Synthesis and in vitro antifungal activity of new Michael-type amino derivatives of xanthatin, a natural sesquiterpene lactone from Xanthium strumarium L.

Structural optimization using plant secondary metabolites as templates is one of the important approach to discover pesticide molecules with novel skeletons. Xanthatin, a natural sesquiterpene lactone isolated from the Xanthium plants (Family: Compositae), exhibits important biological properties. In this work, a series of Michael-type amino derivatives were prepared from xanthatin and their structures were characterized by 1H NMR, 13C NMR and HR-MS, and their antifungal activities against several phytopathogenic fungi were evaluated according to the spore germination method and mycelium growth rate method in vitro. The results illustrated that compounds 2g (IC50 = 78.91 µg/mL) and 2o (IC50 = 64.51 µg/mL) exhibited more promising inhibition activity against spores of F. solani than precursor xanthatin, compounds 2g, 2l, and 2r exhibited remarkable antifungal effect on C. mandshurica with the average inhibition rates (AIRs) >90%, whereas the AIR of xanthatin was only 59.34%. Meanwhile, the preliminary structure-activity relationships suggested that the amino containing 2-methoxyethyl or 4-chlorophenylmethyl group appended in the C-13 position of xanthatin could yield potential compounds against fungal spores, and the exocyclic double bond of xanthatin is essential to maintain its mycelial growth inhibitory activity. Therefore, the aforementioned findings indicate that partial xanthatin amino-derivatives could be considered for further exploration as the potential lead structures toward development of the new environmentally friendly fungicidal candidates for sustainable crop protection.

Essential Oil of Lepidium virginicum: Protective Activity on Anthracnose Disease and Preservation Effect on the Nutraceutical Content of Tamarillo Fruit (Solanum betaceum).

The essential oil from the annual plant Lepidium virginicum L. was chemically characterized in three consecutive years (2018-2020). The essential oils were evaluated in vitro and in situ on the causal agent of anthracnose in tamarillo fruits (Solanum betaceum). The main volatile constituents were phenylacetonitrile (>60 %), linalool (>10 %), limonene (>7 %) and α-terpineol (>5 %). The essential oil (MIC, 19-30 µg mL-1 ), phenylacetonitrile (MIC, 45 µg mL-1 ) and α-terpineol (MIC, 73 µg mL-1 ) caused a significant inhibition in the conidial viability from a wild strain of Colletotrichum acutatum, which was isolated and identified as a causal agent of anthracnose. The inoculation of conidia from C. acutatum in non-symptomatic tamarillo fruits, followed by the in situ treatment with different concentrations of the essential oil (>30 µg mL-1 ), phenylacetonitrile and α-terpineol, significantly (p<0.01) avoided the degradation of anthocyanins (delphinidin 3-O-rutinoside, cyanidin 3-O-rutinoside and pelargonidin 3-O-rutinoside) and carotenoids (ß-cryptoxanthin and ß-carotene) as well as retarded yellowing and necrosis triggered by anthracnose at least for 10 days. Our results suggest the potential use of the essential oil from L. virginicum as a natural component to preserve the nutraceutical content of tamarillo fruits against C. acutatum infection.

Bioactivities of Allium longicuspis Regel against anthracnose of mango caused by Colletotrichum gloeosporioides (Penz.).

The present study focused on the effect of Allium longicuspis extracts (ALE) against anthracnose of mango fruit. In vitro tests (mycelial growth and conidial germination) showed that, ALE concentrated from 0.75 to 2.5 g L-1 completely inhibited the growth of Colletotrichum gloesporioides. Cytoplasmic discharge, mycelial and conidial blasts were clearly observed when applied with ALE. The minimum effective concentration (MEC) of ALE at 0.75 g L1 can be applied as protective, curative and simultaneous treatment in mango fruit to inhibit the anthracnose infection. Efficacy of garlic extract was relatively superior to synthetic fungicide based on protective, curative and simultaneous treatments. Twenty chemical components were detected in ALE based on GCMS analysis (Table 1). The six major components were the following: oleyl alcohol, methyl ether (42.04%), γ-sitosterol (15.85%), , 24-norursa-3.12-diene (5.62%), 1-octadecanol methyl ether (4.23%), n-pentadecanol (3.95%) and 2-vinyl-4h-1 3-dithiine (3.76%). The findings support the potential use of ALE as an alternative to synthetic fungicide.

Characterization and antifungal activity of jackfruit (Artocarpus heterophyllus Lam.) leaf extract obtained using conventional and emerging technologies.

With the current agro-food industry demands for more environmentally-friendly production, the use of natural antifungal compounds extracted by emerging technologies led to a sustainable alternative to control microorganisms. Therefore, the present work aimed to: (i) determine antifungal activity against Colletotrichum gloeosporioides and Penicillium italicum of jackfruit leaf extracts obtained by different methods, and (ii) identify compounds by HPLC-DAD-ESI-MS. Microwave (MAE), high-hydrostatic pressure (HHP) and ultrasound (UAE) assisted extractions were tested, followed by fractionation with different polarity solvents. The concentration of total soluble phenols (TSP), tannins (TT) and flavonoids (TF) were determined. Differences not only in the amounts of extracted phytochemicals were found but in the antifungal properties (MAE against P. italicum and HHP against C. gloeosporioides at 5 mg/ml) as well as in the chemical composition determined by HPLC-MS. These results suggest the possible application of jackfruit leaf extracts as a suitable postharvest antifungal treatment.

Antifungal activity of Brazilian red propolis extract and isolation of bioactive fractions by thin-layer chromatography-bioautography.

OBJECTIVES: This study set out to highlight the in vitro and in vivo antifungal activity of an Ethanolic Extract of Red Brazilian Propolis (EERBP) and identify bioactive fractions effective against Colletotrichum musae. METHODS: Active fractions were detected by the thin-layer chromatography-bioautography method and characterised by HPLC-MSn. RESULTS: The in vitro results showed that EERBP had strong antifungal properties againstC. musae (81 ± 1% inhibition at 1.6 g GAE L-1). Medicarpin, (3S)-vestitol and (3S)-neovestitol were the main compounds identified in the EERBP extract (45% of all detected peaks). Two isolated fractions displayed inhibition percentages of 35 ± 4 and 42 ± 1%, respectively, on C. musae mycelial growth compared to the EERBP extract. The biological activity of the two fractions displayed an additive effect. CONCLUSION: A further in vivo investigation revealed that EERBP is a potential natural alternative for controlling banana crown rot.

Dihydroisocoumarins produced by Diaporthe cf. heveae LGMF1631 inhibiting citrus pathogens.

Citrus black spot (CBS) and post-bloom fruit drop (PFD), caused by Phyllosticta citricarpa and Colletotrichum abscissum, respectively, are two important citrus diseases worldwide. CBS depreciates the market value and prevents exportation of citrus fruits to Europe. PFD under favorable climatic conditions can cause the abscission of flowers, thereby reducing citrus production by 80%. An ecofriendly alternative to control plant diseases is the use of endophytic microorganisms, or secondary metabolites produced by them. Strain LGMF1631, close related to Diaporthe cf. heveae 1, was isolated from the medicinal plant Stryphnodendron adstringens and showed significant antimicrobial activity, in a previous study. In view of the potential presented by strain LGMF1631, and the absence of chemical data for secondary metabolites produced by D. cf. heveae, we decided to characterize the compounds produced by strain LGMF1631. Based on ITS, TEF1, and TUB phylogenetic analysis, strain LGMF1631 was confirmed to belong to D. cf. heveae 1. Chemical assessment of the fungal strain LGMF1631 revealed one new seco-dihydroisocoumarin [cladosporin B (1)] along with six other related, already known dihydroisocoumarin derivatives and one monoterpene [(-)-(1S,2R,3S,4R)-p-menthane-1,2,3-triol (8)]. Among the isolated metabolites, compound 5 drastically reduced the growth of both phytopathogens in vitro and completely inhibited the development of CBS and PFD in citrus fruits and flowers. In addition, compound 5 did not show toxicity against human cancer cell lines or citrus leaves, at concentrations higher than used for the inhibition of the phytopathogens, suggesting the potential use of (-)-(3R,4R)-cis-4-hydroxy-5-methylmellein (5) to control citrus diseases.

Glycosylated flavonoids: fruit's concealed antifungal arsenal.

Fruit defense against pathogens relies on induced and preformed mechanisms. The present contribution evaluated performed resistance of red and green mango fruit against the fungal pathogen Colletotrichum gloeosporioides and identified the main active antifungal components. High-performance liquid chromatography analysis of nonhydrolyzed mango peel extracts identified major anthocyanin peaks of glycosylated cyanidin and methylcyanidin, and flavonol peaks of glycosylated quercetin and kaempferol, which were more abundant on the 'red side' of red mango fruit. Organic extracts of red vs green mango peel were more efficient in inhibiting C. gloeosporioides. Transcriptome analysis of the mango-C. gloeosporioides interaction showed increased expression of glucosidase genes related to both fungal pathogenicity and host defense. Glucosidase treatment of organic peel extract increased its antifungal activity. Additionally, quercetin and cyanidin had significantly higher antifungal activity than their glycosylated derivatives. Peel extract volatiles treated with glucosidase had antifungal activity. GCMS analysis identified 15 volatiles after glucosidase hydrolysis, seven of them present only in red fruit. These results suggest that the fruit obtains a concealed arsenal of glycosylated flavonoids in its peel when they are hydrolyzed by ß-glucosidase that is induced in both fungus and host during infection process, become more toxic to the fungal pathogen, inhibiting decay development.

Effects of Bacillus Subtilis CF-3 VOCs Combined with Heat Treatment on the Control of Monilinia fructicola in Peaches and Colletotrichum gloeosporioides in Litchi Fruit.

In order to study the effect of volatile organic compounds (VOCs) produced by Bacillus subtilis CF-3 combined with heat treatment on Monilinia fructicola in peach and Colletotrichum gloeosporioides in litchi fruit, fruits were treated with B. subtilis CF-3 VOCs and hot air alone or in combination. The quality indexes of peach and litchi fruit after treatment and the changes in defense-related enzymes were measured. The results showed that the B. subtilis CF-3 VOCs combined with heat treatment could significantly reduce the rot index of peach and litchi fruit, and effectively maintain firmness and soluble solids content, as well as reduce weight loss of fruits. The combined treatment effectively enhanced the activity of peroxidase (POD), polyphenol oxidase (PPO), catalase (CAT), and superoxide dismutase (SOD) than either treatment alone, and enhanced the resistance of fruit to pathogenic fungi by activating disease-resistant enzymes (phenylalanine ammonia-lyase [PAL], chitinase [CHI], ß-1, 3-glucanase [GLU]) activity. In this study, B. subtilis CF-3 VOCs combined with heat treatment maintained the quality and delayed the decline of peach and litchi fruit, providing a theoretical basis for future applications. PRACTICAL APPLICATION: The combination of B. subtilis CF-3 VOCs and heat treatment reduce the extent of M. fructicola and C. gloeosporioides. The combination maintain the quality of peach and litchi better. The combination obviously improve the activity of defense-related enzyme in fruit.

Mycogenic Selenium Nanoparticles as Potential New Generation Broad Spectrum Antifungal Molecules.

The current challenges of sustainable agricultural development augmented by global climate change have led to the exploration of new technologies like nanotechnology, which has potential in providing novel and improved solutions. Nanotools in the form of nanofertilizers and nanopesticides possess smart delivery mechanisms and controlled release capacity for active ingredients, thus minimizing excess run-off to water bodies. This study aimed to establish the broad spectrum antifungal activity of mycogenic selenium nanoparticles (SeNPs) synthesized from Trichoderma atroviride, and characterize the bioactive nanoparticles using UV-Vis spectroscopy, dynamic light scattering (DLS), Fourier transform infrared (FT-IR), X-ray diffraction (XRD), scanning electron microscopy-energy dispersive X-ray spectroscopy (SEM-EDS), and high-resolution transmission electron microscopy (HR-TEM). The synthesized nanoparticles displayed excellent in vitro antifungal activity against Pyricularia grisea and inhibited the infection of Colletotrichum capsici and Alternaria solani on chili and tomato leaves at concentrations of 50 and 100 ppm, respectively. The SEM-EDS analysis of the bioactive SeNPs revealed a spherical shape with sizes ranging from 60.48 nm to 123.16 nm. The nanoparticles also possessed the unique property of aggregating and binding to the zoospores of P. infestans at a concentration of 100 ppm, which was visualized using light microscope, atomic force microscopy, and electron microscopy. Thus, the present study highlights the practical application of SeNPs to manage plant diseases in an ecofriendly manner, due to their mycogenic synthesis and broad spectrum antifungal activity against different phytopathogens.

Alternative control of grape rots by essential oils of two Eucalyptus species.

BACKGROUND: Essential oils (EOs) are volatile natural compounds produced by plant secondary metabolism, and some of them exhibit antimicrobial activity. The objective of the present study was to determine the chemical composition the EOs of Eucalyptus staigeriana and Eucalyptus globulus, and their effect in vitro and in vivo against Botrytis cinerea and Colletotrichum acutatum, the most important fungal rot diseases of grapes. Moreover, grapes collected from field experiments were used to evaluate the impact of the alternative control on the alcoholic fermentation and wine composition. RESULTS: The major compound of E. staigeriana EO were citral 30.91% (19.74% geranial, 11.17% neral), 1.8-cineole (24.59%) and limonene (19.47%), while 1.8-cineole represented 68.26% of E. globulus EO. The two EOs showed in vitro antifungal activity against both pathogens. Eucalyptus staigeriana EO exhibited the highest activity inhibiting mycelial growth (MG) and conidial germination at 0.5 µL mL-1 . Moreover, this EO was able to reduce the incidence and severity of grey rot caused by B. cinerea and the severity of ripe rot caused by C. acutatum The alternative control did not significantly influence alcoholic fermentation, the physicochemical characteristics, and the volatile composition of wines. CONCLUSION: These results are promising and indicate that E. staigeriana EO might be further investigated as a natural alternative for the control of fungal rots on wine grapes. © 2019 Society of Chemical Industry.

Water-soluble exudates from seeds of Kochia scoparia exhibit antifungal activity against Colletotrichum graminicola.

Plant seed exudates are composed of complex mixtures of chemicals with potential for bioactive compounds with antimicrobial properties. This study focused on kochia (Kochia scoparia), one of many weedy plant species considered invasive in many agricultural systems. Extraction of compounds in water yielded an exudate mass equivalent to 7% of the original seed mass used. Water-soluble exudates were tested against 16 known plant pathogens in disk diffusion assays and kochia exudates were found to inhibit Colletotrichum graminicola, the fungal causative agent of anthracnose and stalk rot in maize. The narrow range of fungi found as targets suggested the mechanism of inhibition may be specific rather than broadly antifungal. A decline in viability of cells over four orders of magnitude occurred within six hours of exposure to exudate. The minimum inhibitory concentration was 3.125 mg L-1. Hyphae formation in C. graminicola appeared inhibited following exposure to the exudate. Small molecular weight compounds as determined by GC/MS analysis showed high relative amounts of the sugars fructose, galactopyranose, glucose, and sorbitol, along with moderate proportions of organic acids and amino acids. Protein content averaged 0.7% in the standard concentration (100 mg mL-1) used for inhibition assays. Size fractionation of the exudate and subsequent disk diffusion assays revealed bioactive fractions with compounds in the MW range <5 kDa. To the best of our knowledge, this study is the first to show promising bioactivity against C. graminicola that was associated with water-extractable compounds from a common weed species. The results suggest that seeds of persistent plant species with long-lived seed banks like kochia may have potential for use in the discovery of compounds active in inhibiting fungal pathogens.

Colletotrichum fioriniae Development in Water and Chloroform-based Blueberry and Cranberry Floral Extracts.

To accurately monitor the phenology of the bloom period and the temporal dynamics of floral chemical cues on fungal fruit rotting pathogens, floral extraction methods and coverslip bioassays were developed utilizing Colletotrichum fioriniae. In blueberry and cranberry, this pathogen is optimally controlled by applying fungicides during the bloom period because of the role flowers play in the initial stages of infection. The protocol detailed here describes how floral extracts (FE) were obtained using water-, chloroform-, and field rainwater-based methods for later use in corresponding glass coverslip bioassays. Each FE served to provide a different set of information: response of C. fioriniae to mobilized floral chemical cues in water (water-based), pathogen response to flower and fruit surface waxes (chloroform-based), and field-based monitoring of collected floral rainwater, moving in vitro observations to an agricultural setting. The FE is broadly described as either water- or chloroform-based, with an appropriate bioassay described to compensate for the inherent differences between these two materials. Rainwater that had run off flowers was collected in unique devices for each crop, alluding to the flexibility and application of this approach for other crop systems. The bioassays are quick, inexpensive, simple, and provide the ability to generate spatiotemporal and site-specific information about the presence of stimulatory floral compounds from various sources. This information will ultimately better inform disease management strategies, as FE decrease the time needed for infection to occur, thus providing insight into changing risks for pathogen infection over the growing season.

ZnO-based nanofungicides: Synthesis, characterization and their effect on the coffee fungi Mycena citricolor and Colletotrichum sp.

In this work we compare the antifungal capacity of zinc oxide nanoparticles (ZnO-NPs) synthesized by a chemical route and a ZnO-based nanobiohybrid obtained by green synthesis in an extract of garlic (Allium sativum). To find out the characteristics of the materials synthesized, X-ray diffraction (XRD), IR spectroscopy and absorption in UV-Vis were used, as well as both scanning (SEM) and transmission (TEM) electron microscopy. The results showed that the samples obtained were of nanometric size (<100 nm), with a predominance of the wurtzite crystal phase of ZnO and little crystallization of the nanobiohybrids. Their antifungal capacity on two pathogenic fungi of coffee, Mycena citricolor (Berk and Curt) and Colletotrichum sp. was also evaluated. Both nanomaterials showed an efficient antifungal capacity, particularly the nanobiohybrids, with ~97% inhibition in growth of M. citricolor, and ~93% for Colletotrichum sp. The microstructural study with high resolution optical (HROM) and ultra-structural microscopy (using TEM) carried out on the fungi treated with the synthesized nanomaterials showed a strong nanofungicidal effect on the vegetative and reproductive structures and fungal cell wall, respectively. The inhibition of the growth of the fungi and micro and ultra-structural affectations were explained considering that the size of the nanomaterials allows them to pass easily through the cell membranes. This indicates that they can be absorbed easily by the fungi tested here, causing cellular dysfunction. Nanofungicide effects are also attributable to the unique properties of nanomaterials, such as the high surface-to-bulk ratio of atoms and their surface physicochemical characteristics that could directly or indirectly produce reactive oxygen species (ROS), which affect the proteins of the cell wall.

Bioassay-Guided Isolation and Structure Elucidation of Fungicidal and Herbicidal Compounds from Ambrosia salsola (Asteraceae).

The discovery of potent natural and ecofriendly pesticides is one of the focuses of the agrochemical industry, and plant species are a source of many potentially active compounds. We describe the bioassay-guided isolation of antifungal and phytotoxic compounds from the ethyl acetate extract of Ambrosia salsola twigs and leaves. With this methodology, we isolated and identified twelve compounds (four chalcones, six flavonols and two pseudoguaianolide sesquiterpene lactones). Three new chalcones were elucidated as (S)-ß-Hydroxy-2',3,4,6'-tetrahydroxy-5-methoxydihydrochalcone (salsolol A), (S)-ß-Hydroxy-2',4,4',6'-tetrahydroxy-3-methoxydihydrochalcone (salsolol B), and (R)-α, (R)-ß-Dihydroxy-2',3,4,4',6'- pentahydroxydihydrochalcone (salsolol C) together with nine known compounds: balanochalcone, six quercetin derivatives, confertin, and neoambrosin. Chemical structures were determined based on comprehensive direct analysis in real time-high resolution mass spectrometry (HR-DART-MS), as well as 1D and 2D NMR experiments: Cosy Double Quantum Filter (DQFCOSY), Heteronuclear Multiple Quantum Coherence (HMQC) and Heteronuclear Multiple Bond Coherence (HMBC), and the absolute configurations of the chalcones were confirmed by CD spectra analysis. Crystal structure of confertin was determined by X-ray diffraction. The phytotoxicity of purified compounds was evaluated, and neoambrosim was active against Agrostis stolonifera at 1 mM, while confertin was active against both, Lactuca sativa and A. stolonifera at 1 mM and 100 µM, respectively. Confertin and salsolol A and B had IC50 values of 261, 275, and 251 µM, respectively, against Lemna pausicotata (duckweed). The antifungal activity was also tested against Colletotrichum fragariae Brooks using a thin layer chromatography bioautography assay. Both confertin and neoambrosin were antifungal at 100 µM, with a higher confertin activity than that of neoambrosin at this concentration.

New Phytotoxic Cassane-like Diterpenoids from Eragrostis plana.

Eragrostis plana (Nees) is an allelopathic plant with invasive potential in South American pastures. To isolate and identify phytotoxic compounds from leaves and roots of E. plana, a bioassay-directed isolation of the bioactive constituents was performed. This is the first report on a new diterpene carbon skeleton, neocassane, and of three new neocassane diterpenes, neocassa-1,12(13),15-triene-3,14-dione, 1; 19-norneocassa-1,12(13),15-triene-3,14-dione, 2; and 14-hydroxyneocassa-1,12(17),15-triene-3-one, 3, identified from the roots. Compounds 1, 2, and 3 inhibited the growth of duckweed by 50% at concentrations of 109 ± 28, 200 ± 37, and 59 ± 15 µM, respectively. Compound 2 was fungicidal to Colletotrichum fragariae, Colletotrichum acutatum, and Colletotrichum gloeosporioides. The compounds identified here could explain the allelopathy of E. plana. The description of the newly discovered compounds, besides contributing to the chemical characterization of the species, may be the first step in the study of the potential of these compounds as bioherbicides.

New butyrolactone and other metabolites from the bark of Endlicheria arenosa against of the phytopathogen Colletotrichum tamarilloi.

In this work, screening of Lauraceae species for their antifungal activity against Collectotrichum tamarilloi was carried out and the ethanol extract derived from the bark of Endlicheria arenosa was found to be the best candidate. From the ethanolic extract of the bark of E. arenosa, the hexane and chloroform fractions were found to be active, from these five fatty acids were identified and two lactones were isolated. The most active fatty acid was the dodecanoic acid with a minimal inhibitory concentration (MIC) of 78.0 µM. The butyrolactone 3R,4R-licunolide A, it has not previously reported, and licunolide B show both the lowest MIC (55.3 µM). This is the first report of compounds of natural origin as growth inhibitors of C. tamarilloi.

New Bis-Alkenoic Acid Derivatives from a Marine-Derived Fungus Fusarium solani H915.

Fusarium solani H915 is a fungus derived from mangrove sediments. From its ethyl acetate extract, a new alkenoic acid, fusaridioic acid A (1), three new bis-alkenoic acid esters, namely, fusariumester A1 (2), A2 (3) and B (4), together with three known compounds (5⁻7), were isolated. The structures of the new compounds were comprehensively characterized by high resolution electrospray ionization-mass spectrometry (HR-ESI-MS), 1D and 2D nuclear magnetic resonance (NMR). Additionally, the antifungal activities against tea pathogenic fungi Pestalotiopsis theae and Colletotrichum gloeosporioides were studied. The new compound, 4, containing a ß-lactone ring, exhibited moderate inhibitory activity against P. theae, with an MIC of 50 µg/disc. Hymeglusin (6), a typical ß-lactone antibiotic and a terpenoid alkaloid, equisetin (7), exhibited potent inhibitory activities against both fungal species. The isolated compounds were evaluated for their effects on zebrafish embryo development. Equisetin clearly imparted toxic effect on zebrafish even at low concentrations. However, none of the alkenoic acid derivatives exhibited significant toxicity to zebrafish eggs, embryos, or larvae. Thus, the ß-lactone containing alkenoic acid derivatives from F. solani H915 are low in toxicity and are potent antifungal agents against tea pathogenic fungi.

The potential of compounds isolated from Xylaria spp. as antifungal agents against anthracnose

ABSTRACT Anthracnose is a crop disease usually caused by fungi in the genus Colletotrichum or Gloeosporium. These are considered one of the main pathogens, causing significant economic losses, such as in peppers and guarana. The current forms of control include the use of resistant cultivars, sanitary pruning and fungicides. However, even with the use of some methods of controlling these cultures, the crops are not free of anthracnose. Additionally, excessive application of fungicides increases the resistance of pathogens to agrochemicals and cause harm to human health and the environment. In order to find natural antifungal agents against guarana anthracnose, endophytic fungi were isolated from Amazon guarana. The compounds piliformic acid and cytochalasin D were isolated by chromatographic techniques from two Xylaria spp., guided by assays with Colletotrichum gloeosporioides. The isolated compounds were identified by spectrometric techniques, as NMR and mass spectrometry. This is the first report that piliformic acid and cytochalasin D have antifungal activity against C. gloeosporioides with MIC 2.92 and 2.46 µmol mL-1 respectively. Captan and difenoconazole were included as positive controls (MIC 16.63 and 0.02 µmol mL-1, respectively). Thus, Xylaria species presented a biotechnological potential and production of different active compounds which might be promising against anthracnose disease.

Antifungal activities of cytochalasins produced by Diaporthe miriciae, an endophytic fungus associated with tropical medicinal plants.

In the present study, we evaluated the antifungal potential of cytochalasins produced by Diaporthe taxa against phytopathogenic fungi. Using molecular methods, seven endophytic fungal strains from the medicinal plants Copaifera pubiflora and Melocactus ernestii were identified as Diaporthe miriciae, while two isolates were identified to the genus level (Diaporthe sp.). All crude extracts of Diaporthe species produced via solid-state fermentation were evaluated by 1H NMR analyses. Crude extracts of the isolates D. miriciae UFMGCB 6350, 7719, 7646, 7653, 7701, 7772, and 7770 and Diaporthe sp. UFMGCB 7696 and 7720 were demonstrated to produce highly functionalized compounds. The extracts of D. miriciae UFMGCB 7719 and 6350 were selected as representative Diaporthe samples and subjected to bioassay-directed fractionation to isolate cytochalasins H and J. Cytochalasins H and J were evaluated for activities against the fungal plant pathogens Colletotrichum fragariae, Colletotrichum gloeosporioides, Colletotrichum acutatum, Botrytis cinerea, Fusarium oxysporum, Phomopsis obscurans, and Phomopsis viticola using microdilution broth assays. Cytochalasins H and J exhibited the most potent activities against the Phomopsis species tested. Our results showed that Diaporthe species were potential producers of different cytochalasins, which exhibit potential for controlling fungal diseases in planta and (or) maintaining antagonism.

Impact of chitosan based edible coatings functionalized with natural compounds on Colletotrichum fragariae development and the quality of strawberries.

The antifungal effect of chitosan edible coatings (ChEC) functionalized with cinnamon essential oil and aqueous extract of Roselle calyces on Colletotrichum fragariae growth and physical-chemical, physiological and nutraceutical features of strawberries at 5 and 20 °C were evaluated. ChEC was characterized with respect to its water vapor permeability (WVP) and mechanical properties. Results indicated that C. fragariae grew from the third day in strawberries stored at 20 °C, whilst at 5 °C disease symptoms were observed after 10 days in fruit inoculated and treated with ChEC after 24 h. The weight loss was reduced 15 times and firmness was higher by 33% in fruit treated with ChEC and stored at 5 °C. The antioxidant capacity of strawberries increased at the end of the storage only in control group. In conclusion, ChEC can be an effective technology for preserving quality strawberries for 17 days at 5 °C.