Residual Larvicidal Activity of Quinones against Aedes aegypti

Silva, Raquel L.; Demarque, Daniel P.; Dusi, Renata G.; Sousa, João Paulo Barreto de; Albernaz, Lorena Carneiro; Espindola, Laïla Salmen

doi:10.3390/molecules25173978

Cited by 28 publications

(31 citation statements)

References 31 publications

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“…Compound 3 was identified using traditional techniques and vibrational circular dichroism (VCD). Compounds 1, 2, 3 and the benzoquinones: raponone (4), suberonone (5) and embelin (6), previously isolated by our group [12], were tested against L. infantum and L. amazonensis promastigotes and L. amazonensis amastigotes. Compounds 2 and 3 presented an IC 50 33.8 μM and 11.4 μM for L. amazonensis; and 44.3 μM and 13.3 μM for L. infantum, promastigotes respectively.…”

Section: Resultsmentioning

confidence: 99%

“…These two pterocarpans were identified by comparing NMR and HRESIMS data with the literature [21][22][23]. In a previous study, our research group isolated three benzoquinones from the C. suberosus root wood ethyl acetate extract, also investigated herein: rapanone (4), embelin (5) and suberonone (6) [12] (Fig 3).…”

Section: Plos Onementioning

confidence: 94%

“…In addition, cytotoxicity tests were also conducted in murine peritoneal macrophages (Table 3 and S2 Table). 1and leiocarpin (2), isolated due to the simple fraction chromatographic profiles; connarin (3), the ion pinpointed by metabolomics as important for activity, not found in the SciFinder database; and the quinones: rapanone (4), embelin (5) and suberonone (6) previously isolated by our group [12].…”

Section: Prolonged Antileishmanial Activity Exposure Of Extracts and mentioning

confidence: 99%

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Antileishmanial compounds from Connarus suberosus: Metabolomics, isolation and mechanism of action

et al. 2020

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Leishmaniasis is a disease impacting public health worldwide due to its high incidence, morbidity and mortality. Available treatments are costly, lengthy and toxic, not to mention the problem of parasite resistance. The development of alternative treatments is warranted and natural products demonstrate promising activity. This study investigated the activity of Connarus suberosus extracts and compounds against Leishmania species. Several C. suberosus extracts were tested against L. amazonensis promastigotes. Active and inactive extracts were analyzed by UHPLC-MS and data evaluated using a metabolomics platform, revealing an unknown neoflavonoid (connarin, 3), isolated together with the pterocarpans: hemileiocarpin (1) and leiocarpin (2). The aforementioned compounds (1–3), together with the benzoquinones: rapanone (4), embelin (5) and suberonone (6) previously isolated by our group from the same species, were tested against: (i) L. amazonensis and L. infantum promastigotes, and (ii) L. amazonensis intracellular amastigotes, with the most active compound (3) also tested against L. infantum amastigotes. Cytotoxicity against murine peritoneal macrophages was also investigated. Compounds 2 and 3 presented an IC50 33.8 μM and 11.4 μM for L. amazonensis promastigotes; and 44.3 μM and 13.3 μM for L. infantum promastigotes, respectively. For L. amazonensis amastigotes, the IC50 of 2 was 20.4 μM with a selectivity index (SI) of 5.7, while the IC50 of 3 was 2.9 μM with an SI of 6.3. For L. infantum amastigotes, the IC50 of 3 was 7.7 μM. Compounds 2 and 3 presented activity comparable with the miltefosine positive control, with compound 3 found to be 2–4 times more active than the positive control, depending on the Leishmania species and form. The extracts and isolated compounds showed moderate toxicity against macrophages. Compounds 2 and 3 altered the mitochondrial membrane potential (ΔΨm) and neutral lipid body accumulation, while 2 also impacted plasma membrane permeabilization, culminating in cellular disorder and parasite death. Transmission electron microscopy of L. amazonensis promastigotes treated with compound 3 confirmed the presence of lipid bodies. Leiocarpin (2) and connarin (3) demonstrated antileishmanial activity. This study provides knowledge of natural products with antileishmanial activity, paving the way for prototype development to fight this neglected tropical disease.

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Section: Resultsmentioning

confidence: 99%

Section: Plos Onementioning

confidence: 94%

Section: Prolonged Antileishmanial Activity Exposure Of Extracts and mentioning

confidence: 99%

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Antileishmanial compounds from Connarus suberosus: Metabolomics, isolation and mechanism of action

et al. 2020

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“…aegypti larvae in 3 mL de‐chlorinated water. Samples previously were solubilized in dimethyl sulfoxide (DMSO) and added to the wells in a fixed volume of 50 μL 25 . The same volume of DMSO (< 1.0% in tap water) was used as the negative control.…”

Section: Methodsmentioning

confidence: 99%

Machaerium acutifolium compounds with larvicidal activity against Aedes aegypti

Melo

Sousa

Sá

et al. 2020

Pest Management Science

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BACKGROUND Plant extracts and isolated compounds are known for their insecticidal activity. The Aedes aegypti mosquito has a significant medical impact as it transmits a number of arboviruses and is able to develop resistance to the commercially available insecticides. This study investigates larvicidal compounds isolated from Machaerium acutifolium, designated by the Brazilian Forest Service as a sustainable species. RESULTS A M. acutifolium trunk ethyl acetate extract was fractionated using chromatographic methods with full structural elucidation by mass spectrometry (MS), nuclear magnetic resonance and specific rotation analyses revealing: one new 3‐arylcoumarin derivative 1; two flavonoids 2 and 3; a trans‐stilbene 4, and an unprecedented natural indene 5. The larvicidal activity against Ae. aegypti after 24 h exposure was: crude extract (median lethal dose, LC50 205 mg L–1), fraction C (LC50 27 mg L–1) and 5 (LC50 24 mg L–1). CONCLUSION A M. acutifolium extract showed larvicidal activity, which increased with prolonged exposure, demonstrating LC50 75 mg L–1 after 72 h. Although the flavonoids 2 and 3 and trans‐stilbene 4 were deemed inactive according to the adopted mortality limit, additional tests revealed their ability to cause 65% Ae. aegypti larvae mortality, suggesting they could contribute to the larvicidal activity. Compound 5, identified by liquid chromatography‐MS, was over eight‐fold more toxic to larvae than the crude extract after 24 h. Therefore, 5 constitutes a structural model for new prototypes to control Ae. aegypti. These data reinforce the potential of natural products as a source of commercial alternatives for vector control strategies, respecting both sustainability and eco‐friendly principles. © 2020 Society of Chemical Industry

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“…A different problem was investigated by Silva et al [18]. The authors looked for the effective compounds against mosquito Aedes aegypti, which is the vector for arboviral diseases (dengue, Zika, yellow fever, and chikungunya).…”

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confidence: 99%