Dereplication by HPLC-ESI-MS and antioxidant activity of phenolic compounds from Banisteriopsis laevifolia (Malpighiaceae)

Abstract

The genus Banisteriopsis (Malpighiaceae) comprises 77 genera and 1,300 species. Despite efforts to provide detailed information about the chemical wealth of B. laevifolia, this article provides the identification and characterization of compounds from the ethanolic extracts of the leaves and flowers using advanced methodologies which include high-performance liquid chromatography coupled to tandem mass spectrometry, which contribute to the knowledge about compounds present in the genus Banisteriopsis. The dereplication aided by Global Natural Products Social Molecular Networking afforded the identification of seven compounds reported for this species for the first time. A mixture of two known flavonoids and a diterpenoid, 18-hydroxy-ent-halima-1(10),13-(E)-dien-15-oic acid, were isolated by conventional separation methods. The elevated 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity observed in some samples was attributed to either the type of extract, the presence of 3,4,5-trihydroxybenzoic acid, or the influence of the substitution pattern and the synergistic effect of the compounds present. Principal Component Analysis was applied to correlate mass spectrometry data with the antioxidant activity of the samples. The high diversity of metabolites found in this study and those which have been reported for Banisteriopsis strongly recommends further investigation into the chemical and biological properties of these species.

Evidence of antagonism in vitro and in vivo of extracts from Banisteriopsis laevifolia (A. Juss) B. Gates against the rice blast fungus

“…However, searches for chemical constituents from EEL and EEF have provided a fresh perspective, demonstrating that the identified compounds are predominantly related to phenolic compounds. Previous studies have described polyphenols in leaves (Nunes et al, 2016), flowers (Alexandre et al, 2022), and roots (Freitas et al, 2015) of Banisteriopsis species.…”

“…Banisteriopsis laevifolia leaves and flowers were previously collected in Goiânia city, Goiás-Brazil and identified by Dr. Aristônio Magalhães Teles from the Universidade Federal de Goiás. According to the extraction procedure done by Alexandre et al (2022), the extracts of flowers (EEF) (49.7 g, 8.0%) and leaves (EEL) (79.2 g, 11.0%) were obtained.…”

“…The genus Banisteriopsis is part of the Malpighiaceae family and comprises 92 species that present pantropical distribution (Alexandre et al, 2022). Chemical and biological studies have focused on the potential of Banisteriopsis genus, revealing the presence of various classes of secondary metabolites, such as βcarboline alkaloids (Frias et al, 2012), flavonoids, anthraquinones (Freitas et al, 2015), phenanthrenes (Nunes et al, 2016) and diterpenoids (Alexandre et al, 2022).…”

“…Translation into English), for the treatment of ovarian haemorrhage and nephritis, as a topical antimycotic, and to avoid plagues in some crops (Freitas et al, 2015;Nunes et al, 2016). Research studies related to the biological potential of B. laevifolia have reported the antioxidant activity of extracts of leaves and flowers (Alexandre et al, 2022). In addition, the essential oil extracted from the leaves of B. laevifolia showed antifungal activity against yeasts of the genus Candida (Nunes et al, 2016) and antimicrobial potential related to some types of periodontitis, such as Fusobacterium nucleatum, Bacteroides thetaiotaomicron and Porphyronomas gingivalis (Nunes et al, 2016).…”

“…3,5,7trihydroxy-2-(4-hydroxyphenyl)-chromen-4-one; and 3′,4′,5,7tetrahydroxyflavone, as well as 2,3,7,8-tetrahydroxychromeno (5,4,3) chromene-5,10-dione, 4-hydroxycinnamic acid and 3,4,5trihydroxybenzoic acid have been described in the flower's extracts (Alexandre et al, 2022). Thus, due to the activity mentioned for B. laevifolia the analysis of the antagonism against M. oryzae contributes to evaluation of substances that have the potential to be used as eco-friendly control.…”