Your browser doesn't support javascript.
loading
Mostrar: 20 | 50 | 100
Resultados 1 - 20 de 284
Filtrar
Mais filtros










Intervalo de ano de publicação
1.
Eur J Med Chem ; 191: 112159, 2020 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-32101782

RESUMO

The endophytic fungus Cladosporium sphaerospermum WBS017 was obtained from healthy bulbs of Fritillaria unibracteata var. wabuensis. Fermentation of C. sphaerospermum on solid rice medium yielded three new hybrid polyketides, cladosins L-N (1-3), and a known derivative cladodionen (4). Further cultivation of this fungus on white bean medium afforded an additional new hybrid polyketide, cladosin O (5) along with three known analogues (6-8). The structures of the new compounds were elucidated using a combination of NMR and HRESIMS data. The absolute configurations of compounds 2 and 3 were determined by Mosher's method and TDDFT-ECD calculations. All isolated compounds were evaluated for their cytotoxic and antimicrobial activities. Cladodionen (4) exhibited cytotoxicity against the mouse lymphoma cell line L5178Y with an IC50 value of 3.7 µM, and also exhibited antifungal activity against Ustilago maydis and Saccharomyces cerevisiae, while cladosin L (1) displayed week antibacterial activity against Staphylococcus aureus ATCC 29213 and S. aureus ATCC 700699 with MIC values of 50 and 25 µM, respectively.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Antineoplásicos/farmacologia , Cladosporium/química , Policetídeos/farmacologia , Acinetobacter baumannii/efeitos dos fármacos , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Teoria da Densidade Funcional , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Enterococcus faecalis/efeitos dos fármacos , Camundongos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Mycobacterium tuberculosis/efeitos dos fármacos , Policetídeos/química , Policetídeos/isolamento & purificação , Pseudomonas aeruginosa/efeitos dos fármacos , Saccharomyces cerevisiae/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacos , Relação Estrutura-Atividade , Ustilago/efeitos dos fármacos
2.
Mar Drugs ; 18(2)2020 Feb 03.
Artigo em Inglês | MEDLINE | ID: mdl-32028626

RESUMO

Three new compounds, monarubins A-C (1, 6 and 13), together with ten known compounds, including four alkaloids (2-5), two isocoumarins (7 and 8) and four polyketides (9-12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 µΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 µΜ, respectively.


Assuntos
Antineoplásicos/isolamento & purificação , Monascus/metabolismo , Alcaloides/administração & dosagem , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Animais , Antineoplásicos/administração & dosagem , Antineoplásicos/farmacologia , Carcinoma Hepatocelular/tratamento farmacológico , Carcinoma Hepatocelular/patologia , Linhagem Celular Tumoral , Células Hep G2 , Humanos , Isocumarinas/isolamento & purificação , Isocumarinas/farmacologia , Neoplasias Hepáticas/tratamento farmacológico , Neoplasias Hepáticas/patologia , Monascus/isolamento & purificação , Carcinoma Nasofaríngeo/tratamento farmacológico , Carcinoma Nasofaríngeo/patologia , Neoplasias Nasofaríngeas/tratamento farmacológico , Neoplasias Nasofaríngeas/patologia , Policetídeos/isolamento & purificação , Policetídeos/farmacologia , Frutos do Mar/microbiologia
3.
Org Lett ; 22(4): 1275-1279, 2020 02 21.
Artigo em Inglês | MEDLINE | ID: mdl-32017574

RESUMO

Forazoline A is a structurally complex PKS-NRPS hybrid produced by marine-derived Actinomadura sp. During the course of studies highlighting the application of IFS analysis as a powerful tool for natural products analysis, we were alerted to an earlier misinterpretation with respect to forazoline A structure elucidation. In particular, IFS reveals that forazoline A contains a thioketone moiety rarely seen in secondary metabolites and, thus, constitutes an even more intriguing structure than originally thought.


Assuntos
Actinomycetales/química , Produtos Biológicos/química , Policetídeos/química , Produtos Biológicos/isolamento & purificação , Isótopos , Espectrometria de Massas , Conformação Molecular , Policetídeos/isolamento & purificação
4.
J Antibiot (Tokyo) ; 73(5): 283-289, 2020 05.
Artigo em Inglês | MEDLINE | ID: mdl-31949315

RESUMO

Eight new fasamycin-type polyketides, streptovertimycins A-H (1-8), were isolated from soil-derived Streptomyces morookaense SC1169 cultivated on wheat grains. Their structures were established by extensive spectroscopic analysis and theoretical computations of ECD spectra. Compounds 1-8 have a fasamycin-type pentacyclic structure featuring a 15-O-methyl group. They exhibited potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VRE) with MIC values in the range of 0.63-5.0 µg/ml. The activity profile provided new insights into the structure-activity relationships of fasamycin-type antibiotics.


Assuntos
Antibacterianos/farmacologia , Compostos de Bifenilo/farmacologia , Hidrocarbonetos Policíclicos Aromáticos/farmacologia , Policetídeos/farmacologia , Streptomyces/metabolismo , Antibacterianos/química , Antibacterianos/isolamento & purificação , Compostos de Bifenilo/química , Compostos de Bifenilo/isolamento & purificação , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Hidrocarbonetos Policíclicos Aromáticos/química , Hidrocarbonetos Policíclicos Aromáticos/isolamento & purificação , Policetídeos/química , Policetídeos/isolamento & purificação , Microbiologia do Solo , Relação Estrutura-Atividade , Enterococos Resistentes à Vancomicina/efeitos dos fármacos
5.
J Antibiot (Tokyo) ; 73(4): 211-223, 2020 04.
Artigo em Inglês | MEDLINE | ID: mdl-31974520

RESUMO

Eight new potentiators of antifungal amphotericin B (AmB) activity, phialotides A to H, were isolated from the fermentation broths of the rare fungus Pseudophialophora sp. BF-0158. The structures of phialotides were elucidated by spectroscopic analyses, including NMR and MS, and degradation studies. Phialotides were novel polyketide glycosides consisting of a 1,3-dimethylbut-1-ene (C6-unit) repeating substructure and one to three hexopyranoses. None of the phialotides exhibited antifungal activity, whereas all potentiated AmB activity against several fungi. Phialotide F was the most effective potentiator of AmB activity against Candida albicans, with a decrease in the MIC from 0.50 to 0.016 µg ml-1 being observed in combination with phialotide F at 1.0 µg ml-1.


Assuntos
Anfotericina B/química , Anfotericina B/farmacologia , Antifúngicos/farmacologia , Glicosídeos/farmacologia , Policetídeos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Ascomicetos/química , Candida albicans/efeitos dos fármacos , Sinergismo Farmacológico , Glicosídeos/administração & dosagem , Glicosídeos/química , Glicosídeos/isolamento & purificação , Testes de Sensibilidade Microbiana , Policetídeos/administração & dosagem , Policetídeos/química , Policetídeos/isolamento & purificação
6.
Mar Drugs ; 18(2)2020 Jan 23.
Artigo em Inglês | MEDLINE | ID: mdl-31979231

RESUMO

Three new polyketides, ketidocillinones A-C (1-3), were discovered from the extract of an Antarctica sponge-derived fungus Penicillium sp. HDN151272. All the structures were deduced by spectroscopic data, including NMR and HRESIMS. The absolute configuration of compound 3 was established by using ECD calculation. Compounds 1-3 can be slowly oxidized to quinone form when exposed to air. Ketidocillinones B and C (2 and 3) exhibited potent antibacterial activity against Pseudomonas aeurigenosa, Mycobacterium phlei, and MRCNS (methicillin-resistant coagulase-negative staphylococci) with MIC values ranging from 1.56 to 25.00 µg/mL.


Assuntos
Antibacterianos/farmacologia , Organismos Aquáticos/química , Penicillium/química , Policetídeos/farmacologia , Poríferos/microbiologia , Animais , Regiões Antárticas , Antibacterianos/química , Antibacterianos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Mycobacterium phlei/efeitos dos fármacos , Policetídeos/química , Policetídeos/isolamento & purificação , Pseudomonas aeruginosa/efeitos dos fármacos
7.
Mar Drugs ; 18(2)2020 Jan 23.
Artigo em Inglês | MEDLINE | ID: mdl-31979232

RESUMO

Microbial co-cultivation is employed for awakening silent biosynthetic gene clusters (BGCs) to enhance chemical diversity. However, the selection of appropriate partners for co-cultivation remains a challenge. Furthermore, competitive interactions involving the suppression of BGCs or upregulation of known, functional metabolite(s) during co-cultivation efforts is also common. Herein, we performed an alternative approach for targeted selection of the best co-cultivation pair. Eight marine sediment-derived fungi were classified as strong or weak, based on their anti-phytopathogenic potency. The fungi were co-cultured systematically and analyzed for their chemical profiles and anti-phytopathogenic activity. Based on enhanced bioactivity and a significantly different metabolite profile including the appearance of a co-culture specific cluster, the co-culture of Plenodomus influorescens (strong) and Pyrenochaeta nobilis (weak) was prioritized for chemical investigation. Large-scale co-cultivation resulted in isolation of five polyketide type compounds: two 12-membered macrolides, dendrodolide E (1) and its new analog dendrodolide N (2), as well as two rare azaphilones spiciferinone (3) and its new analog 8a-hydroxy-spiciferinone (4). A well-known bis-naphtho-γ-pyrone type mycotoxin, cephalochromin (5), whose production was specifically enhanced in the co-culture, was also isolated. Chemical structures of compounds 1-5 were elucidated by NMR, HRMS and [] analyses. Compound 5 showed the strongest anti-phytopathogenic activity against Xanthomonas campestris and Phytophthora infestans with IC50 values of 0.9 and 1.7 µg/mL, respectively.


Assuntos
Agroquímicos/metabolismo , Organismos Aquáticos/metabolismo , Produtos Biológicos/metabolismo , Fungos/metabolismo , Microbiologia Industrial/métodos , Agroquímicos/química , Agroquímicos/isolamento & purificação , Agroquímicos/farmacologia , Organismos Aquáticos/isolamento & purificação , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/farmacologia , Técnicas de Cocultura/métodos , Fungos/isolamento & purificação , Sedimentos Geológicos/microbiologia , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Metabolômica , Phytophthora infestans/efeitos dos fármacos , Policetídeos/isolamento & purificação , Policetídeos/metabolismo , Projetos de Pesquisa , Xanthomonas campestris/efeitos dos fármacos
8.
Phytochemistry ; 170: 112191, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31731236

RESUMO

Seven undescribed polyketides javanicols A-E, 5-epi-citreoviridin and 5-epi-isocitreoviridin, together with five known compounds, were isolated from the endolichenic fungus Eupenicillium javanicum. The structures of these polyketides were determined by means of extensive spectroscopic analyses, electronic circular dichroism (ECD) calculations and gauge-independent atomic orbital (GIAO) NMR shift calculations. These compounds were evaluated for potential anti-inflammatory activity against LPS-activated RAW 264.7 cells. Javanicol E and (+)-terrein displayed moderate inhibitory effects on NO production, with IC50 values of 17.00 and 13.46 µM, respectively.


Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Eupenicillium/química , Óxido Nítrico/antagonistas & inibidores , Policetídeos/farmacologia , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Óxido Nítrico/biossíntese , Compostos Fitoquímicos , Policetídeos/química , Policetídeos/isolamento & purificação , Células RAW 264.7
9.
Nat Prod Res ; 34(7): 958-964, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30600715

RESUMO

Chemical epigenetic manipulation was applied to explore secondary metabolite of an endophytic fungus Penicillium herquei, which was obtained from the fruiting body of Cordyceps sinensis, and three previously undescribed polyketides with pyran-2-one scaffold were isolated from its fermentation broth containing 10 mg/L 5-aza-2-deoxycytidine (a frequently-used DNA methyltransferase inhibitor). The structures of these new compounds were identified by extensive spectroscopic analyses, and their absolute configurations were elucidated by quantum chemical ECD calculations.


Assuntos
Cordyceps/química , Epigênese Genética , Penicillium/química , Pironas/isolamento & purificação , Fermentação , Estrutura Molecular , Penicillium/genética , Penicillium/isolamento & purificação , Policetídeos/química , Policetídeos/isolamento & purificação , Análise Espectral
10.
Mar Drugs ; 17(12)2019 Dec 05.
Artigo em Inglês | MEDLINE | ID: mdl-31817515

RESUMO

The chemical examination of the solid cultures of the deep-sea-derived fungus Penicillium chrysogenum MCCC 3A00292 resulted in the isolation of three new versiol-type analogues, namely peniciversiols A-C (1-3), and two novel lactone derivatives, namely penicilactones A and B (6 and 7), along with 11 known polyketides. The planar structures of the new compounds were determined by the comprehensive analyses of the high-resolution electrospray ionization mass spectroscopy (HRESIMS) and nuclear magnetic resonance (NMR) data, while their absolute configurations were resolved on the basis of comparisons of the experimental electronic circular dichroism (ECD) spectra with the calculated ECD data. Compound 1 is the second example of versiols featuring a 2,3-dihydropyran-4-one ring. Additionally, compounds 6 and 7 are the first representatives of γ-lactone derivatives constructed by a 1,3-dihydroxy-5-methylbenzene unit esterifying with the α-methyl-γ-hydroxy-γ-acetic acid α,ß-unsaturated-γ-lactone moiety and α-hydroxy-γ-methyl-γ-acetic acid α,ß-unsaturated-γ-lactone unit, respectively. All of the isolated compounds were evaluated for their cytotoxic activities against five human cancer cell lines of BIU-87, ECA109, BEL-7402, PANC-1, and Hela-S3. Compound 1 exhibited a selective inhibitory effect against the BIU-87 cell line (IC50 = 10.21 µM), while compounds 4, 5, 8, and 12-16 showed inhibitory activities against the ECA109, BIU-87, and BEL-7402 cell lines with the IC50 values ranging from 7.70 to > 20 µM.


Assuntos
Antineoplásicos/farmacologia , Penicillium chrysogenum/química , Policetídeos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Dicroísmo Circular , Humanos , Espectroscopia de Ressonância Magnética , Neoplasias/tratamento farmacológico , Policetídeos/química , Policetídeos/isolamento & purificação , Espectrometria de Massas por Ionização por Electrospray
11.
Int. microbiol ; 22(4): 451-459, dic. 2019. graf, tab
Artigo em Inglês | IBECS | ID: ibc-185063

RESUMO

An endophytic actinomycete strain SKH1-2 isolated from Musa (ABB) cv. 'Kluai Sao Kratuep Ho' collected in Suphan Buri province (14° 54′ 22.5″ N/100° 04′ 50″ E), Thailand, was identified as Streptomyces pseudovenezuelae based on phenotypic and chemotaxonomic characteristics, and 16S rRNA sequence analyses. A chemical investigation led to the isolation of two polyketide molecules from the n-butanol crude extract of the strain SKH1-2 culture broth. The compounds were purified using various chromatographic techniques and identified using spectroscopic methods compared with earlier published data. Compound 1, chartreusin, is known as an anti-Gram (+) bacterial compound and was active against Bacillus subtilis ATCC 6633, Kocuria rhizophila ATCC 9341 and Staphylococcus aureus ATCC 6538p with MIC values of 3.1, 1.6 and 12.5 μg/mL, respectively. Compound 2, lumichrome, did not show activity against all tested microbes. To our knowledge, this is the first report of chartreusin and lumichrome isolated from S. pseudovenezuelae. Taken together, it could be proved that Thai plant species are valuable reservoirs of interesting endophytic actinomycetes producing several interesting biologically active compounds


No disponible


Assuntos
Policetídeos/isolamento & purificação , Streptomyces/isolamento & purificação , RNA Ribossômico 16S/isolamento & purificação , Staphylococcus aureus/isolamento & purificação , Streptomyces/classificação , Musa/química , Musa/microbiologia , RNA Ribossômico 16S/química , Análise Espectral
12.
Mar Drugs ; 18(1)2019 Dec 24.
Artigo em Inglês | MEDLINE | ID: mdl-31878313

RESUMO

Marine-derived fungi have been reported to have great potential to produce structurally unique metabolites. Our investigation on secondary metabolites from marine-derived fungi resulted in the isolation of seven new polyketides (phomopsiketones D-G (1-4) and letendronols A-C (5-7)) as well as one known xylarinol (8) in the cultural broth of Letendraea sp. Their structures and absolute configurations were elucidated using a set of spectroscopic and chemical methods, including HRESIMS, NMR, single-crystal X-ray diffraction, ECD calculation, and a modified version of Mosher's method. Compound 2 showed weak inhibition against nitric oxide production in lipopolysaccaride-activated macrophages with an IC50 value of 86 µM.


Assuntos
Ascomicetos/química , Policetídeos/química , Policetídeos/isolamento & purificação , Animais , Antibacterianos/farmacologia , Linhagem Celular Tumoral/efeitos dos fármacos , Cristalografia por Raios X , Decápodes/microbiologia , Bactérias Gram-Negativas/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Oceanos e Mares , Policetídeos/farmacologia , Células RAW 264.7
13.
Fitoterapia ; 139: 104369, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31626911

RESUMO

Five new polyketides, colletotric B (2), 3-hydroxy-5-methoxy-2,4,6-trimethylbenzoic acid (3), colletotric C (4), chaetochromone D (6) and 8-hydroxy-pregaliellalactone B (9), together with four known analogues (1, 5 and 7-8) were isolated from the mangrove endophytic fungus Phoma sp. SYSU-SK-7. Their structures were elucidated by analysis of extensive spectroscopic data and mass spectrometric data. Compounds 1-2 showed strong antimicrobial activity against the P. aeruginosa, MRSA and C. albicans with the MIC values in the range of 1.67-6.28 µg/ml. Furthermore, Compounds 1-5 also exhibited significant α-glucosidase inhibitory activity with the IC50 values in the range of 36.2-90.6 µM. Compound 7 was found to inhibited radical scavenging activity against DPPH with the EC50 value of 11.8 µM.


Assuntos
Anti-Infecciosos/farmacologia , Ascomicetos/química , Depuradores de Radicais Livres/farmacologia , Inibidores de Glicosídeo Hidrolases/farmacologia , Policetídeos/farmacologia , Rhizophoraceae/microbiologia , Anti-Infecciosos/isolamento & purificação , China , Endófitos/química , Depuradores de Radicais Livres/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura Molecular , Policetídeos/isolamento & purificação
14.
Mar Drugs ; 17(11)2019 Oct 24.
Artigo em Inglês | MEDLINE | ID: mdl-31653089

RESUMO

Five hybrid polyketides (1a, 1b, and 2-4) containing tetramic acid core including a new hybrid polyketide, cladosin L (1), were isolated from the marine fungus Cladosporium sphaerospermum SW67, which was isolated from the marine hydroid polyp of Hydractinia echinata. The hybrid polyketides were isolated as a pair of interconverting geometric isomers. The structure of 1 was determined based on 1D and 2D NMR spectroscopic and HR-ESIMS analyses. Its absolute configuration was established by quantum chemical electronic circular dichroism (ECD) calculations and modified Mosher's method. Tetramic acid-containing compounds are reported to be derived from a hybrid PKS-NRPS, which was also proved by analyzing our 13C-labeling data. We investigated whether compounds 1-4 could prevent cell damage induced by cisplatin, a platinum-based anticancer drug, in LLC-PK1 cells. Co-treatment with 2 and 3 ameliorated the damage of LLC-PK1 cells induced by 25 µM of cisplatin. In particular, the effect of compound 2 at 100 µM (cell viability, 90.68 ± 0.81%) was similar to the recovered cell viability of 88.23 ± 0.25% with 500 µM N-acetylcysteine (NAC), a positive control.


Assuntos
Cladosporium/genética , Policetídeos/química , Policetídeos/farmacologia , Pirrolidinonas/química , Pirrolidinonas/farmacologia , Animais , Antineoplásicos/efeitos adversos , Sobrevivência Celular/efeitos dos fármacos , Cisplatino/efeitos adversos , Cladosporium/química , Células LLC-PK1 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Filogenia , Policetídeos/isolamento & purificação , Suínos
15.
Molecules ; 24(18)2019 Sep 17.
Artigo em Inglês | MEDLINE | ID: mdl-31533358

RESUMO

Drug-like molecules are known to contain many different building blocks with great potential as pharmacophores for drug discovery. The continued search for unique scaffolds in our laboratory led to the isolation of a novel Ghanaian soil bacterium, Streptomyces sp. MA37. This strain produces many bioactive molecules, most of which belong to carbazoles, pyrrolizidines, and fluorinated metabolites. Further probing of the metabolites of MA37 has led to the discovery of a new naphthacene-type aromatic natural product, which we have named accramycin A 1. This molecule was isolated using an HPLC-photodiode array (PDA) guided isolation process and MS/MS molecular networking. The structure of 1 was characterized by detailed analysis of LC-MS, UV, 1D, and 2D NMR data. Preliminary studies on the antibacterial properties of 1 using Group B Streptococcus (GBS) produced a minimum inhibitory concentration (MIC) of 27 µg/mL. This represents the first report of such bioactivity amongst the naphthacene-type aromatic polyketides, and also suggests the possibility for the further development of potent molecules against GBS based on the accramycin scaffold. A putative acc biosynthetic pathway for accramycin, featuring a tridecaketide-specific type II polyketide synthase, was proposed.


Assuntos
Policetídeos/química , Policetídeos/isolamento & purificação , Microbiologia do Solo , Streptomyces/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/farmacologia , Vias Biossintéticas , Genes Bacterianos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Família Multigênica , Policetídeos/metabolismo , Policetídeos/farmacologia , Streptomyces/genética , Streptomyces/metabolismo
16.
Molecules ; 24(17)2019 Aug 22.
Artigo em Inglês | MEDLINE | ID: mdl-31443573

RESUMO

Two new chromone-derived polyketides phaseolorins, G and H (1 and 2), and one new anthraquinone derivative, phaseolorin I (3), together with three known compounds (4-6), were isolated from the deep-sea sediment-derived fungus Diaporthe phaseolorum FS431. The structures of the new compounds were determined by comprehensive analysis of their spectroscopic data, and the absolute configuration of 1 was established by quantum chemical calculations of electron capture detection (ECD). All the isolated compounds (1-6) were tested for their in vitro cytotoxic activities against four human tumor cell lines, of which compound 4 exhibited significant effect against MCF-7, HepG-2, and A549 tumor cell lines with IC50 values of 2.60, 2.55, and 4.64 µM, respectively.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Microbiologia Ambiental , Fungos/química , Sedimentos Geológicos/microbiologia , Policetídeos/química , Policetídeos/farmacologia , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Espectroscopia de Ressonância Magnética , Oceanos e Mares , Policetídeos/isolamento & purificação , Relação Estrutura-Atividade
17.
Chem Biodivers ; 16(9): e1900326, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31368179

RESUMO

Chromatographic separation of the AcOEt extract of the fermented cultures of the deep-sea-derived fungus Graphostroma sp. resulted in the isolation of 11 new chained polyketides, namely graphostromols A-K (1-11). The structures of the new compounds were established by the extensive analyses of their NMR and HR-ESI-MS data. The absolute configuration at C-11 in 1 was determined on the basis of the modified Mosher's method. Compounds 1-5, bearing a 2,2,10,10-tetramethyldodecane skeleton, were discovered for the first time from nature. All isolates were evaluated for their cytotoxicities against five different cancer cell lines (HeLa, Eca-109, Biu-87, Bel-7402, and PANC-1). However, none showed positive effects.


Assuntos
Policetídeos/química , Linhagem Celular Tumoral , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Policetídeos/isolamento & purificação
18.
Fitoterapia ; 137: 104282, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31381956

RESUMO

Four new polyketides, alternatains A-D (1-4), along with 17 known compounds (5-21) were obtained from the solid substrate fermentation cultures of Alternaria alternata MT-47, an endophytic fungus isolated from the medicinal plant of Huperzia serrata. Their structures were elucidated by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, IR, and HRESIMS) and calculated electronic circular dichroism (ECD) method. Compounds 4, 6, 15, and 21 exhibited inhibitory activities on ATP release of thrombin-activated platelets with IC50 values in the range of 18.2-68.8 µM.


Assuntos
Alternaria/química , Anticoagulantes/farmacologia , Plaquetas/efeitos dos fármacos , Huperzia/microbiologia , Policetídeos/farmacologia , Acetilcolinesterase , Trifosfato de Adenosina , Anticoagulantes/isolamento & purificação , Butirilcolinesterase , China , Inibidores da Colinesterase , Endófitos/química , Humanos , Estrutura Molecular , Plantas Medicinais/microbiologia , Policetídeos/isolamento & purificação
19.
Zhongguo Zhong Yao Za Zhi ; 44(10): 2090-2095, 2019 May.
Artigo em Chinês | MEDLINE | ID: mdl-31355566

RESUMO

To isolate and identify secondary metabolites of marine-derived Streptomyces sp.MDW-06,the isolations and purifications of compounds were performed by means of column chromatography over silica gel. And their structures were elucidated through the spectroscopic analysis of MS,NMR and specific rotations. The bioactivities were assayed by paper diffusion and DPPH method. From the fermentation broth of marine-derived Streptomyces sp.MDW-06,five compounds( 1-5) were isolated and identified as streptopentanoic acid( 1),germicidin A( 2),germicidin B( 3),isogermicidin A( 4),isogermicidin B( 5) and oxohygrolidin( 6),respectively. Compound 1 is a new compound. Compound 1 shows DPPH radical scavenging activity with 36. 4% at 100 mg·L~(-1).


Assuntos
Depuradores de Radicais Livres/química , Policetídeos/química , Streptomyces/química , Cromatografia , Fermentação , Depuradores de Radicais Livres/isolamento & purificação , Espectroscopia de Ressonância Magnética , Policetídeos/isolamento & purificação
20.
Molecules ; 24(14)2019 Jul 22.
Artigo em Inglês | MEDLINE | ID: mdl-31336683

RESUMO

Four new compounds, including two new polyketides, heterocornols M and N (1, 2), and a pair of epimers, heterocornols O and P (3, 4), were isolated from the fermentation broth of the marine sponge-derived fungus Pestalotiopsis heterocornis XWS03F09, together with three known compounds (5-7). The new chemical structures were established on the basis of a spectroscopic analysis, optical rotation, experimental and calculated electronic circular dichroism (ECD). All of the compounds (1-7) were evaluated for their cytotoxic activities, and heterocornols M-P (1-4) exhibited cytotoxicities against four human cancer cell lines with IC50 values of 20.4-94.2 µM.


Assuntos
Organismos Aquáticos/microbiologia , Ascomicetos/química , Produtos Biológicos/farmacologia , Policetídeos/farmacologia , Poríferos/microbiologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Humanos , Modelos Moleculares , Estrutura Molecular , Policetídeos/química , Policetídeos/isolamento & purificação , Análise Espectral
SELEÇÃO DE REFERÊNCIAS
DETALHE DA PESQUISA