- Book Chapter
47
- 10.1002/9783527681501.ch15
Mycosporine‐Like Amino Acids (MAAs) in Biological Photosystems
- Mar 07, 2014
- Stéphane La Barre + 2 more +2
Mycosporine-like amino acids (MAAs) represent a suite of small molecules which have unique ultraviolet-absorbing capacities, based on their common cyclohexenone or cyclohexenimine conjugated arrangements. MAAs also have strong antioxidant properties, and participate in the osmotic equilibrium of the numerous and diverse marine organisms that produce them, especially in photosymbiotic partnerships. In this chapter a historical introduction is provided to the discovery of MAAs, together with details of their primary and secondary functions. Details are also provided of isolation and spectral information, illustrated by pertinent examples, and aspects of biosynthesis and the modulating environmental factors involved in the production and degradation of MAAs. Two contrasting biological models models are described: lichens, which are mostly terrestrial and extremophiles; and shallow-water tropical reef corals, which are marine and stenotolerant; these have one point in common, namely a permanent exposure to direct sunlight. Finally, brief details are provided of the medical, cosmetological and biotechnological applications of these primary metabolites with secondary roles, that were most likely instrumental in the adaptation of early cyanobacterial life forms to surface conditions. Useful practical information for structural chemists is included in an Appendix. Water-soluble and photostable Low-MW compounds (usually less than 400 Da) No proven toxicity Strong anti-UV absorption, especially between λ = 310–340 nm, with molar absorptivities (ε) at around 40 000 l mol−1 cm−1. Widely known as natural sunscreens, they also act as osmolytes and/or antioxidants with secondary metabolite characteristics that are mostly, but not exclusively, aquatic.
Read more