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1.
Molecules ; 29(20)2024 Oct 13.
Artigo em Inglês | MEDLINE | ID: mdl-39459217

RESUMO

Taking the endophytic fungus UJ3-2, isolated from Urtica fissa, as the experimental material, this study aimed to explore the composition of its metabolites and the underlying mechanisms by which it inhibits Staphylococcus aureus. Initially, the MIC, MBC, inhibitory curves, biofilm growth, and extracellular nucleic acids and proteins of S. aureus in response to the metabolites were measured. Secondly, PI staining and SEM were used to evaluate the impact of the metabolites on the integrity of the cell wall and overall morphology of S. aureus. Additionally, UPLC-MS was employed to analyze the composition of the secondary metabolites. The UJ3-2 strain was identified as Xylaria grammica based on ITS sequencing and designated as Xylaria grammica UJ3-2. Our results revealed that the metabolites of UJ3-2 exhibited excellent in vitro antibacterial activity against S. aureus, with both MIC and MBC values of 3.125 mg/mL. The inhibitory curve confirmed that 1 MIC of UJ3-2 metabolites could completely inhibit the growth of S. aureus within 24 h. With increasing concentrations of UJ3-2 metabolites, the growth of S. aureus biofilms was significantly suppressed, and obvious leakage of nucleic acids and proteins was observed. PI fluorescence staining indicated that various concentrations of UJ3-2 metabolites disrupted the integrity of the S. aureus cell membrane. SEM observation revealed that the treated S. aureus surfaces became rough, and the bacteria shrank and adhered to each other, showing a dose-dependent effect. UPLC-MS analysis suggested that the main components of the fermented metabolites were 6-oxocineole (17.92%), (S)-2-acetolactate (9.91%), 3-methyl-cis,cis-muconate (4.36%), and 8-oxogeranial (3.17%). This study demonstrates that the endophytic fungus UJ3-2 exhibits remarkable in vitro antibacterial effects against S. aureus, primarily by enhancing the permeability of the S. aureus cell membrane, causing the leakage of its intracellular contents, and altering the bacterial surface morphology to inhibit the pathogen. The endophytic fungus UJ3-2 has a good antibacterial effect on S. aureus, which gives it certain application prospects in the screening and industrial production of new and efficient natural antibacterial active substances.


Assuntos
Antibacterianos , Biofilmes , Testes de Sensibilidade Microbiana , Staphylococcus aureus , Staphylococcus aureus/efeitos dos fármacos , Antibacterianos/farmacologia , Antibacterianos/química , Biofilmes/efeitos dos fármacos , Biofilmes/crescimento & desenvolvimento , Endófitos/química , Endófitos/metabolismo , Xylariales/química , Xylariales/metabolismo
2.
Mar Drugs ; 22(9)2024 Sep 05.
Artigo em Inglês | MEDLINE | ID: mdl-39330288

RESUMO

Twelve compounds, including four undescribed cytochalasins, xylariachalasins A-D (1-4), four undescribed polyketides (5-8), and four known cytochalasins (9-12), were isolated from the mangrove endophytic fungus Xylaria arbuscula QYF. Their structures and absolute configurations were established by extensive spectroscopic analyses (1D and 2D NMR, HRESIMS), electronic circular dichroism (ECD) calculations, 13C NMR calculation and DP4+ analysis, single-crystal X-ray diffraction, and the modified Mosher ester method. Compounds 1 and 2 are rare cytochalasin hydroperoxides. In bioactivity assays, Compound 2 exhibited moderate antimicrobial activities against Staphylococcus aureus and Candida albicans with MIC values of 12.5 µM for both Compound 10 exhibited significant cytotoxic activity against MDA-MB-435 with an IC50 value of 3.61 ± 1.60 µM.


Assuntos
Candida albicans , Citocalasinas , Testes de Sensibilidade Microbiana , Policetídeos , Staphylococcus aureus , Xylariales , Policetídeos/farmacologia , Policetídeos/química , Policetídeos/isolamento & purificação , Citocalasinas/farmacologia , Citocalasinas/química , Citocalasinas/isolamento & purificação , Xylariales/química , Staphylococcus aureus/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Linhagem Celular Tumoral , Humanos , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Estrutura Molecular , Endófitos/química , Cristalografia por Raios X
3.
J Nat Prod ; 87(8): 2095-2100, 2024 Aug 23.
Artigo em Inglês | MEDLINE | ID: mdl-39039966

RESUMO

Wheldone is a fungal metabolite isolated from the coculture of Aspergillus fischeri and Xylaria flabelliformis, displaying cytotoxic activity against breast, melanoma, and ovarian cancer cell lines. Initially, its structure was characterized as an unusual 5-methyl-bicyclo[5.4.0]undeca-3,5-diene scaffold with a 2-hydroxy-1-propanone side chain and a 3-(2-(1-hydroxyethyl)-2-methyl-2,5-dihydrofuran-3-yl)acrylic acid moiety. Upon further examination, minor inconsistencies in the data suggested the need for the structure to be revisited. Thus, the structure of wheldone has been revised using an orthogonal experimental-computational approach, which combines 1,1-HD-ADEQUATE NMR experiments, DFT-GIAO chemical shift calculations, and single-crystal X-ray diffraction (SCXRD) analysis of a semisynthetic p-bromobenzylamide derivative, formed via a Steglich-type reaction. The summation of these data now permits the unequivocal assignment of both the structure and absolute configuration of the natural product.


Assuntos
Espectroscopia de Ressonância Magnética , Cristalografia por Raios X/métodos , Estrutura Molecular , Espectroscopia de Ressonância Magnética/métodos , Aspergillus/química , Xylariales/química , Humanos
4.
J Food Drug Anal ; 32(2): 155-167, 2024 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-38934694

RESUMO

In this study, a marine medicinal brown alga Sargassum cristaefolium-derived fungal strain Xylaria acuta SC1019 was isolated and identified. Column chromatography of the extracts from liquid- and solid-fermented products of the fungal strain was carried out, and led to the isolation of twenty-one compounds. Their structures were characterized by spectroscopic analysis, and the absolute configurations were further established by single X-ray diffraction analysis or modified Mosher's method as nine previously undescribed compounds, namely xylarilactones A-C (1-3), ent-gedebic acid 8-O-α-D-glucopyranoside (4), 5R-hydroxylmethylmellein 11-O-α-D-glucopyranoside (5), ent-hymatoxin E 16-O-α-D-mannopyranoside (6), 19,20-epoxycytochalasin S (7), 19,20-epoxycytochalasin T (8), and (2R)-butylitaconic acid (9), along with twelve known compounds 10-21. All the isolates were subjected to anti-inflammatory and anti-angiogenic assays. Compounds 1, 5, 7, 10, and 17 showed moderate nitric oxide production inhibitory activities in lipopolysaccharide-activated BV-2 microglial cells with IC50 values of 19.55 ± 0.35, 16.10 ± 0.57, 15.20 ± 0.87, 11.76 ± 0.49, and 11.30 ± 0.32 µM, respectively, as compared to curcumin (IC50 = 2.69 ± 0.34 µM) without any significant cytotoxicity. Compounds 7, 8, and 21 displayed potent anti-angiogenic activities by suppressing the growth of human endothelial progenitor cells with IC50 values of 0.44 ± 0.01, 0.47 ± 0.03, and 0.53 ± 0.01 µM, respectively, as compared to sorafenib (IC50 = 5.50 ± 1.50 µM).


Assuntos
Xylariales , Humanos , Animais , Xylariales/química , Camundongos , Estrutura Molecular , Phaeophyceae/química , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular
5.
Z Naturforsch C J Biosci ; 79(11-12): 371-376, 2024 Nov 26.
Artigo em Inglês | MEDLINE | ID: mdl-38934215

RESUMO

Chemical investigation of the fungal endophyte Xylaria sp. isolated from leaves of Moringa oleifera, collected in Cameroon, resulted in the previously undescribed 10-membered macrolide, and two known natural products. The structures of the xylatolides A and B were unambiguously identified by their mass spectra and by extensive 1D and 2D NMR spectroscopic analysis, featuring a 10-membered lactone core structure with oxygenated substituents and an unsubstituted 10-alkyl chain presenting seven carbon atoms. Compounds were screened for their cytotoxic potential against the human HepG2 hepatocellular carcinoma cells and HCT-116 cells (human colon carcinoma cell line). Moreover, the isolated compounds were also assayed against a small panel of sensitive strains including the bacterial species Escherichia coli, Staphylococcus aureus, and Mycobacterium tuberculosis as well as against the fungal species Candida albicans. However, no significant activities were found.


Assuntos
Macrolídeos , Xylariales , Humanos , Macrolídeos/química , Macrolídeos/farmacologia , Macrolídeos/isolamento & purificação , Células Hep G2 , Xylariales/química , Células HCT116 , Testes de Sensibilidade Microbiana , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Candida albicans/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Endófitos/química , Moringa oleifera/química , Folhas de Planta/microbiologia , Folhas de Planta/química , Staphylococcus aureus/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Mycobacterium tuberculosis/efeitos dos fármacos
6.
Chem Biodivers ; 21(7): e202400900, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38713316

RESUMO

A new compound xylarkarynone A (1), a first reported natural product compound xylarkarynone B (2) and eight known compounds (3-10) were isolated from Xylaria sp. HHY-2. Their structures were elucidated by spectroscopic methods, DP4+ probability analyses and electronic circular dichroism (ECD) calculations. The bioactivities of isolated compounds were assayed. Compound 1 exhibited obvious activity against A549 cells with an IC50 value of 6.12±0.28 µM. Additionally, compound 1 showed moderate antifungal activities against Plectosphaerella cucumerina and Aspergillus niger with minimum inhibitory concentrations (MICs) of both 16 µg/mL, which was at the same grade with positive control nystatin. Most compounds exhibited varying degrees of inhibitory activity against P. cucumerina, indicating that Xylaria sp. has potential as inhibitors against P. cucumerina.


Assuntos
Antifúngicos , Aspergillus niger , Testes de Sensibilidade Microbiana , Sesquiterpenos , Xylariales , Humanos , Xylariales/química , Antifúngicos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Aspergillus niger/efeitos dos fármacos , Células A549 , Ensaios de Seleção de Medicamentos Antitumorais , Ascomicetos/química , Estrutura Molecular , Conformação Molecular , Relação Estrutura-Atividade , Relação Dose-Resposta a Droga
7.
Molecules ; 29(8)2024 Apr 11.
Artigo em Inglês | MEDLINE | ID: mdl-38675548

RESUMO

The fungus Xylaria sp. Z184, harvested from the leaves of Fallopia convolvulus (L.) Á. Löve, has been isolated for the first time. Chemical investigation on the methanol extract of the culture broth of the titles strain led to the discovery of three new pyranone derivatives, called fallopiaxylaresters A-C (1-3), and a new bisabolane-type sesquiterpenoid, named fallopiaxylarol A (4), along with the first complete set of spectroscopic data for the previously reported pestalotiopyrone M (5). Known pyranone derivatives (6-11), sesquiterpenoids (12-14), isocoumarin derivatives (15-17), and an aromatic allenic ether (18) were also co-isolated in this study. All new structures were elucidated by the interpretation of HRESIMS, 1D, 2D NMR spectroscopy, and quantum chemical computation approach. The in vitro antimicrobial, anti-inflammatory, and α-glucosidase-inhibitory activities of the selected compounds and the crude extract were evaluated. The extract was shown to inhibit nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells, with an inhibition rate of 77.28 ± 0.82% at a concentration of 50 µg/mL. The compounds 5, 7, and 8 displayed weak antibacterial activity against Staphylococcus areus subsp. aureus at a concentration of 100 µM.


Assuntos
Sesquiterpenos , Xylariales , Camundongos , Animais , Células RAW 264.7 , Xylariales/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos/isolamento & purificação , Óxido Nítrico/biossíntese , Óxido Nítrico/metabolismo , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Estrutura Molecular , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Lipopolissacarídeos , Testes de Sensibilidade Microbiana , Macrófagos/efeitos dos fármacos , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação
8.
Bioorg Chem ; 147: 107329, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38608410

RESUMO

By co-culturing two endophytic fungi (Chaetomium virescens and Xylaria grammica) collected from the medicinal and edible plant Smilax glabra Roxb. and analyzing them with MolNetEnhancer module on GNPS platform, seven undescribed chromone-derived polyketides (chaetoxylariones A-G), including three pairs of enantiomer ones (2a/2b, 4a/4b and 6a/6b) and four optical pure ones (1, 3, 5 and 7), as well as five known structural analogues (8-12), were obtained. The structures of these new compounds were characterized by NMR spectroscopy, single-crystal X-ray diffraction, 13C NMR calculation and DP4+ probability analyses, as well as the comparison of the experimental electronic circular dichroism (ECD) data. Structurally, compound 1 featured an unprecedented chromone-derived sulfonamide tailored by two isoleucine-derived δ-hydroxy-3-methylpentenoic acids via the acylamide and NO bonds, respectively; compound 2 represented the first example of enantiomeric chromone derivative bearing a unique spiro-[3.3]alkane ring system; compound 3 featured a decane alkyl side chain that formed an undescribed five-membered lactone ring between C-7' and C-10'; compound 4 contained an unexpected highly oxidized five-membered carbocyclic system featuring rare adjacent keto groups; compound 7 featured a rare methylsulfonyl moiety. In addition, compound 10 showed a significant inhibition towards SW620/AD300 cells with an IC50 value of PTX significantly decreased from 4.09 µM to 120 nM, and a further study uncovered that compound 10 could obviously reverse the MDR of SW620/AD300 cells.


Assuntos
Antineoplásicos , Chaetomium , Cromonas , Ensaios de Seleção de Medicamentos Antitumorais , Policetídeos , Xylariales , Cromonas/química , Cromonas/farmacologia , Cromonas/isolamento & purificação , Policetídeos/química , Policetídeos/farmacologia , Policetídeos/isolamento & purificação , Estrutura Molecular , Xylariales/química , Chaetomium/química , Humanos , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Relação Estrutura-Atividade , Relação Dose-Resposta a Droga , Linhagem Celular Tumoral , Técnicas de Cocultura , Proliferação de Células/efeitos dos fármacos
9.
Phytochemistry ; 222: 114103, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38636686

RESUMO

Eight new cytochalasans rosellichalasins A-H (1-8), as well as two new shunt metabolites rosellinins A (9) and B (10) before intramolecular Diels-Alder cycloaddition reaction in cytochalasan biosynthesis, along with nine known cytochalsans (11-19) were isolated from the endophytic fungus Rosellinia sp. Glinf021, which was derived from the medicinal plant Glycyrrhiza inflata. Their structures were characterized by extensive analysis of 1D and 2D NMR as well as HRESIMS spectra and quantum chemical ECD calculations. The cytotoxic activities of these compounds were evaluated against four human cancer cell lines including HCT116, MDA-MB-231, BGC823, and PANC-1 with IC50 values ranging from 0.5 to 58.2 µM.


Assuntos
Antineoplásicos , Citocalasinas , Ensaios de Seleção de Medicamentos Antitumorais , Xylariales , Humanos , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Citocalasinas/química , Citocalasinas/farmacologia , Citocalasinas/isolamento & purificação , Relação Dose-Resposta a Droga , Endófitos/química , Estrutura Molecular , Relação Estrutura-Atividade , Xylariales/química , Xylariales/classificação
10.
Fitoterapia ; 175: 105930, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38554885

RESUMO

Two new quinoline alkaloids with an α, ß-unsaturated amide side chain, xylarinines A and B (1 and 2), were isolated from the ethyl acetate extracts of Xylaria longipes solid fermentation. The structures of these were primarily determined though NMR and HRESIMS data analysis. The absolute configuration of compound 1 was assigned using experimental and calculated ECD data. The neuroprotective effects of compounds 1 and 2 against glutamate-induced damage in PC12 cells were evaluated in vitro bioassay. The results demonstrated that both compounds significantly improved cell viability, inhibited apoptosis, decreased malondialdehyde (MDA) levels, increased superoxide dismutase (SOD) and glutathione (GSH) levels, and reduced intracellular reactive oxygen species (ROS) accumulation. These findings suggested that these mechanisms contribute to the neuroprotective effects of the compounds.


Assuntos
Alcaloides , Apoptose , Fármacos Neuroprotetores , Quinolinas , Espécies Reativas de Oxigênio , Xylariales , Células PC12 , Fármacos Neuroprotetores/farmacologia , Fármacos Neuroprotetores/isolamento & purificação , Animais , Ratos , Quinolinas/farmacologia , Quinolinas/isolamento & purificação , Estrutura Molecular , Alcaloides/farmacologia , Alcaloides/isolamento & purificação , Espécies Reativas de Oxigênio/metabolismo , Xylariales/química , Apoptose/efeitos dos fármacos , Superóxido Dismutase/metabolismo , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Malondialdeído/metabolismo , Glutationa/metabolismo , Sobrevivência Celular/efeitos dos fármacos , China , Ácido Glutâmico
11.
Int J Mol Sci ; 25(6)2024 Mar 07.
Artigo em Inglês | MEDLINE | ID: mdl-38542068

RESUMO

The genus Neopestalotiopsis consists of obligate parasites that cause ring spot, scab, and leaf blight diseases in higher plant species. We assembled the three complete mitogenomes for the guava fruit ring spot pathogen, Neopestalotiopsis cubana. The mitogenomes are circular, with sizes of 38,666 bp, 33,846 bp, and 32,593 bp. The comparative analyses with Pestalotiopsis fici showed that N. cubana differs greatly from it in the length of the mitogenomes and the number of introns. Moreover, they showed significant differences in the gene content and tRNAs. The two genera showed little difference in gene skewness and codon preference for core protein-coding genes (PCGs). We compared gene sequencing in the mitogenomes of the order Xylariales and found large-scale gene rearrangement events, such as gene translocations and the duplication of tRNAs. N. cubana shows a unique evolutionary position in the phylum Ascomycota constructed in phylogenetic analyses. We also found a more concentrated distribution of evolutionary pressures on the PCGs of Neopestalotiopsis in the phylum Ascomycota and that they are under little selective pressure compared to other species and are subjected to purifying selection. This study explores the evolutionary dynamics of the mitogenomes of Neopestalotiopsis and provides important support for genetic and taxonomic studies.


Assuntos
Genoma Mitocondrial , Xylariales , Filogenia , Xylariales/genética , RNA de Transferência/genética , Íntrons
12.
J Asian Nat Prod Res ; 26(2): 214-227, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38353486

RESUMO

Five new sesquiterpenoids, including a campherenane-type (1), a bergamotane-type (2), a drimane-type (3), and two bisabolane-type (5-6) sesquiterpenoids have been isolated from Biscogniauxia sp. 71-10-1-1. Their structures were determined by spectroscopic analyses, quantum chemical ECD calculations,13C chemical shifts calculations, and X-ray crystallography. This is the first report of campherenane-type and drimane-type sesquiterpenoids from Biscogniauxia. Furthermore, the anti-inflammatory assays of all compounds are evaluated, and the results showed that compounds 3 and 7 exhibited the effects against the production of the pro-inflammatory cytokine TNF-α.


Assuntos
Sesquiterpenos , Xylariales , Sesquiterpenos/farmacologia , Sesquiterpenos/química , Sesquiterpenos Policíclicos , Estrutura Molecular
13.
Plant Dis ; 108(7): 1972-1975, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38381962

RESUMO

Polygonatum cyrtonema Hua is a perennial herb of the Asparagaceae family that is used for both dietary and medicinal purposes in China. In September 2019, a new leaf spot disease on Polygonatum cyrtonema was detected and is currently widespread in Huaihua, Hunan Province, China. Pathogenic fungi were isolated and purified from samples of diseased tissue that were collected for morphological and molecular phylogenetic studies. The pathogen was identified using multilocus (ITS, TEF-1, and TUB2) phylogenies, as well as morphological characters, and was found to be clustered but separately divergent from species of Pestalotiopsis. However, there were significant morphological differences between the pathogen and similar species. The pathogen was finally identified as a new species that was designated Pestalotiopsis xuefengensis. This is the first report of Pestalotiopsis xuefengensis serving as the causal agent of gray leaf spot on Polygonatum cyrtonema. This study will provide useful information for the diagnosis and management of this disease.


Assuntos
Filogenia , Doenças das Plantas , Polygonatum , Doenças das Plantas/microbiologia , China , Polygonatum/microbiologia , Xylariales/genética , Xylariales/classificação , Xylariales/isolamento & purificação , Folhas de Planta/microbiologia
14.
PeerJ ; 12: e16837, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38304186

RESUMO

Turfgrass is frequently used today in the arrangement and aesthetic beautification of grounds in parks, gardens, median strips, recreation and sports areas. In this study, surveys were conduct in turfgrass areas in the three provinces of Türkiye. As a result of isolations from the collected samples, 44 Microdochium isolates obtained belonging to five different species including M. bolleyi, M. majus, M. nivale, M. paspali and M. sorghi which have different virulences. Identification of the isolates were performed by rDNA-ITS sequence analyzes. According to the pathogenicity tests results, the most virulent species was M. nivale M62 with a disease severity value of 91.93%. This was followed by M. bolleyi M1584 and M. majus M63, with disease severity values of 91.12% and 91.08%, respectively. The virulence of M. bolleyi isolates varied among the species. Only 13 of the 31 M. bolleyi species were found to be virulent in turfgrass, M. paspali was less virulent than the others in Poa pratensis. The most virulent isolate of each Microdochium species was tested on four different cereal varieties. M. sorghi and M. paspali had low virulence values in barley and oat than the other Microdochium species, while the other three species showed high virulence in turfgrass, wheat and barley, other than oat. In the phylogenetic neighboor-joining tree belonging to 44 Microdochium isolates clearly demonstrated that the isolates were grouped into five distinct clusters. M. nivale and M. majus were considered genetically close isolates.


Assuntos
Grão Comestível , Xylariales , Filogenia , Virulência/genética , Doenças das Plantas
15.
Carbohydr Res ; 535: 108987, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38048745

RESUMO

Three previously undescribed isopimarane-type diterpene glycosides named as xylarcurcosides A-C (1-3) along with two known ones 16-α-d-mannopyranosyloxyisopimar-7-en-19-oic acid (4) and hypoxylonoid A (5) were successfully isolated from an ethyl acetate extract of the endophytic fungus Xylaria curta YSJ-5 growing in leaves of Alpinia zerumbet. The spectroscopic methods, electronic circular dichroism (ECD) calculations, and X-ray diffraction experiments were conducted to identify their absolute chemical structures. All these compounds were tested for in vitro cytotoxic, anti-inflammatory, α-glucosidase inhibitory, and antibacterial activities. As a result, these novel compounds demonstrated no obvious cytotoxic and antibacterial activity.


Assuntos
Antineoplásicos , Ascomicetos , Diterpenos , Xylariales , Abietanos , Estrutura Molecular , Glicosídeos/química , Xylariales/química , Diterpenos/química , Diterpenos/farmacologia , Antibacterianos/farmacologia , Antibacterianos/química , Antineoplásicos/química
16.
Arch Microbiol ; 206(1): 35, 2023 Dec 23.
Artigo em Inglês | MEDLINE | ID: mdl-38141073

RESUMO

Interest in Antarctic fungi has grown due to their resilience in harsh environments, suggesting the presence of valuable compounds from its organisms, such as those presenting photoprotective potential, since this environment suffers the most dangerous UV exposure in the world. Therefore, this research aimed to assess the photoprotective potential of compounds from sustainable marine sources, specifically seaweed-derived fungi from Antarctic continent. These studies led to discovery of photoprotective and antioxidant properties of metabolites from Arthrinium sp., an endophytic fungus from Antarctic brown algae Phaeurus antarcticus. From crude extract, fractions A-I were obtained and compounds 1-6 isolated from E and F fractions, namely 3-Hydroxybenzyl alcohol (1), (-)-orthosporin (2), norlichexanthone (3), anomalin B (4), anomalin A (5), and agonodepside B (6). Compounds 1, 2, and 6 were not previously reported in Arthrinium. Fraction F demonstrated excellent absorbance in both UVA and UVB regions, while compound 6 exhibited lower UVB absorbance, possibly due to synergistic effects. Fraction F and compound 6 displayed photostability and were non-phototoxic to HaCaT cells. They also exhibited antioxidant activity by reducing intracellular ROS production induced by UVA in keratinocyte monolayers and reconstructed human skin models (resulting in 34.6% and 30.2% fluorescence reduction) and did not show irritation potential in HET-CAM assay. Thus, both are promising candidates for use in sunscreens. It is noted that Fraction F does not require further purification, making it advantageous, although clinical studies are necessary to confirm its potential applicability for sunscreen formulations.


Assuntos
Raios Ultravioleta , Xylariales , Humanos , Protetores Solares/farmacologia , Protetores Solares/química , Pele , Antioxidantes/farmacologia , Antioxidantes/metabolismo
17.
Molecules ; 28(21)2023 Oct 24.
Artigo em Inglês | MEDLINE | ID: mdl-37959666

RESUMO

Four new sesterterpenes, arthproliferins A-D (1-4), together with four known derivatives, were isolated and characterized from the mangrove-sediment-derived fungus Arthrinium sp. SCSIO41221. Their structures were determined using detailed nuclear magnetic resonance (NMR) and mass spectroscopic (MS) analyses. Some of the isolated compounds were evaluated for their cytotoxicity in vitro. The results revealed that terpestacin (6) exhibited significant activity with an IC50 value of 20.3 µM, and compounds 2 and 5 were found to show weak inhibitory effects against U87MG-derived GSCs.


Assuntos
Sesterterpenos , Xylariales , Sesterterpenos/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular
18.
Mar Drugs ; 21(10)2023 Oct 18.
Artigo em Inglês | MEDLINE | ID: mdl-37888476

RESUMO

The Arctic-derived fungus Eutypella sp. D-1 can produce numerous secondary metabolites, and some compounds exhibit excellent biological activity. Seven pimarane-type diterpenes, including three new compounds eutypellenone F (1), libertellenone Y (2), and libertellenone Z (3), and four known compounds (4-7), were isolated from fermentation broth of Eutypella sp. D-1 by the OSMAC strategy of adding ethanol as a promoter in the culture medium. Compound 2 has a rare tetrahydrofuran-fused pimarane diterpene skeleton. The anti-inflammatory activity of all compounds was evaluated. Compounds 3-6 showed a significant inhibitory effect on cell NO release at 10 µmol/L by in vitro experiments, of which 3-5 had inhibitory rates over 60% on nitric oxide (NO) release. Subsequently, the anti-inflammatory activity of 3-5 was evaluated based on a zebrafish model, and the results showed that 3 had a significant inhibitory effect on inflammatory cells migration at 40 µmol/L, while 4 and 5 had a significant inhibitory effect at 20 µmol/L. Moreover, compounds 3-5 have the same conjugated double bond structure, which may be an important group for these compounds to exert anti-inflammatory activity.


Assuntos
Diterpenos , Xylariales , Animais , Abietanos/química , Peixe-Zebra , Linhagem Celular Tumoral , Xylariales/química , Diterpenos/química , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/metabolismo , Estrutura Molecular
19.
J Agric Food Chem ; 71(39): 14125-14136, 2023 Oct 04.
Artigo em Inglês | MEDLINE | ID: mdl-37750514

RESUMO

Target based molecular design via the aid of computation is one of the most efficient methods in the discovery of novel pesticides. Here, a combination of the comparative molecular field analysis (CoMFA) and molecular docking was applied for discovery of potent fungicidal [1,2,4]-triazolo-[3,4-b][1,3,4]-thiadiazoles. Bioassay results indicated that the synthesized target compounds 3a, 3b, and 3c exhibited good activity against Alternaria solani, Botrytis cinerea, Cercospora arachidicola, Fusarium graminearum, Physalospora piricola, Rhizoctonia solani, and Sclerotinia sclerotiorum with an EC50 value falling between 0.64 and 16.10 µg/mL. Specially, 3c displayed excellent fungicidal activity against C. arachidicola and R. solani, which was 5 times more potent than the lead YZK-C22. The enzymatic inhibition assay and fluorescence quenching analysis with R. solani pyruvate kinase (RsPK) showed a weaker binding affinity between RsPK and 3a, 3b, or 3c. Transcriptomic analyses showed that 3c exerted its fungicidal activity by disrupting steroid biosynthesis and ribosome biogenesis in eukaryotes. These findings support that 3c is a promising fungicide candidate, and a fine modification from a lead may lead to a totally different mode of action.


Assuntos
Fungicidas Industriais , Tiadiazóis , Xylariales , Relação Estrutura-Atividade , Simulação de Acoplamento Molecular , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Tiadiazóis/farmacologia , Antifúngicos/farmacologia
20.
PLoS One ; 18(9): e0285855, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-37725599

RESUMO

Phylogenetic relationships within the oestroid subclades Rhinophorinae (Calliphoridae) and Polleniidae were reconstructed for the first time, applying a Sanger sequencing approach using the two protein-coding nuclear markers CAD (carbamoyl-phosphate synthetase 2, aspartate transcarbamylase, and dihydroorotase; 1794 bp) and MCS (molybdenum cofactor sulfurase; 2078 bp). Three genera of Polleniidae and nineteen genera of Rhinophorinae were analyzed together with a selection of taxa representing the major lineages of Oestroidea (non-rhinophorine Calliphoridae, Oestridae, Sarcophagidae, Tachinidae). The selected markers provide good resolution and moderate to strong support of the distal branches, but weak support for several deeper nodes. Polleniidae (cluster flies) emerge as monophyletic and their sister-group relationship to Tachinidae is confirmed. Morinia Robineau-Desvoidy as currently circumscribed emerges as paraphyletic with regard to Melanodexia Williston, and Pollenia Robineau-Desvoidy is the sister taxon of the Morinia-Melanodexia clade. We propose a classification with two subfamilies, Moriniinae Townsend (including Morinia, Melanodexia, and Alvamaja Rognes), and Polleniinae Brauer & Bergenstamm (including Pollenia, Dexopollenia Townsend, and Xanthotryxus Aldrich). Anthracomyza Malloch and Nesodexia Villeneuve are considered as Oestroidea incertae sedis pending further study. Rhinophorinae (woodlouse flies) emerge as monophyletic and sister to a clade composed of (Ameniinae + (Ameniinae + Phumosiinae)), and a tribal classification is proposed with the subfamily divided into Rhinophorini Robineau-Desvoidy, 1863 and Phytonini Robineau-Desvoidy, 1863 (the Stevenia-group and the Phyto-group of authors, respectively). Oxytachina Brauer & Bergenstamm, 1891, stat. rev. is resurrected to contain nine Afrotropical rhinophorine species currently assigned to genus Rhinomorinia Brauer & Bergenstamm, 1891: Oxytachina approximata (Crosskey, 1977) comb. nov., O. atra (Bischof, 1904) comb. nov., O. bisetosa (Crosskey, 1977) comb. nov., O. capensis (Brauer & Bergenstamm, 1893) comb. nov., O. scutellata (Crosskey, 1977) comb. nov., O. setitibia (Crosskey, 1977) comb. nov., O. verticalis (Crosskey, 1977) comb. nov., O. vittata Brauer & Bergenstamm, 1891, and O. xanthocephala (Bezzi, 1908) comb. nov.


Assuntos
Aspartato Carbamoiltransferase , Brassicaceae , Dípteros , Xylariales , Animais , Dípteros/genética , Calliphoridae , Filogenia
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