Screening for antifungal, DNA-damaging and anticholinesterasic activities of Brazilian plants from the Atlantic Rainforest: Ilha do Cardoso State Park

Lopes, Elaine Cristina; Carreira, Rosana Cristina; Agripino, Debora G.; Torres, Luce Maria Brandão; Cordeiro, Inês; Bolzani, Vanderlan da Silva; Dietrich, Sonia Machado de Campos; Young, Maria Cláudia Marx

doi:10.1590/s0102-695x2008000500002

Cited by 16 publications

(6 citation statements)

References 24 publications

(23 reference statements)

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“…Six Chrysobalanaceae plant species were collected in different regions from São Paulo State, Brazil, during development of the NuBBE extracts library, as part of the interdisciplinary BIOTA/SP program (FAPESP No. 2003/02176-7). , Vouchers were deposited at the “Herbarium Maria Eneyda P. K. Fidalgo”, Instituto Botânico de São Paulo, São Paulo, Brazil. Table S-1 depicts the plant species, their collection locations, and the voucher codes.…”

Section: Experimental Methodsmentioning

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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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: Experimental Methodsmentioning

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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“…The investigation of the aporphine alkaloids in complex biological samples was performed using two plant species from the NuBBE bank of extracts (details in Table ) . The extracts were prepared using an accelerated solvent extractor (ASE 300, Dionex Ltd, Oakville, ON, Canada) .…”

Section: Methodsmentioning

confidence: 99%

Characterization of aporphine alkaloids by electrospray ionization tandem mass spectrometry and density functional theory calculations

Neto

Andréo

Raftery

et al. 2019

Rapid Comm Mass Spectrometry

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Rationale Aporphine alkaloids represent a large group of isoquinoline natural products with important roles in biological and biomedical areas. Their characterization by electrospray ionization tandem mass spectrometry (ESI‐MS/MS) can contribute to their rapid identification in complex biological matrices. Methods We report the fragmentation of protonated 7,7‐dimethylaporphine alkaloids by ESI‐MS/MS, and the putative annotation of aporphine alkaloids in plant extracts. We used low‐ and high‐resolution MS/MS analyses to rationalize the fragmentation pathways, and employed the B3LYP/6‐31 + G(d,p) density functional theory (DFT) model to provide thermochemical parameters and to obtain the reactive sites. Results DFT calculations of a set of 7,7‐dimethylaporphine alkaloids suggested the heterocyclic amino group as the most basic site due to the proton affinity of the nitrogen atom. Collision‐induced dissociation experiments promoted •OCH3 elimination instead of the expected neutral loss of the heterocyclic amino group, pointing to the [M − 15 + H]•+ ion as the diagnostic fragment for 7,7‐dimethylaporphine alkaloids. The analysis of plant extracts led to the annotation of 25 aporphine alkaloids. Their fragmentation initiated with the loss of the amino group followed by formation of a cyclic carbocation. Further reactions derived from consecutive charge‐remote and/or charge‐induced fragmentations of the substituents attached to the aromatic system. The mechanisms were re‐examined based on plausible gas‐phase ion chemistry reactions. Conclusions Taken together, the diagnostic product ions and the series of radical and neutral eliminations provided information about the location of methylenedioxy, aromatic methoxy, and vicinal methoxy and hydroxy groups in aporphine alkaloids, assisting their characterization via MS/MS.

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“…One explanation for the differences in the amount of disease present in each forest species may be related to the production of secondary metabolites and the anatomy of their leaves. In Platymisicium species, the presence of flavonoids, isoflavonoids and other compounds with antifungal and cytotoxic properties has been reported (Cardoso-Lopes et al, 2008;Cuellar et al, 2020), although plant metabolites produced by E. cyclocarpum may also have antifungal activity (Pacheco et al, 2012;Biabiany et al, 2013). Arambarri et al (2006) observed the presence of conspicuous epicuticular waxes in Enterolobium spp., a common feature of species adapted to dry environments, which can confer resistance to penetrating pathogens.…”

Section: Incidence and Severity Of Foliar Anthracnose And Their Relationship With Tree Defoliationmentioning

confidence: 99%

“…In a survey of pathogens in the urban trees of Santa Marta, Colombia, Colletotrichum spp. were associated with foliar diseases in E. cyclocarpum and P. pinnatum (Cantillo, 2014). The symptoms associated with Colletotrichum in E. cyclocarpum consist of whitish rounded spots at the leaflet base on the leaf underside, while in P. pinnatum, the symptom corresponds to a light or dark brown anthracnose surrounded by a chlorotic halo (Cantillo, 2014;Restrepo-Leal and Rada-González, 2017).…”

mentioning

confidence: 99%

“…were associated with foliar diseases in E. cyclocarpum and P. pinnatum (Cantillo, 2014). The symptoms associated with Colletotrichum in E. cyclocarpum consist of whitish rounded spots at the leaflet base on the leaf underside, while in P. pinnatum, the symptom corresponds to a light or dark brown anthracnose surrounded by a chlorotic halo (Cantillo, 2014;Restrepo-Leal and Rada-González, 2017). Furthermore, in previous tests, the fungal pathogenicity was verified in both developing and mature foliar tissues of these forest species with the expression of characteristic symptoms in each plant (Restrepo-Leal and Rada-González, 2017).…”

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confidence: 99%

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Epidemiological study of Colletotrichum spp. associated with Enterolobium cyclocarpum (Jacq.) Griseb. and Platymiscium pinnatum (Jacq.) Dugand in the Colombian Caribbean Region

Leal

Gonzalez

Páez-Redondo

2022

Rev. Fac. Nac. Agron. Medellín

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Epidemiological analyzes of foliar diseases associated with Colletotrichum spp. in Enterolobium cyclocarpum and Platymiscium pinnatum were performed under field conditions and without any type of intervention. At the Universidad del Magdalena (Santa Marta, Colombia), four trees for each species and four equidistant monitoring sites per tree were established. The incidence and severity were recorded for 33 weeks (March to November 2016), including two follow-up periods: dry and rainy season. Disease development curves were elaborated. Moreover, the development rate (r) and the area under the disease progress curve (AUDPC) were calculated for each follow-up period. The effect of the meteorological variables was statistically analyzed by correlation and multiple regression. In E. cyclocarpum, the highest incidence and severity were recorded between September and November with 100 and 19.6%, respectively, showing a positive correlation with relative humidity and negative with average temperature, solar radiation and wind speed. In P. pinnatum, the maximum values of incidence and severity were observed between March and April with 68.9 and 1.3%, respectively. However, correlation analyzes did not support their relationship with the environmental factors. The r values during the dry months were 0.136 and 0.107 units week-1 and the AUDPCs were calculated at 51 and 4 units week-1 for E. cyclocarpum and P. pinnatum, respectively. In the rainy months, the r values were 0.187 and 0.016 units week-1 and the AUDPCs were 186 and 2 units week-1, respectively. In conclusion, the development of the disease varies according to the forest species, time of year and some meteorological variables.

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Screening for antifungal, DNA-damaging and anticholinesterasic activities of Brazilian plants from the Atlantic Rainforest: Ilha do Cardoso State Park

Cited by 16 publications

References 24 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

Characterization of aporphine alkaloids by electrospray ionization tandem mass spectrometry and density functional theory calculations

Epidemiological study of Colletotrichum spp. associated with Enterolobium cyclocarpum (Jacq.) Griseb. and Platymiscium pinnatum (Jacq.) Dugand in the Colombian Caribbean Region

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