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Falk Heinz - Progress in the chemistry of organic natural products. Volume 104

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Falk Heinz Progress in the chemistry of organic natural products. Volume 104

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The first 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. The second contribution covers the distribution of phthalides in nature and the findings in the structural diversity, chemical reactivity, biotransformations, syntheses, and bioactivity of natural and semisynthetic phthalides.;Natural product molecular fossils -- Phthalides: distribution in nature, chemical reactivity, synthesis, and biological activity.

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Springer International Publishing AG 2017
A. Douglas Kinghorn , Heinz Falk , Simon Gibbons and Jun'ichi Kobayashi (eds.) Progress in the Chemistry of Organic Natural Products 104 Progress in the Chemistry of Organic Natural Products 10.1007/978-3-319-45618-8_1
Natural Product Molecular Fossils
Heinz Falk 1
(1)
Institute of Organic Chemistry, Johannes Kepler University, Altenbergerstrae 69, 4040 Linz, Austria
(2)
Department of NMR Based Structural Biology, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Gttingen, Germany
Heinz Falk (Corresponding author)
Email:
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Klaus Wolkenstein (Corresponding author)
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Keywords
Molecular fossils Geological biomarkers Apolar compounds Alkanes Aromatic compounds Heterocyclic compounds Geoporphyrins Ethers Alcohols Phenols Carbonyl compounds Flavonoids Quinones Acids Geopolymers Kerogen Amber Diagenesis
Heinz Falk has been Professor Emeritus at the Institute of Organic Chemistry of - photo 1
Heinz Falk
has been Professor Emeritus at the Institute of Organic Chemistry of the Johannes Kepler University, Linz, Austria since 2007. He studied chemistry at the University of Vienna starting in 1959 and completed his dissertation in organometallic chemistry in 1966. In 1971, he spent a postdoctoral year at ETH Zrich in the laboratory of Albert Eschenmoser. Upon his return to Vienna in 1972 he attained the Habilitation in Organic Chemistry at the University of Vienna. Starting in 1966 he served as an assistant at the Institute of Organic Chemistry at the University of Vienna before being promoted to Associate Professor of Physical Organic Chemistry in 1975. In 1979, he became Full Professor of Organic Chemistry at the Johannes Kepler University of Linz, where he founded the Institute of Organic Chemistry, serving in this chair position for 28 years. From 1989 through 1991, he was Dean of the Faculty of Engineering and Natural Sciences.
Falks main research area is the structural analysis, synthesis, stereochemistry, and photochemistry of plant and animal photosensitizing and photosensory pigments. Besides fundamental studies of the chemistry of bile pigments, the main group of compounds covered in his work are pigments derived from the fundamental phenanthro[1,10,9,8- opqra ]perylene-7,14-dione chromophore inclusive of natural pigments like hypericin. Furthermore, he has pursued research on applied problems of industrial relevance, including oxidation, ozonization, non-natural amino acids, and catalysis. During the course of his career, he has supervised nearly one hundred doctoral students and several postdoctoral students. He has published two books: (1978) Ausgewhlte bungsbeispiele. Zur Nomenklatur Organischer Verbindungen. Springer-Verlag, Wien New York; ISBN 3211814795, and (1989) The Chemistry of Linear Oligopyrroles and Bile Pigments. Springer-Verlag, Wien New York; ISBN 3211821120. He has published about 300 papers and has several patents.
Dr. Falk has served as Editor-in-Chief of Monatshefte fr Chemie/Chemical Monthly for a decade and as series Editor of Progress in the Chemistry of Organic Natural Products since 1998. He is, in addition to his memberships in the American, Austrian, and German Chemical Societies and the New York Academy of Sciences, an elected member of the Austrian Academy of Sciences and the European Academy of Sciences.
Klaus Wolkenstein is a postdoctoral researcher at the Max Planck Institute for - photo 2
Klaus Wolkenstein
is a postdoctoral researcher at the Max Planck Institute for Biophysical Chemistry in Gttingen. He studied geology/paleontology at the University of Heidelberg and completed his dissertation on phenanthroperylene quinone pigments in fossil crinoids in 2005. After a postdoctoral stay (20072010) at the Johannes Kepler University Linz in the laboratory of Wolfgang Buchberger, he worked at the State Museum of Natural History Stuttgart followed by a postdoctoral stay (20122015) at the Geoscience Centre of the University of Gttingen.
Dr. Wolkensteins main research area is the structural analysis of natural products of both fossil and extant organisms. Current research focuses on the occurrence of polyphenolic pigments in the fossil record. His scientific achievements include the discoveries of the proisocrinins and the borolithochromes. In 2006, he received the Tilly Edinger award of the German Paleontological Society.
Introduction
The living world of today is teeming with organic molecules called natural products. These are produced by living organisms within their primary or secondary metabolism. In the realm of primary metabolism, these compounds are essential to the survival of the organism, whereas the secondary metabolites mostly have an extrinsic function that may also affect other organisms. About 170,000 natural products may be traced by browsing through the Internet (as e.g. []) and a cornucopia of these is described and illustrated in the more than hundred volumes of this Progress in the Chemistry of Organic Natural Products series.
One might safely infer that this natural product ensemble is not only characteristic of our times, but has been in place throughout the eons since life has begun on earth, with organisms continuously producing a multitude of compounds. Thus, one may ask which compounds or their diagenetic derivatives from these vast amounts of ancient natural products have survived to the present day, thereby resulting in natural product molecular fossils?
The first steps to answer this question were taken rather late within the historical realms of organic and natural product chemistry when, in the 1930s, Alfred Treibs (18991983), from the Technical University of Munich, characterized desoxophylloerythroetioporphyrin () and its vanadium and iron complexes and also deuteroetioporphyrin () from oil shales and certain coals (Fig. ].
Fig 1 The molecular fossils and produced from the natural products and the - photo 3
Fig. 1
The molecular fossils and produced from the natural products and : the Treibs Scheme hypothesis
This finding has served as the origin of a novel area of research called organic geochemistry, which studies the fate of organic materials in the different compartments of the geosphere through time. Accordingly, Alfred Treibs is considered as the father of this discipline. Interestingly enough, the compounds that can be isolated from sediments, oils, and micro- or macrofossils are not only of significance for scientific reasons, but are also quite important for commercial applications, in particular in the oil industry. Geological biomarkers constitute a subgroup of molecular fossils. These can be traced to a particular biological origin and are a vivid area of research.
In this contribution, the authors have aimed to provide an overview of molecular fossils in general and biomarkers in particular together with their bioprecursors, but without attempting to provide a complete inventory of these compounds. Methods used to identify molecular fossils and processes encountered for natural products during the ages will be described. For further reading, the comprehensive textbook The Biomarker Guide by Peters, Walters, and Moldowan [], are recommended.
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