Pyrrolic and Dipyrrolic Chlorophyll Degradation Products in Plants and Herbivores |
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| Authors: | Marcel Ritter Vincensius S P Oetama Daniel Schulze Katrin Muetzlaff Anja K Meents Dr Raphael A Seidel Dr Helmar Görls Prof Dr Matthias Westerhausen Prof Dr Wilhelm Boland Prof Dr Georg Pohnert |
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| Institution: | 1. Friedrich Schiller University Jena, Institute of Inorganic and Analytical Chemistry, Lessingstr. 8, 07743 Jena, Germany;2. Max Planck Institute for Chemical Ecology, Hans-Knöll-Str. 8, 07745 Jena, Germany;3. Friedrich Schiller University Jena, Institute of Inorganic and Analytical Chemistry, Humboldtstr. 8, 07743 Jena, Germany |
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| Abstract: | The degradation of chlorophyll, the omnipresent green pigment, has been investigated intensively over the last 30 years resulting in many elucidated tetrapyrrolic degradation products. With a comparison to the degradation of the structurally similar heme, we hereby propose a novel additional chlorophyll degradation mechanism to mono- and dipyrrolic products. This is the first proof of the occurrence of a family of mono- and dipyrrols in leaves that are previously only known as heme degradation products. This product family is also found in spit and feces of herbivores with specific metabolomic patterns reflecting the origin of the samples. Based on chromatographic and mass spectrometric evidence as well as on mechanistic considerations we also suggest several tentative new degradation products. One of them, dihydro BOX A, was fully confirmed as a novel natural product by synthesis and comparison of its spectroscopic data. |
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| Keywords: | bilirubin oxidation end products chlorophyll degradation natural products porphyrinoids propentdyopents |
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