scholarly journals Discovery of Antifungal and Biofilm Preventative Compounds from Mycelial Cultures of a Unique North American Hericium sp. Fungus

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 963 ◽  
Author(s):  
Xun Song ◽  
François Gaascht ◽  
Claudia Schmidt-Dannert ◽  
Christine E. Salomon
Keyword(s):  
Antifungal Activity ◽  
North American ◽  
Edible Mushroom ◽  
Mass Spectrometry Data ◽  
Bioactive Metabolites ◽  
Edible Fungi ◽  
Mycelial Culture ◽  
Bioassay Guided Fractionation ◽  
Pure Compounds ◽  
New Compounds

Edible mushrooms are an important source of nutraceuticals and for the discovery of bioactive metabolites as pharmaceuticals. In this work, the OSMAC (One Strain, Many Active Compounds) approach was used to isolate two new compounds (1 and 2) along with seven known compounds (3–9) from a mycelial culture of a unique North American edible mushroom Hericium sp. The fruiting body was collected in Marine on St. Croix, Minnesota (USA), and mycelial cultures were grown on four different solid and liquid media. Extracts from the mycelial cultures were screened for antimicrobial activity and only the extract from the Cheerios substrate culture exhibited antifungal activity. Bioassay guided fractionation and HPLC analysis were used to isolate nine pure compounds and the structures of the known compounds were established by analysis of the NMR and mass spectrometry data and comparison to published reports. Compound 1 is a new erinacerin alkaloid and 2 is an aldehyde derivative of 4-hydroxy chroman. Four chlorinated orcinol derivatives (3–6), a pyran (7), erinaceolactone (8), and erinacine (9) were identified. Compound 4 showed antifungal activity against C. albicans and C. neoformans (MIC = 31.3–62.5 μg/mL, respectively). Compound 4 also inhibited biofilm formation of C. albicans and C. neoformans at 7.8 μg/mL. These results suggest that mycelial cultures of edible fungi may provide useful, bioactive compounds.

scholarly journals Phytotoxic Lignans from Artemisia arborescens

2018 ◽  
Vol 13 (3) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Andrea Labruzzo ◽  
Charles L. Cantrell ◽  
Alessandra Carrubba ◽  
Abbas Ali ◽  
David E. Wedge ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Lactuca Sativa ◽  
Aerial Part ◽  
Colletotrichum Gloeosporioides ◽  
Methylene Chloride ◽  
Agrostis Stolonifera ◽  
Colletotrichum Acutatum ◽  
Bioassay Guided Fractionation ◽  
Pure Compounds ◽  
Colletotrichum Fragariae

A systematic bioassay-guided fractionation of methylene chloride extracts of the aerial part of Artemisia arborescens was performed in order to identify its phytotoxic compounds Two lignans were isolated, sesamin and ashantin, that inhibited growth of Agrostis stolonifera (bentgrass), a monocot, and Lactuca sativa (lettuce), a dicot, at 1 mg mL–1. In a dose-response screening of these lignans for growth inhibition against Lemna paucicostata (duckweed), ashantin was the most active with an IC50 of ca. 224 μM. The mode of action of these compounds is still unknown. In mosquito larvicidal bioassays the pure compounds sesamin and ashantin did not cause mortality at the highest dose of 125 mg/L against 1-d-old Aedes aegypti larvae. In bioautography bioassays for antifungal activity using Botrytis cinerea, Fusarium oxysporum, Colletotrichum fragariae, Colletotrichum acutatum, and Colletotrichum gloeosporioides, ashantin and sesamin were inactive at 5 μg and were therefore not subjected to additional screening in secondary antifungal assays.

scholarly journals Bioactive Ascochlorin Analogues from the Marine-Derived Fungus Stilbella fimetaria

Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 46
Author(s):  
Karolina Subko ◽  
Sara Kildgaard ◽  
Francisca Vicente ◽  
Fernando Reyes ◽  
Olga Genilloud ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antifungal Activity ◽  
2D Nmr ◽  
Bioactive Metabolites ◽  
Double Bonds ◽  
Relative Configuration ◽  
D 23 ◽  
Fungal Extracts

The marine-derived fungus Stilbella fimetaria is a chemically talented fungus producing several classes of bioactive metabolites, including meroterpenoids of the ascochlorin family. The targeted dereplication of fungal extracts by UHPLC-DAD-QTOF-MS revealed the presence of several new along with multiple known ascochlorin analogues (19–22). Their structures and relative configuration were characterized by 1D and 2D NMR. Further targeted dereplication based on a novel 1,4-benzoquinone sesquiterpene derivative, fimetarin A (22), resulted in the identification of three additional fimetarin analogues, fimetarins B–D (23–25), with their tentative structures proposed from detailed MS/HRMS analysis. In total, four new and eight known ascochlorin/fimetarin analogues were tested for their antimicrobial activity, identifying the analogues with a 5-chloroorcylaldehyde moiety to be more active than the benzoquinone analogue. Additionally, the presence of two conjugated double bonds at C-2′/C-3′ and C-4′/C-5′ were found to be essential for the observed antifungal activity, whereas the single, untailored bonds at C-4′/C-5′ and C-8′/C-9′ were suggested to be necessary for the observed antibacterial activity.

Design, Synthesis and Evaluate In Vitro Antifungal Activity of Novel Benzamide Derivatives

2019 ◽  
Vol 41 (3) ◽  
pp. 549-549
Author(s):  
Xuesong Wang and Xiaorong Tang Xuesong Wang and Xiaorong Tang
Keyword(s):  
Antifungal Activity ◽  
Pathogenic Fungi ◽  
Gibberella Zeae ◽  
Design Synthesis ◽  
Carboxylic Acid Amides ◽  
Almost All ◽  
Negative Controls ◽  
New Compounds ◽  
Benzamide Derivatives

A series of novel benzamide derivatives according to fluopicolide were designed and synthesized following the rule of combination carboxylic acid amides and amines derivatives together. The antifungal activity of the 15 new compounds were evaluated in vitro against five pathogenic fungi, including Sclerotinia sclerotiorum, Gibberella zeae, Rhizoctonia solani, Helminthosporium maydis and Botrytis cinerea. Almost all the structure have not been reported, except compounds 3, 5 and 6. A surprising finding is that all the five tested fungi breed faster than negative controls when supplementary with compound 715 , respectively.

A new furan carboxamide and two potential precursors from a terrestrial streptomycete

2017 ◽  
Vol 72 (3) ◽  
pp. 175-182 ◽  
Author(s):  
Humaira Naureen ◽  
Michel Feussi Tala ◽  
Khaled A. Shaaban ◽  
Mohamed Shaaban ◽  
Anja Schüffler ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Density Functional ◽  
Acid Amide ◽  
Octadecenoic Acid ◽  
Gas Chromatography Mass Spectrometry ◽  
Bioactive Metabolites ◽  
Cytotoxic Activities ◽  
Tetradecanoic Acid ◽  
Vinyl Phenol ◽  
New Compounds

Abstract Three new bioactive metabolites, 1,6-dihydroxy- 2-methyl-heptan-4-one (1), 4-hydroxy-1-(2-methyl-oxiranyl)- pentan-2-one (2), and 2-(2-hydroxy-propyl)-4-methylfuran- 3-carboxylic acid amide (3) were isolated from the terrestrial Streptomyces sp. isolate ANK245, along with the new microbial constituent p-vinylanisol (4a) and the known metabolites p-vinyl-phenol (4b) and phenethyl alcohol. Analysis of the nonpolar part of the extract by gas chromatography/mass spectrometry (GC-MS) provided further evidence for tetradecanoic acid, 9-octadecenoic acid, hexadecanoic acid, 2-methoxy-4-vinylphenol (4c), 4-hydroxy-3-methoxy-benzaldehyde, o-hydroxybiphenyl, and 1,5,9-trimethyl-4,8,13-cyclotetradecatrien-1,3-diol (5). Structures 1–3 of the new compounds were elucidated by nuclear magnetic resonance (NMR) and NMR spectroscopy, but mass spectrometry (MS) techniques and their absolute configuration were determined by density functional theory (DFT) calculations and Mosher derivatisation. Their antimicrobial and cytotoxic activities were evaluated in comparison with the crude bacterial extract.

scholarly journals A Metabolomic Study of Epichloë Endophytes for Screening Antifungal Metabolites

Metabolites ◽  
2022 ◽  
Vol 12 (1) ◽  
pp. 37
Author(s):  
Krishni Fernando ◽  
Priyanka Reddy ◽  
Kathryn M. Guthridge ◽  
German C. Spangenberg ◽  
Simone J. Rochfort
Keyword(s):  
Phytopathogenic Fungi ◽  
Bioactive Metabolites ◽  
Symbiotic Association ◽  
In Planta ◽  
Vitro Assay ◽  
Antifungal Metabolites ◽  
Bioassay Guided Fractionation ◽  
Toxic Alkaloids ◽  
Epichloë Endophytes

Epichloë endophytes, fungal endosymbionts of Pooidae grasses, are commonly utilized in forage and turf industries because they produce beneficial metabolites that enhance resistance against environmental stressors such as insect feeding and disease caused by phytopathogen infection. In pastoral agriculture, phytopathogenic diseases impact both pasture quality and animal production. Recently, bioactive endophyte strains have been reported to secrete compounds that significantly inhibit the growth of phytopathogenic fungi in vitro. A screen of previously described Epichloë-produced antifeedant and toxic alkaloids determined that the antifungal bioactivity observed is not due to the production of these known metabolites, and so there is a need for methods to identify new bioactive metabolites. The process described here is applicable more generally for the identification of antifungals in new endophytes. This study aims to characterize the fungicidal potential of novel, ‘animal friendly’ Epichloë endophyte strains NEA12 and NEA23 that exhibit strong antifungal activity using an in vitro assay. Bioassay-guided fractionation, followed by metabolite analysis, identified 61 metabolites that, either singly or in combination, are responsible for the observed bioactivity. Analysis of the perennial ryegrass-endophyte symbiota confirmed that NEA12 and NEA23 produce the prospective antifungal metabolites in symbiotic association and thus are candidates for compounds that promote disease resistance in planta. The “known unknown” suite of antifungal metabolites identified in this study are potential biomarkers for the selection of strains that enhance pasture and turf production through better disease control.

Bioactive metabolites from new or rare fimicolous fungi with antifungal activity against plant pathogenic fungi

2014 ◽  
Vol 142 (1) ◽  
pp. 61-71 ◽  
Author(s):  
Sabrina Sarrocco ◽  
Stefania Diquattro ◽  
Fabiana Avolio ◽  
Alessio Cimmino ◽  
Grazia Puntoni ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Pathogenic Fungi ◽  
Bioactive Metabolites ◽  
Plant Pathogenic Fungi

scholarly journals New Holostan-type Triterpene Glycosides from the Sea Cucumber Apostichopus Japonicus

2012 ◽  
Vol 7 (11) ◽  
pp. 1934578X1200701 ◽  
Author(s):  
Zenglei Wang ◽  
Wei Gong ◽  
Guoquan Sun ◽  
Hua Tang ◽  
Baoshu Liu ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Sea Cucumber ◽  
Spectroscopic Analysis ◽  
Apostichopus Japonicus ◽  
Triterpene Glycosides ◽  
New Compounds

Two new holostan-type glycosides, holotoxin D1 (1) and 25,26-dihydroxy-holotoxin A1 (2), together with two known analogues, stichlorosides C1 (3) and bivittoside D (4), were isolated from the sea cucumber Apostichopus japonicus Selenka. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis. Glycosides 1 and 3 exhibited potent antifungal activity.

Activity of Armillarisin B in vitro against Plant Pathogenic Fungi

2009 ◽  
Vol 64 (11-12) ◽  
pp. 790-792 ◽  
Author(s):  
Jin-Wen Shen ◽  
Bing-Ji Ma ◽  
Wen Li ◽  
Hai-You Yu ◽  
Ting-Ting Wu ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Methanolic Extract ◽  
Pathogenic Fungi ◽  
2D Nmr ◽  
Spectroscopic Studies ◽  
Gibberella Zeae ◽  
Plant Pathogenic Fungi ◽  
Fruiting Bodies ◽  
Bioassay Guided Fractionation

The methanolic extract of the fruiting bodies of the mushroom Armillariella tabescens was found to show antifungal activity against Gibberella zeae. The active compound was isolated from the fruiting bodies of A. tabescens by bioassay-guided fractionation of the extract and identifi ed as armillarisin B. Armillarisin B eventually corresponds to 2-hydroxy-2- phenylpropanediamide and its structure was confi rmed on the basis of spectroscopic studies including 2D NMR experiments.

2-Hydroxypropyl derivatives of 1,2,3-thiadiazole and 1,2,3-triazole: Synthesis and antifungal activity

2011 ◽  
Vol 83 (3) ◽  
pp. 715-722 ◽  
Author(s):  
Yury Morzherin ◽  
Polina E. Prokhorova ◽  
Dmitry A. Musikhin ◽  
Tatiana V. Glukhareva ◽  
Zhijin Fan
Keyword(s):  
Mass Spectrometry ◽  
Antifungal Activity ◽  
Ir Spectroscopy ◽  
Elemental Analysis ◽  
Antifungal Activities ◽  
Triazole Derivatives ◽  
New Compounds ◽  
Derivatives Of

A series of novel 5-(2-hydroxypropyl)amino-1,2,3-thiadiazole and 5-(2-hydroxy-propyl)sulfanyl-1,2,3-triazole derivatives were designed and synthesized as candidate fungicides. The new compounds were identified by NMR and IR spectroscopy, mass spectrometry, and elemental analysis. Their antifungal activities were evaluated.

scholarly journals Availability of Wild Edible Fungi in La Malinche National Park, Mexico

2014 ◽  
Vol 2014 ◽  
pp. 1-15
Author(s):  
A. Montoya ◽  
A. Kong ◽  
R. Garibay-Orijel ◽  
C. Méndez-Espinoza ◽  
Rodham E. Tulloss ◽  
...  
Keyword(s):  
National Park ◽  
Temporal Frequency ◽  
Edible Mushroom ◽  
Edible Fungi ◽  
Traditional Use ◽  
Mushroom Species ◽  
Transect Line ◽  
Production Values ◽  
La Malinche ◽  
La Malinche National Park

The aim of this paper is to compare edible mushroom availability between the two slopes of La Malinche National Park in central México, and to discuss the possible relation between their availability and traditional use. Eight transects were set up. Samples were collected weekly during the rainy seasons of years 1998–2000. Sixty-one edible mushroom species were collected from a total area of 3200 m2 (0.32 ha). Over the three-year period, the diversity of mushrooms ranged from 21 to 28 taxa per transect line. Sporocarps were produced at a rate from 2.06 to 6.05 kg/401.51 m2. The highest species richness and production values for spatio-temporal frequency were obtained in Southeast slope. Edible mushrooms availability in the Southeast slope showed a strong dominance, driven mainly by Laccaria trichodermophora and Hebeloma mesophaeum. The Southwest slope had more diversified availability in time and space, with the most representative species, being L. trichodermophora. The characteristics of traditional management on each slope determined the differences found.

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