Development and validation of a rapid LC-MS/MS method for the quantification of mycosporines and mycosporine-like amino acids (MAAs) from cyanobacteria

Geraldes, Vanessa; Medeiros, Lívia Soman de; Jacinavicius, Fernanda Rios; Long, Paul F.; Pinto, Ernani

doi:10.1016/j.algal.2020.101796

Cited by 27 publications

(35 citation statements)

References 51 publications

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“…UV radiation is one of the most important factors that influences the accumulation of MAA and results in changes in the MAA profile of organisms. MAA synthesis is also affected by spectral variability and intensity [ 31 , 32 ]. Other factors, such as changes in salinity and nutrient availability, stimulate the production of MAAs.…”

Section: Mycosporine-like Amino Acidsmentioning

confidence: 99%

“…This protocol uses only water and volatile additives as the extractor solvents, and the extracts were directly injected to a high-performance liquid chromatograph (HPLC). This extraction protocol is not only easy-to-handle but also uses solvents without certified toxic effects [ 32 ].…”

Section: Mycosporine-like Amino Acidsmentioning

confidence: 99%

“…HPLC was the most common method to separate and identify MAAs by using retention times and UV spectra. Although UV detection is sensitive because of high attenuation coefficients (ε) for MAAs, this method is poor in selectivity, since biosynthetic congeners can easily influence MAA identification [ 32 ]. Moreover, no commercial sources for standard compounds exist and few laboratories worldwide have the capacity to provide reference material against which structural elucidation of MAAs can be verified.…”

Section: Mycosporine-like Amino Acidsmentioning

confidence: 99%

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Mycosporine-Like Amino Acids (MAAs): Biology, Chemistry and Identification Features

Geraldes

Pinto

2021

Pharmaceuticals

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Mycosporines and mycosporine-like amino acids are ultra-violet-absorbing compounds produced by several organisms such as lichens, fungi, algae and cyanobacteria, especially upon exposure to solar ultraviolet radiation. These compounds have photoprotective and antioxidant functions. Mycosporine-like amino acids have been used as a natural bioactive ingredient in cosmetic products. Several reviews have already been developed on these photoprotective compounds, but they focus on specific features. Herein, an extremely complete database on mycosporines and mycosporine-like amino acids, covering the whole class of these natural sunscreen compounds known to date, is presented. Currently, this database has 74 compounds and provides information about the chemistry, absorption maxima, protonated mass, fragments and molecular structure of these UV-absorbing compounds as well as their presence in organisms. This platform completes the previous reviews and is available online for free and in the public domain. This database is a useful tool for natural product data mining, dereplication studies, research working in the field of UV-absorbing compounds mycosporines and being integrated in mass spectrometry library software.

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Section: Mycosporine-like Amino Acidsmentioning

confidence: 99%

Section: Mycosporine-like Amino Acidsmentioning

confidence: 99%

Section: Mycosporine-like Amino Acidsmentioning

confidence: 99%

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Mycosporine-Like Amino Acids (MAAs): Biology, Chemistry and Identification Features

Geraldes

Pinto

2021

Pharmaceuticals

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“…This MAA is a rare mycosporine previously reported by Orfanoudaki et al (2019) as a constituent of red algae and as a shunt product during MAA biosynthesis in a heterologous host (Miyamoto et al 2014). However, MGA had never been reported in a cyanobacterial strain until recently by our group (Geraldes et al 2020).…”

Section: Gene Cluster Identification and Annotationmentioning

confidence: 89%

“…, and 30 mL of suspended cells were irradiated in 25 cm² tissue culture flasks with a hydrophobic filter cap (TP90026, TPP) at a distance of 40 cm with lamps at 24 ± 2°C under light / dark cycle (12 h : 12 h) for 3 days (Singh et al 2008a). Cultures were harvest at the beginning and at the end of the experiment, and MAAs were extracted for subsequent analysis of MAAs using the liquid chromatography-tandem mass spectrometry (LC-MS/MS) method described by Geraldes et al (2020). All the experiment was performed in triplicate.…”

Section: Maas Induction Using Uvrmentioning

confidence: 99%

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

Geraldes¹,

Medeiros²,

Lima³

et al. 2020

ALGAE

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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 / twodimensional 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 ultraviolet 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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Resolving Confusion Surroundingd‐Ala‐d‐Ala Ligase Catalysis in Cyanobacterial Mycosporine‐Like Amino Acid (MAA) Biosynthesis

2023

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Mycosporine-like amino acids (MAAs) are natural UV-absorbing sunscreens that evolved in cyanobacteria and algae to palliate harmful effects from obligatory exposure to solar radiation. Multiple lines of evidence prove that in cyanobacteria all MAAs are derived from mycosporine-glycine, which is typically modified by an ATP-dependent ligase encoded by the gene mysD. The function of the mysD ligase has been experimentally described but haphazardly named based solely upon sequence similarity to the d-alanine-d-alanine ligase of bacterial peptidoglycan biosynthesis. Combining phylogeny and alpha-fold tertiary protein structure prediction unambiguously distinguished mysD from d-alanine-d-alanine ligase. The renaming of mysD to mycosporine-glycine-amine ligase (MG-amine ligase) using recognised enzymology rules of nomenclature is, therefore, proposed, and considers relaxed specificity for several different amino acid substrates. The evolutionary and ecological context of MG-amine ligase catalysis merits wider appreciation especially when considering exploiting cyanobacteria for biotechnology, for example, producing mixtures of MAAs with enhanced optical or antioxidant properties.

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Development and validation of a rapid LC-MS/MS method for the quantification of mycosporines and mycosporine-like amino acids (MAAs) from cyanobacteria

Cited by 27 publications

References 51 publications

Mycosporine-Like Amino Acids (MAAs): Biology, Chemistry and Identification Features

Mycosporine-Like Amino Acids (MAAs): Biology, Chemistry and Identification Features

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

Resolving Confusion Surroundingd‐Ala‐d‐Ala Ligase Catalysis in Cyanobacterial Mycosporine‐Like Amino Acid (MAA) Biosynthesis

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