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

Author(s)

Geraldes, Vanessa ^[1] ; de Medeiros, Livia Soman ^[2] ; Lima, Stella T. ^[3] ; Alvarenga, Danillo Oliveira ^{[3, 4]} ; Gacesa, Ranko ^[5] ; Long, Paul F. ^{[1, 5]} ; Fiore, Marli Fatima ^[3] ; Pinto, Ernani ^{[1, 3]}

Affiliation

^[1] Univ Sao Paulo, Fac Pharmaceut Sci, BR-05508000 Sao Paulo - Brazil

^[2] Univ Fed Sao Paulo, Dept Chem, BR-04021001 Diadema, SP - Brazil

^[3] Univ Sao Paulo, Ctr Nucl Energy Agr, Piracicaba, SP - Brazil

^[4] Univ Helsinki, Dept Microbiol, Helsinki 00100 - Finland

^[5] Kings Coll London, Fac Life Sci & Med, Inst Pharmaceut Sci, London WC2R 2LS - England

• Document type: Journal article
• Source: ALGAE; v. 35, n. 2, p. 177-187, JUN 2020.
• Web of Science Citations: 2

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. (AU)

• FAPESP's process: 14/50420-9 - Secondary metabolites from aquatic microrganisms and their impact on seafood and freshwater fish aquaculture
• Grantee: Ernani Pinto Junior
• Support Opportunities: Regular Research Grants
• FAPESP's process: 15/22742-4 - Identification of new bioactive secondary metabolites from microalgae by integrated analytical approaches
• Grantee: Lívia Soman de Medeiros
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 18/01563-2 - Investigating the secondary metabolism of Brasilonema (Cyanobacteria: Scytonemataceae)
• Grantee: Danillo Oliveira de Alvarenga
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor