Comparison of the Qualitative Chemical Composition of Extracts from Ageratina havanensis Collected in Two Different Phenological Stages by FIA-ESI-IT-MSn and UPLC/ESI-MSn: Antiviral Activity

The flowers and leaves of Ageratina havanensis (Kunth) R. M. King & H. Robinson are traditionally used as a tea to cure several diseases. The production of active secondary metabolites can be affected by several environmental factors such as climate, altitude, rainfall, phenological stage and other conditions that may influence the growth of plants. In this sense, the development of a methodology to compare the chemical composition of plant extracts is needed. The qualitative chemical composition of the ethyl acetate extracts of flowers and leaves, collected in both reproductive and non-reproductive season, was determined by flow injection analysis-electrospray ionization-ion trap tandem mass spectrometry (FIA-ESI-IT-MSn) and ultra-high-performance liquid chromatography coupled to electrospray negative ionization mass spectrometry (UPLC/ESI-MSn). The qualitative chemical composition of the ethyl acetate extracts of flowers and leaves was very similar in all cases. Also the antiviral activity of flowers against human herpes simplex viruses type 1 and 2 (HSV-1, HSV-2) ( Herpesviridae) was analyzed. Three glucoside flavonoids were isolated from the ethyl acetate extract of the leaves of A. havanensis collected in flowering season using chromatographic methods and their structures were elucidated by physical and spectroscopic data measurements, and by comparing the obtained data with previously published values. The compounds were identified as 3- O-β-D-glucosyl-7-methoxyaromadendrin (5), 7- O-β-D-glucosyl-4′-dihydroxy-5-methoxyflavanone (6) and 5- O-β-D-glucosylsakuranetin (7); this is the first report of the isolation of these compounds in the Asteraceae family. Since the qualitative composition of the extracts of A. havanensis was similar in all cases, it can be expected that the ethyl acetate extract of the leaves collected in the non-reproductive season has anti-herpetic activity similar to that obtained in the reproductive season.

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Effects of different extracts of Cremastra appendiculata (D. Don) Makino Cremastra appendiculata (D. Don) Makino on apoptosis of A549 cells

Tropical Journal of Pharmaceutical Research ◽

10.4314/tjpr.v19i8.13 ◽

2020 ◽

Vol 19 (8) ◽

pp. 1653-1659

Author(s):

Haifeng Zhang ◽

Ziying Zhang ◽

Hua Du ◽

Xiaoli Su ◽

Xiaorong Li ◽

...

Keyword(s):

Flow Cytometry ◽

Ethyl Acetate ◽

Mtt Assay ◽

High Performance ◽

Ethyl Acetate Extract ◽

A549 Cells ◽

Butanol Extract ◽

Cremastra Appendiculata ◽

Ethyl Acetate Extracts

Purpose: To investigate the effect of different extracts of Cremastra appendiculata (D. Don) Makino onapoptosis of A549 cells, and the underlying mechanism.Methods: The contents of colchicine in ethyl acetate and n-butanol extracts of Cremastra appendiculata(D. Don) Makino were determined using high performance liquid chromatography (HPLC). Lung cancerA549 cells cultured in vitro were divided into blank control, standard colchicine and Cremastra appendiculata (D. Don) Makino extract groups. The effect of different extract concentrations on proliferation of the cells was determined using methyl thiazolyl diphenyl-tetrazolium (MTT) assay, while apoptosis of A549 cells induced by the extracts was evaluated by flow cytometry (FC).Results: Compared with the standard colchicine group, there was no colchicine in the n-butanol and ethyl acetate extracts of Cremastra appendiculata. Results from MTT assay showed that the extract inhibited the proliferation of A549 cells (p < 0.05). Flow cytometry results showed that ethyl acetate extract significantly enhanced apoptosis in A549 cells (p < 0.05). However, n-butanol extract had no significant effect on the apoptosis of A549 cells (p < 0.05).Conclusion: The ethyl acetate extract of Cremastra appendiculata (D. Don) Makino induces apoptosis in lung cancer A549 cells. Therefore, there is a need for further research and development of antitumor drugs from the extract of Cremastra appendiculata (D. Don) Makino. Keywords: Cremastra appendiculata (D. Don) Makino, Colchicine, A549 cells, Apoptosis

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Rapid qualitative profiling of metabolites present in Fusarium solani, a rhizospheric fungus derived from Senna spectabilis, using GC/MS and UPLC-QTOF/MSE techniques assisted by UNIFI information system

European Journal of Mass Spectrometry ◽

10.1177/1469066720922424 ◽

2020 ◽

Vol 26 (4) ◽

pp. 281-291

Author(s):

Natália Carolina Vieira ◽

Patrícia Cardoso Cortelo ◽

Ian Castro-Gamboa

Keyword(s):

Mass Spectrometry ◽

Liquid Chromatography ◽

Ethyl Acetate ◽

Fusarium Solani ◽

High Performance ◽

Ethyl Acetate Extract ◽

Bioactive Metabolites ◽

Flight Mass Spectrometry ◽

Wide Range

Fungi are an important source of natural products found in a variety of plant species. A wide range of methods for the detection of metabolites present in fungi have been reported in the literature. The search for methodologies that allow the rapid detection of compounds present in crude extracts is crucial to enable the metabolite annotation doing a qualitative analysis of the complex matrix. Mass spectrometry is an important ally when it comes to in silico detection of previously reported metabolites. In this work, the ethyl acetate extract of Fusarium solani was analyzed by gas chromatography coupled to mass spectrometry (GC/MS) after derivatization process. The ethyl acetate extract was also investigated by liquid chromatography coupled with high-resolution tandem mass spectrometry assisted by the UNIFI software system. A library containing previously reported metabolites from the Fusarium genus was added to the UNIFI platform. Simultaneously, the extract was analyzed through anticholinesterase and antifungal assays. The analysis of the derivatized extract by GC/MS led to the putative identification of five metabolites, and the investigation using Ultra-High Performance Liquid Chromatography - Quadrupole Time-of-Flight Mass Spectrometry (UPLC-QTOF) analysis in data-independent acquisition mode (mass spectrometry) led to the annotation of 15 compounds present in the built-in Fusarium library added to the UNIFI system. The Fusarium solani extract showed potential anticholinesterase and in vitro antifungal activity supported by the detection of bioactive metabolites.

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The chemical composition of the floral extract of Epipogium aphyllum sw. (Orchidaceae): A clue for their pollination biology

Archives of Biological Sciences ◽

10.2298/abs1403989b ◽

2014 ◽

Vol 66 (3) ◽

pp. 989-998 ◽

Cited By ~ 6

Author(s):

Anna Jakubska-Busse ◽

Izabela Jasicka-Misiak ◽

Anna Poliwoda ◽

Emilia Święczkowska ◽

Paweł Kafarski

Keyword(s):

Mass Spectrometry ◽

Chemical Composition ◽

High Performance ◽

Floral Scent ◽

Pollination Biology ◽

Ionization Mass ◽

Methyl Cinnamate ◽

Esi Ms ◽

Array Detection ◽

Pollination Systems

Epipogium aphyllum is a rare European obligate mycoheterotrophic orchid lacking chlorophyll. It has not been studied previously with respect to pollination biology. We studied the association between the composition of floral scent emission and its pollination systems. Field observation indicates that the main pollinators of Epipogium aphyllum are representatives of the genus Bombus (Hymenoptera), B. lucorum, B. hortorum, B. terrestris, B. pascuorum and B. proteus, and the genus Apis (Hymenoptera) namely A. mellifera. The main potential vector (observed to accidentally carry pollen), is most likely Episyrphus balteatus (Diptera, Syrphidae). The chemical composition of the floral extracts of 4 populations of Epipogium aphyllum Sw. growing naturally in Poland and the Czech Republic was examined by gas chromatography coupled with mass spectrometry (GC-MS) and high-performance liquid chromatography coupled with diode-array detection and electrospray ionization mass spectrometry (LC-ESI-MS) techniques. According to GC-MS analysis, 9-tricosene, nonadecane, 1-nonadecene and nonacosane predominated in the floral extracts. The studied samples were also characterized by relatively high amounts of benzenoids, e.g. methyl cinnamate, which is known as an attractant to the males of various orchid bees. LC-ESI-MS revealed the presence of flavor compounds such as vanillin (4-hydroxy-3-methoxybenzaldehyde) and its derivative acetovanillone, together with higher amounts of aliphatic and phenolic acids. Additionally, we detected the presence of indole and morphine derivatives.

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Chemical Constituents and Cytotoxic Activity of Rhinella jimi (Anura: Bufonidae)

Journal of the Brazilian Chemical Society ◽

10.21577/0103-5053.20210009 ◽

2021 ◽

Author(s):

Evaldo Monção Filho ◽

Yara Pio ◽

Mariana Chaves ◽

Paulo Ferreira ◽

Mariluce Fonseca ◽

...

Keyword(s):

Mass Spectrometry ◽

Liquid Chromatography ◽

Ethyl Acetate ◽

Cytotoxic Activity ◽

High Performance ◽

Atmospheric Pressure Chemical Ionization ◽

Chemical Constituents ◽

Ionization Mass ◽

Direct Infusion ◽

Isolation And Identification

Rhinella jimi toads (Stevaux, 2002) belong to the Bufonidae family, are endemic in the Brazilian Northeast and are commonly found during rainy periods. In general, amphibians of this family have in their poisons different metabolites that show a diversity of pharmacological activities. The isolation and identification of these compounds are of great importance, and techniques such as high-performance liquid chromatography coupled to mass spectrometry are widely used for the discovery of novel and known compounds in these poisons. For R. jimi poison, the ethyl acetate and methanolic extracts were obtained and thirty compounds were identified by combining ultra-performance liquid chromatography coupled to mass spectrometry (UPLC-MS) with direct infusion atmospheric pressure chemical ionization mass spectrometry (DI-APCI-MS/MS) and direct infusion electrospray mass spectrometry (DI-ESI-MS/MS) for each extract, respectively. Marinobufagin (2) and marinobufotoxin (19) were the majorities of each extract, respectively. In addition, other bufadienolides mainly present in the ethyl acetate extract, such other bufotoxins, alkaloids and arginine diacid derivatives were identified in the methanol extract. In a cytotoxic assay by 3-(4,5-dimethylthiazol-2-yl)-2,5‑diphenyltetrazolium bromide (MTT), the extracts and compound 2 demonstrated half-maximal inhibitory concentration (IC50) values better than the positive control doxorubicin, evidencing excellent cytotoxic. This is the most complete study of the chemical composition of R. jimi toad poison and its respective cytotoxic activity, promoting the enrichment of knowledge about this family and species.

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