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Extracellular secretion of phenolic substances from living brown algae

Abstract

The chemical structures of ultraviolet (UV)- absorbing substances secreted from the healthy living brown algae, Eisenia bicyclis and Ecklonia kurome, were demonstrated. The living activity of algal cells was critically examined using a confocal laser-scanning microscope after incorporation of fluorescein diacetate (FDA) into the cells. Using thin-layer chromatography (TLC), reversed-phase three-dimensional high-performance liquid chromatography (RP-3D-HPLC) and gas chromatography-mass spectrometry (GC-MS), it was found that the UV-absorbing substances (λmax 265–270 nm) secreted from the living brown algae mainly consisted of the three monomeric bromophenols, 2,4-dibromophenol, 2,4,6-tribromophenol and dibromo-iodophenol, but not phloroglucinol or phlorotannins. The other minor compounds detected in the secretions were as follows: benzothiazole, fatty acids (14:1, 16:0 and 18:0 acids), franesol, 3-hydroxy-2,4,4-trimethylpentyl 2-methylpropanoate and squalene. Exudation of phloroglucinol and phlorotannins was ascertained to take place only after the cell death of these algae. These results indicate that, whilst the algae are alive, polymeric phlorotannins are strictly kept within the algal body, and only monomeric bromophenols are secreted into the seawater medium.

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Abbreviations

FDA:

fluorescein diacetate

GC-MS:

gas chromatography-mass spectrometry

TLC:

thin-layer chromatography

RP-3D-HPLC:

reversed-phase three-dimensional high-performance liquid chromatography

UV:

ultraviolet

UV-VIS:

ultraviolet-visible

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Correspondence to Toshiyuki Shibata.

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Shibata, T., Hama, Y., Miyasaki, T. et al. Extracellular secretion of phenolic substances from living brown algae. J Appl Phycol 18, 787–794 (2006). https://doi.org/10.1007/s10811-006-9094-y

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Keywords

  • Bromophenols
  • Ecklonia kurome
  • Eisenia bicyclis
  • Gas chromatography-mass spectrometry
  • Phlorotannins
  • Thin-layer chromatography