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1.
Molecules ; 27(21)2022 Oct 24.
Artigo em Inglês | MEDLINE | ID: mdl-36364025

RESUMO

Euphorbia officinarum L. is a Moroccan endemic plant known as "Tikiout" and "Daghmus" that can also be found in Mauritania, Western Sahara, and Algeria. In the present review, "Euphorbia officinarum", "metabolites" "hemisynthesis" were the keywords used for the research in the Web search engine Google Scholar and in the database Web of Science. Triterpenes, phytosterols and ingol diterpenes were isolated and identified in the latex of Moroccan E. officinarum. More than sixty triterpenes were obtained by hemisynthesis from natural triterpenes. Some of these derivatives had insecticidal and antimicrobial activity (phytopathogenic bacteria). The total phenol content and the antioxidant and anti-α-glucosidase activities were dependent on the time and temperature of extractions and also on the plant solvent ratio. The antioxidant activity of monofloral honey of E. officinarum origin was attributed to the phenol fraction (this fraction, previously isolated from honey samples, had better activity than the entire honey).


Assuntos
Diterpenos , Euphorbia , Triterpenos , Abelhas , Animais , Látex , Antioxidantes/farmacologia , Fenóis/farmacologia , Extratos Vegetais/farmacologia
2.
Molecules ; 27(21)2022 Oct 26.
Artigo em Inglês | MEDLINE | ID: mdl-36364087

RESUMO

The roots of Euphorbia fischeriana have been used as a traditional Chinese medicine for the treatment of tuberculosis and ringworm. In the current study, diterpenoids from the ethyl acetate extract of the roots E. fischeriana and their cytotoxic effects against five cancer lines were investigated. Two new ent-abietane diterpenoids, euphonoids H and I (1-2), as well as their two analogues (3-4) were first isolated from this source. The structures of the two new compounds were elucidated on the basis of spectroscopic data and quantum chemical calculation. Their absolute configurations were assigned via ECD spectrum calculation. The isolated compounds were evaluated for their antiproliferative activities against five cancer cell lines. Compounds 1 and 2 exhibited significant inhibitory effects against human prostate cancers C4-2B and C4-2B/ENZR cell lines with IC50 values ranging from 4.16 ± 0.42 to 5.74 ± 0.45 µM.


Assuntos
Antineoplásicos Fitogênicos , Antineoplásicos , Diterpenos , Euphorbia , Neoplasias , Humanos , Euphorbia/química , Abietanos/farmacologia , Abietanos/análise , Diterpenos/química , Antineoplásicos/análise , Raízes de Plantas/química , Estrutura Molecular , Antineoplásicos Fitogênicos/química
3.
Molecules ; 27(20)2022 Oct 16.
Artigo em Inglês | MEDLINE | ID: mdl-36296525

RESUMO

Euphorbia factors, lathyrane-type diterpenoids isolated from the medical herb Euphorbia lathyris L. (Euphorbiaceae), have been associated with intestinal irritation toxicity, but the mechanisms underlying this phenomenon are still unknown. The objective of this study was to evaluate the transcriptome and miRNA profiles of human colon adenocarcinoma Caco-2 cells in response to Euphorbia factors L1 (EFL1) and EFL2. Whole transcriptomes of mRNA and microRNA (miRNA) were obtained using second generation high-throughput sequencing technology in response to 200 µM EFL treatment for 72 h, and the differentially expressed genes and metabolism pathway were enriched. Gene structure changes were analyzed by comparing them with reference genome sequences. After 72 h of treatment, 16 miRNAs and 154 mRNAs were differently expressed between the EFL1 group and the control group, and 47 miRNAs and 1101 mRNAs were differentially expressed between the EFL2 group and the control. Using clusters of orthologous protein enrichment, the sequenced mRNAs were shown to be mainly involved in transcription, post-translational modification, protein turnover, chaperones, signal transduction mechanisms, intracellular trafficking, secretion, vesicular transport, and the cytoskeleton. The differentially expressed mRNA functions and pathways were enriched in transmembrane transport, T cell extravasation, the IL-17 signaling pathway, apoptosis, and the cell cycle. The differentially expressed miRNA EFLs caused changes in the structure of the gene, including alternative splicing, insertion and deletion, and single nucleotide polymorphisms. This study reveals the underlying mechanism responsible for the toxicity of EFLs in intestinal cells based on transcriptome and miRNA profiles of gene expression and structure.


Assuntos
Adenocarcinoma , Neoplasias do Colo , Diterpenos , Euphorbia , MicroRNAs , Humanos , Euphorbia/química , Transcriptoma , Células CACO-2 , Interleucina-17/genética , Neoplasias do Colo/genética , Diterpenos/farmacologia , Diterpenos/química , MicroRNAs/genética , MicroRNAs/metabolismo , RNA Mensageiro/genética , Perfilação da Expressão Gênica
4.
Arch Microbiol ; 204(11): 661, 2022 Oct 04.
Artigo em Inglês | MEDLINE | ID: mdl-36192448

RESUMO

The antimicrobial activity of endophytic fungi isolated from Euphorbia milii was evaluated against Gram-positive, Gram-negative bacteria, unicellular yeast, and filamentous fungi. Chaetomium ovatoascomatis NRC was identified morphologically and genetically as the most active strain. The total ethyl acetate extract of C. ovatoascomatis NRC demonstrated significant antimicrobial activity against Gram-negative; Escherichia coli, Salmonella enteric, and fungi; Aspergillus niger with MIC of 62.5 ug/ml. Whereas n-hexane fraction demonstrated broader activity against Gram-positive; Bacillus subtilis, Lactobacillus cereus, Gram-negative; Escherichia coli and Salmonella enteric, fungi; Candida albicans and F. solani. LC-MS/MS analysis of ethyl acetate strain extract and GC-MS analysis of the n-hexane fraction were used to identify the metabolites of the strain extract. LC-MS/MS determined three major metabolites with potential antimicrobial activities including grevilline B, aflatoxin G2 and apigenin. GC-MS analysis of n-hexane fraction tentatively identified 30 compounds, where 9,12-octadecadienoic acid methyl ester was the major compound.


Assuntos
Anti-Infecciosos , Chaetomium , Euphorbia , Acetatos , Anti-Infecciosos/metabolismo , Anti-Infecciosos/farmacologia , Apigenina/metabolismo , Apigenina/farmacologia , Bacillus subtilis , Cromatografia Líquida , Endófitos , Escherichia coli , Ésteres/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Bactérias Gram-Negativas , Hexanos , Ácido Linoleico/metabolismo , Ácido Linoleico/farmacologia , Testes de Sensibilidade Microbiana , Compostos Fitoquímicos/farmacologia , Espectrometria de Massas em Tandem
5.
Eur J Med Chem ; 244: 114822, 2022 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-36242992

RESUMO

Use of novel modulators targeting P-glycoprotein (P-gp, ABCB1 transporter) is among the most accepted strategies for overcoming multidrug resistance in cancer chemotherapy. In the current study, we pursued our structure-activity relationship studies of jatrophane derivatives by structural modification of compound 1, a natural jatrophane isolated from Euphorbia. sororia A. Nine compounds exhibited higher reversal activity in P-gp/ABCB1-mediated MCF-7/ADR cells than verapamil (VRP). The cytotoxicity and doxorubicin (DOX) intracellular accumulation effects of jatrophane derivatives were assessed in normal HEK293T cells and DOX-resistant MCF-7/ADR cells. The most potent compound 17 merits multiple activities, including (1) high efficiency (EC50 = 182.17 ± 32.67 nM) in reversing P-gp-mediated resistance to DOX, low cytotoxicity, and a high therapeutic index; and (2) increasing the accumulation of Rhodamine123 (Rho123) and DOX in a dose-dependent manner compared to verapamil in MCF-7/ADR cells. Our results indicated that the reversal activity of 17 was due to the stimulation of the P-gp ATPase activity instead of the direct inhibition of P-gp protein expression. A docking study demonstrated that 17 has a high binding affinity toward the DOX recognition site of P-gp. This resulted in 17 enhancing the sensitivity of DOX to MCF-7/ADR cells by stimulating P-gp ATPase activity, increasing intracellular DOX and Rho123 concentrations, inhibiting the phosphoinositide 3-kinase/serine-threonine kinase mediated by DOX and further reducing the expression of P-gp. This study provides a promising P-gp inhibitor for reversing multidrug resistance and provides a basis for further research.


Assuntos
Membro 1 da Subfamília B de Cassetes de Ligação de ATP , Euphorbia , Humanos , Células MCF-7 , Células HEK293 , Fosfatidilinositol 3-Quinases/metabolismo , Resistencia a Medicamentos Antineoplásicos , Doxorrubicina/farmacologia , Subfamília B de Transportador de Cassetes de Ligação de ATP , Verapamil/farmacologia , Adenosina Trifosfatases/metabolismo
6.
Drug Dev Ind Pharm ; 48(8): 406-416, 2022 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-36268597

RESUMO

OBJECTIVES: The present study aims to investigate the protective effect of Euphorbia thymifolia and Euphorbia hirta extracts on in vitro antioxidant activity and in vivo analysis on hepatic marker enzyme levels and histopathological changes in the liver of carbon tetrachloride (CCl4) induced hepatotoxicity rats. MATERIALS AND METHODS: This study includes 42 adult male Albino Wistar rats randomly divided into seven treatment groups, including control (basal diet, G1), CCl4-induced single dose (1.5 ml/kg, i.p.) as the negative control (G2), G1 supplemented with 300 mg/kg of ethanol extract of E. thymifolia (G3) and E. hirta (G4), G2 supplemented with 300 mg/kg of ethanol extract of E. thymifolia (G5), E. hirta (G6), and silymarin (25 mg/kg b.w.) used as a standard drug (G7) for 21-days experimental period. RESULTS: The ethanolic extracts of E. thymifolia and E. hirta exhibited potential in vitro antioxidant activity in a dose-dependent manner (25 µg/ml, 50 µg/ml, 100 µg/ml, 200 µg/ml and 250 µg/ml). Oxidative stress caused by CCl4-induced the liver damage, including changes in liver marker enzymes (aspartate aminotransferase, alanine aminotransferase, and alkaline phosphatase), enzymatic (superoxide dismutase and catalase), non-enzymatic antioxidants (lipid peroxides and glutathione) and hepatocellular alterations such as hydropic degeneration, irregular hepatocytes, and distention of the vein. Administration of E. thymifolia and E. hirta significantly (p < 0.05) restored the enzyme activity along with the histology of the liver. CONCLUSION: The results from the current study demonstrate that E. thymifolia and E. hirta have the property of restoring hepatic redox capacity and antioxidant activities against CCl4-induced acute liver damage.


Assuntos
Doença Hepática Induzida por Substâncias e Drogas , Euphorbia , Masculino , Ratos , Animais , Tetracloreto de Carbono , Antioxidantes/farmacologia , Antioxidantes/metabolismo , Ratos Wistar , Doença Hepática Induzida por Substâncias e Drogas/tratamento farmacológico , Doença Hepática Induzida por Substâncias e Drogas/etiologia , Doença Hepática Induzida por Substâncias e Drogas/prevenção & controle , Extratos Vegetais/farmacologia , Extratos Vegetais/metabolismo , Estresse Oxidativo , Fígado , Etanol/farmacologia , Peroxidação de Lipídeos
7.
J Org Chem ; 87(19): 13411-13415, 2022 10 07.
Artigo em Inglês | MEDLINE | ID: mdl-36126306

RESUMO

Naturally occurring 1(15 → 14)abeo-lathyrane rearrangement-type diterpene lathyranone A (1) was prepared from lathyrane-type Euphorbia factor L11 (1a) via an efficient Sc(OTf)3/Et2NH-catalyzed α-ketol rearrangement, which was also suitable for the synthesis of lathyranones 2 and 3. This skeletal conversion strategy had the characteristic of biogenetically patterned synthesis and provided a convenient method for accessing naturally rare functionalized lathyranones from lathyranes. Moreover, the absolute configuration of the lathyranone skeleton was confirmed for the first time by the X-ray diffraction of 2.


Assuntos
Diterpenos , Euphorbia , Catálise , Estrutura Molecular , Escândio , Esqueleto
8.
Biomed Pharmacother ; 155: 113723, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36156367

RESUMO

Amorphous calcium phosphate nanoparticles (ACP NPs) exhibit excellent biocompatibility and biodegradability properties. ACP NPs were functionalized with two coumarin compounds (esculetin and euphorbetin) extracted from Euphorbia lathyris seeds (BC-ACP NPs) showing high loading capacity (0.03% and 0.34% (w/w) for esculetin and euphorbetin, respectively) and adsorption efficiency (2.6% and 33.5%, respectively). BC-ACP NPs, no toxic to human blood cells, showed a more selective cytotoxicity against colorectal cancer (CRC) cells (T-84 cells) (IC50, 71.42 µg/ml) compared to non-tumor (CCD18) cells (IC50, 420.77 µg/ml). Both, the inhibition of carbonic anhydrase and autophagic cell death appeared to be involved in their action mechanism. Interestingly, in vivo treatment with BC-ACPs NPs using two different models of CRC induction showed a significant reduction in tumor volume (62%) and a significant decrease in the number and size of polyps. A poor development of tumor vasculature and invasion of normal tissue were also observed. Moreover, treatment increased the bacterial population of Akkermansia by restoring antioxidant systems in the colonic mucosa of mice. These results show a promising pathway to design innovative and more efficient therapies against CRC based on biomimetic calcium phosphate NPs loaded with natural products.


Assuntos
Produtos Biológicos , Anidrases Carbônicas , Neoplasias do Colo , Euphorbia , Nanopartículas , Humanos , Camundongos , Animais , Antioxidantes , Neoplasias do Colo/tratamento farmacológico , Cumarínicos , Fosfatos de Cálcio
9.
Phytochemistry ; 203: 113420, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36055424

RESUMO

Eight undescribed jatrophane diterpenoids, euphohelinoids A-H, along with 11 known analogues were isolated from the whole plant of Euphorbia heliosocpia L. Among them, euphohelinoids A and B contain a rare type of jatrophane diterpenoid skeleton with a 7,8-seco scaffold. To the best of our knowledge, only two such jatrophane diterpenoids have been reported. In addition, euphohelinoids G and H belong to a rare class of jatrophane diterpene possessing a ß-hydroxy group at C-11. Structure elucidation of these undescribed diterpenoids was performed by spectroscopic analysis, including NMR, HRESIMS, IR, electronic circular dichroism (ECD) and DP4+ analysis. The cytotoxicity of 17 abundant jatrophane diterpenes was evaluated against HepG2, HeLa, HL-60, and SMMC-7721 cell lines. Seven compounds presented potent cytotoxicity against the four tested cell lines with IC50 values from 8.1 to 29.7 µM. Moreover, preliminary structure-activity relationships for these jatrophane diterpenoids were discussed.


Assuntos
Antineoplásicos , Diterpenos , Euphorbia , Diterpenos/química , Diterpenos/farmacologia , Euphorbia/química , Estrutura Molecular , Relação Estrutura-Atividade
10.
Phytochemistry ; 203: 113426, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36084856

RESUMO

Endophytic fungi are striking resources rich in bioactive structures with agrochemical significance. In order to maximize the opportunity of search for bioactive compounds, chemical epigenetic manipulation was introduced to enhance the structural diversity of the fungal products, and an UPLC-ESIMS and bioassay-guided separation was used to detect novel bioactive metabolites. Consequently, four previously undescribed compounds including two cyclopentenones (globosporins A and B) and two monoterpenoid indole alkaloids (globosporines C and D), as well as three known compounds, were isolated from the endophytic fungus Chaetomium globosporum of Euphorbia humifusa by exposure to a DNA methyltransferase inhibitor 5-azacytidine. Their structures including the absolute configurations were elucidated by the analysis of NMR spectroscopic data, HRESIMS, and TD-DFT-ECD calculations. The indole alkaloids (globosporines C and D) showed antimicrobial activities against three phytopathogenic microbes (Xanthomonas oryzae pv. oryzae, X. oryzae pv. oryzicola, and Pseudomonas syringae pv. lachrymans) with MICs in the range of 14-72 µg/mL. Mostly, globosporine D was proved to be potently anti-phytopathogenic against X. oryzae pv. oryzae in vitro and in vivo, which suggested that it has the potential to be developed as a candidate for the prevention of rice bacterial leaf blight. This work provides an efficient and environmentally friendly approach for expanding fungal products with agricultural importance.


Assuntos
Anti-Infecciosos , Chaetomium , Euphorbia , Oryza , Alcaloides de Triptamina e Secologanina , Agroquímicos/metabolismo , Anti-Infecciosos/farmacologia , Azacitidina/metabolismo , Chaetomium/metabolismo , DNA/metabolismo , Epigênese Genética , Euphorbia/metabolismo , Alcaloides Indólicos/química , Metiltransferases/metabolismo , Oryza/metabolismo , Doenças das Plantas/microbiologia , Alcaloides de Triptamina e Secologanina/metabolismo
11.
Fitoterapia ; 162: 105296, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-36087821

RESUMO

Four new diterpenoids (1-4), and 18 known ones were isolated from the roots of Euphorbia fischeriana Steud (Euphorbiaceae). These diterpenoids shared six skeleton types, including ent-atisane, kaurane, 3,4-secokaurane, lathyrane, 4,5-secoatisane and ingenane diterpenoids. The structures of the new diterpenoids were characterized by a combination of spectroscopic techniques and X-ray crystallography. Moreover, biological evaluation revealed that compounds (16S*)-atisan-3ß,16,17-triol (7), (16S*)-3ß,16,17,18-tetrahydroxykaurane (12) and (16S*)-3α-hydroxykauran-16,17-acetonide (15) showed inhibitory activity against the interferon regulatory factors (IRFs) involved pathway.


Assuntos
Diterpenos do Tipo Caurano , Diterpenos , Euphorbia , Diterpenos/química , Diterpenos/farmacologia , Euphorbia/química , Fatores Reguladores de Interferon/análise , Estrutura Molecular , Raízes de Plantas/química
12.
Chem Biodivers ; 19(11): e202200660, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36156394

RESUMO

A serial jatrophane-type diterpenoids, comprised with three undescribed compounds kanesulones C-E (1-3) and four known ones (4-7), were obtained from the roots of Euphorbia kansui. The structures of compounds 1-3 were elucidated by detailed interpretation of their spectroscopic data, especially 2D-NMR and HR-ESI-MS, the absolute configuration of 1 was revealed by single crystal X-ray diffraction. These isolates were assayed for their multidrug resistance reversing activities on human breast adenocarcinoma cell line MCF-7/ADR. Compound 1 possessed potential as low toxic MDR modulator that could promote the efficacy of anticancer drug adriamycin ca. 85-fold at 5 µM, as 12 times stronger than the positive drug verapamil.


Assuntos
Diterpenos , Euphorbia , Humanos , Euphorbia/química , Estrutura Molecular , Diterpenos/farmacologia , Diterpenos/química , Resistência a Múltiplos Medicamentos
13.
Environ Toxicol ; 37(12): 2865-2876, 2022 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-36073799

RESUMO

Plant extracts were successfully applied to synthesize nanoparticles, and expected such biological processes of effective for chemotherapeutic applications and safe for human use. Our study planned to evaluate the anticancer efficacy of silver nanoparticles (AgNPs) synthesized by Euphorbia hirta on human lung adenocarcinoma A549 cells. The E. hirta synthesized Eh-AgNPs was investigated by UV-spectroscopy, X-ray diffraction, transmission electron microscopy, and Fourier-transform infrared spectroscopy examination. The bactericidal efficacy of Eh-AgNPs was studied by the agar well method, and the cytotoxicity on A549 cells was assessed by MTT assay. Results showed that Eh-AgNPs exhibited effective antibacterial activity against bacterial pathogens, established dose-dependent cytotoxicity on A549 cells, and persuaded apoptosis, as evidenced by increased lipid peroxidation and decreased levels of antioxidants. Eh-AgNPs significantly increased the early apoptosis in A549 cells in a concentration-dependent way. The Eh-AgNPs administration reduced the Bcl-2 expression; however, it increased the expression of p53, Bax, cleaved caspase-3 and -9 apoptotic members. Eh-AgNPs treatment reduced PI3Kγ, phospho-PI3K, phospho-Akt, phospho-mTOR, and p70S6K levels. The obtained results demonstrated that the Eh-AgNPs induce reactive oxygen species-mediated apoptosis by expressing p53, Bax, and inhibiting PI3K/Akt/mTOR/p70S6K signaling pathway.


Assuntos
Adenocarcinoma de Pulmão , Euphorbia , Nanopartículas Metálicas , Humanos , Prata/farmacologia , Prata/química , Nanopartículas Metálicas/toxicidade , Nanopartículas Metálicas/química , Células A549 , Fosfatidilinositol 3-Quinases , Proteínas Proto-Oncogênicas c-akt , Proteína X Associada a bcl-2 , Proteínas Quinases S6 Ribossômicas 70-kDa , Regulação para Baixo , Proteína Supressora de Tumor p53 , Apoptose , Antibacterianos/farmacologia , Antibacterianos/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Serina-Treonina Quinases TOR , Difração de Raios X
14.
Nat Prod Rep ; 39(11): 2132-2174, 2022 Nov 16.
Artigo em Inglês | MEDLINE | ID: mdl-36111621

RESUMO

Covering: 2013 to 2021As the characteristic metabolites of Euphorbia plants, Euphorbia diterpenoids have always been a hot topic in related science communities due to their intriguing structures and broad bioactivities. In this review, we intent to provide an in-depth and extensive coverage of Euphorbia diterpenoids reported from 2013 to the end of 2021, including 997 new Euphorbia diterpenoids and 78 known ones with latest progress. Multiple aspects will be summarized, including their occurrences, chemical structures, bioactivities, and syntheses, in which the structure-activity relationship and biosynthesis of this class will be discussed for the first time.


Assuntos
Diterpenos , Euphorbia , Euphorbia/química , Diterpenos/farmacologia , Diterpenos/química , Relação Estrutura-Atividade , Estrutura Molecular
15.
Bioorg Chem ; 128: 106067, 2022 11.
Artigo em Inglês | MEDLINE | ID: mdl-35921787

RESUMO

Thirteen undescribed diterpenoids, including an ent-isopimarane (1), ten ent-atisanes (2-8 and 15-17), and two ingenanes (20 and 21) and ten known compounds, were separated from the whole plant of E. wallichii. The structures and absolute stereochemistry of these compounds were delineated by 1D and 2D NMR, mass spectrometry, pyridine-induced solvent shifts, and X-ray diffraction analyses. Euphwanoid A (1) is elucidated as an ent-16­norisopimarane type diterpenoid featuring a C-8-O-C-15 lactone fragment. And euphwanoid B (2) represents a rare ent-atisane type tetranorditerpene possessing a tetrahydrofuran moiety. In addition, all these isolated compounds were assayed for their protective effects on H2O2-induced BV-2 microglial cells damage. And representative compound 1 could protect BV-2 cells against oxidative damage via the NRF2/HO-1 signaling pathway.


Assuntos
Diterpenos , Euphorbia , Diterpenos/química , Diterpenos/farmacologia , Euphorbia/química , Peróxido de Hidrogênio/farmacologia , Microglia , Estrutura Molecular
16.
Bioorg Chem ; 128: 106103, 2022 11.
Artigo em Inglês | MEDLINE | ID: mdl-35998520

RESUMO

Tigliane and rhamnofolane diterpenoids bearing glycosyl substituents are rarely found in nature. In the current study, seven new tigliane glycosides, euphorwallsides A - G (1-7), and five new rhamnofolane glycosides, euphorwallsides H - L (8-12), were isolated from the whole plants of Euphorbia wallichii. Their structures were elucidated by a combination of spectroscopic, computational, and chemical means. The aglycones of 1-5 represent a rare class of 13-deoxygenated tiglianes, while those of 8-12 represent the first examples of 4-deoxygenated rhamnofolanes. 2, 3, 5, 7, 8, and 12 showed significant neuroprotective effects on sodium nitroprusside (SNP)-induced neuronal death in pheochromocytoma cell line PC-12 at 10 µM, being more active than the clinical drug, edaravone. Mechanistic study revealed that the most active compound, 3, could inhibit reactive oxygen species (ROS) accumulation and restore the mitochondrial membrane potential via modulating the Nrf2 signaling pathway in PC-12 cells.


Assuntos
Euphorbia , Forbóis , Animais , Euphorbia/química , Glicosídeos/farmacologia , Estrutura Molecular , Estresse Oxidativo , Células PC12 , Ratos
17.
Phytochemistry ; 203: 113372, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-35964805

RESUMO

Nine previously undescribed diterpenoids, euphorfiatnoids A-I, together with seven known diterpenoids, were isolated from the roots of wild Euphorbia fischeriana. Their structures were elucidated by the interpretation of HRESIMS, UV, and NMR data. Their configurations were determined by electronic circular dichroism (ECD) spectroscopy analysis and the structure of euphorfiatnoid A was confirmed by X-ray crystallography. To further understand the antitumor effects of E. fischeriana, we tested the cytotoxicity of these compounds against H460, HepG2, and MCF-7 cell lines in vitro using MTT assays. Euphorfiatnoid B exhibited the most promising inhibitory effect against H460 cells with an IC50 value of 9.97 µM. Euphorfiatnoid A and C also exhibited moderate cytotoxicity against HepG2 cells with IC50 values of 11.64 and 13.10 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos , Antineoplásicos , Diterpenos , Euphorbia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Diterpenos/química , Euphorbia/química , Humanos , Células MCF-7 , Estrutura Molecular , Raízes de Plantas/química
18.
Braz J Biol ; 82: e259628, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-36000690

RESUMO

The natural phytochemical latex of Euphorbia milii var. hislopii is one of the most promising natural molluscicides for the control of Biomphalaria glabrata, and has been widely studied under laboratory conditions for selective control of schistosomiasis transmission. However, the effect of this product on B. glabrata infected by other helminths had not yet been investigated. The present study reports evaluation of the effect of E. milii var. hislopii latex on the survival and reproductive activity of B. glabrata infected by Angiostrongylus cantonensis. For this purpose, the following groups were formed: control (C), exposed (E), infected (I) and infected and exposed for different time intervals (1 day - I+E-1D, 7 days - I+E-7D, 14 days - I+E-14D, 21 days - I+E-21D and 28 days - I+E-28D). The experimental infection was performed with L1 larvae of A. cantonensis and exposure to 0.08 mg/L (LC50) of E. milii latex for a period of 24 hours. We analyzed the effects of E. milii latex on the survival of snails during four weeks, reproductive parameters and possible histophysiopathological changes in the gonad and albumen gland of the snails. Regarding survival, there was reduction of more than 50% in the groups exposed to latex (E and I + E) compared to the control group. As for the number of ovigerous masses, eggs, and average number of hatched snails, significant increases were observed in the I+E-1D group at the 4th week compared to the control group and the other weeks in the same group. Angiostrongylus cantonensis larvae were observed in the gonad and albumen gland from day 21 and 28 of infection in groups I and I+E, respectively, with granuloma-like formation. At these observation periods and in these groups, an increase in galactogen was observed in the albumen gland, which influenced egg laying, suggesting the existence of a fecundity compensation mechanism phenomenon. It was possible to conclude that both stressors - A. cantonensis infection and exposure to E. milii latex - directly influenced the survival and reproductive parameters of B. glabrata.


Assuntos
Angiostrongylus cantonensis , Biomphalaria , Euphorbia , Esquistossomose , Animais , Biomphalaria/parasitologia , Látex/farmacologia , Esquistossomose/prevenção & controle
19.
Phytochemistry ; 203: 113382, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36007663

RESUMO

The phytochemical study on Euphorbia fischeriana, a folk medicinal plant in China, led to the isolation of eight undescribed glycosides, including two diterpene glycosides, three acetophenone glycosides and three tannins together with eight known ones. Their planar structures were elucidated by extensive analyses of 1D, 2D NMR experiments and HRESIMS. The absolute configurations were determined by NOESY experiments, ECD calculations. All undescribed compounds were evaluated for their cytotoxicity and antibacterial activities in vitro. Two diterpene glycosides (1-2) showed cytotoxic activity with IC50 values ranging from 5.4 to 16.2 µM toward Hep-G2, Hep-3B, A549, NCI-H460 and AGS cells. Tannins (6-8) showed the significant antibacterial activity with MIC values in the range of 1.56-6.25 µg/mL.


Assuntos
Antineoplásicos Fitogênicos , Diterpenos , Euphorbia , Acetofenonas/farmacologia , Antibacterianos/farmacologia , Antineoplásicos Fitogênicos/química , Diterpenos/química , Euphorbia/química , Glicosídeos/análise , Glicosídeos/farmacologia , Estrutura Molecular , Compostos Fitoquímicos/análise , Extratos Vegetais/química , Raízes de Plantas/química , Taninos/análise
20.
Molecules ; 27(16)2022 Aug 16.
Artigo em Inglês | MEDLINE | ID: mdl-36014466

RESUMO

Euphorbia resinifera latex has been extensively utilized in traditional medicine due to its range of bioactivities. Chromatographic separations on silica gel of ethanol extract of E. resinifera latex led to the development of a new procedure for isolating resiniferatoxin (4) via dried E. resinifera latex and the identification of nine compounds. Among these, catechol (7), protocatechuic acid (8) and 3,4-dihydroxyphenylacetic acid (9), known phenolic compounds, were identified for the first time in E. resinifera latex. Herein we investigated the effects of major compounds of the latex of E. resinifera on the yeast Saccharomyces cerevisiae, on the growth of Aspergillus carbonarius, a widespread fungal contaminant, and on the breast cancer cell line MCF7 as well as on MCF10A normal breast cells. 12-deoxyphorbol-13-isobutyrate-20-acetate (2) had an inhibiting effect on the growth of A. carbonarius, and 7-p-metoxyphenylacetate-3,8,12-triacetate ingol (3) showed a negative effect on yeast cell growth and also a cytotoxic effect on breast cancer cell line MCF7, but not on MCF10A cells. Deglucosyl euphorbioside A (5) and euphorbioside A (6) showed a discoloration effect that was possibly related to mitochondrial functionality in yeast, and also cytotoxicity only on the cancer cell line that was tested. Interestingly, treatment of MCF7 cells with 7-p-metoxyphenylacetate-3,8,12-triacetate ingol (3) and deglucosyl euphorbioside A (5) not only led to a specific cytotoxic effect but also to the increase in the level of intracellular ROS.


Assuntos
Antineoplásicos , Neoplasias da Mama , Diterpenos , Euphorbia , Antifúngicos , Antineoplásicos/farmacologia , Diterpenos/química , Euphorbia/química , Feminino , Humanos , Látex/química , Saccharomyces cerevisiae
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