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In this study, the fungicidal activities of the fungicides azoxystrobin, difenoconazole + propiconazole, carbendazim, flutriafol, fluopyram + tebuconazole, mancozeb and thiophanate-methyl against rice blast and dirty panicle pathogens were evaluated under laboratory and field conditions. Mancozeb exhibited the highest level of fungicidal activity against the blast pathogen Pyricularia oryzae , with an EC 50 value of 0.25 parts per million (ppm). The combination of two fungicides, fluopyram + tebuconazole, showed the strongest fungicidal effect against Bipolaris oryzae and Curvularia lunata , with EC 50 values of 0.587 ppm and 0.435 ppm , respectively. Meanwhile, carbendazim and flutriafol demonstrated the best level of fungicidal activity against Fusarium incarnatum , with the lowest EC 50 values of 0.211 ppm and 0.214 ppm , respectively. The results showed that the fungicides, triazole and strobilurin, had significant effects against rice blast and dirty panicle diseases. The combination of fluopyram + tebuconazole, when applied twice, was the most effective in reducing dirty panicle disease by up to 60% and increasing rice yield by 29% more than the untreated control. Fluopyram + tebuconazole, difenoconazole + propiconazole, flutriafol and azoxystrobin achieved stronger fungicidal activity against rice blast disease, reducing its severity by 32–33% when applied twice by foliar spraying. However, carbendazim, mancozeb and thiophanate-methyl had low to moderate fungicidal activity against both rice diseases in this study.

To select antagonistic yeasts for the control of fruit rot caused by Lasiodiplodia theobromae and anthracnose caused by Colletotrichum gloeosporioides in postharvest mango fruit, 307 yeast strains isolated from plant leaves were evaluated for their antagonistic activities against these two fungal pathogens in vitro. Torulaspora indica DMKU-RP31, T. indica DMKU-RP35 and Pseudozyma hubeiensis YE-21 were found to inhibit the growth of L. theobromae whereas only Papiliotrema aspenensis DMKU-SP67 inhibited the growth of C. gloeosporioides. Antagonistic mechanisms of these four antagonistic yeasts in vitro consisted of the production of antifungal volatile organic compounds (VOCs), biofilm formation and siderophore production. T. indica DMKU-RP35 was the most effective strain in controlling fruit rot on postharvest mango fruits. Its action was comparable to that of the fungicide, benomyl, reducing the disease severity by 82.4%, whereas benomyl revealed 87.5% reduction. P. aspenensis DMKU-SP67 reduced anthracnose severity by 94.1%, which was comparable to that of using benomyl (93.9%). The antifungal VOCs produced by these yeast strains also reduced the severity of these diseases on postharvest mango fruits but at lower rates than using yeast cells. Therefore, these antagonistic yeasts have the potential for use as biological control agents for the control of fruit rot and anthracnose diseases.

The sensitivity of the biocontrol agents for plant disease control, Trichoderma , Talaromyces and Bacillus to 27 fungicides at the recommended rate and half the recommended rate, and 10 plant crude extracts at 10 and 50 g L −1 were evaluated. The results showed that the same fungal species exhibited sensitivity to or compatibility with each fungicide in the same way. Trichoderma harzianum strains displayed the highest resistance on potato dextrose agar mixed with each fungicide followed by T. asperellum , T. hamatum , T. reesei , T. viride , Talaromyces flavus and T. tratensis , respectively. Carbendazim, prochloraz, propiconazole, tebuconazole, fluopyram + tebuconazole, tebuconazole + trifloxystrobin, thiophanate-methyl and triforine at both rates tested inhibited mycelial growth by 100% in all Trichoderma and Talaromyces species tested. Meanwhile, Bacillus amyloliquefaciens showed more compatibility with fungicides and crude plant extracts than B. subtilis strains. The extracts of Syzygium aromaticus and Piper betle completely inhibited all antagonistic microbe growth whereas all antagonists tested grew normally on P. longum extract even at 50 g L −1 . Moreover, the results revealed a negative effect of Trichoderma species on rice seedling germination and growth; they inhibited rice germination up to 80% when applied as seed treatment at 10 6 spores/ g. The results of this study indicate the sensitivity of antagonistic Trichoderma , Talaromyces and Bacillus strains to fungicides and crude plant extracts. The results provide useful data for integrated disease management using combinations of fungicides, crude plant extracts and biocontrol agents. The study also cautions the application of Trichoderma as seed dressing in rice.

The crude ethyl acetate extract of the culture of a marine sponge-associated fungus, KUFA 0098, was tested for its capacity to inhibit the growth of ten phytopathogenic fungi, . , , , , , , , , , and At a concentration of 1 g/L, the crude extract was most active against , causing the highest growth inhibition (55.32%) of this fungus but inactive against and . At a concentration of 10 g/L, the crude extract completely inhibited the growth of most of the fungi, except for , , and , with 94.50%, 74.12%, and 67.80% of inhibition, respectively. The crude extract of KUFA 0098 exhibited growth-inhibitory effects against and , causative agents of brown leaf spot disease and leaf blast disease, respectively, on rice plant var. KDML105, under greenhouse conditions. Chromatographic fractionation and purification of the extract led to the isolation of four previously described depsidones, unguinol ( ), 2-chlorounguinol ( ), 2,4-dichlorounguinol ( ), and folipastatin ( ), as well as one polyphenol, aspergillusphenol A ( ). The major compounds, i.e., , , and , were tested against the ten phytopathogenic fungi. Compounds and were able to inhibit growth of most of the fungi, except , and . Compound showed the same minimum inhibitory concentration (MIC) values as that of carbendazim against , , , and , while compound showed the same MIC values as that of carbendazim against only and . Compound was not active against all of the ten phytopathogenic fungi tested.

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

Fourteen fungicides and three marine-derived fungi were tested for their activities in the promotion of rice seedling development and their efficacy in controlling rice sheath blight disease in two rice varieties, RD43 and KMDL105, under greenhouse conditions. The results showed that the rice seeds treated with carbendazim 50%SC and azoxystrobin 25%SC displayed the best promotion of rice growth in root length and shoot height at seven and 14 days in rice var. RD43. Rice seeds from var. KMDL105 treated with thiophanate-methyl 70%WP exhibited significant stimulation of rice seedling growth resulting in the greatest increase in root length and shoot height at seven and 14 days. In pot experiments with rice var. RD43, spraying with triforine 19%EC, propiconazole 25%EC, trifloxystrobin 50%WG, and validamycin 3%SL showed a high level of fungicidal activity in controlling sheath blight disease, with this evidenced by significant suppression of the disease severity by 71–75% and 61–73% at seven and 14 days after inoculation, respectively. The treatment of rice var. KMDL105 with validamycin 3%SL exhibited the best activity in controlling sheath blight disease by reducing disease severity by up to 62% and 64% at seven and 14 days, respectively. The antagonistic marine fungi tested in this study displayed low activity against sheath blight disease and low effects on rice seedling promotion compared to fungicides. Specifically, Trichoderma harzianum KUFA 0689 and T. asperellum KUFA 0677 reduced sheath blight disease severity by 42–46% and 27–37% at seven and 14 days, respectively.

Acknowledgments: This work was partially supported through national funds provided by the FCT/MCTES-Foundation for Science and Technology from the Minister of Science, Technology and Higher Education (PIDDAC) and European Regional Development Fund (ERDF) through the COMPETE—Programa Operacional Factores de Competitividade (POFC) programme, under the project PTDC/MAR-BIO/4694/2014 (reference POCI-01-0145-FEDER-016790; Project 3599-Promover a Produção Científica e Desenvolvimento Tecnológico e a Constituição de Redes Temáticas (3599-PPCDT)) in the framework of the program PT2020 as well as by the project INNOVMAR-Innovation and Sustainability in the Management and Exploitation of Marine Resources (reference NORTE-01-0145-FEDER-000035, within Research Line NOVELMAR), supported by North Portugal Regional Operational Program (NORTE 2020), under the PORTUGAL 2020 Partnership Agreement, through the European Regional Development Fund (ERDF). We thank Júlia Bessa and Sara Cravo for technical support.

Five undescribed pentaketide derivatives, (R)-6,8-dihydroxy-4,5-dimethyl-3-methylidene-3,4-dihydro-1H-2-benzopyran-1-one (1), [(3S,4R)-3,8-dihydroxy-6-methoxy-4,5-dimethyl-1-oxo-3,4-dihydro-1H-isochromen-3-yl]methyl acetate (2), (R)-5, 7-dimethoxy-3-((S)-(1-hydroxyethyl)-3,4-dimethylisobenzofuran-1(3H)-one (4b), (S)-7-hydroxy-3-((S)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran 1(3H)-one (5), and a p-hydroxyphenyl-2-pyridone derivative, avellaneanone (6), were isolated together with the previously reported (R)-3-acetyl-7-hydroxy-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (3), (R)-7-hydroxy-3-((S)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (4a) and isosclerone (7), from the ethyl acetate extract of a culture of a marine sponge-derived fungus, Hamigera avellanea KUFA0732. The structures of the undescribed compounds were elucidated using 1D and 2D NMR, as well as high-resolution mass spectral analyses. The absolute configurations of the stereogenic carbons in 1, 4b, 5, and 6 were established by X-ray crystallographic analysis. The absolute configurations of C-3 and C-4 in 2 were determined by ROESY correlations and on the basis of their common biosynthetic origin with 1. The crude fungal extract and the isolated compounds 1, 3, 4b, 5, 6, and 7 were assayed for their growth inhibitory activity against various plant pathogenic fungi viz. Alternaria brassicicola, Bipolaris oryzae, Colletotrichum capsici, C. gloeosporiodes, Curvularia oryzae, Fusarium semitectum, Lasiodiplodia theobromae, Phytophthora palmivora, Pyricularia oryzae, Rhizoctonia oryzae and Sclerotium rolfsii.

A new ergosterol analog, talarosterone (1) and a new bis-anthraquinone derivative (3) were isolated, together with ten known compounds including palmitic acid, ergosta-4,6,8(14),22- tetraen-3-one, ergosterol-5,8-endoperoxide, cyathisterone (2), emodin (4a), questinol (4b), citreorosein (4c), fallacinol (4d), rheoemodin (4e) and secalonic acid A (5), from the ethyl acetate extract of the culture of the marine sponge-associated fungus Talaromyces stipitatus KUFA 0207. The structures of the new compounds were established based on extensive 1D and 2D spectral analysis, and in the case of talarosterone (1), the absolute configurations of its stereogenic carbons were determined by X-ray crystallographic analysis. The structure and stereochemistry of cyathisterone (2) was also confirmed by X-ray analysis. The anthraquinones 4a-e and secalonic acid A (5) were tested for their anti-obesity activity using the zebrafish Nile red assay. Only citreorosein (4c) and questinol (4b) exhibited significant anti-obesity activity, while emodin (4a) and secalonic acid A (5) caused toxicity (death) for all exposed zebrafish larvae after 24 h. © 2017 by the authors. Licensee MDPI.

An unreported isocoumarin, (3S,4R)-4-hydroxy-6-methoxymellein (2), an undescribed propylpyridinium anthraquinone (4), and an unreported C-glucosyl resorcinol derivative, acetyl carnemycin E (5c), were isolated, together with eight previously reported metabolites including p-hydroxybenzaldehyde (1), 1,3-dimethoxy-8-hydroxy-6-methylanthraquinone (3a), 1,3-dimethoxy-2,8-dihydroxy-6-methylanthraquinone (3b), emodin (3c), 5[(3E,5E)-nona-3,5-dien-1-yl]benzene (5a), carnemycin E (5b), tajixanthone hydrate (6a) and 15-acetyl tajixanthone hydrate (6b), from the ethyl acetate extract of the culture of a marine sponge-derived fungus, Aspergillus stellatus KUFA 2017. The structures of the undescribed compounds were elucidated by 1D and 2D NMR and high resolution mass spectral analyses. In the case of 2, the absolute configurations of the stereogenic carbons were determined by comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. The absolute configurations of the stereogenic carbons in 6a and 6b were also determined, for the first time, by X-ray crystallographic analysis. Compounds 2, 3a, 3b, 4, 5a, 5b, 5c, 6a, and 6b were assayed for antibacterial activity against four reference strains, viz. two Gram-positive (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and two Gram-negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853), as well as three multidrug-resistant strains. However, only 5a exhibited significant antibacterial activity against both reference and multidrug-resistant strains. Compound 5a also showed antibiofilm activity against both reference strains of Gram-positive bacteria.