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Mar. Drugs 2015, 13(10), 6291-6305; doi:10.3390/md13106291

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
Received: 22 July 2015 / Revised: 24 September 2015 / Accepted: 28 September 2015 / Published: 9 October 2015
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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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