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Zeitschrift für Naturforschung C

A Journal of Biosciences

Editor-in-Chief: Seibel, Jürgen

Editorial Board: Aigner , Achim / Boland, Wilhelm / Bornscheuer, Uwe / Hoffmann, Klaus

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1865-7125
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Volume 72, Issue 7-8

Issues

3,7-Isoquinoline quinones from the ascidian tunicate Ascidia virginea

Sven T. Possner
  • Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany
  • Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853-1301, USA
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/ Frank C. Schroeder
  • Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853-1301, USA
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/ Hans Tore Rapp
  • Department of Biology and K.G. Jebsen Centre for Deep-Sea Research, University of Bergen, PO Box 7800, N-5020 Bergen, Norway
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/ Volker Sinnwell
  • Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany
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/ Stefan Franke
  • Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany
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/ Wittko Francke
  • Corresponding author
  • Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany, Tel.: (+49) 40 42838-2866
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Published Online: 2017-04-28 | DOI: https://doi.org/10.1515/znc-2017-0012

Abstract

A new isoquinoline quinone system and its iodinated derivatives were isolated from the ascidian tunicate Ascidia virginea Müller 1776 (Phlebobranchia: Ascidiidae). Structures were elucidated by spectroscopic methods and derivatization reactions. Ascidine A (3,7-dihydro-1,8-dihydroxy-4-(4′-hydroxyphenyl)isoquinoline-3,7-dione (1), ascidine B (3,7-dihydro-1,8-dihydroxy-4-(4′-hydroxy-3′-iodophenyl)isoquinoline-3,7-dione (2), and ascidine C (3,7-dihydro-1,8-dihydroxy-4-(4′-hydroxy-3′,5′-diiodophenyl)isoquinoline-3,7-dione (3) represent a novel type of tyrosine-derived alkaloids.

This article offers supplementary material which is provided at the end of the article.

Keywords: Ascidia virginea; iodinated dihydroisoquinoline-3,7-dione; isoquinoline quinone; structure elucidation; tunicate

Dedication: In memoriam Lothar Jaenicke

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About the article

Received: 2017-01-25

Revised: 2017-01-25

Accepted: 2017-02-28

Published Online: 2017-04-28

Published in Print: 2017-07-14


Citation Information: Zeitschrift für Naturforschung C, Volume 72, Issue 7-8, Pages 259–264, ISSN (Online) 1865-7125, ISSN (Print) 0939-5075, DOI: https://doi.org/10.1515/znc-2017-0012.

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