Preservation of hypericin and related polycyclic quinone pigments in fossil crinoids.

Proceedings. Biological Sciences
Klaus WolkensteinHeinz F Schöler

Abstract

The fringelite pigments, a group ofphenanthroperylene quinones discovered in purple coloured specimens of the Upper Jurassic crinoid Liliocrinus, demonstrate exceptional preservation of organic compounds in macrofossils. Here we report the finding of hypericin and related phenanthroperylene quinones in Liliocrinus munsterianus from the original 'Fringeli' locality and in the Middle Triassic crinoid Carnallicrinus carnalli. Our results show that fringelites in fact consist ofhypericin and closely related derivatives and that the stratigraphic range of phenanthroperylene quinones is much wider than previously known. The fossil occurrence of hypericin indicates a polyketide biosynthesis of hypericin-type pigments in Mesozoic crinoids analogous to similar polyketides, which occur in living crinoids. The common presence of a characteristic distribution pattern of the fossil pigments and related polycyclic aromatic hydrocarbons further suggests that this assemblage is the result of a stepwise degradation of hypericin via a general diagenetic pathway.

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Citations

Oct 27, 2010·Proceedings of the National Academy of Sciences of the United States of America·Klaus WolkensteinHeinz Falk
Sep 21, 2007·Photochemistry and Photobiology·Christopher S LobbanJacob W Petrich
Mar 3, 2015·Proceedings of the National Academy of Sciences of the United States of America·Klaus Wolkenstein
Oct 8, 2015·Journal of the American Chemical Society·Klaus WolkensteinChristian Griesinger
Sep 26, 2015·Environmental Science and Pollution Research International·Stuart G Wakeham, Elizabeth A Canuel
Sep 24, 2013·Food Chemistry·Eva Tavčar BenkovićSamo Kreft
Mar 31, 2017·Natural Product Reports·Yunjiang FengRohan A Davis
Jul 1, 2012·European Journal of Organic Chemistry·Carol A MulrooeyMarisa C Kozlowski
Jun 1, 2020·Current Pharmaceutical Design·Patricia Rocha de AraújoMarlus Chorilli
Dec 1, 2009·Journal of Natural Products·Klaus WolkensteinTatsuo Oji

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