Profiles of phenolic compounds by FT-ICR MS and antioxidative and antiproliferative activities of Stryphnodendron obovatum Benth leaf extracts

Costa, M. F. da; Galaverna, Renan; Pudenzi, Marcos A.; Ruiz, A. L. T. G.; Carvalho, João Ernesto de; Eberlin, Marcos N.; Santos, Catarina dos

doi:10.1039/c6ay01272h

Cited by 13 publications

(8 citation statements)

References 39 publications

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“…Therefore, the antiproliferative effect ( Table 4 ) observed for the three Myrcia species had negative correlation with the DPPH scavenger ability. These findings are on agreement with other results, showing that highly antioxidant flavonoids did not inhibit cell proliferation or polyphenolic enriched extracts [ 11 ]. Therefore, even without significant antiproliferative activity, antioxidant phytochemicals seem be useful for controlling oxidative stress in the microenvironment.…”

Section: Resultssupporting

confidence: 94%

“…The MS/MS experiment shows fragments of m / z 173 and 111, which correspond to the loss of the water molecule and a retro Diels-Alder (RDA) ring opening mechanism [ 10 ], respectively. Quinic acid has already been found in other plants of the genus Myrtaceae [ 11 ].…”

Section: Resultsmentioning

confidence: 99%

“…The deprotonated ion molecule of m / z 483 was assigned to digalloylglucose, since it provided the typical MS/MS fragment ions of m / z 331 [M − H − 152] − and m / z 169 [M − H − 162] − ( Scheme 1 ) [ 15 ]. Ellagic acid, galloyl-glucose and HHDP-glucose isomers are described in other Myrtaceae species, such as Eugenia punicifolia and E. aurata [ 11 ].…”

Section: Resultsmentioning

confidence: 99%

“…Before (T0) and after (T1) sample application, cells were fixed with 50% trichloroacetic acid (Merck) and cell proliferation was determined by the spectrophotometric quantification (540 nm) of cellular protein content using sulforhodamine B assay. Using the concentration–response curve for each cell line, the values of the sample concentration required to produce total growth inhibition or cytostatic effect (TGI) were determined through non-linear regression analysis using software ORIGIN 8.6 ® (OriginLab Corporation, Northamptom, MA, USA) [ 1 , 11 ].…”

Section: Methodsmentioning

confidence: 99%

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Antioxidative, Antiproliferative and Antimicrobial Activities of Phenolic Compounds from Three Myrcia Species

et al. 2018

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Myrcia bella Cambess., Myrcia fallax (Rich.) DC. and Myrcia guianensis (Aubl.) DC. (Myrtaceae) are trees found in Brazilian Cerrado. They have been widely used in folk medicine for the treatment of gastrointestinal disorders, hemorrhagic and infectious diseases. Few reports have been found in the literature connecting their phenolic composition and biological activities. In this regard, we have profiled the main phenolic constituents of Myrcia spp. leaves extracts by ESI(−)Q-TOF-MS. The main constituents found were ellagic acid (M. bella), galloyl glucose isomers (M. guianensis) and hexahydroxydiphenic (HHDP) acid derivatives (M. fallax). In addition, quercetin and myricetin derivatives were also found in all Myrcia spp. extracts. The most promising antioxidant activity, measured by 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity, was found for M. fallax extracts (EC50 8.61 ± 0.22 µg·mL−1), being slightly less active than quercetin and gallic acid (EC50 2.96 ± 0.17 and 2.03 ± 0.02 µg·mL−1, respectively). For in vitro antiproliferative activity, M. guianensis showed good activity against leukemia (K562 TGI = 7.45 µg·mL−1). The best antimicrobial activity was observed for M. bella and M. fallax to Escherichia coli (300 and 250 µg·mL−1, respectively). In conclusion, the activities found are closely related to the phenolic composition of these plants.

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Section: Resultssupporting

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Antioxidative, Antiproliferative and Antimicrobial Activities of Phenolic Compounds from Three Myrcia Species

et al. 2018

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“…The isotopic fine structure obtained from FT-ICR MS can also be used to determine the elemental formula (Shi et al 1998;Nakabayashi et al 2013). da Costa and coworkers showed the direct infusion electrospray ionization (ESI) FT-ICR mass spectrometry-based evaluation of phenolic compounds in plant leaves (da Costa et al 2016). Gardana and colleagues also used UPLC/MS/MS and high-resolution FT-ICR MS systems to reliably detect propolis allergens in raw propolis materials and commercial formulations (Gardana and Simonetti 2011).…”

Section: Introductionmentioning

confidence: 99%

UPLC/FT-ICR MS-based high-resolution platform for determining the geographical origins of raw propolis samples

Kim

Lee

et al. 2019

J Anal Sci Technol

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In this study, we demonstrate a high-resolution 15 Tesla Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometry coupled with a reverse-phase ultra-performance liquid chromatography (RP-UPLC) system for determining the geographical origins of raw propolis samples. The UPLC/FT-ICR MS-based high-resolution platform was validated on the ethanol-extracted propolis (EEP) from various propolis raw materials originating from different countries (i.e., Argentina, Brazil, China, and Korea) to determine the geographical origins of the propolis and the origin-specific key compounds. Based on approximately 8000 molecular features extracted from UPLC/FT-ICR MS datasets, a partial least squares-discriminant analysis (PLS-DA) plot showed distinct separations among propolis samples from four different origins. Key propolis components contributing to the discrimination of Korean propolis from Brazilian and Chinese propolis were identified and classified into five subgroups (i.e., flavonoids, phenols, terpenoids, fatty acids, and others). This analysis revealed the characteristic features of the different propolis samples, and this analytical platform can be further used to determine the geographical origins and to assess the quality of the commercial products.

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Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSⁿ and HRESIMS

Dantas

Abreu

Cunha

et al. 2021

Phytochemical Analysis

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Introduction: Given the diversity of secondary metabolites produced by species of the genus Erythroxylum, in addition to the many methods that have already been described in the literature, modern screening and identification methodologies, such as dereplication, represent an efficient and quick strategy compared to the classic techniques linked to natural product research. Objective: The objective of the present study was to determine the phenolic profiles obtained from three species of Erythroxylum (Erythroxylum pauferrense Plowman, Erythroxylum pulchrum A.St.-Hil. and Erythroxylum simonis Plowman) by dereplication using liquid chromatography coupled with ESI-MS n and HRESIMS. Material and Methods: Ethyl acetate and n-butanolic fractions from crude ethanolic extract of Erythroxylum species were analyzed by HPLC-ESI-MS n and HPLC-HRESIMS, in order to identify its corresponding compounds. Experiments were performed in negative ionization mode, and the metabolites were provisionally identified based on deprotonated molecules, molecular formulas, fragmentation patterns and literature data. The corresponding isolated compounds were characterized by 1 H and 13 C NMR spectroscopy.Results: According to the dereplication method, it was possible to establish and compare the phenolic profile of the corresponding species by the assignment of 55 compounds, most of which were first described in these species and among which some were also new to the Erytroxylum genus. Additionally, nine compounds were isolated, including biphenyl-3,3 0 ,4,4 0 -tetraol, where the mass spectral data were not sufficient for their identification, and reported for the first time in the Erythroxylaceae family. Conclusion: This research contributes to the phytochemical knowledge of theErythroxylum genus and demonstrates the importance of the dereplication method regarding the investigation of natural products, enabling accurate identification of the metabolites while avoiding the efforts and material expenses involved in the isolation of known compounds.

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Profiles of phenolic compounds by FT-ICR MS and antioxidative and antiproliferative activities of Stryphnodendron obovatum Benth leaf extracts

Abstract: The main phenolic constituents of S. obovatum leaf extracts, analyzed by FT-ICR MS, were correlated with their antioxidant and in vitro antiproliferative activities.

Cited by 13 publications

References 39 publications

Antioxidative, Antiproliferative and Antimicrobial Activities of Phenolic Compounds from Three Myrcia Species

Antioxidative, Antiproliferative and Antimicrobial Activities of Phenolic Compounds from Three Myrcia Species

UPLC/FT-ICR MS-based high-resolution platform for determining the geographical origins of raw propolis samples

Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSⁿ and HRESIMS

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Profiles of phenolic compounds by FT-ICR MS and antioxidative and antiproliferative activities of Stryphnodendron obovatum Benth leaf extracts

Abstract: The main phenolic constituents of S. obovatum leaf extracts, analyzed by FT-ICR MS, were correlated with their antioxidant and in vitro antiproliferative activities.

Cited by 13 publications

References 39 publications

Antioxidative, Antiproliferative and Antimicrobial Activities of Phenolic Compounds from Three Myrcia Species

Antioxidative, Antiproliferative and Antimicrobial Activities of Phenolic Compounds from Three Myrcia Species

UPLC/FT-ICR MS-based high-resolution platform for determining the geographical origins of raw propolis samples

Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSn and HRESIMS

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Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSⁿ and HRESIMS