Palythine–threonine, a major novel mycosporine-like amino acid (MAA) isolated from the hermatypic coral Pocillopora capitata

Carignan, Mario O.; Cardozo, Karina Helena Morais; Oliveira‐Silva, Diogo; Colepicolo, Pio; Carreto, José I.

doi:10.1016/j.jphotobiol.2008.12.001

Cited by 51 publications

(69 citation statements)

References 55 publications

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“…Coral species such as Pocillopora capitata and Stylophora pistillata and the dinoflagellates Pseudo-nitzschia multiseries, Emiliania huxleyi, and Alexandrium catenella have been shown to contain the MAAs shinorine, mycosporine-methylamine-serine, and palynthine-serine (33,37,38). On the basis of structure and the distribution of MAAs in corals, the biosynthesis of palythine-serine is proposed to occur via the decarboxylation of the serine group on shinorine, resulting in the production mycosporinemethylamine-serine.…”

Section: Discussionmentioning

confidence: 99%

Comparative Profiling and Discovery of Novel Glycosylated Mycosporine-Like Amino Acids in Two Strains of the Cyanobacterium Scytonema cf. crispum

D’Agostino

Javalkote

Mazmouz

et al. 2016

Appl Environ Microbiol

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The mycosporine-like amino acids (MAAs) are a group of small molecules with a diverse ecological distribution among microorganisms. MAAs have a range of physiological functions, including protection against UV radiation, making them important from a biotechnological perspective. In the present study, we identified a putative MAA (mys) gene cluster in two New Zealand isolates of Scytonema cf. crispum (UCFS10 and UCFS15). Homology to "Anabaena-type" mys clusters suggested that this cluster was likely to be involved in shinorine biosynthesis. Surprisingly, high-performance liquid chromatography analysis of S. cf. crispum cell extracts revealed a complex MAA profile, including shinorine, palythine-serine, and their hexose-bound variants. It was hypothesized that a short-chain dehydrogenase (UCFS15_00405) encoded by a gene adjacent to the S. cf. crispum mys cluster was responsible for the conversion of shinorine to palythine-serine. Heterologous expression of MysABCE and UCFS15_00405 in Escherichia coli resulted in the exclusive production of the parent compound shinorine. Taken together, these results suggest that shinorine biosynthesis in S. cf. crispum proceeds via an Anabaena-type mechanism and that the genes responsible for the production of other MAA analogues, including palythine-serine and glycosylated analogues, may be located elsewhere in the genome. IMPORTANCERecently, New Zealand isolates of S. cf. crispum were linked to the production of paralytic shellfish toxins for the first time, but no other natural products from this species have been reported. Thus, the species was screened for important natural product biosynthesis. The mycosporine-like amino acids (MAAs) are among the strongest absorbers of UV radiation produced in nature. The identification of novel MAAs is important from a biotechnology perspective, as these molecules are able to be utilized as sunscreens. This study has identified two novel MAAs that have provided several new avenues of future research related to MAA genetics and biosynthesis. Further, we have revealed that the genetic basis of MAA biosynthesis may not be clustered on the genome. The identification of the genes responsible for MAA biosynthesis is vital for future genetic engineering.

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Section: Discussionmentioning

confidence: 99%

Comparative Profiling and Discovery of Novel Glycosylated Mycosporine-Like Amino Acids in Two Strains of the Cyanobacterium Scytonema cf. crispum

D’Agostino

Javalkote

Mazmouz

et al. 2016

Appl Environ Microbiol

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“…The HPLC method was similar to the one described above, with the exception that trifluoroacetic acid in the mobile phase was replaced by formic acid to optimize ESI as suggested by Carignan et al (2009). A multiple reaction monitoring (MRM) method was developed with ESI in positive mode (gas temperature = 325°C, gas flow = 11 l min −1…”

Section: Sample Analysismentioning

confidence: 99%

Spring production of mycosporine-like amino acids and other UV-absorbing compounds in sea ice-associated algae communities in the Canadian Arctic

Elliott¹,

Mundy²,

Gosselin³

et al. 2015

Mar. Ecol. Prog. Ser.

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Marine phytoplankton are known to produce mycosporine-like amino acids (MAAs) for protection against UV radiation. To assess whether the same strategy applies to sea ice-associated communities, MAAs were measured in algal communities associated with surface melt ponds, sea ice (bottom 3 cm), sea ice−water interface below melt ponds, and underlying seawater in a coastal bay of the Canadian Arctic Archipelago during the spring melt transition from snowcovered to melt pond-covered sea ice. Six UV-absorbing compounds (UVACs) were detected as the spring melt progressed, 3 of which are identified to be shinorine, palythine, and porphyra-334. A fourth UVAC (U1) is most likely palythene. The molecular identities of the other 2 UVACs, U2 and U3, which have an absorption maximum of 363 and 300 nm, respectively, remain to be structurally elucidated. The highest UVAC nominal concentrations were observed in the 3 cm bottom ice under thin snow-covered sites just prior to complete snowmelt. Normalization to chlorophyll a content revealed that the greatest contribution to UV absorption from biota was associated with melt ponds that are exposed to the highest light intensity. These results confirm that Arctic sea ice-associated communities are capable of producing photoprotectants and that spatial and temporal variations in MAA and other UVAC synthesis are affected by snow cover and UV radiation exposure.

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“…Of these MAAs, 15 have been detected in all scleractinian corals (6,17,29,32,47,84,113), including the last MAA discovered, palythine-threonine (17). Up to 12 different MAA compounds have been found in a single coral species, Stylophora pistillata (17,84,87). However, a maximum of 5 different MAAs have been isolated from algal endosymbionts freshly isolated from a coral host or from cultures ( Fig.…”

Section: Maas In Coral-algal Symbiosismentioning

confidence: 99%

Mycosporine-Like Amino Acids from Coral Dinoflagellates

Rosic

Dove

2011

Appl Environ Microbiol

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Coral reefs are one of the most important marine ecosystems, providing habitat for approximately a quarter of all marine organisms. Within the foundation of this ecosystem, reef-building corals form mutualistic symbioses with unicellular photosynthetic dinoflagellates of the genus Symbiodinium. Exposure to UV radiation (UVR) (280 to 400 nm) especially when combined with thermal stress has been recognized as an important abiotic factor leading to the loss of algal symbionts from coral tissue and/or a reduction in their pigment concentration and coral bleaching. UVR may damage biological macromolecules, increase the level of mutagenesis in cells, and destabilize the symbiosis between the coral host and their dinoflagellate symbionts. In nature, corals and other marine organisms are protected from harmful UVR through several important photoprotective mechanisms that include the synthesis of UV-absorbing compounds such as mycosporine-like amino acids (MAAs). MAAs are small (<400-Da), colorless, water-soluble compounds made of a cyclohexenone or cyclohexenimine chromophore that is bound to an amino acid residue or its imino alcohol. These secondary metabolites are natural biological sunscreens characterized by a maximum absorbance in the UVA and UVB ranges of 310 to 362 nm. In addition to their photoprotective role, MAAs act as antioxidants scavenging reactive oxygen species (ROS) and suppressing singlet oxygen-induced damage. It has been proposed that MAAs are synthesized during the first part of the shikimate pathway, and recently, it has been suggested that they are synthesized in the pentose phosphate pathway. The shikimate pathway is not found in animals, but in plants and microbes, it connects the metabolism of carbohydrates to the biosynthesis of aromatic compounds. However, both the complete enzymatic pathway of MAA synthesis and the extent of their regulation by environmental conditions are not known. This minireview discusses the current knowledge of MAA synthesis, illustrates the diversity of MAA functions, and opens new perspectives for future applications of MAAs in biotechnology.In coral reef ecosystems, scleractinian (hard) corals from the phylum Cnidaria build a three-dimensional (3D) calcium carbonate structure similar to a sea forest that provides a habitat for hundreds of thousands of marine species. Reef-building corals have been demonstrated to form mutualistic symbioses with unicellular photosynthetic dinoflagellates of the genus Symbiodinium (63,103). This mutualistic symbiosis between the coral host and their algal endosymbionts is based on the exchange of nutrients, where the coral host provides shelter and carbon, nitrogen, and other inorganic nutrients to their algal symbionts, while symbiotic dinoflagellates supply coral hosts with their photosynthetic metabolites, meeting up to 95% of the coral's energy requirements (34-36, 40, 105, 116). Coral dinoflagellates also have symbiotic relationships with other invertebrates from the phyla Cnidaria, Platyhelminthes, Mollusca, Porifera, and Foram...

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Palythine–threonine, a major novel mycosporine-like amino acid (MAA) isolated from the hermatypic coral Pocillopora capitata

Cited by 51 publications

References 55 publications

Comparative Profiling and Discovery of Novel Glycosylated Mycosporine-Like Amino Acids in Two Strains of the Cyanobacterium Scytonema cf. crispum

Comparative Profiling and Discovery of Novel Glycosylated Mycosporine-Like Amino Acids in Two Strains of the Cyanobacterium Scytonema cf. crispum

Spring production of mycosporine-like amino acids and other UV-absorbing compounds in sea ice-associated algae communities in the Canadian Arctic

Mycosporine-Like Amino Acids from Coral Dinoflagellates

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