Phytochemical analysis of the methanolic leaves extract of Niedenzuella multiglandulosa (Malpighiaceae), a plant species toxic to cattle in Brazil

Mannochio-Russo, Helena; Queiroz, Emerson Ferreira; Marcourt, Laurence; Rutz, Adriano; Allard, Pierre‐Marie; Almeida, Rafael Felipe de; Carvalho, Nilton M.; Wolfender, Jean‐Luc; Bolzani, Vanderlan da Silva

doi:10.1016/j.phytol.2020.02.005

Cited by 6 publications

(3 citation statements)

References 36 publications

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“…These compounds are mainly characterized by the presence of consecutive neutral losses of water molecules, in addition to the hydrocarbon side chain cleavage ( Lavrynenko et al, 2013 ; Mannochio-Russo et al, 2020 ). The presence of ecdysteroids in Niedenzuella multiglandulosa was recently described in the literature ( Mannochio Russo et al, 2020 ; Mannochio-Russo et al, 2020 ), being the only reports of this class of compounds in the Malpighiaceae family. Our results showed a wide diversity of ecdysteroids in all six Niedenzuella species sampled, being possible chemical markers for the Niedenzuella genus.…”

Section: Resultsmentioning

confidence: 98%

Untargeted Metabolomics Sheds Light on the Diversity of Major Classes of Secondary Metabolites in the Malpighiaceae Botanical Family

et al. 2022

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Natural products produced by plants are one of the most investigated natural sources, which substantially contributed to the development of the natural products field. Even though these compounds are widely explored, the literature still lacks comprehensive investigations aiming to explore the evolution of secondary metabolites produced by plants, especially if classical methodologies are employed. The development of sensitive hyphenated techniques and computational tools for data processing has enabled the study of large datasets, being valuable assets for chemosystematic studies. Here, we describe a strategy for chemotaxonomic investigations using the Malpighiaceae botanical family as a model. Our workflow was based on MS/MS untargeted metabolomics, spectral searches, and recently described in silico classification tools, which were mapped into the latest molecular phylogeny accepted for this family. The metabolomic analysis revealed that different ionization modes and extraction protocols significantly impacted the chemical profiles, influencing the chemotaxonomic results. Spectral searches within public databases revealed several clades or genera-specific molecular families, being potential chemical markers for these taxa, while the in silico classification tools were able to expand the Malpighiaceae chemical space. The classes putatively annotated were used for ancestral character reconstructions, which recovered several classes of metabolites as homoplasies (i.e., non-exclusive) or synapomorphies (i.e., exclusive) for all sampled clades and genera. Our workflow combines several approaches to perform a comprehensive evolutionary chemical study. We expect it to be used on further chemotaxonomic investigations to expand chemical knowledge and reveal biological insights for compounds classes in different biological groups.

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Section: Resultsmentioning

confidence: 98%

Untargeted Metabolomics Sheds Light on the Diversity of Major Classes of Secondary Metabolites in the Malpighiaceae Botanical Family

et al. 2022

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“…These classes of compounds are widely distributed in plant species, including the family Malpighiaceae. , Also, O -glycosylated flavonoids and caffeoylquinic acid derivatives have been described for other Heteropterys species, such as H. tomentosa , , H. brachiata , H. chrysophylla , and H. byrsonimifolia . However, the presence of C -glycosylated flavonoids in the Heteropterys genus has not been reported to date.…”

Section: Resultsmentioning

confidence: 99%

“…Even though several Malpighiaceae species with a meaningful chemical diversity have been reported, a significant percentage of this family has not been studied in depth regarding their specialized metabolites and biological activities. Several species in this family are known to possess toxic constituents, such as Banisteriopsis caapi , Tetrapterys mucronata , Niedenzuella multiglandulosa , and Amorimia species . Furthermore, a previous study conducted with extracts of the Asian endemic Hiptage benghalensis showed promising insecticidal and repellent activities against mosquito vectors from Southeast Asia (specifically Anopheles barbirostris , Culex quinquefasciatus , and Aedes albopictus ) .…”

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Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata

et al. 2023

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The Aedes aegypti (Diptera: Culicidae) mosquito is the vector of several arboviruses in tropical and subtropical areas of the globe, and synthetic pesticides remain the most widely used combat strategy. This study describes the investigation of secondary metabolites with larvicidal activity from the Malpighiaceae taxon using a metabolomic and bioactivity-based approach. The workflow initially consisted of a larvicidal screening of 394 extracts from the leaves of 197 Malpighiaceae samples, which were extracted using solvents of different polarity, leading to the selection of Heteropterys umbellata for the identification of active compounds. By employing untargeted mass spectrometry-based metabolomics and multivariate analyses (PCA and PLS-DA), it was possible to determine that the metabolic profiles of different plant organs and collection sites differed significantly. A bioguided approach led to the isolation of isochlorogenic acid A (1) and the nitropropanoyl glucosides karakin (2) and 1,2,3,6-tetrakis-O-[3-nitropropanoyl]-beta-glucopyranose (3). These nitro compounds exhibited larvicidal activity, possibly potentialized by synergistic effects of their isomers in chromatographic fractions. Additionally, targeted quantification of the isolated compounds in different extracts corroborated the untargeted results from the statistical analyses. These results support a metabolomic-guided approach in combination with classical phytochemical techniques to search for natural larvicidal compounds for arboviral vector control.

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Study of optical and morphological properties of nanoparticles semiconductors of zinc oxide synthesized using Mimosa tenuiflora extract for photodegradation of methyl orange

Luque

2022

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Phytochemical analysis of the methanolic leaves extract of Niedenzuella multiglandulosa (Malpighiaceae), a plant species toxic to cattle in Brazil

Cited by 6 publications

References 36 publications

Untargeted Metabolomics Sheds Light on the Diversity of Major Classes of Secondary Metabolites in the Malpighiaceae Botanical Family

Untargeted Metabolomics Sheds Light on the Diversity of Major Classes of Secondary Metabolites in the Malpighiaceae Botanical Family

Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata

Study of optical and morphological properties of nanoparticles semiconductors of zinc oxide synthesized using Mimosa tenuiflora extract for photodegradation of methyl orange

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