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

Using a high-resolution reverse-phase liquid chromatography method we found that the tissues of the hermatypic coral Pocillopora capitata (collected in Santiago Bay, Mexico) contain a high diversity of primary and secondary mycosporine-like amino acids (MAAs) typical of some reef-building coral spec...

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Bibliographic Details
Published in:Journal of photochemistry and photobiology. B, Biology Biology, 2009-03, Vol.94 (3), p.191-200
Main Authors: Carignan, Mario O., Cardozo, Karina H.M., Oliveira-Silva, Diogo, Colepicolo, Pio, Carreto, José I.
Format: Article
Language:English
Subjects:
Amino Acids
Animals
Anthozoa - chemistry
Corals
Cyclohexanols - isolation & purification
Cyclohexanones - metabolism
Glycine - analogs & derivatives
Glycine - biosynthesis
Glycine - isolation & purification
Glycine - metabolism
HPLC-MS
Mass Spectrometry - methods
Molecular Structure
Mycosporine-like amino acids (MAAs)
Palythine–threonine
Pocillopora capitata
Pocillopora eydouxi
Stylophora pistillata
Threonine - biosynthesis
Threonine - isolation & purification
UV-photoprotective compounds
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Summary:Using a high-resolution reverse-phase liquid chromatography method we found that the tissues of the hermatypic coral Pocillopora capitata (collected in Santiago Bay, Mexico) contain a high diversity of primary and secondary mycosporine-like amino acids (MAAs) typical of some reef-building coral species: mycosporine–glycine, shinorine, porphyra-334, mycosporine–methylamine–serine, mycosporine–methylamine–threonine, palythine–serine, palythine and one additional novel predominant MAA, with an absorbance maximum of 320 nm. Here we document the isolation and characterization of this novel MAA from the coral P. capitata. Using low multi-stage mass analyses of deuterated and non deuterated compounds, high-resolution mass analyses (Time of Flight, TOF) and other techniques, this novel compound was characterized as palythine–threonine. Palythine–threonine was also present in high concentrations in the corals Pocillopora eydouxi and Stylophora pistillata indicating a wider distribution of this MAA among reef-building corals. From structural considerations we suggest that palythine–threonine is formed by decarboxylation of porphyra-334 followed by demethylation of mycosporine–methylamine–threonine.
ISSN:1011-1344
1873-2682
DOI:10.1016/j.jphotobiol.2008.12.001