Margaritaria nobilis L.F. (Phyllanthaceae): Ethnopharmacology and Application of Computational Tools in the Annotation of Bioactive Molecules

Abstract

Margaritaria nobilis is a shrubby species widely distributed in Brazil from the Amazon to the Atlantic Rainforest. Its bark and fruit are used in the Peruvian Amazon for disinfecting abscesses and as a tonic in pregnancy, respectively, and its leaves are used to treat cancer symptoms. From analyses via UHPLC-MS/MS, we sought to determine the chemical profile of the ethanolic extract of M. nobilis leaves by means of putative analyses supported by computational tools and spectral libraries. Thus, it was possible to annotate 44 compounds, of which 12 are phenolic acid derivatives, 16 are O-glycosylated flavonoids and 16 hydrolysable tannins. Among the flavonoids, although they are known, except for kaempferol, which has already been isolated from this species, the other flavonoids (10, 14, 15, 21, 24–26, 28–30, 33–35, 40 and 41) are being reported for the first time in the genus. Among the hydrolysable tannins, six ellagitannins present the HHDP group (6, 19, 22, 31, 38 and 43), one presents the DHHDP group (5), and four contain oxidatively modified congeners (12, 20, 37 and 39). Through the annotation of these compounds, we hope to contribute to the improved chemosystematics knowledge of the genus. Furthermore, supported by a metric review of the literature, we observed that many of the compounds reported here are congeners of authentically bioactive compounds. Thus, we believe that this work may help in understanding future pharmacological activities.

Margaritaria nobilis L.f. (Phyllanthaceae) Ethanolic Extract: Low Acute Oral Toxicity and Antinociceptive Activity

“…Such effects are probably related to its secondary metabolites identified by our group, such as flavonoids, hydrolyzed tannins, and phenolic acids. We described the annotation of 44 phytoconstituents ( Table 1 ) present in the MnE [ 7 ]. On this aspect, the metabolic annotation has expedited the clarification of the chemical-pharmacological signature of complex matrices, without ignoring the unequivocal identification that may allow bioactivity of greater magnitudes [ 14 ].…”

“…This tree is native to Brazilian territory and distributed in all of the region’s states, emphasizing the Amazon [ 6 ]. In traditional medicine, its bark is cited for treating abscesses, fruits as a tonic, and leaves for treating cancer-like symptoms [ 7 ].…”

“…There are few studies regarding the chemical constitution of M. nobilis , such as the study by Moraes et al [ 8 ], which addresses the phytochemical profile and leishmanicidal activity, and the study recently published with comprehensive characterization, indicating the presence of derivatives of phenolic acids, flavonoids, and hydrolyzable tannins [ 7 ]. In the genus Margaritaria , the presence of phenolic derivatives, glycosylated flavonoids ( M. discoidea ), and alkaloids ( M. indica ) has been described, together with their potential as antioxidant, antinociceptive, and anti-inflammatory agents [ 9 , 10 , 11 , 12 , 13 ].…”

The Roots of Deguelia nitidula as a Natural Antibacterial Source against Staphylococcus aureus Strains

“…Hence, bioactive extracts and fractions can have their molecular profile revealed in a few weeks or months by metabolite annotation (levels 2 and 3) [21], as established in previous reports by our research group [22][23][24]. In this approach here, we describe the chemical composition and in vitro antibacterial activity against S. aureus for the ethanolic extract and its fractions from the roots of D. nitidula.…”

Antibacterial Activity from Momordica charantia L. Leaves and Flavones Enriched Phase

“…This is a very effective strategy, especially because establishing a similarity relationship provides organization into molecular families (usually related chemical structures), and, therefore, finds related metabolites in the dataset even in small amounts. GNPS also contains a spectral library of known compounds, and the molecular networking allows automatic searches in the spectral library, which contributes to speed up the dereplication of known compounds, a phytochemical approach that has been widely used in recent decades, including the modest contribution of these authors [22][23][24][25][26], and which is also unknown by recognition of the analogs into the molecular families.…”