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1.
Phytochemistry ; 222: 114100, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38636688

RESUMO

Artemyriantholides A-K (1-11) as well as 14 known compounds (12-25) were isolated from Artemisia myriantha var. pleiocephala (Asteraceae). The structures and absolute configuration of compounds 2 and 8-9 were confirmed by the single crystal X-ray diffraction analyses, and the others were elucidated by MS, NMR spectral data and electronic circular dichroism calculations. All compounds were chemically characterized as guaiane-type sesquiterpenoid dimers (GSDs). Compound 1 was the first example of the GSD fused via C-3/C-11' and C-5/C-13' linkages, and compounds 2 and 5 were rare GSDs containing chlorine atoms. Eleven compounds showed obvious inhibitory activity in HepG2, Huh7 and SK-Hep-1 cell lines by antihepatoma assay to provide the IC50 values ranging from 7.9 to 67.1 µM. Importantly, compounds 5 and 8 exhibited the best inhibitory activity with IC50 values of 14.2 and 18.8 (HepG2), 9.0 and 11.5 (Huh7), and 8.8 and 11.3 µM (SK-Hep-1), respectively. The target of compound 5 was predicted to be MAP2K2 by a computational prediction model. The interaction between compound 5 and MAP2K2 was conducted to give docking score of -9.0 kcal/mol by molecular docking and provide KD value of 43.7 µM by Surface Plasmon Resonance assay.


Assuntos
Artemisia , Artemisia/química , Humanos , Estrutura Molecular , Relação Estrutura-Atividade , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/farmacologia , Sesquiterpenos de Guaiano/isolamento & purificação , Animais , Dimerização , Simulação de Acoplamento Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral
2.
Molecules ; 29(6)2024 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-38543021

RESUMO

As part of our interest in the volatile phytoconstituents of aromatic plants of the Great Basin, we have obtained essential oils of Ambrosia acanthicarpa (three samples), Artemisia ludoviciana (12 samples), and Gutierrezia sarothrae (six samples) from the Owyhee Mountains of southwestern Idaho. Gas chromatographic analyses (GC-MS, GC-FID, and chiral GC-MS) were carried out on each essential oil sample. The essential oils of A. acanthicarpa were dominated by monoterpene hydrocarbons, including α-pinene (36.7-45.1%), myrcene (21.6-25.5%), and ß-phellandrene (4.9-7.0%). Monoterpene hydrocarbons also dominated the essential oils of G. sarothrae, with ß-pinene (0.5-18.4%), α-phellandrene (2.2-11.8%), limonene (1.4-25.4%), and (Z)-ß-ocimene (18.8-39.4%) as major components. The essential oils of A. ludoviciana showed wide variation in composition, but the relatively abundant compounds were camphor (0.1-61.9%, average 14.1%), 1,8-cineole (0.1-50.8%, average 11.1%), (E)-nerolidol (0.0-41.0%, average 6.8%), and artemisia ketone (0.0-46.1%, average 5.1%). This is the first report on the essential oil composition of A. acanthicarpa and the first report on the enantiomeric distribution in an Ambrosia species. The essential oil compositions of A. ludoviciana and G. sarothrae showed wide variation in composition in this study and compared with previous studies, likely due to subspecies variation.


Assuntos
Artemisia , Óleos Voláteis , Óleos Voláteis/química , Artemisia/química , Ambrosia , Idaho , Monoterpenos/análise
3.
Phytochemistry ; 220: 114019, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38346546

RESUMO

Seven undescribed sesquiterpenes, including three dimeric guaianolide sesquiterpenes artemongolides G-I (1-3) and four sesquiterpene lactones artemanomalide D-G (16-19), along with seventeen known compounds isoabsinthin (4), absinthin (5), 11-eptabsinthin (6), 11, 11'-bis-epiabsinthin (7), 10', 11'- epiabsinthin (8), anabsinthin (9), isoanabsinthin (10), absinthin D (11), anabsin (12), caruifolin D (13), gnapholide (14), caruifolin C (15), 1ß(R),10ß(S)-dihydroxy-3-oxo-11ß (S)H-4,11(13)-guaien-6α(S),12-olide (20), 1α,6α,8α-trihydroxy-5α,7ßH-guaia-3,10(14),11(13)-trien-12-oic acid (21), 1α,6α,8α-trihydroxy-5α,7ßH-guaia-3,9,11(13)-trien-12-oic acid (22), argyinolide J (23), artabsinolide A (24) were isolated from the plant Artemisia mongolica. The structures were determined by interpreting NMR, HRESIMS and ECD data. The X-ray crystal structure of 4, 7 and 8 were reported for the first time. In the anti-vitiligo activity test, compounds 2, 7, 12, 23 and 24 demonstrated activity in promoting melanogenesis at a concentration of 50 µM in B16 cells, with 8-methoxypsoralan (8-MOP) as a positive control. Further research on the mechanism revealed that artemongolides H (2) enhance the expression of MITF and TRPs by upregulating p-Akt and p-GSK-3ß, leading to an increase in ß-catenin content in the cell cytoplasm. Subsequently, ß-catenin translocates into the nucleus, resulting in melanogenesis. The results supported the regulation of melanogenesis by artemongolide H (2) through the Akt/GSK3ß/ß-catenin signaling pathway. The anti-inflammatory results demonstrated that compounds 4, 5, 6, 9 and 14 can inhibit the upregulation of IL-6 mRNA and CCL2 mRNA expression. Compound 12 specifically inhibited the upregulation of IL-6 mRNA expression. These compounds exhibited significant anti-inflammatory activities. The activity results revealed that these sesquiterpene compounds have the potential to become lead compounds for the treatment of vitiligo and inflammatory diseases.


Assuntos
Artemisia , Asteraceae , Sesquiterpenos , Artemisia/química , beta Catenina , Glicogênio Sintase Quinase 3 beta , Interleucina-6 , Proteínas Proto-Oncogênicas c-akt , Trientina , Sesquiterpenos/farmacologia , Sesquiterpenos/química , Sesquiterpenos de Guaiano/farmacologia , Sesquiterpenos de Guaiano/química , Anti-Inflamatórios , RNA Mensageiro , Lactonas/farmacologia , Lactonas/química , Asteraceae/química , Estrutura Molecular
4.
J Ethnopharmacol ; 319(Pt 3): 117364, 2024 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-38380576

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: As a traditional Chinese medicine, Artemisia argyi has been used medicinally and eaten for more than 2000 years in China. It is widely reported in treating inflammatory diseases such as eczema, dermatitis, arthritis, allergic asthma and colitis. Although several studies claim that its volatile oil and organic reagent extracts have certain anti-inflammatory effects, the water-soluble fractions and molecular mechanisms have not been studied. AIM OF THE STUDY: To evaluate the therapeutic effect of A. argyi water extract (AAWE) on lipopolysaccharide (LPS)-induced inflammatory responses and to identify the most effective water-soluble subfractions. Moreover, the relevant pharmacological and molecular mechanisms by which the active subfraction mitigates inflammation were further investigated. MATERIALS AND METHODS: Firstly, RAW 264.7 cells stimulated with LPS were treated with AAWE (50, 100, and 200 µg/mL) or the water-soluble subfractions separated by D101 macroporous resin (AAWE1-AAWE4, 100 µg/mL), and NO production and mRNA levels of inflammatory genes were evaluated to determine the most effective water-soluble subfractions. Secondly, the chemical components of the active subfraction (AAWE4) were analyzed by UPLC-QTOF-MS. Thirdly, transcriptome and network pharmacology analysis, RT-qPCR and Western blotting assays were conducted to explore the underlying anti-inflammatory mechanism and active compounds of AAWE4. Subsequently, the binding ability of the potential active components in AAWE4 to the core targets was further determined by molecular docking. Eventually, the in vivo anti-inflammatory activity of AAWE4 (1.17, 2.34 and 4.68 g/kg, administered per day for 7 d) was evaluated in mice with LPS-induced systemic inflammation. RESULTS: In this study, AAWE showed excellent anti-inflammatory effects, and its water-soluble subfraction AAWE4 exhibited the strongest inhibitory effect on NO concentration and inflammatory gene mRNA expression after LPS stimulation, indicating that it was the most effective subfraction. Thereafter, four main compounds in AAWE4 were confirmed or tentatively identified by UPLC-QTOF-MS, including three flavonoid glycosides and one phenolic acid. Furthermore, the transcriptome and network pharmacology analysis showed that AAWE4 inhibited inflammation via multiple pathways and multiple targets. Based on the RT-qPCR and Western blotting results, AAWE4 downregulated not only the p38, PI3K, CCL5, MMP9, AP-1, and BCL3 mRNA expression levels activated by LPS but also their upstream and downstream protein expression levels and protein phosphorylation (p-AKT/AKT, p-p38/p38, p-ERK/ERK, p-JNK/JNK). Moreover, four identified compounds (isochlorogenic acid A, vicenin-2, schaftoside and isoschaftoside) could significantly inhibit NO content and the overexpression of inflammatory factors TNF-α, IL-1ß, iNOS and COX-2 mRNA induced by LPS, and the molecular docking confirmed the high binding activity of four active compounds with selected core targets (p38, AKT1, MMP9, and CCL5). In addition, the mRNA expression and immunohistochemical analysis showed that AAWE44 could inhibit lung inflammation via multiple pathways and multiple targets in vivo. CONCLUSIONS: The findings of this study suggest that the water-soluble subfraction AAWE4 from A. argyi ameliorated the inflammation caused by LPS through multiple pathways and multiple targets in vitro and in vivo, providing scientific support for the medicinal use of A. argyi. Importantly, it shows that the A. argyi subfraction AAWE4 can be developed as an anti-inflammatory drug.


Assuntos
Artemisia , Lipopolissacarídeos , Animais , Camundongos , Lipopolissacarídeos/toxicidade , Extratos Vegetais/farmacologia , Metaloproteinase 9 da Matriz , NF-kappa B/metabolismo , Água , Artemisia/química , Simulação de Acoplamento Molecular , Proteínas Proto-Oncogênicas c-akt , Inflamação/induzido quimicamente , Inflamação/tratamento farmacológico , Inflamação/metabolismo , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/uso terapêutico , Anti-Inflamatórios/química , RNA Mensageiro
5.
Biomed Chromatogr ; 38(4): e5826, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38205667

RESUMO

Artemisia argyi H.Lév. & Vaniot essential oil (AAEO) has shown pharmacological effects such as anti-inflammation, antioxidant, and anti-tumor properties. However, the protective effect of AAEO on lipopolysaccharide (LPS)-induced liver injury and its potential protective mechanism are still unclear. In this study, we used ultra-performance liquid chromatography tandem mass spectrometry metabolomics techniques to investigate the changes in liver tissue metabolites in mice exposed to LPS with or without AAEO treatment for 14 days. The biochemical results showed that compared with the control group, AAEO significantly reduced the levels of liver functional enzymes, suggesting a significant improvement in liver injury. In addition, the 18 differential metabolites identified by metabolomics were mainly involved in the reprogramming of arachidonic acid metabolism, tryptophan metabolism, and purine metabolism. AAEO could significantly inhibit the expression of COX-2, IDO1, and NF-κB; enhance the body's anti-inflammatory ability; and alleviate liver injury. In summary, our study identified the protective mechanism of AAEO on LPS-induced liver injury at the level of small molecular metabolites, providing a potential liver protective agent for the treatment of LPS-induced liver injury.


Assuntos
Artemisia , Doença Hepática Crônica Induzida por Substâncias e Drogas , Óleos Voláteis , Camundongos , Animais , Artemisia/química , Óleos Voláteis/farmacologia , Lipopolissacarídeos/efeitos adversos , Espectrometria de Massas em Tandem , Espectrometria de Massa com Cromatografia Líquida , Metabolômica
6.
Chem Biodivers ; 21(3): e202301762, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38263615

RESUMO

Artemisia pallens Wall. ex DC (Asteraceae) is cultivated for the production of high-value essential oil from its aerial biomass. In this study, the chemical composition of the root (crop-residue) essential oil was investigated for the first time, using column-chromatography, GC-FID, GC-MS, LC-QTOF, and NMR techniques, which led to the identification of twenty constituents, with isolation of (E)-2-(2',4'-hexadiynylidene)-1,6-dioxaspiro [4.5]dec-3-ene (D6). The D6 was evaluated in vitro for neuroinflammation and acetylcholinesterase inhibitory potential. It showed inhibition of neuroinflammation in a concentration-dependent manner with significant inhibition of pro-inflammatory cytokines (TNF-α and IL-6) in LPS-stimulated BV2 microglial cells. D6 did not have any significant effect on the viability of the cells at the therapeutic concentrations. D6 also has shown acetylcholinesterase inhibitory potential (51.90±1.19 %) at the concentration of log 106  nM. The results showed that D6 has a potential role in the resolution of neuroinflammation, and its acetylcholinesterase inhibitory potential directs further investigation of its role in the management of Alzheimer's disease-related pathogenesis.


Assuntos
Artemisia , Furanos , Óleos Voláteis , Compostos de Espiro , Acetilcolinesterase , Éter , Poli-Inos , Doenças Neuroinflamatórias , Óleos Voláteis/química , Artemisia/química
7.
Braz J Microbiol ; 55(1): 727-735, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-37957442

RESUMO

Artemisia argyi is a traditional Chinese herb with antibacterial, antifungal, and antitumor activities. The essential oil of Artemisia argyi was extracted using the steam distillation method in this study. The chemical composition of the essential oil was analyzed using the gas chromatography-mass spectrometry method. Agar disc diffusion and double-broth dilution assays were used to detect the antimicrobial activity of the essential oil. Subsequently, the antimicrobial mechanisms were explored through cytomembrane permeability assay and electron microscopy. Based on gas chromatography-mass spectrometry analysis, 25 compounds were detected, including 13.76% cineole, 6.77% terpinen-4-ol, 6.68% 3-dione, 1,7,7-trimethyl-, 4.07% 3-cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-acetate, 3.58% 1-isopropyl-2-methylbenzene, and 1.58% g-terpinene. The essential oil was tested for antimicrobial activity, and the IC50 values for Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Listeria monocytogenes, Pseudomonas aeruginosa, Streptococcus pneumoniae, and Candida albicans were determined to be 25.51 ± 2.29, 49.53 ± 0.86, 52.40 ± 1.49, 52.76 ± 1.60, 73.99 ± 1.38, 65.52 ± 0.95, and 214.98 ± 3.27 µg mL-1, respectively. For essential oil interaction with cytoderm, the microorganisms treated by 1 × IC50 and 2 × IC50 concentration of essential oil both represented positive test results. Additionally, the alkaline phosphatase levels showed a direct correlation with concentration and treatment duration (range from 0 to 8 h). The interaction between essential oils and the cytomembrane was investigated by examining samples containing one of three test strains (Staphylococcus aureus, Escherichia coli, and Candida albicans), essential oil, and voltage-sensitive fluorescent dye disc35. The results demonstrated a significant increase in fluorescence levels within the solution upon introduction of the essential oil-treated strains. The findings of our research suggest that the essential oil disrupts the cytoderm and cytomembrane, thereby exhibiting antimicrobial activity.


Assuntos
Anti-Infecciosos , Artemisia , Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Artemisia/química , Testes de Sensibilidade Microbiana , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Bactérias , Antibacterianos/farmacologia , Antibacterianos/química , Fungos , Escherichia coli
8.
Phytochemistry ; 217: 113930, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-37993076

RESUMO

The ethanol and EtOAc extracts of Artemisia sacrorum exhibited inhibitory effect against HepG2, Huh7, and SK-Hep-1 cell lines with inhibitory ratios of 65.5%, 28.1%, 84.6%, and 93.5%, 82.0%, 89.0% at 200 µg/mL. Twenty-three undescribed guaiane-type sesquiterpene lactones, artemisacrolides A‒W, were isolated from A. sacrorum under the guidance of antihepatoma activity. Their structures were elucidated by spectral data (HRESIMS, IR, UV, 1D and 2D NMR), ECD calculations, and a single-crystal X-ray diffraction. Artemisacrolides A‒U were guaiane-type sesquiterpene lactones possessing α-methylene-γ-lactone and containing acetoxyl groups at C-8, and artemisacrolides V and W represented the first report from the genus Artemisia with a 1,10-rearranged guaiane-type sesquiterpene lactone. Antihepatoma assay suggested that artemisacrolides A‒U demonstrated better inhibitory activity in Huh7 and SK-Hep-1 cells than those of HepG2 cells. Among them, nine compounds exhibited significant inhibitory activity against Huh7 cells with IC50 values of 8.2-14.3 µM, superior or equal to that of sorafenib; seven compounds demonstrated obvious activity against SK-Hep-1 cells with IC50 values of 13.5-19.2 µM, which were equivalent to that of sorafenib. Artemisacrolides B and E were the most active ones in three human hepatoma cell lines with IC50 values of 21.9, 8.2, 16.9 and 22.6, 9.0, 17.3 µM.


Assuntos
Artemisia , Sesquiterpenos , Humanos , Artemisia/química , Sorafenibe , Sesquiterpenos de Guaiano/farmacologia , Lactonas/farmacologia , Lactonas/química , Sesquiterpenos/farmacologia , Sesquiterpenos/química , Estrutura Molecular
9.
Sci Rep ; 13(1): 21553, 2023 12 06.
Artigo em Inglês | MEDLINE | ID: mdl-38057542

RESUMO

Liver cancer is the second main reason of death globally. In the current study, Rap2A protein a member of Ras Gtpase was selected as a drug target for liver cancer which has been identified as an oncogene in different types of tumors. The present study aimed to evaluate Artemisia carvifolia Buch extract and its silver nanoparticles against liver cancer targeting the Rap2A gene. The synthesized silver nanoparticles showed an absorbance peak at 450 nm by a UV-Vis spectrophotometer. SEM revealed that polyhedral silver nanoparticles had a size ranging from 80 ± 6 nm. Furthermore, amines, aldehydes, ketones and alcohols of Artemisia carvifolia were found involved in the reduction and stabilization of nanoparticles by FTIR. Moreover, XRD and EDX confirmed the cubic crystalline nature and particle elemental composition, respectively. Furthermore, the cytotoxicity against HePG2 cancer cell lines was also found significant with an IC50 value of 2.57 µM for silver nanoparticles and 11.57 µM for plant extract. The gene expression and protein level of Rap2A were also decreased in plant extract and nanoparticle-treated cells compared to control groups. The apoptotic potential of extract and nanoparticles was also determined by evaluating the apoptotic pathway genes and protein including BAX, caspase 3, 8 and 9. Significantly elevated levels of expression of these genes by real-time qPCR along with increased protein levels by ELISA were found. This is the first-ever report describing the synthesis and efficacy of silver nanoparticles of Artemisia carvifolia Buch against liver cancer.


Assuntos
Artemisia , Neoplasias Hepáticas , Nanopartículas Metálicas , Humanos , Prata/química , Artemisia/química , Nanopartículas Metálicas/química , Extratos Vegetais/química , Neoplasias Hepáticas/tratamento farmacológico , Neoplasias Hepáticas/genética , Antibacterianos/química
10.
Chin J Nat Med ; 21(12): 902-915, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-38143104

RESUMO

In pursuit of effective agents for hepatocellular carcinoma derived from the Artemisia species, this study built upon initial findings that an ethanol (EtOH) extract and ethyl acetate (EtOAc) fraction of the aerial parts of Artemisia dubia Wall. ex Bess. exhibited cytotoxicity against HepG2 cells with inhibitory rates of 57.1% and 84.2% (100 µg·mL-1), respectively. Guided by bioactivity, fourteen previously unidentified sesquiterpenes, artemdubinoids A-N (1-14), were isolated from the EtOAc fraction. Their structural elucidation was achieved through comprehensive spectroscopic analyses and corroborated by the comparison between the experimental and calculated ECD spectra. Single crystal X-ray diffraction provided definitive structure confirmation for artemdubinoids A, D, F, and H. Artemdubinoids A and B (1-2) represented unique sesquiterpenes featuring a 6/5-fused bicyclic carbon scaffold, and their putative biosynthetic pathways were discussed; artemdubinoid C (3) was a novel guaianolide derivative that might be formed by the [4 + 2] Diels-Alder reaction; artemdubinoids D and E (4-5) were rare 1,10-seco-guaianolides; artemdubinoids F-K (6-11) were chlorine-containing guaianolides. Eleven compounds exhibited cytotoxicity against three human hepatoma cell lines (HepG2, Huh7, and SK-Hep-1) with half-maximal inhibitory concentration (IC50) values spanning 7.5-82.5 µmol·L-1. Artemdubinoid M (13) exhibited the most active cytotoxicity with IC50 values of 14.5, 7.5 and 8.9 µmol·L-1 against the HepG2, Huh7, and SK-Hep-1 cell lines, respectively, which were equivalent to the positive control, sorafenib.


Assuntos
Artemisia , Sesquiterpenos , Humanos , Artemisia/química , Sesquiterpenos/farmacologia , Sesquiterpenos/química , Linhagem Celular , Células Hep G2 , Cristalografia por Raios X , Estrutura Molecular
11.
Environ Toxicol ; 38(12): 3026-3042, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37661764

RESUMO

Ohwia caudata (Thunb.) H. Ohashi (Leguminosae) also called as "Evergreen shrub" and Artemisia argyi H.Lév. and Vaniot (Compositae) also named as "Chinese mugwort" those two-leaf extracts frequently used as herbal medicine, especially in south east Asia and eastern Asia. Anthracyclines such as doxorubicin (DOX) are commonly used as effective chemotherapeutic drugs in anticancer therapy around the world. However, chemotherapy-induced cardiotoxicity, dilated cardiomyopathy, and congestive heart failure are seen in patients who receive DOX therapy, with the mechanisms underlying DOX-induced cardiac toxicity remaining unclear. Mitochondrial dysfunction, oxidative stress, inflammatory response, and cardiomyocytes have been shown to play crucial roles in DOX-induced cardiotoxicity. Isoliquiritigenin (ISL, 10 mg/kg) is a bioactive flavonoid compound with protective effects against inflammation, neurodegeneration, cancer, and diabetes. Here, in this study, our aim is to find out the Artemisia argyi (AA) and Ohwia caudata (OC) leaf extract combination with Isoliquiritigenin in potentiating and complementing effect against chemo drug side effect to ameliorate cardiac damage and improve the cardiac function. In this study, we showed that a combination of low (AA 300 mg/kg; OC 100 mg/kg) and high-dose(AA 600 mg/kg; OC 300 mg/kg) AA and OC water extract with ISL activated the cell survival-related AKT/PI3K signaling pathway in DOX-treated cardiac tissue leading to the upregulation of the antioxidant markers SOD, HO-1, and Keap-1 and regulated mitochondrial dysfunction through the Nrf2 signaling pathway. Moreover, the water extract of AA and OC with ISL inhibited the inflammatory response genes IL-6 and IL-1ß, possibly through the NFκB/AKT/PI3K/p38α/NRLP3 signaling pathways. The water extract of AA and OC with ISL could be a potential herbal drug treatment for cardiac hypertrophy, inflammatory disease, and apoptosis, which can lead to sudden heart failure.


Assuntos
Artemisia , Cardiotoxicidade , Extratos Vegetais , Animais , Ratos , Apoptose , Artemisia/química , Cardiotoxicidade/tratamento farmacológico , Cardiotoxicidade/metabolismo , Doxorrubicina/toxicidade , Inflamação/induzido quimicamente , Inflamação/tratamento farmacológico , Inflamação/metabolismo , Miócitos Cardíacos , Fator 2 Relacionado a NF-E2/efeitos dos fármacos , Fator 2 Relacionado a NF-E2/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Fosfatidilinositol 3-Quinases/metabolismo , Proteínas Proto-Oncogênicas c-akt/metabolismo , Ratos Sprague-Dawley , Transdução de Sinais , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Heme Oxigenase-1/efeitos dos fármacos , Heme Oxigenase-1/metabolismo
12.
Arch Pharm Res ; 46(9-10): 782-794, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37770811

RESUMO

Artemongolins A-K (1-11), which are undescribed sesquiterpenoid dimers, were obtained from Artemisia mongolica and characterized through comprehensive spectral data, including HRESIMS, IR, 1D and 2D NMR, and ECD calculations. The absolute configurations of compounds 1, 4, and 7 were undoubtedly determined by a single-crystal X-ray crystallography. Artemongolins A-K (1-11) featured a rare 5/7/5/5/5/10 hexacyclic system composed of a germacrene and a guaianolide by a fused 2-oxaspiro[4,4]nonane-1-one ring system. Antihepatoma evaluation against three human hepatoma cell lines demonstrated that the most active compounds 5 and 6 displayed inhibitory activity with IC50 values of 88.6 and 57.0 (HepG2), 59.1 and 26.4 (Huh7), and 67.5 and 32.5 (SK-Hep-1) µM, respectively.


Assuntos
Artemisia , Sesquiterpenos , Humanos , Artemisia/química , Sesquiterpenos de Germacrano/farmacologia , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/farmacologia , Sesquiterpenos/farmacologia , Sesquiterpenos/química , Estrutura Molecular
13.
Phytochemistry ; 216: 113871, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37777165

RESUMO

Five undescribed eudesmane sesquiterpenoids, artemilavanins A-E, and one undescribed rearranged eudesmane sesquiterpenoid, artemilavanin F, were isolated from the 95% ethanol extract of the aerial parts of Artemisia lavandulaefolia DC., along with ten known compounds. The structures and configurations of undescribed compounds were mainly elucidated by spectroscopic analyses and single-crystal X-ray diffraction analysis. Among all isolated compounds, artemilavanin F exhibited inhibitory activity on PANC-1 pancreatic cancer cells with IC50 of 9.69 ± 2.39 µM. Artemilavanin F inhibited PANC-1 cell proliferation by induction of G2/M cell cycle arrest and apoptosis mediated by downregulation of cyclin-dependent kinases and accumulation of reactive oxygen species. Moreover, artemilavanin F inhibited the colony formation, cell migration and sphere formation of PANC-1 cells, indicating the suppression of stem-cell-like phenotype of PANC-1 cells. Further results confirmed that the expression of cancer stem cell markers such as Bmi1, CD44, CD133 were inhibited by artemilavanin F. Downregulation of epithelial-mesenchymal transition (EMT) markers such as N-cadherin and Oct-4 indicated the potential of artemilavanin F in prevention of metastasis.


Assuntos
Artemisia , Neoplasias Pancreáticas , Sesquiterpenos de Eudesmano , Sesquiterpenos , Artemisia/química , Neoplasias Pancreáticas/tratamento farmacológico , Sesquiterpenos de Eudesmano/farmacologia , Sesquiterpenos de Eudesmano/análise , Sesquiterpenos de Eudesmano/química , Componentes Aéreos da Planta/química , Sesquiterpenos/química , Estrutura Molecular , Neoplasias Pancreáticas
14.
Int J Biol Macromol ; 253(Pt 1): 126636, 2023 Dec 31.
Artigo em Inglês | MEDLINE | ID: mdl-37657565

RESUMO

Abuse of antibiotics has led to excessive amounts of antibiotic residues in food and environment, thus enhancing pathogenic bacterium resistance and threatening human health. Therefore, searching and developing safe and green antibiotic alternatives are necessary. In this study, an Artemisia argyi leaf polysaccharide (AALP) fraction was extracted and analyzed. Chemical composition analysis showed that the carbohydrate, uronic acid, protein, and polyphenol content in AALP were 68.3 % ± 4.13 %, 9.4 % ± 0.86 %, 1.79 % ± 0.27 %, and 0.16 % ± 0.035 %, respectively. Chromatographic results suggested that AALP contained rhamnose, arabinose, glucosamine, galactose, glucose, xylose, mannose, galacturonic acid, and glucuronic acid in a molar ratio of 9.26, 1.35, 1.18, 3.04, 48.51, 2.33, 31.26, 3.93, and 9.08; the weight average molecular weight, number average molecular weight, and polydispersity of AALP were 5.41 kDa, 4.63 kDa, and 1.168, respectively. Fourier transform infrared spectroscopy indicated that AALP constituted the polysaccharide-specific groups of CH, CO, and OH. Meanwhile, AALP showed a dose-dependent inhibitory effect on Staphylococcus aureus in the inhibition zone assay, and the minimal inhibitory concentration was 1.25 mg/mL. Furthermore, AALP disrupted the cell wall, depolarized the inner membrane potential, and inhibited the activities of succinate dehydrogenase and malate dehydrogenase in S. aureus.


Assuntos
Artemisia , Infecções Estafilocócicas , Humanos , Staphylococcus aureus , Polissacarídeos/química , Antibacterianos/química , Artemisia/química , Folhas de Planta/química
15.
Int J Biol Macromol ; 249: 126074, 2023 Sep 30.
Artigo em Inglês | MEDLINE | ID: mdl-37524276

RESUMO

Although Artemisia sphaerocephala krasch gum (ASKG) has attracted growing attention in the field of medical engineering and food industries, however, there are few studies on the gelation of ASKG. In this paper, acrylic acid modified ASKG hydrogels were prepared by radiation induced grafting, cross-linking and polymerization technique for the first time. The semi-IPN structure was prepared by the cross-linked ASKG network and poly-AAc dispersed within the network. The effects of the adsorbed dose on the swelling ratio and gel fraction were investigated. The different acrylic acid content modified ASKG hydrogels (ASKGAAc1 and ASKGAAc2) for methyl blue (MB) adsorption were investigated, and the ASKG hydrogels was also studied for comparison. The influence of pH, contact time, initial concentration, temperature, ion strength on MB adsorption were tested. The results showed that acrylic acid can promote the formation of hydrogel and greatly enhanced the adsorption of ASKG. The adsorption isotherms were well obeyed the Langmuir model, and the maximum adsorption capacity for MB of ASKG, ASKGAAc1 and ASKGAAc2 were 571.43, 1517.8 and 1654.9 mg/g, respectively. Moreover, the MB adsorption by ASKG based hydrogels was exothermic, spontaneous, and more favorable at lower temperature. Furthermore, the adsorption-desorption experiments demonstrated a good reusability of these hydrogels.


Assuntos
Artemisia , Poluentes Químicos da Água , Adsorção , Polimerização , Azul de Metileno/química , Hidrogéis/química , Artemisia/química , Concentração de Íons de Hidrogênio , Poluentes Químicos da Água/química , Cinética
16.
Fish Shellfish Immunol ; 140: 108962, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37488037

RESUMO

The popularity of intensive fish farming has led to the emergence of fish diseases characterized by hepatobiliary syndrome. Artemisia argyi (A. argyi) essential oils have anti-inflammatory and anti-oxidant effects. However, their alleviating effects and mechanism on liver disease in fish are still unclear. Thus, adult zebrafish were used to construct an animal model to observe histopathological damages, determine biochemical parameters and expression of inflammatory cytokines and mRNAs in the PPAR-γ/NF-κB pathway, and conduct 16 S sequencing of intestinal microbiota. The results found that after treatment with A. argyi essential oil, the histopathological damage caused by ethanol was relieved; the CAT, SOD, and GSH levels were remarkably elevated, while the MDA level was obviously lowered (P < 0.05); the expression levels of IL-10 and IFN-γ mRNAs were enhanced, but the levels of IL-1ß, IL-6, PPAR-γ, NF-κB, and TNF-α mRNAs were reduced (P < 0.05) relative to the EtOH group. A. argyi essential oil remarkably attenuated the damage to intestinal tissue structure, and elevated the levels of Muc2, ZO-1, Claudin-1, and Occludin mRNA (P < 0.05). Sequencing of the gut flora showed that A. argyi essential oil significantly altered the composition of gut microbes compared with the EtOH group. In addition, KEGG and COG analyses also showed significant (P < 0.05) changes in acetate cycling metabolism in the EtOH group, catechol 2, 3-dioxygenase and nitroreductase were significantly increased (P < 0.001), and lipid metabolism and terpenoid synthesis were significantly elevated (P < 0.001) in A. argyi essential oil group. The results indicate that A. argyi essential oil could effectively relieve ethanol-caused histopathological damage of livers by modulating the composition of gut microbiota, thus inhibiting the level of IL-1ß and mRNAs in the PPAR-γ/NF-κB pathway, increasing the IL-10 level, reducing the oxidative stress. This may offer a rationale for further research on the rationality of A. argyi as a substitute for feed antibiotics in aquaculture.


Assuntos
Artemisia , Hepatopatias , Óleos Voláteis , Animais , Peixe-Zebra/metabolismo , Óleos Voláteis/farmacologia , Interleucina-10 , NF-kappa B/metabolismo , Artemisia/química , Artemisia/metabolismo , Receptores Ativados por Proliferador de Peroxissomo , Etanol
17.
Phytochem Anal ; 34(5): 594-605, 2023 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-37282799

RESUMO

INTRODUCTION: Ssajuari-ssuk and sajabal-ssuk have many clinical benefits. It is difficult to discriminate between these two species based on general characteristics aside from the shapes of the leaves. Thus, species identification and quality control between ssajuari-ssuk and sajabal-ssuk are of great concern in plant science and clinical therapy. OBJECTIVE: The aim of this study is to determine whether fast gas chromatography with uncoated surface acoustic wave sensor (GC-SAW) can be a useful technique for performing species identification and quality control using volatile patterns of ssajuari-ssuk and sajabal-ssuk air-dried for 4 months and 2 years and 4 months. METHODOLOGY: Fast GC-SAW sensor provides second unit analysis, simple, on-line measurements that do not require pretreatment of the sample and rapid sensory information. Headspace solid-phase microextraction gas chromatography-mass spectrometry (HS-SPME-GC-MS) was employed to confirm the identification of the volatiles and compared to fast GC-SAW sensor. RESULTS: In air-dried sajabal-ssuk, the concentration of 1,8-cineole was higher than that in air-dried ssajuari-ssuk, while the level of α-thujone was considerably lower than that of air-dried ssajuari-ssuk. Each of ssajuari-ssuk and sajabal-ssuk air-dried for 4 months and 2 years and 4 months has its own characteristic volatile pattern owing to its individual chemotypes or chemical compositions. CONCLUSION: Consequently, the fast GC-SAW sensor can be a useful technique for species identification and quality control using volatile patterns of ssajuari-ssuk and sajabal-ssuk air-dried for 4 months and 2 years and 4 months. This method can be used for the standardisation of quality control using volatile patterns of herbal medicines.


Assuntos
Artemisia , Compostos Orgânicos Voláteis , Cromatografia Gasosa-Espectrometria de Massas/métodos , Artemisia/química , Som , Controle de Qualidade , República da Coreia , Compostos Orgânicos Voláteis/análise , Microextração em Fase Sólida/métodos
18.
J Biomater Sci Polym Ed ; 34(15): 2161-2178, 2023 10.
Artigo em Inglês | MEDLINE | ID: mdl-37368503

RESUMO

The anti-washout ability of calcium phosphate cement (CPC) determines the effectiveness of CPC in clinical application. The γ-ray irradiation method often used in the sterilization process of CPC products is easy to degrade some commonly polymer anti-washout agent, which greatly reduces its anti-washout performance. Artemisia sphaerocephala Krasch gum (ASKG) has the potential of radiation resistance and anti-washout, but no one has considered its performance as anti-washout agent of CPC and mechanism of radiation resistance and anti-washout so far. In this study, we report the effect of γ-ray on ASKG and the effectiveness of ASKG for enhancing of radiation resistance and anti-washout ability of CPC, the physical, chemical properties and in vitro cell behaviors of ASKG-CPCs were also investigated. The results showed that addition of ASKG before and after irradiation could significantly enhanced the anti-washout performance of CPC, which is differ from conventional anti-washout agents. Meanwhile, ASKG-CPCs had an excellent injectable property and biocompatibility, and low content of irradiated ASKG could promote bone differentiation well. We anticipate that the radiation-resistant and anti-washout ASKG-CPCs have potential application prospect in orthopaedic surgery.


Assuntos
Artemisia , Artemisia/química , Fosfatos de Cálcio/química , Cimentos Ósseos/química
19.
Environ Toxicol ; 38(10): 2416-2428, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37347548

RESUMO

The environmental pollutant bisphenol A (BPA), used in the manufacture of plastic packaging materials for various diets, is widely distributed in the environment and causes severe hepatotoxicity by inducing oxidative stress. Artemisia argyi essential oil (AAEO), a volatile oil component isolated from Artemisia argyi H.Lév. & Vaniot, has pharmacological effects, especially for hepatoprotective actions. However, the potential effect of AAEO in BPA induced hepatotoxicity has not been characterized. First, we analyzed the chemical composition in AAEO by gas chromatography-mass spectrometry. Herein, we investigated the effect of AAEO on hepatic metabolic changes in mice exposed to BPA. Results showed that compared with the BPA group, AAEO could reduce the level of liver function enzymes in BPA mice serum, and ameliorate hepatic lesions and fibrosis. Additionally, 20 differential metabolites screened by metabolomics were mainly involved in the reprogramming of glutathione metabolism, purine metabolism, and polyunsaturated fatty acid synthesis. Moreover, AAEO could reduce hepatic ferroptosis induced by BPA, as demonstrated by reducing xanthine oxidase activity, up-regulating the activities of glutathione peroxidase 4 (GPX4), superoxide dismutase, and catalase and the expression of SLC7A11 to promote the glutathione synthetic, while inhibiting transferrin receptor 1 (TFR1) expression to reduce the accumulation of Fe2+ in cells. Therefore, our study identified AAEO as a hepatic protectant against BPA-induced hepatotoxicity by reversing the occurrence of ferroptosis.


Assuntos
Artemisia , Doença Hepática Induzida por Substâncias e Drogas , Ferroptose , Óleos Voláteis , Camundongos , Animais , Artemisia/química , Óleos Voláteis/farmacologia , Glutationa , Doença Hepática Induzida por Substâncias e Drogas/prevenção & controle
20.
Phytochemistry ; 211: 113714, 2023 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-37156434

RESUMO

Bioassay-guided investigation of the active fraction of Artemisia princeps led to 13 undescribed sesquiterpenoid dimers, artemiprinolides A-M (1-13), together with 11 known ones (14-24). Their structures were elucidated by comprehensive spectroscopic data and absolute configurations were assigned based on single crystal X-ray diffraction data and ECD calculations. Structurally, all compounds were postulated to be derived from the Diels-Alder cycloaddition. The isolated dimers except 11 and 15 were assayed for their cytotoxicity against HepG2, Huh7, and SK-Hep-1 cell lines, of which four compounds (3, 13, 17, 18) exhibited obvious cytotoxicity with IC50 values ranging from 8.8 to 20.1 µM. Interestingly, the most active compounds 1 and 16 manifested significant cytotoxicity on the three tested hepatoma cell lines with IC50 values of 5.4, 4.1 (HepG2), 7.7, 5.6 (Huh7), and 11.8, 15.7 µM (SK-Hep-1), respectively, which were better than sorafenib. Compound 1 dose-dependently inhibited cell migration and invasion, and significantly induced the HepG2 cell arrest in G2/M phase by downregulating cdc2 and pcdc2 and upregulating cyclinB1; and induced apoptosis by downregulating Bcl-2 expression and upregulating Bax level. The molecular docking study implied that the carbonyl at the C-12' of 1 had a strong binding affinity with PRKACA.


Assuntos
Artemisia , Carcinoma Hepatocelular , Sesquiterpenos , Artemisia/química , Simulação de Acoplamento Molecular , Sesquiterpenos/química , Carcinoma Hepatocelular/tratamento farmacológico , Apoptose , Estrutura Molecular
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