Carajurin: a anthocyanidin from Arrabidaea chica as a potential biological marker of antileishmanial activity

Silva-Silva, João Victor; Tellis, Carla Junqueira Moragas; Chagas, Maria S.S.; Souza, Paulo Victor Ramos de; Moreira, Davyson L.; Souza, C. S. F.; Teixeira, Kerolain Faoro; Cenci, Arthur Ribeiro; Oliveira, Aldo Sena de; Almeida-Souza, Fernando; Behrens, Maria Dutra; Calabrese, Kátia da Silva

doi:10.1016/j.biopha.2021.111910

Cited by 16 publications

(21 citation statements)

References 46 publications

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“…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 . However, the mechanism of action of carajurin on L. amazonensis has not been previously studied.…”

Section: Introductionsupporting

confidence: 63%

“…Moreover, we verified a superiority of carajurin among the other anthocyanidins in inhibiting Leishmania promastigotes, demonstrating the direct action of this natural compound on this parasite [ 12 ]. Data described in the previously published article [ 12 ], emphasize the inhibition of intracellular amastigote forms, indicating activation of leishmanicidal macrophage functions, especially the induction of NO. These results showed that carajurin can act indirectly by activation of mechanisms in macrophage, such as an increased release of NO.…”

Section: Discussionmentioning

confidence: 76%

“…The molecular formula C 17 H 15 O 5 was established by the positive mode quasi-molecular ion peaks at m/z 299.0905 for [M + H] + (calcd. 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 ].…”

Section: Resultsmentioning

confidence: 99%

“…Previous studies demonstrated a direct effect of A. chica against L. amazonensis and L. infatum promastigote forms [ 20 , 21 ]. Our research group reported that A. chica was able to inhibit the proliferation of promastigote forms of L. amazonensis [ 11 , 12 , 22 ]. Moreover, we verified a superiority of carajurin among the other anthocyanidins in inhibiting Leishmania promastigotes, demonstrating the direct action of this natural compound on this parasite [ 12 ].…”

Section: Discussionmentioning

confidence: 99%

“…Our research group reported that A. chica was able to inhibit the proliferation of promastigote forms of L. amazonensis [ 11 , 12 , 22 ]. Moreover, we verified a superiority of carajurin among the other anthocyanidins in inhibiting Leishmania promastigotes, demonstrating the direct action of this natural compound on this parasite [ 12 ]. Data described in the previously published article [ 12 ], emphasize the inhibition of intracellular amastigote forms, indicating activation of leishmanicidal macrophage functions, especially the induction of NO.…”

Section: Discussionmentioning

confidence: 99%

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

et al. 2022

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Carajurin is the main constituent of Arrabidaea chica species with reported anti-Leishmania activity. However, its mechanism of action has not been described. This study investigated the mechanisms of action of carajurin against promastigote forms of Leishmania amazonensis. Carajurin was effective against promastigotes with IC50 of 7.96 ± 1.23 μg.mL−1 (26.4 µM), and the cytotoxic concentration for peritoneal macrophages was 258.2 ± 1.20 μg.mL−1 (856.9 µM) after 24 h of treatment. Ultrastructural evaluation highlighted pronounced swelling of the kinetoplast with loss of electron-density in L. amazonensis promastigotes induced by carajurin treatment. It was observed that carajurin leads to a decrease in the mitochondrial membrane potential (p = 0.0286), an increase in reactive oxygen species production (p = 0.0286), and cell death by late apoptosis (p = 0.0095) in parasites. Pretreatment with the antioxidant NAC prevented ROS production and significantly reduced carajurin-induced cell death. The electrochemical and density functional theory (DFT) data contributed to support the molecular mechanism of action of carajurin associated with the ROS generation, for which it is possible to observe a correlation between the LUMO energy and the electroactivity of carajurin in the presence of molecular oxygen. All these results suggest that carajurin targets the mitochondria in L. amazonensis. In addition, when assessed for its drug-likeness, carajurin follows Lipinski’’s rule of five, and the Ghose, Veber, Egan, and Muegge criteria.

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Section: Introductionsupporting

confidence: 63%

Section: Discussionmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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

et al. 2022

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Friedericia Chica, a Medicinal Plant from the Amazon Region, is Repellent Against Aedes Aegypti: In Vivo and Molecular Docking Evidence

Miorando,

Cristina Maccagnan,

Dalla Vecchia

et al. 2024

Chemistry & Biodiversity

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Fridericia chica is widely distributed in Brazil, where it is commonly known as crajiru or pariri in several regions. Despite its popular use for treating inflammations and as an insect repellent, there has been limited assessment of its chemical and biological properties, including its bioinsecticide activities. In this study, we conducted phytochemical analyses and investigated the larvicidal and repellent effects of F. chica against the mosquito Aedes aegypti. The F. chica (HEFc) hydroalcoholic extract was partitioned using column chromatography, and subfractions were analyzed using chromatographic and spectroscopic analyses (ESI‐IT‐MSn and NMR). In addition, HEFc was evaluated for its larvicidal and repellent activities. Phytochemical analyses revealed the presence of 17 constituents, including 2,4‐dihydroxybenzoic and p‐coumaric acids, along with umbelliferone, acetovanilone, myricetin‐3‐O‐glucuronide, and cis‐isorhapontigenin, which are reported for the first time in this species. Although no larvicidal effect was observed at the doses tested, the HEFc exhibited promising repellent effects against A. aegypti, which aligns with its ethnopharmacological potential. In addition, molecular docking studies demonstrated that the compounds of HEFc interacted efficiently with insect odorant binding proteins (OBPs), providing repellent effects. Consistent with the chemical profile and in silico studies, preparations of F. chica have considerable repellent potential.

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Gastroprotective role of a flavonoid-rich subfraction from Fridericia chica (Bonpl.) L. G. Lohmann: a medicinal plant used in the Amazon region

Miorando,

Steffler,

Vecchia

et al. 2024

Inflammopharmacol

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Carajurin: a anthocyanidin from Arrabidaea chica as a potential biological marker of antileishmanial activity

Cited by 16 publications

References 46 publications

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

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

Friedericia Chica, a Medicinal Plant from the Amazon Region, is Repellent Against Aedes Aegypti: In Vivo and Molecular Docking Evidence

Gastroprotective role of a flavonoid-rich subfraction from Fridericia chica (Bonpl.) L. G. Lohmann: a medicinal plant used in the Amazon region

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