de Medeiros, Livia Soman
Lima, Stella T.
Alvarenga, Danillo Oliveira
Long, Paul F.
Fiore, Marli Fatima
Total Authors: 8
 Univ Sao Paulo, Fac Pharmaceut Sci, BR-05508000 Sao Paulo - Brazil
 Univ Fed Sao Paulo, Dept Chem, BR-04021001 Diadema, SP - Brazil
 Univ Sao Paulo, Ctr Nucl Energy Agr, Piracicaba, SP - Brazil
 Univ Helsinki, Dept Microbiol, Helsinki 00100 - Finland
 Kings Coll London, Fac Life Sci & Med, Inst Pharmaceut Sci, London WC2R 2LS - England
Total Affiliations: 5
Web of Science Citations:
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. (AU)