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1.
Zhongguo Zhong Yao Za Zhi ; 46(15): 3846-3852, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34472258

RESUMO

The lignans in Urtica cannabina were isolated by preparative HPLC, silica, and ODS column chromatographies, and identified by NMR and HR-MS. The inhibitory activities on 5α-reductase were evaluated in vitro. As a result, ten secolignans,(2R,4S)-2,4-bis(3-methoxyl-4-hydroxyphenyl)-3-butoxypropanol(1), 3,4-trans-3-hydroxymethyl-4-[bis(3,4-dimethoxyphenyl)methyl] butyrolactone(2), 3,4-trans-3-hydroxymethyl-4-[(3,4-dimethoxyphenyl)(3-methoxyl-4-hydroxyphenyl)methyl] butyrolactone(3), 3,4-trans-3-hydroxymethyl-4-[bis(3-methoxyl-4-hydroxyphenyl)methyl] butyrolactone(trans urticol, 4), 3,4-trans-3-hydroxymethyl-4-[bis(3,4-dimethoxyphenyl)methyl] butyrolactone-3-O-ß-D-glucopyranoside(5), 3,4-trans-3-hydroxymethyl-4-[(3,4-dimethoxyphenyl)(3-methoxyl-4-hydroxyphenyl)methyl]butyrolactone-3-O-ß-D-glucopyranoside(6), 3,4-trans-3-hydroxymethyl-4-[bis(3-methoxyl-4-hydroxyphenyl)methyl]butyrolactone-3-O-ß-D-glucopyranoside(trans-urticol-7-O-ß-D-glucopyranoside, 7), cycloolivil-4-O-ß-D-glucopyranoside(8), isolariciresinol-4'-O-ß-D-glucopyranoside(9), and olivil-4'-O-ß-D-glucopyranoside(10), together with a polyphenol [α-viniferin(11)], were isolated from U. cannabina for the first time. Compound 1 was a new lignan. Compound 7 was potent in inhibiting 5α-reductase.


Assuntos
Colestenona 5 alfa-Redutase/farmacologia , Lignanas , Urticaceae , Inibidores de 5-alfa Redutase , Cromatografia Líquida de Alta Pressão , Lignanas/farmacologia , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Urticaceae/efeitos dos fármacos , Urticaceae/enzimologia
2.
Molecules ; 26(16)2021 Aug 08.
Artigo em Inglês | MEDLINE | ID: mdl-34443392

RESUMO

Thymic stromal lymphopoietin (TSLP) plays an important role in the pathophysiology of various allergic diseases that are mediated by T helper cell type-2 (Th2) responses, including asthma and atopic dermatitis. The primary focus of this study was the identification of potent inhibitors of the TSLP signaling pathway for potential therapeutic use. The 80% methanol extract of Machilus thunbergii bark significantly inhibited the signal transducer and activator of transcription 5 (STAT5) phosphorylation in human mast cell (HMC)-1 cells. Through activity-guided isolation, three lignans (1-3) were obtained and identified as (+)-galbelgin (1), meso-dihydroguaiaretic acid (2), and machilin A (3). Among them, two lignans (1 and 2) significantly inhibited STAT5 phosphorylation and TSLP/TSLPR interaction, as determined by ELISA. Our results indicated that lignans isolated from M. thunbergii are a promising resource for the treatment of allergic diseases.


Assuntos
Citocinas/antagonistas & inibidores , Lauraceae/química , Lignanas/farmacologia , Linhagem Celular , Fosforilação/efeitos dos fármacos , Casca de Planta/química , Fator de Transcrição STAT5/metabolismo , Células Th2/efeitos dos fármacos
3.
Adv Exp Med Biol ; 1330: 55-73, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34339030

RESUMO

Ovarian cancer, one of the three leading malignancies in women, has high incidence and mortality worldwide. It is hard to diagnose until very late stages and the 5-year survival rate is very low, due mostly to its distant metastasis. Chemotherapy is currently the most common treatment to inhibit cancer growth, but long-term use could result in resistance and tumor recurrence in addition to damages to normal tissues and functions of the patients. In order to achieve safe and curative effects against cancers, many investigators have focused their attention on traditional Chinese herbal medicines. Paclitaxel, a natural antitumor agent, has significant effects on advanced malignancies including ovarian cancer and is in the standard front-line treatment. Additional natural anticancer substances have continually been discovered for their high effectiveness and low side-effects in ovarian cancer prevention and therapy. In this chapter, we summarize recent work on a selected group of natural components, including lignans, ellagic acid, luteolin, mangiferin, and Acanthopanax senticosus, which have all been demonstrated to reduce the progress of epithelial ovarian cancer in a dose-depend manner, by both in vitro and in vivo experiments. The mechanisms of the anticancer activities by these natural components involve expression suppression of MMP2 and MMP9.


Assuntos
Antineoplásicos , Lignanas , Neoplasias Ovarianas , Antineoplásicos/uso terapêutico , Carcinoma Epitelial do Ovário , Feminino , Humanos , Lignanas/farmacologia , Lignanas/uso terapêutico , Recidiva Local de Neoplasia , Neoplasias Ovarianas/tratamento farmacológico
4.
Phytochemistry ; 191: 112905, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34392008

RESUMO

(+)-(2S,3S)- and (-)-(2R,3R)-Oxybaphuslactam A glucosides are two undescribed benzofuran ε-caprolactams featuring a unique 7/6/5 fused tricyclic framework with p-glucosyl-O-phenyl unit. They were isolated from the root of Tibetan medicinal plant Oxybaphus himalaicus along with an undescribed sucrose ester, 3-O-feruloyl sucrose, an undescribed lignan glucoside, (7'R,8R,8'S)-3,3',5,5'-tetramethoxy-7',9-epoxylignan-9'-ol-7-one 4,4'-di-O-ß-D-glucopyranoside and ten known amides and phenylpropanoid derivatives. Based on the spectral analyses, X-ray crystallography and comparison of experimental and TD-DFT calculated ECD spectra, the structures of these compounds were determined. The anti-inflammatory assay showed the undescribed compounds had significant inhibitory effects on the formation of NO, TNF-α and IL-6, which were evaluated by LPS induced RAW 264.7 cell model.


Assuntos
Benzofuranos , Caprolactama , Lignanas , Amidas , Anti-Inflamatórios/farmacologia , Benzofuranos/farmacologia , Glucosídeos/farmacologia , Lignanas/farmacologia , Estrutura Molecular
5.
Int J Mol Sci ; 22(15)2021 Jul 21.
Artigo em Inglês | MEDLINE | ID: mdl-34360535

RESUMO

The aims of this study were to develop the magnolol-chitosan films and study the positive effect of the combination of magnolol and chitosan. The addition of magnolol made the magnolol-chitosan films exhibit higher density (1.06-1.87 g/cm3), but the relatively lower water vapor permeability (12.06-7.36 × 10-11·g·m-1·s-1·Pa-1) and water content (16.10-10.64%). The dense and smooth surface and cross-section of magnolol-chitosan films were observed by environmental scanning electron microscopy (ESEM) images. The interaction of magnolol and chitosan was observed by X-ray diffraction (XRD), Fourier transform infrared (FTIR) spectroscopy and thermogravimetric analysis (TGA). After the addition of magnolol, the antioxidant capacity of magnolol-chitosan films was increased from 18.99 to 82.00%, the growth of P. aeruginosa was inhibited and the inhibition percentage of biofilm formation was increased from 30.89 to 86.04%. We further verified that the application of magnolol-chitosan films on chilled pork significantly reduced the increases in pH value, inhibited the growth of microorganisms and extended the shelf life. Results suggest that magnolol had a positive effect on magnolol-chitosan films and could be effectively applied to pork preservation.


Assuntos
Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Compostos de Bifenilo/farmacologia , Quitosana/química , Conservação de Alimentos/métodos , Lignanas/farmacologia , Infecções por Pseudomonas/tratamento farmacológico , Pseudomonas aeruginosa/efeitos dos fármacos , Animais , Anti-Inflamatórios não Esteroides/farmacologia , Embalagem de Alimentos/métodos , Carne de Porco/análise , Infecções por Pseudomonas/microbiologia , Suínos
6.
J Agric Food Chem ; 69(32): 9229-9237, 2021 Aug 18.
Artigo em Inglês | MEDLINE | ID: mdl-34357758

RESUMO

The dried leaves and rhizomes of Alpinia zerumbet have been traditionally used as food and medicine. Anti-inflammatory activity-guided phytochemical investigation into the rhizomes of A. zerumbet led to the isolation of 17 compounds including 10 neolignans (1-10, 1a, 1b, 2a, 2b, 3a, 3b, 4, and 5 are new compounds) and seven diarylheptanoids (11-17) in which 1-3 were three pairs of enantiomers. 4 was only one enantiomer and 5 was a racemic mixture. Compounds 1a, 1b, 2a, and 2b incorporated an 8',9'-dinorneolignan skeleton, which was rare in the lignan family. The planar structures of these compounds were elucidated by extensive analyses of spectroscopic data. The relative and absolute configurations were determined by the time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculation method. The 95% ethanol extract and ethyl acetate extract of A. zerumbet were found to show anti-inflammatory activity against croton oil-induced ear edema in mice with inhibition rates of 20.0 and 47.6% at a dose of 80 mg/kg, respectively. Bioassays showed that compounds 1a, 1b, 2a, 2b, and 12 moderately inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW264.7 cells with IC50 values of 3.62, 7.63, 6.51, 5.60, and 8.33 µM, respectively.


Assuntos
Alpinia , Lignanas , Animais , Anti-Inflamatórios/farmacologia , Diarileptanoides , Lignanas/farmacologia , Camundongos , Estrutura Molecular , Extratos Vegetais/farmacologia , Rizoma
7.
J Med Food ; 24(8): 825-832, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-34406878

RESUMO

Schisandra chinensis (S. chinensis) is one of the core drugs used for relieving cough and asthma in traditional Chinese medicine. However, there are few basic studies on the treatment of respiratory diseases with S. chinensis in modern pharmacology, and the material basis and mechanism of its antiasthmatic effect are still unclear. Lignans are the main active components of S. chinensis. The aim of this study was to observe the relaxation effect of S. chinensis lignans (SCL) on the tracheal smooth muscle of rats by in vitro tracheal perfusion experiments, and to explore the mechanism by preincubation with L-type calcium channel blocker verapamil, four potassium channel blockers glibenclamide, tetraethylamine, 4-aminopyridine and barium chloride (BaCl2), ß-adrenoceptor blocker propranolol, nitric oxide synthase inhibitor Nω-nitro-L-arginine methyl ester (L-NAME), and the cyclooxygenase inhibitor indomethacin, respectively. The results showed that SCL (0.25-1.75 mg/mL) reduced the contraction of isolated tracheal smooth muscle induced by acetylcholine, the preincubation with verapamil and glibenclamide could attenuate the relaxation effect, whereas propranolol, 4-aminopyridine, BaCl2, tetraethylamine, L-NAME, and indomethacin had no such effect. These results suggest that SCL has a significant relaxation effect on the isolated tracheal smooth muscle of rats, and the mechanism may be related to the inhibition of extracellular calcium influx and intracellular calcium release from the sarcoplasmic reticulum, as well as the activation of ATP-sensitive potassium channels. These findings may provide a pharmacological basis for the traditional use of S. chinensis to treat asthma.


Assuntos
Lignanas , Schisandra , Animais , Bloqueadores dos Canais de Cálcio/farmacologia , Lignanas/farmacologia , Relaxamento Muscular , Músculo Liso , Óxido Nítrico , Bloqueadores dos Canais de Potássio/farmacologia , Ratos
8.
Fitoterapia ; 153: 104993, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34284073

RESUMO

A new skeleton flavonoid, identified as (5aR)-10-hydroxy-8-methoxy-5aH,11H-chromeno[2,3-b]chromen-11-one (1), named oleracone G, and a new lignan, confirmed as 8-(4-hydroxy-3-methoxyphenyl)-3-methoxynaphthalen-2-ol (2), named oleralignan B, were isolated from Portulaca oleracea L., and the structures of them were determined using spectroscopic methods including UV, IR, 1D NMR, 2D NMR, and UHPLC-ESI-QTOF/MS. In addition, compounds 1-2 were applied to investigate the anti-inflammatory activities on lipopolysaccharide-stimulated macrophages and scavenging effects in 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radical. The results showed that the two compounds at 10 µM and 20 µM could dose-dependently decrease the secretion of interleukin 1ß in RAW 264.7 cells by enzyme-linked immunosorbent assay, moreover, presented remarkable antioxidant activities with IC50 values of 27.57, 20.12 µM, respectively.


Assuntos
Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Flavonoides/farmacologia , Lignanas/farmacologia , Portulaca/química , Animais , Anti-Inflamatórios/isolamento & purificação , Antioxidantes/isolamento & purificação , China , Flavonoides/isolamento & purificação , Lignanas/isolamento & purificação , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7
9.
Phytochemistry ; 190: 112893, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34332297

RESUMO

Four previously undescribed iridoid glycosides, including two bis-iridoid glycosides, and three undescribed lignans, together with 16 known analogues, were isolated from the fruits of Gardenia jasminoides Eills. Their structures were elucidated on basis of spectroscopic methods, and the absolute configurations of three of the unknown compounds were determined by interpretation of their electronic circular dichroic (ECD) and [α] [Formula: see text] data. The α-glucosidase inhibitory effects of the isolated compounds were evaluated and all the compounds exhibited slightly inhibitory activity with the values of IC50 greater than 50 µM.


Assuntos
Gardenia , Lignanas , Frutas , Glicosídeos/farmacologia , Glicosídeos Iridoides/farmacologia , Lignanas/farmacologia , Extratos Vegetais
10.
J Basic Clin Physiol Pharmacol ; 32(4): 809-815, 2021 Jun 25.
Artigo em Inglês | MEDLINE | ID: mdl-34214339

RESUMO

OBJECTIVES: Phyllanthus niruri has been known as an immunomodulator and also reported to possess an antiviral activity against several RNA viruses, such as hepatitis B virus and hepatitis C virus by inhibiting viral entry and replication. Since the current situation of Coronavirus Disease 2019 (COVID-19) which infected among the world and caused severe disease and high morbidity, it urgently needed to find new agents against COVID-19. Therefore, in silico screening against COVID-19 receptors is carried out as an initial stage of drug discovery by evaluating the activity of phyllanthin and hypophyllanthin, an isolated from Phyllanthus niruri, in inhibiting spike glycoprotein (6LZG) and main protease (5R7Y) which play as target receptors of COVID-19. METHODS: Molegro Virtual Docker 6.0 used to determine the best binding energy through the rerank score which shows the total energy bonds calculation. RESULTS: Phyllanthin and hypophyllanthin demonstrated to possess greater binding affinity toward the COVID-19 inhibition sites than their native ligand. The rerank score of phyllanthin and hypophyllanthin are lower than the native ligands 6LZG and 5R7Y. This result indicated that phyllanthin and hypophyllanthin have a stronger interaction than the native ligands both in spike glycoprotein (entry inhibitor) and main protease (translation and replication inhibitor). CONCLUSIONS: In conclusion, phyllanthin and hypophyllanthin are predicted to have strong activity against COVID-19 through inhibiting spike glycoprotein and main protease under in silico study. Further research is needed to support the development of P. niruri as inhibitor agents of COVID-19 through bioassay studies.


Assuntos
Lignanas/farmacologia , Phyllanthus/química , COVID-19/tratamento farmacológico , Simulação por Computador , Humanos , Ligantes , Lignanas/toxicidade , Simulação de Acoplamento Molecular , Estrutura Molecular , Extratos Vegetais/farmacologia , SARS-CoV-2/efeitos dos fármacos
11.
Molecules ; 26(11)2021 Jun 03.
Artigo em Inglês | MEDLINE | ID: mdl-34205154

RESUMO

The genus Curculigo, as a folk herbal medicine, has been used for many years in China, treating impotence, limb limpness, and arthritis of the lumbar and knee joints. The last systematic review of the genus Curculigo was written in 2013, scientifically categorizing the phytochemistry and biological activities. Hitherto, the original compounds and their pharmacological activities were presented as the development of this genus, but there is not an updated review. To conclude the progression of the genus Curculigo, we collected the new literature published from 2013 to 2021 in PubMed, Web of Science, Google Scholar databases, and the Chinese National Knowledge Infrastructure. The novel chlorophenolic glucosides, curculigine, phenolic glycosides, orcinosides and polysaccharides were isolated from Curculigo. The new analyzing methods were established to control the quality of Curculigo as a herbal medicine. In addition, the pharmacological effects of Curculigo focused on anti-diabetes, antibacterial, anti-inflammatory, osteoporosis, antioxidation, etc. The antitumor and neuroprotective activities were newly explored in recent years. The application of herbal medicine was gradually developed in scientific methods. The medicinal value of the genus Curculigo needs to further investigate its pharmacological mechanisms. This new review offers more insights into the exploitation of the pharmacological value of the genus Curculigo.


Assuntos
Curculigo/química , Compostos Fitoquímicos/química , Etnofarmacologia , Glucosídeos/química , Glucosídeos/farmacologia , Lignanas/química , Lignanas/farmacologia , Compostos Fitoquímicos/farmacologia , Polissacarídeos/química , Polissacarídeos/farmacologia
12.
Molecules ; 26(14)2021 Jul 06.
Artigo em Inglês | MEDLINE | ID: mdl-34299391

RESUMO

In the present study, the phytochemical study of the n-hexane extract from flowers of Nectandra leucantha (Lauraceae) afforded six known neolignans (1-6) as well as one new metabolite (7), which were characterized by analysis of NMR, IR, UV, and ESI-HRMS data. The new compound 7 exhibited potent activity against the clinically relevant intracellular forms of T. cruzi (amastigotes), with an IC50 value of 4.3 µM and no observed mammalian cytotoxicity in fibroblasts (CC50 > 200 µM). Based on the results obtained and our previous antitrypanosomal data of 50 natural and semi-synthetic related neolignans, 2D and 3D molecular modeling techniques were employed to help the design of new neolignan-based compounds with higher activity. The results obtained from the models were important to understand the main structural features related to the biological response of the neolignans and to aid in the design of new neolignan-based compounds with better biological activity. Therefore, the results acquired from phytochemical, biological, and in silico studies showed that the integration of experimental and computational techniques consists of a powerful tool for the discovery of new prototypes for development of new drugs to treat CD.


Assuntos
Produtos Biológicos/farmacologia , Doença de Chagas/tratamento farmacológico , Simulação por Computador , Descoberta de Drogas , Lauraceae/química , Lignanas/farmacologia , Tripanossomicidas/farmacologia , Animais , Fibroblastos/efeitos dos fármacos , Rim/efeitos dos fármacos , Macaca mulatta , Camundongos , Camundongos Endogâmicos BALB C , Compostos Fitoquímicos/farmacologia , Espécies Reativas de Oxigênio/metabolismo , Trypanosoma cruzi/efeitos dos fármacos
13.
Fitoterapia ; 153: 104990, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34246746

RESUMO

Three novel lignans (1, 5 and 6) and two novel quinic acids (16 and 17) along with 15 known phenylpropanoids were obtained from the ethanol extract of Zanthoxylum nitidum var. tomentosum (Rutaceae). Their structures were confirmed by comprehensive spectroscopic data (NMR and HRESIMS), and the absolute configurations of all novel compounds were elucidated based on electronic circular dichroism (ECD) spectroscopic data. The production of nitric oxide (NO) in BV-2 microglial cells induced through lipopolysaccharide (LPS) was used to evaluate in vitro anti-neuroinflammatory activity of compounds 1-20. Compound 2, 3, 7 and 16 showed excellent inhibition of LPS-induced NO production. The structure-activity relationships of the isolates were investigated. In addition, the mechanism of action of 2 was elucidated by RT-PCR and Western blotting analysis, which indicated that it reduced neuroinflammatory mainly through NLRP3/caspase1 signaling pathways in LPS-induced BV2 microglial cells.


Assuntos
Anti-Inflamatórios/farmacologia , Lignanas/farmacologia , Microglia/efeitos dos fármacos , Zanthoxylum/química , Animais , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular , China , Lignanas/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Transdução de Sinais/efeitos dos fármacos
14.
Artigo em Inglês | MEDLINE | ID: mdl-34274605

RESUMO

Lignans from Schisandra chinensis (Turcz.) Baill (LFS) has been proved to improve impaired cognitive ability thereby show potential in treating Alzheimer's disease (AD). In this study, UHPLC-Q-TOF-MS and UHPLC-QQQ-MS were adopted cooperatively to establish a method synchronously detecting 10 kinds of LFS monomers in rat plasma samples. And this method was further applied for pharmacokinetic study to compare the metabolism of LFS in normal and AD rats. The results indicated that AD rats showed an observably better absorption of LFS compared to normal rats. Based on time-varying plasma concentration of LFS, metabolomics was used to establish a plasma concentration-time-endogenous metabolite connection. In total 54 time-varying endogenous metabolites were screened and most of which were closely associated with AD. And LFS exerted a concentration dependent regulating effect to most of these metabolites. Through biomarker related pathways and biological function analysis, LFS might treat AD through neuroprotection, antioxidant damage and regulating the metabolism of unsaturated fatty acids. This is the first study connecting LFS absorbtion and endogenous metabolite changes with the time lapse. The pharmacokinetics and metabolic profile differences between normal and AD rats were firstly investigated as well. This study provides a novel perspective in exploring the effect and mechanism of LFS in treating AD.


Assuntos
Doença de Alzheimer/metabolismo , Lignanas , Metaboloma/efeitos dos fármacos , Extratos Vegetais , Schisandra/química , Animais , Cromatografia Líquida de Alta Pressão , Modelos Animais de Doenças , Lignanas/farmacocinética , Lignanas/farmacologia , Masculino , Espectrometria de Massas , Metabolômica , Extratos Vegetais/farmacocinética , Extratos Vegetais/farmacologia , Ratos , Ratos Wistar
15.
Phytomedicine ; 88: 153609, 2021 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-34126414

RESUMO

BACKGROUD: Schisandra chinensis, a traditional Chinese medicine for liver protection, can significantly improve liver fibrosis. However, it is still unclear which active components in Schisandra chinensis play an anti-fibrosis role. PURPOSE: The purpose of present study was to observe the anti-fibrosis effect of schisantherin A (SCA) on liver fibrosis and explore its underlying mechanism. METHODS: The liver fibrosis model of mice was constructed by the progressive intraperitoneal injection of thioacetamide (TAA), and SCA (1, 2, and 4 mg/kg) was administered by gavage for 5 weeks. The biochemical indicators and inflammatory cytokines were measured, changes in the pathology of the mice liver were observed by hematoxylin & eosin (H&E) and Masson stainings for studying the anti-fibrosis effect of SCA. A hepatic stellate cell (HSCs) activation model induced by transforming growth factor-ß1 (TGF-ß1) was established, and the effect of SCA on the HSCs proliferation was observed by MTT assay. The expressions of target proteins related to transforming growth factor-ß-activated kinase 1 (TAK1)/mitogen-activated protein kinase (MAPK) and nuclear factor-κB (NF-κB) pathways were evaluated by western blotting, immunohistochemistry or immunofluorescence analysis, to explore the potential mechanism of SCA. RESULTS: SCA could significantly ameliorate the pathological changes of liver tissue induced by TAA, and reduce the serum transaminase level, the hydroxyproline level and the expression of α-smooth muscle actin (α-SMA) and collagen 1A1 (COL1A1) proteins in the liver tissue. SCA could significantly lower the levels of tumor necrosis factor-α (TNF-α), interleukin-1ß (IL-1ß) and interleukin-6 (IL-6) in the serum and liver tissue, and down-regulate the expression of target proteins related to TAK1/MAPK and NF-κB pathways in the liver tissue. The in vitro studies demonstrated that SCA significantly inhibited the proliferation and activation of HCS-T6 cells induced by TGF-ß1, decreased TNF-α and IL-6 levels, and inhibited the TAK1 activation induced by TGF-ß1 and then the expression of MAPK and NF-κB signaling pathway-related proteins. CONCLUSION: Together, SCA can ameliorate the liver fibrosis induced by TAA and the HSC-T6 cell activation induced by TGF-ß1 in mice, and its mechanism may be to inhibit the HSCs activation and inflammatory response by inhibiting TGF-ß1 mediated TAK1/MAPK and signal pathways.


Assuntos
Ciclo-Octanos/farmacologia , Dioxóis/farmacologia , Lignanas/farmacologia , Cirrose Hepática/tratamento farmacológico , Cirrose Hepática/metabolismo , Fator de Crescimento Transformador beta1/metabolismo , Animais , Linhagem Celular , Citocinas/metabolismo , Células Estreladas do Fígado/efeitos dos fármacos , Cirrose Hepática/patologia , MAP Quinase Quinase Quinases/metabolismo , Masculino , Camundongos Endogâmicos ICR , Proteínas Quinases Ativadas por Mitógeno/metabolismo , NF-kappa B/metabolismo , Ratos , Transdução de Sinais/efeitos dos fármacos , Tioacetamida/toxicidade
16.
Fitoterapia ; 153: 104949, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34087408

RESUMO

Illicium difengpi is well-known as its stem barks that have been widely used in the Traditional Chinese Medicine (TCM) for therapy rheumatoid arthritis and traumatic injury. To comprehensive utilization of resources, the phytochemical investigation on the branches and leaves of this plant was carried out, which led to the isolation of an undescribed neolignan along with three known lignans. Their structures were elucidated on the basis of extensive spectroscopic data and the new compound was elucidated as a neolignan possessing a dihydropyran ring formed by a unique conjugation way and named difengpienol C. Difengpienol C showed the strongest anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 cells, which powerfully inhibited nitric oxide (NO), interleukin 6 (IL-6), tumor necrosis factor α (TNF-α) production and suppressed the mRNA transcription of inducible nitric oxide synthase (iNOS), IL-6 and TNF-α. Besides, difengpienol C blocked the activation of TLR4/MyD88/NF-κB signaling pathway. Therefore, difengpienol C might be a potent agent for anti-inflammatory drug development, and the non-traditional medicinal parts of Illicium difengpi can be identified as the source of natural anti-inflammatory molecules.


Assuntos
Anti-Inflamatórios/farmacologia , Illicium/química , Lignanas/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , China , Interleucina-6 , Lignanas/isolamento & purificação , Camundongos , Estrutura Molecular , NF-kappa B , Óxido Nítrico , Óxido Nítrico Sintase Tipo II , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Plantas Medicinais/química , Células RAW 264.7 , Transdução de Sinais , Receptor 4 Toll-Like , Fator de Necrose Tumoral alfa
17.
Fitoterapia ; 153: 104972, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34147546

RESUMO

A detailed phytochemical investigation of the leaves of the Australian rainforest tree Eupomatia laurina, led to the discovery of five new neolignans, eupomatenes A - E and eight known compounds, eupomatenoid-2, trans-(2'S)-2-[1'-(4-methoxyphenyl)prop-2'-yl]anethol, chlorogenic acid, chlorogenic acid-methyl ester, tyrosol-1-O-ß-xylopyranosyl-1(1 â†’ 6)-O-ß-glucopyranoside, leucoside, kaempferol-3-O-neohesperidoside, and pachypodol. The structures of all the compounds were determined by detailed spectroscopic analysis. All compounds were also evaluated for their anti-inflammatory properties by assessing their inhibitory effects on nitric oxide (NO) production and TNF- α release in RAW 264.7 macrophages. Whilst slight anti-inflammatory activity (in terms of inhibition of NO production) was observed with eupomatenes A - E, this was also associated with high levels of cell growth inhibition.


Assuntos
Anti-Inflamatórios/farmacologia , Lignanas/farmacologia , Magnoliopsida/química , Animais , Anti-Inflamatórios/isolamento & purificação , Lignanas/isolamento & purificação , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Queensland , Células RAW 264.7 , Fator de Necrose Tumoral alfa
18.
Zhongguo Zhong Yao Za Zhi ; 46(8): 2072-2078, 2021 Apr.
Artigo em Chinês | MEDLINE | ID: mdl-33982522

RESUMO

The chemical constituents from the extract of the twigs of Euscaphis konishii with anti-hepatoma activity were investigated, twelve compounds by repeated chromatography with silica gel, Sephadex LH-20 and preparative-HPLC. The structures of the chemical components were elucidated by spectroscopy methods, as konilignan(1),(7R, 8S)-dihydrodehydrodico-niferylalcohol-9-O-ß-D-glucopyranoside(2),illiciumlignan B(3),threo-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-panediol(4),erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-panediol(5), matairesinol(6), wikstromol(7), isolariciresinol(8),(+)-lyoniresinol(9), 4-ketopinoresinol(10), syringaresin(11), and vladinol D(12). Among them, compound 1 is a new lignan. Compounds 10 and 12 had moderate inhibitory activity on HepG2 cells, with IC_(50) values of 107.12 µmol·L~(-1) and 183.56 µmol·L~(-1), respectively.


Assuntos
Lignanas , Cromatografia Líquida de Alta Pressão , Lignanas/farmacologia , Extratos Vegetais/farmacologia
19.
J Org Chem ; 86(10): 7092-7106, 2021 05 21.
Artigo em Inglês | MEDLINE | ID: mdl-33979157

RESUMO

The oxygen in the benzofuran (BF) of three antiproliferative natural neolignans, salvinal (1), obovaten (2), and 2-[7-methoxy-2-(4-methoxyphenyl)-3-methylbenzofuran-5-yl]ethanol (3), was replaced with sulfur to form the new biological scaffold benzothiophene (BT) thio-lignans 4-6. Compounds 1-6 and 18 synthesized derivatives were evaluated for antiproliferative activity against five human cancer cell lines, including a multidrug-resistant cell line. Thio-salvinal (4) displayed significant antiproliferative effects with half-maximal inhibitory concentration (IC50) values of 0.57-0.95 µM against all tested cell lines, except for the HER2 negative breast cancer cell line MCF-7. This thio-lignan was 6.5-9.4 times more potent than parent 1. However, the related thio-lignans, 5 and 6, showed much weaker antiproliferative effects than 4 and were less potent than the parent natural benzofuran lignans 2 and 3. Newly synthesized thio-lignan 33 affected cell cycle progression at 24 and 48 h in the G2/M transition and S phase, respectively, as well as promoted sub-G1 induction by stimulating microtubule depolymerization and nuclear fragmentation. Since a highly reactive aldehyde in salvinal is generally not appropriate for drug development, we have successfully found nonaldehyde derivative 33 showing biological activity similar to salvinal by replacing BF with BT and an aldehyde with 1,3-dioxolane.


Assuntos
Antineoplásicos , Benzofuranos , Lignanas , Aldeídos/farmacologia , Antineoplásicos/farmacologia , Benzofuranos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lignanas/farmacologia , Relação Estrutura-Atividade
20.
Food Chem ; 360: 130063, 2021 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-34029927

RESUMO

Here, we detail the biomineralization-assisted separation and concentration of crude food extract and an evaluation of its effectiveness. Schisandra chinensis fruit extract was used as a model plant extract. Hybrid grape-like mineral was assembled by calcium carbonate mineralization. The hybrid particles of S. chinensis mineral were fully characterized using field emission scanning electron microscopy, X-ray diffraction, thermogravimetric analysis, and particle size analysis. Data including the Brunauer-Emmett-Teller surface area, single point total pore volume, and adsorption/desorption analysis of pore size were also investigated. Organic molecules, including lipids such as palmitic acid, stearic acid, and linolenic acid in the Schisandra chinensis fruit, affect the formation of complex structures involving the CaCO3 mineralization pathway by inhibiting crystallization. However, the cosmetic active primary components were entrapped in a similar proportion in the preserved extract, and were efficiently separated without additional filtering and concentration steps for purification. In addition, the hybrid mineral was enriched (10.5 times) in Gomisin N, a representative component of S. chinensis fruit, relative to its concentration in the initial extract samples. The hybrid mineral inhibited both intracellular and extracellular melanin production and increased the 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity. The data provide the first evidence of the potential use of fruit extract for obtaining hybrid minerals and the effectiveness of the biomineralization-based separation and concentration strategy.


Assuntos
Extratos Vegetais/química , Schisandra/química , Animais , Antioxidantes/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Ciclo-Octanos/química , Ciclo-Octanos/isolamento & purificação , Ciclo-Octanos/farmacologia , Frutas/química , Frutas/metabolismo , Lignanas/química , Lignanas/isolamento & purificação , Lignanas/farmacologia , Camundongos , Extratos Vegetais/farmacologia , Compostos Policíclicos/química , Compostos Policíclicos/isolamento & purificação , Compostos Policíclicos/farmacologia , Schisandra/metabolismo
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