Ovicidal, pupicidal, adulticidal, and repellent activity of Helicteres velutina K. Schum against Aedes aegypti L. (Diptera: Culicidae).

Aedes aegypti is a vector of emerging and neglected diseases, such as dengue, chikungunya, and Zika. Helicteres velutina, known as "pitó" in Brazil, is traditionally used as an insect repellent, and several studies have demonstrated its larvicidal activity. The aim of this study was to investigate this species and evaluate its potential ovicidal, pupicidal, adulticidal, and repellent activity. The viability of the eggs was evaluated using different concentrations of the test substances for 25 days. The hexane fraction killed 72.7% of the eggs, while dichloromethane killed 67.7%. The survival of the pupae and adults was verified after 72 h and 48 h, respectively. The LC50 for the hexane and dichloromethane fractions was 0.12 mg/mL and 8.85 mg/mL for pupae, 8.01 mg/mL and 0.74 mg/mL for adults (tarsal test), and 0.05 mg/mL and 0.23 mg/mL for adults (body test), respectively. Repellency was assessed for 240 min using neonatal Wistar rats on a Y-tube olfactometer. The hexane fraction attracted mosquitoes to the test chamber, while the dichloromethane fraction had a repellent action. The 7,4'-di-O-methyl-8-O-sulfate flavone provides greater repellency, and this finding is similar to the results of the in silico studies that have shown the potential of this substance against adult mosquitoes. This suggests that 7,4'-di-O-methyl-8-O-sulfate flavone may be one of the substances present in the extract from aerial parts of H. velutina that is responsible for the repellent activity mentioned in traditional medicine. These findings provide a better understanding of the insecticidal and repellent activity of the extract, fraction, and compounds isolated from H. velutina against Ae. aegypti, thereby revealing its potential in the development of a more effective botanical insecticide.

Aedes aegypti é o vetor de doenças emergentes e negligenciadas, como dengue, chikungunya e Zika. Helicteres velutina, conhecida como 'pitó' no Brasil, é tradicionalmente usada como um repelente de insetos, estudos anteriores comprovaram sua atividade larvicida. O objetivo desta pesquisa foi investigar esta espécie, avaliando seu potencial ovicida, pupicida, adulticida e repelente. A viabilidade dos ovos foi avaliada utilizando diferentes concentrações das substâncias teste durante 25 dias, a fração hexano causou a inviabilização de 72,7% dos ovos, enquanto a diclorometano matou 67,7%. A sobrevivência de pupas e adultos foi verificada após 72 e 48 horas, respectivamente. A CL50 da fração hexano e diclorometano foi de 0,12 e 8,85 mg/mL para pupas; 8,0 e 0,74 mg/mL para adultos (teste tarsal); 0,05 e 0,23 mg/mL para adultos (teste corporal), respectivamente. A repelência foi avaliada durante 240 min utilizando neonatos de ratos Wistar em um olfatômetro de tubo Y. No teste de atração-repelência, a fração hexano atraiu mosquitos para camara teste, enquanto a fração diclorometano causou repelência. A 7,4'-di-O-metil-8-O-sulfato flavona proporcionol maior repelência, corroborando com estudos in silico que mostram potencial dessa substância em mosquitos adultos. Sugerindo que 7,4'-di-O-metil-8-O-sulfato flavona pode ser uma das substâncias presente no extrato das partes aéreas de H. velutina, responsável pela atividade repelente citada na medicina tradicional. Esses achados proporcionam uma melhor compreensão da atividade inseticida e repelente do extrato, fração e compostos isolados de H. velutina frente a Ae. aegypti mostrando potencial no desenvolvimento de um inseticida botânico mais eficaz.

Sidastrum paniculatum (L.) Fryxell (Malvaceae): A Promising Source of Bioactive Sulfated Flavonoids Against Aedes aegypti L.

Aedes aegypti L. is known as the most relevant vector mosquito for viruses such as yellow fever, chikungunya, dengue, and Zika, especially in places with unplanned urbanization, and erratic water supply. Plants used in folk medicine have become a useful source of active compounds with the potential to control the dissemination of Ae. aegypti. Compounds isolated from Malvaceae sensu lato have been previously reported as larvicides, repellents, and insecticides. Recent studies have demonstrated the anti Ae. aegypti activity of sulfated flavonoids, an uncommon type of flavonoid derivatives. This research reports the phytochemical investigation of Sidastrum paniculatum (L.) Fryxell, a Malvaceae species with the potential against Ae. aegypti. Chromatographic procedures resulted in the isolation of the compounds: stearic acid (1), N-trans-feruloyltyramine (2), acacetin (3), apigenin (4), tiliroside (5), along with the sulfated flavonoids: wissadulin (6), 7,4'-di-O-methyl-8-O-sulfate flavone (7), yannin (8), beltraonin (9a), 7-O-sulfate isoscutellarein (paniculatumin) (9b), and condadin (10). This is the first report of compound 7-O-sulfate isoscutellarein (9b). The structures were elucidated by spectroscopic analysis (NMR, LC-HRMS and FT-IR). The sulfated flavonoids identified were submitted to a ligand-based and structure-based virtual screening against two targets: 1YIY (from adult Ae. aegypti) and 1PZ4 (from Ae. aegypti larvae). The results indicated that when the O-sulfate group is bearing the position 7, the structures are potentially active in 1PZ4 protein. On the other hand, flavonoids with the O-sulfate group bearing position 8 were showed to be more likely to bind to the 1YIY protein. Our findings indicated that S. paniculatum is a promising source of sulfated flavonoids with potential against Ae. aegypti.

Intestinal anti-inflammatory activity of xique-xique (Pilosocereus gounellei A. Weber ex K. Schum. Bly. Ex Rowl) juice on acetic acid-induced colitis in rats.

Inflammatory bowel disease (IBD) is characterized by severe mucosal damage in the intestine and a deregulated immune response. Natural products derived from plants that are rich in bioactive compounds are used by many patients with IBD. Xique-xique (Pilosocereus gounellei) is a cactus of the Caatinga family that has been used by the local population for food and medicinal purposes. The intestinal anti-inflammatory effect of xique-xique cladode juice was evaluated in the present study. A dose of 5 mL kg-1 had a protective effect on intestinal inflammation, with an improvement in macroscopic damage, and a decrease in pro-inflammatory markers and oxidative stress, in addition to preserving the colonic tissue. Immunohistochemical analysis revealed the downregulation of IL-17, NF-κB, and iNOS, and upregulation of SOCs-1, ZO-1, and MUC-2. These protective effects could be attributed to the phenolic compounds as well as the fibers present in xique-xique juice. Further studies are needed before suggesting the use of xique-xique juice as a new alternative for treating IBD.

New Alcamide and Anti-oxidant Activity of Pilosocereus gounellei A. Weber ex K. Schum. Bly. ex Rowl. (Cactaceae).

The Cactaceae family is composed by 124 genera and about 1438 species. Pilosocereus gounellei, popularly known in Brazil as xique-xique, is used in folk medicine to treat prostate inflammation, gastrointestinal and urinary diseases. The pioneering phytochemical study of P. gounellei was performed using column chromatography and HPLC, resulting in the isolation of 10 substances: pinostrobin (1), ß-sitosterol (2), a mixture of sitosterol 3-O-ß-d-glucopyranoside/stigmasterol 3-O-ß-d-glucopyranoside (3a/3b), 13²-hydroxyphaeophytin a (4), phaeophytin a (5), a mixture of ß-sitosterol and stigmasterol (6a/6b), kaempferol (7), quercetin (8), 7'-ethoxy-trans-feruloyltyramine (mariannein, 9) and trans-feruloyl tyramine (10). Compound 9 is reported for the first time in the literature. The structural characterization of the compounds was performed by analyses of 1-D and 2-D NMR data. In addition, a phenolic and flavonol total content assay was carried out, and the anti-oxidant potential of P. gounellei was demonstrated.

New Sulphated Flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae).

Wissadula periplocifolia (L.) C. Presl (Malvaceae) is commonly used in Brazil to treat bee stings and as an antiseptic. The antioxidant properties of its extracts have been previously demonstrated, thus justifying a phytochemical investigation for its bioactive phenolic constituents. This has yielded five new sulphated flavonoids: 8-O-sulphate isoscutellarein (yannin) (1a); 4'-O-methyl-7-O-sulphate isoscutellarein (beltraonin) (1b); 7-O-sulphate acacetin (wissadulin) (2a); 4'-O-methyl-8-O-sulphate isoscutellarein (caicoine) (2b) and 3'-O-methyl-8-O-sulphate hypolaetin (pedroin) (3b) along with the known flavonoids 7,4'-di-O-methyl-8-O-sulphate isoscutellarein (4), acacetin, apigenin, isoscutellarein, 4'-O-methyl isoscutellarein, 7,4'-di-O-methylisoscutellarein, astragalin and tiliroside. The compounds were isolated by column chromatography and identified by NMR (¹H, (13)C, HMQC, HMBC and COSY) and LC-HRMS. A cell based assay was carried out to evaluate the preliminary cytotoxic properties of the flavonoids against UVW glioma and PC-3M prostate cancer cells as well as non-tumour cell lines. The obtained results showed that acacetin, tiliroside, a mixture of acacetin + apigenin and the sulphated flavonoids 2a + 2b exhibited inhibitory activity against at least one of the cell lines tested. Among the tested flavonoids acacetin and tiliroside showed lower IC50 values, presenting promising antitumor effects.

Nanostructured layer-by-layer films containing phaeophytin-b: electrochemical characterization for sensing purposes.

This paper reports the study and characterization of a new platform for practical applications, where the use of phaeophytin-b (phaeo-b), a compound derived from chlorophyll, was characterized and investigated for sensing purposes. Modified electrodes with nanostructured phaeo-b films were fabricated via the layer-by-layer (LbL) technique, where phaeo-b was assembled with cashew gum, a polysaccharide, or with poly(allylamine) hydrochloride (PAH). The multilayer formation was investigated with UV-Vis spectroscopy by monitoring the absorption band associated to phaeo-b at approximately 410 nm, where distinct molecular interactions between the materials were verified. The morphology of the films was analyzed by atomic force microscopy (AFM). The electrochemical properties through redox behavior of phaeo-b were studied with cyclic voltammetry. The produced films were applied as sensors for hydrogen peroxide (H2O2) detection. In terms of sensing, the cashew/phaeo-b film exhibited the most promising result, with a fast response and broad linear range upon the addition of H2O2. This approach provides a simple and inexpensive method for development of a nonenzymatic electrochemical sensor for H2O2.