Bright Green Biofluorescence in Sharks Derives from Bromo-Kynurenine Metabolism

Although in recent years there has been an increased awareness of the widespread nature of biofluorescence in the marine environment, the diversity of the molecules responsible for this luminescent phenotype has been mostly limited to green fluorescent proteins (GFPs), GFP-like proteins, and fluorescent fatty acid-binding proteins (FABPs). In the present study, we describe a previously undescribed group of brominated tryptophan-kynurenine small molecule metabolites responsible for the green biofluorescence in two species of sharks and provide their structural, antimicrobial, and spectral characterization. Multi-scale fluorescence microscopy studies guided the discovery of metabolites that were differentially produced in fluorescent versus non-fluorescent skin, as well as the species-specific structural details of their unusual light-guiding denticles. Overall, this study provides the detailed description of a family of small molecules responsible for marine biofluorescence and opens new questions related to their roles in central nervous system signaling, resilience to microbial infections, and photoprotection. [Display omitted] •We describe a new form of biofluorescence from the skin of catsharks•Bromo-tryptophan-kynurenines are biofluorescent and show antimicrobial activities•Specific dermal denticles in the chain catshark act as optical light-guides•This study opens questions related to biological function of shark fluorescence Chemistry; Natural Product Chemistry; Natural Product Discovery