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http://dx.doi.org/10.4490/algae.2020.35.5.19

Genetic and biochemical evidence for redundant pathways leading to mycosporine-like amino acid biosynthesis in the cyanobacterium Sphaerospermopsis torques-reginae ITEP-024  

Geraldes, Vanessa (Faculty of Pharmaceutical Sciences, University of Sao Paulo)
de Medeiros, Livia Soman (Department of Chemistry, Federal University of Sao Paulo)
Lima, Stella T. (Centre for Nuclear Energy in Agriculture, University of Sao Paulo)
Alvarenga, Danillo Oliveira (Centre for Nuclear Energy in Agriculture, University of Sao Paulo)
Gacesa, Ranko (Institute of Pharmaceutical Science, Faculty of Life Sciences and Medicine, King's College London)
Long, Paul F. (Faculty of Pharmaceutical Sciences, University of Sao Paulo)
Fiore, Marli Fatima (Centre for Nuclear Energy in Agriculture, University of Sao Paulo)
Pinto, Ernani (Faculty of Pharmaceutical Sciences, University of Sao Paulo)
Publication Information
ALGAE / v.35, no.2, 2020 , pp. 177-187 More about this Journal
Abstract
Cyanobacteria have been widely reported to produce a variety of UV-absorbing mycosporine-like amino acids (MAAs). Herein, we reported production of the unusual MAA, mycosporine-glycine-alanine (MGA) in the cyanobacterium Sphaerospermopsis torques-reginae ITEP-024 using a newly developed UHPLC-DAD-MS/HRMS (ultra-high performance liquid chromatography-diode array detection-high resolution tandem mass spectrometry) method. MGA had previously been first identified in a red-algae, but S. torques-reginae strain ITEP-024 is the first cyanobacteria to be reported as an MGA producer. Herein, the chemical structure of MGA is fully elucidated from one-dimensional / two-dimensional nuclear magnetic resonance and HRMS data analyses. MAAs are unusually produced constitutively in S. torques-reginae ITEP-024, and this production was further enhanced following UV-irradiance. It has been proposed that MAA biosynthesis proceeds in cyanobacteria from the pentose phosphate pathway intermediate sedoheptulose 7-phosphate. Annotation of a gene cluster encoded in the genome sequence of S. torques-reginae ITEP-024 supports these gene products could catalyse the biosynthesis of MAAs. However, addition of glyphosate to cultures of S. torques-reginae ITEP-024 abolished constitutive and ultra-violet radiation induced production of MGA, shinorine and porphyra-334. This finding supports involvement of the shikimic acid pathway in the biosynthesis of MAAs by this species.
Keywords
cyanobacteria; mycosporine-glycine-alanine (MGA); mycosporine-like amino acids (MAAs); Sphaerospermopsis torques-reginae; UV-induction;
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