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The Korean Society of Phycology (한국조류학회(藻類))
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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)
  • Received : 2019.12.18
  • Accepted : 2020.05.19
  • Published : 2020.06.15
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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.

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References

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