The Influence of Anthocyanidin Profile on Antileishmanial Activity of Arrabidaea chica Morphotypes

Abstract

Arrabidaea chica Verlot (crajiru) is a plant used in folk medicine as an astringent, anti-inflammatory, wound healing and to treat fungal and viral diseases such as measles chickenpox and herpes. Arrabidaea chica has several morphotypes recognized but little is known about its chemical variability. In the present study the anthocyanidin profile of A. chica morphotypes collected in two seasons (summer and winter) have been examined and their activity against Leishmania infection compared. High-performance liquid chromatography coupled to a diode-array detector (HPLC-DAD-UV) and by tandem mass spectrometry with electrospray ionization (ESI-MS/MS) were used for anthocyanidin separation and identification. Antileishmanial activity was measured against promastigote forms of Leishmania amazonensis. Multivariate analysis, principal component analysis (PCA) and Pearson’s correlation were performed to classify morphotypes accordingly to their anthocyanidin profile. The presence of 6,7,3′,4′-tetrahydroxy-5-methoxyflavylium (3′-hydroxy-carajurone) (1), carajurone (2), 6,7,3′-trihydroxy-5,4′-dimethoxy-flavylium (3′-hydroxy-carajurin) (3) and carajurin (4), and three unidentified anthocyanidins were detected. Two different groups were recognized: group I containing 3′-hydroxy-carajurone; and group II with high content of carajurin. Among anthocyanidins identified in the extracts, only carajurin showed significant statistical correlation (p = 0.030) with activity against L. amazonensis. Carajurin could thus be considered as a pharmacological marker for the antileishmanial potential of the species.

Carajurin Induces Apoptosis in Leishmania amazonensis Promastigotes through Reactive Oxygen Species Production and Mitochondrial Dysfunction

“…299.0924 for C 17 H 15 O 5 ) in combination with its NMR data as previously described [ 12 ]. Carajurin purity was previously determined by HPLC-DAD-UV as 98%, as well as by data from ESI-MS experiments and by NMR 1 H and 13 C data [ 11 ]. The compound was initially described by Chapman et al [ 13 ] and characterized by Zorn et al [ 14 ] and Devia et al [ 15 ].…”

“…B. Verlot, a plant popularly known as crajiru that is native to the Amazon rainforest [ 9 ], has been used in folk medicine for wound healing, treatment of inflammation, and antioxidant activities, possibly related to the presence of anthocyanidins [ 10 ]. Analyzing different morphotypes of A. chica , we observed that its hydro-alcoholic extract is rich in anthocyanidins, mainly carajurin [ 11 ]. We recently demonstrated, through the bioguided fractionation of A. chica extract, that carajurin favored its leishmanicidal activity [ 12 ], validating our earlier identification of carajurin as a pharmacological marker for the anti-leishmanial potential of A. chica .…”

Antileishmanial Activity of Flavones-Rich Fraction From Arrabidaea chica Verlot (Bignoniaceae)

“…Factors that can explain the difference in phytochemical and biological results are probably due to the climatic differences between the two locations where the plant was collected, as well as the way of obtaining the extract ( Cortez de Sá et al, 2015 ). However, it should be noted that the difference in cytotoxicity found with our study is probably related to the exposure time used, since we used 72 h, while in the study by Cortez de Sá et al (2015) the time was reduced to 24 h. Besides, and even more important, the different morphotypes of A. chica vary in chemical composition and, consequently, in biological activity ( Moragas-Tellis et al, 2020 ).…”

“…Publications by our research network previously reported on the leishmanicidal activity of hydroalcoholic extracts from four morphotypes of A. chica ( Moragas-Tellis et al, 2020 ). However, as the species A. chica exhibit a great set of polyphenolic compounds—mainly flavonoids—we decided to expand this study, previously done only with anthocyanidins, to evaluate whether flavones may also be involved in the leishmanicidal activity.…”

“…Furthermore, the infusion (oral use) is used to heal wounds and cleanse the blood (Bieski et al, 2012). Previous studies have demonstrated its antioxidant (do Amaral et al, 2012;dos Santos et al, 2013), wound healing (Aro et al, 2013;Cortez de Sá et al, 2015), trypanocidal (Barbosa et al, 2008;Miranda et al, 2017) and leishmanicidal activities (Rodrigues et al, 2014;Cortez de Sá et al, 2015;Moragas-Tellis et al, 2020). In the phytochemical screening of extracts of A. chica, the leaves are rich in anthocyanidins, such as carajurin and carajurone (Moragas-Tellis et al, 2020); in addition to some flavones (Paula et al, 2013), such as luteolin and apigenin (do Amaral et al, 2012).…”