Chrysobalanaceae: secondary metabolites, ethnopharmacology and pharmacological potential

Neto, Fausto Carnevale; Pilon, Alan César; Bolzani, Vanderlan da Silva; Castro‐Gamboa, Ian

doi:10.1007/s11101-012-9259-z

Cited by 17 publications

(13 citation statements)

References 53 publications

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“…The systematic investigation of all nodes based on the interpretation of the fragmentation patterns in the gas phase, in conjunction with previous studies for flavonoid identification via MS 2 , attests to the potential of MN as a tool to explore the chemical diversity of structurally related molecules and to unravel their complexity. According to the literature, more than 50 flavonoids have been described, so far, from Chrysobalanaceae plant species, with a predominance of flavonol glycosides . On the basis of the inspection of all MN nodes related to the flavonoid, 64 metabolites were putatively annotated in the Chrysobalanaceae plant species, which mostly were flavonol 3- O -glycosides.…”

Section: Discussionmentioning

confidence: 99%

“…In this study, we propose the incorporation of multiple fragmentation rules and chemotaxonomy in spectral similarity networks (MS/MS data) for the assignment of glycoconjugated flavonoids present in six plant species of the family Chrysobalanaceae, known by the high distribution and diversity of flavonoids . This strategy was built on characterizing how product ion values, abundances, and ratios guide the structural organization of the spectral network, with the goal of uncovering the identities of structurally related compounds, as illustrated in Scheme .…”

Section: Introductionmentioning

confidence: 99%

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Mass Spectral Similarity Networking and Gas-Phase Fragmentation Reactions in the Structural Analysis of Flavonoid Glycoconjugates

Pilon

Raftery

et al. 2019

Anal. Chem.

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Flavonoids represent an important class of natural products with a central role in plant physiology and human health. Their accurate annotation using untargeted mass spectrometry analysis still relies on differentiating similar chemical scaffolds through spectral matching to reference library spectra. In this work, we combined molecular network analysis with rules for fragment reactions and chemotaxonomy to enhance the annotation of similar flavonoid glyconjugates. Molecular network topology progressively propagated the flavonoid chemical functionalization according to collision-induced dissociation (CID) reactions, as the following chemical attributes: aglycone nature, saccharide type and number, and presence of methoxy substituents. This structure-based distribution across the spectral networks revealed the chemical composition of flavonoids across intra- and interspecies and guided the putatively assignment of 64 isomers and isobars in the Chrysobalanaceae plant species, most of which are not accurately annotated by automated untargeted MS2 matching. These proof of concept results demonstrate how molecular networking progressively grouped structurally related molecules according to their product ion scans, abundances, and ratios. The approach can be extrapolated to other classes of metabolites sharing similar structures and diagnostic fragments from tandem mass spectrometry.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mass Spectral Similarity Networking and Gas-Phase Fragmentation Reactions in the Structural Analysis of Flavonoid Glycoconjugates

Pilon

Raftery

et al. 2019

Anal. Chem.

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“…Chemotaxonomically, flavonoids, steroids and terpenes are the major constituents of the plant family (Carnevale Neto et al, 2013). The ease of availability of this plant in Nigeria and elsewhere prompted us to conduct antisnake venom activity and phytochemical analysis of the stem bark of N. macrophylla in which stigmasterol and bis-(5,7-diacetyl-catechin-4'-αrhamnopyranoside) were isolated (Yusuf et al, 2015a;Yusuf et al, 2015b).…”

Section: Introductionmentioning

confidence: 99%

Antisnake venom activity and isolation of quercetin from the leaf of Neocarya macrophylla (Sabine) Prance ex F. White (Malpighiales: Chrysobalanaceae)

Yusuf¹,

Abdullahi²,

Musa³

et al. 2019

Braz. J. Biol. Sci.

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Snake envenomation is a major cause of death and disability in many developing countries. Neocarya macrophylla (Sabine) Prance ex F. White (Malpighiales: Chrysobalanaceae) have been reportedly used in traditional medicine to treat snake envenomation. Bioassay-guided isolation of antivenom principles was carried out on the leaf of N. macrophylla against Naja nigricollis venom. The methanol extract of N. macrophylla leaf and its ethylacetate and n-butanol fraction significantly (P < 0.05) protected mice against venom-induced lethality with 100% survival rate and there was remarkable inhibition of the poisonous effects of PLA2 enzyme by the extracts and the fractions. Encouraged by this result, the ethylacetate soluble fraction was subjected to purification using vacuum liquid chromatography and gel filtration which led to the isolation of quercetin as the bioactive principle. The identity of the compound was determined on the basis of chemical tests, and by comparison of its 1H-NMR data with literature, this is the first report of isolation of this compound from the leaf of the plant. However, the results of the study suggests that the leaf of N. macrophylla possess significant antisnake venom activity which provide the scientific basis for its use in traditional treatment of snakebites.

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“…The proposed method is initiated with the optimization of AMDIS deconvolution parameters using a fractional design of experiments, followed by the application of RAMSY as a “digital filter” for the AMDIS metabolite identification process. Solanaceae, Chrysobalanaceae, and Euphorbiaceae plant species were selected as model systems to evaluate the new metabolite identification process due to their ethnopharmacological potential and economical value (Sharma and Singh, 2012 ; Carnevale Neto et al, 2013 ; Funari et al, 2013 ; Zappi et al, 2015 ).…”

Section: Introductionmentioning

confidence: 99%

Dereplication of Natural Products Using GC-TOF Mass Spectrometry: Improved Metabolite Identification by Spectral Deconvolution Ratio Analysis

Neto

Pilon

Selegato

et al. 2016

Front. Mol. Biosci.

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Dereplication based on hyphenated techniques has been extensively applied in plant metabolomics, thereby avoiding re-isolation of known natural products. However, due to the complex nature of biological samples and their large concentration range, dereplication requires the use of chemometric tools to comprehensively extract information from the acquired data. In this work we developed a reliable GC-MS-based method for the identification of non-targeted plant metabolites by combining the Ratio Analysis of Mass Spectrometry deconvolution tool (RAMSY) with Automated Mass Spectral Deconvolution and Identification System software (AMDIS). Plants species from Solanaceae, Chrysobalanaceae and Euphorbiaceae were selected as model systems due to their molecular diversity, ethnopharmacological potential, and economical value. The samples were analyzed by GC-MS after methoximation and silylation reactions. Dereplication was initiated with the use of a factorial design of experiments to determine the best AMDIS configuration for each sample, considering linear retention indices and mass spectral data. A heuristic factor (CDF, compound detection factor) was developed and applied to the AMDIS results in order to decrease the false-positive rates. Despite the enhancement in deconvolution and peak identification, the empirical AMDIS method was not able to fully deconvolute all GC-peaks, leading to low MF values and/or missing metabolites. RAMSY was applied as a complementary deconvolution method to AMDIS to peaks exhibiting substantial overlap, resulting in recovery of low-intensity co-eluted ions. The results from this combination of optimized AMDIS with RAMSY attested to the ability of this approach as an improved dereplication method for complex biological samples such as plant extracts.

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Chrysobalanaceae: secondary metabolites, ethnopharmacology and pharmacological potential

Cited by 17 publications

References 53 publications

Mass Spectral Similarity Networking and Gas-Phase Fragmentation Reactions in the Structural Analysis of Flavonoid Glycoconjugates

Mass Spectral Similarity Networking and Gas-Phase Fragmentation Reactions in the Structural Analysis of Flavonoid Glycoconjugates

Antisnake venom activity and isolation of quercetin from the leaf of Neocarya macrophylla (Sabine) Prance ex F. White (Malpighiales: Chrysobalanaceae)

Dereplication of Natural Products Using GC-TOF Mass Spectrometry: Improved Metabolite Identification by Spectral Deconvolution Ratio Analysis

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