Bioactive Marine Xanthones: A Review

The marine environment is an important source of specialized metabolites with valuable biological activities. Xanthones are a relevant chemical class of specialized metabolites found in this environment due to their structural variety and their biological activities. In this work, a comprehensive literature review of marine xanthones reported up to now was performed. A large number of bioactive xanthone derivatives (169) were identified, and their structures, biological activities, and natural sources were described. To characterize the chemical space occupied by marine-derived xanthones, molecular descriptors were calculated. For the analysis of the molecular descriptors, the xanthone derivatives were grouped into five structural categories (simple, prenylated, O-heterocyclic, complex, and hydroxanthones) and six biological activities (antitumor, antibacterial, antidiabetic, antifungal, antiviral, and miscellaneous). Moreover, the natural product-likeness and the drug-likeness of marine xanthones were also assessed. Marine xanthone derivatives are rewarding bioactive compounds and constitute a promising starting point for the design of other novel bioactive molecules.

Licorice (Glycyrrhiza glabra, G. uralensis, and G. inflata) and Their Constituents as Active Cosmeceutical Ingredients

The interest in plant extracts and natural compounds in cosmetic formulations is growing. Natural products may significantly improve cosmetics performance since they have both cosmetic and therapeutic-like properties, known as cosmeceutical effects. Glycyrrhiza genus, belonging to the Leguminosae family, comprises more than 30 species, widely distributed worldwide. The rhizomes and roots are the most important medicinal parts currently used in pharmaceutical industries and in the production of functional foods and food supplements. In the last few years, the interest in their potential activities in cosmetic formulations has greatly increased. Glycyrrhiza spp. extracts are widely implemented in cosmetic products for their good whitening effect. The biological effects of Glycyrrhiza extracts are especially ascribable to the occurrence of specialized metabolites belonging to the flavonoid class. This review focuses on the botany and the chemistry of the main investigated Glycyrrhiza spp. (G. glabra, G. uralensis, and G. inflata) along with their cosmeceutical activities categorized as skin anti-aging, photoprotective, hair care, and anti-acne. It has been highlighted how, along with Glycyrrhiza extracts, three main flavonoids namely licochalcone A, glabridin, and dehydroglyasperin C are the most investigated compounds. It is noteworthy that other molecules from licorice show potential cosmeceutical effects. These data suggest further investigations to clarify their potential value for cosmetic industries.

Systematic Analysis of the R2R3-MYB Family in Camellia sinensis: Evidence for Galloylated Catechins Biosynthesis Regulation

The R2R3-MYB transcription factor (TF) family regulates metabolism of phenylpropanoids in various plant lineages. Species-expanded or specific MYB TFs may regulate species-specific metabolite biosynthesis including phenylpropanoid-derived bioactive products. Camellia sinensis produces an abundance of specialized metabolites, which makes it an excellent model for digging into the genetic regulation of plant-specific metabolite biosynthesis. The most abundant health-promoting metabolites in tea are galloylated catechins, and the most bioactive of the galloylated catechins, epigallocatechin gallate (EGCG), is specifically relative abundant in C. sinensis. However, the transcriptional regulation of galloylated catechin biosynthesis remains elusive. This study mined the R2R3-MYB TFs associated with galloylated catechin biosynthesis in C. sinensis. A total of 118 R2R3-MYB proteins, classified into 38 subgroups, were identified. R2R3-MYB subgroups specific to or expanded in C. sinensis were hypothesized to be essential to evolutionary diversification of tea-specialized metabolites. Notably, nine of these R2R3-MYB genes were expressed preferentially in apical buds (ABs) and young leaves, exactly where galloylated catechins accumulate. Three putative R2R3-MYB genes displayed strong correlation with key galloylated catechin biosynthesis genes, suggesting a role in regulating biosynthesis of epicatechin gallate (ECG) and EGCG. Overall, this study paves the way to reveal the transcriptional regulation of galloylated catechins in C. sinensis.

Neglected Potential of Wild Garlic (Allium ursinum L.)—Specialized Metabolites Content and Antioxidant Capacity of Wild Populations in Relation to Location and Plant Phenophase

Wild garlic (Allium ursinum L.) is one of the species widely distributed in Europe and Asia and is often nutritionally neglected, characterized by a high content of various phytochemicals with high therapeutic potential and a range of biological activities. The aim of this study was to determine the content of bioactive compounds in the leaves of wild garlic populations collected from different micro-locations, and to determine the differences in the content of phytochemicals in the vegetative and generative phases. A significant content of different specialized metabolites was detected in all analyzed leaves of wild garlic populations regardless of the different factors (location and phenophase): vitamin C content with the highest determined value of 63.31 mg/100 g fw; total phenolic content with the highest determined value of 186.18 mg GAE/100 g fw (according to gallic acid in fresh sample); and antioxidant capacity with the highest determined value of 2230.66 µmol TE/L (according to Trolox). Significant differences in all the phytochemicals analyzed were observed depending on both the location and phenophase of the plants, with the most pronounced differences depending on the phenophase. Thus, lower levels of polyphenolic compounds and vitamin C were generally observed before the flowering phase, while the trend toward higher levels of pigment compounds was observed during the flowering phase of the plants. The results suggest that the leaves of wild garlic can be considered a valuable source of a variety of specialized metabolites with high antioxidant capacity, and thus have high production potential for various functional products and food supplements of natural origin, which are important for the promotion of human health.

Selection for seed size has uneven effects on specialized metabolite abundance in oat (Avena sativa L)

Plant breeding strategies to optimize metabolite profiles are necessary to develop health-promoting food crops. In oats (Avena sativa L.), seed metabolites are of interest for their antioxidant properties, yet have not been a direct target of selection in breeding. In a diverse oat germplasm panel spanning a century of breeding, we investigated the degree of variation of these specialized metabolites and how it has been molded by selection for other traits, like yield components. We also ask if these patterns of variation persist in modern breeding pools. Integrating genomic, transcriptomic, metabolomic and phenotypic analyses for three types of seed specialized metabolites – avenanthramides, avenacins, and avenacosides – we found reduced heritable genetic variation in modern germplasm compared to diverse germplasm, in part due to increased seed size associated with more intensive breeding. Specifically, we found that abundance of avenanthramides increases with seed size, but additional variation is attributable to expression of biosynthetic enzymes. In contrast, avenacoside abundance decreases with seed size and plant breeding intensity. In addition, these different specialized metabolites do not share large-effect loci. Overall, we show that increased seed size associated with intensive plant breeding has uneven effects on the oat seed metabolome, but variation also exists independently of seed size to use in plant breeding. This work broadly contributes to our understanding of how plant breeding has influenced plant traits and tradeoffs between traits (like growth and defense) and the genetic bases of these shifts.

Plant Response to Mechanically-Induced Stress: A Case Study on Specialized Metabolites of Leafy Vegetables

Plants have evolved various adaptive mechanisms to environmental stresses, such as sensory mechanisms to detect mechanical stimuli. This plant adaptation has been successfully used in the production practice of leafy vegetables, called mechanical conditioning, for many years, but there is still a lack of research on the effects of mechanically-induced stress on the content of specialized metabolites, or phytochemicals with significant antioxidant activity. Therefore, the aim of this study was to determine the content of specialized metabolites and antioxidant capacity of lettuce and green chicory under the influence of mechanical stimulation by brushing. Mechanically-induced stress had a positive effect on the content of major antioxidants in plant cells, specifically vitamin C, total phenols, and flavonoids. In contrast, no effect of mechanical stimulation was found on the content of pigments, total chlorophylls, and carotenoids. Based on the obtained results, it can be concluded that induced mechanical stress is a good practice in the cultivation of leafy vegetables, the application of which provides high quality plant material with high nutritional potential and significantly higher content of antioxidants and phytochemicals important for human health.