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Pyrrolic and Dipyrrolic Chlorophyll Degradation Products in Plants and Herbivores.

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.

SUBMITTER: Ritter M

PROVIDER: S-EPMC7318184 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Pyrrolic and Dipyrrolic Chlorophyll Degradation Products in Plants and Herbivores.

Ritter Marcel M Oetama Vincensius S P VSP Schulze Daniel D Muetzlaff Katrin K Meents Anja K AK Seidel Raphael A RA Görls Helmar H Westerhausen Matthias M Boland Wilhelm W Pohnert Georg G

Chemistry (Weinheim an der Bergstrasse, Germany) 20200428 28

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 p ...[more]

PMID: 31971638

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Project description:This publication reports high resolution mass spectral data for copper chlorophyll and copper chlorophyll degradation products extracted from bright green table olives. These data support analyte identifications made in "Quantitation of copper chlorophylls in green table olives by ultra-high-performance liquid chromatography with inductively coupled plasma isotope dilution mass spectrometry" in the Journal of Chromatography A (Petigara Harp et al., 2020 [1]). Table olive pigments, divided into lipophilic and hydrophilic fractions by liquid-liquid repartition, were separated by ultra-high-performance liquid chromatography and detected by visible wavelength absorbance and high resolution mass spectrometry, using an Orbitrap HF with positive electrospray ionization. Full-scan mass spectra were acquired to assign pigment chemical formulae. Fragment-rich higher-energy collisional dissociation tandem mass spectra were acquired to facilitate structural assignments. Extracted ion chromatograms, full-scan, and tandem mass spectra obtained from representative lipophilic and hydrophilic green table olive extracts are presented in Figures 1-6. Annotated mass spectra comparing experimental and calculated isotope distributions, .raw mass spectral data files, and experimental details linking .raw data files to annotated spectra are provided as Supplementary Material. Spectra extracted from these native data files can be added to mass spectral libraries for use in other studies. Access to native data files uniquely enables rigorous data examination (e.g., molecular ion isotopic distribution, effective mass resolution, presence of overlapping ion series) and use in ways that are not possible when spectra are otherwise reported in simple tables listing mono-isotopic peaks and mass errors. Mass spectra reported here can be used to design multiple-reaction monitoring methods to detect these bright green pigments in agricultural food commodities and finished products.

Dataset Information

Pyrrolic and Dipyrrolic Chlorophyll Degradation Products in Plants and Herbivores.

Publications

Pyrrolic and Dipyrrolic Chlorophyll Degradation Products in Plants and Herbivores.

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