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Efficient Isolation of Mycosporine-Like Amino Acids from Marine Red Algae by Fast Centrifugal Partition Chromatography

Marine rhodophyta are known to synthesize specific secondary metabolites, mycosporine-like amino acids (MAAs), to protect themselves from harmful UV-radiation. Shinorine and porphyra-334 are among the most abundant representatives of this compound class. In the present work, a novel approach for the...

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Autores principales: Zwerger, Michael, Schwaiger, Stefan, Ganzera, Markus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8879178/
https://www.ncbi.nlm.nih.gov/pubmed/35200636
http://dx.doi.org/10.3390/md20020106
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author Zwerger, Michael
Schwaiger, Stefan
Ganzera, Markus
author_facet Zwerger, Michael
Schwaiger, Stefan
Ganzera, Markus
author_sort Zwerger, Michael
collection PubMed
description Marine rhodophyta are known to synthesize specific secondary metabolites, mycosporine-like amino acids (MAAs), to protect themselves from harmful UV-radiation. Shinorine and porphyra-334 are among the most abundant representatives of this compound class. In the present work, a novel approach for their isolation is described. As a first step, a fast centrifugal partition chromatography method, with an aqueous two-phase system comprising water, ethanol, ammonium sulfate and methanol in ascending mode, was developed to isolate the two MAAs from crude aqueous-methanolic extracts of three algal species within 90 min. The compounds could be isolated when just one of them was present in a sample or also both at the same time. By employing solid phase extraction as a second purification step, the individual MAAs were obtained in high purity and good quantity within a much shorter time frame than the established purification protocols, e.g., semi-preparative HPLC. For example, from 4 g Porphyra sp. (Nori) crude extract, 15.7 mg shinorine and 36.2 mg porphyra-334 were isolated. Both were highly pure, as confirmed by TLC, HPLC-MS and NMR analyses.
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spelling pubmed-88791782022-02-26 Efficient Isolation of Mycosporine-Like Amino Acids from Marine Red Algae by Fast Centrifugal Partition Chromatography Zwerger, Michael Schwaiger, Stefan Ganzera, Markus Mar Drugs Article Marine rhodophyta are known to synthesize specific secondary metabolites, mycosporine-like amino acids (MAAs), to protect themselves from harmful UV-radiation. Shinorine and porphyra-334 are among the most abundant representatives of this compound class. In the present work, a novel approach for their isolation is described. As a first step, a fast centrifugal partition chromatography method, with an aqueous two-phase system comprising water, ethanol, ammonium sulfate and methanol in ascending mode, was developed to isolate the two MAAs from crude aqueous-methanolic extracts of three algal species within 90 min. The compounds could be isolated when just one of them was present in a sample or also both at the same time. By employing solid phase extraction as a second purification step, the individual MAAs were obtained in high purity and good quantity within a much shorter time frame than the established purification protocols, e.g., semi-preparative HPLC. For example, from 4 g Porphyra sp. (Nori) crude extract, 15.7 mg shinorine and 36.2 mg porphyra-334 were isolated. Both were highly pure, as confirmed by TLC, HPLC-MS and NMR analyses. MDPI 2022-01-27 /pmc/articles/PMC8879178/ /pubmed/35200636 http://dx.doi.org/10.3390/md20020106 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zwerger, Michael
Schwaiger, Stefan
Ganzera, Markus
Efficient Isolation of Mycosporine-Like Amino Acids from Marine Red Algae by Fast Centrifugal Partition Chromatography
title Efficient Isolation of Mycosporine-Like Amino Acids from Marine Red Algae by Fast Centrifugal Partition Chromatography
title_full Efficient Isolation of Mycosporine-Like Amino Acids from Marine Red Algae by Fast Centrifugal Partition Chromatography
title_fullStr Efficient Isolation of Mycosporine-Like Amino Acids from Marine Red Algae by Fast Centrifugal Partition Chromatography
title_full_unstemmed Efficient Isolation of Mycosporine-Like Amino Acids from Marine Red Algae by Fast Centrifugal Partition Chromatography
title_short Efficient Isolation of Mycosporine-Like Amino Acids from Marine Red Algae by Fast Centrifugal Partition Chromatography
title_sort efficient isolation of mycosporine-like amino acids from marine red algae by fast centrifugal partition chromatography
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8879178/
https://www.ncbi.nlm.nih.gov/pubmed/35200636
http://dx.doi.org/10.3390/md20020106
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