Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Fungi and plants are rich sources of thousands of secondary metabolites. The genetically coded possibilities for secondary metabolite production, the stimuli of the production, and the special phytotoxins basically determine the microscopic fungi-host plant interactions and the pathogenic lifestyle of fungi. The review introduces plant secondary metabolites usually with antifungal effect as well as the importance of signaling molecules in induced systemic resistance and systemic acquired resistance processes. The review also concerns the mimicking of plant effector molecules like auxins, gibberellins and abscisic acid by fungal secondary metabolites that modulate plant growth or even can subvert the plant defense responses such as programmed cell death to gain nutrients for fungal growth and colonization. It also looks through the special secondary metabolite production and host selective toxins of some significant fungal pathogens and the plant response in form of phytoalexin production. New results coming from genome and transcriptional analyses in context of selected fungal pathogens and their hosts are also discussed.

/pdf/secondary-metabolites-in-fungus-plant-interactions-15rnaz4vmj.pdf

Secondary metabolites in fungus-plant interactions

3‐Alkenyl‐oxindoles: Natural Products, Pharmaceuticals, and Recent Synthetic Advances in Tandem/Telescoped Approaches

Advances in dearomatization strategies of indoles

Drug-lead synthesis through rapid construction of chiral molecular complexity around the biologically relevant framework using a highly efficient strategy is a key goal of organic synthesis. Molecules bearing a spirooxindole-type framework exhibit important bioactivities. Herein, we present a highly efficient and convenient strategy that allows rapid construction of unique optically active spiro[oxazoline-3,3'-oxindole]s through the organocatalyzed asymmetric synthesis of spirocyclic thiocarbamates via an aldol reaction. Preliminary biological evaluation of several of the spirooxazolines using a model of acute neuroinflammation revealed promising antipyretic activity and provided an opportunity to discover new antipyretic agents.

A unique approach to the concise synthesis of highly optically active spirooxazolines and the discovery of a more potent oxindole-type phytoalexin analogue

Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: structures, syntheses and antifungal activity.

The isolation, structure determination, total synthesis and antifungal activity of erucalexin, a novel phytoalexin produced by the wild crucifer dog mustard are described. Erucalexin is a structurally unique plant alkaloid, representing the first example of a spiro[2H-indole-2,5′(4′H)-thiazol]-3-one, likely derived from a C-3–C-2 carbon migration in a 3-substituted indolyl nucleus.

Unprecedented chemical structure and biomimetic synthesis of erucalexin, a phytoalexin from the wild crucifer Erucastrum gallicum

Design, synthesis, and antifungal activity of inhibitors of brassilexin detoxification in the plant pathogenic fungus Leptosphaeria maculans.

Brassilexin and sinalexin are among the most potent antifungal phytoalexins produced by crucifer plants. Nonetheless, the crucifer pathogen Leptosphaeria maculans
				(Desm.) Ces. et de Not. (asexual stage Phoma lingam
				(Tode ex Fr.) Desm.) is able to detoxify these phytoalexins. To understand and control these reactions, the elusive brassilexin and sinalexin detoxification pathways in L. maculans were investigated and compared to those of the synthetic derivatives 8-methylbrassilexin and 8-acetylbrassilexin. The chemical structures, syntheses and antifungal activities of the metabolic intermediates, including the most polar metabolite identified thus far, 3-formylindolyl-2-sulfonic acid, were established. Our overall findings suggest that the first detoxification step of brassilexin involves its reductive bioconversion to 3-aminomethyleneindole-2-thione, followed by hydrolysis and oxidation to the water soluble metabolite 3-formylindolyl-2-sulfonic acid.

Detoxification pathways of the phytoalexins brassilexin and sinalexin in Leptosphaeria maculans: isolation and synthesis of the elusive intermediate 3-formylindolyl-2-sulfonic acid.

Detection, characterization and identification of crucifer phytoalexins using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry.

Mojmir Suchy

Papers

Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: structures, syntheses and antifungal activity.

Unprecedented chemical structure and biomimetic synthesis of erucalexin, a phytoalexin from the wild crucifer Erucastrum gallicum

Design, synthesis, and antifungal activity of inhibitors of brassilexin detoxification in the plant pathogenic fungus Leptosphaeria maculans.

Detoxification pathways of the phytoalexins brassilexin and sinalexin in Leptosphaeria maculans: isolation and synthesis of the elusive intermediate 3-formylindolyl-2-sulfonic acid.

Detection, characterization and identification of crucifer phytoalexins using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry.