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1.
Med Oncol ; 41(6): 152, 2024 May 14.
Article in English | MEDLINE | ID: mdl-38743193

ABSTRACT

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.


Subject(s)
Breast Neoplasms , Euphorbia , Plant Extracts , Animals , Female , Breast Neoplasms/pathology , Breast Neoplasms/drug therapy , Mice , Humans , Plant Extracts/pharmacology , Euphorbia/chemistry , Cell Line, Tumor , Cell Movement/drug effects , Neoplasm Metastasis , Disease Progression
2.
Artif Cells Nanomed Biotechnol ; 52(1): 261-269, 2024 Dec.
Article in English | MEDLINE | ID: mdl-38696143

ABSTRACT

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.


Subject(s)
Anti-Bacterial Agents , Euphorbia , Plant Extracts , Pseudomonas aeruginosa , Respiratory Tract Infections , Pseudomonas aeruginosa/drug effects , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/therapeutic use , Euphorbia/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Extracts/therapeutic use , Respiratory Tract Infections/drug therapy , Animals , Mice , Oxidative Stress/drug effects , Bacterial Load/drug effects , Gene Expression Regulation, Bacterial/drug effects
3.
Zhongguo Zhong Yao Za Zhi ; 49(9): 2441-2450, 2024 May.
Article in Chinese | MEDLINE | ID: mdl-38812143

ABSTRACT

This study aims to explore the correlation between intestinal toxicity and composition changes of Euphorbia ebracteolata before and after Terminalia chebula soup(TCS) processing. Intragastric administration was performed on the whole animal model. By using fecal water content, inflammatory causes, and pathological damage of different parts of the intestinal tract of mice as indexes, the differences in intestinal toxicity of dichloromethane extraction of raw E. ebracteolata(REDE), dichloromethane extraction of TCS, and dichloromethane extraction of E. ebracteolata after simulated TCS processing(STREDE) were compared, so as to investigate the effect of TCS processing on the intestinal toxicity of E. ebracteolata. At the same time, the component databases of E. ebracteolata and T. chebula were constructed, and the composition changes of diterpenoids, tannins, and phenolic acids in the three extracted parts were analyzed by HPLC-TOF-MS. HPLC was used to compare the content of four diterpenoids including ent-11α-hydroxyabicta-8(14), 13(15)-dien-16, 12-olide(HAO), jolkinolide B(JNB), fischeria A(FA), and jolkinolide E(JNE) in the E. ebracteolata before and after processing and the residue of container wall after processing, so as to investigate the effect of TCS processing on the content and structure of the diterpenoids. The results showed that the REDE group could significantly increase the fecal water content and the release levels of TNF-α and IL-1ß from each intestinal segment, and intestinal tissue damage was accompanied by significant infiltration of inflammatory cells. However, compared with the REDE group, the intestinal tissue damage in the STREDE group was alleviated, and the infiltration of inflammatory cells decreased. The intestinal toxicity significantly decreased. Mass spectrometry analysis showed that there was no significant difference in the content of diterpenoids of REDE before and after simulated TCS processing, but a large number of tannins and phenolic acids were added. The results of HPLC showed that the content of four diterpenoids of E. ebracteo-lata decreased to varying degrees after TCS processing, ranging from-0.35% to-19.74%, and the decreased part mainly remained in the container wall, indicating that the structure of toxic diterpenoids of E. ebracteolata was not changed after TCS processing. The antagonistic effect of tannic and phenolic acids in the TCS may be the main reason for the reduced intestinal toxicity of E. ebracteolata after TCS processing. The TCS processing for E. ebracteolata is scientific.


Subject(s)
Drugs, Chinese Herbal , Euphorbia , Terminalia , Euphorbia/chemistry , Animals , Terminalia/chemistry , Mice , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/toxicity , Male , Intestines/drug effects , Intestines/chemistry , Chromatography, High Pressure Liquid , Humans
4.
Am J Bot ; 111(5): e16327, 2024 May.
Article in English | MEDLINE | ID: mdl-38725176

ABSTRACT

PREMISE: Quaternary climatic fluctuations and long-distance seed dispersal across the sea are critical factors affecting the distribution of coastal plants, but the spatiotemporal nature of population expansion and distribution change of East Asian coastal plants during this period are rarely examined. To explore this process, we investigated the genome-wide phylogenetic patterns of Euphorbia jolkinii Boiss. (Euphorbiaceae), which grows widely on littoral areas of Japan, Korea, and Taiwan. METHODS: We used plastome sequences and genome-wide single nucleotide polymorphisms in samples across the species range to reveal phylogeographic patterns and spatiotemporal distributional changes. We conducted ecological niche modeling for the present and the last glacial maximum (LGM). RESULTS: Genetic differentiation was observed between the northern and southern populations of E. jolkinii, separated by the major biogeographic boundary, the Tokara Gap. These two groups of populations differentiated during the glacial period and subsequently intermingled in the intermorainic areas of the central Ryukyu Islands after the LGM. Ecological niche models suggested that the potential range of E. jolkinii was restricted to southern Kyushu; however, it was widespread in the southern Ryukyu Islands and Taiwan during the LGM. CONCLUSIONS: This study provides evidence of genetic differentiation among coastal plant populations separated by the prominent biogeographical boundary. Although coastal plants are typically expected to maintain population connectivity through sea-drifted seed dispersal, our findings suggest that genetic differences may arise because of a combination of limited gene flow and changes in climate during the glacial period.


Subject(s)
Euphorbia , Phylogeography , Euphorbia/genetics , Euphorbia/physiology , Asia, Eastern , Phylogeny , Polymorphism, Single Nucleotide , Genetic Variation , Ecosystem
5.
J Nat Prod ; 87(5): 1479-1486, 2024 May 24.
Article in English | MEDLINE | ID: mdl-38728656

ABSTRACT

Bioinspired skeleton transformation of a tricyclic lathyrane-type Euphorbia diterpene was conducted to efficiently construct a tetracyclic tigliane diterpene on a gram scale via a key aldol condensation. The tigliane diterpene was then respectively converted into naturally rare ingenane and rhamnofolane diterpenes through a semipinacol rearrangement and a visible-light-promoted regioselective cyclopropane ring-opening reaction. This work provides a concise strategy for high-efficiency access to diverse polycyclic Euphorbia diterpene skeletons from abundant lathyrane-type natural products and paves the way for biological activity investigation of naturally rare molecules.


Subject(s)
Diterpenes , Euphorbia , Diterpenes/chemistry , Diterpenes/isolation & purification , Euphorbia/chemistry , Molecular Structure , Biomimetics , Biological Products/chemistry
6.
Medicine (Baltimore) ; 103(18): e38039, 2024 May 03.
Article in English | MEDLINE | ID: mdl-38701291

ABSTRACT

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.


Subject(s)
Antiprotozoal Agents , Euphorbia , Latex , Plant Extracts , Plant Leaves , Plant Extracts/pharmacology , Euphorbia/chemistry , Latex/pharmacology , Latex/chemistry , Antiprotozoal Agents/pharmacology , Plant Leaves/chemistry , Humans , Leishmania donovani/drug effects , Inhibitory Concentration 50 , Leishmania/drug effects , Methanol , Solvents , Hemolysis/drug effects
7.
J Environ Manage ; 357: 120835, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38581897

ABSTRACT

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.


Subject(s)
Euphorbia , Pyrolysis , Spectroscopy, Fourier Transform Infrared , Thermogravimetry , Thermodynamics , Kinetics , Biomass
8.
Langmuir ; 40(19): 10313-10325, 2024 May 14.
Article in English | MEDLINE | ID: mdl-38683169

ABSTRACT

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.


Subject(s)
Euphorbia , Plant Leaves , Surface Properties , Euphorbia/chemistry , Plant Leaves/chemistry , Nanostructures/chemistry , Hydrophobic and Hydrophilic Interactions , Particle Size
9.
Bioorg Chem ; 147: 107377, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38653150

ABSTRACT

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.


Subject(s)
Acetylcholinesterase , Alzheimer Disease , Cholinesterase Inhibitors , Diterpenes , Euphorbia , Neuroprotective Agents , Diterpenes/pharmacology , Diterpenes/chemistry , Diterpenes/chemical synthesis , Alzheimer Disease/drug therapy , Cholinesterase Inhibitors/pharmacology , Cholinesterase Inhibitors/chemical synthesis , Cholinesterase Inhibitors/chemistry , Neuroprotective Agents/pharmacology , Neuroprotective Agents/chemistry , Neuroprotective Agents/chemical synthesis , Euphorbia/chemistry , Humans , Acetylcholinesterase/metabolism , Structure-Activity Relationship , Molecular Structure , Molecular Docking Simulation , Dose-Response Relationship, Drug , Cell Survival/drug effects
10.
Fitoterapia ; 175: 105965, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38631599

ABSTRACT

Four new diterpenoids, including three secolathyrane diterpenoids (1-3) and one lathyrane diterpenoid (4), together with seven known diterpenoids, were obtained in the shelled seeds of Euphorbia lathyris. In particular, 1-3 possess a rare split ring structure, and currently only one compound with the same skeleton has been identified in E. lathyris. Compound 4 furnishes an unprecedented oxygen bridge structure. The structures were identified using various spectral techniques, including NMR, HR-ESI-MS, single-crystal X-ray diffraction and calculated electronic circular dichroism (ECD). The biosynthetic pathway of 1-4 was inferred. Furthermore, the cytotoxic activities of all compounds (1-11) were measured on three human tumor cells. New compounds 2 and 3 showed moderate cytotoxic activities against U937 cells with IC50 values of 22.18 and 25.41 µM, respectively.


Subject(s)
Antineoplastic Agents, Phytogenic , Diterpenes , Euphorbia , Phytochemicals , Seeds , Euphorbia/chemistry , Diterpenes/isolation & purification , Diterpenes/pharmacology , Diterpenes/chemistry , Humans , Molecular Structure , Seeds/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Cell Line, Tumor , China , U937 Cells
11.
Phytomedicine ; 129: 155666, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38678953

ABSTRACT

BACKGROUND: Euphorbia helioscopia L (EHL), a widely used medicinal plant in traditional Chinese medicine, has shown promising effects on certain cancers. However, previous studies on EHL did not elucidate the underlying molecular mechanisms. Herein, for the first time, we present the strong therapeutic potential of EHL extracts on malignant hemangioendothelioma, a rare type of vascular tumor. PURPOSE: To investigate the potential anti-tumor mechanism of extracts of EHL on hemangioendothelioma and melanoma. METHODS: The dried stems and leaves of EHL were extracted with Ethyl Acetate and n-Butyl alcohol, yielding two crude extracts Ethyl Acetate fraction (EA) and n-Butyl alcohol fraction (Bu). EA and Bu were prepared to assess the potential mechanism by assays for cell proliferation, cell cycle, apoptosis, colony formation, tube formation, cellular metabolic activity, reactive oxygen species (ROS), N-Acetylcysteine (NAC) antagonism, RNA expression and western blot. To further confirm the anti-tumor effect of EHL in vivo, we established hemangioendothelioma and melanoma tumor-bearing mouse model using node mice and administered with EA and Bu, tracked alterations in tumor volume and survival rate. Furthermore, tissue samples were obtained for histological, protein, and genetic investigations. RESULTS: We demonstrate that the injection of EA and Bu, significantly inhibits tumor growth and prolongs the lifespan of tumor-bearing mice. Bu treatment exhibited a remarkable 33 % healing effect on the primary hemangioendothelioma tumor, bringing the survival rate to a level comparable to that of healthy mice. Mechanically, both EA and Bu impair respiratory chain complexes, leading to mitochondrial dysfunction and accumulation of reactive oxygen species (ROS), resulting in DNA damage, cell apoptosis, and finally blocked angiogenesis. While EA demonstrates robust inhibitory effects on cancer cell growth and a broader impact on metabolism in vitro, the in vivo effect of Bu surpasses that of EA in terms of strength. EA and Bu also exhibit potent anti-tumor effects on a primary melanoma model by inhibiting angiogenesis. Importantly, when compared to other compounds used in the treatment of hemangioendothelioma, EA and Bu demonstrate more profound anti-tumor effects. CONCLUSION: For the first time, our findings reveal that EHL extracts, especially the high polarity compounds, exhibit potent anti-tumor effects by targeting cellular metabolism, specifically through the inhibition of mitochondria-related metabolic activities. This leads to the accumulation of ROS and effectively suppresses abnormal angiogenesis.


Subject(s)
Angiogenesis Inhibitors , Antineoplastic Agents, Phytogenic , Apoptosis , Cell Proliferation , Euphorbia , Hemangioendothelioma , Plant Extracts , Reactive Oxygen Species , Animals , Euphorbia/chemistry , Hemangioendothelioma/drug therapy , Reactive Oxygen Species/metabolism , Angiogenesis Inhibitors/pharmacology , Humans , Apoptosis/drug effects , Cell Proliferation/drug effects , Mice , Plant Extracts/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Melanoma/drug therapy , Plant Leaves/chemistry , Melanoma, Experimental/drug therapy , Neovascularization, Pathologic/drug therapy , Mice, Inbred C57BL , Male , Angiogenesis
12.
J Agric Food Chem ; 72(17): 9746-9754, 2024 May 01.
Article in English | MEDLINE | ID: mdl-38602331

ABSTRACT

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.


Subject(s)
Antinematodal Agents , Caenorhabditis elegans , Euphorbia , Latex , Protein Kinase C , Animals , Caenorhabditis elegans/drug effects , Caenorhabditis elegans/genetics , Caenorhabditis elegans/enzymology , Caenorhabditis elegans/metabolism , Caenorhabditis elegans/growth & development , Latex/chemistry , Latex/metabolism , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Antinematodal Agents/metabolism , Euphorbia/chemistry , Protein Kinase C/metabolism , Protein Kinase C/genetics , Plant Extracts/pharmacology , Plant Extracts/chemistry
13.
Sci Rep ; 14(1): 5627, 2024 03 07.
Article in English | MEDLINE | ID: mdl-38454096

ABSTRACT

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.


Subject(s)
Acetates , Anti-Infective Agents , Communicable Diseases , Euphorbia , Euphorbiaceae , Antioxidants/pharmacology , Antioxidants/chemistry , Methanol/chemistry , Chloroform , Chromatography, High Pressure Liquid , Anti-Infective Agents/pharmacology , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Phytochemicals/pharmacology , Phytochemicals/chemistry , Flavonoids/analysis , Phenols/analysis , Microbial Sensitivity Tests
14.
Bioorg Chem ; 145: 107253, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38452588

ABSTRACT

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.


Subject(s)
Diterpenes , Euphorbia , Osteogenesis , Euphorbia/chemistry , Plant Extracts/chemistry , Osteoclasts , Diterpenes/pharmacology , Diterpenes/chemistry , Molecular Structure
15.
Molecules ; 29(5)2024 Feb 29.
Article in English | MEDLINE | ID: mdl-38474596

ABSTRACT

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%).


Subject(s)
Antineoplastic Agents , Diterpenes , Euphorbia , Triterpenes , Euphorbia/chemistry , Abietanes , Molecular Structure , Diterpenes/chemistry , Triterpenes/chemistry , Anti-Inflammatory Agents
16.
Comput Biol Chem ; 110: 108037, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38460436

ABSTRACT

Cancer is the most prevalent disease globally, which presents a significant challenge to the healthcare industry, with breast and lung cancer being predominant malignancies. This study used RNA-seq data from the TCGA database to identify potential biomarkers for lung and breast cancer. Tumor Necrosis Factor (TNFAIP8) and Sulfite Oxidase (SUOX) showed significant expression variation and were selected for further study using structure-based drug discovery (SBDD). Compounds derived from the Euphorbia ammak plant were selected for in-silico study with both TNFAIP8 and SUOX. Stigmasterol had the greatest binding scores (normalized scores of -8.53 kcal/mol and -9.69 kcal/mol) with both proteins, indicating strong stability in their binding pockets throughout the molecular dynamics' simulation. Although Stigmasterol first changed its initial conformation (RMSD = 0.5 nm with the starting conformation) in SUOX, it eventually reached a stable conformation (RMSD of 1.5 nm). The compound on TNFAIP8 showed a persistent shape (RMSD of 0.35 nm), indicating strong protein stability. The binding free energy of the complex was calculated using the MM/GBSA technique; TNFAIP8 had a ΔGTOTAL of -24.98 kcal/mol, with TYR160 being the most significant residue, contributing -2.52 kcal/mol. On the other hand, the SUOX complex had a binding free energy of -16.87 kcal/mol, with LEU151 being the primary contributor (-1.17 kcal/mol). Analysis of the complexes' free energy landscape unveiled several states with minimum free energy, indicating robust interactions between the protein and ligand. In its conclusion, this work emphasises the favourable ability of Stigmasterol to bind with prospective targets for lung and breast cancer, indicating the need for more experimental study.


Subject(s)
Breast Neoplasms , Euphorbia , Lung Neoplasms , Stigmasterol , Euphorbia/chemistry , Breast Neoplasms/drug therapy , Breast Neoplasms/metabolism , Humans , Lung Neoplasms/drug therapy , Lung Neoplasms/metabolism , Stigmasterol/chemistry , Stigmasterol/pharmacology , Stigmasterol/analogs & derivatives , Stigmasterol/isolation & purification , Female , Molecular Dynamics Simulation , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Molecular Structure , Thermodynamics , Molecular Docking Simulation
17.
Plant Biol (Stuttg) ; 26(3): 398-414, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38444147

ABSTRACT

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.


Subject(s)
Euphorbia , Biological Evolution , Euphorbia/genetics , Phylogeny , Phylogeography , Spain
18.
Bol. latinoam. Caribe plantas med. aromát ; 23(2): 160-179, mar. 2024. ilus, tab, graf
Article in English | LILACS | ID: biblio-1538275

ABSTRACT

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.


Subject(s)
Plants, Medicinal , Euphorbia , Zimbabwe , Ethnobotany
19.
Fitoterapia ; 174: 105854, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38331050

ABSTRACT

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.


Subject(s)
Diterpenes , Euphorbia , Phenylpropionates , Molecular Structure , Euphorbia/chemistry , Drug Resistance, Multiple , Diterpenes/pharmacology , Diterpenes/chemistry , ATP Binding Cassette Transporter, Subfamily B, Member 1/metabolism , ATP Binding Cassette Transporter, Subfamily B, Member 1/pharmacology , ATP Binding Cassette Transporter, Subfamily B
20.
Phytochemistry ; 221: 114043, 2024 May.
Article in English | MEDLINE | ID: mdl-38417720

ABSTRACT

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.


Subject(s)
Diterpenes , Euphorbia , Phorbols , Euphorbia/chemistry , Antioxidants/pharmacology , Hydrogen Peroxide/pharmacology , Molecular Structure , Diterpenes/pharmacology , Diterpenes/chemistry
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