The degradation of chlorophyll,t he omnipresent green pigment, has been investigatedi ntensively over the last 30 years resulting in manye lucidated tetrapyrrolic degradationp roducts. With ac omparison to the degradation of the structurally similarh eme, we hereby propose an ovel additionalc hlorophyll degradation mechanism to mono-and dipyrrolic products.T his is the first proof of the occurrence of af amilyo fm ono-and dipyrrols in leaves that are previously only known as heme degradationp roducts.T his prod-uct familyi sa lso found in spit and feces of herbivores with specific metabolomic patterns reflecting the origin of the samples. Based on chromatographica nd mass spectrometric evidencea swell as on mechanistic considerations we also suggest severalt entative new degradation products.O ne of them,d ihydro BOX A, was fully confirmed as an ovel natural product by synthesis andc omparison of its spectroscopic data.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.org/10. Scheme1.Enzymatic chlorophyll degradation in plants.Scheme2.Enzymatic (top) andoxidativeheme degradation by reactive oxygen species (ROS) to PDPs and BOXes.
Chlorophyll (Chl) is a natural compound that is found in all autotrophic plants. Since phytophagous insects ingest the photosynthetically active material with the plant leaves, the question arises if and how herbivores deal with Chl and its degradation products. Here we review findings on Chl degradation in phytophagous insects and highlight the role of these ubiquitous plant metabolites for plant-feeding insects. Due to the anaerobic gut of many insects, the degradation is limited to the removal of the peripheral substituents, while the tetrapyrrole core remains intact. Proteins, such as red fluorescent protein, P252 (a novel 252-kDa protein), and chlorophyllide binding protein have been reported to occur in the insect gut and might be indirectly connected to Chl degradation. Besides of an nutritional value, e.g., by taking up Mg 2+ ions or by sequestration of carbon from the phytol side chain, the Chl degradation products may serve the insect, after binding to certain proteins, as antimicrobial, antifungal, and antiviral factors. The protein complexes may also confer protection against reactive oxygen species. The antibiotic potential of proteins and degradation products does not only benefit phytophagous insects but also human being in medical application of cancer treatment for instance. This review highlights these aspects from a molecular, biochemical, and ecological point of view.
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