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1.
Arch Microbiol ; 202(7): 1985-1996, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32476047

RESUMO

A soft coral-derived fungus Penicillium sp. among other isolates e high antibacterial, anti-yeast and cytotoxic activities. The fungus, Penicillium sp. MMA, isolated from Sarcphyton glaucoma, afforded nine diverse compounds (1-9). Their structures were identified by 1D and 2 D NMR and ESI-MS spectroscopic data as two alkaloids: veridicatol (1), aurantiomide C (2); one sesquiterpene, aspterric acid (3); two carboxylic acids, 3,4-dihydroxy-benzoic acid; (4) and linoleic acid (5); three steroids, ergosterol (6), ß-Sitosterol (7), ß-Sitosterol glucoside (8) along with the sphingolipid, cerebroside A (9). Biologically, the antimicrobial, antioxidant, in vitro cytotoxicity and antibiofilm activities were studied in comparison with the fungal extract. The in silico computational studies were implemented to predict drug and lead likeness properties for 1-4. The fungus was taxonomically characterized by morphological and molecular biology (18srRNA) approaches.


Assuntos
Anti-Infecciosos , Antineoplásicos , Bactérias/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Fungos/efeitos dos fármacos , Penicillium/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Oceano Índico , Estrutura Molecular , Penicillium/classificação , Penicillium/genética , Penicillium/metabolismo , RNA Ribossômico 18S/genética
2.
Mar Drugs ; 18(4)2020 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-32344725

RESUMO

Sponge-associated fungi are attractive targets for the isolation of bioactive natural products with different pharmaceutical purposes. In this investigation, 20 fungi were isolated from 10 different sponge specimens. One isolate, the fungus Penicillium citrinum strain WK-P9, showed activity against Bacillus subtilis JH642 when cultivated in malt extract medium. One new and three known citrinin derivatives were isolated from the extract of this fungus. The structures were elucidated by 1D and 2D NMR spectroscopy, as well as LC-HRMS. Their antibacterial activity against a set of common human pathogenic bacteria and fungi was tested. Compound 2 showed moderate activity against Mycobacterium smegmatis ATCC607 with a minimum inhibitory concentration (MIC) of 32 µg/mL. Compound 4 exhibited moderate growth inhibition against Bacillus subtilis JH642, B. megaterium DSM32, and M. smegmatis ATCC607 with MICs of 16, 16, and 32 µg/mL, respectively. Furthermore, weak activities of 64 µg/mL against B. subtilis DSM10 and S. aureus ATCC25923 were observed for compound 4.


Assuntos
Antibacterianos/isolamento & purificação , Citrinina/isolamento & purificação , Penicillium/química , Poríferos/microbiologia , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Bactérias/efeitos dos fármacos , Citrinina/química , Citrinina/farmacologia , Fungos/efeitos dos fármacos , Indonésia , Testes de Sensibilidade Microbiana , Penicillium/isolamento & purificação
3.
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
4.
J Environ Sci Health B ; 55(5): 470-476, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32009547

RESUMO

A central pillar of modern weed control is the discovery of new herbicides which are nontoxic to humans and the environment and which have low application dosage. The natural products found in plants and microorganisms are well suited in this context because they are generally nontoxic and have a wide variety of biological activities. In this work, Diaporthe phaseolorum (Dp), Penicillium simplicissimum (Ps) and Trichoderma spirale (Ts) (methanolic extracts) were evaluated as photosynthesis and plant growth inhibitors in Senna occidentalis and Ipomoea grandifolia. The most significant results were observed for Ts and Dp in S. occidentalis and I. grandifolia, respectively. Ts reduced PI(abs), ET0/CS0, PHI(E0) and PSI0 parameters by 64, 28, 40 and 38%, respectively, indicating a reduction on electron transport efficiency. Additionally, Ts decreased shoot length by 9%, affecting the plant growth. Dp reduced PI(abs), ET0/CS0 and PHI(E0) parameters by 50, 20, 26 and 22%, respectively, revealing the inhibition competency on PSII acceptor site. Furthermore, Dp decreased by 50% the shoot length on germination assay. Thus, the phytotoxic behaviors based on endophytic fungal extracts may serve as a valuable tool in the further development of a bioherbicide since natural products represent an interesting alternative to replace commercial herbicides.


Assuntos
Endófitos/química , Herbicidas/farmacologia , Ipomoea/efeitos dos fármacos , Fotossíntese/efeitos dos fármacos , Senna (Planta)/efeitos dos fármacos , Ascomicetos/química , Germinação/efeitos dos fármacos , Metanol , Penicillium/química , Reguladores de Crescimento de Planta/farmacologia , Raízes de Plantas/efeitos dos fármacos , Raízes de Plantas/crescimento & desenvolvimento , Caules de Planta/efeitos dos fármacos , Caules de Planta/crescimento & desenvolvimento , Trichoderma/química , Controle de Plantas Daninhas/métodos
5.
Chin J Nat Med ; 18(1): 75-80, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31955826

RESUMO

Purpurolides D-F (1-3), three new polyoxygenated bergamotanes bearing a 6/4/5/5 tetracyclic ring system, were isolated from the endophytic fungus Penicillium purpurogenum IMM 003. Their structures were unambiguously elucidated based on extensive spectroscopic data analyses, 13C NMR chemical shifts calculations coupled with the DP4+ probability method, and the calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 1-3 showed significant inhibitory activity against pancreatic lipase (PL). The result highlights that the presence of 3-hydroxylated decanoic acid moiety at C-14 is important for increasing the inhibition potency against PL.


Assuntos
Lipase/antagonistas & inibidores , Penicillium/química , Penicillium/isolamento & purificação , Sesquiterpenos/química , Linhagem Celular Tumoral , Humanos , Estrutura Molecular
6.
Fitoterapia ; 140: 104422, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31756377

RESUMO

Peniterester (1), a new tricyclic sesquiterpene, together with 6 known compounds (2-7) were isolated from the secondary metabolites of an artificial mutant Penicillium sp. T2-M20 which was obtained from the parental strain Penicillium sp. T2-8 via UV irradiation as well as nitrosoguanidine (NTG) induction. Peniterester was only produced by the mutant T2-M20 on the basis of LC-MS analysis. Meanwhile, the results of in vitro bioactivities screening indicated that peniterester owned obvious antibacterial activities against Bacillus subtilis, Escherichia coli and Staphylococcus aureus with MICs of 8.0, 8.0 and 4.0 µg/mL, respectively.


Assuntos
Antibacterianos/farmacologia , Penicillium/química , Sesquiterpenos/farmacologia , Antibacterianos/isolamento & purificação , Bacillus subtilis/efeitos dos fármacos , Linhagem Celular Tumoral , China , Escherichia coli/efeitos dos fármacos , Gastrodia/microbiologia , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Rizoma/microbiologia , Metabolismo Secundário , Sesquiterpenos/isolamento & purificação , Staphylococcus aureus/efeitos dos fármacos
7.
Nat Prod Res ; 34(8): 1118-1123, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30663353

RESUMO

Four new diketopiperazine alkaloids, citriperazines A-D were isolated from algae-derived Penicillium sp. KMM 4672. The structures of compounds 1-4 were determined using spectroscopic methods. The absolute configurations of compounds 1 and 4 were established by comparison of calculated and experimental ECD spectra. The cytotoxicity of compounds 1-4 against several human prostate cell lines was evaluated.


Assuntos
Dicetopiperazinas/isolamento & purificação , Penicillium/química , Alcaloides/química , Alcaloides/isolamento & purificação , Linhagem Celular Tumoral , Citotoxinas/química , Citotoxinas/isolamento & purificação , Citotoxinas/farmacologia , Dicetopiperazinas/química , Humanos , Conformação Molecular , Estrutura Molecular , Análise Espectral
8.
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
9.
Nat Prod Res ; 34(3): 378-384, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30623670

RESUMO

A new prenylated indole alkaloid, named paraherquamide J (1), together with four known compounds (2-5), were isolated from the mangrove rhizosphere soil-derived fungus Penicillium janthinellum HK1-6. The planar structure and relative configuration of 1 were determined by detailed analysis of the spectroscopic data especially the NOESY spectrum. The absolute configuration of 1 was determined by ECD spectra. Compound 2 was first isolated as a natural product and named as paraherquamide K. All isolated metabolites were evaluated for their antibacterial, topoisomerase I (topo I) inhibitory activities and lethality towards brine shrimp Artemia salina.


Assuntos
Antibacterianos/isolamento & purificação , Indolizinas/isolamento & purificação , Penicillium/química , Compostos de Espiro/isolamento & purificação , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Artemia/efeitos dos fármacos , Alcaloides Indólicos/química , Alcaloides Indólicos/isolamento & purificação , Alcaloides Indólicos/farmacologia , Indolizinas/toxicidade , Estrutura Molecular , Prenilação , Rizosfera , Compostos de Espiro/toxicidade , Inibidores da Topoisomerase I/química , Inibidores da Topoisomerase I/isolamento & purificação , Inibidores da Topoisomerase I/farmacologia
10.
Nat Prod Res ; 34(7): 1032-1036, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30584771

RESUMO

In continuation of the search for new compounds from the terrestrial fungus Penicillium purpurogenum MM, (3R,4S)-isostreptenol III (1), a further new natural compound is reported. The chemical structure of 1 was confirmed by extensive 1D and 2D NMR and ESI HR mass measurements, and by comparison with literature data. The absolute configuration was determined by ab initio calculations of ECD, ORD, and NMR data. The antimicrobial and cytotoxic activities of the crude extract and 1 were reported using a set of microorganisms and by the brine shrimp assay, respectively.


Assuntos
Anti-Infecciosos/isolamento & purificação , Antineoplásicos/isolamento & purificação , Penicillium/química , Antibacterianos , Anti-Infecciosos/farmacologia , Antineoplásicos/química , Humanos , Espectroscopia de Ressonância Magnética/métodos , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray/métodos , Talaromyces
11.
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
12.
J Agric Food Chem ; 67(51): 14102-14109, 2019 Dec 26.
Artigo em Inglês | MEDLINE | ID: mdl-31790231

RESUMO

Herbicidal activity-guided isolation from the fermentation extract of Penicillium viridicatum had obtained two herbicidal series of polyketides (1-7) and diketopiperazine derivatives (8-11), especially including three novel polyketides (1-3). The structures and absolute configurations of new polyketides 1-3 were elucidated by extensive spectroscopic analyses, as well as comparisons between measured and calculated ECD spectra. Novel polyketides 1-3 and known 4, all bearing the heptaketide skeleton with a trans-fused decalin ring of 8-CH3 substitution, could significantly inhibit the radicle growth of Echinochloa crusgalli seedlings with a dose-dependent relationship. Especially at the concentration of 10 µg/mL, 1-4 exhibited the inhibition rates with 81.5% ± 2.0, 76.4% ± 0.8, 79.6% ± 1.1, and 80.0 ± 1.8%, respectively, even better than the commonly used synthetic herbicide of acetochlor with 76.1 ± 1.4%. Further greenhouse bioassay revealed that 4 showed pre-emergence herbicidal activity against E. crusgalli with the fresh-weight inhibition rate of 74.1% at a dosage of 400 g ai/ha, also better than acetochlor, while the other isolated metabolites (5-11) exhibited moderate herbicidal activities. The structure-activity differences of isolated polyketides indicated that the heptaketide skeleton, characterized by a trans-fused decalin ring with 8-CH3 substitution, should be the key factor of their herbicidal activities, which could give new insights for the bioherbicide developments.


Assuntos
Dicetopiperazinas/farmacologia , Herbicidas/farmacologia , Penicillium/química , Policetídeos/farmacologia , Dicetopiperazinas/metabolismo , Echinochloa/efeitos dos fármacos , Echinochloa/crescimento & desenvolvimento , Herbicidas/metabolismo , Estrutura Molecular , Penicillium/metabolismo , Policetídeos/metabolismo
13.
Molecules ; 24(24)2019 Dec 17.
Artigo em Inglês | MEDLINE | ID: mdl-31861067

RESUMO

In the search for new microbial antibacterial secondary metabolites, two new compounds (1 and 2) were isolated from culture broths of Penicillium spathulatum Em19. Structure determination by nuclear magnetic resonance and mass spectrometry identified the compounds as 6,7-dihydroxy-5,10-dihydropyrrolo[1,2-b]isoquinoline-3-carboxylic acid (1, spathullin A) and 5,10-dihydropyrrolo[1,2-b]isoquinoline-6,7-diol (2, spathullin B). The two compounds displayed activity against both Gram-negative and -positive bacteria, including Escherichia coli, Acinetobacter baumannii, Enterobacter cloacae, Klebsiella pneumonia, Pseudomonas aeruginosa, and Staphylococcus aureus. Compound 2 was more potent than 1 against all tested pathogens, with minimal inhibitory concentrations down to 1 µg/mL (5 µM) against S. aureus, but 2 was also more cytotoxic than 1 (50% inhibitory concentrations 112 and 11 µM for compounds 1 and 2, respectively, towards Huh7 cells). Based on stable isotope labelling experiments and a literature comparison, the biosynthesis of 1 was suggested to proceed from cysteine, tyrosine and methionine via a non-ribosomal peptides synthase like enzyme complex, whereas compound 2 was formed spontaneously from 1 by decarboxylation. Compound 1 was also easily oxidized to the 1,2-benzoquinone 3. Due to the instability of compound 1 and the toxicity of 2, the compounds are of low interest as possible future antibacterial drugs.


Assuntos
Alcaloides/química , Alcaloides/farmacologia , Antibacterianos/química , Antibacterianos/farmacologia , Isoquinolinas/química , Isoquinolinas/farmacologia , Penicillium , Alcaloides/isolamento & purificação , Antibacterianos/isolamento & purificação , Vias Biossintéticas , Farmacorresistência Bacteriana , Isoquinolinas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Penicillium/química , Penicillium/metabolismo
14.
Mar Drugs ; 17(11)2019 Nov 18.
Artigo em Inglês | MEDLINE | ID: mdl-31752168

RESUMO

Six new carotane sesquiterpenoids piltunines A-F (1-6) together with known compounds (7-9) were isolated from the marine-derived fungus Penicillium piltunense KMM 4668. Their structures were established using spectroscopic methods. The absolute configurations of 1-7 were determined based on circular dichroism (CD) and nuclear Overhauser spectroscopy (NOESY) data as well as biogenetic considerations. The cytotoxic activity of some of the isolated compounds and their effects on regulation of reactive oxygen species (ROS) and nitric oxide (NO) production in lipopolysaccharide-stimulated macrophages were examined.


Assuntos
Antineoplásicos/farmacologia , Macrófagos/efeitos dos fármacos , Penicillium/química , Sesquiterpenos/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Células Cultivadas , Dicroísmo Circular , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Macrófagos/metabolismo , Camundongos , Camundongos Endogâmicos BALB C , Óxido Nítrico/metabolismo , Espécies Reativas de Oxigênio/metabolismo , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação
15.
Phys Chem Chem Phys ; 21(46): 25658-25668, 2019 Nov 27.
Artigo em Inglês | MEDLINE | ID: mdl-31725143

RESUMO

PrhA from Penicillium brasilianum and AusE from Aspergillus nidulans are nonheme Fe(ii)/α-ketoglutarate-dependent oxygenases, which are involved in the fungal meroterpenoid biosynthetic pathways. Both enzymes use preaustinoid A1 as a common substrate to form divergent products through dynamic skeletal rearrangement. Importantly, structure-guided mutagenesis results in the successful interconversion of AusE and PrhA functions, for example, the PrhA(V150L/A232S) double mutant carried out the same catalysis as AusE. Here, on the basis of the crystal structure of the PrhA (V150L/A232S) double mutant in complex with Fe(ii), αKG and the substrate preaustinoid A1, computational models were constructed, and combined quantum mechanics/molecular mechanics (QM/MM) calculations were performed to illuminate the reaction mechanism at the atomistic level. According to our calculation results, the whole reaction occurs on the quintet state surface. All three steps, including desaturation, ring rearrangement and hydroxylation, require three hydrogen abstractions by FeIV[double bond, length as m-dash]O to trigger the reaction. Owing to the relative position of FeIV[double bond, length as m-dash]O to the hydrogen atoms in the substrate to be extracted, the three H-abstractions correspond to different energy barriers, which are 17.9, 23.6 and 21.8 kcal mol-1, respectively. For the ring rearrangement, as soon as the H5 is extracted, the skeletal rearrangement is very easy. However, in the hydroxylation of intermediate preaustinoid A3, the final O-rebound corresponds to a high barrier, which is mainly caused by the long distance between the Fe-OH and -CH2 radical. It is the relative orientation of the substrate to the highly reactive FeIV[double bond, length as m-dash]O that controls the catalytic chemistry of these enzymes. The reaction barriers are sensitive to the geometry of FeIV[double bond, length as m-dash]OHx (Hx is the hydrogen atom to be extracted). These results may provide useful information for understanding the mechanisms of AusE and PrhA as well as other nonheme Fe(ii)/α-ketoglutarate-dependent oxygenases.


Assuntos
Aspergillus nidulans/química , Vias Biossintéticas , Mutação , Oxigenases/metabolismo , Penicillium/química , Teoria Quântica , Terpenos/metabolismo , Aspergillus nidulans/metabolismo , Biocatálise , Conformação Molecular , Oxigenases/química , Penicillium/metabolismo , Terpenos/química
16.
Fitoterapia ; 139: 104400, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31669962

RESUMO

Two novel epimer pairs of acetaminophen derivatives penicilquei A-D (1-4) were isolated from Penicillium herquei JX4. Their structures were elucidated using comprehensive spectroscopic methods. The absolute configurations of penicilquei A-D (1-4) were determined by modifified Mosher's method, and comparing their experimental and calculated electronic circular dichroism (ECD) spectra. Penicilquei A-D (1-4) are the first example of acetaminophen derivatives featuring an unprecedented carbon skeleton. The inhibitory activities of all compounds against nine phytopathogenic fungi and α-glucosidase were evaluated. Penicilquei A-D (1-4) showed strong inhibitory activities against at least eight phytopathogenic fungus.


Assuntos
Acetaminofen/farmacologia , Fungicidas Industriais/farmacologia , Penicillium/química , Acetaminofen/química , China , Fungicidas Industriais/química , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Estrutura Molecular , Rhizophoraceae/microbiologia
17.
Molecules ; 24(21)2019 Oct 24.
Artigo em Inglês | MEDLINE | ID: mdl-31652901

RESUMO

Marine microorganisms are an invaluable source of novel active secondary metabolites possessing various biological activities. In this study, the extraction and isolation of the marine sediment Penicillium species collected in Vietnam yielded ten secondary metabolites, including sporogen AO-1 (1), 3-indolecarbaldehyde (2), 2-[(5-methyl-1,4-dioxan-2-yl)methoxy]ethanol (3), 2-[(2R-hydroxypropanoyl)amino]benzamide (4), 4-hydroxybenzandehyde (5), chrysogine (6), 3-acetyl-4-hydroxycinnoline (7), acid 1H-indole-3-acetic (8), cyclo (Tyr-Trp) (9), and 2',3'-dihydrosorbicillin (10). Their structures were identified by the analysis of 1D and 2D NMR data. Among the isolated compounds, 2-[(5-methyl-1,4-dioxan-2-yl)methoxy]ethanol (3) showed a strong inhibitory effect against Enterococcus faecalis with a minimum inhibitory concentration value of 32 µg/mL. Both 2-[(2R-hydroxypropanoyl)amino]benzamide (4) and 4-hydroxybenzandehyde (5) selectively inhibited E. coli with minimum inhibitory concentration values of 16 and 8 µg/mL, respectively. 2',3'-Dihydrosorbicillin (10) potentially inhibited α-glucosidase activity at a concentration of 2.0 mM (66.31%).


Assuntos
Antibacterianos , Organismos Aquáticos , Enterococcus faecalis/crescimento & desenvolvimento , Penicillium , Antibacterianos/química , Antibacterianos/metabolismo , Antibacterianos/farmacologia , Organismos Aquáticos/química , Organismos Aquáticos/metabolismo , Estrutura Molecular , Penicillium/química , Penicillium/metabolismo , Vietnã
18.
J Basic Microbiol ; 59(12): 1238-1247, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31613018

RESUMO

Penicillium griseoroseum lectin was 80-fold purified by successive DEAE Sepharose anion exchange and Sephadex G-100 gel permeation chromatography. P. griseoroseum lectin exhibited haemagglutination activity towards protease-treated rabbit erythrocytes. It showed specificity towards various carbohydrates such as d-mannose, N-acetyl-d-glucosamine, mucins, and so forth. P. griseoroseum lectin was found as a glycoprotein with glycan content of 4.33%. Purified P. griseoroseum lectin is homodimeric having a molecular mass of 57 kDa with subunit molecular mass of 28.6 kDa. Haemagglutination activity of purified P. griseoroseum lectin was completely stable from 25°C to 35°C at a pH range of 6-7.5. Lectin activity was not influenced by divalent metal ions and denaturants. P. griseoroseum lectin manifested mitogenicity towards mice splenocytes and activity reached a peak at 75 µg/ml of lectin concentration. P. griseoroseum lectin in microgram concentrations stimulated proliferation of mice splenocytes. Thus, P. griseoroseum lectin exhibits potential mitogenicity, which can be exploited for further biomedical applications.


Assuntos
Lectinas/química , Lectinas/isolamento & purificação , Mitógenos/química , Mitógenos/isolamento & purificação , Penicillium/química , Animais , Carboidratos/química , Cátions/metabolismo , Proliferação de Células/efeitos dos fármacos , Quelantes , Glicoproteínas/química , Hemaglutinação , Concentração de Íons de Hidrogênio , Lectinas/farmacologia , Masculino , Camundongos , Mitógenos/farmacologia , Peso Molecular , Multimerização Proteica , Estabilidade Proteica , Temperatura
19.
Proc Natl Acad Sci U S A ; 116(44): 22353-22358, 2019 10 29.
Artigo em Inglês | MEDLINE | ID: mdl-31611414

RESUMO

An Australian estuarine isolate of Penicillium sp. MST-MF667 yielded 3 tetrapeptides named the bilaids with an unusual alternating LDLD chirality. Given their resemblance to known short peptide opioid agonists, we elucidated that they were weak (K i low micromolar) µ-opioid agonists, which led to the design of bilorphin, a potent and selective µ-opioid receptor (MOPr) agonist (K i 1.1 nM). In sharp contrast to all-natural product opioid peptides that efficaciously recruit ß-arrestin, bilorphin is G protein biased, weakly phosphorylating the MOPr and marginally recruiting ß-arrestin, with no receptor internalization. Importantly, bilorphin exhibits a similar G protein bias to oliceridine, a small nonpeptide with improved overdose safety. Molecular dynamics simulations of bilorphin and the strongly arrestin-biased endomorphin-2 with the MOPr indicate distinct receptor interactions and receptor conformations that could underlie their large differences in bias. Whereas bilorphin is systemically inactive, a glycosylated analog, bilactorphin, is orally active with similar in vivo potency to morphine. Bilorphin is both a unique molecular tool that enhances understanding of MOPr biased signaling and a promising lead in the development of next generation analgesics.


Assuntos
Analgésicos Opioides/farmacologia , Proteínas Fúngicas/farmacologia , Oligopeptídeos/farmacologia , Penicillium/química , Receptores Opioides mu/agonistas , Analgésicos Opioides/química , Animais , Sítios de Ligação , Linhagem Celular Tumoral , Proteínas Fúngicas/química , Células HEK293 , Humanos , Camundongos , Simulação de Acoplamento Molecular , Oligopeptídeos/química , Ligação Proteica , Receptores Opioides mu/química , Receptores Opioides mu/metabolismo
20.
Mar Drugs ; 17(9)2019 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-31480589

RESUMO

Identification and analysis of the whole genome of the marine-derived fungus Penicillium brasilianum HBU-136 revealed the presence of an interesting biosynthetic gene cluster (BGC) for non-ribosomal peptide synthetases (NRPS), highly homologous to the BGCs of indole-diketopiperazine derivatives. With the aid of genomic analysis, eight indole-diketopiperazines (1-8), including three new compounds, spirotryprostatin G (1), and cyclotryprostatins F and G (2 and 3), were obtained by large-scale cultivation of the fungal strain HBU-136 using rice medium with 1.0% MgCl2. The absolute configurations of 1-3 were determined by comparison of their experimental electronic circular dichroism (ECD) with calculated ECD spectra. Selective cytotoxicities were observed for compounds 1 and 4 against HL-60 cell line with the IC50 values of 6.0 and 7.9 µM, respectively, whereas 2, 3, and 5 against MCF-7 cell line with the IC50 values of 7.6, 10.8, and 5.1 µM, respectively.


Assuntos
Organismos Aquáticos/química , Dicetopiperazinas/química , Fungos/química , Fungos/genética , Indóis/química , Penicillium/química , Penicillium/genética , Organismos Aquáticos/genética , Linhagem Celular Tumoral , Dicroísmo Circular , Genoma/genética , Genômica , Células HL-60 , Humanos , Células MCF-7 , Família Multigênica/genética , Peptídeo Sintases/genética
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