Abstract
Natural chromanols and chromenols comprise a family of molecules with enormous structural diversity and biological activities of pharmacological interest. A recently published systematic review described more than 230 structures that are derived from a chromanol ortpd chromenol core. For many of these compounds structure-activity relationships have been described with mostly anti-inflammatory as well as anti-carcinogenic activities. To extend the knowledge on the biological activity and the therapeutic potential of these promising class of natural compounds, we here present a report on selected chromanols and chromenols based on the availability of data on signaling pathways involved in inflammation, apoptosis, cell proliferation, and carcinogenesis. The chromanol and chromenol derivatives seem to bind or to interfere with several molecular targets and pathways, including 5-lipoxygenase, nuclear receptors, and the nuclear-factor “kappa-light-chain-enhancer” of activated B-cells (NFκB) pathway. Interestingly, available data suggest that the chromanols and chromenols are promiscuitively acting molecules that inhibit enzyme activities, bind to cellular receptors, and modulate mitochondrial function as well as gene expression. It is also noteworthy that the molecular modes of actions by which the chromanols and chromenols exert their effects strongly depend on the concentrations of the compounds. Thereby, low- and high-affinity molecular targets can be classified. This review summarizes the available knowledge on the biological activity of selected chromanols and chromenols which may represent interesting lead structures for the development of therapeutic anti-inflammatory and chemopreventive approaches.
Highlights
Chromanols and chromenols are collective terms for about 230 structures derived from photosynthetic organisms like plants, algae, cyanobacteria, fungi, corals, sponges, and tunicates (Birringer et al, 2018)
We selected chromanols and chromenols for which data on anti-inflammatory and anti-carcinogenic effects were available in public databases of the scientific literature
The structures of our interests were tocopherols, tocotrienols, and their respective metabolites as well as structurally related compounds including sargachromanols, sargachromenols, and amplexichromanols
Summary
Chromanols and chromenols are collective terms for about 230 structures derived from photosynthetic organisms like plants, algae, cyanobacteria, fungi, corals, sponges, and tunicates (Birringer et al, 2018). A- and d-T-13′-OH significantly decreased mRNA (29–72% and 87%, respectively) and protein (40–53% and 53%, respectively) expression of iNOS and the production of nitric oxide (56–69% and 49%, respectively) in LPS-stimulated murine RAW264.7 macrophages at a concentration of 10 μM, showing comparable effect sizes independent from the methylation pattern of the chromanol ring system (Ciffolilli et al, 2015; Schmölz et al, 2017). The length of the side-chain is important for the mediation of anti-inflammatory effects Both a-T13′-COOH (5 μM) and d-T-13′-COOH (5 μM) significantly decreased expressions of iNOS and COX-2 mRNAs as well as proteins in murine LPS-stimulated RAW264.7 macrophages (Wallert et al, 2015; Schmölz et al, 2017).
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