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. 2006 Feb 22;273(1585):451-6.
doi: 10.1098/rspb.2005.3358.

Preservation of hypericin and related polycyclic quinone pigments in fossil crinoids

Klaus Wolkenstein  1 , Jürgen H Gross, Heinz Falk, Heinz F Schöler
Affiliations

Preservation of hypericin and related polycyclic quinone pigments in fossil crinoids

Klaus Wolkenstein et al. Proc Biol Sci. .

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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Figures

Figure 1
Figure 1
Crown of the Middle Triassic crinoid Carnallicrinus carnalli (MB. E. 13), with exceptional preservation of fossil pigments. Freyburg/Unstrut, Germany. Scale bar, 1 cm.
Figure 2
Figure 2
Photomicrograph of a longitudinal section from a columnal of Liliocrinus munsterianus (NMB M 8908), showing organic matter trapped within the carbonate cement that fills the pores of the crinoid skeleton (stereom). Scale bar, 200 μm.
Figure 3
Figure 3
Negative-ion ESI mass spectra of methanol extracts. (a) Sample of Liliocrinus munsterianus, Upper Jurassic, Switzerland. (b) Samples of Carnallicrinus carnalli, Middle Triassic, Germany.
Figure 4
Figure 4
Negative-ion ESI collision-induced dissociation mass spectra of reference compounds and fossil pigments. (a) Fringelite F. (c) Hypericin. (b, d) Corresponding signals from a sample of Carnallicrinus carnalli (Ch 9), Middle Triassic, Germany.
Figure 5
Figure 5
Proposed diagenetic pathway for the degradation of hypericin in fossil crinoids.
See this image and copyright information in PMC

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