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Open AccessArticle

Analysis of Mycosporine-Like Amino Acids in Selected Algae and Cyanobacteria by Hydrophilic Interaction Liquid Chromatography and a Novel MAA from the Red Alga Catenella repens

1
Institute of Pharmacy, Pharmacognosy, University of Innsbruck, Innrain 80-82, Innsbruck 6020, Austria
2
Division of Biological Chemistry, Biocenter, Medical University of Innsbruck, Innrain 80-82, Innsbruck 6020, Austria
3
Institute of Biological Sciences, Applied Ecology & Phycology, University of Rostock, Albert-Einstein-Str. 3, Rostock 18059, Germany
4
University of Applied Sciences Upper Austria, Stelzhammerstr. 23, Wels 4600, Austria
*
Author to whom correspondence should be addressed.
Academic Editor: Orazio Taglialatela-Scafati
Mar. Drugs 2015, 13(10), 6291-6305; https://doi.org/10.3390/md13106291
Received: 22 July 2015 / Revised: 24 September 2015 / Accepted: 28 September 2015 / Published: 9 October 2015
Mycosporine-like amino acids (MAAs), a group of small secondary metabolites found in algae, cyanobacteria, lichens and fungi, have become ecologically and pharmacologically relevant because of their pronounced UV-absorbing and photo-protective potential. Their analytical characterization is generally achieved by reversed phase HPLC and the compounds are often quantified based on molar extinction coefficients. As an alternative approach, in our study a fully validated hydrophilic interaction liquid chromatography (HILIC) method is presented. It enables the precise quantification of several analytes with adequate retention times in a single run, and can be coupled directly to MS. Excellent linear correlation coefficients (R2 > 0.9991) were obtained, with limit of detection (LOD) values ranging from 0.16 to 0.43 µg/mL. Furthermore, the assay was found to be accurate (recovery rates from 89.8% to 104.1%) and precise (intra-day precision: 5.6%, inter-day precision ≤6.6%). Several algae were assayed for their content of known MAAs like porphyra-334, shinorine, and palythine. Liquid chromatography-mass spectrometry (LC-MS) data indicated a novel compound in some of them, which could be isolated from the marine species Catenella repens and structurally elucidated by nuclear magnetic resonance spectroscopy (NMR) as (E)-3-hydroxy-2-((5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-((2-sulfoethyl)amino)cyclohex-2-en-1-ylidene)amino) propanoic acid, a novel MAA called catenelline. View Full-Text
Keywords: mycosporine-like amino acids; HILIC; LC-MS; validation; quantification; isolation; UV-sunscreen mycosporine-like amino acids; HILIC; LC-MS; validation; quantification; isolation; UV-sunscreen
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Hartmann, A.; Becker, K.; Karsten, U.; Remias, D.; Ganzera, M. Analysis of Mycosporine-Like Amino Acids in Selected Algae and Cyanobacteria by Hydrophilic Interaction Liquid Chromatography and a Novel MAA from the Red Alga Catenella repens. Mar. Drugs 2015, 13, 6291-6305.

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