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1.
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
2.
Int J Health Sci (Qassim) ; 18(2): 25-32, 2024.
Article in English | MEDLINE | ID: mdl-38455597

ABSTRACT

Objectives: Silver nanoparticles (AgNPs) are gaining increasing attention in biomedical applications due to their unique properties. Green synthesis methods are environmentally friendly and have demonstrated potential for AgNP production. This study explores the green synthesis of AgNPs using the methanolic extract of Euphorbia milii, a plant known for its medicinal properties. The primary objectives of this research were to synthesize AgNPs using E. milii extract, characterize the nanoparticles (NPs) using various techniques, and evaluate their antibacterial and enzyme inhibitory activities. Methods: E. milii plant extract was utilized for the green synthesis of AgNPs. The characterization of the NPs was performed through ultraviolet-visible spectroscopy (UV-Vis), Fourier-transform infrared spectroscopy, scanning electron microscopy, and energy-dispersive X-ray spectroscopy (EDX). Antibacterial activity was assessed against Staphylococcus aureus, while enzyme inhibitory assays were conducted against urease, α-glucosidase, carbonic anhydrase II, and xanthine oxidase. Results: The synthesized AgNPs exhibited significant antibacterial effects, with a remarkable 20-mm zone of inhibition against S. aureus, surpassing the efficacy of the plant extract alone. Furthermore, the AgNPs demonstrated remarkable enzyme inhibition, achieving impressive percentages of 77.98% against α-glucosidase and 88.54% against carbonic anhydrase II. Half-maximal inhibitory concentration values for enzyme inhibition were highly promising, including 78.09 ± 1.98 µM for α-glucosidase, 0.22 ± 0.10 µM for carbonic anhydrase II, and 7.11 ± 0.55 µM for xanthine oxidase. Conclusion: In this study, AgNPs were successfully synthesized using E. milii extract and characterized using various techniques. The AgNPs exhibited significant antibacterial and enzyme-inhibitory activities, showcasing their potential for biomedical applications.

3.
Artif Cells Nanomed Biotechnol ; 51(1): 255-267, 2023 Dec.
Article in English | MEDLINE | ID: mdl-37154794

ABSTRACT

Respiratory tract infections are a common cause of morbidity and mortality globally. The current paper aims to treat this respiratory disorder. Therefore, we elucidated the phytochemical profile of Euphorbia milii flowers and isolated chlorogenic acid (CGA) for the first time. The electrospraying technique was utilized to prepare CGA nanoparticles in polyvinyl alcohol (PVA)/PLGA polymeric matrix. Complete in vitro characterizations were performed to determine particle size, polydispersity index (PDI), zeta potential, loading efficiency (LE), scanning electron microscopy and in vitro release study. The optimum formula (F2) with a particle size (454.36 ± 36.74 nm), a surface charge (-4.56 ± 0.84 mV), % of LE (80.23 ± 5.74), an initial burst (29.46 ± 4.79) and % cumulative release (97.42 ± 4.72) were chosen for further activities. In the murine lung infection model, PVA/PLGA NPs loaded with CGA (F2) demonstrated in vivo antibacterial activity against Pseudomonas aeruginosa. Using a plaque assay, the in vitro antiviral activity was investigated. The F2 exhibited antiviral activity against coronavirus (HCoV-229E) and (Middle East respiratory syndrome coronavirus (MERS-CoV), NRCEHKU270). The IC50 of F2 against HCoV-229E and MERS-CoV was 170 ± 1.1 and 223 ± 0.88 µg/mL, respectively. The values of IC50 of F2 were significantly lower (p < .05) than that of free CGA. Therefore, the encapsulation of CGA into electrospray PVA/PLGA NPs would be a promising tool as an antimicrobial agent.


Subject(s)
Middle East Respiratory Syndrome Coronavirus , Nanoparticles , Mice , Animals , Polyvinyl Alcohol/chemistry , Antiviral Agents , Polylactic Acid-Polyglycolic Acid Copolymer/chemistry , Chlorogenic Acid/pharmacology , Pseudomonas aeruginosa , Anti-Bacterial Agents/pharmacology , Lung , Nanoparticles/chemistry
4.
Arch Microbiol ; 204(11): 661, 2022 Oct 04.
Article in English | MEDLINE | ID: mdl-36192448

ABSTRACT

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.


Subject(s)
Anti-Infective Agents , Chaetomium , Euphorbia , Acetates , Anti-Infective Agents/metabolism , Anti-Infective Agents/pharmacology , Apigenin/metabolism , Apigenin/pharmacology , Bacillus subtilis , Chromatography, Liquid , Endophytes , Escherichia coli , Esters/metabolism , Gas Chromatography-Mass Spectrometry , Gram-Negative Bacteria , Hexanes , Linoleic Acid/metabolism , Linoleic Acid/pharmacology , Microbial Sensitivity Tests , Phytochemicals/pharmacology , Tandem Mass Spectrometry
5.
Phytochemistry ; 196: 113106, 2022 Apr.
Article in English | MEDLINE | ID: mdl-35078105

ABSTRACT

Four undescribed regular rosane-type diterpenoids euphominoids M-P and three undescribed rearranged rosane-type diterpenoids euphomilones C-E were isolated from the whole plants of Euphorbia milii Des Moul., along with nine known compounds. Their structures were elucidated by detailed interpretation of the NMR and mass spectroscopy. The absolute configurations were established by single-crystal X-ray diffraction experiments, as well as comparative analyses of calculated and experimental ECD spectra. Euphominoid M featured a highly oxygenated ring A and a rare four-membered oxygen ring while euphomilones C-E possessed 7/5/6 or 5/7/6 fused ring systems, which were rarely occurring in rosane-type diterpenoids. In the in-vitro bioassays, 19-norrosa-1,3,5(10),15-tetraene-2,3-diol and antiquorin showed more potent α-glucosidase inhibitory activity than the positive control acarbose while euphominoid C exhibited significant inhibitory activity against both α-glucosidase and ß-glucuronidase. To the best of our knowledge, it was the first time that rosane-type diterpenoids were reported as ß-glucuronidase inhibitors.


Subject(s)
Diterpenes , Euphorbia , Diterpenes/chemistry , Diterpenes/pharmacology , Enzyme Inhibitors , Euphorbia/chemistry , Glucuronidase , Molecular Structure , alpha-Glucosidases
6.
Mitochondrial DNA B Resour ; 5(1): 426-427, 2020 Jan 08.
Article in English | MEDLINE | ID: mdl-33366586

ABSTRACT

Euphorbia milii (Euphorbiaceae) grows as a scrambling shrub with many branches. Here, we report and characterize the complete plastome of E. milii in an effort to provide genomic resources useful for promoting its systematic research. The plastome of E. milii is found to possess a total length of 160,806 bp with the typical quadripartite structure of angiosperms, contains two Inverted Repeats (IRs) of 26,695 bp, a Large Single-Copy (LSC) region of 90,211 bp and a Small Single-Copy (SSC) region of 17,205 bp. The plastome contains 114 genes, consisting of 80 unique protein-coding genes, 30 unique tRNA genes and four unique rRNA genes. The overall A/T content in the plastome of E. milii is of 64.10%. The phylogenetic analysis indicated that E. milii is close to E. tirucalli within Euphorbiaceae in this study. The complete plastome sequence of E. milii will provide a useful resource for the conservation genetics of this species as well as for the phylogenetic studies of Euphorbiaceae.

7.
J Photochem Photobiol B ; 191: 13-17, 2019 Feb.
Article in English | MEDLINE | ID: mdl-30557788

ABSTRACT

Multifunctional nanocarriers are in immediate need to develop anticancer activity for the treatment of cancers. In the present research, the graphene oxide was reduced via an efficient method which reduced to RGO by using Euphorbia milii leaves extract. Thus obtained RGO nanocomposites were subsequently characterized by means UV-Vis absorption technique. AFM imaging was further performed in order to analyze the surface morphology of GO nanosheet as well as to estimate the average thickness of the GO nanosheets before and after the addition of Euphorbia milii leaves extract. Furthermore, the anticancer effect of RGO-loaded PTX (RGO/PTX) on A549 (Human lung cancer cell lines) was evaluated by MTT assay. The results displayed that with the increase in the concentration of RGO/PTX to200 ??g/mL, the cell viability reduced to 29%. Even more increase in the concentration to 500 ??g/mL of RGO/PTX, the cell viability also showed rapid reduction to 10%. Based on this, we can conclude that the increased concentration of RGO/PTX decreased the cell viability of A549 cell lines tremendously and has the potential to serve in the lung carcinoma targeted chemotherapy.


Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Drug Carriers/chemical synthesis , Euphorbia/chemistry , Graphite/chemistry , Lung Neoplasms/drug therapy , Paclitaxel/pharmacology , A549 Cells , Cell Survival/drug effects , Humans , Lung Neoplasms/pathology , Nanocomposites/chemistry , Oxidation-Reduction , Paclitaxel/therapeutic use , Plant Extracts/chemistry , Plant Extracts/therapeutic use
8.
Rev. Soc. Bras. Med. Trop ; 52: e20190252, 2019. graf
Article in English | LILACS | ID: biblio-1041533

ABSTRACT

Abstract INTRODUCTION In Brazil, Biomphalaria glabrata, B. tenagophila, and B. straminea are intermediate hosts of Schistosoma mansoni, the etiological agent of schistosomiasis mansoni. Molluscicide use is recommended by the WHO for controlling the transmission of this parasite. Euphorbia milii latex has shown promising results as an alternative molluscicide. Thus, a natural molluscicide prototype kit based on freeze-dried E. milii latex was developed and evaluated against Biomphalaria spp. METHODS E. milii latex was collected, processed, and lyophilized. Two diluents were defined for freeze-dried latex rehydration, and a prototype kit, called MoluSchall, was produced. A stability test was conducted using prototype kits stored at different temperatures, and a toxicity assay was performed using Danio rerio. Additionally, MoluSchall was tested against B. glabrata under semi-natural conditions according to defined conditions in the laboratory. RESULTS MoluSchall was lethal to three Brazilian snail species while exhibiting low toxicity to D. rerio. Regardless of storage temperature, MoluSchall was stable for 24 months and was effective against B. glabrata under semi-natural conditions, with the same LD100 as observed under laboratory conditions. CONCLUSIONS MoluSchall is a natural, effective, and inexpensive molluscicide with lower environmental toxicity than existing molluscicides. Its production offers a possible alternative strategy for controlling S. mansoni transmission.


Subject(s)
Animals , Schistosoma mansoni/drug effects , Biomphalaria/parasitology , Schistosomiasis mansoni/prevention & control , Euphorbia/chemistry , Latex/pharmacology , Molluscacides/pharmacology , Biomphalaria/drug effects , Latex/isolation & purification , Molluscacides/isolation & purification
9.
J Photochem Photobiol B ; 183: 137-141, 2018 Jun.
Article in English | MEDLINE | ID: mdl-29705505

ABSTRACT

Silver nanoparticles (AgNPs) have been emerged as significant wound healing agents because of their improved mechanical properties. However, the green synthesized silver nanoparticleshave reported significant wound healing action in Albino rats which was validated by the measurement of wound closure rate. Silver nanoparticles were efficiently synthesized using Euphorbia milii leaf extract. The UV-visible spectra recorded the effect of the reaction time on AgNPs synthesis and was indentified that the peak became shaper with an increase in time, which corresponds to increase in the number of nanoparticles formed from the reduction of silver ions present in the aqueous solution. X-ray diffraction technique and corresponding XRD patterns confirmed the biphasic nature of the biosynthesized silver nanoparticles. However, low magnification TEM images presented monodispersed AgNPs with their size ranging from 20 to 30 nm while SAED diffraction pattern disclosed their crystalline nature. Furthermore, the wound healing activity of AgNPs was examined through the excision wound model by measuring the rate of wound closure and Group II (treated with 10% Ointment base with biosynthesized AgNPs) revealed significant wound healing activity over Control group and Group I (treated with Standard Nitrofurazone ointment) in Albino rats.


Subject(s)
Metal Nanoparticles/chemistry , Ointments/pharmacology , Silver/chemistry , Wound Healing/drug effects , Animals , Drug Compounding , Euphorbia/chemistry , Euphorbia/metabolism , Green Chemistry Technology , Hospitals , Male , Microscopy, Electron, Transmission , Nursing Care , Ointments/chemistry , Plant Extracts/chemistry , Plant Leaves/chemistry , Plant Leaves/metabolism , Rats , Spectrophotometry, Ultraviolet , Spectroscopy, Fourier Transform Infrared , X-Ray Diffraction
10.
Plant Physiol Biochem ; 111: 284-294, 2017 Feb.
Article in English | MEDLINE | ID: mdl-27987473

ABSTRACT

Better understanding of plant-bacteria interactions under stress is of the prime importance for enhancing airborne pollutant phytoremediation. No studies have investigated plant-epiphyte interactions compared to plant-endophyte interactions under airborne formaldehyde stress in terms of plant Indole-3-acetic acid (IAA), ethylene, reactive oxygen species (ROS) levels and pollutant removal efficiency. Euphorbia milii was inoculated with native plant growth-promoting (PGP) endophytic and epiphytic isolates individually to investigate plant-endophyte compared to plant-epiphyte interactions under continuous formaldehyde fumigation. Under airborne formaldehyde stress, endophyte interacts with its host plant closely and provides higher levels of IAA which protected the plant against formaldehyde phytotoxicity by lowering intracellular ROS, ethylene levels and maintaining shoot epiphytic community; hence, higher pollutant removal. However, plant-epiphyte interactions could not provide enough IAA to confer protection against formaldehyde stress; thus, increased ROS and ethylene levels, large decrease in shoot epiphytic population and lower pollutant removal although epiphyte contacts with airborne pollutant directly (has greater access to gaseous formaldehyde). Endophyte-inoculated plant synthesized more tryptophan as a signaling molecule for its associated bacteria to produce IAA compared to the epiphyte-inoculated one. Under stress, PGP endophyte interacts with its host closely; thus, better protection against stress and higher pollutant removal compared to epiphyte which has limited interactions with the host plant; hence, lower pollutant removal.


Subject(s)
Air Pollutants/toxicity , Bacteria/metabolism , Ethylenes/metabolism , Euphorbia/microbiology , Formaldehyde/toxicity , Indoleacetic Acids/metabolism , Reactive Oxygen Species/metabolism , Stress, Physiological/drug effects , Bacteria/drug effects , Bacteria/growth & development , Bacteria/isolation & purification , Chlorophyll/metabolism , Colony Count, Microbial , Endophytes/drug effects , Endophytes/physiology , Plant Shoots/drug effects , Plant Shoots/microbiology , Plant Stomata/drug effects , Plant Stomata/physiology , Signal Transduction/drug effects , Tryptophan/metabolism
11.
Plant Physiol Biochem ; 107: 326-336, 2016 Oct.
Article in English | MEDLINE | ID: mdl-27362296

ABSTRACT

Phytoremediation could be a cost-effective, environmentally friendly approach for the treatment of indoor air. However, some drawbacks still dispute the expediency of phytotechnology. Our objectives were to investigate the competency of plant growth-promoting (PGP) endophytic Bacillus cereus ERBP (endophyte root blue pea), isolated from the root of Clitoria ternatea, to colonize and stabilize within Zamioculcas zamiifolia and Euphorbia milii as non-native hosts without causing any disease or stress symptoms. Moreover, the impact of B. cereus ERBP on the natural shoot endophytic community and for the airborne formaldehyde removal capability of non-native hosts was assessed. Non-native Z. zamiifolia was effectively inoculated with B. cereus ERBP through soil as the most efficient method of endophyte inoculation. Denaturing gradient gel electrophoresis profiling of the shoot endophytic community verified the colonization and stability of B. cereus ERBP within its non-native host during a 20-d fumigation period without interfering with the natural shoot endophytic diversity of Z. zamiifolia. B. cereus ERBP conferred full protection to its non-native host against formaldehyde phytotoxicity and enhanced airborne formaldehyde removal of Z. zamiifolia whereas non-inoculated plants suffered from formaldehyde phytotoxicity because their natural shoot endophytic community was detrimentally affected by formaldehyde. In contrast, B. cereus ERBP inoculation into non-native E. milii deteriorated airborne formaldehyde removal of the non-native host (compared to a non-inoculated one) as B. cereus ERBP interfered with natural shoot endophytic community of E. milii, which caused stress symptoms and stimulated ethylene biosynthesis. Non-native host inoculation with PGP B. cereus ERBP could bear potentials and challenges for airborne formaldehyde removal.


Subject(s)
Air Pollutants/isolation & purification , Araceae/microbiology , Bacillus cereus/physiology , Endophytes/physiology , Euphorbia/microbiology , Formaldehyde/isolation & purification , Araceae/drug effects , Araceae/genetics , Bacillus cereus/drug effects , Biodegradation, Environmental/drug effects , Denaturing Gradient Gel Electrophoresis , Endophytes/drug effects , Euphorbia/drug effects , Euphorbia/genetics , Formaldehyde/toxicity , Genes, Plant , Indoleacetic Acids/metabolism , Plant Shoots/drug effects , Plant Shoots/genetics , Plant Stomata/drug effects , Plant Stomata/physiology , RNA, Ribosomal, 16S/genetics , Stress, Physiological/drug effects , Stress, Physiological/genetics
12.
Environ Sci Pollut Res Int ; 23(17): 17067-76, 2016 Sep.
Article in English | MEDLINE | ID: mdl-27209635

ABSTRACT

Trimethylamine (TMA) is a volatile organic compound which causes not only unpleasant odor but also health concerns to humans. The average emission of TMA from food and fishery industries is 20.60 parts per billion (ppb) and emission from the gas exhausters is even higher which reaches 370 parts per million (ppm). In order to select the best plant TMA removal agent, in this study, 13 plants were exposed to 100 ppm of TMA and the remaining TMA concentration in their system was analyzed by gas chromatography (GC). Furthermore, plant metabolites from the selected plant were identified by gas chromatography-mass spectrometry (GC-MS). The result showed that Euphorbia milii was the most superior plant for TMA removal and could absorb up to 90 % of TMA within 12 h. E. milii absorbed TMA via leaf and stem with 55 and 45 % uptake efficiency, respectively. Based on its stomatal movement during the exposure to TMA, it was implied that the plant switched the photosynthetic mode from crassulacean acid metabolism (CAM)-cycling to CAM and CAM-idling. The switching of photosynthetic mode might reduce the stomata role in TMA absorption. Fatty acids, alkanes, and fatty alcohols in the plant leaf wax were also found to contribute to TMA adsorption. Leaf wax, stomata, and other leaf constituents contributed 58, 6, and 36 %, respectively, of the total TMA absorption by the leaf. The analysis and identification of plant metabolites confirmed that TMA was degraded and mineralized by E. milii.


Subject(s)
Air Pollutants , Euphorbia , Methylamines , Air Pollutants/analysis , Air Pollutants/metabolism , Biodegradation, Environmental , Euphorbia/chemistry , Euphorbia/metabolism , Euphorbia/physiology , Gas Chromatography-Mass Spectrometry , Methylamines/analysis , Methylamines/metabolism , Photosynthesis , Plant Leaves/chemistry , Plant Leaves/metabolism , Plant Leaves/physiology
13.
Rev. bras. farmacogn ; 19(2a): 418-422, Apr.-June 2009. ilus, tab
Article in Portuguese | LILACS | ID: lil-524548

ABSTRACT

O objetivo deste trabalho foi avaliar a mutagenicidade e o grau de toxicidade de duas plantas tóxicas, a "mamona" (Ricinus communis) e a "coroa-de-cristo" (Euphorbia milii), utilizando infusões das sementes de mamona e o látex da coroa-de-cristo, em células meristemáticas de Allium cepa. Foram analisados: o índice mitótico (IM), as anomalias do ciclo mitótico (ACM), anomalias interfásicas, (AI) e o total de anomalias (TA). As soluções testes foram preparadas em três concentrações: MT1 - 0,5 g/l, MT2 - 1,0 g/l, MT3 - 2,0 g/l, e MT4 como controle. Da coroa-de-cristo extraiu-se o látex e dissolveu-se em água destilada nas concentrações CT1 -0,5 ml/l, CT2 - 1,0 ml/l, CT3 - 2,0 ml/l, e CT4 controle. Os resultados constataram que somente a mamona aumentou a freqüência de anomalias do ciclo mitótico, assim como, as anomalias interfásicas, demonstrando, dessa forma, uma ação tóxica para o material genético, através do teste de Allium cepa.


The aim of this work was to evaluate the mutagenicity and the degree of toxicity of two toxic plants, "castor bean" (Ricinus communis) and the "crown-of-thorns" (Euphorbia milii), using infusions of the seeds of Ricinus communis and the latex of the Euphorbia milii, in meristematic cells of Allium cepa, which were analyzed: the mitotic index (IM), the interphasics anomalies (AI), the mitotic cycle anomalies (ACM), and the total of anomalies (TA). The solutions tests were prepared in three concentrations: MT1 - 0.5 g/l, MT2 - 1.0 g/l, MT3 -2.0 g/l, and MT4 as control. From the Euphorbia milii the latex was extracted and was diluted in distilled water in concentrations: CT1 - 0.5 ml/l, CT2 - 1.0 ml/l, CT3 - 2.0 ml/l, and CT4 as control. The results evidenced that Ricinus communis increased the frequency of mitotic cycle anomalies, as well, the interphasics anomalies, demonstrating, a toxic action for the genetic material, through the test of Allium cepa.

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