Your browser doesn't support javascript.
loading
Mostrar: 20 | 50 | 100
Resultados 1 - 20 de 1.384
Filtrar
1.
Braz. j. biol ; 83: e236649, 2023. tab
Artigo em Inglês | LILACS, VETINDEX | ID: biblio-1339379

RESUMO

Abstract Croton argyrophylloides Muell. Arg., from the Euphorbiaceae family, popularly known as marmeleiro prateado or sacatinga, is a plant from the Caatinga biome commonly found in Brazil's northeastern region. The present study aimed to evaluate the antioxidant activity of the species. The phytochemical study was performed through qualitative analysis of chemical constituents and quantitative determination of the total phenol content through the Folin-Ciocalteu test. The qualitative and quantitative antioxidant tests were performed using the DPPH method (2.2 diphenyl-1-picryl hydrazil) and ferric reducing antioxidant power (FRAP). The minimum inhibitory concentration (MIC) was determined by microdilution in 96-well plates. The ethanolic extract of the leaves of C. argyrophylloides manifested antioxidant action in the quantitative DPPH test with a significant bioactivity of 84.70 AAO% in 500 µg/mL, with an EC50 of 236.79. The content of total phenolic compounds was 946.06 mg of gallic acid equivalents/g of sample, and total flavonoids was 58.11 mg of quercetin equivalents/g of sample, the result obtained for FRAP was 15294.44 µM Trolox/g of sample and ABTS was 718 μM Trolox of sample. The prospecting of the chemical constituents of the leaves of C. argyrophylloides revealed the presence of the main compounds that manifests the antioxidant activity and it was proven by the DPPH method that there is antioxidant activity in the analyzed sample, in addition to demonstrating a significant content of phenolic compounds and total flavonoid content in the species, which corroborates the antioxidant activity of the plant sample. The leaf extracts presented growth inhibition halos of 10 and 12 mm upon Staphylococcus aureus ATCC 25923.


Resumo Croton argyrophylloides Muell. Arg., pertencente à família Euphorbiaceae, conhecida popularmente como marmeleiro prateado e sacatinga, é um vegetal do bioma caatinga comumente encontrado no Nordeste do Brasil. O presente trabalho teve como objetivo avaliar a atividade antioxidante da espécie. O estudo fitoquímico foi realizado por meio de análise qualitativa dos constituintes químicos e determinação quantitativa do teor de fenóis totais pelo teste de Folin-Ciocalteu. Os testes antioxidantes qualitativos e quantitativos foram realizados pelo método do DPPH (2,2 difenil-1- picril-hidrazila) e redução do ferro (FRAP). A concentração inibitória mínima (CIM) foi determinada por microdiluição em placas de 96 poços. O extrato etanólico das folhas de C. argyrophylloides apresentou ação antioxidante no teste DPPH quantitativo com uma significativa bioatividade de 84.70 AAO% em 500 µg/mL, apresentando um CE50 de 236.79. O teor de compostos fenólicos totais, foi de 946,06 mg equivalentes de ácido gálico/g de amostra, e de flavonoides totais de 58,11 mg equivalentes de quercetina/g da amostra, o valor encontrado para FRAP foi de 15294,44 µM Trolox/g da amostra e de ABTS foi 718 μM Trolox da amostra. A prospecção dos constituintes químicos das folhas de C. argyrophylloides revelou a presença dos principais compostos que caracterizam a atividade antioxidante e foi possível comprovar pelo método de DPPH que há atividade antioxidante na amostra analisada, além de demonstrar um resultado significativo de teor de compostos fenólicos e teor de flavonoides totais na espécie e o que corrobora com a atividade antioxidante da amostra vegetal. Os extratos das folhas apresentaram halos de inibição de crescimento de 10 e 12mm frente a Staphylococcus aureus ATCC 25923.


Assuntos
Euphorbiaceae , Croton , Extratos Vegetais/farmacologia , Compostos Fitoquímicos , Antibacterianos/farmacologia , Antioxidantes/farmacologia
2.
Chem Biodivers ; 20(1): e202200777, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-36541751

RESUMO

In this study, the chemical composition of the essential oil (EO) extracted from Croton blanchetianus Baill leaves was identified, and antimicrobial and antibiofilm activities against Staphylococcus aureus, Staphylococcus epidermidis, and Escherichia coli strains were determined. Moreover, the effects of EO in combination with ampicillin and tetracycline were investigated. Thirty-four components, mainly mono-and sesquiterpenes that represented 94.05 % of the chemical composition, were identified in the EO. The EO showed bacteriostatic and bactericidal activities against all strains tested. Furthermore, the EO showed a synergistic effect with ampicillin and tetracycline. EO significantly inhibited biofilm formation and reduced the number of viable cells in biofilms. The EO may be a promising natural product for preventing bacterial biofilm infections.


Assuntos
Anti-Infecciosos , Croton , Euphorbiaceae , Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Antibacterianos/farmacologia , Antibacterianos/química , Ampicilina/farmacologia , Staphylococcus aureus , Tetraciclinas/farmacologia , Biofilmes , Testes de Sensibilidade Microbiana
3.
Molecules ; 27(24)2022 Dec 12.
Artigo em Inglês | MEDLINE | ID: mdl-36557952

RESUMO

Medicinal plants are known as sources of potential antimicrobial compounds belonging to different classes. The aim of the present work was to evaluate the antimicrobial potential of the crude extract, fractions, and some isolated secondary metabolites from the leaves of Macaranga occidentalis, a Cameroonian medicinal plant traditionally used for the treatment of microbial infections. Repeated column chromatography of the ethyl acetate and n-butanol fractions led to the isolation of seventeen previously known compounds (1-17), among which three steroids (1-3), one triterpene (4), four flavonoids (5-8), two stilbenoids (9 and 10) four ellagic acid derivatives (11-14), one geraniinic acid derivative (15), one coumarine (16), and one glyceride (17). Their structures were elucidated mainly by means of extensive spectroscopic and spectrometric (1D and 2D NMR and, MS) analysis and comparison with the published data. The crude extract, fractions, and isolated compounds were all screened for their antimicrobial activity. None of the natural compounds was active against Candida strains. However, the crude extract, fractions, and compounds showed varying levels of antibacterial properties against at least one of the tested bacterial strains, with minimal inhibitory concentrations (MICs) ranging from 250 to 1000 µg/mL. The n-butanol (n-BuOH) fraction was the most active against Escherichia coli ATCC 25922, with an MIC value of 250 µg/mL. Among the isolated compounds, schweinfurthin B (10) exhibited the best activity against Staphylococcus aureus NR 46003 with a MIC value of 62.5 µg/mL. In addition, schweinfurthin O (9) and isomacarangin (6) also exhibited moderate activity against the same strain with a MIC value of 125 µg/mL. Therefore, pharmacomodulation was performed on compound 6 and three new semisynthetic derivatives (6a-c) were prepared by allylation and acetylation reactions and screened for their in vitro antimicrobial activity. None of the semisynthetic derivatives showed antimicrobial activity against the same tested strains. The chemophenetic significance of the isolated compounds is also discussed in this paper.


Assuntos
Anti-Infecciosos , Euphorbiaceae , 1-Butanol , Extratos Vegetais/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Antibacterianos/química , Testes de Sensibilidade Microbiana
4.
Molecules ; 27(23)2022 Dec 05.
Artigo em Inglês | MEDLINE | ID: mdl-36500641

RESUMO

Six new polyoxygenated terpenoids, podovirosanes A-F (1-6), and two known polyketides (7 and 8) were isolated from the roots of F. virosa. Their structures, along with absolute configurations, were deduced using spectroscopic analysis as well as computational calculations, including TDDFT calculation of ECD spectra and GIAO NMR calculations combined with DP4+ probability analysis. Compounds 2, 3, 5, and 8 were found to reduce the phosphorylation levels of NF-κB p65 in SARS-CoV-2 pseudovirus-stimulated PMA-differentiated THP-1 cells.


Assuntos
COVID-19 , Euphorbiaceae , Policetídeos , Terpenos/farmacologia , Terpenos/química , Euphorbiaceae/química , SARS-CoV-2 , Policetídeos/farmacologia , Estrutura Molecular
5.
J Nat Prod ; 85(11): 2687-2693, 2022 Nov 25.
Artigo em Inglês | MEDLINE | ID: mdl-36378070

RESUMO

Four new diterpene esters, shirakindicans A-D (1-4), along with eight related known diterpene esters (5-12), were isolated from the fruits of the Bangladeshi medicinal plant Shirakiopsis indica. The structures of 1-4 were elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Shirakindican A (1) was assigned as a tigliane-type diterpene ester possessing an unusual 6ß-hydroxy-1,7-dien-3-one structure, while shirakindican B (2) exhibits a tiglia-1,5-dien-3,7-dione structure. The anti-HIV activities of the isolated diterpene esters were evaluated and showed significant activities for sapintoxins A (5) and D (11), with EC50 values of 0.0074 and 0.044 µM, respectively, and TI values of 1 100 and 5 290. Sapatoxin A (12) also exhibited anti-HIV activity with an EC50 value of 0.13 µM and a TI value of 161.


Assuntos
Fármacos Anti-HIV , Euphorbiaceae , HIV , Ésteres de Forbol , Euphorbiaceae/química , Frutas/química , Estrutura Molecular , HIV/efeitos dos fármacos , Ésteres de Forbol/química , Ésteres de Forbol/isolamento & purificação , Ésteres de Forbol/farmacologia , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Linhagem Celular , Humanos
6.
Molecules ; 27(21)2022 Oct 27.
Artigo em Inglês | MEDLINE | ID: mdl-36364140

RESUMO

Andean lupin (Lupinus mutabilis) oil is rich in monounsaturated (54.2%) and polyunsaturated (28.5%) fatty acids but has a ω-3:ω-6 ratio (1:9.2) above the recommended values for human health. Sacha inchi (Plukenetia volubilis) oil presents a high polyunsaturated fatty acid content (linolenic 47.2% and linoleic 34.7%), along a ω-3:ω-6 ratio (1:0.74) good for human consumption. The objective of this research was to study the physico-chemical properties and oxidative stability of tarwi and sacha inchi oil blends (1:4, 1:3, 1:1, 3:1 and 4:1 w:w) with suitable ω-3:ω-6 ratios. All blends showed ω-3:ω-6 ratios between 1:0.8 and 1:1.9, acceptable from a nutritional point of view, and high total tocopherols' content (1834-688 mg/kg), thanks to sacha inchi. The oxidative stability index (OSI) of the mixtures by the Rancimat method at 120 °C ranged from 0.46 to 8.80 h. The shelf-life of 1:1 tarwi/sacha inchi oil blend was 1.26 years; its entropy (-17.43 J/mol), enthalpy (107.04 kJ/mol), activation energy (110.24 kJ/mol) and Gibbs energy (113.76 kJ/mol) suggest low oxidation reaction rates and good stability. Hence, balanced blends of tarwi/sacha inchi oils can achieve optimal nutritional properties and enhanced shelf-life.


Assuntos
Euphorbiaceae , Ácidos Graxos Ômega-3 , Lupinus , Humanos , Óleos Vegetais/química , Euphorbiaceae/química , Sementes/química , Ácidos Graxos Ômega-3/análise , Valor Nutritivo , Estresse Oxidativo
7.
Molecules ; 27(21)2022 Oct 31.
Artigo em Inglês | MEDLINE | ID: mdl-36364225

RESUMO

Chaya and amaranth are Mexican traditional foods with a high nutritional value. Many studies have demonstrated the individual beneficial effect of each. However, there is no evidence of the use of these foods on the formulation of functional foods. This study evaluated the effect of replacing 5-20% of wheat flour with chaya and amaranth flours to generate four different formulations of cookies. Proximal analysis, total polyphenols and oxalate content, antioxidant activity, fatty acid profile, and sensory analysis were performed on the cookies. The results of the chemical composition showed that all cookies have a high protein content (9.21-10.10%), an adequate amount of fiber (5.34-6.63%), and a balanced ratio of unsaturated-saturated fatty acids (70:20), and they contain PUFAs (50.4-53.2 g/100 g of fatty acids), especially α-linolenic and oleic acids. All formulations presented antioxidant activity (2540 ± 65.9 to 4867 ± 61.7 Trolox equivalents (µmoles/100 g)) and polyphenols (328-790 mg/100 g); in particular, quercetin was identified in their composition. Results of the sensory analysis indicated that incorporation of chaya and amaranth flour in cookies does not affect the acceptability of the products. The inclusion of traditional foods, such as chaya and amaranth, in cookies enhances their nutritional value and increases the content of bioactive compounds associated with health effects.


Assuntos
Amaranthus , Euphorbiaceae , Amaranthus/química , Farinha/análise , Antioxidantes/análise , Triticum , Valor Nutritivo , Polifenóis/análise , Ácidos Graxos/análise
8.
Am J Bot ; 109(11): 1906-1917, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36371715

RESUMO

PREMISE: Flower phenotypes evolve to attract pollinators and to ensure efficient pollen transfer to and from the bodies of pollinators or, in self-compatible bisexual flowers, between anthers and stigmas. If functionally interacting traits are genetically correlated, response to selection may be subject to genetic constraints. Genetic constraints can be assessed by quantifying standing genetic variation in (multivariate) phenotypic traits and by asking how much the available variation is reduced under specific assumptions about phenotypic selection on functionally interacting and genetically correlated traits. METHODS: We evaluated multivariate evolvability and potential genetic constraints underlying the evolution of the three-dimensional structure of Dalechampia blossoms. First, we used data from a greenhouse crossing design to estimate the G matrix for traits representing the relative positions of male and female sexual organs (anthers and stigmas) and used the G matrix to ask how genetic variation is distributed in multivariate space. To assess the evolutionary importance of genetic constraints, we related standing genetic variation across phenotypic space to evolutionary divergence of population and species in the same phenotypic directions. RESULTS: Evolvabilities varied substantially across phenotype space, suggesting that certain traits or trait combinations may be subject to strong genetic constraint. Traits involved functionally in flower-pollinator fit and autonomous selfing exhibited considerable independent evolutionary potential, but population and species divergence tended to occur in phenotypic directions associated with greater-than-average evolvability. CONCLUSIONS: These results are consistent with the hypothesis that genetic constraints can hamper joint trait evolution towards optimum flower-pollinator fit and optimum self-pollination rates.


Assuntos
Evolução Biológica , Euphorbiaceae , Flores/fisiologia , Polinização , Fenótipo , Euphorbiaceae/genética
9.
F1000Res ; 11: 702, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-36339983

RESUMO

Background: Given the chemical richness of medicinal plants ( Bidens pilosa L. and Croton floccosus) in Ecuador, they are considered the natural source of numerous medicines. Methods: The leaves were dried at 40°C and 50°C and the extracts were characterized by means of phytochemical screening, verifying the presence of secondary metabolites such as alkaloids, reducing sugars, phenols, flavonoids, tannins and saponins. Three extraction processes were carried out, with two solvents of different polarities: hexane and ethanol. The extraction methods that were applied to the leaves of the plants were Soxhlet, ultrasonic bath and maceration, the latter two at room temperature and Soxhlet at the boiling temperature of the solvent. Determination of the total content of phenols and flavonoids is carried out using the Follin-Ciocalteau colorimetric reaction, Quercetin standard, Aluminum Chloride solution measured with a UV-Vis spectrophotometer. The antioxidant activity was performed with the DPPH radical and measured with the same equipment. Results: The highest content of total phenols obtained by employing the Soxhlet method for extraction when the material was dried at 50°C was 48.609 ± 0.370 mg GAE/g of dry sample for Bidens pilosa L. while in the case of Croton floccosus it was 128.212 ± 0.601 mg GAE/g of dry sample obtained from the extraction by means of maceration. Finally, the antioxidant activity against the 1.1-diphenyl-2-picryl-hydrazyl radical was determined, and it was found that the Bidens pilosa L. species performed better and responded better to the test, with an IC 50 value of 239.33 µg/mL, than Croton floccosus (IC 50 of 644.125 µg/mL). Conclusions: The following preliminary phytochemical study of the Bidens pilosa L. and Croton floccosus plants provided important information on the content of secondary metabolites and response to the DPPH radical reported for the first time in Ecuador, which may be future use for medicinal application.


Assuntos
Asteraceae , Bidens , Croton , Euphorbiaceae , Antioxidantes , Extratos Vegetais/farmacologia , Compostos Fitoquímicos , Flavonoides/química , Fenóis
10.
Chem Pharm Bull (Tokyo) ; 70(12): 901-906, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-36450588

RESUMO

From the less polar fraction of the MeOH extract of the leaves and twigs of Omphalea oppositifolia, five new ent-rosane-type diterpenoids, named omphalines A-E (1-5), were isolated together with one known compound, 7-keto-ent-kaurane-16ß,17-diol (6), by a combination of various kinds of chromatography. The structure of omphaline A (1) was elucidated to be 19-nor-ent-rosane-4,15-diene-2ß,6α-diol-3-one. Omphalines B (2), C (3), D (4), and E (5) possessed two double bonds at 5- and 15-positions, and hydroxy functional groups at 3ß-, 2α,3α-, 2α,3ß-, and 2α,19-positions, respectively. The absolute configuration of 1 was determined by the comparison of the experimental electronic circular dichroism (ECD) spectrum and calculated ECD spectra.


Assuntos
Diterpenos do Tipo Caurano , Diterpenos , Euphorbiaceae , Madagáscar , Dicroísmo Circular
11.
Molecules ; 27(19)2022 Sep 22.
Artigo em Inglês | MEDLINE | ID: mdl-36234776

RESUMO

Plutella xylostella L. is one of the world's major pests of cruciferous crops. The indiscriminate use of synthetic insecticides has led to insecticide resistance and resurgence, and has been harmful to non-target organisms and the environment. Botanical insecticides are the best alternatives to synthetic pesticides for the management of pests in organic agriculture and integrated management. T. sebifera is an invasive species and has good potential as an insecticide due to the availability of plant material in some parts of India. The antifeedant activities of T. sebifera have not been reported against P. xylostella and other lepidopteron insects to date. Therefore, the current study targeted the characterization of leaf and bark extracts, feeding deterrence, synergistic and detoxification enzyme activities of leaf/bark ethanolic extracts/fractions, seed oil, and isolated compounds. UHPLC-QTOF-IMS analysis showed that shikimic acid, xanthoxylin, quercetin, kaempferol, methyl gallate, and stigmasterol are common metabolites identified in leaf and bark extracts. The combination of seed oil with bark extract showed higher deterrence (DC50 = 317.10 mg/L) as compared to leaf/bark extracts alone. Gallic acid showed higher deterrence (67.48%) than kaempferol and quercetin. The n-butanol fraction of bark was more repellent (RC50 = 414.61 mg/L). Based on DC50, the seed oil with leaf extract (1:1 ratio) alone with choice and seed oil with leaf and bark extract without choice showed synergistic interaction, but seed oil with bark extract with choice showed additive interaction. The ethanol extract of leaf, bark, and seed oil inhibited GST and AChE in P. xylostella. The leaf extract and seed oil or their combinations may be recommended as antifeedants to reduce damage by P. xylostella based on persistence, antifeedant, phytotoxicity, safety to predators/parasitoids, etc., under field conditions.


Assuntos
Euphorbiaceae , Inseticidas , Mariposas , 1-Butanol/farmacologia , Animais , Etanol/farmacologia , Ácido Gálico/farmacologia , Inseticidas/farmacologia , Quempferóis/farmacologia , Larva , Extratos Vegetais/farmacologia , Óleos Vegetais/farmacologia , Quercetina/farmacologia , Ácido Chiquímico , Estigmasterol/farmacologia
12.
Fitoterapia ; 162: 105302, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-36116613

RESUMO

Ten new prenylated flavonoids, named denticulains A-J (1-10), together with seven known prenylated flavonoids (11-17) were isolated from Macaranga denticulata. Their structures were elucidated on the basis of detailed spectroscopic analysis and by comparison with literature data. In addition, compounds 1 and 14 inhibited the proliferation of SW620 and HCT-116 cell lines with an IC50 value of 46.08 µM and 56.83 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos , Euphorbiaceae , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Euphorbiaceae/química , Flavonoides/química , Flavonoides/farmacologia , Estrutura Molecular
13.
Nat Commun ; 13(1): 5149, 2022 09 02.
Artigo em Inglês | MEDLINE | ID: mdl-36056139

RESUMO

Securinega alkaloids have fascinated the synthetic chemical community for over six decades. Historically, major research foci in securinega alkaloid synthesis have been on the efficient construction of the fused tetracyclic framework that bears a butenolide moiety and tertiary amine-based heterocycles. These "basic" securinega alkaloids have evolved to undergo biosynthetic oxidative diversifications, especially on the piperidine core. However, a general synthetic solution to access these high-oxidation state securinega alkaloids is lacking. In this study, we have completed the total synthesis of various C4-oxygenated securinine-type alkaloids including securingines A, C, D, securitinine, secu'amamine D, phyllanthine, and 4-epi-phyllanthine. Our synthetic strategy features stereocontrolled oxidation, rearrangement, and epimerization at N1 and C2-C4 positions of the piperidine core within (neo)securinane scaffolds. Our discoveries provide a fundamental synthetic solution to all known securinine-type natural products with various oxidative and stereochemical variations around the central piperidine ring.


Assuntos
Alcaloides , Euphorbiaceae , Azepinas , Compostos Heterocíclicos de Anel em Ponte , Lactonas , Piperidinas , Estereoisomerismo
14.
Braz J Biol ; 82: e264356, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-36169527

RESUMO

The search for compounds with anticancer effects is of paramount importance today due to the high incidence of the disease. The Euphorbiaceae family is known for having compounds with therapeutic properties, one of its genera being Croton. It has several species, which contain compounds already known for their biological activities, presenting anti-inflammatory, antimicrobial and anticancer properties. Thus, the cytotoxicity/antiproliferative activity of semi-purified fractions and compounds isolated from Croton echioides in liver tumor cells of Rattus norvegicus (HTC) was evaluated by the MTT test. The semi-purified fractions showed cytotoxicity at concentrations above 200 µg/mL, at 24, 48 and 72 hours, reaching cell viability of 24.78% [400 µg/mL] at 24 hours, 12.79% [500 µg/mL] at 48 hours and 10.57% [300 µg/mL] at 72 hours. For the isolated compounds, lupeol had a cytotoxic effect in all concentrations (1, 5, 10, 15, 20, 40, 60, 80 and 100 µg/mL) and tested times (24, 48 and 72 hours), reaching minimum viability of 4.37% [100 µg/mL], within 72 hours. The clerodan diterpenes CEH-1 and CEH-4 also showed antiproliferative activity, with minimum viability of 36.19% [100 µg/mL] over 72 hours and 21.33% [100 µg/mL] over 48 hours, respectively. However, the clerodan diterpenes CEH-2 and CEH-3 did not shows a cytotoxic effect for HTC cells. Thus, there is a cytotoxic/antiproliferative potential of C. echioides against tumor cells, with targeted to mitochondrial enzymes, associated with cell proliferation, indicating that this species deserves prominence in the search for new molecules for the treatment of cancer.


Assuntos
Antineoplásicos , Croton , Diterpenos , Euphorbiaceae , Animais , Anti-Inflamatórios/farmacologia , Antineoplásicos/farmacologia , Extratos Vegetais/toxicidade , Ratos
15.
J Nat Prod ; 85(8): 1959-1966, 2022 08 26.
Artigo em Inglês | MEDLINE | ID: mdl-35973043

RESUMO

The kernels of the Australian blushwood tree (Fontainea picrosperma) are the source of the veterinary anticancer drug tigilanol tiglate (2a, Stelfonta) and contain a concentration of phorboids significantly higher than croton oil, the only abundant source of these compounds previously known. The oily matrix of the blushwood kernels is composed of free fatty acids and not by glycerides as found in croton oil. By active partitioning, it was therefore possible to recover and characterize for the first time a cryptic tigliane fraction, that is, the diterpenoid fraction that, because of its lipophilicity, could not be obtained by solvent partition of crude extracts. The cryptic tigliane fraction accounted for ca. 30% of the tigliane kernel titer and was quantified by 1H NMR spectroscopy and profiled by HPLC-MS. Long-chain (linoleates and/or oleates) 20-acyl derivatives of the epoxytigliane diesters tigilanol tiglate (EBC-46, 2a), EBC-47 (4a), EBC-59 (5a), EBC-83 (6a), and EBC-177 (7a) were identified. By chemoselective acylation of EBC-46 (2a) and EBC-177 (7a) the natural triesters 2b and 7b and a selection of analogues were prepared to assist identification of the natural compounds. The presence of a free C-20 hydroxy group is a critical requirement for PKC activation by phorbol esters. The unexpected activity of 20-linoleoyl triester 2b in a cytotoxicity assay based on PKC activation was found to be related mainly to its hydrolysis to tigilanol tiglate (2a) under the prolonged conditions of the assay, while other esters were inactive. Significant differences between the esterification profile of the epoxytigliane di- and triesters exist in F. picrosperma, suggesting a precise, yet elusive, blueprint of acyl decoration for the tigliane polyol 5-hydroxyepoxyphorbol.


Assuntos
Euphorbiaceae , Forbóis , Austrália , Óleo de Cróton , Árvores
16.
Commun Biol ; 5(1): 786, 2022 08 04.
Artigo em Inglês | MEDLINE | ID: mdl-35927438

RESUMO

The Chinese tallow tree (Triadica sebifera) can produce oil with high content of unsaturated fatty acids in seeds and shows attractive leaf color in autumn and winter. Here, the 739 Mb chromosome-scale genome sequence of the Chinese tallow tree was assembled and it reveals the Chinese tallow tree is a tetraploid. Numerous genes related to nutrition assimilation, energy utilization, biosynthesis of secondary metabolites and resistance significantly expanded or are specific to the Chinese tallow tree. These genes would enable the Chinese tallow tree to obtain high adaptability. More genes in fatty acids biosynthesis in its genome, especially for unsaturated fatty acids biosynthesis, and higher expression of these genes in seeds would be attributed to its high content of unsaturated fatty acids. Cyanidin 3-O-glucoside was identified as the major component of anthocyanin in red leaves. All structural genes in anthocyanin biosynthesis show significantly higher expression in red leaves than in green leaves. Transcription factors, seven MYB and one bHLH, were predicted to regulate these anthocyanin biosynthesis genes. Collectively, we provided insight into the polyploidization, high adaptability and biosynthesis of the high content of unsaturated fatty acids in seeds and anthocyanin in leaves for the Chinese tallow tree.


Assuntos
Antocianinas , Proteínas de Plantas , Antocianinas/genética , Cromossomos , Euphorbiaceae , Ácidos Graxos , Proteínas de Plantas/metabolismo
17.
Int J Biol Macromol ; 221: 796-805, 2022 Nov 30.
Artigo em Inglês | MEDLINE | ID: mdl-36037910

RESUMO

The tung oil produced by the tung tree (Vernicia fordii) provides resources for the manufacture of biodiesel. Ubiquitin-specific proteases (UBPs) are the largest group of deubiquitinases and play key roles in regulating development and stress responses. Here, 21 UBPs were identified in V. fordii, roughly one-half the number found in Manihot esculenta and Hevea brasiliensis. Most UBP duplications are produced from whole-genome duplication (WGD), and significant differences in gene retention existed among Euphorbiaceae. The great majority of UBP-containing blocks in V. fordii, V. montana, Ricinus communis, and Jatropha curcas exhibited extensive conservation with the duplicated regions of M. esculenta and H. brasiliensis. These blocks formed 14 orthologous groups, indicating they shared WGD with UBPs in M. esculenta and H. brasiliensis, but most of these UBPs copies were lost. The UBP orthologs contained significant functional divergence which explained the susceptibility of V. fordii to Fusarium wilt and the resistance of V. montana to Fusarium wilt. The expression patterns and experiments suggested that Vf03G1417 could affect the seed-related traits and positively regulate the seed oil accumulation. This study provided important insights into the evolution of UBPs in Euphorbiaceae and identified important candidate VfUBPs for marker-assisted breeding in V. fordii.


Assuntos
Aleurites , Euphorbiaceae , Hevea , Proteases Específicas de Ubiquitina , Melhoramento Vegetal , Aleurites/genética , Sementes/genética , Sementes/metabolismo , Hevea/metabolismo , Euphorbiaceae/genética
18.
Molecules ; 27(13)2022 Jul 05.
Artigo em Inglês | MEDLINE | ID: mdl-35807565

RESUMO

Chrozophora tinctoria is an annual plant of the family Euphorbiaceae, traditionally used as a laxative, a cathartic and an emetic. A methanolic extract of Chrozophora tinctoria (MEC) whole plant and an n-butanol fraction of Chrozophora tinctoria (NBFC) were analyzed by gas chromatography-mass spectrometry (GC-MS) to detect the phytochemicals. MEC and NBFC were tested for in vitro anti acetylcholinesterase (AChE) potential. The effect of both samples on intestinal propulsive movement and spasmolytic activity in the gastrointestinal tract (GIT) was also studied. About twelve compounds in MEC and three compounds in NBFC were tentatively identified through GC-MS. Some of them are compounds with known therapeutic activity, such as toluene; imipramine; undecane; 14-methyl-pentadecanoic acid methyl ester; and hexadecanoic acid. Both NBFC and MEC samples were checked for acute toxicity and were found to be highly toxic in a dose-dependent manner, causing diarrhea and emesis at 1 g/kg concentration in pigeons, with the highest lethargy and mortality above 3 g/kg. Both the samples of Chrozophora tinctoria revealed significant (p ≤ 0.01) laxative activity against metronidazole (7 mg/kg) and loperamide hydrochloride (4 mg/kg)-induced constipation. NBFC (81.18 ± 2.5%) and MEC (68.28 ± 2.4%) significantly increased charcoal meal intestinal transit compared to distal water (41.15 ± 4.3%). NBFC exhibited a significant relaxant effect (EC50 = 3.40 ± 0.20 mg/mL) in spontaneous rabbit jejunum as compared to MEC (EC50 = 4.34 ± 0.68 mg/kg). Similarly, the impact of NBFC on KCl-induced contraction was more significant than that of MEC (EC50 values of 7.22 ± 0.06 mg/mL and 7.47 ± 0.57 mg/mL, respectively). The present study scientifically validates the folk use of Chrozophora tinctoria in the management of gastrointestinal diseases such as constipation. Further work is needed to isolate the phytochemicals that act as diarrheal agents in Chrozophora tinctoria.


Assuntos
Euphorbiaceae , Laxantes , Animais , Constipação Intestinal/induzido quimicamente , Constipação Intestinal/tratamento farmacológico , Diarreia/induzido quimicamente , Diarreia/tratamento farmacológico , Euphorbiaceae/química , Laxantes/farmacologia , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/uso terapêutico , Extratos Vegetais/química , Coelhos
19.
PLoS Genet ; 18(7): e1010226, 2022 07.
Artigo em Inglês | MEDLINE | ID: mdl-35793353

RESUMO

Polyploidization may precipitate dramatic changes to the genome, including chromosome rearrangements, gene loss, and changes in gene expression. In dioecious plants, the sex-determining mechanism may also be disrupted by polyploidization, with the potential evolution of hermaphroditism. However, while dioecy appears to have persisted through a ploidy transition in some species, it is unknown whether the newly formed polyploid maintained its sex-determining system uninterrupted, or whether dioecy re-evolved after a period of hermaphroditism. Here, we develop a bioinformatic pipeline using RNA-sequencing data from natural populations to demonstrate that the allopolyploid plant Mercurialis canariensis directly inherited its sex-determining region from one of its diploid progenitor species, M. annua, and likely remained dioecious through the transition. The sex-determining region of M. canariensis is smaller than that of its diploid progenitor, suggesting that the non-recombining region of M. annua expanded subsequent to the polyploid origin of M. canariensis. Homeologous pairs show partial sexual subfunctionalization. We discuss the possibility that gene duplicates created by polyploidization might contribute to resolving sexual antagonism.


Assuntos
Transtornos do Desenvolvimento Sexual , Euphorbiaceae , Cromossomos , Diploide , Transtornos do Desenvolvimento Sexual/genética , Euphorbiaceae/genética , Poliploidia
20.
Phytochemistry ; 202: 113300, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-35798090

RESUMO

Thirty-three natural products were isolated from the aerial parts of Antidesma bunius, Euphorbiaceae, a plant used in Vietnamese traditional medicine against rheumatoid arthritis. All compounds were reported the first time for this species, and nine constituents resembled undescribed natural products, noticeably three coumarinolignans with 2,2-dimethyl-1,3-dioxolane moiety, two cyclopeptides, and two furofuran-type lignans connected with a phenylpropanoid moiety. The individual structures were elucidated by combining NMR and MS data, and their configuration was established by NOESY and ECD experiments and NMR calculations. Compounds with sufficient amount were analyzed for their inhibition of advanced glycation endproducts (AGEs) formation, metabolites involved in many diseases like Alzheimer, joint diseases or diabetes. With IC50 values below 0.2 mM rutin and p-hydroxyphenethyl trans-ferulate showed to be moderately active, both still being 10-times more active than the positive control aminoguanidine.


Assuntos
Produtos Biológicos , Euphorbiaceae , Euphorbiaceae/química , Produtos Finais de Glicação Avançada , Componentes Aéreos da Planta , Vietnã
SELEÇÃO DE REFERÊNCIAS
DETALHE DA PESQUISA
...