First Investigation of Secondary Metabolites from Reveals Compounds with Inhibitive Effects against Three Phytopathogenic Fungi of Agrarian Crops.

Fungal secondary metabolites play a highly significant role in crop protection, which is related to their antifungal activity against agriculturally important phytopathogens. In fact, plant diseases caused by fungi including species belonging to the genera of , , and have become increasingly serious affecting crop yield and quality. Hence, there is increasing awareness by the scientific community of the importance of exploiting fungal products for finding new compounds able to inhibit phytopathogens.

BODIPY-Based Analogue of the TREM2-Binding Molecular Adjuvant Sulfavant A, a Chemical Tool for Imaging and Tracking Biological Systems.

Recently, we described synthetic sulfolipids named Sulfavants as a novel class of molecular adjuvants based on the sulfoquinovosyl-diacylglycerol skeleton. The members of this family, Sulfavant A (), Sulfavant R (), and Sulfavant S (), showed important effects on triggering receptor expressed on myeloid cells 2 (TREM2)-induced differentiation and maturation of human dendritic cells (hDC), through a novel cell mechanism underlying the regulation of the immune response. As these molecules are involved in biological TREM2-mediated processes crucial for cell survival, here, we report the synthesis and application of a fluorescent analogue of Sulfavant A bearing the 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza--indacene moiety (Me-BODIPY).

In Vitro Evaluation of Antiviral Activities of Funicone-like Compounds Vermistatin and Penisimplicissin against Canine Coronavirus Infection.

Recent studies have demonstrated that 3--methylfunicone (OMF), a fungal secondary metabolite from belonging to the class of funicone-like compounds, has antiviral activity against canine coronaviruses (CCoV), which causes enteritis in dogs. Herein, we selected two additional funicone-like compounds named vermistatin (VER) and penisimplicissin (PS) and investigated their inhibitory activity towards CCoV infection. Thus, both compounds have been tested for their cytotoxicity and for antiviral activity against CCoV in A72 cells, a fibrosarcoma cell line suitable for investigating CCoV.

Exploring the Binding of Natural Compounds to Cancer-Related G-Quadruplex Structures: From 9,10-Dihydrophenanthrenes to Their Dimeric and Glucoside Derivatives.

In-depth studies on the interaction of natural compounds with cancer-related G-quadruplex structures have been undertaken only recently, despite their high potential as anticancer agents, especially due to their well-known and various bioactivities. In this frame, aiming at expanding the repertoire of natural compounds able to selectively recognize G-quadruplexes, and particularly focusing on phenanthrenoids, a mini-library including dimeric (-) and glucoside (-) analogues of 9,10-dihydrophenanthrenes, a related tetrahydropyrene glucoside () along with 9,10-dihydrophenanthrene were investigated here by several biophysical techniques and molecular docking. Compounds and emerged as the most selective G-quadruplex ligands within the investigated series.

Effectiveness of the Fungal Metabolite 3--Methylfunicone towards Canine Coronavirus in a Canine Fibrosarcoma Cell Line (A72).

Canine coronavirus (CCoV), an alphacoronavirus, may cause self-limiting enteric disease in dogs, especially in puppies. The noteworthy plasticity of coronaviruses (CoVs) occurs through mutation and recombination processes, which sometimes generate new dangerous variants. The ongoing SARS-CoV-2 pandemic and the isolation of a novel canine-feline recombinant alphacoronavirus from humans emphasizes the cross-species transmission ability of CoVs.

Interaction of the Fungal Metabolite Harzianic Acid with Rare-Earth Cations (Pr, Eu, Ho, Tm).

Rare-earth elements (REEs) are in all respect a class of new contaminants that may have toxic effects on organisms and microorganisms and information on their interactions with natural ligands should be of value to predict and control their diffusion in natural environments. In the current study, we investigate interactions of tripositive cations of praseodymium, europium, holmium, and thulium with harzianic acid (HL), a secondary metabolite produced by selected strains of fungi belonging to the genus. We applied the same techniques and workflow previously employed in an analogous study concerning lanthanum, neodymium, samarium, and gadolinium tripositive cations.

New Insights into Chemical and Biological Properties of Funicone-like Compounds.

Funicone-like compounds are a homogeneous group of polyketides that, so far, have only been reported as fungal secondary metabolites. In particular, species in the genus seem to be the most typical producers of this group of secondary metabolites. The molecular structure of funicone, the archetype of these products, is characterized by a γ-pyrone ring linked through a ketone group to a α-resorcylic acid nucleus.

Anti-Inflammatory Potential of Compounds Isolated from Tunisian Lichens Species.

The lichen's special symbiotic structure enables it to produce bioactive substances. They have historically been recognized for their aesthetic and medicinal benefits. Furthermore, in recent years, they have performed in various fields, including perfumery, dyeing, and pharmacology due to their rich secondary metabolites.

Hands-on synthesis of furanamides and evaluation of their antimicrobial activity.

Diverse natural and synthetic furan derivatives have shown biological activity. Here, we describe the preparation of benzyl and arylethyl β-furanamides with OH or OMe aryl substituents by an adapted sustainable method from a furoic acid using methyl chloroformate. Symmetric and asymmetric β,β'-furanamides have instead been prepared using azabenzotriazole based catalyst (HATU).

Secondary Metabolites, including a New 5,6-Dihydropyran-2-One, Produced by the Fungus . Aphicidal Activity of the Main Metabolite, Sphaeropsidin A.

An undescribed 5,6-dihydropyran-2-one, namely diplopyrone C, was isolated and characterized from the cultures of an isolate of the fungus recovered from in Algeria. The structure and relative stereostructure of (5,6S,7,9,10)-5-hydroxy-6-(2-(3-methyloxiran-2-yl)vinyl)-5,6-dihydro-2H-pyran-2-one were assigned essentially based on NMR and MS data. Furthermore, ten known compounds were isolated and identified in the same cultures.

Interaction of the Fungal Metabolite Harzianic Acid with Rare-Earth Cations (La, Nd, Sm, Gd).

Rare-earth elements are emerging contaminants of soil and water bodies which destiny in the environment and effects on organisms is modulated by their interactions with natural ligands produced by bacteria, fungi and plants. Within this framework, coordination by harzianic acid (HL), a secondary metabolite, of a selection of tripositive rare-earth cations Ln (Ln = La, Nd, Sm and Gd) was investigated at 25 °C, and in a CHOH/0.1 M NaClO (50/50 ) solvent, using mass spectrometry, circular dichroism, UV-Vis spectrophotometry, and pH measurements.

Direct evidence of the impact of aqueous self-assembly on biological behavior of amphiphilic molecules: The case study of molecular immunomodulators Sulfavants.

Sulfavant A and Sulfavant R, sulfoquinovoside-glycerol lipids under study as vaccine adjuvants, structurally differ only for the configuration of glyceridic carbon, R/S and R respectively. The in vitro activity of these substances follows a bell-shaped dose-response curve, but Sulfavant A gave the best response around 20 µM, while Sulfavant R at 10 nM. Characterization of aqueous self-assembly of these molecules by a multi-technique approach clarified the divergent and controversial biological outcome.

Natural compounds from plants interacting with telomeric and oncogene G-quadruplex structures as potential anticancer agents.

Aiming at discovering novel, putative anticancer drugs featuring low-to-null side effects, natural compounds isolated from were studied here for their ability to target G-quadruplex structures originating from cancer-related telomeric and oncogene DNA sequences. Particularly, various dihydrophenanthrene, benzocoumarin and dihydrodibenzoxepin derivatives were firstly screened by the affinity chromatography-based G4-CPG assay, and the compound with the highest affinity and selectivity for G-quadruplexes (named J10) was selected for further studies. Fluorescence spectroscopy and circular dichroism experiments corroborated its capability to selectively recognize and stabilize G-quadruplexes over duplex DNA, also showing a preference for parallel G-quadruplexes.

Mitidjospirone, a new spirodioxynaphthalene and GC-MS screening of secondary metabolites produced by strains of associated to dieback.

Mitidjospirone, a new spiridioxynaphthalene, was isolated from the mycelial extract of a strain of , a recently described species belonging to the family Botryosphaeriaceae. Its structure was elucidated by extensive spectroscopic analysis and the absolute configuration was determined by electronic circular dichroism (ECD) experiment. Furthermore, several known compounds were identified during the screening of secondary metabolites produced by four strains of .

Ecotoxicity and photodegradation of Montelukast (a drug to treat asthma) in water.

The present work focuses on the ecotoxicological effects of montelukast sodium (MTL) and its photoproducts, obtained under environmentally-like conditions. Despite of the potential presence in surface waters and the common use of MTL as asthma drug, limited data has been published for its photodegradation, while no information is available for its ecotoxicity. Light-induced degradation is an effective way for drugs to degrade in aquatic environments, and MTL is highly photosensitive, even by exposure to sunlight.

A One-Pot Approach to Novel Pyridazine -Nucleosides.

The synthesis of glycosides and modified nucleosides represents a wide research field in organic chemistry. The classical methodology is based on coupling reactions between a glycosyl donor and an acceptor. An alternative strategy for new -nucleosides is used in this approach, which consists of modifying a pre-existent furyl aglycone.

A new cyanine from oxidative coupling of chlorogenic acid with tryptophan: Assessment of the potential as red dye for food coloring.

A red pigment was prepared by reaction of chlorogenic acid (CGA) with tryptophan (TRP) in air at pH 9 (37% w/w yield) and evaluated as food dye. The main component of pigment was formulated as an unusual benzochromeno[2,3-b]indole linked to a TRP unit, featuring a cyanine type chromophore (λ 542, 546 nm, 1% extinction coefficient of the sodium salt = 244 ± 2). The chromophore showed a minimal pH dependence and proved stable for at least 3 h at 90 °C, both at pH 3.

Coordination Properties of the Fungal Metabolite Harzianic Acid toward Toxic Heavy Metals.

Some Trichoderma strains are known for their capacity to produce harzianic acid, a metabolite belonging to the tetramic acid derivatives. Harzianic acid has interesting biological properties, such as antimicrobial activities against phytopathogenic fungi and promotion of plant growth. It also possesses remarkable chemical properties, including the chelating properties toward essential transition metals, which might be related to the biological activities.

Synergistic Effect of Abietic Acid with Oxacillin against Methicillin-Resistant .

Resin acids are valued in traditional medicine for their antiseptic properties. Among these, abietic acid has been reported to be active against methicillin-resistant (MRSA) strains. In veterinary healthcare, the methicillin-resistant (MRSP) strain is an important reservoir of antibiotic resistance genes including .

Physiological and Oxidative Stress Responses of Lettuce to Cleomside A: A Thiohydroximate, as a New Allelochemical from L.

The inclination toward natural products have led the onset for the discovery of new bioactive metabolites that could be targeted for specific therapeutic or agronomic applications. This study aimed to isolate bioactive compounds from L., and subsequently determine the unexplored mechanism of action of the newly identified compounds on L.

Novel Antimicrobial Peptide from Temporin L in The Treatment of and in Polymicrobial Inter-Kingdom Infection.

Interkingdom polymicrobial diseases are caused by different microorganisms that colonize the same niche, as in the case of yeast-bacteria coinfections. The latter are difficult to treat due the absence of any common therapeutic target for their elimination, both in animals and humans. and belong to distinct kingdoms.

Synthesis of novel lignan-like compounds and their antimicrobial activity.

Herein we report the preparation of 3,4-dibenzylfurans and some oxidized derivatives with lignan backbone. The compounds were prepared using the Friedel-Crafts reaction with BF etherate as catalyst, demethylation with iodocyclohexane, acetylation and oxidation reactions. The antimicrobial activity was evaluated through their capacity to inhibit the growth of Gram positive and Gram negative bacteria, and of the yeast Candida albicans.

Bivalent Metal-Chelating Properties of Harzianic Acid Produced by Associated to the Gastropod .

Harzianic acid is a secondary metabolite of , structurally belonging to the dienyltetramic acid subgroup of the tetramic acids. Biological activities of harzianic acid are of great interest for its antimicrobial and plant growth-promoting activities, which might be related to its chelating properties. In the present work harzianic acid, isolated from cultures of a strain of associated to the gastropod , was studied as a complexant agent of a number of biologically relevant transition metals (i.

Identification of the Main Metabolites of a Marine-Derived Strain of Using LC and GC MS Techniques.

Marine-derived fungi are an important source of many valuable compounds with original structures and diverse physico-chemical properties. In this work, the metabolomic profile of a strain of , recovered from a snakelocks sea anemone (), was investigated through the parallel application of LC-ESI-HRMS, GC-MS, and NMR. Our strategy allowed the identification of mycophenolic acid, brevianamide A, and several compounds belonging to the thiosilvatins.