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The chemical ecology of plant-insect interactions has been driving our understanding of ecosystem evolution into a more comprehensive context. Chlosyne lacinia (Lepidoptera: Nymphalidae) is an olygophagous insect herbivore, which mainly uses host plants of Heliantheae tribe (Asteraceae). Herein, plant-insect interaction between Tithonia diversifolia (Heliantheae) and Chlosyne lacinia was investigated by means of untargeted LC-MS/MS based metabolomics and molecular networking, which aims to explore its inherent chemical diversity. C. lacinia larvae that were fed with T. diversifolia leaves developed until fifth instar and completed metamorphosis to the adult phase. Sesquiterpene lactones (STL), flavonoids, and lipid derivatives were putatively annotated in T. diversifolia (leaves and non-consumed abaxial surface) and C. lacinia (feces, larvae, pupae, butterflies, and eggs) samples. We found that several furanoheliangolide-type STL that were detected in T. diversifolia were ingested and excreted in their intact form by C. lacinia larvae. Hence, C. lacinia caterpillars may have, over the years, developed tolerance mechanisms for STL throughout effective barriers in their digestive canal. Flavonoid aglycones were mainly found in T. diversifolia samples, while their glycosides were mostly detected in C. lacinia feces, which indicated that the main mechanism for excreting the consumed flavonoids was through their glycosylation. Moreover, lysophospholipids were predominately found in C. lacinia samples, which suggested that they were essential metabolites during pupal and adult stages. These findings provide insights into the natural products diversity of this plant-insect interaction and contribute to uncovering its ecological roles.

Bees are essential pollinators on earth, supporting forest equilibrium and human agriculture. The chemistry of the stingless bee–plant symbiosis is a complex and not completely understood phenomenon. Here, we combined untargeted tandem mass spectrometry, molecular networking, and multivariate statistical analysis to investigate the chemical diversity in colonies of the stingless bee Scaptotrigona depilis. Flavonoids were the most representative and diverse group of plant metabolites detected, indicating the importance of these biologically active natural products to the bees. We unveiled the metabolome, mapped the distribution of plant metabolites in stingless bee colonies, and digitized the chemical data into a public database.

Balanced nutritional intake is essential to ensure that insects undergo adequate larval development and metamorphosis. Integrative multidisciplinary approaches have contributed valuable insights regarding the ecological and evolutionary outcomes of plant–insect interactions. To address the plant metabolites involved in the larval development of a specialist insect, we investigated the development of Chlosyne lacinia caterpillars fed on Heliantheae species (Tithonia diversifolia, Tridax procumbens and Aldama robusta) leaves and determined the chemical profile of plants and insects using a metabolomic approach. By means of LC-MS and GC-MS combined analyses, 51 metabolites were putatively identified in Heliantheae species and C. lacinia caterpillars and frass; these metabolites included flavonoids, sesquiterpene lactones, monoterpenoids, sesquiterpenoids, diterpenes, triterpenes, oxygenated terpene derivatives, steroids and lipid derivatives. The leading discriminant metabolites were diterpenes, which were detected only in A. robusta leaves and insects that were fed on this plant-based diet. Additionally, caterpillars fed on A. robusta leaves took longer to complete their development to the adult phase and exhibited a greater diapause rate. Hence, we hypothesized that diterpenes may be involved in the differential larval development. Our findings shed light on the plant metabolites that play roles in insect development and metabolism, opening new research avenues for integrative studies of insect nutritional ecology.

Vernonanthura polyanthes (Spreng.) A.J. Vega & Dematt. (syn.: Vernonia polyanthes Less) is popularly known as “assa-peixe” and its leaves are used in folk medicine mainly to treat respiratory diseases. In this study, we evaluated the cytogenotoxic and anticytogenotoxic potential of the V. polyanthes leaf aqueous extract (VpLAE) and its n-butanol fraction (n-BF) in the presence or absence of doxorubicin (DXR) (pre-, co-, and post-treatments) on a murine model for 24 h or 120 h. The micronucleus test (MN) and the comet assay were used to assess the cytogenotoxic and anticytogenotoxic potential of VpLAE and n-BF (250, 500, and 1000 mg/kg) administered via gavage to Swiss Webster mice. The chemical profiles of VpLAE and n-BF were assessed by liquid chromatography coupled to mass spectrometry, and their metabolites were putatively identified. Lastly, the possible biological activities related to the (anti) cytogenotoxicity of the compounds were predicted using the PASS online webserver. The in vivo results showed that different doses of VpLAE and n-BF did not present cytotoxic activity; however, the MN test revealed a slight mutagenic activity for the 24 h treatments. Moderate genotoxic effects were demonstrated for all treatments in the comet assay. Regarding anticytotoxicity and antimutagenicity, VpLAE and n-BF presented a high cytoprotective potential against DXR toxic effects. In the co-treatment, VpLAE reduced the DXR genotoxicity by ~27%, and n-BF did not demonstrate antigenotoxic potential. In contrast, an antigenotoxic effect was observed for both VpLAE and n-BF in the pre- and post-treatments, reducing DXR genotoxicity by ~41% and ~47%, respectively. Chemical analysis of VpLAE and n-BF showed the presence of eight phenolic compounds, including seven chlorogenic acids and a flavonoid. The PASS online tool predicted antimutagenic, anticancer, antineoplastic, chemoprotective, antioxidant, and radical scavenging activities for all constituents identified in VpLAE and n-BF. V. polyanthes leaves presented a protective effect against DXR cytogenotoxicity. In general, VpLAE and n-BF showed a greater antigenotoxic potential in the pre- and post-treatments. The metabolites putatively identified in VpLAE and n-BF exhibited antioxidant and chemoprotective potential according to computational prediction analysis. Altogether, our results highlight the potential application of V. polyanthes to protect against toxic manifestations induced by DXR.

RESUMO:A espécie vegetal Solanum lycocarpum, Solanaceae, popularmente conhecida como lobeira, está distribuída por todo o Brasil, principalmente em áreas do cerrado. Estudos comprovam que os frutos possuem diversas atividades e, atualmente, estão sendo utilizados no tratamento da diabetes. As folhas são utilizadas popularmente contra afecções das vias urinárias, cólicas abdominais e renais, espasmos e epilepsia, porém são poucos os estudos científicos que verificam as atividades farmacológicas das folhas. Assim, torna-se necessária a determinação de parâmetros anatômicos, físico-químicos e fitoquímicos que auxiliarão em futuras identificações e controle de qualidade da droga vegetal. Neste estudo foi realizada a coleta, secagem e pulverização das folhas de Solanum lycocarpum para a obtenção da droga vegetal e posterior caracterização desta. As análises microscópicas do pecíolo, nervura central e mesofilo revelaram características típicas da família Solanaceae, observando-se um sistema vascular bicolateral e a presença de areia cristalina e tricomas estrelados. A triagem fitoquímica, constatou a presença de taninos, flavonoides, esteróides e triterpenos, cumarinas e saponinas. Obteve-se o teor médio de 9,90% de perda por dessecação, 7,91% de cinzas totais e de 0,37% de cinzas insolúveis em ácidos. Para as substâncias extraíveis por álcool, o teor médio encontrado foi de 14,479% para o método de extração por Soxhlet e 0,987% para o método de extração a frio. Assim, espera-se que esses dados possam ser utilizados na identificação e controle de qualidade da droga vegetal de Solanum lycocarpum para a produção de novos medicamentos fitoterápicos.Palavras chave:Solanum lycocarpum, parâmetros analíticos, Solanaceae.ABSTRACT: Determination of the anatomics, physical-chemicals and phytochemicals parameters of the Solanum lycocarpum A.St.-Hill leaves. The plant species Solanum lycocarpum, Solanaceae, most known as lobeira, are distributed throughout Brazil, especially in Cerrado areas. Studies show that the fruits own different properties and, currently, are being used in the treatment of diabetes. Even though the leaves are being used by the general population against urinary tract disorders, renal and abdominal cramps, spasms and epilepsy, there are few scientific studies that verify the possible pharmacological activities of leaves. This shows that it is necessary to research and determinate the anatomic, physical-chemicals and the phytochemicals parameters that are going to help in the identification and quality assurance of the drug. In this study the leaves of Solanum lycocarpum were collected, dried and pulverized in order to be obtained the plant drug for further characterization.. Microscopic analyzes of the petiole, midrib and mesophyll showed typical features of the Solanaceae family, by detecting a biocolateral vascular system and the presence of crystallines and and stellatetrichomes. In the phytochemical screening performed, the tanning, flavonoids, sterols and triterpenes, coumarins and saponins were found. ...

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