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1.
Chem Biodivers ; 18(10): e2100350, 2021 Oct.
Article in English | MEDLINE | ID: mdl-34399029

ABSTRACT

Endophytic fungi are an important class of microorganisms, able to interact with a host plant via a mutualistic mechanism without visible symptoms of the fungal colonization. The synergy between endophytic fungi and their host plant can promote morphological, physiological and biochemical changes through the expression of bioactive metabolites. This work aims to correlate metabolic changes in the Combretum lanceolatum plant metabolome with its endophytic fungi Diaporthe phaseolorum (Dp) and Trichoderma spirale (Ts), and to discover corresponding metabolite-biomarkers, with the principal focus being on its primary metabolism. The 1 H-NMR metabolomic analysis of qualitative and quantitative changes was performed through multivariate statistical analysis and the identification of primary metabolites was achieved on the Madison Metabolomics Consortium Database. The presence of Dp significantly impacted the plant's metabolic pathways, improving the biosynthesis of primary metabolites such as threonine, malic acid and N-acetyl-mannosamine, which are precursors of special metabolites involved in plant self-defence. This work represents a valuable contribution to advanced studies on the metabolic profiles of the interaction of plants with endophytes.


Subject(s)
Ascomycota/metabolism , Combretum/metabolism , Metabolomics , Trichoderma/metabolism , Ascomycota/chemistry , Combretum/chemistry , Proton Magnetic Resonance Spectroscopy , Trichoderma/chemistry
2.
Chem Biodivers ; 18(7): e2100226, 2021 Jul.
Article in English | MEDLINE | ID: mdl-33998137

ABSTRACT

We report the evaluation of chalcone derivatives as photosystem II (PSII) and plant growth inhibitors. Chalcone derivatives were evaluated as PSII inhibitors through Chl a fluorescence measurement. (E)-Chalcone (6a) and (E)-3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (6j) showed the best results, reducing the performance index on absorption basis parameter (PIabs ) by 70 %. Additionally, the decrease of TR0 /RC and ET0 /RC parameters indicates that the chalcone derivatives limited the number of active PSII reaction centers and the amount of trapped energy within them. Compounds 6a and 6j both act as post-emergent herbicides at 50 µM, reducing the root biomass of the Ipomoea grandifolia weed by 72 % and 83 %, respectively, corroborating the fluorescence results. The selectivity against weeds as compared to valuable crops by compounds 6a and 6j were evaluated employing Zea mays and Phaseolus vulgaris plants. In these, our newly synthesized compounds showed no effects on biomass accumulation of roots and aerial parts when compared to the control, providing valuable evidence for the role of these compounds as selective inhibitors of the growth of undesired weeds.


Subject(s)
Chalcones/pharmacology , Growth Inhibitors/pharmacology , Herbicides/pharmacology , Photosystem II Protein Complex/antagonists & inhibitors , Biomass , Chalcones/chemical synthesis , Chalcones/chemistry , Growth Inhibitors/chemical synthesis , Growth Inhibitors/chemistry , Herbicides/chemical synthesis , Herbicides/chemistry , Ipomoea/drug effects , Ipomoea/growth & development , Molecular Structure , Phaseolus/drug effects , Phaseolus/growth & development , Photochemical Processes , Photosystem II Protein Complex/metabolism , Principal Component Analysis , Zea mays/drug effects , Zea mays/growth & development
3.
Org Process Res Dev ; 25(8): 1966-1973, 2021 Aug 20.
Article in English | MEDLINE | ID: mdl-35663840

ABSTRACT

We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.

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