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1.
Environ Res ; 246: 118004, 2024 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-38145732

RESUMO

The colonization of pathogenic microbes poses a significant clinical barrier that hinders the physiological wound-healing process. Addressing this challenge, we developed a novel wound dressing using a modified cotton gauze dressing coated with fucoidan and functionalized with silver nanoparticles (LB-Ag NPs-FN-OCG) for the rapid treatment of infected wounds. Firstly, phytochemical-capped LB-Ag NPs were synthesized and characterized using high performance liquid chromatography (HPLC), transmission electron microscopy (TEM), and zeta potential analysis. Secondly, different concentrations of LB-Ag NPs (0.1%-1%) were functionalized into FN-OCG to identify appropriate concentrations that were non-toxic with superior antibacterial activities. Screening assays, including antibacterial, hemolysis, chick chorioallantoic membrane (CAM) assay, and cytotoxicity assay, revealed that LB-Ag NPs (0.5%)-FN-OCG were non-toxic and demonstrated greater efficiency in inhibiting bacterial pathogens (Escherichia coli, Salmonella enterica, Staphylococcus aureus, and Listeria monocytogenes) and promoting fibroblast cell (NIH3T3) migration. In vivo assays revealed that LB-Ag NPs (0.5%)-FN-OCG treatment exhibited excellent wound healing activity (99.73 ± 0.01%) compared to other treatments by inhibiting bacterial colonization, maintaining the blood parameters, developing granulation tissue, new blood vessels, and collagen deposition. Overall, this study highlights that LB-Ag NPs (0.5%)-FN-OCG serve as a antibacterial wound dressing for infected wound healing applications.


Assuntos
Nanopartículas Metálicas , Polissacarídeos , Prata , Camundongos , Animais , Prata/química , Nanopartículas Metálicas/química , Células NIH 3T3 , Cicatrização , Antibacterianos/farmacologia , Bandagens
2.
Environ Res ; 242: 117600, 2024 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-37939806

RESUMO

Dichlorvos (2,2-Dichlorovinyl dimethyl phosphate, [DDVP]) belongs to the class of organophosphates and is widely used as an insecticide in agriculture farming and post-harvest storage units. Extensive research has been conducted to assess the factors responsible for the presence of DDVP in terrestrial and aquatic ecosystems, as well as the entire food chain. Numerous studies have demonstrated the presence of DDVP metabolites in the food chain and their toxicity to mammals. These studies emphasize that both immediate and chronic exposure to DDVP can disrupt the host's homeostasis, leading to multi-organ damage. Furthermore, as a potent carcinogen, DDVP can harm aquatic systems. Therefore, understanding the contamination of DDVP and its toxicological effects on both plants and mammals is vital for minimizing potential risks and enhancing safety in the future. This review aimed to comprehensively consolidate information about the distribution, ecological effects, and health impacts of DDVP, as well as its metabolism, detection, prevention, and remediation strategies. In summary, this study observes the distribution of DDVP contaminations in vegetables and fruits, resulting in significant toxicity to humans. Although several detection and bioremediation strategies are emerging, the improper application of DDVP and the alarming level of DDVP contamination in foods lead to human toxicity that requires attention.


Assuntos
Diclorvós , Inseticidas , Compostos Organofosforados , Animais , Humanos , Diclorvós/toxicidade , Diclorvós/metabolismo , Ecossistema , Inseticidas/toxicidade , Mamíferos/metabolismo
3.
Biosci Biotechnol Biochem ; 88(10): 1127-1135, 2024 Sep 20.
Artigo em Inglês | MEDLINE | ID: mdl-38964835

RESUMO

Seven new oleanane-type triterpene saponins, lysimaponins A-G, were isolated from aerial parts of Lysimachia laxa Baudo. Their chemical structures have been elucidated by analysis of spectroscopic and chemical methods. All compounds were evaluated for their antibacterial effects against Microcystis aeruginosa, Vibrio parahaemolyticus, V. harveyi, V. vulinificus, V. cholerae, and V. alginolyticus. All compounds showed potent antibacterial activities against the cyanobacteria M. aeruginosa with IC50 values ranging from 14.4 ± 1.2 to 35.3 ± 2.2 µg/mL. Compounds 1, 2, 4-7 inhibited V. parahaemolyticus with MIC values ranging from 64 to 256 µg/mL. The results suggested that saponins from L. laxa could be potential anti-cyanobacteria agents.


Assuntos
Antibacterianos , Testes de Sensibilidade Microbiana , Ácido Oleanólico , Primulaceae , Saponinas , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Saponinas/farmacologia , Saponinas/química , Saponinas/isolamento & purificação , Primulaceae/química , Ácido Oleanólico/farmacologia , Ácido Oleanólico/química , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/isolamento & purificação , Microcystis/química , Lysimachia
4.
Chem Biodivers ; : e202401024, 2024 Aug 23.
Artigo em Inglês | MEDLINE | ID: mdl-39177326

RESUMO

Phytochemical investigation of the methanol extract of the aerial parts of Lysimachia laxa led to the isolation of four new oleanane-type saponins, lysimosides A-D (1-4) and one known compound, lysimachigenoside B (5). Their structures were elucidated using a combination of HR-ESI-MS, 1D and 2D-NMR spectral data, chemical methods, and comparison with previous literature. The cytotoxic activity of these compounds was evaluated against human lung cancer (A-549) and human breast cancer (MCF-7) cell lines. All compounds exhibited cytotoxic activity against A-549 and MCF-7 cell lines with IC50 values ranging from 6.1 to 16.0 µM, comparable to the positive control, mitoxantrone. Interestingly, oleanane-type saponins with an acetyl group (2-4) exhibited increased cytotoxic activities compared to those without an acetyl group (1).

5.
Chem Biodivers ; : e202400896, 2024 Jun 22.
Artigo em Inglês | MEDLINE | ID: mdl-39140809

RESUMO

This study investigates Symplocos cochinchinensis (Lour.) S. Moore leaves and stems, commonly known as Symplocos, a plant indigenous to Asia renowned for its traditional use in holistic medicine. A comprehensive phytochemical analysis of S. cochinchinensis led to the isolation of two new lignans, namely symplolignans A and B (1 and 2) along with eleven known lignan glucosides: nortrachelogenin 4-O-ß-D-glucopyranoside (3), nortracheloside (4), matairesinol 4-O-ß-D-glucopyranoside (5), lariciresinol 4'-O-ß-D-glucopyranoside (6), balanophonin 4-O-ß-D-glucopyranoside (7), dehydrodiconiferyl alcohol 4-O-ß-D-glucopyranoside (8), dehydrodiconiferyl alcohol γ'-O-ß-D-glucopyranoside (9), 3-(ß-D-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofura (10), and pinoresinol 4'-O-ß-D-glucopyranoside (11). Their chemical structures were elucidated using 1D- and 2D-NMR, mass spectrometry, and their spectroscopic data were compared with those reported in literatures. Furthermore, all compounds were evaluated for their hepatoprotective effects using the Resazurin reduction assay in HepG2 hepatocellular carcinoma cells. Compounds 1, 5, 7, and 8 exhibited notable hepatoprotective efficacy, with cell viability ranging from 105.0±2.6 to 109.2±3.3 at a concentration of 10 µM. This research highlights the therapeutic potential of these compounds and enhanced to the understanding of lignans and neolignans in liver cell proliferation.

6.
J Asian Nat Prod Res ; : 1-7, 2024 Jun 13.
Artigo em Inglês | MEDLINE | ID: mdl-38869195

RESUMO

One new bithiophene derivative, 5-(but-3-en-1-yn-1-yl)-5'-(methoxymethyl)-2,2'-bithiophene (1), along with twelve known compounds, senecioester (2), tiglinsaureester (3), 5-acetoxymethyl-2'-(but-3-en-1-yn-1-yl)-2,5'-bithiophene (4), 5-(4-isovaleroyloxybut-1-ynyl)-2,2'-bithiophene (5), 5-hydroxymethyl-(2,5':2',5'')-terthienyl tiglate (6), 5-hydroxymethyl-(2,5':2',5'')-terthienyl agelate (7), 5- hydroxymethyl-2,5':2',5''-terthiophene dimethylacrylate (8), 5-methoxymethyl-2,2':5',2''-terthiophene (9), α-terthiophene (10), 1,3,8,9-tetrahydroxycoumestan 3-sulfate (11), demethylwedelolactone (12), and wedelolactone (13) were isolated from the methanol extract of aerial parts of Eclipta prostrata (L.) L. All isolated compounds were evaluated for the protective ability on the HepG2 cells. At the concentration of 100 µM, compounds 11-13 showed the highest hepatoprotective effects, with HepG2 cell viability ranging from 38.68% to 48.54%. Bithiophenes showed higher hepatoprotective cell viability than terthiophenes.

7.
Chem Biodivers ; 20(11): e202301296, 2023 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-37842907

RESUMO

Vitex trifolia L. is a medicinal plant and widely distributed in the northern mountainous areas of Vietnam. Phytochemical study on the fruits of this plant led to the isolation of nine iridoid derivatives (1-9) including three undescribed compounds (1-3). Their structures were elucidated to be 3''-hydroxyscrophuloside A1 (1), 3''-hydroxycallicoside D (2), 2'-p-hydroxybenzoylaucubin (3), 6'-p-hydroxybenzoylmussaenosidic acid (4), nishindaside (5), agnuside (6), 10-O-vanilloylaucubin (7), 6'-O-p-hydroxybenzoyl-gardoside (8), and buddlejoside B (9) based on extensive analyses of HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1, 2, 4, and 8 significantly posessed anti-barterial activity against Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa strains with MIC values in range of 16-64 µg/mL. At concentration of 20 µM, compounds 1-9 did not show cytotoxic effects against human lung cancer cells (PC9).


Assuntos
Anti-Infecciosos , Antineoplásicos , Vitex , Humanos , Iridoides/química , Vitex/química , Frutas/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/análise , Extratos Vegetais/análise
8.
J Asian Nat Prod Res ; 25(1): 18-26, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-35306942

RESUMO

Three new chromanes, malloapeltas J-L (1-3), and one new flavone C-glycoside, malloflavoside (4), together with four known compounds, apigenin 6-C-ß-D-xylopyranosyl-8-C-α-L-arabinopyranoside (5), apigenin 6-C-ß-D-glucopyranosyl-8-C-α-L-arabinopyranoside (6), apigenin 7-O-ß-D-apiofuranosyl-(1→2)-ß-D-glucopyranoside (7), and acantrifoside E (8) were isolated from the methanol extract of the leaves of Mallotus apelta. Their chemical structures were determined using spectroscopic methods, including 1D, 2D NMR, and HR-ESI-MS methods. All the isolated compounds were evaluated their cytotoxic activity against human prostate cancer (PC-3) and human breast cancer (MCF-7) cells, but none of them showed cytotoxicities on both human cancer cell lines.


Assuntos
Flavonas , Mallotus (Planta) , Humanos , Apigenina , Glicosídeos/farmacologia , Glicosídeos/química , Flavonas/farmacologia
9.
Molecules ; 27(17)2022 Aug 24.
Artigo em Inglês | MEDLINE | ID: mdl-36080161

RESUMO

Growth and maintenance of skeletal muscle is essential for athletic performance and a healthy life. Stimulating the proliferation and differentiation of muscle cells may help prevent loss of muscle mass. To discover effective natural substances enabling to mitigate muscle loss without side effects, we evaluated muscle growth with several compounds extracted from Catalpa bignonioides Walt. Among these compounds, pinoresinol and vanillic acid increased C2C12, a mouse myoblast cell line, proliferation being the most without cytotoxicity. These substances activated the Akt/mammalian target of the rapamycin (mTOR) pathway, which positively regulates the proliferation of muscle cells. In addition, the results of in silico molecular docking study showed that they may bind to the active site of insulin-like growth factor 1 receptor (IGF-1R), which is an upstream of the Akt/mTOR pathway, indicating that both pinoresinol and vanillic acid stimulate myoblast proliferation through direct interaction with IGF-1R. These results suggest that pinoresinol and vanillic acid may be a natural supplement to improve the proliferation of skeletal muscle via IGF-1R/Akt/mTOR signaling and thus strengthen muscles.


Assuntos
Proteínas Proto-Oncogênicas c-akt , Ácido Vanílico , Animais , Proliferação de Células , Furanos , Fator de Crescimento Insulin-Like I/metabolismo , Lignanas , Mamíferos/metabolismo , Camundongos , Simulação de Acoplamento Molecular , Músculo Esquelético/metabolismo , Mioblastos/metabolismo , Proteínas Proto-Oncogênicas c-akt/metabolismo , Transdução de Sinais , Serina-Treonina Quinases TOR/metabolismo , Ácido Vanílico/metabolismo , Ácido Vanílico/farmacologia
10.
Int J Mol Sci ; 22(17)2021 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-34502415

RESUMO

We investigated whether isoleucilactucin, an active constituent of Ixeridium dentatum, reduces inflammation caused by coal fly ash (CFA) in alveolar macrophages (MH-S). The anti-inflammatory effects of isoleucilactucin were assessed by measuring the concentration of nitric oxide (NO) and the expression of pro-inflammatory mediators in MH-S cells exposed to CFA-induced inflammation. We found that isoleucilactucin reduced CFA-induced NO generation dose-dependently in MH-S cells. Moreover, isoleucilactucin suppressed CFA-activated proinflammatory mediators, including cyclooxygenase-2 (COX2) and inducible NO synthase (iNOS), and the proinflammatory cytokines such as interleukin-(IL)-1ß, IL-6, and tumor necrosis factor (TNF-α). The inhibiting properties of isoleucilactucin on the nuclear translocation of phosphorylated nuclear factor-kappa B (p-NF-κB) were observed. The effects of isoleucilactucin on the NF-κB and mitogen-activated protein kinase (MAPK) pathways were also measured in CFA-stimulated MH-S cells. These results indicate that isoleucilactucin suppressed CFA-stimulated inflammation in MH-S cells by inhibiting the NF-κB and MAPK pathways, which suggest it might exert anti-inflammatory properties in the lung.


Assuntos
Anti-Inflamatórios/farmacologia , Asteraceae/química , Cinza de Carvão/toxicidade , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Macrófagos Alveolares/metabolismo , NF-kappa B/metabolismo , Compostos Fitoquímicos/farmacologia , Animais , Anti-Inflamatórios/química , Linhagem Celular , Inflamação/induzido quimicamente , Inflamação/tratamento farmacológico , Inflamação/metabolismo , Inflamação/patologia , Macrófagos Alveolares/patologia , Camundongos , Compostos Fitoquímicos/química
11.
Int J Mol Sci ; 22(5)2021 Feb 25.
Artigo em Inglês | MEDLINE | ID: mdl-33669060

RESUMO

Chinese chive (Allium tuberosum) is a medicinal food that is cultivated and consumed mainly in Asian countries. Its various phytochemicals and physiological effects have been reported, but only a few phytochemicals are available for skeletal muscle cell proliferation. Herein, we isolated a new compound, kaempferol-3-O-(6″-feruloyl)-sophoroside (1), along with one known flavonoid glycoside (2) and six amino acid (3-8) compounds from the water-soluble fraction of the shoot of the Chinese chive. The isolated compounds were identified using extensive spectroscopic methods, including 1D and 2D NMR, and evaluated for their proliferation activity on skeletal muscle cells. Among the tested compounds, newly isolated flavonoid (1) and 5-aminouridine (7) up-regulated PI3K/Akt/mTOR pathways, which implies a positive effect on skeletal muscle growth and differentiation. In particular, compound 1 down-regulated the Smad pathways, which are negative regulators of skeletal muscle growth. Collectively, we suggest that major constituents of Chinese chive, flavonoids and amino acids, might be used in dietary supplements that aid skeletal muscle growth.


Assuntos
Proliferação de Células/efeitos dos fármacos , Cebolinha-Francesa/química , Músculo Esquelético/efeitos dos fármacos , Fosfatidilinositol 3-Quinases/metabolismo , Compostos Fitoquímicos/farmacologia , Proteínas Proto-Oncogênicas c-akt/metabolismo , Serina-Treonina Quinases TOR/metabolismo , Aminoácidos/análise , Aminoácidos/química , Aminoácidos/farmacologia , Animais , Diferenciação Celular/efeitos dos fármacos , Linhagem Celular , Cromatografia Líquida , Suplementos Nutricionais/análise , Flavonoides/análise , Flavonoides/química , Flavonoides/farmacologia , Quempferóis/análise , Quempferóis/química , Quempferóis/farmacologia , Espectrometria de Massas , Camundongos , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/análise , Extratos Vegetais/farmacologia , Transdução de Sinais/efeitos dos fármacos , Análise Espectral
12.
Molecules ; 26(2)2021 Jan 12.
Artigo em Inglês | MEDLINE | ID: mdl-33445612

RESUMO

Catalpa pod has been used in traditional medicine for the treatment of diabetes mellitus in South America. Studies on the constituents of Catalpa species have shown that it is rich in iridoids. In the present study, three previously undescribed compounds (2-4), including two secoiridoid derivatives along with twelve known compounds, were isolated from the fruits of Catalpa bignonioides Walt. In addition, fully assigned 13C-NMR of 5,6-dihydroxy-7,4'-dimethoxyflavone-6-O-sophoroside (1) is reported for the first time in the present study. The structures of compounds were determined on the basis of extensive spectroscopic methods, including UV, IR, 1D, and 2D NMR, mass spectroscopy, and CD spectroscopic data. All the isolated compounds were evaluated for α-glucosidase inhibitory activity. Among the tested compounds, compounds 2, 3, and 9 exhibited significant inhibitory activity against α-glucosidase enzyme assay. Meanwhile, the effect of compounds 2, 3, and 9 on glucose-stimulated insulin secretion (GSIS) was measured using pancreatic ß-cells. Compounds 2, 3, and 9 exhibited non-cytotoxicity-stimulated insulin secretion in INS-1 cells. The expression levels of proteins associated with ß-cell function and insulin secretion such as phosphorylation of total insulin receptor substrate-2 (IRS-2), phosphatidylinositol 3-kinase (PI3K), Akt, activated pancreatic duodenal homeobox-1 (PDX-1), and peroxisome proliferator-activated receptor-γ (PPAR-γ) were increased in INS-1 cells after treatment with compounds 2, 3, and 9. The findings of the present study could provide a scientific warrant for their application as a potential antidiabetic agent.


Assuntos
Bignoniaceae/química , Frutas/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Secreção de Insulina/efeitos dos fármacos , alfa-Glucosidases/metabolismo , Animais , Linhagem Celular , Glucose/farmacologia , Inibidores de Glicosídeo Hidrolases/análise , Inibidores de Glicosídeo Hidrolases/química , Espectroscopia de Ressonância Magnética , PPAR gama/metabolismo , Fosfatidilinositol 3-Quinases/metabolismo , Fosforilação/efeitos dos fármacos , Ratos , alfa-Glucosidases/química
13.
Chem Biodivers ; 17(11): e2000470, 2020 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-32996697

RESUMO

Two new oligostilbenes, caragasinins D and E, along with four known compounds, kobophenol A, α-viniferin, wistin, and 5-hydroxy-2-[(4-hydroxyphenyl)acetyl]-3-methoxybenzoic acid, were isolated from the roots of Caragana sinica. These compounds were spectroscopically analyzed for their structures and configurations and compared with existing data. The configurations of caragasinins D and E were elucidated by 1 H-NMR spectroscopy, CD spectroscopy, and time-dependent density-functional theory simulated ECD spectral data. All six compounds were evaluated for their inhibitory activity against neuraminidase (NA) from Clostridium perfringens. Among the tested compounds, 5-hydroxy-2-[(4-hydroxyphenyl)acetyl]-3-methoxybenzoic acid demonstrated statistically significant NA inhibitory activity, which was comparable to the positive control, mangiferin.


Assuntos
Caragana/química , Inibidores Enzimáticos/química , Neuraminidase/antagonistas & inibidores , Estilbenos/química , Caragana/metabolismo , Dicroísmo Circular , Clostridium/enzimologia , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/metabolismo , Espectroscopia de Ressonância Magnética , Conformação Molecular , Neuraminidase/metabolismo , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Estilbenos/isolamento & purificação , Estilbenos/metabolismo
14.
J Asian Nat Prod Res ; 22(9): 830-838, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31545102

RESUMO

Two previously undescribed limonoids, 1-O-benzoyl-3-O-deactylnimbolinin C (1) and a pair of epimers named toosendalactonins A and B (12a and 12b), together with ten known compounds (2-11) were isolated from the fruits of Melia azedarach L. Their structures were determined by extensive spectroscopic methods, including 1D-, 2D-nuclear magnetic resonance, and mass spectrometry. All the isolated compounds were evaluated for their nitric oxide (NO) inhibition in lipopolysaccharide-activated microglia and nerve growth factor (NGF) production in astrocytes. Compounds 1-2 and 5-8 significantly inhibited NO production, which is comparable to the positive control, L-NMMA. Previously undescribed limonoid, compound 12, and two known limonoids, munronin K (3) and 12-O-methyl-1-O-deacetyl-nimbolinin B (4), showed the highest potency to increase the NGF production in C6 astrocytes. [Formula: see text].


Assuntos
Limoninas , Melia azedarach , Frutas , Estrutura Molecular , Óxido Nítrico
15.
Int J Mol Sci ; 21(20)2020 Oct 12.
Artigo em Inglês | MEDLINE | ID: mdl-33053881

RESUMO

Acute myeloid leukemia (AML) is an aggressive type of human leukemia with a low survival rate, and its complete remission remains challenging. Although chemotherapy is the first-line treatment of AML, it exerts toxicity in noncancerous cells when used in high doses, thus necessitating the development of novel compounds with a high therapeutic window. This study aimed to investigate the anticancer effects of several compounds derived from the fruits of Melia azedarach (a tree with medicinal properties). Among them, 1-cinnamoyltrichilinin (CT) was found to strongly suppress the viability of HL-60 human leukemia cells. CT treatment induced apoptosis and increased nuclear fragmentation and fractional DNA content in HL-60 cells in a dose-dependent manner. CT induced phosphorylation of p38 mitogen-activated protein kinases (p38), though not of c-Jun N-terminal kinase (JNK) and extracellular signal-regulated kinase (ERK), and activated Bcl-2 family proteins towards the proapoptosis and cleavage of caspase-3 and poly (ADP-ribose) polymerase. Both CT-mediated apoptosis and apoptotic protein expression were reversed by treatment with the p38 inhibitor, thereby indicating the p38 pathway to be critical in CT-stimulated apoptosis. The results collectively indicated CT to suppress HL-60 survival by activating the p38 pathway and inducing apoptosis, hence being a novel potential therapeutic agent for AML.


Assuntos
Apoptose/efeitos dos fármacos , Limoninas/farmacologia , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Melia azedarach/química , Extratos Vegetais/farmacologia , Proteínas Quinases p38 Ativadas por Mitógeno/metabolismo , Sobrevivência Celular/efeitos dos fármacos , Células HL-60 , Humanos , Limoninas/química , Estrutura Molecular , Extratos Vegetais/química
16.
Molecules ; 25(11)2020 May 28.
Artigo em Inglês | MEDLINE | ID: mdl-32481737

RESUMO

Gymnema sylvestre, a medicinal plant, has been used in Indian ayurvedic traditional medicine for the treatment of diabetes. Phytochemical investigation of Gymnema sylvestre led to the isolation of five new pregnane glycosides, gymsylosides A-E (1-5) and four known oleanane saponins, 3ß-O-ß-D-glucopyranosyl (1→6)-ß-D-glucopyranosyl oleanolic acid 28-O-ß-D-glucopyranosyl ester (6), gymnemoside-W1 (7), 3ß-O-ß-D-xylopyranosyl-(1→6)-ß-D- glucopyranosyl-(1→6)-ß-D-glucopyranosyl oleanolic acid 28-O-ß-D-glucopyranosyl ester (8), and alternoside XIX (9). Their structures were identified based on spectroscopic evidence and comparison with those reported in the literature. All compounds were evaluated for their α-glucosidase and α-amylase inhibitory activities. Compounds 2-4 showed significant α-amylase inhibitory activity, with IC50 values ranging from 113.0 to 176.2 µM.


Assuntos
Glicosídeos/farmacologia , Gymnema sylvestre/química , Pregnanos/farmacologia , alfa-Amilases/metabolismo , alfa-Glucosidases/metabolismo , Ativação Enzimática/efeitos dos fármacos
17.
Biosci Biotechnol Biochem ; 83(12): 2177-2182, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31448683

RESUMO

Three new flavonol glycosides, fissflavosides A-C (1-3), together with six known flavonol glycosides, kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-galactopyranoside (4), kaempferol 3-O-α-L-rhamnopyranosyl-(1→6)-ß-D-galactopyranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1→6)-ß-D-glucopyranoside (6), rhamnetin 3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucopyranoside (7), rutin (8), and isorhamnetin 3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-galactopyranoside (9) were isolated from the methanol extract of the Fissistigma pallens leaves. Their chemical structures were determined by 1D-, 2D-NMR, and MS data as well as in comparison with reported data in the literature. Compounds 1-9 showed weak cytotoxic activity on three human cancer cell lines, HT-29, A-2058, A-549 with IC50 ranging from 134.6 to 162.6 µM. In addition, the antioxidant capacities of compounds were also tested by ORAC assay. All compounds showed significant antioxidant with trolox equivalents ranging from 4.4 to 8.6 µM at the concentration of 1.0 µM. The results indicated 7 and 8 having meaningful reducing capacity of copper (I) ions of 2.7 to 6.9 µM at the concentrations of 1 and 2 µM.


Assuntos
Annonaceae/química , Flavonóis/química , Glicosídeos/isolamento & purificação , Antioxidantes/farmacologia , Configuração de Carboidratos , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Espectroscopia de Prótons por Ressonância Magnética , Espectrometria de Massas por Ionização por Electrospray
18.
Bioorg Med Chem Lett ; 28(4): 552-557, 2018 02 15.
Artigo em Inglês | MEDLINE | ID: mdl-29402747

RESUMO

Stilbenes have been reported to be phytoestrogen compounds owing to its structural similarity to the estrogenic agent diethylstilbestrol. To find new stilbene-derivative phytoestrogens, isolation of stilbene-rich R. undulatum was performed and led to identify six new compounds (1-5 and 28), one newly determined absolute configurations compound (27) together with 21 previously reported compounds (6-26). The structures of compounds were determined on the basis of extensive spectroscopic methods including 1D and 2D NMR and CD spectra data. All the isolated compounds were tested for their estrogenic activities in HepG2 cells transiently transfected with ERα, ERß and ERE-reporter plasmid. Among them, stilbene-derivatives, piceatannol 3'-O-ß-d-xylopyranoside (12), cis-rhaponticin (16) and rhapontigenin 3'-O-ß-d-glucopyranoside (17), showed the more potent binding affinity for estrogen receptors than 17ß-estrodiol.


Assuntos
Fitoestrógenos/farmacologia , Rheum/química , Rizoma/química , Estilbenos/farmacologia , Estradiol/química , Estradiol/metabolismo , Estradiol/farmacologia , Receptor alfa de Estrogênio/genética , Receptor alfa de Estrogênio/metabolismo , Receptor beta de Estrogênio/genética , Receptor beta de Estrogênio/metabolismo , Células Hep G2 , Humanos , Fitoestrógenos/química , Fitoestrógenos/isolamento & purificação , Fitoestrógenos/metabolismo , Estereoisomerismo , Estilbenos/química , Estilbenos/isolamento & purificação , Estilbenos/metabolismo , Transfecção
19.
Molecules ; 23(5)2018 May 18.
Artigo em Inglês | MEDLINE | ID: mdl-29783719

RESUMO

We investigated the estrogenic and breast cancer inhibitory activities of chemical constituents isolated from Rhei undulati Rhizoma (roots of Rheum undulatum L.), which is used as a laxative, an anti-inflammatory, and an anti-blood stagnation agent. Estrogen-like activity was studied using the well characterized E-screen assay in estrogen receptor (ER)-positive MCF-7 cells. The mechanism underlying the breast cancer inhibitory activity of the compounds was studied using human ER-negative MDA-MB-231 and ER-positive MCF-7 cells. The activation of apoptosis pathway-related proteins was investigated by western blotting, using extracts of R. undulatum prepared in three solvent conditions (EX1, EX2, and EX3). The R. undulatum chemical constituents (compounds 1⁻3) showed estrogen-like activity in the concentration range of 10 to 50 µM, by increasing the proliferation of human ER-positive MCF-7 cells. These effects were attenuated by co-treatment with 100 nM fulvestrant, an ER antagonist. Compounds 1⁻3 decreased the viability of MCF-7 cells in a concentration-dependent manner. Compounds 1 (aloe emodin) and 2 (rhapontigenin) induced mitochondria-independent apoptosis by activating the caspase-8 pathway, whereas the cytotoxic effect of compound 3 (chrysophanol 1-O-ß-d-glucopyranoside) was mediated through the mitochondria-dependent apoptotic pathway.


Assuntos
Neoplasias da Mama/tratamento farmacológico , Extratos Vegetais/química , Raízes de Plantas/química , Rheum/química , Antraquinonas/química , Antraquinonas/farmacologia , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Sinergismo Farmacológico , Emodina/metabolismo , Receptor alfa de Estrogênio/antagonistas & inibidores , Receptor alfa de Estrogênio/metabolismo , Estrogênios/química , Estrogênios/farmacologia , Feminino , Fulvestranto/farmacologia , Glucosídeos/química , Glucosídeos/farmacologia , Humanos , Estrutura Molecular , Extratos Vegetais/farmacologia , Estilbenos/química , Estilbenos/farmacologia , Relação Estrutura-Atividade
20.
Bioorg Med Chem Lett ; 26(15): 3780-4, 2016 08 01.
Artigo em Inglês | MEDLINE | ID: mdl-27287369

RESUMO

Using various chromatographic methods, five new steroidal saponins named taccavietnamosides A-E (1-5) and three known, (24S,25R)-spirost-5-en-3ß,24-diol 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→3)]-ß-d-glucopyranoside (6), (24S,25R)-spirost-5-en-3ß,24-diol 3-O-α-l-rhamnopyranosyl-(1→2)-[ß-d-glucopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→3)]-ß-d-glucopyranoside (7), and chantrieroside A (8) were isolated from the rhizomes of Tacca vietnamensis Thin et Hoat. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for the inhibitory activities of nitric oxide production in LPS-stimulated RAW 264.7 macrophages and BV2 cells. As the results, compounds 3-5 showed moderate inhibition on NO production in LPS-stimulated BV2 cells and RAW 264.7 macrophages with the IC50 values ranging from 37.0 to 60.7µM.


Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Dioscoreaceae/química , Óxido Nítrico/antagonistas & inibidores , Saponinas/farmacologia , Espirostanos/farmacologia , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Linhagem Celular , Relação Dose-Resposta a Droga , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Células RAW 264.7 , Saponinas/química , Saponinas/isolamento & purificação , Espirostanos/química , Espirostanos/isolamento & purificação , Relação Estrutura-Atividade
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