RESUMO
Four new monomeric sorbicillinoids, trichillinoids A - D (1-4), along with two known dimeric sorbicillinoids (5 and 6), and five known monomeric sorbicillinoids (7-11), were obtained from the marine-fish-derived fungus Trichoderma sp. G13. They were structurally characterized on the basis of comprehensive spectroscopic investigations (NMR, HRESIMS, and ECD). Compounds 1-4 displayed moderate anti-inflammatory activities, according to inhibiting the production of NO in RAW264.7 cells activated with IC50 values ranging from 14 to 20 µM.
Assuntos
Anti-Inflamatórios , Trichoderma , Camundongos , Animais , Células RAW 264.7 , Estrutura Molecular , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/isolamento & purificação , Trichoderma/química , Óxido Nítrico/metabolismo , Peixes/microbiologia , ChinaRESUMO
An undescribed trichodenone derivative (1), two new diketopiperazines (3 and 4) along with a bisabolane analog (2) were isolated from Trichoderma hamatum b-3. The structures of the new findings were established through comprehensive analyses of spectral evidences in HRESIMS, 1D and 2D NMR, Marfey's analysis as well as comparisons of ECD. The absolute configuration of 2 was unambiguously confirmed by NMR, ECD calculation and Mo2(AcO)4 induced circular dichroism. Compounds 1-4 were tested for their fungicidal effects against eight crop pathogenic fungi, among which 1 showed 51% inhibition against Sclerotinia sclerotiorum at a concentration of 50 µg/mL.
Assuntos
Hypocreales , Trichoderma , Estrutura Molecular , Dicetopiperazinas/química , Trichoderma/químicaRESUMO
From the fungus Trichoderma sp., we isolated seven novel 18-residue peptaibols, neoatroviridins E-K (1-7), and six new 14-residue peptaibols, harzianins NPDG J-O (8-13). Additionally, four previously characterized 18-residue peptaibols neoatroviridins A-D (14-17) were also identified. The structural configurations of the newly identified peptaibols (1-13) were determined by comprehensive nuclear magnetic resonance (NMR) and high-resolution electrospray ionization tandem mass spectrometry (HR-ESI-MS/MS) data. Their absolute configurations were further determined using Marfey's method. Notably, compounds 12 and 13 represent the first 14-residue peptaibols containing an acidic amino acid residue. In antimicrobial assessments, all 18-residue peptaibols (1-7, 14-17) exhibited moderate inhibitory activities against Staphylococcus aureus 209P, with minimum inhibitory concentration (MIC) values ranging from 8-32 µg·mL-1. Moreover, compound 9 exhibited moderate inhibitory effect on Candida albicans FIM709, with a MIC value of 16 µg·mL-1.
Assuntos
Anti-Infecciosos , Trichoderma , Peptaibols/farmacologia , Peptaibols/química , Trichoderma/química , Trichoderma/metabolismo , Espectrometria de Massas em Tandem/métodos , Anti-Infecciosos/farmacologia , Espectrometria de Massas por Ionização por Electrospray/métodosRESUMO
Four new polyketides named trichodermatides A-D (1-4), along with five known analogues (5-9), were isolated from the fungus Trichoderma sp. XM-3. Their structures were elucidated on the basis of HRESIMS and NMR analyses, and their absolute configurations were determined by ECD comparison, 1H and 13C NMR calculation, DP4+ analysis, modified Mosher's method, and X-ray crystallography. Trichodermaketone D (9) showed mild antibacterial activity against Pseudomonas aeruginosa.
Assuntos
Policetídeos , Trichoderma , Trichoderma/química , Estrutura Molecular , Espectroscopia de Ressonância Magnética , Cristalografia por Raios XRESUMO
Eight new phenethoxy derivatives, trichoasperellins A-H (1-8), were isolated from the endophytic fungus Trichoderma asperellum G10 isolated from the medicinal plant Areca catechu L. The structures of these compounds were elucidated from spectroscopic data, J-based configurational analysis, and Mosher's methods. Compounds 1-4 and 6-8 bear one or two multioxidized C7 moieties with the same carbon skeleton. The carbon skeletons of compounds 6-8 are new, all containing three moieties connected via two acetal carbons similar to those of disaccharide glycosides. Compound 4 inhibited nitric oxide production with an IC50 value of 48.3 µM, comparable to that of the positive control indomethacin (IC50, 42.3 µM).
Assuntos
Hypocreales , Trichoderma , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Areca , Carbono , Estrutura Molecular , Trichoderma/químicaRESUMO
Six new sesquiterpenoids including three bisabolane derivatives, trichobisabolins O1, O2, and P (1-3), two nerolidol derivatives, trichonerolins A and B (4 and 5), one acorane, trichoacorin A (6), along with one new steroid, isoergokonin B (7), were isolated from the culture of Trichoderma brevicompactum A-DL-9-2 obtained from the inner tissue of the red alga Chondria tenuissima. Their structures and relative configurations were assigned by interpretation of 1D/2D NMR and MS data. As acyclic sesquiterpenoids, compounds 4 and 5 were discovered from Trichoderma for the first time. Compounds 1-7 were evaluated for the inhibition of some marine-derived organisms, in which, 3 and 4/5 exhibited potent inhibition against Amphidinium carterae and Chattonella marina with IC50 of 1.8 µg/mL and 1.2 µg/mL, respectively. In addition, compound 7 could inhibit the growth of Pseudoalteromonas citrea with an MIC value of 64 µg/mL.
Assuntos
Anti-Infecciosos/farmacologia , Produtos Biológicos/farmacologia , Fitoplâncton/efeitos dos fármacos , Rodófitas/microbiologia , Sesquiterpenos/farmacologia , Trichoderma/química , Anti-Infecciosos/isolamento & purificação , Produtos Biológicos/isolamento & purificação , Hypocreales , Estrutura Molecular , Pseudoalteromonas/efeitos dos fármacos , Sesquiterpenos/isolamento & purificaçãoRESUMO
Biosynthesis of silver nanoparticles using beneficial Trichoderma harzianum is a simple, eco-friendly and cost-effective route. Secondary metabolites secreted by T. harzianum act as capping and reducing agents that can offer constancy and can contribute to biological activity. The present study aimed to synthesize silver nanoparticles using T. harzianum cell filtrate and investigate different bioactive metabolites based on LC-MS/MS analysis. The synthesized silver nanoparticles (AgNPs) from T. harzianum were characterized by ultraviolet-visible spectrophotometry, Fourier transform infrared spectrometry (FT-IR), energy-dispersive spectroscopy (EDS), dynamic light scattering (DLS), X-ray powder diffraction (XRD) and scanning electron microscopy (SEM). The surface plasmon resonance of synthesized particles formed a peak centered near 438 nm. The DLS study determined the average size of AgNPs to be 21.49 nm. The average size of AgNPs was measured to be 72 nm by SEM. The cubic crystal structure from XRD analysis confirmed the synthesized particles as silver nanoparticles. The AgNPs exhibited remarkable antioxidant properties, as determined by DPPH and ferric reducing antioxidant power (FRAP) assay. The AgNPs also exhibited broad-spectrum antibacterial activity against two Gram-positive bacteria (S. aureus and B. subtilis) and two Gram-negative bacteria (E. coli and R. solanacearum). The minimum inhibitory concentration (MIC) of AgNPs towards bacterial growth was evaluated. The antibacterial activity of AgNPs was further confirmed by fluorescence microscopy and SEM analysis.
Assuntos
Antibacterianos/farmacologia , Antioxidantes/química , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Nanopartículas Metálicas/toxicidade , Prata/química , Trichoderma/metabolismo , Antibacterianos/química , Biomassa , Química Verde , Nanopartículas Metálicas/química , Testes de Sensibilidade Microbiana , Tamanho da Partícula , Extratos Vegetais/química , Trichoderma/químicaRESUMO
We tested the ability of 14 strains of Trichoderma to emit volatile compounds that decreased or stopped the growth of Phytophthora infestans. Volatile organic compounds (VOCs) emitted from Trichoderma strains designated T41 and T45 inhibited the mycelial growth of P. infestans grown on a laboratory medium by 80 and 81.4%, respectively, and on potato tubers by 93.1 and 94.1%, respectively. Using the DNA sequence analysis of the translation elongation factor region, both Trichoderma strains were identified as Trichoderma atroviride. VOCs emitted by the strains were analyzed, and 39 compounds were identified. The most abundant compounds were 3-methyl-1-butanol, 6-pentyl-2-pyrone, 2-methyl-1-propanol, and acetoin. Electron microscopy of the hyphae treated with T. atroviride VOCs revealed serious morphological and ultrastructural damages, including cell deformation, collapse, and degradation of cytoplasmic organelles. To our knowledge, this is the first report describing the ability of Trichoderma VOCs to suppress the growth of the late blight potato pathogen.
Assuntos
Fungicidas Industriais/farmacologia , Phytophthora infestans/efeitos dos fármacos , Doenças das Plantas/microbiologia , Solanum tuberosum/microbiologia , Trichoderma/química , Compostos Orgânicos Voláteis/farmacologia , Fungicidas Industriais/química , Fungicidas Industriais/metabolismo , Phytophthora infestans/crescimento & desenvolvimento , Tubérculos/microbiologia , Trichoderma/metabolismo , Compostos Orgânicos Voláteis/química , Compostos Orgânicos Voláteis/metabolismoRESUMO
Selected microbial strains used as active ingredients of biopesticides for agricultural management practices (e.g., IPM, Integrated Pest Management) are known for their ability to control phytopathogens, promote plant growth, and/or induce disease resistance. Microbes belonging to the Trichoderma genus are considered as an appropriate example of beneficial microbes and are model organisms to study plant-microbe interactions. Several Trichoderma strains are marketed as biocontrol agents and are known to increase plant growth, stress tolerance, and nutrient availability. These effects have sometimes been related to the production of effector metabolites that beneficial microbes produce during the interaction with plant and other microbes. Secondary metabolites (SMs) comprise different classes of natural compounds with low molecular weight and having numerous biological roles, especially in the interactions among organisms. Metabolomic analysis of the interactions between plants, phytopathogens, and beneficial fungi aided in the identification of several bioactive fungal SMs that positively affect plant metabolism. Some of these compounds showed direct activity against phytopathogens, but also increased disease resistance by triggering the plant defence system, and/or enhanced vegetative growth. A new generation of bioformulations based on microbial metabolites and living consortia responsible for the desired beneficial effects on crops may overcome the difficulties associated with the use of a single living microbial strain.
Assuntos
Produtos Agrícolas/efeitos dos fármacos , Trichoderma/químicaRESUMO
Two new cyclonerane sesquiterpenes, (10E)-isocyclonerotriol (1) and (10Z)-isocyclonerotriol (2), and one new isocoumarin derivative, trichophenol A (3), were isolated from Trichoderma citrinoviride A-WH-20-3, an endophyte from the marine red alga Laurencia okamurai. Their structures and relative configurations were assigned by spectroscopic techniques, highlighted by using Sarotti's DP4+ sheet to confirm the cyclopentane ring. The absolute configuration of 1 was established by comparison of experimental and calculated specific rotation data. Compounds 1 and 2 represent the first occurrence of ring-isomerized cycloneranes. Compound 3 is the first 3-phenylisocoumarin derivative from Trichoderma and features inhibition of several marine-derived bacteria and phytoplankton species.
Assuntos
Isocumarinas/química , Sesquiterpenos/química , Trichoderma/química , Endófitos/química , Laurencia/microbiologia , Estrutura Molecular , Fitoplâncton/efeitos dos fármacosRESUMO
Eight new highly oxygenated fungal polyketides, namely, 15-hydroxy-1,4,5,6-tetra-epi-koninginin G (1), 14-hydroxykoninginin E (2), koninginin U (3), 4'-hydroxykoninginin U (4), koninginin V (5), 14-ketokoninginin B (6), 14-hydroxykoninginin B (7), and 7-O-methylkoninginin B (8), together with six known related analogues (9-14), were isolated from Trichoderma koningiopsis QA-3, a fungus obtained from the inner root tissue of the well known medicinal plant Artemisia argyi. All these compounds are bicyclic polyketides, with compound 1 contains unusual hemiketal moiety at C-5 and compounds 2-14 having ketone group at C-1 and double bond at C-5(6). The structures and absolute configurations of the new compounds were established by spectroscopic analysis, X-ray crystal diffraction, modified Mosher's method, and ECD calculation. The absolute configurations of the known compounds 9, 10, and 12 were determined by X-ray crystal diffractions for the first time. The antimicrobial activities against human pathogen, marine-derived aquatic bacteria, and plant-pathogenic fungi of compounds 1-14 were evaluated, and compound 1 showed remarkable activity against aquatic pathogen Vibrio alginolyticus with MIC value 1 µg/mL, which is as active as that of the positive control.
Assuntos
Antibacterianos/farmacologia , Artemisia/química , Plantas Medicinais/química , Policetídeos/farmacologia , Trichoderma/metabolismo , Vibrio alginolyticus/efeitos dos fármacos , Antibacterianos/química , Antibacterianos/metabolismo , Relação Dose-Resposta a Droga , Testes de Sensibilidade Microbiana , Estrutura Molecular , Oxigênio/metabolismo , Raízes de Plantas/química , Policetídeos/química , Policetídeos/metabolismo , Relação Estrutura-Atividade , Trichoderma/químicaRESUMO
The core of solid tumors is characterized by hypoxia and a nutrient-starved microenvironment and has gained much attention as targets of anti-cancer drugs. In the course of search for selective growth inhibitors against the cancer cells adapted to nutrient starvation, epidithiodiketopiperazine DC1149B (1) together with structurally related compounds, trichodermamide A (2) and aspergillazine A (3), were isolated from culture extract of marine-derived Trichoderma lixii. Compounds 1 exhibited potent selective cytotoxic activity against human pancreatic carcinoma PANC-1 cells cultured under glucose-starved conditions with IC50 values of 0.02 µM. The selective index of the compound 1 was found to be 35,500-fold higher for cells cultured under glucose-starved conditions than those under the general culture conditions. The mechanistic analysis indicated that compound 1 inhibited the response of the ER stress signaling. In addition, these effects of compound 1 could be mediated by inhibiting complex II in the mitochondrial electron transport chain.
Assuntos
Antineoplásicos/farmacologia , Dipeptídeos/farmacologia , Neoplasias/tratamento farmacológico , Piperazinas/farmacologia , Trichoderma/química , Linhagem Celular Tumoral , Dipeptídeos/química , Transporte de Elétrons/efeitos dos fármacos , Glucose/metabolismo , Inibidores do Crescimento/farmacologia , Humanos , Mitocôndrias/metabolismo , Microambiente TumoralRESUMO
Trichocadinins B-G (1-6), six new cadinane-type sesquiterpene derivatives, each with C-14 carboxyl functionality, were isolated from the culture extract of Trichoderma virens QA-8, an endophytic fungus obtained from the fresh inner tissue of the medicinal plant Artemisia argyi. Their structures were elucidated by interpretation of the NMR spectroscopic and mass spectrometric data. The structures and absolute configurations of compounds 1 and 3 were confirmed by X-ray crystallographic analysis. Compounds 1-3 showed antibacterial and antifungal activity.
Assuntos
Artemisia/química , Plantas Medicinais/química , Sesquiterpenos Policíclicos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Trichoderma/química , Antibacterianos/farmacologia , Antifúngicos/farmacologia , Artemisia/microbiologia , Cristalografia por Raios X , Estrutura Molecular , Plantas Medicinais/microbiologia , Sesquiterpenos/química , Análise Espectral/métodosRESUMO
An examination of the endophytic fungus Trichoderma asperellum A-YMD-9-2 obtained from the marine red alga Gracilaria verrucosa led to the isolation of seven new chromanoid norbisabolane derivatives, trichobisabolins I-L (1-4) and trichaspsides C-E (5-7). Their structures and relative configurations were established on the basis of spectroscopic techniques, mainly including 1D/2D NMR and MS, and the absolute configuration of 1 was assigned by X-ray crystallographic analysis using Cu Kα radiation. All of these isolates feature a 1,9-epoxy ring system, and 5-7 represent the second occurrence of norbisabolane aminoglycosides. Compounds 1-7 exhibited potent inhibition of several marine phytoplankton species.
Assuntos
Aminoglicosídeos/farmacologia , Cromanos/farmacologia , Gracilaria/microbiologia , Trichoderma/química , Aminoglicosídeos/química , Aminoglicosídeos/isolamento & purificação , Cromanos/isolamento & purificação , Cristalografia por Raios X , Endófitos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Trichoderma/fisiologiaRESUMO
Six new (1-6), together with seven known (7-13), trichothecenes were isolated from the soil-derived Trichoderma brevicompactum PSU-RSPG27. Their structures were established using spectroscopic data. The structure of 1 was confirmed by X-ray data. Trichodermin (7) exhibited the most potent activity against Plasmodium falciparum (K1 strain) with an IC50 value of 0.1 µM, while other trichothecenes (1, 8, 9, and 12) were much less active, with IC50 values in the range of 7.1-9.6 µM. Compound 7 displayed activity against noncancerous Vero cells with an IC50 value of 0.4 µM. The remaining compounds showed moderate to weak activity, with IC50 values in the range of 6.9-15.3 µM. Compounds 7 and 12 were active against human oral carcinoma (KB) cells with IC50 values of 2.4 and 3.7 µM, respectively. Additionally, compounds 7 and 12 displayed antifungal activity against Candida albicans with the respective MIC values of 1 and 2 µg/mL and were active against Cryptococcus neoformans with equal MIC values of 4 µg/mL.
Assuntos
Microbiologia do Solo , Trichoderma/química , Tricotecenos/isolamento & purificação , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Linhagem Celular Tumoral , Avaliação Pré-Clínica de Medicamentos , Humanos , Concentração Inibidora 50 , Testes de Sensibilidade Microbiana , Plasmodium falciparum/efeitos dos fármacos , Espectroscopia de Prótons por Ressonância Magnética , Espectrometria de Massas por Ionização por Electrospray , Tricotecenos/química , Tricotecenos/farmacologiaRESUMO
Eight new bisabolane derivatives, trichobisabolins A-H, along with two known ones, (3R,6R,7R)-1,10-bisaboladien-3-ol (9) and (3R,6R,7S)-1,10-bisaboladien-3,6-diol (10) were isolated from the culture of Trichoderma asperellum Y6-2, obtained from the surface of the marine red alga Chondrus ocellatus. Their structures and relative configurations were identified by interpretation of 1D/2D NMR and MS data. Compounds 1-8 were assayed for inhibiting the growth of some marine-derived organisms, including four marine phytoplankton species, one marine zooplankton species, and five pathogenic bacteria. All of them exhibited inhibition against the marine phytoplanktons with IC50 values ranging from 2.1-78⯵g/mL, compounds 4 and 8 showed weak lethality to the marine zooplankton, and none of them had inhibition against the five pathogenic bacteria.
Assuntos
Bactérias/efeitos dos fármacos , Chondrus/microbiologia , Cicloexanos/farmacologia , Fitoplâncton/efeitos dos fármacos , Trichoderma/química , China , Cicloexanos/isolamento & purificação , Estrutura Molecular , Relação Estrutura-AtividadeRESUMO
From the green alga Cladophora sp. collected in Italy, the marine fungal strain A12 of Trichoderma citrinoviride was isolated, identified and characterized. LC-MS qTOF analysis was applied to perform a metabolic profile of the fungal culture. Chromatographic techniques and spectroscopic methods were used to isolate and characterize the major secondary metabolites produced by this strain in liquid culture. In particular, four known sorbicillinoids (trichodermanone C, spirosorbicillinol A, vertinolide and sorbicillin) were purified and identified, together with 2-phenylethanol and tyrosol. Moreover, metabolomic analysis allowed to detect small amounts of trichodimerol, rezishanone A, 2',3'-dihydrosorbicillin and bisvertinol. For the first time a significant inhibitory effect on nitrite levels has been shown for trichodermanone C in lipopolysaccharide-stimulated J774A.1 macrophages.
Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Macrófagos/efeitos dos fármacos , Nitritos/metabolismo , Resorcinóis/farmacologia , Trichoderma/química , Alcenos/metabolismo , Animais , Anti-Inflamatórios não Esteroides/química , Hidrocarbonetos Aromáticos com Pontes/metabolismo , Linhagem Celular , Clorófitas/microbiologia , Cromatografia Líquida , Avaliação Pré-Clínica de Medicamentos , Compostos Heterocíclicos com 3 Anéis/metabolismo , Itália , Lipopolissacarídeos/farmacologia , Macrófagos/metabolismo , Espectrometria de Massas/métodos , Metabolômica/métodos , Camundongos , Estrutura Molecular , Resorcinóis/metabolismo , Metabolismo Secundário , Trichoderma/isolamento & purificação , Trichoderma/metabolismoRESUMO
Three cyclonerane sesquiterpenoids, including the known cyclonerodiol (1), together with its new derivatives, (10E)-12-acetoxy-10-cycloneren-3,7 -diol (2) and 12-acetoxycycloneran-3,7-diol (3) were isolated from the cultures of marine-sediment-derived fungus Trichoderma harzianum P1-4. The structures of the new compounds (2 and 3) were elucidated based on extensive spectroscopic methods (1D/2D NMR and HR-MS) and optical rotation analysis.
Assuntos
Sesquiterpenos/química , Trichoderma/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Bacillus subtilis/efeitos dos fármacos , Avaliação Pré-Clínica de Medicamentos , Sedimentos Geológicos/microbiologia , Espectroscopia de Ressonância Magnética/métodos , Estrutura Molecular , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Staphylococcus aureus/efeitos dos fármacosRESUMO
Chemical investigation on the solid rice culture of Trichoderma atroviride S361, an endophyte isolated from Cephalotaxus fortunei, has afforded a pair of novel N-furanone amide enantiomers, (-)-trichodermadione A (1a) and (+)-trichodermadione A (1b), and a new cyclohexenone sesquiterpenoid, trichodermadione B (2), together with six known secondary metabolites. Chiral separation of compound 1 was successfully performed on a Lux Cellulose-2 column. Their structures were elucidated by detailed spectroscopic analyses on the basis of NMR, HRMS, and ECD data, and the absolute configurations of the new compounds were determined by computational analyses of their electronic circular dichroism (ECD) spectra and Snatzke's method. Compounds 1a, 1b and 2 were also evaluated for their cytotoxicity against DU145 and PC3 cell lines, as well as inhibitory effects against the production of NO in LPS-stimulated RAW264.7 cells.
Assuntos
Cephalotaxus/microbiologia , Trichoderma/química , Animais , Linhagem Celular Tumoral , Endófitos/química , Humanos , Camundongos , Estrutura Molecular , Células RAW 264.7RESUMO
Five new botryane sesquiterpenes (1: -5: ), one new cyclopentadepsipeptide (9: ), and two new xanthones (11: â-â12: ), together with 11 known compounds, were isolated from Trichoderma oligosporum. The structures of the new compounds were identified by comprehensive spectroscopic methods including nuclear magnetic resonance and mass spectrometry. The cytotoxicity of 1: -19: was evaluated against K562, A549, and ASPC cell lines. Compounds 5, 8, 11, 17: , and 18: showed cytotoxicity against the K562 cell line with more than 50% inhibition at 12.5 µM. As to A549 cell line, compound 8: showed the strongest cytotoxicity with approximately 50% inhibition at 25.0 µM. No compounds showed cytotoxicity against the ASPC cell line.