β-Carbolines (βCs) are naturally occurring bioactive alkaloids, whereas α-dicarbonyl compounds are reactive substances generated in foods and in vivo. In this work, L-tryptophan reacted with α-dicarbonyl compounds affording new βcarbolines. Glyoxal afforded 1-hydroxymethyl-β-carboline (HME-βC) and its 3-carboxylic acid, and methylglyoxal afforded 1-(1hydroxyethyl)-β-carboline (HET-βC) and its 3-carboxylic acid. 2), and 1-(1,5-dihydroxypent-3-en-1-yl)-β-carboline (3). The formation of these βCs increased under acidic conditions and with increasing temperature. A mechanism is proposed explaining the conversion of a carbonyl into a hydroxy group based on tautomerism and cyclization to the dihydro-βC-3-COOH intermediates, which were isolated and gave the βCs. These α-dicarbonyl-derived βCs occurred in model reactions of L-tryptophan with fructose or glucose incubated under heating and can be considered as advanced glycation end products (AGEs). They were also present in foods and formed during heating processes. HET-βC appeared in processed foods, reaching up to 309 ng/g, with the highest amount found in dried tomato, fried onion, toasted bread, and Manuka honey. HME-βC was only detected in some foods with lower amounts than HET-βC. HET-βC appeared in foods as a racemic mixture of enantiomers suggesting the same mechanism of formation as the synthetized product. α-Dicarbonyl-derived βCs (HET-βC, HME-βC, and 1a/b-3) occur in foods and food processing and, therefore, they are ingested during diet.
In recent years, food ingredients rich in bioactive compounds have emerged as candidates to prevent excess adiposity and other metabolic complications characteristic of obesity, such as low-grade inflammation and oxidative status. Among them, fungi have gained popularity for their high polysaccharide content and other bioactive components with beneficial activities. Here, we use the C. elegans model to investigate the potential activities of a Grifola frondosa extract (GE), together with the underlying mechanisms of action. Our study revealed that GE represents an important source of polysaccharides and phenolic compounds with in vitro antioxidant activity. Treatment with our GE extract, which was found to be nongenotoxic through a SOS/umu test, significantly reduced the fat content of C. elegans, decreased the production of intracellular ROS and aging–lipofuscin pigment, and increased the lifespan of nematodes. Gene expression and mutant analyses demonstrated that the in vivo anti-obesity and antioxidant activities of GE were mediated through the daf-2/daf-16 and skn-1/nrf-2 signalling pathways, respectively. Taken together, our results suggest that our GE extract could be considered a potential functional ingredient for the prevention of obesity-related disturbances.
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