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Planta Med 1977; 32(5): 33-45
DOI: 10.1055/s-0028-1097555
© Georg Thieme Verlag Stuttgart · New York

FUCOPHLORETHOLE, POLYHYDROXYOLIGOPHENYLÄTHER AUS FUCUS VESICULOSUS1

Fucophloretholes, Polyhydroxyoligophenyl ethers from Fucus vesiculosusK.–W. Glombitza1 , H.–W. Rauwald1 , G. Eckhardt2
  • 1Institut für Pharmazeutische Biologie der Universität Bonn
  • 2Institut für Organische Chemie und Biochemie, MS–Labor, Bonn
1 XVIII. Mitteilung: Antibiotica aus Algen; XVII. Mitteilung: GLOMBITZA, K.-W., KOCH, M. und ECKHARDT, G.: Phytochemistry - im Druck.
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Publication Date:
13 January 2009 (online)

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Abstract

From the fraction of acetylated phenols the following substances have been isolated and characterized in Fucus vesiculosus:

Fucophlorethol–A–octaacetate (2,2',4',6,6'-pentaacetoxy–4–(2,4,6–triacet-oxyphenoxy)-biphenyl), Fucodiphlorethol–A–decaacetate (2,2',4',6,6'-pentaacetoxy–4–[2,6–diacet-oxy–4–(2,4,6–triacetoxyphenoxy)-phenoxy]-biphenyl) and Fucotriphlorethol dodecaacetate (2,2' ,4' ,6,6'-pentaacetoxy–4–(2,6–diacet-oxy–4–[2,6–diacetoxy–4–(2,4,6–triacetoxyphenoxy)-phenoxy]-phenoxy}-biphenyl).

The presence of a difucophlorethol undecaacetate and of a fucophlorethol tetradecaacetate were made presumable. It has been proven by spectra correlation that the structure principles of these substances are also valid for the mixture of lower and higher molecular oligomeres.

The spectral data have been interpreted by comparison with the spectra of a large amount of similarly substituted diphenyl ethers, biphenyls, of phenoxy-biphenyls respectively.

From a great number of similar synthetic methods, the highest yield of o,o'-disubstituted biphenyls was achieved by the method of Cadogan [1].