Copaifera langsdorffii supercritical fluid extraction: Chemical and functional characterization by LC/MS and in vitro assays

Costa, Ana Lúcia Siqueira; Freitas, Luís Alexandre Pedro de; Mendiola, J. A.; Ibáñez, Elena

doi:10.1016/j.supflu.2015.02.028

Cited by 26 publications

(9 citation statements)

References 49 publications

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“…There are a few reports on the detection of KA by LC–MS or LC–MS/MS [11] , [12] , but no reports have quantified KA with the MRM method. At first, we observed the fragmentation of authentic KA with a single scan mode of LC–MS/MS (ionization, ESI; negative mode).…”

Section: Resultsmentioning

confidence: 99%

Analysis of ent-kaurenoic acid by ultra-performance liquid chromatography-tandem mass spectrometry

Miyazaki

Kimura

Natsume

et al. 2015

Biochemistry and Biophysics Reports

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ent-Kaurenoic acid (KA) is a key intermediate connected to a phytohormone gibberellin. To date, the general procedure for quantifying KA is by using traditional gas chromatography–mass spectrometry (GC–MS). In contrast, gibberellins, which are more hydrophilic than KA, can be easily quantified by liquid chromatography-tandem mass spectrometry (LC–MS/MS). In this study, we have established a new method to quantify KA by LC–MS/MS by taking advantage of a key feature of KA, namely the lack of fragmentation that occurs in MS/MS when electrospray ionization (ESI) is in the negative mode. Q1 and Q3 were adopted as identical channels for the multiple reaction monitoring of KA. The method was validated by comparing with the results obtained by selected ion monitoring in GC–MS. This new method could be applicable for the quantification of other hydrophobic compounds.

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Section: Resultsmentioning

confidence: 99%

Analysis of ent-kaurenoic acid by ultra-performance liquid chromatography-tandem mass spectrometry

Miyazaki

Kimura

Natsume

et al. 2015

Biochemistry and Biophysics Reports

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“…Copaifera reticulata Ducke (Fabaceae), is a tree growing in the tropical regions of Latin America (Veiga Junior and Pinto, 2002;Costa et al, 2015). The oleoresins of C. reticulata and a few other Copaifera species, which are obtained by perforation of the trunks during the rainy season, are commonly referred to as copaiba oil and traditionally used as a panacea by the indigenous population (Ohsaki et al, 1994;Veiga Junior and Pinto, 2002;Boaroto, 2014).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and cytotoxic effects of the Copaifera reticulata oleoresin and its main diterpene acids

Barbosa

Wenzel‐Storjohann

Barbosa

et al. 2019

Journal of Ethnopharmacology

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Ethnopharmacological relevance: The oleoresin of Brazilian Copaifera reticulata is a traditional remedy used for the treatment of skin and urinary tract infections, respiratory diseases, rheumatism, ulcer and tumours; thus, playing an important role in the primary health care of the indigenous population. Aim: As most previous pharmacological tests used the crude oleoresin and only a few studies so far dealt with enriched fractions or pure chemically defined compounds, the aim of this study was to systematically evaluate the antimicrobial and cytotoxic properties of the Copaifera reticulata oleoresin and to assign traditional uses to specific secondary metabolites. Materials and methods: The oleoresin, as well as its neutral and acidic fractions were tested for their activity against six cancer cell lines, two clinically relevant bacterial strains, and two dermatophytes. Both fractions were analysed by GC-MS and UHPLC-ELSD, respectively. The antibacterial acidic phase was further fractionated by preparative chromatography to purify and characterize the compounds responsible for the observed pharmacological effect. Results: Whereas no cytotoxic activity was detected, the crude oleoresin and its acidic fraction showed antibacterial activity against gram-positive bacteria Enterococcus faecium (IC50 values 4.2 and 4.8 µg/mL, respectively) and methicillin-resistant Staphylococcus aureus (MRSA, IC50 values 5.3 and 7.2 µg/mL, respectively). Purification of the acidic fraction of the C. reticulata oleoresin yielded two dicarboxylic diterpene acids and the four main diterpene acids, comprising three different diterpene scaffolds. Interestingly, the activity was not restricted to a particular diterpene-type but rather depended on the compounds' lipophilicity, with the most active constituent showing IC50 values of 1.6 (E. faecium) and 2.5 µg/mL (MRSA), respectively. Furthermore, ent-polyalthic acid, the major diterpenoid, was significantly active 3 against dermatophytes with IC50 values of 6.8 µg/mL (Trichophyton rubrum) and 4.3 µg/mL against (T. mentagrophytes). Conclusion: The present study proved the antimicrobial effects of the C. reticulata oleoresin and its diterpenoid constituents, confirming its wide use in folk medicine for the treatment of skin and urinary tract infections. The inhibitory activity of copaiba diterpenoids against dermatophytic fungi as well as the gram-positive bacteria E. faecium and MRSA is being reported for the first time, providing potential lead structures for the treatment of these clinically relevant bacterial strains.

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“…The base peak chromatogram is shown in Figure 4 (positive ionization mode) and Figure 5 (negative ionization mode). The characterization of compounds was performed based on the mass spectrum obtained in MS-ESI and compared with the previous literature reports (Zehl et al, 2011 ; Costa et al, 2015 ; Wang et al, 2015 ). The results of the LC-MS analysis enabled tentative identification of 20 different compounds, as shown in Table 2 , with their retention time, molecular weight, monoisotropic mass, and molecular formula.…”

Section: Resultsmentioning

confidence: 99%

Molecular docking and pharmacokinetic prediction of phytochemicals from Syzygium cumini in interaction with penicillin-binding protein 2a and erythromycin ribosomal methylase of Staphylococcus aureus

Shidiki¹,

Vyas²

2022

bta

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Background MRSA and MLSB resistant S. aureus are known as important pathogens, which are responsible for many cases of both hospital and community-acquired infections worldwide. Studying drug discovery from plant sources is regarded as an important prevention strategy regarding these types of infections. Material and methods Agar well diffusion method was performed for antimicrobial evaluation, LCMS technique used for identification of different compounds, molecular docking performed by application of i GEMDOCK for PBP2a and ERM to plant compounds, and its pharmacokinetic evaluation of ADMET through use of AdmetSAR. Results Water extract was the most effective against resistant strains of Staphylococcus aureus . Twenty compounds belonging to phenols, flavonoids, organic acids, terpenoids groups were reported. Eighteen plant compounds passed in Lipinski's rule of five. i GEMDOCK revealed diferulic acid has the least binding energy –102.37 kcal/mole to penicillin-binding protein 2a and taxifolin has the least binding energy of –103.12 kcal/mole to erythromycin ribosomal methylase in comparison to control linezolid. These compounds raise the potential for developing potent inhibitors of penicillin-binding protein 2a and erythromycin ribosomal methylase for drug development. ADMET properties revealed that eighteen studied compounds were found in category III and IV with non-toxic properties except two butin and taxifolin found in category II with toxic properties. Conclusions It can be concluded that diferulic acid and taxifolin compounds provide the best inhibitor effect to PBP2a and ERM protein for inhibition of MRSA and MLSB resistant strains of S. aureus through the application of molecular docking, leading to a lead drug candidate for the treatment of diseases.

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Copaifera langsdorffii supercritical fluid extraction: Chemical and functional characterization by LC/MS and in vitro assays

Abstract: Freitas, L. A. P. de; Mendiola, J. A.; Ibáñez, Elena "Copaifera langsdorffii supercritical fluid extraction: Chemical and functional characterization by LC/MS and in vitro assays" Journal of Supercritical Fluids 100: 86-96 (2015)

Cited by 26 publications

References 49 publications

Analysis of ent-kaurenoic acid by ultra-performance liquid chromatography-tandem mass spectrometry

Analysis of ent-kaurenoic acid by ultra-performance liquid chromatography-tandem mass spectrometry

Antimicrobial and cytotoxic effects of the Copaifera reticulata oleoresin and its main diterpene acids

Molecular docking and pharmacokinetic prediction of phytochemicals from Syzygium cumini in interaction with penicillin-binding protein 2a and erythromycin ribosomal methylase of Staphylococcus aureus

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