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Natural Product Molecular Fossils

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Book cover Progress in the Chemistry of Organic Natural Products

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 104))

Abstract

The natural products synthesized by organisms that were living a long time ago gave rise to their molecular fossils. These can consist of either the original unchanged compounds or they may undergo peripheral transformations in which their skeletons remain intact. In cases when molecular fossils can be traced to their organismic source, they are termed “geological biomarkers”.

This contribution describes apolar and polar molecular fossils and, in particular biomarkers, along the lines usually followed in organic chemistry textbooks, and points to their bioprecursors when available. Thus, the apolar compounds are divided in linear and branched alkanes followed by alicyclic compounds and aromatic and heterocyclic molecules, and, in particular, the geoporphyrins. The polar molecular fossils contain as functional groups or constituent units ethers, alcohols, phenols, carbonyl groups, flavonoids, quinones, and acids, or are polymers like kerogen, amber, melanin, proteins, or nucleic acids. The final sections discuss the methodology used and the fundamental processes encountered by the biomolecules described, including diagenesis, catagenesis, and metagenesis.

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Acknowledgments

We are grateful to Dr. Vera Hammer (head of the Mineral Collection of the Museum of Natural History, Vienna, Austria) for her assistance with organic minerals, ambers, and their photographs, to Prof. Norbert Vávra (University Vienna) for “amber help”, to Dr. Melinda Mayer, Kathryn Cross (Inst. of Food Res., Norwich, UK), and Dr. Benjamin Stegmann (University of Ulm), Dr. Mercedes di Pasquo (National Research Council of Argentinia, Laboratorio de Palinología y Paleobotánica, Entre Rios, Argentina), Michael Plewka (Gevelsberg, Germany, plingfactory.de), Richard Robinson (Underwater Photographer, Auckland, New Zealand, www.depth.co.nz), Dr. Jeremy R. Young (UCL, London, UK), and Dr. Klaus Wenderoth (Ebsdorfergrund, Germany) for permission to use their photographs as indicated in the respective Figures. We are also grateful to Dr. Christoph Etzlstorfer (JKU, Linz) for his help with computations.

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  1. Institute of Organic Chemistry, Johannes Kepler University, Altenbergerstraße 69, 4040, Linz, Austria

    Heinz Falk

  2. Department of NMR Based Structural Biology, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077, Göttingen, Germany

    Klaus Wolkenstein

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Editors and Affiliations

  1. Division of Medicinal Chemistry & Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, USA

    A. Douglas Kinghorn

  2. Institute of Organic Chemistry, Johannes Kepler University Linz, Linz, Austria

    Heinz Falk

  3. Research Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, London, UK

    Simon Gibbons

  4. Graduate School of Pharmaceutical Science, Hokkaido University, Sapporo, Japan

    Jun’ichi Kobayashi

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Falk, H., Wolkenstein, K. (2017). Natural Product Molecular Fossils. In: Kinghorn, A.D., Falk, H., Gibbons, S., Kobayashi, J. (eds) Progress in the Chemistry of Organic Natural Products. Progress in the Chemistry of Organic Natural Products, vol 104. Springer, Cham. https://doi.org/10.1007/978-3-319-45618-8_1

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