported.…”

Section: Introductionmentioning

confidence: 99%

Extraction and Simultaneous Determination of Glyphosate, AMPA and Compounds of the Shikimic Acid Pathway in Plants

et al. 2015

View full text Add to dashboard Cite

-This study has aimed to develop a method for simultaneous extraction and determination by liquid chromatography and mass spectrometry (LC-MS/MS) of glyphosate, aminomethylphosphonic acid (AMPA), shikimic acid, quinic acid, phenylalanine, tyrosine and tryptophan. For the joint analysis of these compounds the best conditions of ionization in mass spectrometry and for chromatographic separation of the compounds were selected. Calibration curves and linearity ranges were also determined for each compound. Different extraction systems of the compounds were tested from plant tissues collected from sugarcane (Saccharum officinarum) and eucalyptus (Eucalyptus urophylla platiphylla) plants two days after the glyphosate application at the dose of 720 g a.e. ha -1 . The plant material was dried in a forced air circulation drying oven and in a lyophilizer, and subsequently the extractions with acidified water (pH 2.5), acetonitrile-water (50:50) [v/v] and methanol-water (50:50) [v/v] were tested. To verify the recovery of the compounds in the plant matrix with acidified water as an extracting solution, the samples were fortified with a solution containing the mixture of the different analytical standards present so that this one presented the same levels of 50 and 100 μg L -1 of each compound. All experiments were conducted with three replicates. The analytical method developed was efficient for compounds quantifications. The extraction from the samples dried in an oven and using acidified water allowed better extraction levels for all compounds. The recovery levels of the compounds in the fortified samples with known amounts of each compound for both plants samples were rather satisfactory.Keywords: herbicide, LC-MS/MS, metabolites, metabolic profile. (pH 2,5), acetonitrila-água (50:50) [v/v] e metanol-água (50:50) [v/v] RESUMO -Este trabalho teve como objetivo o desenvolvimento de um método de extração e determinação simultânea por cromatografia líquida e espectrometria de massas (LC-MS/MS) de glyphosate, ácido aminometilfosfônico (AMPA), ácido chiquímico, ácido quínico, fenilalanina, tirosina e triptofano. Para a análise conjunta desses compostos, foram selecionadas as melhores condições de ionização no espectrômetro de massas e para a separação cromatográfica dos compostos. Também foram determinadas as curvas de calibração e faixas de linearidade para cada um dos compostos. Foram testados diferentes sistemas de extração dos compostos a partir de tecidos vegetais coletados de planta de cana-de-açúcar (Saccharum officinarum) e eucalipto (Eucalyptus

show abstract

Microwave-assisted solvent extraction and analysis of shikimic acid from plant tissues

Cited by 29 publications

References 19 publications

Glyphosate influence on the physiological parameters of Conyza bonariensis biotypes

Glyphosate influence on the physiological parameters of Conyza bonariensis biotypes

Untitled

Extraction and Simultaneous Determination of Glyphosate, AMPA and Compounds of the Shikimic Acid Pathway in Plants

Contact Info

Product

Resources

About