Δ-Keto-acid/hydroxy-lactone isomerization in some lichen depsides, depsidones and diphenyl ethers.

In some compounds in lichens, the carboxylic acid is -substituted by an 2-oxoalkyl chain. This particular structure induces the existence of δ-keto-acid ka or hydroxy-lactone hl isomers, clearly identified by their NMR data and chemical properties, such as dehydration, methylation and behaviour in thermal conditions. Internal hydrogen bonding between the carboxylic acid and substituent in the ' position is proposed as an isomerization modulator: an H-bond acceptor (OCH) leads to ka isomers, whereas hl isomers are obtained with an H-bond donor (OH).

New insights into the Van Krevelen diagram: Automated molecular formula determination from HRMS for a large chemical profiling of lichen extracts.

Introduction: In recent years, LC-MS has become the golden standard for metabolomic studies. Indeed, LC is relatively easy to couple with the soft electrospray ionization. As a consequence, many tools have been developed for the structural annotation of tandem mass spectra.

ASAP-MS and DART-MS as ancillary tools for direct analysis of the lichen metabolome.

Introduction: Lichens contain unique metabolites that most often need to be characterized from a limited amount of material. While thin layer chromatography is still the preferred analysis method for most lichenologists, liquid chromatography gives a deeper insight in the lichen metabolome, but an extractive step is needed before any analysis. Therefore, ambient ionization mass spectrometry (MS) analysis of lichen samples using Atmospheric Solid Analysis Probe (ASAP) and Direct Acquisition in Real Time (DART) techniques is evaluated.

Intramolecular transesterification of depsides yields fluorescent 1H-isochromen-1-ones: Application as a chemical probe for lichen determination.

The reactivity of eight purified depsides obtained from six european lichens and that display as 2-oxoalkyl chain in ortho-position of the ester bond was explored. These depsides were found to lead to 1H-Isochromen-1-ones, which exhibit a distinctive blue fluorescence at 365 nm, in the presence of a 10% aqueous solution of KOH. A mechanistic explanation, involving the formation of an enolate intermediate and intramolecular transesterification, was proposed and validated by DFT.

Novel Antifungal Compounds, Spermine-Like and Short Cyclic Polylactates, Produced by in Yogurt.

was described as endowed with high antifungal activity. Most of the studies associated this activity to the produced organic acids, i.e.