Genetic and biochemical evidence for redundant pathways leading to mycosporine-like amino acid biosynthesis in the cyanobacterium Sphaerospermopsis torques-reginae ITEP-024원문보기
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)
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...
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.
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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제안 방법
Mass spectra were acquired using electrospray ionization in the positive mode over a range of m/z from 50 to 500. The QTOF instrument was operated in scan and Auto tandem mass spectrometry(MS/MS) mode, performing MS/MS experiments on the three most intense ions from each MS survey scan. The chromatogram was monitored at 330 nm (indicative of the MAAs shinorine and porphyra-334) and retention times of eluted peaks were compared shinorine andporphyra-334 standards (kindly provided by Prof.
대상 데이터
Kazuo Yabe. Glyphosate (96%) was purchased from Sigma-Aldrich (St. Louis, MO, USA).
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