RESUMO
Two new sesquiterpenes, trichocitrinovirenes A (1) and B (2), and five known compounds including four structurally related sesquiterpenes and one γ-lactone were isolated from the soil-derived fungus Trichoderma citrinoviride PSU-SPSF346. The structures were identified by analysis of their spectroscopic data. The relative configuration was assigned based on NOEDIFF data. The absolute configuration of compound 1 was established according to specific rotations and ECD data while that of compound 2 was proposed based on biosynthetic considerations. Compound 2 possesses a rare bicyclic sesquiterpene skeleton. The antimicrobial and cytotoxic activities of the isolated compounds were evaluated.
RESUMO
Seven new polyketides including a phenol (1), two diphenyl ethers (2 and 3), two depsidones (4 and 5), and two phthalides (6 and 7) were isolated from the fungus Aspergillus unguis PSU-MF16 along with 27 known compounds. Their structures were determined by extensive spectroscopic analysis. The absolute configurations of 1 and 4-7 were established using comparative analyses of calculated and experimental ECD spectra. Among the new metabolites, 2 exhibited the best antimicrobial activity against Staphylococcus aureus, methicillin-resistant S. aureus, and Microsporum gypseum with equal MIC values of 16 µg/mL. In addition, known emeguisin A displayed potent antimicrobial activity against S. aureus, methicillin-resistant S. aureus, and Cryptococcus neoformans with equal MIC values of 0.5 µg/mL, compared with the standard drugs, vancomycin and amphotericin B. The structure-activity relationship study of the isolated compounds for antimicrobial activity is discussed.
Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Aspergillus/química , Policetídeos/farmacologia , Animais , Antibacterianos/isolamento & purificação , Antifúngicos/isolamento & purificação , Arthrodermataceae/efeitos dos fármacos , Chlorocebus aethiops , Cryptococcus neoformans/efeitos dos fármacos , Dysidea/microbiologia , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Policetídeos/isolamento & purificação , Relação Estrutura-Atividade , Tailândia , Células VeroRESUMO
Three new compounds including one furanone, one morpholinone and one tetrahydrofuran together with three known compounds were isolated from the broth extract of the marine-derived fungus Talaromyces sp. PSU-MF07. The structures of the isolated compounds were determined on the basis of spectroscopic methods. The relative configuration was assigned using NOEDIFF data whereas the absolute configurations were established by Mosher's method, specific rotations and electronic circular dichroism (ECD) data. Some isolated compounds were tested for antimicrobial activity. Only known penioxalicin exhibited weak antibacterial activity against methicillin-resistant Staphylococcus aureus SK1 with an MIC value of 200 µg/mL.
RESUMO
Contaminated fungi on dried salted fish of three species including Talang queenfish (TQF, Scomberroides commersonianus), Hamilton's thryssa fish (HTF, Thryssa hamiltonii), and Cobia fish (CF, Rachycentron canadum) were isolated and identified. One hundred and sixty-nine isolates were obtained from TQF and HTF, respectively, while no fungi were detected in CF. The dominant genera were Aspergillus spp. (n = 79), Penicillium spp. (n = 60), and non-sporulating fungi (n = 30). The representative groups of Aspergillus spp. (n = 6) and Penicillium spp. (n = 3) based on different morphological characteristics were selected for species identification by molecular methods involving ITS1-5.8s-ITS2 region and Matrix-Assisted Laser Desorption/Ionization Time-of Flight Mass Spectrometer (MALDI-TOF MS) analysis. The nine isolates were identified to be Aspergillus versicolor (n = 2), Aspergillus montevidensis (n = 3), Penicillium citrinum (n = 3), and Aspergillus sp. (n = 1). The antifungal activity of chitooligosaccharide-gallic acid (COS-GAL) conjugate against A. versicolor F1/10M9, A. montevidensis F1/30M20, and P. citrinum F1/23M14 was examined. The minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) values were in the range of 0.625-2.5 mg/mL and 1.25-10 mg/mL, respectively. COS-GAL conjugate at the concentration of 5 mg/mL completely inhibited the spore germination of A. versicolor F1/10M9 and P. citrinum F1/23M14 after 72 h of treatment. COS-GAL conjugate at 4 × MIC mainly affected the mycelium of A. versicolor F1/10M9 and P. citrinum F1/23M14 after treatment with COS-GAL conjugate for 3 days by coating mycelium surface and reducing the size of mycelium. Therefore, COS-GAL conjugate could be used as a food additive to inhibit or prevent the growth of fungi contaminated in dried salted fish or other relevant products. PRACTICAL APPLICATION: During processing, dried salted fish can be contaminated with fungi, which may cause food poisoning and food spoilage. The contaminated fungi are capable of producing mycotoxin that is harmful to consumers. Synthetic food preservatives have long been used to inhibit fungal growth, but the side effects to consumers are of concern. Chitooligosaccharide is a nontoxic chitosan derivative produced from shrimp shell and its conjugate namely chitooligosaccharide-gallic acid conjugate showed high efficacy in inhibiting the growth of fungi including Aspergillus spp. and Penicillium spp. Therefore, it can serve as a natural alternative preservative for the prevention of fungal growth in dried salted fish.
Assuntos
Quitosana , Penicillium , Animais , Fungos , Antifúngicos/farmacologia , Quitosana/farmacologia , Peixes/microbiologiaRESUMO
Two new hydroquinones bearing a 1,3-enyne moiety, pestalotioquinols G and H, together with four known compounds, including pestalotioquinol A, phomonitroester, (R)-4,6,8-trihydroxy-3,4-dihydronaphthalen-1(2H)-one, and scylatone were isolated from the marine fungus Pestalotiopsis diploclisia (BCC 35283). The structures of these compounds were elucidated by analysis of 2D-NMR and HR-MS data. The known pestalotioquinol A displayed antimalarial activity against Plasmodium falciparum K1 with an IC50 value of 19.0 µM, while pestalotioquinol G displayed weak cytotoxic activity against Vero cell lines with an IC50 value of 47.9 µM.
Assuntos
Fungos , Hidroquinonas , Estrutura Molecular , Fungos/química , Pestalotiopsis , PlantasRESUMO
One new nonadride enantiomer, ent-epiheveadride, along with five known dioxopiperazine derivatives were isolated from the marine-derived fungus Aspergillus chevalieri PSU-AMF79. Their structures were identified by extensive spectroscopic analysis. The absolute configuration of ent-epiheveadride was determined by comparison of the specific rotation and electronic circular dichroism data with those of related known compounds. It exhibited antifungal activity against Cryptococcus neoformans ATCC90113 flucytosine-resistant and Candida albicans NCPF3153 with the MIC values of 128 and 200 µg/mL, respectively. In addition, the known L-alanyl-L-tryptophan anhydride displayed TMEM16A inhibitory activity with 65.0% inhibition at a concentration of 5 µg/mL.
Assuntos
Aspergillus , Fungos , Aspergillus/química , Antifúngicos/química , Dicroísmo Circular , Estrutura Molecular , Testes de Sensibilidade MicrobianaRESUMO
The soil-derived fungus Talaromyces thailandensis PSU-SPSF059 produced one new vermistatin derivative, talarostatin, and seven known compounds including two vermistatins, two chrodrimanins, two diphenyl ethers and one penicillide derivative. Extensive spectroscopic analysis was performed to identify their structures. The absolute configuration of talarostatin was determined by comparing the experimental and calculated electronic circular dichroism data. The antimicrobial and cytotoxic activities of the isolated secondary metabolites were also evaluated.
RESUMO
Karst caves are distinctive ecosystems that have limited nutrients, darkness, low to moderate temperatures, and high moisture levels, which allow for a diverse range of fungal communities to thrive. Despite their significance, little is understood about the fungi found in karst caves in Thailand. In 2019, we studied the cultured mycobiota from five substrate types (air, water, rock, soil/sediment, and organic debris) in two karst caves (Le Stegodon and Phu Pha Phet Caves) of the Satun UNESCO Global Geopark, southern Thailand. A cumulative count of 829 distinct fungal morphological types was identified, encompassing 319 fungal culturable were observed. Based on preliminary analyses of the internal transcribed spacer (ITS) sequence using BLAST searches, the most common phylum among the fungal morphotypes was Ascomycota, harboring 282 species in 91 genera, 93.4% of which were distributed in the classes Eurotiomycetes, Sordariomycetes, and Dothideomycetes. The most common fungal genera identified in the two karst caves were Aspergillus, Penicillium, Cladosporium, Talaromyces, Xylaria, and Trichoderma, with 45, 41, 24, 14, 14, and 6 species identified, respectively. Discovering fungi in Thai karst caves highlights the extensive fungal diversity in the Satun UNESCO Global Geopark, implying undiscovered species, and emphasizing the need for comprehensive investigations in other unexplored Thai karst caves.
Assuntos
Ascomicetos , Penicillium , Ecossistema , Tailândia , AspergillusRESUMO
Four new aromatic polyketides including two diphenyl ethers (pseudopithoethers A-B, 1-2), one benzofuranone (pseudopithonone, 3) and one xanthone (pseudopithoxanthone, 4), along with two known compounds (5-6) and one new naturally occurring hydroquinone (α,2,5-trihydroxyacetophenone, 7) were isolated from the marine-derived fungus Pseudopithomyces maydicus PSU-AMF350. Their structures were identified by analysis of spectroscopic data. All isolated compounds were tested for antimicrobial activity. Only compound 7 displayed antibacterial activity against methicillin-resistant Staphylococcus aureus with the MIC value of 128 µg/mL and against S. aureus, Acinetobacter baumannii NPRC005 and A. baumannii NPRC007 with the same MIC value of 200 µg/mL.[Formula: see text].
Assuntos
Ascomicetos , Staphylococcus aureus Resistente à Meticilina , Policetídeos , Xantonas , Antibacterianos/química , Hidroquinonas , Testes de Sensibilidade Microbiana , Estrutura Molecular , Éteres Fenílicos , Policetídeos/química , Staphylococcus aureus , Xantonas/farmacologiaRESUMO
One new 2-oxaspiro[4.5]decane, roussoellide, and one new α-pyrenocine, 2',3'-dihydropyrenocine A, together with nine known compounds including known arthropsolide A, and pyrenocines A and E, were obtained from the culture broth of the endophytic fungus Roussoella sp. Their structures were determined using spectroscopic data. The absolute configuration of known arthropsolide A was assigned on the basis of X-ray diffraction data using Cu Kα radiation. Known pyrenocine A displayed weak cytotoxic activity against breast cancer (MCF-7) cells with an IC50 value of 27.1 µM and weak antifungal activity against Microsporum gypseum SH-MU-4 with an MIC value of 615.2 µM.[Formula: see text].
Assuntos
Antifúngicos , Ascomicetos , Alcanos , Antifúngicos/química , Antifúngicos/farmacologia , Ascomicetos/química , Estrutura Molecular , Compostos de EspiroRESUMO
Two new compounds, one α-pyrone (trichoharzianone) and one decalin (trichoharzianin), along with eight known compounds including three decalins, two δ-lactones, two carboxylic acids and one isochroman were isolated from the marine-derived fungus Trichoderma harzianum PSU-MF79. The structures were determined by spectroscopic methods. The relative configuration of trichoharzianin was assigned based on NOEDIFF data and coupling constants whereas the absolute configurations were established by comparison of electronic circular dichroism data with those of the co-metabolites. Known (-)-massoia lactone exhibited mild antifungal activity against Cryptococcus neoformans ATCC90113 flucytosine-resistant, Candida albicans ATCC90028 and C. albicans NCPF3153 with MIC values of 128, 200 and 200 µg/mL, respectively, and weak cytotoxic activity against HCT-116 and MCF-7 cell lines with the respective IC50 values of 17 and 32 µM. In addition, it was noncytotoxic against noncancerous Vero cells with an IC50 value of >100 µM.
Assuntos
Hypocreales , Trichoderma , Chlorocebus aethiops , Animais , Humanos , Pironas/farmacologia , Células Vero , Estrutura Molecular , Candida albicans , Lactonas , Trichoderma/químicaRESUMO
Karst caves are oligotrophic environments that appear to support a high diversity of fungi. Studies of fungi in Thailand's caves are limited. During a 2019 exploration of the mycobiota associated with soil samples from a karst cave, namely, Phu Pha Phet in the Satun UNESCO Global Geopark in Satun Province, southern Thailand, two previously undescribed fungi belonging to Talaromyces (Trichocomaceae, Eurotiales, Eurotiomycetes) were studied using a polyphasic approach combining phenotypic and molecular data. Based on datasets of four loci (ITS, BenA, CaM, and RPB2), phylogenetic trees of the section Trachyspermi were constructed, and two new species-Talaromyces phuphaphetensis sp. nov. and T. satunensis sp. nov.-phylogenetically related to T. subericola, T. resinae, and T. brasiliensis, are described. Detailed descriptions and illustrations of the new species are provided. This study increases the number of cave-dwelling soil fungi discovered in Thailand's Satun UNESCO Global Geopark, which appears to be a unique environment with a high potential for discovering fungal species previously undescribed.
RESUMO
Three new sesquiterpenes, named aspergillusenes A and B and (+)-(7S)-7-O-methylsydonic acid, and two new hydrogenated xanthone derivatives, named aspergillusones A and B, were isolated from the sea fan-derived fungus Aspergillus sydowii PSU-F154 together with 10 known compounds. Their structures were identified on the basis of spectroscopic data. The isolated compounds were evaluated for their antioxidant activity.
Assuntos
Antozoários/microbiologia , Antioxidantes/isolamento & purificação , Aspergillus/química , Sesquiterpenos/isolamento & purificação , Xantonas/isolamento & purificação , Animais , Antioxidantes/química , Antioxidantes/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Xantonas/química , Xantonas/farmacologiaRESUMO
Five new metabolites, fusaranthraquinone (1), fusarnaphthoquinones A-C (2-4), and fusarone (5), were isolated from the sea fan-derived fungi Fusarium spp. PSU-F14 and PSU-F135 along with 18 known compounds. The structures were elucidated on the basis of spectroscopic evidence. Their antibacterial, antifungal, antimycobacterial, antimalarial, and cytotoxic activities were examined.
Assuntos
Antozoários/microbiologia , Antraquinonas/isolamento & purificação , Antraquinonas/farmacologia , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Antimaláricos/isolamento & purificação , Antimaláricos/farmacologia , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Ciclopentanos/isolamento & purificação , Ciclopentanos/farmacologia , Fusarium/química , Naftoquinonas/isolamento & purificação , Naftoquinonas/farmacologia , Animais , Antraquinonas/química , Antibacterianos/química , Antifúngicos/química , Antimaláricos/química , Antineoplásicos/química , Chlorocebus aethiops , Ciclopentanos/química , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Células KB , Testes de Sensibilidade Microbiana , Estrutura Molecular , Mycobacterium tuberculosis/efeitos dos fármacos , Naftoquinonas/química , Ressonância Magnética Nuclear Biomolecular , Oceanos e Mares , Plasmodium falciparum/efeitos dos fármacos , Células VeroRESUMO
Pyrones, named nigrosporapyrones A-D (1-4), and five known compounds were isolated from the marine-derived fungus Nigrospora PSU-F18. Their structures were elucidated on the basis of spectroscopic evidence. The antibacterial activity against the standard Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus was evaluated.
Assuntos
Antibacterianos/química , Ascomicetos/química , Pironas/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Ressonância Magnética Nuclear Biomolecular , Pironas/isolamento & purificação , Pironas/farmacologia , Staphylococcus aureus/efeitos dos fármacosRESUMO
Two new fungal metabolites, penicipyrone (1), and penicilactone (2), were isolated from the marine-derived fungus Penicillium sp. PSU-F44 along with three known macrolides, (+)-brefeldin A (3), (+)-brefeldin C (4), and 7-oxobrefeldin A (5). Their antimicrobial activities against methicillin-resistant Staphylococcus aureus SK1 and Microsporum gypseum SH-MU-4 were examined.
Assuntos
Antibacterianos/química , Lactonas/química , Penicillium/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Lactonas/isolamento & purificação , Lactonas/farmacologia , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade MicrobianaRESUMO
Three new compounds including two depsidones (simplicildones J and K) and one dihydroxanthenone (globosuxanthone E) together with nine known compounds were obtained from the crude extracts of two endophytic fungi Simplicillium lanosoniveum (J.F.H. Beyma) Zare & W. Gams PSU-H168 and PSU-H261 which were isolated from the leaves of Hevea brasiliensis. The structures were elucidated by spectroscopic evidence. The absolute configuration of globosuxanthone E was established by means of experimental and calculated TDDFT ECD data. Simplicildone K exhibited antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus with equal MIC values of 128⯵g/mL. Simplicildone K and globosuxanthone E displayed antifungal activity against Cryptococcus neoformans ATCC90113 with the same MIC values of 32⯵g/mL. In addition, known botryohordine C and simplicildone A showed phosphodiesterase 5 inhibitory activity with the IC50 values of 5.69 and 9.96⯵M, respectively, and were noncytotoxic toward noncancerous Vero cells.
Assuntos
Depsídeos/farmacologia , Hevea/microbiologia , Hypocreales/química , Lactonas/farmacologia , Xantonas/farmacologia , Animais , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Chlorocebus aethiops , Cryptococcus neoformans/efeitos dos fármacos , Depsídeos/isolamento & purificação , Endófitos/química , Lactonas/isolamento & purificação , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Inibidores da Fosfodiesterase 5/isolamento & purificação , Inibidores da Fosfodiesterase 5/farmacologia , Folhas de Planta/microbiologia , Tailândia , Células Vero , Xantonas/isolamento & purificaçãoRESUMO
Nigrospoxydons A-C (1- 3) and nigrosporapyrone (4), four new metabolites, were isolated from the marine-derived fungus Nigrospora sp. PSU-F5 together with nine known compounds. Their structures were elucidated by spectroscopic methods, mainly 1D and 2D NMR spectroscopic techniques. The antibacterial activity against the standard Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus was evaluated.
Assuntos
Ascomicetos/química , Produtos Biológicos/isolamento & purificação , Pironas/isolamento & purificação , Antibacterianos/química , Antibacterianos/isolamento & purificação , Produtos Biológicos/química , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Pironas/química , Pironas/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
Nine previously undescribed depsidones (simplicildones A-I) and one previously undescribed α-pyrone (simplicilopyrone) were isolated from the endophytic fungus Simplicillium sp. PSU-H41 along with 11 known compounds. Their structures were established by extensive spectroscopic analysis. Simplicildone A and known botryorhodine C displayed weak antibacterial against Staphylococcus aureus with equal MIC values of 32 µg/mL. Additionally, botryorhodine C was active against methicillin-resistant S. aureus with the same MIC value. Simplicildone C exhibited weak antifungal activity against Cryptococcus neoformans with an MIC value of 32 µg/mL. In addition, simplicildones A and C and botryorhodine C were noncytotoxic against noncancerous Vero cells.
Assuntos
Antibacterianos/isolamento & purificação , Antifúngicos/isolamento & purificação , Depsídeos/isolamento & purificação , Euphorbiaceae/química , Hevea/química , Lactonas/isolamento & purificação , Pironas/isolamento & purificação , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Antifúngicos/química , Antifúngicos/farmacologia , Chlorocebus aethiops , Cryptococcus neoformans/efeitos dos fármacos , Depsídeos/química , Depsídeos/farmacologia , Lactonas/química , Lactonas/farmacologia , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Folhas de Planta/química , Pironas/química , Pironas/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Células VeroRESUMO
Chromatographic separation of the broth extract of the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178 resulted in isolation of four γ-butenolide-furanone dimers, aspersclerotiorones A-D, a furanone derivative, aspersclerotiorone E, and two γ-butenolide derivatives, aspersclerotiorones F and G, together with six known compounds, penicillic acid, dihydropenicillic acid, 5,6-dihydro-6-hydroxypenicillic acid, 6-methoxy-5,6-dihydropenicillic acid, coculnol and (4R,5R)-4,5-dihydroxy-3-methoxy-5-methylcyclohex-2-en-1-one. Their structures were determined by spectroscopic evidence. For aspersclerotiorones A and B, the structures were confirmed by single-crystal X-ray diffraction crystallography. Penicillic acid displayed weak antibacterial activity against Staphylococcus aureus and Escherichia coli with equal MIC values of 128 µg/mL, and it was noncytotoxic towards African green monkey kidney fibroblast cells.