Abstract

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.

Highlights

  • Mycosporine-Like Amino Acids fromMany marine organisms have developed specific strategies to protect themselves from harmful UV-A and UV-B radiation

  • The first step in the development of any Fast centrifugal partition chromatography (FCPC) method is the selection of an optimal two-phase solvent system

  • The K values of the analytes are relevant; so are those of other matrix compounds which could interfere. To account for these issues, close to 40 different solvent combinations were evaluated for their suitability to isolate mycosporinelike amino acids (MAAs) by FCPC

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Summary

Introduction

Mycosporine-Like Amino Acids fromMany marine organisms have developed specific strategies to protect themselves from harmful UV-A and UV-B radiation. One is to synthesize unique secondary metabolites like MAAs [1,2] They consist of a core cyclohexenone or cyclohexenimine ring, substituted with amino alcohols or amino acids. They are nitrogen rich, have low molecular weight (

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