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The species Trattinnickia rhoifolia Willd, (T. rhoifolia), which belongs to the Burseraceae family, is widely used in ethnopharmacological cultural practices by traditional Amazonian people for anti-inflammatory purposes, sometimes as their only therapeutic resource. Although it is used in teas, infusions, macerations and in food, the species is still unexplored in regard to its pharmacophoric potential and chemical profile. Therefore, the aim of this study was to conduct a phytochemical characterization of the hydroethanolic extract of T. rhoifolia leaves (HELTr) and to evaluate the acute toxicity and anti-inflammatory activity of this species using zebrafish (Danio rerio). The extract was analyzed by gas chromatography−mass spectrometry (GC-MS). The evaluation of the acute toxicity of the HELTr in adult zebrafish was determined using the limit test (2000 mg/kg), with behavioral and histopathological evaluations, in addition to the analysis of the anti-inflammatory potential of HELTr in carrageenan-induced abdominal edema, followed by the use of the computational method of molecular docking. The phytochemical profile of the species is chemically diverse, suggesting the presence of the fatty acids, ester, alcohol and benzoic acid classes, including propanoic acid, ethyl ester and hexadecanoic acid. In the studies of zebrafish performed according to the index of histopathological changes (IHC), the HELTr did not demonstrate toxicity in the behavioral and histopathological assessments, since the vital organs remained unchanged. Carrageenan-induced abdominal edema was significantly reduced at all HELTr doses (100, 200 and 500 mg/kg) in relation to the negative control, dimethyl sulfoxide (DMSO), while the 200 mg/kg dose showed significant anti-inflammatory activity in relation to the positive control (indomethacin). With these activities being confirmed by molecular docking studies, they showed a good profile for the inhibition of the enzyme Cyclooxygenase-2 (COX-2), as the interactions established at the sites of the receptors used in the docking study were similar to the controls (RCX, IMN and CEL). Therefore, the HELTr has an acceptable degree of safety for acute toxicity, defined in the analysis of behavioral changes, mortality and histopathology, with a significant anti-inflammatory action in zebrafish at all doses, which demonstrates the high pharmacophoric potential of the species. These results may direct future applications and drug development but still require further elucidation.

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Bursera comprises ~100 tropical shrub and tree species, with the center of the species diversification in Mexico. The genomic resources developed for the genus are scarce, and this has limited the study of the gene flow, local adaptation, and hybridization dynamics. In this study, based on ~155 million Illumina paired-end reads per species, we performed a de novo genome assembly and annotation of three Bursera species of the Bullockia section: Bursera bipinnata, Bursera cuneata, and Bursera palmeri. The total lengths of the genome assemblies were 253, 237, and 229 Mb for B. cuneata, B. palmeri, and B. bipinnata, respectively. The assembly of B. palmeri retrieved the most complete and single-copy BUSCOs (87.3%) relative to B. cuneata (86.5%) and B. bipinnata (76.6%). The ab initio gene prediction recognized between 21,000 and 32,000 protein-coding genes. Other genomic features, such as simple sequence repeats (SSRs), were also detected. Using the de novo genome assemblies as a reference, we identified single-nucleotide polymorphisms (SNPs) for a set of 43 Bursera individuals. Moreover, we mapped the filtered reads of each Bursera species against the chloroplast genomes of five Burseraceae species, obtaining consensus sequences ranging from 156 to 160 kb in length. Our work contributes to the generation of genomic resources for an important but understudied genus of tropical-dry-forest species.

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We investigated the structure, histochemistry, and ultrastructure of the secretory canals in the vegetative axis of Protium ovatum from a developmental perspective. Samples of roots, stems, and leaves were analyzed using light and transmission electron microscopy. Secretory canals composed of a uniseriate epithelium and a wide lumen occurred in the phloem of all analyzed organs. Schizogenesis and lysigenesis were merging processes involved in the origin, growth, ramification, and fusion of the secretory canals, forming an anastomosed secretory net. Essential oils, polysaccharides, and proteins were detected in the epithelial cells, as well as plastids with poorly developed thylakoids, dictyosomes, rough endoplasmic reticulum, polysomes, and oil drops, showing the mixed nature of the secretion. Epithelial cells exhibited pectin-cellulosic thickenings in the anticlinal and radial walls. These thickenings may act in directing the secretion flux toward the lumen, protecting the neighboring tissues from the toxicity of secreted metabolites. Structural irregularities observed in the mitochondria cristae in epithelial cells may be associated with processes induced by toxic substances. Epithelial cells protruded into the lumen and became lignified in the outer portion of the secondary phloem, obliterating the non-functional secretory canals. We propose that this phenomenon presents a physiological significance similar to that of tylose, preserving the secretion flow inside the active portions of the secretory system. To our knowledge, epithelial cells with wall thickenings, mitochondria with structural abnormalities, and obliteration of non-functional canals are features reported for the first time for Burseraceae. These features have important functional significance for Burseraceae secretory system and contribute to a deeper knowledge of P. ovatum, a medically and economically important plant.

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Objetivo: Avaliação histológica da influência da administração sistêmica de solução de Breu-branco, sob o reparo periodontal e pulpar de incisivos de ratos submetidos a reimplante dentário. Material e método: O composto testado foi obtido a partir do fracionamento da resina de P. heptaphyllum (Breu-branco) em coluna cromatográfica e diluído em solução de tween 80. A avulsão foi induzida no incisivo central superior direito de 33 ratos Wistar machos, divididos em três grupos: RI (Reimplante imediato), em que os dentes foram mantidos em meio seco e reimplantados com 5 minutos, RTLI (Reimplante tardio conservado em leite integral), dentes mantidos 60 minutos em leite integral, reimplantados e após os animais foram tratados por 5 dias com soro fisiológico por gavagem, e RTLI+BB (Reimplante tardio conservado em leite integral com administração de solução de breu-branco), os dentes permaneceram 60 minutos em leite integral, reimplantados e os animais foram tratados por 5 dias com breu-branco sistemicamente por gavagem. Após 60 dias foi realizada eutanásia por sobredosagem anestésica e coletada a hemi-maxila direita contendo o incisivo reimplantado. Os cortes histológicos transversais foram corados com hematoxilina-eosina para avaliação histológica em microscopia de luz. Na análise histomorfométrica foram analisadas as características do ligamento periodontal, osso alveolar, cemento, dentina e polpa. Os testes Kruskal-Wallis e post-hoc de Dunn foram utilizados para a comparação entre os grupos. Resultados: Os três grupos no geral apresentaram resultados semelhantes na maioria das variáveis analisadas, somente o grupo RTLI apresentou diferença estatística significativa menor na organização do ligamento periodontal e inflamação aguda em comparação com o grupo controle. Conclusão: A solução de breu-branco apresentou potencial para utilização como medicação sistêmica em casos de reimplante dentário tardio, por mostrar comportamento semelhante ao reimplante imediato no processo de reparo do ligamento periodontal e pulpar(AU)

Objective: Histological evaluation of the influence of systemic administration of Breubranco solution on periodontal and pulpal repair of incisors of rats submitted to dental reimplantation. Material and method: The compound tested was obtained from the fractionation of P. heptaphyllum resin (Breu-branco) in a chromatographic column and diluted in a tween 80 solution. The avulsion was induced in the upper right central incisor of 33 male Wistar rats, divided into three groups: IR (Immediate replantation), in which the teeth were kept in a dry medium and reimplanted after 5 minutes, RTLI (Delayed replantation preserved in whole milk), teeth kept 60 minutes in whole milk, reimplanted and after that the animals were treated for 5 days with saline solution by gavage, and RTLI+BB (Delayed replantation preserved in whole milk with administration of breu-branco solution), the teeth remained 60 minutes in whole milk, reimplanted and the animals were treated for 5 days with breu-branco systemically by gavage. After 60 days, euthanasia was performed by anesthetic overdose and the right hemi-maxilla containing the reimplanted incisor was collected. Cross-sectional histological sections were stained with hematoxylin-eosin for histological evaluation in light microscopy. In the histomorphometric analysis, the characteristics of the periodontal ligament, alveolar bone, cementum, dentin and pulp were analyzed. Kruskal-Wallis and Dunn's post-hoc tests were used for comparison between groups. Results: The three groups in general showed similar results in most of the variables analyzed, only the RTLI group showed a statistically significant lower difference in the organization of the periodontal ligament and acute inflammation compared to the control group. Conclusion: The breu-branco solution showed potential for use as a systemic medication in cases of late dental replantation, as it behaves similarly to immediate replantation in the repair process of the periodontal ligament and pulp(AU)

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Plant-derived products may represent promising strategies in the treatment of Neglected Tropical Diseases (NTDs). From this perspective, it is observed that the Amazon phytogeographic region contains the tribe Canarieae of the Burseraceae family, composed of trees and shrubs supplied with resin channels. Its uses in folk medicine are related to aromatic properties, which have numerous medicinal applications and are present in reports from traditional peoples, sometimes as the only therapeutic resource. Despite its economic and pharmacological importance in the region, and although the family is distributed in all tropical and subtropical regions of the world, most of the scientific information available is limited to Asian and African species. Therefore, the present work aimed to review the secondary metabolites with possible pharmacological potential of the species Trattinnickia rhoifolia Willd, popularly known as "Breu sucuruba". To this end, an identification key was created for chemical compounds with greater occurrence in the literature of the genus Trattinnickia. The most evident therapeutic activities in the consulted studies were antimicrobial, antioxidant, anti-inflammatory, antiviral, antifungal, anesthetic and antiparasitic. An expressive chemical and pharmacological relevance of the species was identified, although its potential is insufficiently explored, mainly in the face of the NTDs present in the Brazilian Amazon.

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The aim of this work was to prepare a nanoemulsion containing the essential oil of Protium heptaphyllum resin and to evaluate the larvicidal activity and the residual larvicidal effect against Aedes aegypti. The essential oil was identified by gas chromatography coupled to a mass spectrometer, and the nanoemulsions were prepared using a low-energy method and characterized by photon correlation spectroscopy. The results indicated the major constituents as p-cimene (27.70%) and α-Pinene (22.31%). Nanoemulsions had kinetic stability and a monomodal distribution in a hydrophilic-lipophilic balance of 14 with particle diameters of 115.56 ± 1.68 nn and zeta potential of -29.63 ± 3.46 mV. The nanoemulsion showed larvicidal action with LC50 = 2.91 µg∙mL-1 and residual larvicidal effect for 72 h after application to A. aegypti larvae. Consequently, the nanobiotechnological product derived from the essential oil of P. heptaphyllum resin could be used against infectious disease vectors.

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Abstract Essential oils, which may be extracted from several parts of plants, have different biological activities. The Brazilian Cerrado has a large variety of plants that yield essential oils, even though many have not been studied yet. Taking into account the biodiversity of this biome, this study aimed at evaluating the antiproliferative activity of essential oils extracted from three species of plants of the Cerrado in Goiás state: Campomanesia adamantium (Cambess.) O. Berg, Protium ovatum (Engl. in Mart.) and Cardiopetalum calophyllum (Schltdl.). Essential oils were extracted from both C. adamantium and C. calophyllum leaves and from P. ovatum leaves and green fruits by hydrodistillation carried out by a Clevenger-type apparatus. The chemical composition of the essential oils was determined by Gas Chromatography coupled to Mass Spectrometry (GC-MS). The following major chemical constituents were identified in the essential oils under investigation: β-myrcene (62.00%), spathulenol (28.78%), germacrene-B (18.27%), β-caryophyllene oxide (16.40%), β-caryophyllene (14.00%), α-pinene (11.30%), viridiflorol (9.99%), limonene (7.30%) and (Z,E)-pharnesol (6.51%). The antiproliferative activity was evaluated in different human tumor cell lines: breast adenocarcinoma (MCF-7), cervical adenocarcinoma (HeLa) and glioblastoma (M059J). A normal human cell line was included (GM07492A, lung fibroblasts). Results showed that essential oils from C. adamantium leaves got the lowest values of IC50 in all strains of tumor cells under evaluation. They were significantly lower than the ones of the normal cell line, an evidence of selectivity. It is worth mentioning that this is the first report of the antiproliferative activity of essential oils from C. adamantium , P. ovatum and C. calophyllum against human tumor cells.

Resumo Os óleos essenciais podem ser extraídos de várias partes das plantas e apresentam diversas atividades biológicas. O Cerrado brasileiro possui uma grande variedade de plantas produtoras de óleos essenciais muitas delas ainda não estudadas. Levando-se em consideração a biodiversidade desse bioma, o objetivo deste trabalho foi avaliar a atividade antiproliferativa dos óleos essenciais extraídos de três espécies de plantas ocorrentes no Cerrado do estado de Goiás: Campomanesia adamantium (Cambess.) O. Berg, Protium ovatum (Engl. in Mart.) e Cardiopetalum calophyllum (Schltdl.). Os óleos essenciais foram obtidos das folhas de C. adamantium e C. calophyllum e das folhas e frutos verdes de P. ovatum por hidrodestilação, usando o aparelho do tipo Clevenger. A composição química dos óleos essenciais foi determinada pelo método de Cromatografia Gasosa acoplada à Espectrometria de Massas (CG-EM). Os constituintes químicos majoritários identificados nos óleos essenciais estudados foram: β-mirceno (62,00%), espatulenol (28,78%), germacreno-B (18,27%), óxido de β-cariofileno (16,40%), β-cariofileno (14,00%), α-pineno (11,30%), viridiflorol (9,99%), limoneno (7,30%) e (Z,E)-farnesol (6,51%). A atividade antiproliferativa foi avaliada em diferentes linhagens de células tumorais humanas: adenocarcinoma de mama (MCF-7), adenocarcinoma cervical (HeLa) e gliobastoma (M059J), além de, uma linhagem celular humana normal (GM07492A, fibroblastos pulmonares). O óleo essencial das folhas de C. adamantium exibiu menores valores de CI50 em todas as linhagens celulares tumorais avaliadas, sendo menores que aquele obtido na linhagem celular normal, indicando seletividade. Este é o primeiro relato da atividade antiproliferativa dos óleos essenciais de C. adamantium , P. ovatum e C. calophyllum contra células tumorais humanas.

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ETHNOPHARMACOLOGICAL RELEVANCE: Leishmaniasis is a neglected disease that affects millions of people around the world. Parasite resistance and the toxicity to the current treatments lead to the search for new effective molecules. Plants are widely used in traditional and indigenous medicine to treat different diseases. The oleoresin of the genus Protium, which is rich in volatile compounds active against different microorganisms, is among these plants. AIM: The aim of this study was to evaluate the leishmanicidal potential of Protium altsonii (PaEO) and P. hebetatum (PhEO) (Burseraceae) oleoresins, as well as of three representative monoterpenes in their constitution: α-pinene, p-cymene and 1,8-cineole. MATERIALS AND METHODS: Protium altsonii (PaEO) and P. hebetatum (PhEO) oleoresins and three of their constituents were tested in vitro on promastigotes and amastigotes-infected macrophages in different concentrations. Their toxicity for macrophages was analyzed by XTT assay and phagocytic ability. It was evaluated the ability of the compounds to induce NO production on treated-macrophages using Griess reaction and the effect of them in lipid profile on treated-parasite through Thin Layer Chromatography. RESULTS: Our data showed that both essential oils have toxic effect on promastigotes and amastigotes of L. amazonensis in vitro in a dose-dependent manner. PaEO IC50 were 14.8 µg/mL and 7.8 µg/mL and PhEO IC50s were 0.46 µg/mL and 30.5 µg/m for promastigotes and amastigotes, respectively. Toxicity to macrophages was not observed at 50 µg/mL with both EOs. The compounds 1,8- cineole, α-pinene, and p-cymene inhibited amastigotes survival in a dose-dependent manner with IC50s of 48.4 µg/mL, 37 µg/mL, 46 µg/mL, respectively. Macrophage viability was around 90% even at 200 µg/mL and the phagocytic capacity was not altered in the treated-macrophages to up 50 µg/mL. The compounds were not able to modulate the nitric oxide production either at rest or LPS-activated macrophages. In addition, treated promastigote revealed an important change in their lipid profile after 48 h at 50 µg/mL in the presence of the compounds. CONCLUSIONS: The results indicate that oleoresins of Protium genus are potent against Leishmania and α-pinene, p-cymene and 1,8-cineole have anti-Leishmania properties that could be explored in synergistic assays in order to develop new drug candidates.

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The adaptive radiation of the angiosperms was strongly affected by fruit and seed dispersal since the establishment of the seedlings is a fundamental process for the recruitment of juveniles to the populations. Among the species of Burseraceae, seeds with fleshy attachments and high caloric value suggest mammaliochory as an ancestral dispersal way. In Protium icicariba, at the same time as there is a visual pattern typical of ornithochory, with a report of effective demonstration, the diaspores present the highest levels of essential oils of the whole plant, suggesting other dispersion processes by olfactory guided vectors. This work aims to monitor the diasporic dispersal process in P. icicariba in situ, aiming to identify dispersers and to investigate the role of the essential oil in the dispersion of diaspores of this plant species. The natural dispersion was monitored in situ, in weekly campaigns throughout eight months, using visual and photographic records, in daily shifts of six hours, distributed along the dawn, morning, afternoon, dusk, and night. We used both direct observation and continuous picture capturing along 43 days with photographic traps. Mature diaspores removed from pseudocapsules were pooled to determine potential dispersers. Artificial models of the diaspores, in white and green colors, were also used to test hypotheses on the role of scent in the dispersion, added 1%, weight/weight, of the essential oil extracted from the mature diaspores, which chemical composition determined by gas chromatography coupled to mass spectrometry. Besides, the analysis of stomach contents of lizards collected in adjacent area was also performed. In daytime and nighttime monitoring in nature, no vertebrates were recorded dispersing diaspores. The most common was the primary wind-facilitated autochory of diaspores to the substrate, near the plant matrices. Secondarily, workers of the ant species Atta robusta can remove the pseudoarils or move the pyrenes to the anthills. The lizard species Tropidurus torquatus ingests pyrenes with the pseudoarils, and the sclerified pericarp of the pyrene is potentially resistant to chemical action of the digestive juices. Ants and lizards have also accessed the caves with natural diaspores. Concerning the artificial diaspore models, ants accessed, indistinctly, white and the green models that contained essential oils. The lizards accessed the white models, with or without essential oils, and showed insignificant access to green ones, with or without essential oil. The ingestion of pyrenes by lizards was also confirmed through analysis of stomach contents. The aggregate spatial pattern of P. icicariba at the study site, associated with clumps, may be derived from germination in the substrate near the matrices, or in the anthills or after diaspora defecation and / or regurgitation of the lizard, which is a species strongly associated with clumps of this vegetation. As the access to the diaspores by ants and lizards depends on the primary autochory, and no impediments to the germination near to the matrix plant were found, the dispersion is compatible with a multifactorial characteristic of the diplochory.

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Essential oils, which may be extracted from several parts of plants, have different biological activities. The Brazilian Cerrado has a large variety of plants that yield essential oils, even though many have not been studied yet. Taking into account the biodiversity of this biome, this study aimed at evaluating the antiproliferative activity of essential oils extracted from three species of plants of the Cerrado in Goiás state: Campomanesia adamantium (Cambess.) O. Berg, Protium ovatum (Engl. in Mart.) and Cardiopetalum calophyllum (Schltdl.). Essential oils were extracted from both C. adamantium and C. calophyllum leaves and from P. ovatum leaves and green fruits by hydrodistillation carried out by a Clevenger-type apparatus. The chemical composition of the essential oils was determined by Gas Chromatography coupled to Mass Spectrometry (GC-MS). The following major chemical constituents were identified in the essential oils under investigation: ß-myrcene (62.00%), spathulenol (28.78%), germacrene-B (18.27%), ß-caryophyllene oxide (16.40%), ß-caryophyllene (14.00%), α-pinene (11.30%), viridiflorol (9.99%), limonene (7.30%) and (Z,E)-pharnesol (6.51%). The antiproliferative activity was evaluated in different human tumor cell lines: breast adenocarcinoma (MCF-7), cervical adenocarcinoma (HeLa) and glioblastoma (M059J). A normal human cell line was included (GM07492A, lung fibroblasts). Results showed that essential oils from C. adamantium leaves got the lowest values of IC50 in all strains of tumor cells under evaluation. They were significantly lower than the ones of the normal cell line, an evidence of selectivity. It is worth mentioning that this is the first report of the antiproliferative activity of essential oils from C. adamantium , P. ovatum and C. calophyllum against human tumor cells.

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