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1.
Artif Cells Nanomed Biotechnol ; 52(1): 261-269, 2024 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-38696143

RESUMO

The widespread dissemination of bacterial resistance has led to great attention being paid to finding substitutes for traditionally used antibiotics. Plants are rich in various phytochemicals that could be used as antibacterial therapies. Here, we elucidate the phytochemical profile of Euphorbia canariensis ethanol extract (EMEE) and then elucidate the antibacterial potential of ECEE against Pseudomonas aeruginosa clinical isolates. ECEE showed minimum inhibitory concentrations ranging from 128 to 512 µg/mL. The impact of ECEE on the biofilm-forming ability of the tested isolates was elucidated using crystal violet assay and qRT-PCR to study its effect on the gene expression level. ECEE exhibited antibiofilm potential, which resulted in a downregulation of the expression of the biofilm genes (algD, pelF, and pslD) in 39.13% of the tested isolates. The antibacterial potential of ECEE was studied in vivo using a lung infection model in mice. A remarkable improvement was observed in the ECEE-treated group, as revealed by the histological and immunohistochemical studies. Also, ELISA showed a noticeable decrease in the oxidative stress markers (nitric oxide and malondialdehyde). The gene expression of the proinflammatory marker (interleukin-6) was downregulated, while the anti-inflammatory biomarker was upregulated (interleukin-10). Thus, clinical trials should be performed soon to explore the potential antibacterial activity of ECEE, which could help in our battle against resistant pathogenic bacteria.


Assuntos
Antibacterianos , Euphorbia , Extratos Vegetais , Pseudomonas aeruginosa , Infecções Respiratórias , Pseudomonas aeruginosa/efeitos dos fármacos , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antibacterianos/uso terapêutico , Euphorbia/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Infecções Respiratórias/tratamento farmacológico , Animais , Camundongos , Estresse Oxidativo/efeitos dos fármacos , Carga Bacteriana/efeitos dos fármacos , Regulação Bacteriana da Expressão Gênica/efeitos dos fármacos
2.
Medicine (Baltimore) ; 103(18): e38039, 2024 May 03.
Artigo em Inglês | MEDLINE | ID: mdl-38701291

RESUMO

As a result of increasing drug resistance, crossover resistance development, prolonged therapy, and the absence of different agents with innovative methods for implementation, the efficacy of recent antileishmanial medications is severely declining. So, it is vital to look for other medications from botanical remedies that have antileishmanial activity. The latex of Euphorbia abyssinica (E abyssinica) and the leaves of Clematis simensis fresen (C simensis) were macerated in methanol (80%). In vitro antileishmanial activity of the preparation was tried on promastigotes of Leishmania aethiopica (L aethiopica) and Leishmania donovani (L donovani) using resazurin assay, and fluorescence intensity was measured. One percent of dimethyl sulfoxide (DMSO) and media as negative control and amphotericin B as positive control were used. Additionally, hemolytic & phytochemical tests of the preparation were done. The mean and standard errors of each extract were evaluated and interpreted for statistical significance using one-way analysis of variance. From sigmoidal dose-response curves of % inhibition, half maximal inhibitory concentration (IC50) values were determined by GraphPad Prism and Microsoft Excel; outcomes were presented as mean ±â€…standard error of mean of triplicate trials. P < .05 was statistical significance. The phytochemical screening of C simensis and E abyssinica confirmed the existence of steroids, phenols, tannins, saponins, alkaloids, terpenoids, flavonoids and glycosides. C simensis possesses antileishmanial activity with IC50 outcomes of 46.12 ±â€…0.03 and 8.18 ±â€…0.10 µg/mL on the promastigotes of L aethiopica and L donovani, respectively. However, E abyssinica showed stronger activity with IC50 outcomes of 16.07 ±â€…0.05 µg/mL and 4.82 ±â€…0.07 µg/mL on L aethiopica and L donovani, respectively. C simensis and E abyssinica have a less hemolytic effect on human red blood cells at low concentrations. The outcomes from this investigation demonstrated that the preparation of C simensis and E abyssinica indicated significant antileishmanial activity. Therefore, further in vivo assessment of antileishmanial, cytotoxicity activity and quantitative identification of secondary metabolites are highly recommended.


Assuntos
Antiprotozoários , Euphorbia , Látex , Extratos Vegetais , Folhas de Planta , Extratos Vegetais/farmacologia , Euphorbia/química , Látex/farmacologia , Látex/química , Antiprotozoários/farmacologia , Folhas de Planta/química , Humanos , Leishmania donovani/efeitos dos fármacos , Concentração Inibidora 50 , Leishmania/efeitos dos fármacos , Metanol , Solventes , Hemólise/efeitos dos fármacos
3.
Med Oncol ; 41(6): 152, 2024 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-38743193

RESUMO

Metastasis is the most devastating attribute of breast cancer (BC) that leads to high mortality. It is a complex process of tumor cell migration, invasion, and angiogenesis. In this study, we evaluated the effect of ERA on BC metastasis and BC progression in vivo. The transwell invasion/migration and wound healing assays showed that ERA treatment significantly reduced the invasion and migration of BC cell lines. The expression of mesenchymal (E-cadherin and N-cadherin), matrix metalloproteinases (MMP2, MMP9), and stemness markers (Oct3) were down-regulated by ERA. Furthermore, ERA down-regulated angiogenic chemokines (CXCL1/2/3, CXCL5, and CXCL12) expression in the highly metastatic MDA-MB-231 cell line. The clonogenic survival of BC cells was also reduced by ERA treatment. Strikingly, ERA prevented DMBA-induced tumor growth in Swiss albino mice as depicted by a high animal survival rate (84%) in the ERA group and histopathological analysis. Conclusively, this study revealed that ERA possesses anti-metastatic potential and also reduces the growth of BC in vivo. Moreover, the GC-MS data revealed the presence of biologically active compounds (Lupeol, Phytol, phytosterol) and some rare (9, 19-Cyclolanost) phyto metabolites in ERA extract. However, further studies are suggestive to identify and isolate the therapeutic agents from ERA to combat BC and metastasis.


Assuntos
Neoplasias da Mama , Euphorbia , Extratos Vegetais , Animais , Feminino , Neoplasias da Mama/patologia , Neoplasias da Mama/tratamento farmacológico , Camundongos , Humanos , Extratos Vegetais/farmacologia , Euphorbia/química , Linhagem Celular Tumoral , Movimento Celular/efeitos dos fármacos , Metástase Neoplásica , Progressão da Doença
4.
J Environ Manage ; 357: 120835, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38581897

RESUMO

Euphorbia Rigida (E. Rigida), a lignocellulosic biomass with low ash content, is a suitable feedstock for pyrolysis. This work investigated the physicochemical characteristics and thermokinetic analysis of E. Rigida pyrolysis by using isoconversional and master plots methods. Ultimate and proximate analyses and oxygen bomb calorimeter were used to determine the physicochemical parameters. The activation energies were calculated using model-free methods (KAS, Friedman and Starink) and were found as 184, 178 and 185 kJ/mol, respectively. Using Fraser-Suzuki deconvolution, pseudo-components were also calculated and the active pyrolysis region was divided into three zones. The master plots showed that reaction order mechanisms (Fn) were effective in Zone I, and diffusion mechanisms (Dn) were well matched in Zone II and Zone III. The thermodynamic parameters (ΔH, ΔG and ΔS) were calculated and according to these results, E. Rigida pyrolysis was an endothermic and non-spontaneous process.


Assuntos
Euphorbia , Pirólise , Espectroscopia de Infravermelho com Transformada de Fourier , Termogravimetria , Termodinâmica , Cinética , Biomassa
5.
Langmuir ; 40(19): 10313-10325, 2024 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-38683169

RESUMO

Over an extended period of evolution and natural selection, a multitude of species developed a diverse array of biological interface features with specific functions. These biological structures provide a rich source of inspiration for the design of bionic structures on superhydrophobic surfaces. Understanding the functional mechanism of plant leaves is of paramount importance for the advancement of new engineering materials and the further promotion of engineering applications of bionic research. The hierarchical structure of microcrater-covered nanograss (MCNG) on the surface of E. helioscopia L. leaf provided the inspiration for the bionic MCNG surface, which was successfully prepared on a copper substrate by hybrid laser micromachining technology and chemical etching. The combined action of texture structure and surface chemistry resulted in a contact angle of 169° ± 1° for MCNG surface droplets and a rolling angle of less than 1°. Notably, the condensation-induced adhesion force does not augment with the increase of the temperature difference, which facilitated the shedding of hot droplets from the surface. The microscope observation revealed a high density of condensed droplets on the MCNG surface and the tangible jumping behavior of the droplets. The fabricated MCNG also demonstrated excellent antifrost/anti-icing abilities in low-temperature and high-humidity environments. Finally, the study confirmed the exceptional mechanical durability and reusability of the MCNG surface through various tests, including scratch damage, sandpaper wear, water flow impact and flushing, and condensation-drying cycle tests. The nanograss can be effectively protected within the microcrater structure. This research presents a promising approach for preventing and/or removing unwanted droplets in numerous engineering applications.


Assuntos
Euphorbia , Folhas de Planta , Propriedades de Superfície , Euphorbia/química , Folhas de Planta/química , Nanoestruturas/química , Interações Hidrofóbicas e Hidrofílicas , Tamanho da Partícula
6.
J Agric Food Chem ; 72(17): 9746-9754, 2024 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-38602331

RESUMO

The latex of Euphorbia peplus and its major component 20-deoxyingenol-3-angelate (DI3A) displayed significant nematicidal activity against Caenorhabditis elegans and Panagrellus redivivus. DI3A treatment inhibited the growth and development of nematodes and caused significantly negative effects on locomotion behavior, reproduction, and accumulation of reactive oxygen species. Transcriptome analysis indicated that differential expression genes in DI3A-treated C. elegans were mainly associated with the metabolism, growth, and development process, which were further confirmed by RT-qPCR experiments. The expression level of TPA-1 gene encoding a protein kinase C isotype was obviously upregulated by DI3A treatment, and knockdown of TPA-1 by RNAi technology in the nematode could relieve the growth-inhibitory effect of DI3A. Metabolic analysis indicated that DI3A was hardly metabolized by C. elegans, but a glycosylated indole derivative was specifically accumulated likely due to the activation of detoxification. Overall, our findings suggested that DI3A from E. peplus latex exerted a potent nematicidal effect through the gene TPA-1, which provides a potential target for the control of nematodes and also suggests the potential application value of E. peplus latex and DI3A as botanical nematicides.


Assuntos
Antinematódeos , Caenorhabditis elegans , Euphorbia , Látex , Proteína Quinase C , Animais , Caenorhabditis elegans/efeitos dos fármacos , Caenorhabditis elegans/genética , Caenorhabditis elegans/enzimologia , Caenorhabditis elegans/metabolismo , Caenorhabditis elegans/crescimento & desenvolvimento , Látex/química , Látex/metabolismo , Antinematódeos/farmacologia , Antinematódeos/química , Antinematódeos/metabolismo , Euphorbia/química , Proteína Quinase C/metabolismo , Proteína Quinase C/genética , Extratos Vegetais/farmacologia , Extratos Vegetais/química
7.
Bioorg Chem ; 147: 107377, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38653150

RESUMO

The first systematic acylated diversification of naturally scarce premyrsinane diterpenes, together with their biosynthetic precursors lathyrane diterpene were carried out. Two new series of premyrsinane derivates (1a-32a) and lathyrane derivates (1-32) were synthesized from the naturally abundant lathyrane diterpene Euphorbia factor L3 through a bioinspired approach. The cholinesterase inhibitory and neuroprotective activities of these diterpenes were investigated to explore potential anti-Alzheimer's disease (AD) bioactive lead compounds. In general, the lathyrane diterpenes showed the better acetylcholinesterase (AChE) inhibitory activity than that of premyrsinanes. The lathyrane derivative 17 bearing a 3-dimethylaminobenzoyl moiety showed the best AChE inhibition effect with the IC50 value of 7.1 µM. Molecular docking demonstrated that 17 could bond with AChE well (-8 kal/mol). On the other hand, premyrsinanes showed a better neuroprotection profile against H2O2-induced injury in SH-SY5Y cells. Among them, the premyrsinane diterpene 16a had significant neuroprotective effect with the cell viability rate of 113.5 % at 12.5 µM (the model group with 51.2 %). The immunofluorescence, western blot and reactive oxygen species (ROS) analysis were conducted to demonstrate the mechanism of 16a. Furthermore, a preliminary SAR analysis of the two categories of diterpenes was performed to provide the insights for anti-AD drug development.


Assuntos
Acetilcolinesterase , Doença de Alzheimer , Inibidores da Colinesterase , Diterpenos , Euphorbia , Fármacos Neuroprotetores , Diterpenos/farmacologia , Diterpenos/química , Diterpenos/síntese química , Doença de Alzheimer/tratamento farmacológico , Inibidores da Colinesterase/farmacologia , Inibidores da Colinesterase/síntese química , Inibidores da Colinesterase/química , Fármacos Neuroprotetores/farmacologia , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/síntese química , Euphorbia/química , Humanos , Acetilcolinesterase/metabolismo , Relação Estrutura-Atividade , Estrutura Molecular , Simulação de Acoplamento Molecular , Relação Dose-Resposta a Droga , Sobrevivência Celular/efeitos dos fármacos
8.
Bol. latinoam. Caribe plantas med. aromát ; 23(2): 160-179, mar. 2024. ilus, tab, graf
Artigo em Inglês | LILACS | ID: biblio-1538275

RESUMO

The present review was aimed at documenting medicinal uses of species of the Euphorbiaceae family in Zimbabwe. Literature was collected from online databases such as BioMed Central, W eb of Science, Springerlink, Google Scholar, Scielo, PubMed, Science Direct, ACS Publications, Scopus and JSTOR. This study showed that 29 species are used to manage human and animal diseases in Zimbabwe. These species are used against 49 medical condition s, mainly as ethnoveterinary medicine (21 use reports), and traditional medicine against respiratory (23 use reports), gastro - intestinal (14 use reports), male reproductive (11 use reports), antenatal and postpartum (10 use reports each) and sexually trans mitted infections (9 use reports). Acalypha brachiata , Bridelia cathartica , B. mollis , Croton megalobotrys , Euphorbia ingens , E. matabelensis , Flueggea virosa , Monadenium lugardiae , Pseudolachnostylis maprouneifolia , Ricinus communis and Spirostachys afric ana have the highest number of medicinal uses. There is need to unravel the therapeutic potential of the family through further ethnopharmacological research.


La p resente revisión tuvo como objetivo documentar los usos medicinales de especies de la familia Euphorbiaceae en Zimbabwe. La literatura se recopiló de bases de datos en línea como BioMed Central, Web of Science, Springerlink, Google Scholar, Scielo, PubMed, Science Direct, ACS Publications, Scopus y JSTOR. Este estudio mostró que se utilizan 29 especies para el tratamiento de enfermedades humanas y animales en Zimbabwe. Estas especies se utilizan para tratar 49 condiciones médicas, principalmente como medici na etnoveterinaria (21 informes de uso), y medicina tradicional para enfermedades respiratorias (23 informes de uso), gastrointestinales (14 informes de uso), reproductivas masculinas (11 informes de uso), prenatales y posparto (10 informes de uso cada una ) e infecciones de transmisión sexual (9 informes de uso). Acalypha brachiata , Bridelia cathartica , B. mollis , Croton megalobotrys , Euphorbia ingens , E. matabelensis , Flueggea virosa , Monadenium lugardiae , Pseudolachnostylis maprouneifolia , Ricinus communi s y Spirostachys africana son las especies con mayor número de usos medicinales. Es necesario desvelar el potencial terapéutico de esta familia a través de futuras investigaciones etnofarmacológicas.


Assuntos
Plantas Medicinais , Euphorbia , Zimbábue , Etnobotânica
9.
Molecules ; 29(5)2024 Feb 29.
Artigo em Inglês | MEDLINE | ID: mdl-38474596

RESUMO

Euphorbia is a large genus of the Euphorbiaceae family. Around 250 species of the Euphorbia genus have been studied chemically and pharmacologically; different compounds have been isolated from these species, especially diterpenes and triterpenes. Several reports show that several species have anti-inflammatory activity, which can be attributed to the presence of diterpenes, such as abietanes, ingenanes, and lathyranes. In addition, it was found that some diterpenes isolated from different Euphorbia species have anti-cancer activity. In this review, we included compounds isolated from species of the Euphorbia genus with anti-inflammatory or cytotoxic effects published from 2018 to September 2023. The databases used for this review were Science Direct, Scopus, PubMed, Springer, and Google Scholar, using the keywords Euphorbia with anti-inflammatory or cytotoxic activity. In this review, 68 studies were collected and analyzed regarding the anti-inflammatory and anti-cancer activities of 264 compounds obtained from 36 species of the Euphorbia genus. The compounds included in this review are terpenes (95%), of which 68% are diterpenes, especially of the types ingenanes, abietanes, and triterpenes (approximately 15%).


Assuntos
Antineoplásicos , Diterpenos , Euphorbia , Triterpenos , Euphorbia/química , Abietanos , Estrutura Molecular , Diterpenos/química , Triterpenos/química , Anti-Inflamatórios
10.
Bioorg Chem ; 145: 107253, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38452588

RESUMO

Phytochemical study on Euphorbia milii, a common ornamental plant, resulted in the identification of thirteen new ent-rosane diterpenoids (1-13), three new ent-atisane diterpenoids (14-16), and a known ent-rosane (17). Their structures were delineated using spectroscopic data, quantum chemical calculations, and X-ray diffraction experiments. Euphomilone F (1) represented a rare ent-rosane-type diterpenoid with a 5/7/6 skeleton. Euphoainoid G (8) was a rare rosane diterpenic acid. Compounds 9 and 10 carried infrequent tetrahydrofuran rings, and compounds 11-13 was 18-nor-ent-rosane diterpenoids. All isolates were evaluated for their inhibitory effects on RANKL-induced osteoclasts. Notably, compounds with aromatic ester groups (2-7) showed promising activities (IC50 < 10 µM), underscoring the significance of acylated A-ring moieties in the ent-rosane skeleton for anti-osteoclastogenesis. Thirteen synthetic derivatives were obtained through esterification of 17. Of these, compound 27 exhibited remarkable improvement, with an IC50 of 0.8 µM, more than a 12-fold increase in potency compared to the parent compound 17 (IC50 > 10 µM). This work presents a series of new ent-rosane diterpenoids with potential antiosteoporosis agents.


Assuntos
Diterpenos , Euphorbia , Osteogênese , Euphorbia/química , Extratos Vegetais/química , Osteoclastos , Diterpenos/farmacologia , Diterpenos/química , Estrutura Molecular
11.
Plant Biol (Stuttg) ; 26(3): 398-414, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38444147

RESUMO

Euphorbia canariensis is an iconic endemic species representative of the lowland xerophytic communities of the Canary Islands. It is widely distributed in the archipelago despite having diasporas unspecialized for long-distance dispersal. Here, we reconstructed the evolutionary history of E. canariensis at two levels: a time-calibrated phylogenetic analysis aimed at clarifying interspecific relationships and large-scale biogeographic patterns; and a phylogeographic study focused on the history of colonization across the Canary Islands. For the phylogenetic study, we sequenced the ITS region for E. canariensis and related species of Euphorbia sect. Euphorbia. For the phylogeographic study, we sequenced two cpDNA regions for 28 populations representing the distribution range of E. canariensis. The number of inter-island colonization events was explored using PAICE, a recently developed method that includes a sample size correction. Additionally, we used species distribution modelling (SDM) to evaluate environmental suitability for E. canariensis through time. Phylogenetic results supported a close relationship between E. canariensis and certain Southeast Asian species (E. epiphylloides, E. lacei, E. sessiliflora). In the Canaries, E. canariensis displayed a west-to-east colonization pattern, not conforming to the "progression rule", i.e. the concordance between phylogeographic patterns and island emergence times. We estimated between 20 and 50 inter-island colonization events, all of them in the Quaternary, and SDM suggested a late Quaternary increase in environmental suitability for E. canariensis. The extreme biogeographic disjunction between Macaronesia and Southeast Asia (ca. 11,000 km) parallels that found in a few other genera (Pinus, Dracaena). We hypothesize that these disjunctions are better explained by extinction across north Africa and southwest Asia rather than long-distance dispersal. The relatively low number of inter-island colonization events across the Canaries is congruent with the low dispersal capabilities of E. canariensis.


Assuntos
Euphorbia , População Europeia , Filogeografia , Filogenia , Euphorbia/genética , Evolução Biológica
12.
Sci Rep ; 14(1): 5627, 2024 03 07.
Artigo em Inglês | MEDLINE | ID: mdl-38454096

RESUMO

Plant extracts are actively being used worldwide due to the presence of biologically active constituents helping in the preservation of food, and to aid against various diseases owing to their antimicrobial and antioxidant potential. The present research work was carried out to investigate the phytochemical constituents, antimicrobial activity, and antioxidant activity of different extracted samples of Euphorbia parviflora. Anti-microbial studies were carried out by Agar well diffusion while the DPPH method was employed for investigating anti-oxidant activity. Three samples from methanol, chloroform, and ethyl acetate extract were tested against five different bacterial strains comprising two species from Gram-negative bacteria i.e., Staphylococcus aureus and Bacillus subtilis and three species from Gram-positive bacteria i.e. Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumonia along two fungal strains i.e. Candida albicans and Aspergillus niger. The results of the qualitative phytochemical analysis showed that methanolic, chloroformic, and ethylacetate extract of Euphorbia parviflora consist of alkaloids, reducing sugars, flavonoids, terpenoids, tannins, and saponins. The total phenol and flavonoid content of E. parviflora showed that the methanolic extract of E. parviflora had a significantly higher total phenolic content (53.73 ± 0.30 mg of GAE/g) and flavonoid content (44.62 ± 0.38 mg of than other extracts. The content of total phenolic and flavonoids was more in methanolic extract as compared to other extracts of E. prolifera. The HPLC analysis showed that in the chloroform extract of E. parviflora Cinnamic acid (4.32 ± 2.89 mg/g) was dominant, in methanol extract quercetin (3.42 ± 2.89 mg/g) was dominant and in ethyl acetate extract of E. parviflora catechin (4.44 ± 2.89 mg/g) was found dominant. The antimicrobial activity revealed that amongst all the extracts the highest antibacterial activity was shown by methanolic extract against B. subtilis and Staphylococcus aureus as compared to the other extracts. The antioxidant activity revealed that methanolic extract of E. parviflora demonstrated higher antioxidant activity (82.42 ± 0.02) followed by chloroform extract (76.48 ± 0.08) at 150 µg/mL. The aim of this study was primarily to evaluate the potential of this plant as a reliable source of antimicrobials and antioxidants that may be used for the treatment of various infectious diseases in the future. The study provides evidence that this plant can act as a reliable source of antimicrobial and antioxidant agents and might be used against several infectious diseases.


Assuntos
Acetatos , Anti-Infecciosos , Doenças Transmissíveis , Euphorbia , Euphorbiaceae , Antioxidantes/farmacologia , Antioxidantes/química , Metanol/química , Clorofórmio , Cromatografia Líquida de Alta Pressão , Anti-Infecciosos/farmacologia , Antibacterianos/farmacologia , Antibacterianos/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/química , Flavonoides/análise , Fenóis/análise , Testes de Sensibilidade Microbiana
13.
Bioorg Chem ; 145: 107194, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38367429

RESUMO

Phytochemical investigation into the medium polar fraction of the ethanol extract of Euphorbia peplus led to the identification of 32 diterpenoids with five structural types. Compounds 1-5 and 7-11 are reported for the first time, while the configuration of 6,7-epoxy group of 6 was revised to be ß-oriented. Compounds 1-5 feature a rare structural variation of the double bond at Δ1 migrating to Δ1(10) in the tigliane-type diterpenoid family. Biologically, compound 21 was found to be the only one to show moderate cytotoxic activity, associated with the presence of a benzoyloxy residue at C-16. Besides, compounds 4, 8, 12, 13, 16, and 19 show significant inhibitory activities against NO production induced by LPS in RAW264.7 macrophage cells, with IC50 values within 2-5 µM. Structure-activity relationship (SAR) analysis revealed that the ingenane-type diterpenoids have the best anti-inflammatory activity, and the esterification at 3-OH or 5-OH is crucial. Further biological researches demonstrated that 13, the predominant metabolite in this plant, exerts anti-inflammatory effects by blocking the activation of NF-κB and MAPK signaling pathways.


Assuntos
Antineoplásicos , Diterpenos , Euphorbia , Diterpenos/farmacologia , Diterpenos/química , Relação Estrutura-Atividade , Euphorbia/química , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Antineoplásicos/farmacologia , Estrutura Molecular
14.
Phytochemistry ; 221: 114043, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38417720

RESUMO

Chemical investigation of Euphorbia wallichii Hook. f. led to the isolation of four undescribed rearranged diterpenoids, euphwanoids I-IV (1-4), and six unreported tigliane diterpenoids walliglianes A-F (5-10). Euphwanoids I-III (1-3) possess a rare 6/6/7/3 ring scaffold, euphwanoid IV (4) is the first spiro[tricyclo[5.4.0.02,4]undecane-8,1'-cyclopentane] skeleton to be found in the tigliane family. The structures of compounds 1-10 were established by utilizing spectroscopic data analysis, experimental electronic circular dichroism measurements, 13C NMR calculations, and single-crystal X-ray diffraction. In the preliminary bioassay, compounds 3, 4, and 7 were found to protect BV-2 cells against H2O2-induced cell injury in a dose-dependent manner by the CCK8 assay.


Assuntos
Diterpenos , Euphorbia , Forbóis , Euphorbia/química , Antioxidantes/farmacologia , Peróxido de Hidrogênio/farmacologia , Estrutura Molecular , Diterpenos/farmacologia , Diterpenos/química
15.
Fitoterapia ; 174: 105854, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38331050

RESUMO

The chemical transformation of lathyrane nucleus through reduction and oxidation reactions using Euphorbia Factor L1 (EFL1) and Euphorbia Factor L1 (EFL3) as examples were investigated, along with a co-modification strategy of lathyrane nucleus and its side ester chain. A total of 38 lathyrane derivatives (5-42) including 34 new compounds were obtained, which greatly enriched the structural diversity of the lathyrane-type diterpenoids. Cytotoxicity against drug-sensitive and drug (adriamycin, ADM) resistant MCF-7 cells showed that 23 out of 38 transformed derivatives possessed obvious cytotoxic activity with IC50 values ranging from 7.0 to 41.1 µM and 3.2 to 45.5 µM, respectively, against both cells, compared to the noncytotoxic EFL1 and EFL3. The multidrug resistance (MDR) reversing activities of these lathyrane derivatives were further evaluated in MCF-7/ADM. Three transformed compounds (reversal fold, RF = 151.33, 62.94 and 47.3 for 27, 37 and 42) showed markedly higher activity than EFL1 (RF = 32.92) and EFL3 (RF = 39.68). Structure-activity relationship study revealed an essential role of C-6/17 and C-12/13 double bonds on lathyrane nucleus for exerting MDR reversal activity. Western blotting analysis showed that 42 could reduce the expression level of P-glycoprotein (P-gp) in MCF-7/ADM cells; however, the most active compound 27 with an unnatural 5/7/7/4 fused-ring diterpenoid skeleton, had no inhibitory effect on P-gp expression.


Assuntos
Diterpenos , Euphorbia , Fenilpropionatos , Estrutura Molecular , Euphorbia/química , Resistência a Múltiplos Medicamentos , Diterpenos/farmacologia , Diterpenos/química , Membro 1 da Subfamília B de Cassetes de Ligação de ATP/metabolismo , Membro 1 da Subfamília B de Cassetes de Ligação de ATP/farmacologia , Subfamília B de Transportador de Cassetes de Ligação de ATP
16.
Phytochemistry ; 220: 113996, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38311150

RESUMO

The study entailed the investigation of the roots of Euphorbia wallichii, which resulted in the isolation of 29 ent-atisane diterpenoids (1-29), 14 of which were previously unknown. These previously undescribed ones were named euphorwanoids A-N (3-5, 7, 9, and 10-18). Various techniques, including comprehensive spectroscopic methods and calculated electronic circular dichroism, were employed to determine their molecular structures. Additionally, the absolute configurations of ten ent-atisane diterpenoids (1, 2, 5, 6, 8, 9, 11, 12, 14 and 16) were established through X-ray crystallographic analyses. All isolated compounds' potential to inhibit the influenza A virus in vitro were evaluated. Compounds 18, 20, and 24 exhibited notable antiviral activity against the A/Puerto Rico/8/1934 strain. Their effective concentrations for reducing viral activity (EC50 values) were found to be 8.56, 1.22, and 4.97 µM, respectively. An intriguing aspect of this research is that it marks the first instance of ent-atisane diterpenes displaying anti-H1N1 activity. Empirical NMR rules were established with Δδ to distinguish the R/S configurations of C-13 and C-16 in ent-atisanes.


Assuntos
Diterpenos , Euphorbia , Euphorbia/química , Estrutura Molecular , Diterpenos/química , Dicroísmo Circular , Espectroscopia de Ressonância Magnética
17.
Int J Mol Sci ; 25(2)2024 Jan 08.
Artigo em Inglês | MEDLINE | ID: mdl-38255854

RESUMO

Flavonoids are ubiquitous polyphenolic compounds that play a vital role in plants' defense response and medicinal efficacy. UV-B radiation is a vital environmental regulator governing flavonoid biosynthesis in plants. Many plants rapidly biosynthesize flavonoids as a response to UV-B stress conditions. Here, we investigated the effects of flavonoid biosynthesis via UV-B irradiation in Euphorbia lathyris. We found that exposure of the E. lathyris callus to UV-B radiation sharply increased the level of one O-methyltransferase (ElOMT1) transcript and led to the biosynthesis of several methylated flavonoids. The methyltransferase ElOMT1 was expressed heterologously in E. coli, and we tested the catalytic activity of recombinant ElOMT1 with possible substrates, including caffeic acid, baicalin, and luteolin, in vitro. ElOMT1 could efficiently methylate when the hydroxyl groups were contained in the core nucleus of the flavonoid. This molecular characterization identifies a methyltransferase responsible for the chemical modification of the core flavonoid structure through methylation and helps reveal the mechanism of methylated flavonoid biosynthesis in Euphorbiaceae. This study identifies the O-methyltransferase that responds to UV-B irradiation and helps shed light on the mechanism of flavonoid biosynthesis in Euphorbia lathyris.


Assuntos
Euphorbia , Euphorbia/genética , Escherichia coli/genética , Flavonoides/genética , Luteolina , Metiltransferases/genética
18.
J Plant Physiol ; 293: 154184, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38295538

RESUMO

Euphorbia resinifera O. Berg is a plant endemic to the Northern and Central regions of Morocco known since the ancient Roman and Greek times for secreting a poisonous latex containing resiniferatoxin. However, E. resinifera pseudo-inflorescences called cyathia are devoid of laticifers and, therefore, do not secrete latex. Instead, they exudate nectar that local honey bees collect and craft into honey. Honey and cyathium water extracts find a broad range of applications in the traditional medicine of Northern Africa as ointments and water decoctions. Moreover, E. resinifera monofloral honey has received the Protected Geographic Indication certification for its outstanding qualities. Given the relevance of E. resinifera cyathia for bee nutrition, honey production, and the health benefit of cyathium-derived products, this study aimed to screen metabolites synthesized and accumulated in its pseudo-inflorescences. Our analyses revealed that E. resinifera cyathia accumulate primary metabolites in considerable abundance, including hexoses, amino acids and vitamins that honey bees may collect from nectar and craft into honey. Cyathia also synthesize volatile organic compounds of the class of benzenoids and terpenes, which are emitted by flowers pollinated by honey bees and bumblebees. Many specialized metabolites, including carotenoids, flavonoids, and polyamines, were also detected, which, while protecting the reproductive organs against abiotic stresses, also confer antioxidant properties to water decoctions. In conclusion, our analyses revealed that E. resinifera cyathia are a great source of antioxidant molecules and a good food source for the local foraging honeybees, revealing the central role of the flowers from this species in mediating interactions with local pollinators and the conferral of medicinal properties to plant extracts.


Assuntos
Euphorbia , Néctar de Plantas , Animais , Néctar de Plantas/análise , Néctar de Plantas/metabolismo , Euphorbia/metabolismo , Látex/análise , Látex/metabolismo , Antioxidantes/metabolismo , Flores/metabolismo , Água/metabolismo
19.
Fitoterapia ; 173: 105838, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38296165

RESUMO

Four previously unreported diterpenoids including three ent-atisanes (1-3) and one ent-abietane (4), along with one known linear triterpenoid (5) and five known diterpenoids including four myrsinanes (6-9), and one abietane (10) have been isolated from the roots of Euphorbia spinidens Bornm. ex Prokh. The structures were determined on the basis of extensive spectroscopic analyses including HR-ESI-MS, 1D and 2D NMR and comparison of the data with those reported in the literature. Antimicrobial potential of isolated compounds were also evaluated. Guionianol B (10) showed good antibacterial activity against Staphylococcus aureus and Bacillus subtilis with MIC value of 6.25 µg/mL.


Assuntos
Diterpenos , Euphorbia , Triterpenos , Abietanos/química , Estrutura Molecular , Euphorbia/química , Triterpenos/farmacologia , Diterpenos/farmacologia , Diterpenos/química , Espectroscopia de Ressonância Magnética , Raízes de Plantas/química
20.
Fitoterapia ; 173: 105821, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38211643

RESUMO

Four new diterpenoids (1-4) and four known diterpenoids (5-8) were purified from the whole plant of Euphorbia helioscopia L. Compounds 1 and 2 were jathophanes diterpenoids with a 5/12 polycyclic systems, compound 3 was rhamofolane diterpenoid with a 5/10 bicyclic skeleton and compound 4 was a rare class of euphorbia diterpenes featuring an unusual 5/10 fused ring system. Anti-inflammatory activity tests were conducted on the separated compounds, indicating that compound 4 had significant inhibitory effect on NLRP3 inflammasome with an IC50 value of 7.75 µM. Further, the inhibitory effect of 4 was determined using immunofluorescence assays.


Assuntos
Diterpenos , Euphorbia , Estrutura Molecular , Diterpenos/farmacologia , Anti-Inflamatórios/farmacologia
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