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1.
Prog Chem Org Nat Prod ; 111: 81-153, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32114663

RESUMO

Marine-derived fungi play an important role in the search for structurally unique secondary metabolites, some of which show promising pharmacological activities that make them useful leads for drug discovery. Marine natural product research in China in general has made enormous progress in the last two decades as described in this chapter on fungal metabolites. This contribution covers 613 new natural products reported from 2001 to 2017 from marine-derived fungi obtained from algae, sponges, corals, and other marine organisms from Chinese waters. The genera Aspergillus (170 new natural products, 28%) and Penicillium (70 new natural products, 11%) were the main fungal producers of new natural products during the time period covered, whereas sponges (184 new natural products, 30%) were the most abundant source of new natural products, followed by corals (154 new natural products, 25%) and algae (130 new natural products, 21%). Close to 40% of all natural products covered in this contribution displayed various bioactivities. The major bioactivities reported were cytotoxicity against different cancer cell lines, antimicrobial (mainly antibacterial) activity, and antiviral activity, which accounted for 13%, 9%, and 3% of all natural products reported. In terms of structural classes, polyketides (188 new natural products, 31%) play a dominant role, and if prenylated polyketides and nitrogen-containing polyketides (included in meroterpenes and alkaloids in this contribution) are taken into account, their total number even exceeds 50%. Nitrogen-containing compounds including peptides (65 new natural products, 10%) and alkaloids (103 new natural products, 17%) are the second largest group.


Assuntos
Produtos Biológicos/farmacologia , Fungos/química , Policetídeos/farmacologia , Animais , Antozoários/microbiologia , Anti-Infecciosos , Antineoplásicos , Organismos Aquáticos/microbiologia , Aspergillus/química , Produtos Biológicos/química , China , Penicillium/química , Policetídeos/química , Poríferos/microbiologia , Metabolismo Secundário
2.
Phytochemistry ; 170: 112224, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31812919

RESUMO

Six undescribed azaphilones, deflectins C1-C3, deflectins D1-D2, and deflectin E, along with five known azaphilones were obtained from a solid culture of the wild fungus Aspergillus deflectus NCC0415. Their structures were determined by HRESIMS, NMR and ECD analyses, together with the GIAO 13C NMR calculation method. All compounds displayed strong or moderate inhibitory activity against protein tyrosine phosphatases SHP2 and PTP1B. Structure-activity relationship analysis of these azaphilones suggested that the length of the ketone aliphatic side chain would affect their SHP2 and PTP1B inhibitory activity. In addition, the presence of a Δ8(12) double bond on γ-lactone ring and the presence of CH3-2' in fatty chains may increase their inhibitory activity.


Assuntos
Aspergillus/química , Benzopiranos/farmacologia , Inibidores Enzimáticos/farmacologia , Compostos Fitoquímicos/farmacologia , Pigmentos Biológicos/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Benzopiranos/química , Benzopiranos/isolamento & purificação , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Humanos , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Pigmentos Biológicos/química , Pigmentos Biológicos/isolamento & purificação , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Relação Estrutura-Atividade
3.
Fitoterapia ; 140: 104406, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31698061

RESUMO

One new quinoline alkaloid (1), two new bisabolane-type sesquiterpene derivatives (2 and 3), and a new natural product (4) along with ten known compounds (514) were isolated from the deep sea-derived fungus Aspergillus sp. SCSIO06786 which cultured on solid rice medium. Three new structures were elucidated by analysis of 1D/2D NMR data and HR-ESI-MS. The absolute configurations of 2 and 3 were established by comparison of the experimental and reported ECD values. Compounds 11-13 exhibited moderate selective inhibitory activities against the tested pathogenic bacteria with MIC values among 3.13-12.5 µg/mL.


Assuntos
Alcaloides/isolamento & purificação , Aspergillus/química , Quinolinas/isolamento & purificação , Água do Mar/microbiologia , Sesquiterpenos/isolamento & purificação , Alcaloides/farmacologia , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Sedimentos Geológicos/microbiologia , Oceano Índico , Testes de Sensibilidade Microbiana , Estrutura Molecular , Quinolinas/farmacologia , Sesquiterpenos/farmacologia
4.
Food Microbiol ; 86: 103311, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-31703856

RESUMO

Filamentous fungi are one of the main causes of food losses worldwide and their ability to produce mycotoxins represents a hazard for human health. Their correct and rapid identification is thus crucial to manage food safety. In recent years, MALDI-TOF emerged as a rapid and reliable tool for fungi identification and was applied to typing of bacteria and yeasts, but few studies focused on filamentous fungal species complex differentiation and typing. Therefore, the aim of this study was to evaluate the use of MALDI-TOF to identify species of the Aspergillus section Flavi, and to differentiate Penicillium roqueforti isolates from three distinct genetic populations. Spectra were acquired from 23 Aspergillus species and integrated into a database for which cross-validation led to more than 99% of correctly attributed spectra. For P. roqueforti, spectra were acquired from 63 strains and a two-step calibration procedure was applied before database construction. Cross-validation and external validation respectively led to 94% and 95% of spectra attributed to the right population. Results obtained here suggested very good agreement between spectral and genetic data analysis for both Aspergillus species and P. roqueforti, demonstrating MALDI-TOF applicability as a fast and easy alternative to molecular techniques for species complex differentiation and strain typing of filamentous fungi.


Assuntos
Aspergillus/isolamento & purificação , Técnicas de Tipagem Micológica/métodos , Penicillium/isolamento & purificação , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz/métodos , Aspergillus/química , Aspergillus/classificação , Contaminação de Alimentos/análise , Microbiologia de Alimentos , Penicillium/química , Penicillium/classificação
5.
Pol J Microbiol ; 68(3): 309-316, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31880876

RESUMO

Among the species belonging to the Aspergillus section Versicolores, Aspergillus creber has been poorly studied and still unexplored for its biological activities. The present study was undertaken to analyze A. creber extract and to evaluate its in vitro antimicrobial and anti-oxidant activities. UHPLC-MS/MS analysis of A. creber extract allowed the characterization of five known fungal metabolites including: asperlactone, emodin, sterigmatocystin, deoxybrevianamide E, and norsolorinic acid. The highest antimicrobial activity was displayed against Candida albicans, with a mean strongest inhibition zone of 20.6 ± 0.8 mm, followed by Gram-positive drug-resistant bacteria. The MIC values of A. creber extract varied from 0.325 mg/ml to 5 mg/ml. A. creber extract was shown a potent antioxidant activity and a high level of phenolic compounds by recording 89.28% scavenging effect for DPPH free radical, 92.93% in ABTS assay, and 85.76 mg gallic acid equivalents/g extract in Folin-Ciocalteu assay. To our knowledge, this is the first study concerning biological and chemical activities of A. creber species. Based on the obtained results, A. creber could be a promising source of natural antimicrobial and antioxidant compounds.Among the species belonging to the Aspergillus section Versicolores, Aspergillus creber has been poorly studied and still unexplored for its biological activities. The present study was undertaken to analyze A. creber extract and to evaluate its in vitro antimicrobial and anti-oxidant activities. UHPLC-MS/MS analysis of A. creber extract allowed the characterization of five known fungal metabolites including: asperlactone, emodin, sterigmatocystin, deoxybrevianamide E, and norsolorinic acid. The highest antimicrobial activity was displayed against Candida albicans, with a mean strongest inhibition zone of 20.6 ± 0.8 mm, followed by Gram-positive drug-resistant bacteria. The MIC values of A. creber extract varied from 0.325 mg/ml to 5 mg/ml. A. creber extract was shown a potent antioxidant activity and a high level of phenolic compounds by recording 89.28% scavenging effect for DPPH free radical, 92.93% in ABTS assay, and 85.76 mg gallic acid equivalents/g extract in Folin-Ciocalteu assay. To our knowledge, this is the first study concerning biological and chemical activities of A. creber species. Based on the obtained results, A. creber could be a promising source of natural antimicrobial and antioxidant compounds.


Assuntos
Antifúngicos/química , Antifúngicos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Aspergillus/química , Candida albicans/efeitos dos fármacos , Candida albicans/crescimento & desenvolvimento , Testes de Sensibilidade Microbiana , Fenóis/química , Fenóis/farmacologia , Espectrometria de Massas em Tandem
6.
Artigo em Inglês | MEDLINE | ID: mdl-31535946

RESUMO

Infestation of food crops by fungi has led to serious economic losses in the international market. There is a paucity of information on the multi-mycotoxin profile of cashew nuts from different geographical locations in Nigeria and South Africa. This work aims at comparing the fungal metabolite profile of cashew nut from two African countries using HPLC-FLD and LC-MS/MS. The differences in distribution of the fungal metabolites across the two countries were also examined. A total of 75 (39; Nigeria, 36; South Africa) roasted cashew nuts were purchased from 14 different locations in Nigeria and 10 major supermarkets in South Africa. The samples were subjected to HPLC analysis for aflatoxin and zearalenone and LC-MS/MS analysis for multiple metabolite profiling. Total aflatoxins (0.03-0.77 µg/kg and 0.01-0.28 µg/kg) and zearalenone (123.2 and 788.6 µg/kg) were quantified in nut samples from South Africa and Nigeria, respectively. In contrast, LC-MS/MS analysis showed that none of the major fungi metabolites except for one (citrinin) was present in detectable amount in Nigerian cashew nuts (31.3 µg/kg). Other microbial metabolites present in the nuts were; Aspergillus metabolites (< LOD to 398 × 104 µg/kg and < LOD to 1760 µg/kg); flavoglaucin (5.4-177.4 µg/kg and 45.5-18,368 µg/kg), 7-hydroxykaurenolide (5.5-45.8 µg/kg and 3.5-33.7 µg/kg), chloramphenicol (0.3-4.5 µg/kg) for South African and Nigerian cashew nuts, respectively. The incidence rate of the fusarium toxins beauvericin and bikaverin were higher in Nigerian cashew nut (100% and 17%) than the South African nuts (8% and 8%), 7-Hydroxykaurenolide and chloramphenicol were found in all the cashew nut samples. A total of 15 unspecific metabolites (17-100%) were recorded in the nuts from both countries. Information on the metabolite profile of cashew nuts will provide useful information for policy makers, border agencies and other health-related Institutes.


Assuntos
Anacardium/química , Aspergillus/química , Aspergillus/metabolismo , Contaminação de Alimentos/análise , Micotoxinas/análise , Anacardium/metabolismo , Nigéria , África do Sul
7.
J Agric Food Chem ; 67(38): 10660-10666, 2019 Sep 25.
Artigo em Inglês | MEDLINE | ID: mdl-31479263

RESUMO

Two new indolyl diketopiperazines, gartryprostatins A and B (1 and 2), with an unusual 2,3-furan-fused pyrano[2,3-g]pyrrolo[1″,2″:4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole nucleus, along with a new naturally occurring compound (gartryprostatin C, 3) were isolated from the solid culture of Aspergillus sp. GZWMJZ-258, an endophyte from Garcinia multiflora (Guttiferae). The structures of compounds 1-3 were determined by nuclear magnetic resonance, mass spectrometry, Marfey's analysis of amino acids, and chemical calculation. Compounds 1-3 displayed selective inhibition on human FLT3-ITD mutant AML cell line, MV4-11, with IC50 values of 7.2, 10.0, and 0.22 µM, respectively.


Assuntos
Aspergillus/química , Dicetopiperazinas/farmacologia , Endófitos/química , Garcinia/microbiologia , Plantas Medicinais/microbiologia , Aspergillus/genética , Aspergillus/isolamento & purificação , Aspergillus/metabolismo , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Dicetopiperazinas/química , Dicetopiperazinas/metabolismo , Endófitos/genética , Endófitos/isolamento & purificação , Endófitos/metabolismo , Humanos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular
8.
Mar Drugs ; 17(8)2019 Aug 18.
Artigo em Inglês | MEDLINE | ID: mdl-31426620

RESUMO

Three new benzofuranoids, asperfuranoids A-C (1-3), two new phenylpropanoid derivatives (6 and 7), and nine known analogues (4, 5, and 8-14) were isolated from the liquid substrate fermentation cultures of the mangrove endopytic fungus Aspergillus sp. ZJ-68. The structures of the new compounds were determined by extensive spectroscopic data interpretation. The absolute configurations of 1-3 were assigned via the combination of Mosher's method, and experimental and calculated electronic circular dichroism (ECD) data. Compounds 4 and 5 were a pair of enantiomers and their absolute configurations were established for the first time on the basis of their ECD spectra aided with ECD calculations. All isolated compounds (1-14) were evaluated for their enzyme inhibitory activity against α-glucosidase and antibacterial activities against four pathogenic bacteria (Staphylococcus aureus, Escherichia coli, Bacillus subtilis, and Pseudomonas aeruginosa). Among them, compound 6 exhibited potent inhibitory activity against α-glucosidase in a standard in vitro assay, with an IC50 value of 12.4 µM, while compounds 8 and 11 showed activities against S. aureus, E. coli, and B. subtilis, with MIC values in the range of 4.15 to 12.5 µg/mL.


Assuntos
Aspergillus/química , Propanóis/química , Antibacterianos/química , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Produtos Biológicos/química , Produtos Biológicos/farmacologia , Testes de Sensibilidade Microbiana , Propanóis/farmacologia
9.
Artigo em Inglês | MEDLINE | ID: mdl-31437087

RESUMO

Food decay by spoilage fungi leads to significant economic losses and hazards to consumers' health due to the potential of mycotoxin occurrence. Ochratoxin A (OTA) is a mycotoxin known as nephrotoxic and carcinogenic to humans. Natural capsaicin was evaluated for its effectiveness against the growth of five Aspergillus section Nigri strains and accumulation of OTA in inoculated black grapes. Results showed that capsaicin was effective in inhibiting fungal growth and OTA production by new four Aspergillus section Nigri strains (ATHUM 6997, 6998, 6999, 7000) and by Aspergillus carbonarius as well. Moreover, capsaicin addition exhibited maximum inhibition of OTA produced by ATHUM 6997, 6998, 6999, and 7000 in black grapes at 28.9%, 8.6%, 68.4%, and 78.1%, respectively. Inhibition percentage of OTA production by A. carbonarius in grapes treated with capsaicin was estimated at 61.5%. These results suggest that capsaicin influences the OTA biosynthesis pathway of all Aspergillus section Nigri strains and therefore could be used as an effective natural preservative against OTA contamination of vineyards. Risk assessment revealed that when grapes are treated with capsaicin, consumers are less exposed to OTA.


Assuntos
Antifúngicos/farmacologia , Aspergillus/efeitos dos fármacos , Capsaicina/farmacologia , Ocratoxinas/antagonistas & inibidores , Vitis/microbiologia , Antifúngicos/química , Antifúngicos/metabolismo , Aspergillus/química , Aspergillus/crescimento & desenvolvimento , Capsaicina/química , Capsaicina/metabolismo , Testes de Sensibilidade Microbiana , Ocratoxinas/metabolismo
10.
Mar Drugs ; 17(8)2019 Jul 30.
Artigo em Inglês | MEDLINE | ID: mdl-31366127

RESUMO

Preussin, a hydroxyl pyrrolidine derivative isolated from the marine sponge-associated fungus Aspergillus candidus KUFA 0062, displayed anticancer effects in some cancer cell lines, including MCF7. Preussin was investigated for its cytotoxic and antiproliferative effects in breast cancer cell lines (MCF7, SKBR3, and MDA-MB-231), representatives of major breast cancers subtypes, and in a non-tumor cell line (MCF12A). Preussin was first tested in 2D (monolayer), and then in 3D (multicellular aggregates), cultures, using a multi-endpoint approach for cytotoxicity (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), resazurin and lactate dehydrogenase (LDH)) and proliferative (5-bromo-2'-deoxyuridine (BrdU)) assays, as well as the analysis of cell morphology by optical/electron microscopy and immunocytochemistry for caspase-3 and ki67. Preussin affected cell viability and proliferation in 2D and 3D cultures in all cell lines tested. The results in the 3D culture showed the same tendency as in the 2D culture, however, cells in the 3D culture were less responsive. The effects were observed at different concentrations of preussin, depending on the cell line and assay method. Morphological study of preussin-exposed cells revealed cell death, which was confirmed by caspase-3 immunostaining. In view of the data, we recommend a multi-endpoint approach, including histological evaluation, in future assays with the tested 3D models. Our data showed cytotoxic and antiproliferative activities of preussin in breast cancer cell lines in 2D and 3D cultures, warranting further studies for its anticancer potential.


Assuntos
Anisomicina/análogos & derivados , Antineoplásicos/farmacologia , Aspergillus/química , Neoplasias da Mama/tratamento farmacológico , Poríferos/microbiologia , Animais , Anisomicina/farmacologia , Neoplasias da Mama/patologia , Técnicas de Cultura de Células , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Células MCF-7
11.
J Antibiot (Tokyo) ; 72(10): 729-735, 2019 10.
Artigo em Inglês | MEDLINE | ID: mdl-31289369

RESUMO

The first calcium complex from nature, Coumamarin (1), 7-hydroxy-3-methoxy-2-oxo-2H-chromene-6-carboxylate Ca(II) complex, was isolated from Aspergillus sydowii ASTI, together with diorcinol (2), violaceol I (3), hydroxysydonic acid (4), cyclo (Trp-Phe), kojic acid, ergosterol, and uracil. The producing strain was isolated from marine water sample collected from Tiran Island, Red Sea, Egypt. Structure 1 was assigned by intensive 1D, 2D NMR, HR-ESIMS, and X-ray crystallography as well. Coumamarin is potentially active against certain tested bacteria and yeasts, while showing no cytotoxic activity against human cervix carcinoma cell line (KB-3-1). Taxonomically, the fungus was identified by phylogenetic analysis of its 18S rRNA gene sequence.


Assuntos
Aspergillus/química , Produtos Biológicos/isolamento & purificação , Aspergillus/classificação , Aspergillus/genética , Aspergillus/isolamento & purificação , Produtos Biológicos/química , Análise por Conglomerados , DNA Fúngico/química , DNA Fúngico/genética , DNA Ribossômico/química , DNA Ribossômico/genética , Egito , Oceano Índico , Estrutura Molecular , Filogenia , RNA Ribossômico 18S/genética , Água do Mar/microbiologia , Análise de Sequência de DNA , Análise Espectral
12.
Artigo em Inglês | MEDLINE | ID: mdl-31314691

RESUMO

Tofu or bean curd is obtained from soybean seeds being a widespread food product in Asia. The commodity used for its production can be contaminated with aflatoxins, which are secondary metabolites synthetised by species of Aspergillus flavus and A. parasiticus. Intake of contaminated food products causes toxic effects on consumers. The aim of this work was to study aflatoxin distribution in fractions obtained from pilot-scale tofu production with contaminated soybeans. The presence of the aflatoxins B1, B2, G1 and G2 (AFs) in soaking water, okara, whey and tofu was analysed. Aflatoxin analysis was performed by HPLC with fluorescence detection. The distribution of aflatoxins in all the analysed fractions was not a normal distribution. The liquid fractions (soaking water and whey) had less contamination than solid fractions (tofu and okara). The percentage AFB1 remaining in nutritionally important fractions, okara and tofu, was between 6.2% and 67.7% (median = 18.1%) and 0.5% and 13.2% (median = 3.5%), respectively. AFB2, AFG1 and AFG2 had a similar distribution. These results showed that throughout tofu production, AFs can be present in the products intended for human consumption.


Assuntos
Aflatoxinas/análise , Contaminação de Alimentos/análise , Alimentos de Soja/análise , Aspergillus/química , Humanos
13.
Fish Shellfish Immunol ; 93: 8-16, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31319205

RESUMO

High levels of soybean meal (SBM) in aquafeed leads to detrimental inflammatory response and oxidative stress in fish. In the present study, fermentation with Aspergillus awamori was conducted to explore the potential effects on improving the nutritional quality of soybean meal and the health status of turbot. A 63-day feeding trial (initial weight 8.53 ±â€¯0.11 g) was carried out to evaluate the utilization of fermented soybean meal (FSM) by juvenile turbot. 0% (FM, control), 30% (S30, F30), 45% (S45, F45), and 60% (S60, F60) of fish meal were replaced with SBM or FSM, respectively. As the results showed, fermentation significantly reduced the contents of anti-nutritional factors in SBM, including raffinose (-98.8%), glycinin (-98.5%), ß-conglycinin (-97.4%), trypsin inhibitors (-80%) and stachyose (-80%). A depression of fish growth performance and activities of superoxide dismutase and lysozyme were observed in S45 and S60 groups, while these inferiorities were only observed in F60 group. Meanwhile, fermentation also improved the heights of enterocytes and microvillus significantly in the F45 and F60 groups compared with those in SBM. An induced expression of anti-inflammatory cytokine transforming growth factor-ß and depression of pro-inflammatory cytokines tumor necrosis factor-α and interleukin-1ß in the distal intestine were observed in the F45 and F60 groups. Taken together, this study indicated that fermentation with Aspergillus awamori could improve the replacement level with soybean meal from 30% to 45% in turbot.


Assuntos
Antioxidantes/metabolismo , Aspergillus/química , Linguados/imunologia , Estresse Oxidativo/imunologia , Alimentos de Soja/análise , Soja/química , Ração Animal/análise , Animais , Dieta/veterinária , Fermentação , Linguados/crescimento & desenvolvimento , Linguados/metabolismo , Homeostase , Distribuição Aleatória
14.
Artigo em Inglês | MEDLINE | ID: mdl-31294650

RESUMO

The present study examines the influence of the natural preservatives carvacrol, eugenol, trans-cinnamaldehyde and the essential oil (EO) Origanum vulgare on ochratoxin A (OTA) production and the mycelial growth of two food-related moulds, Penicillium verrucosum and Aspergillus westerdijkiae, by broth macro-dilution assay for 21 days. With the addition of ½ minimum inhibitory concentration (MIC) carvacrol, eugenol and O. vulgare EO, the mycelial dry weight of both moulds decreased significantly over the whole incubation period of 7, 14 and 21 days. Trans-cinnamaldehyde slightly stimulated the growth of A. westerdijkiae and P. verrucosum at 14 and 21 days of incubation. Growth inhibition did not accompany inhibition of OTA production. Although the growth of both moulds was inhibited after the addition of ½ MIC carvacrol, eugenol and O. vulgare EO, the OTA production of the strong mycotoxin producer A. westerdijkiae was stimulated. Only trans-cinnamaldehyde inhibited the production of OTA with the addition of ½ MIC. P. verrucosum produced significantly less OTA than A. westerdijkiae, and its mycotoxin production was almost completely inhibited by the addition of ½ MIC of the natural preservatives.


Assuntos
Aspergillus/efeitos dos fármacos , Microbiologia de Alimentos , Conservantes de Alimentos/farmacologia , Micélio/efeitos dos fármacos , Ocratoxinas/biossíntese , Penicillium/efeitos dos fármacos , Acroleína/análogos & derivados , Acroleína/química , Acroleína/farmacologia , Aspergillus/química , Eugenol/química , Eugenol/farmacologia , Conservantes de Alimentos/química , Monoterpenos/química , Monoterpenos/farmacologia , Micélio/crescimento & desenvolvimento , Ocratoxinas/química , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Penicillium/química
15.
Molecules ; 24(14)2019 Jul 21.
Artigo em Inglês | MEDLINE | ID: mdl-31330867

RESUMO

Three new γ-hydroxyl butenolides (1-3), a pair of new enantiomeric spiro-butenolides (4a and 4b), a pair of enantiomeric cyclopentenones (5a new and 5b new natural), and six known compounds (6-11), were isolated from Aspergillus sclerotiorum. Their structures were established by spectroscopic data and electronic circular dichroism (ECD) spectra. Two pairs of enantiomers [(+)/(-)-6c and (+)/(-)-6d] obtained from the reaction of 6 with acetyl chloride (AcCl) confirmed that 6 was a mixture of two pairs of enantiomers. In addition, the X-ray data confirmed that 7 was also a racemate. The new metabolites (1-5) were evaluated for their inhibitory activity against cancer and non-cancer cell lines. As a result, compound 1 exhibited moderate cytotoxicity to HL60 and A549 with IC50 values of 6.5 and 8.9 µM, respectively, and weak potency to HL-7702 with IC50 values of 17.6 µM. Furthermore, compounds 1-9 were screened for their antimicrobial activity using the micro-broth dilution method. MIC values of 200 µg/mL were obtained for compounds 2 and 3 towards Staphylococcus aureus and Escherichia coli, while compound 8 exhibited a MIC of 50 µ/mL towards Candida albicans.


Assuntos
4-Butirolactona/análogos & derivados , Aspergillus/química , Ciclopentanos/química , Microbiologia do Solo , Solo/química , 4-Butirolactona/química , 4-Butirolactona/farmacologia , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Ciclopentanos/farmacologia , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Análise Espectral , Relação Estrutura-Atividade
16.
Chem Biodivers ; 16(8): e1900237, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31241824

RESUMO

Two new compounds, named 3,4-dimethoxyphenyl α-d-ribofuranoside (1) and 3ß-(ß-d-glucopyranosyloxy)olean-12-ene-23,28,30-trioic acid (2), together with thirteen known compounds, were isolated from the white beans culture of the marine derived endophytic fungus Aspergillus amstelodami. Structure elucidation of the new compounds was carried out by one-, two-dimensional spectroscopy, and high resolution electrospray ionization mass. The antimelanogenic and anti-allergic activity of the isolated compounds were investigated. Compounds 4, 7, 1, 3, 11, 6 and 9 selectively suppressed melanin production in B16 melanoma cells, using arbutin as a positive control. Their IC50 values were 30.8±5.57, 38.5±6.08, 52.6±6.64, 98.0±1.16, 100.4±3.05, 112.0±0.22 and 144.7±2.35 µm, respectively, while that of arbutin was 151.7±1.27 µm. The tested compounds did not show any significant anti-allergic activity in RBL-2H3 cells, as compared to quercetin.


Assuntos
Aspergillus/química , Melaninas/antagonistas & inibidores , Ribose/química , Animais , Antialérgicos/química , Aspergillus/metabolismo , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Hexosaminidases/metabolismo , Espectroscopia de Ressonância Magnética , Melaninas/metabolismo , Melanoma Experimental/metabolismo , Melanoma Experimental/patologia , Camundongos , Conformação Molecular , Ratos , Ribose/farmacologia , Espectrometria de Massas por Ionização por Electrospray
17.
Mar Drugs ; 17(6)2019 Jun 03.
Artigo em Inglês | MEDLINE | ID: mdl-31163670

RESUMO

Three new butenolide derivatives, namely aspernolides N-P (1-3), together with six known analogues (4-9), were isolated from the ethyl acetate (EtOAc) extract of the deep sea-derived fungus Aspergillus terreus YPGA10. The structures of compounds 1-3 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1 and 2 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compound 1 represents the rare example of Aspergillus-derived butenolide derivatives featured by a monosubstituted benzene ring. Compounds 6-9 exhibited remarkable inhibitory effects against α-glucosidase with IC50 values of 3.87, 1.37, 6.98, and 8.06 µM, respectively, being much more active than the positive control acarbose (190.2 µM).


Assuntos
4-Butirolactona/análogos & derivados , Organismos Aquáticos/química , Aspergillus/química , Inibidores de Glicosídeo Hidrolases/farmacologia , 4-Butirolactona/química , 4-Butirolactona/isolamento & purificação , 4-Butirolactona/farmacologia , Acetatos/química , Dicroísmo Circular , Ativação Enzimática/efeitos dos fármacos , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas
18.
Phytochemistry ; 165: 112041, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31203103

RESUMO

Spiroterreusnoids A-F, six undescribed spiro-dioxolane-containing adducts bearing 3,5-dimethylorsellinic acid-based meroterpenoid and 2,3-butanediol moieties were isolated from the endophytic fungus Aspergillus terreus Thom from Tripterygium wilfordii Hook. f. (Celastraceae). The structures of these adducts were established by spectroscopy, single-crystal X-ray diffraction, and experimental electronic circular dichroism (ECD) measurements. Spiroterreusnoids A-F represent the first examples of adducts composed of 3,5-dimethylorsellinic acid-based meroterpenoids. It is noteworthy that spiroterreusnoids A-F possessing a spiro-dioxolane moiety exhibited potential abilities in inhibiting BACE1 (IC50 values ranging from 5.86 to 27.16 µM) and AchE (IC50 values ranging from 22.18 to 32.51 µM), while the other analogues without this fragment displayed no such activities. Taken together, spiroterreusnoids A-F represent the first multitargeted natural adducts that could inhibit BACE1 and AchE, and might provide a new template for the development of new anti-Alzheimer's disease drugs.


Assuntos
Acetilcolinesterase/metabolismo , Secretases da Proteína Precursora do Amiloide/antagonistas & inibidores , Ácido Aspártico Endopeptidases/antagonistas & inibidores , Dioxolanos/farmacologia , Inibidores Enzimáticos/farmacologia , Compostos de Espiro/farmacologia , Terpenos/farmacologia , Secretases da Proteína Precursora do Amiloide/metabolismo , Animais , Ácido Aspártico Endopeptidases/metabolismo , Aspergillus/química , Celastraceae/microbiologia , Dioxolanos/química , Dioxolanos/isolamento & purificação , Enguias , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Humanos , Compostos de Espiro/química , Compostos de Espiro/isolamento & purificação , Terpenos/química , Terpenos/isolamento & purificação
19.
Phytochemistry ; 164: 184-191, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31158603

RESUMO

Eleven highly oxygenated meroterpenoids, named terreustoxins A-K, along with five known analogues, were isolated from the Antarctic fungus Aspergillus terreus. The structures and absolute configurations of these undescribed compounds were characterized by NMR spectroscopy, single-crystal X-ray crystallography, and ECD experiments. Terreustoxins A-D are the first examples of meroterpenoids with two ortho-hydroxy groups at C-6 and C-7 in the terretonins family. Terreustoxin C and terretonin inhibited the proliferation of Con A-induced murine T cells at the concentration of 10 µM.


Assuntos
Aspergillus/química , Oxigênio/farmacologia , Terpenos/farmacologia , Animais , Aspergillus/metabolismo , Proliferação de Células/efeitos dos fármacos , Concanavalina A , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Camundongos , Modelos Moleculares , Conformação Molecular , Oxigênio/química , Oxigênio/metabolismo , Estereoisomerismo , Relação Estrutura-Atividade , Linfócitos T/efeitos dos fármacos , Terpenos/química , Terpenos/metabolismo
20.
Mar Drugs ; 17(6)2019 Jun 11.
Artigo em Inglês | MEDLINE | ID: mdl-31212583

RESUMO

Five new sesterterpenes, 14,15-dehydro-6-epi-ophiobolin K (1), 14,15-dehydro- ophiobolin K (2), 14,15-dehydro-6-epi-ophiobolin G (3), 14,15-dehydro-ophiobolin G (4) and 14,15-dehydro-(Z)-14-ophiobolin G (5), together with four known ophiobolins (6-9) were isolated from the marine fungus Aspergillus flocculosus derived from the seaweed Padina sp. collected in Vietnam. The five new ophiobolins were first isolated as ophiobolin derivatives consisting of a fully unsaturated side chain. Their structures were elucidated via spectroscopic methods including 1D, 2D NMR and HR-ESIMS. The absolute configurations were determined by the comparison of chemical shifts and optical rotation values with those of known ophiobolins. All compounds (1-9) were then evaluated for their cytotoxicity against six cancer cell lines, HCT-15, NUGC-3, NCI-H23, ACHN, PC-3 and MDA-MB-231. All the compounds showed potent cytotoxicity with GI50 values ranging from 0.14 to 2.01 µM.


Assuntos
Organismos Aquáticos/química , Aspergillus/química , Fungos/química , Sesterterpenos/química , Sesterterpenos/farmacologia , Linhagem Celular Tumoral , Humanos , Células PC-3 , Alga Marinha/microbiologia , Vietnã
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