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1.
Phytochemistry ; 168: 112116, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31513947

RESUMO

Endophytic fungi are microorganisms located in the inter- or intracellular compartments of plant tissues but with no harmful effects. They are considered a potential source of biological compounds. The present study was conducted to investigate the molecular identification of endophytic fungi isolated from the roots of Lithospermum officinale and their potential production of shikonin. Phylogenetic analysis was performed based on the Internal Transcribed Spacer (ITS) region and the isolates were classified into five genera as follows: Alternaria, Chaetosphaeronema, Fusarium, Mucor, and Trichoderma. The study on the methanol extracts of endophytic fungi indicated that total polyphenol content had a positive relationship with antioxidant activities and the highest antioxidant activity belonged to the methanol extracts of Fusarium tricinctum and Alternaria altenata. Then, to investigate the ability of the fungal isolates to produce shikonin, a naphthoquinone compound with high biological activity, the extracts were subjected to HPLC. The results obtained from HPLC-mass spectrometry showed that shikonin could be produced only by F. tricinctum. Thus, F. tricinctum isolated from the roots of L. officinale can be presented as a new source of shikonin.


Assuntos
Antioxidantes/isolamento & purificação , Endófitos/química , Lithospermum/microbiologia , Naftoquinonas/isolamento & purificação , Naftoquinonas/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Avaliação Pré-Clínica de Medicamentos , Naftoquinonas/química , Filogenia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Picratos/antagonistas & inibidores , Raízes de Plantas/microbiologia
2.
Chem Pharm Bull (Tokyo) ; 67(8): 775-777, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31366826

RESUMO

Nocardia is a potent bacterial producer of bioactive compounds. From a culture of Nocardia beijingensis NBRC 16342, we isolated four aromatic compounds, named beijinchromes A-D (1-4). We purified them by silica gel chromatography and reverse phase HPLC, and identified their structures by NMR and high resolution (HR)-MS analyses. 1, 2, and 4 are novel 1,2,3,8-tetrasubstituted naphthalenes, and 3 is a novel 3,8-disubstituted ortho-naphthoquinone. 1 and 2 exert antioxidant activities, and 3 exhibits antibiotic activity. Remarkably, the putative biosynthetic gene clusters for 1-4 are widely distributed in 37 Nocardia species, implying their potential to produce this family of compounds and important biological functions of beijinchromes.


Assuntos
Naftalenos/química , Naftoquinonas/química , Nocardia/química , Estrutura Molecular , Naftalenos/isolamento & purificação , Naftalenos/farmacologia , Naftoquinonas/isolamento & purificação , Naftoquinonas/farmacologia , Estereoisomerismo
3.
Arch Pharm Res ; 42(6): 505-511, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31073878

RESUMO

A 70% ethanol extract from the root portion of Reynoutria japonica afforded one new and three known juglone derivatives, namely, 2-methoxy-6-acetyl-7-methyljuglone (1), 2-ethoxy-6-acetyl-7-methyljuglone (2), 2-methoxy-7-acetonyljuglone (3), and 3-acetyl-7-methoxy-2-methyljuglone (4) together with two phenolics (5 and 6), an anthraquinone (7), a stilbene (8) and a phthalide (9). Their structures were elucidated on the basis of comprehensive spectroscopic studies including IR, MS, and 1H, 13C, 2D NMR spectra. Compound 3 is a new compound in nature, and compounds 4-6 have been isolated for the first time from R. japonica. The isolates were evaluated for their antibacterial activity against three strains (43504, 51, and 26695) of Helicobacter pylori. The four isolated juglone derivatives (1-4) showed potent growth inhibitory activity. Among them, compounds 1-3 exhibited stronger inhibitory activity than those of the positive controls, juglone and metronidazole, for the three strains and that of another reference, clarithromycin, for the 43504 and 51 strains. Specifically, the new juglone compound 3 displayed the most potent antibacterial activity against all three strains, 43504, 51, and 26695, with MIC values of 0.06, 0.06 and 0.13 µM, respectively, and MIC50 values of 0.14, 0.11 and 0.15 µM, respectively.


Assuntos
Antibacterianos/farmacologia , Helicobacter pylori/efeitos dos fármacos , Naftoquinonas/farmacologia , Extratos Vegetais/farmacologia , Polygonaceae/química , Antibacterianos/isolamento & purificação , Etanol/química , Testes de Sensibilidade Microbiana , Naftoquinonas/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Raízes de Plantas/química
4.
Am J Chin Med ; 47(4): 803-822, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31094212

RESUMO

Activation of brown adipose tissue (BAT) has been proposed as a promising target against obesity due to its increased capacity for thermogenesis. In this study, we explored the effect of ß -Lapachone ( ß L), a compound obtained from the bark of the lapacho tree, against obesity. In vivo administration of ß L into either high fat diet (HFD)-induced obese C57BL6 mice and genetically obese Lepr -∕- mice prevented body weight gain, which was associated with tissue weight loss of white adipose tissue (WAT). In addition, ß L elevated thermogenic proteins including uncoupling protein 1 (UCP1) and mitochondrial count in BAT and human adipose tissue-derived mesenchymal stem cells (hAMSCs). ß L also induced AMP-activated protein kinase (AMPK) phosphorylation, subsequent upregulation of acetyl-CoA carboxylase (ACC) and UCP1, and these effects were diminished by AMPK inhibitor compound C, suggesting that AMPK underlies the effects of ß L. Mitogen-activated protein kinase pathways participated in the thermogenesis of ß L, specifically p38, c-Jun N-terminal kinase (JNK) and extracellular signal-regulated kinase 1/2 (ERK1/2) were activated by ß L treatment in hAMSCs. Additionally, inhibitors of p38/JNK/ERK1/2 abrogated the activity of ß L. Taken together, ß L exerts anti-obese effects by inducing thermogenesis mediated by AMPK signaling pathway, suggesting that ß L may have a potential therapeutic implication of obesity. Taken together, ß L exerts anti-obese effects by not only inducing thermogenesis on brown adipocytes but also inducing the browning of white adipocytes. The anti-obese effect of ß L is mediated by AMPK signaling pathway, suggesting that ß L may have potential therapeutic implication of obesity.


Assuntos
Proteínas Quinases Ativadas por AMP/fisiologia , Adipócitos/metabolismo , Tecido Adiposo Marrom/metabolismo , Naftoquinonas/administração & dosagem , Naftoquinonas/farmacologia , Obesidade/tratamento farmacológico , Obesidade/metabolismo , Fitoterapia , Transdução de Sinais/fisiologia , Tabebuia/química , Termogênese/efeitos dos fármacos , Animais , Fármacos Antiobesidade , Células Cultivadas , Dieta Hiperlipídica/efeitos adversos , Humanos , Masculino , Camundongos Endogâmicos C57BL , Mitocôndrias/patologia , Naftoquinonas/isolamento & purificação , Obesidade/etiologia , Fosforilação , Termogênese/genética , Termogênese/fisiologia , Proteína Desacopladora 1/metabolismo , Ganho de Peso/efeitos dos fármacos
5.
Arch Virol ; 164(6): 1543-1552, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30905031

RESUMO

Influenza virus infection is a public health problem, causing significant morbidity and mortality. Currently, zanamivir and oseltamivir are in common use, and there are already reports of antiviral resistance. Several studies have shown the antiviral potential of a wide variety of plant-based natural compounds, among them those of the quinone type. In this study, we evaluated the antiviral activity of naphthoquinones isolated from the stem bark of Diospyros anisandra, and we selected zeylanone epoxide (ZEP) to study its effects on influenza A and B viruses. Our results indicated that ZEP inhibits the replication of influenza A and B viruses, at early and middle stages of the replication cycle. Confined nuclear localization of the viral NP indicated that ZEP affects its intracellular distribution and reduces viral yield. This is the first report on the antiviral properties and possible mechanism of action of ZEP in vitro, showing its broad-spectrum activity against influenza A and B viruses.


Assuntos
Diospyros/química , Vírus da Influenza A/fisiologia , Influenzavirus B/fisiologia , Naftoquinonas/farmacologia , Animais , Núcleo Celular/virologia , Cães , Vírus da Influenza A/efeitos dos fármacos , Células Madin Darby de Rim Canino , Naftoquinonas/isolamento & purificação , Casca de Planta/química , Caules de Planta/química , Carga Viral/efeitos dos fármacos , Replicação Viral/efeitos dos fármacos
6.
J Agric Food Chem ; 67(7): 1839-1846, 2019 Feb 20.
Artigo em Inglês | MEDLINE | ID: mdl-30688448

RESUMO

Fusarium, a large genus of filamentous fungi, is widely distributed in soil and plants. Fusarium is a prolific source of novel chemical constituents with various bioactivities. In search for antibiotics from soil and endophytic fungi, the secondary metabolites of Fusarium avenaceum SF-1502 and Fusarium proliferatum AF-04 were investigated. An alkaloid (1), a depsipeptide (6), and five sesquiterpenoids (7-11) were isolated from the extracts of the soil fungus F. avenaceum SF-1502. Three alkaloids (2-4), a depsipeptide (5), three sesquiterpenoids (9, 11, and 12), a sesterterpene (13), and four 1,4-naphthoquinones (14-17) were also separated from the extract of the green Chinese onion derived fungus F. proliferatum AF-04. Fusaravenin (1) represents the first example of a natural naphthoisoxazole-type zwitter-ionic alkaloid, a naphthoisoxazole formic acid connected with a morpholino carbon skeleton. Cyclonerotriol B (7) is a new cyclonerane sesquiterpene. Another new sesquiterpene, 3ß-hydroxy-ß-acorenol (12), possesses an acorane framework. The known compounds 9 and 11 were found from both fungi. The structures of the new compounds were determined via extensive HR-ESI-MS and comparison between experimental and calculated NMR results. The biological properties of 1-5 and 7-17 were evaluated against eight anthropogenic bacteria, while 1 and 7-11 were also screened for inhibitory effects against four plant pathogen bacteria. The known compounds 8, 9, and 14-17 showed potent antibacterial activities toward some of the tested anthropogenic bacteria.


Assuntos
Alcaloides/isolamento & purificação , Depsipeptídeos/isolamento & purificação , Fusarium/química , Naftoquinonas/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Microbiologia do Solo , Alcaloides/química , Alcaloides/farmacologia , Antibacterianos , Depsipeptídeos/química , Depsipeptídeos/farmacologia , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Estrutura Molecular , Naftoquinonas/química , Naftoquinonas/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Espectrometria de Massas por Ionização por Electrospray
7.
Nat Prod Res ; 33(22): 3203-3209, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-29726709

RESUMO

Juglonols A-C (1-3), three new juglone derivatives possessing a hydroxyethyl side chain, were isolated from an organic extract of the immature exocarps of Juglans mandshurica together with five known tetralones (4-8). Their structures were elucidated by extensive spectroscopic analyses and comparison with literature data. The new juglone derivatives exhibited inhibitory activities towards a panel of bacteria and fungi, as well as cancer cell lines. In contrast, the known tetralone homologues (4-8) appeared to be much less efficacy.


Assuntos
Anti-Infecciosos/isolamento & purificação , Juglans/química , Naftoquinonas/farmacologia , Extratos Vegetais/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Anti-Infecciosos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Linhagem Celular , Humanos , Estrutura Molecular , Naftoquinonas/isolamento & purificação , Naftoquinonas/toxicidade , Extratos Vegetais/farmacologia , Análise Espectral/métodos , Tetralonas/isolamento & purificação , Tetralonas/farmacologia
8.
Food Chem Toxicol ; 123: 492-500, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30458268

RESUMO

Plumbagin (5-hydroxy-2-methyl-1,4-naphthaquinone) has displayed antitumor activity in vitro and in animal models; however, the underlying molecular mechanisms have not been fully explored. The aim of this study was to investigate the anticancer effects of plumbagin isolated from Nepenthes alata against MCF-7 breast cancer cells. We examined the cytotoxicity, cell cycle regulation, apoptotic cell death, and generation of intracellular reactive oxygen species (ROS) in MCF-7 cells. Plumbagin exhibited potent cytotoxicity in MCF-7 cells (wild-type p53) compared to that in SK-OV-3 (null-type) human epithelial ovarian cancer cells. Specifically, plumbagin upregulated the expression of p21CIP1/WAF1 in MCF-7 cells, causing cell cycle arrest in the G2/M phase through inhibition of cyclin B1 levels. Plumbagin also significantly increased the ratio of Bax/Bcl-2 and release of cytochrome c, resulting in apoptotic cell death in MCF-7 cells. Furthermore, plumbagin dramatically increased the intracellular ROS level, whereas pretreatment with the ROS scavenger N-acetyl cysteine protected against plumbagin-induced cytotoxicity, suggesting that ROS formation plays a pivotal role in antitumor activity in MCF-7 cells. In mice bearing MCF-7 cell xenografts, plumbagin significantly reduced tumor growth and weight without apparent side effects. We therefore concluded that plumbagin exerts anticancer activity against MCF-7 cells through the generation of intracellular ROS, resulting in the induction of apoptosis via a p53-dependent pathway. This study thus identifies a new anticancer mechanism of plumbagin against p53-dependent breast cancer cells and suggests a novel strategy for overcoming of breast cancer therapy.


Assuntos
Antineoplásicos Fitogênicos/administração & dosagem , Apoptose/efeitos dos fármacos , Neoplasias da Mama/tratamento farmacológico , Caryophyllales/química , Naftoquinonas/administração & dosagem , Proteína Supressora de Tumor p53/metabolismo , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Neoplasias da Mama/genética , Neoplasias da Mama/metabolismo , Neoplasias da Mama/fisiopatologia , Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Feminino , Humanos , Células MCF-7 , Camundongos Endogâmicos BALB C , Camundongos Nus , Naftoquinonas/química , Naftoquinonas/isolamento & purificação , Espécies Reativas de Oxigênio/metabolismo , Proteína Supressora de Tumor p53/genética
9.
Fitoterapia ; 132: 46-52, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30496808

RESUMO

Seven new naphthoquinone derivatives, named eleutherins A-G (1-7), were isolated from the edible bulbs of Eleutherine americana (Hong-Cong), which belongs to the Iridaceae family. Their structures were elucidated on the basis of spectroscopic analysis including high-resolution-electron spray ionization-mass spectrometry (HR-ESI-MS) and 1D and 2D nuclear magnetic resonance (NMR) techniques. The absolute configurations of compounds 1-4 were determined by experimental and calculated data. Additionally, a hypothetical biosynthetic pathway of 1-7 was postulated. All the isolates were evaluated for their protective effect against the injury of human umbilical vein endothelial cells (HUVECs) in vitro. Eleutherins A and B (1-2) showed a potential protective effect on microvessels.


Assuntos
Células Endoteliais da Veia Umbilical Humana/efeitos dos fármacos , Iridaceae/química , Naftoquinonas/química , Células Cultivadas , China , Humanos , Estrutura Molecular , Naftoquinonas/isolamento & purificação , Raízes de Plantas/química , Substâncias Protetoras/química , Substâncias Protetoras/isolamento & purificação
10.
Biotechnol Prog ; 35(1): e2738, 2019 01.
Artigo em Inglês | MEDLINE | ID: mdl-30365243

RESUMO

Filamentous fungi have gained growing interest as sources of diverse pigmented secondary metabolites. Some specific polyketides from Ascomycetous species have demonstrated a wide range of industrial applications in food, cosmetic, textile, and in the design of pharmaceutical products. The formulation of recipes containing fungal polyketides has increased over recent years. Fusarium strains were proven useful to mankind in a variety of technologies. Nevertheless, there is still need of new isolates of Fusarium for use in emerging and already existing fields. In this article, we report the concomitant production of the bioactive red bikaverin along with two novel purple pigments by the phytopathogenic Fusarium oxysporum LCP531 strain isolated from soil. In literature, the production of purple pigment had only been described in cultures of Fusarium Fujikuroi, Fusarium verticillioides, and Fusarium graminearum. The production of these naphthoquinonic pigments, their distribution (either produced in mycelia or excreted in liquid medium) and their chemical profiles were investigated with respect to nutrient composition. The pigments were extracted by using a pressurized liquid extraction method, monitored by colorimetric analysis and characterized by HPLC-DAD chromatography. To our knowledge, this is the first report of these two novel wild-type purple naphtoquinones pigments along with bikaverin, where additionally, the culture conditions were put into perspective to optimize fermentation cultures and extraction process accordingly to the pigment/biomolecule desired. These colored naphthoquinones should be promising fungal functional compounds which could be expected to have a place of choice, along with other antibacterial, antifungal, antiviral, anticancer, and antineoplastic derivatives. © 2018 American Institute of Chemical Engineers Biotechnol. Prog., 35: e2738, 2019.


Assuntos
Fusarium/metabolismo , Naftoquinonas/química , Policetídeos/química , Xantonas/química , Proteínas Fúngicas/metabolismo , Naftoquinonas/isolamento & purificação , Pigmentos Biológicos/química , Pigmentos Biológicos/isolamento & purificação
11.
Nat Prod Res ; 33(14): 2044-2050, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-29923426

RESUMO

A new yellow pigment trypethelonamide A (1), and a new dark violet-red pigment 5'-hydroxytrypethelone (2), as well as three known dark violet-red pigments (+)-8-hydroxy-7-methoxytrypethelone (3), (+)-trypethelone (4) and (-)-trypethelone (5) were isolated from the cultured lichenized fungus Trypethelium eluteriae. The structures of 1 and 2 were determined to be 1, 2-naphthoquinone derivatives by extensive spectroscopic analysis. The absolute configurations of 1 and 2 were assigned by quantum electronic circular dichroism (ECD) calculation. All isolated compounds were evaluated for cytotoxicities against A549, HepG2 and RKO cell lines, and antioxidant effects on DPPH. Compounds 1-5 showed moderate and weak cytotoxicities against RKO cell line with IC50 from 22.6 to 113.5 µM.


Assuntos
Líquens/química , Naftoquinonas/isolamento & purificação , Antioxidantes/farmacologia , Ascomicetos , Morte Celular/efeitos dos fármacos , Linhagem Celular , Dicroísmo Circular , Corantes/química , Corantes/isolamento & purificação , Humanos , Estrutura Molecular , Naftoquinonas/química , Policetídeos/química , Policetídeos/isolamento & purificação , Análise Espectral
12.
J Asian Nat Prod Res ; 21(8): 826-831, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-29947258

RESUMO

A new medermycin analog (1) was isolated from the marine-derived actinomycetes Streptomyces sp. ZS-A45. The structure elucidation of compound 1 was determined by the HRESIMS and extensive NMR analysis. And compound 1 exhibited significant cytotoxicity against PC3 cell lines with IC50 values of 0.81 ± 0.42 µm.


Assuntos
Actinobacteria/metabolismo , Antibacterianos/isolamento & purificação , Antibacterianos/química , Antibacterianos/farmacologia , Linhagem Celular Tumoral , Dicroísmo Circular , Humanos , Espectroscopia de Ressonância Magnética , Biologia Marinha , Naftoquinonas/isolamento & purificação
13.
Nat Prod Res ; 33(3): 360-366, 2019 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-29561167

RESUMO

Rhinacanthus nasutus (L.) Kurz (Acanthaceae) is known as traditional medicine for the treatment of fungal and herpes virus infections. A new naphthoquinone racemate, rhinacasutone (1) together with seven known compounds, rhinacanthone (2), rhinacanthins C, D, N, Q, and E (3-7), and heliobuphthalmin (8) were isolated from root of R. nasutus. Their structures were determined on the basis of extensive spectroscopic methods, including 1D-, 2D-NMR and MS data. All the isolated compounds were tested for their antiviral activities against PR8, HRV1B, and CVB3-infected vero cells. Compounds 3-6 exhibited significant antiviral activities with the IC50 value ranging from 0.03 to 23.7 µM in all three infections.


Assuntos
Acanthaceae/química , Antivirais/isolamento & purificação , Naftoquinonas/isolamento & purificação , Animais , Antivirais/química , Antivirais/farmacologia , Benzopiranos/isolamento & purificação , Lignanas/isolamento & purificação , Naftoquinonas/química , Naftoquinonas/farmacologia , Extratos Vegetais/química , Raízes de Plantas/química , Células Vero
14.
Food Chem ; 272: 379-387, 2019 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-30309558

RESUMO

The extraction of polyhydroxylated naphthoquinone (PHNQ) pigments from the shell and spines of the New Zealand sea urchin Evechinus chloroticus was evaluated using six different macroporous resins as an alternative to using organic solvent extraction alone. Four of the resins evaluated in this study (D4006, D4020, D101 and NKA-9) provided the best extraction of PHNQ pigments in terms of the overall adsorption and desorption of E. chloroticus PHNQ pigments from the resins. Organic solvents alone had a higher yield of PHNQs than the resins. The PHNQ composition was characterised by high-performance liquid chromatography (HPLC) with diode-array detection and mass spectrometry. Five PHNQ compounds (spinochromes E, B, C, A and echinochrome A), and three aminated PHNQ compounds (spinamine E, echinamines A and B) were identified. The pigments were found to be prone to degradation on exposure to light, with the aminated PHNQ pigments being the least stable.


Assuntos
Exoesqueleto/química , Naftoquinonas/química , Naftoquinonas/isolamento & purificação , Ouriços-do-Mar/química , Coluna Vertebral/química , Animais , Estabilidade de Medicamentos , Hidroxilação , Espectrometria de Massas
15.
Mar Drugs ; 17(1)2018 Dec 20.
Artigo em Inglês | MEDLINE | ID: mdl-30577438

RESUMO

Doxorubicin, an anthracycline from Streptomyces peucetius, exhibits antitumor activity against various cancers. However, doxorubicin is cardiotoxic at cumulative doses, causing increases in intracellular reactive oxygen species in the heart. Spinochrome D (SpD) has a structure of 2,3,5,6,8-pentahydroxy-1,4-naphthoquinone and is a structural analogue of well-known sea urchin pigment echinochrome A. We previously reported that echinochrome A is cardioprotective against doxorubicin toxicity. In the present study, we assessed the cardioprotective effects of SpD against doxorubicin and determined the underlying mechanism. ¹H-NMR-based metabolomics and mass spectrometry-based proteomics were utilized to characterize the metabolites and proteins induced by SpD in a human cardiomyocyte cell line (AC16) and human breast cancer cell line (MCF-7). Multivariate analyses identified 12 discriminating metabolites (variable importance in projection > 1.0) and 1814 proteins from SpD-treated AC16 cells. Proteomics and metabolomics analyses showed that glutathione metabolism was significantly influenced by SpD treatment in AC16 cells. SpD treatment increased ATP production and the oxygen consumption rate in D-galactose-treated AC16 cells. SpD protected AC16 cells from doxorubicin cytotoxicity, but it did not affect the anticancer properties. With SpD treatment, the mitochondrial membrane potential and mitochondrial calcium localization were significantly different between cardiomyocytes and cancer cell lines. Our findings suggest that SpD could be cardioprotective against the cytotoxicity of doxorubicin.


Assuntos
Antibióticos Antineoplásicos/efeitos adversos , Cardiotônicos/farmacologia , Cardiotoxicidade/prevenção & controle , Doxorrubicina/efeitos adversos , Miócitos Cardíacos/efeitos dos fármacos , Naftoquinonas/farmacologia , Animais , Apoptose/efeitos dos fármacos , Cardiotônicos/isolamento & purificação , Cardiotoxicidade/etiologia , Sobrevivência Celular/efeitos dos fármacos , Feminino , Glutationa/metabolismo , Células HeLa , Humanos , Células MCF-7 , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Metabolômica/métodos , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/metabolismo , Miócitos Cardíacos/metabolismo , Naftoquinonas/isolamento & purificação , Neoplasias/tratamento farmacológico , Ressonância Magnética Nuclear Biomolecular/métodos , Estresse Oxidativo/efeitos dos fármacos , Proteômica/métodos , Espectroscopia de Prótons por Ressonância Magnética/métodos , Ratos , Espécies Reativas de Oxigênio/metabolismo , Ouriços-do-Mar
16.
Mar Drugs ; 16(11)2018 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-30388746

RESUMO

Sea urchin pigment echinochrome A (Ech), a water-insoluble compound, is the active substance in the cardioprotective and antioxidant drug Histochrome® (PIBOC FEB RAS, Moscow, Russia). It has been established that Ech dissolves in aqueous solutions of carrageenans (CRGs). Herein, we describe the effects of different types of CRGs on some properties of Ech. Our results showed that CRGs significantly decreased the spermotoxicity of Ech, against the sea urchin S. intermedius sperm. Ech, as well as its complex with CRG, did not affect the division and development of early embryos of the sea urchin. Ech reduced reactive oxygen species production (ROS) in neutrophils, caused by CRG. The obtained complexes of these substances with pro- and anti-activating ROS formation properties illustrate the possibility of modulating the ROS induction, using these compounds. The CRGs stimulate the induction of anti-inflammatory IL-10 synthesis, whereas Ech inhibits this synthesis and increases the production of the pro-inflammatory cytokines IL-6 and TNFα. The inclusion of Ech, in the complex with the CRGs, decreases Ech's ability to induce the expression of pro-inflammatory cytokines, especially TNFα, and increases the induction of anti-inflammatory cytokine IL-10. Thus, CRGs modify the action of Ech, by decreasing its pro-inflammatory effect. Whereas, the Ech's protective action towards human epithelial HT-29 cells remains to be unaltered in the complex, with κ/ß-CRG, under stress conditions.


Assuntos
Antioxidantes/farmacologia , Produtos Biológicos/química , Carragenina/química , Naftoquinonas/farmacologia , Ouriços-do-Mar , Animais , Antioxidantes/isolamento & purificação , Produtos Biológicos/isolamento & purificação , Carragenina/isolamento & purificação , Citocinas/metabolismo , Sistemas de Liberação de Medicamentos/métodos , Embrião não Mamífero , Células HT29 , Humanos , Concentração Inibidora 50 , Naftoquinonas/isolamento & purificação , Espécies Reativas de Oxigênio/metabolismo , Rodófitas/química
17.
Biomed Pharmacother ; 107: 1160-1165, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30257329

RESUMO

The naphthopyranones paepalantine and 5-methoxy-3,4-dehydroxanthomegnin isolated from Paepalanthus sp, showed in previous studies antioxidant, anti-inflammatory, antitumour and antimicrobial potential, such as anti-Helicobacter pylori activity. H. pylori infection is one of the main causes of gastric cancer, causing an excessive inflammatory response through the neutrophils and macrophages infiltration, increasing the release of reactive species and thus inducing the production of pro-inflammatory mediators. In the present study, immunomodulatory activity of naphthopyranones in LPS-stimulated macrophages and cytotoxic action in gastric adenocarcinoma cell lines was evaluated. The potential of interaction of these substances in the iNOS binding site was investigated by molecular docking. Cytotoxic activity in gastric adenocarcinoma cells (AGS) was evaluated by the MTT assay. The results evidenced immunomodulatory potential by inhibiting the pro-inflammatory cytokines and nitric oxide produced by LPS-stimulated macrophages. Cytotoxic activity in AGS cell line was also reported. The results indicated that the studied naphthopyranones are viable alternatives in the treatment and prevention of H. pylori infection as well as the diseases related to this infection, especially gastric cancer.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Fatores Imunológicos/farmacologia , Isocumarinas/farmacologia , Naftoquinonas/farmacologia , Adenocarcinoma/tratamento farmacológico , Adenocarcinoma/patologia , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Simulação por Computador , Citocinas/metabolismo , Eriocaulaceae/química , Infecções por Helicobacter/tratamento farmacológico , Helicobacter pylori/efeitos dos fármacos , Humanos , Fatores Imunológicos/isolamento & purificação , Isocumarinas/isolamento & purificação , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Simulação de Acoplamento Molecular , Naftoquinonas/isolamento & purificação , Óxido Nítrico/metabolismo , Óxido Nítrico Sintase Tipo II/metabolismo , Células RAW 264.7 , Neoplasias Gástricas/tratamento farmacológico , Neoplasias Gástricas/patologia
18.
J Nat Prod ; 81(9): 2120-2124, 2018 09 28.
Artigo em Inglês | MEDLINE | ID: mdl-30209946

RESUMO

Four new medermycin-type naphthoquinones, strepoxepinmycins A-D (1-4), and one known compound, medermycin (5), were identified from Streptomyces sp. XMA39. Their structures were elucidated by analysis of HRESIMS, 1D and 2D NMR spectroscopic data, and ECD calculations. Among these compounds, strepoxepinmycin A (1) represents a rare 5,10-oxepindione ring system typically formed by a Baeyer-Villiger oxidation, and strepoxepinmycin B (2) is an isolation artifact derived from 1. Bioactivity evaluations of these compounds showed that compounds 3 and 4 exhibited cytotoxicity against HCT-116 and PC-3 cancer cell lines and 4 exhibited moderate inhibition of ROCK 2 protein kinase. In addition, all of the new compounds showed antibacterial activity against Escherichia coli and methicillin-resistant Staphylococcus aureus and antifungal activity against Candida albicans.


Assuntos
Naftoquinonas/isolamento & purificação , Streptomyces/metabolismo , Microbiologia da Água , Anti-Infecciosos/farmacologia , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Humanos , Naftoquinonas/química , Naftoquinonas/farmacologia
19.
Bull Exp Biol Med ; 165(3): 340-343, 2018 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30006880

RESUMO

The effects of therapeutic or preventive-therapeutic administration of water-soluble echinochrome analog U-441 on arrhythmia severity assessed by a set of myocardial spatio-temporal depolarization and repolarization parameters were examined on the model of acute myocardial ischemia in cats. Coronary occlusion increased activation time and decreased repolarization time in the ischemic zone; in addition, it increased both global and borderline (local) dispersions of repolarization. The linear regression model showed that only activation time values measured at the initial state and at termination of occlusion were associated with total arrhythmia score during ischemia (regression coefficient ß=0.338, 95%CI=0.074-0.602, p=0.015 and ß=0.720, 95%CI=0.323-1.117, p=0.001, respectively). The study revealed no association between administration of echinochrome analog U-441 and arrhythmia severity.


Assuntos
Antiarrítmicos/farmacologia , Arritmias Cardíacas/tratamento farmacológico , Isquemia Miocárdica/tratamento farmacológico , Naftoquinonas/farmacologia , Animais , Antiarrítmicos/isolamento & purificação , Arritmias Cardíacas/fisiopatologia , Gatos , Oclusão Coronária/cirurgia , Modelos Animais de Doenças , Eletrocardiografia , Sistema de Condução Cardíaco/efeitos dos fármacos , Sistema de Condução Cardíaco/fisiopatologia , Isquemia Miocárdica/fisiopatologia , Miocárdio/patologia , Naftoquinonas/isolamento & purificação , Ouriços-do-Mar/química , Índice de Gravidade de Doença , Solubilidade , Falha de Tratamento , Água/química
20.
Curr Pharm Biotechnol ; 19(5): 372-381, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-29956626

RESUMO

BACKGROUND: Increased demand for compounds that are derived from natural source are gaining more and more importance. Plumbagin is a plant naphthoquinone which is present in several families, including Iridaceae, Plumbaginaceae, Ebenceae, Drosophyllaceae, Nepenthaceae and Droseraceae. Plumbagin possesses high therapeutic efficacy and minimal side effects. It has various pharmaceutical activities which include anticancer, antibacterial, anti-inflammatory, antioxidant, antifungal, neuroprotective and hypolipidemic activities. In natural habitat, production of plumbagin is low due to species variations and environmental changes, considering importance of this bioactive compound, alternative techniques for its enhanced production needs to be devised. In the present review, various production techniques and scale-up strategies for plumbagin production are discussed. OBJECTIVES: Aim of this review is to provide an insight into the chemistry of plumbagin, its pharmaceutical activities, perspective of cell suspension culture, root culture, hairy root culture and scale up strategies for its production. METHODOLOGY: All the data compiled and presented here were obtained from various E-resources like Pubmed, Science Direct, and Google Scholar up to February 2018. RESULT: This review comprises isolation, extraction and quantification method for plumbagin, its pharmaceutical activities, various tissue culture production techniques and scale-up strategies for enhanced production. CONCLUSION: Plumbagin is an important phytocompound which shows potential towards treatments of various diseases. Demand for the production of plumbagin continuously increasing worldwide due to its pharmacological properties. To fulfil commercial demand of plumbagin alternative technologies need to be investigated. Biotechnological approaches like cell suspension culture, root suspension culture and hairy root culture are alternative techniques for plumbagin production. These techniques provide continuous supply of bioactive compounds. However, research on various aspects of tissue culture production techniques is in preparatory stage and requires culture and process optimization for development of a commercially practical process.


Assuntos
Biotecnologia/métodos , Naftoquinonas/isolamento & purificação , Plumbaginaceae/metabolismo , Técnicas de Cultura de Células , Naftoquinonas/química , Naftoquinonas/metabolismo , Naftoquinonas/farmacologia , Raízes de Plantas/metabolismo
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