Transition metal complexes of phyllobilins – a new realm of bioinorganic chemistry

Chengjie Li and Bernhard Kräutler

Dalton Trans., 2015, 44, 10116
DOI: 10.1039/C5DT00474H

Blue transition metal complexes of a natural bilin-type chlorophyll catabolite

Chengjie Li, Markus Ulrich, Xiujun Liu, Klaus Wurst, Thomas Müller and Bernhard Kräutler

Chem. Sci., 2014, 5, 3388
DOI: 10.1039/C4SC00348A

Direct Plant Tissue Analysis and Imprint Imaging by Desorption Electrospray Ionization Mass Spectrometry

Thomas Müller, Sheran Oradu, Demian R. Ifa, R. Graham Cooks and Bernhard Kräutler

Anal. Chem., 2011, 83, 5754
DOI: 10.1021/ac201123t

Chlorophyll Catabolites in Fall Leaves of the Wych Elm Tree Present a Novel Glycosylation Motif

Mathias Scherl, Thomas Müller, Christoph R. Kreutz, Roland G. Huber, Engelbert Zass, Klaus R. Liedl and Bernhard Kräutler

Chemistry A European J, 2016, 22, 9498
DOI: 10.1002/chem.201601739

Structural Characterization, and Antioxidative and Anti-inflammatory Activities of Phylloxanthobilins in Tropaeolum majus, a Plant with Relevance in Phytomedicine

Patricia Frei, Christian Nadegger, Angelika M. Vollmar, Thomas Müller and Simone Moser

Planta Med, 2024, 90, 641
DOI: 10.1055/a-2225-8314

Je bunter, desto bioaktiver

Cornelia Karg and Simone Moser

Nachr Chem, 2022, 70, 65
DOI: 10.1002/nadc.20224119948

Ein Dioxobilan als Produkt eines divergenten Chlorophyllabbaus in Spitzahorn

Thomas Müller, Martina Rafelsberger, Clemens Vergeiner and Bernhard Kräutler

Angewandte Chemie, 2011, 123, 10912
DOI: 10.1002/ange.201103934

Characterization of the pheophorbide a oxygenase/phyllobilin pathway of chlorophyll breakdown in grasses

Aditi Das, Bastien Christ and Stefan Hörtensteiner

Planta, 2018, 248, 875
DOI: 10.1007/s00425-018-2946-2

Mechanism and Significance of Chlorophyll Breakdown

Bastien Christ and Stefan Hörtensteiner

J Plant Growth Regul, 2014, 33, 4
DOI: 10.1007/s00344-013-9392-y

Zn-complex of a natural yellow chlorophyll catabolite

Chengjie Li and Bernhard Kräutler

J. Porphyrins Phthalocyanines, 2016, 20, 388
DOI: 10.1142/S1088424616500176

Re-opening the stage for Echinacea research - Characterization of phylloxanthobilins as a novel anti-oxidative compound class in Echinacea purpurea

Cornelia A. Karg, Pengyu Wang, Angelika M. Vollmar and Simone Moser

Phytomedicine, 2019, 60, 152969
DOI: 10.1016/j.phymed.2019.152969

Phyllobilins as a challenging diverse natural product class: Exploration of pharmacological activities

Pengyu Wang, Cornelia A. Karg, Nadine Frey, Julian Frädrich, Angelika M. Vollmar and Simone Moser

Archiv der Pharmazie, 2021, 354
DOI: 10.1002/ardp.202100061

Chlorophyll breakdown in fruits: the relevance of the senescence-related pheophorbide a oxygenase/ phyllobilin (PaO/PB) pathway in ripe ‘Gala’ apples (Malus × domestica)

L.M. Gorfer, L. Vestrucci, V. Grigoletto, V. Lazazzara, A. Zanella, P. Robatscher, M. Scampicchio and M. Oberhuber

Acta Hortic., 2022, 9
DOI: 10.17660/ActaHortic.2022.1353.2

Breakdown of Chlorophyll in Higher Plants—Phyllobilins as Abundant, Yet Hardly Visible Signs of Ripening, Senescence, and Cell Death

Bernhard Kräutler

Angew Chem Int Ed, 2016, 55, 4882
DOI: 10.1002/anie.201508928

A pink colored dioxobilin-type phyllobilin from breakdown of chlorophyll

Chengjie Li and Bernhard Kräutler

Monatsh Chem, 2019, 150, 813
DOI: 10.1007/s00706-019-02396-5

The advent of phyllobilins as bioactive phytochemicals – natural compounds derived from chlorophyll in medicinal plants and food with immunomodulatory activities

Angelika M. Vollmar and Simone Moser

Pteridines, 2023, 34
DOI: 10.1515/pteridines-2022-0047

Chlorophyll breakdown in higher plants

Stefan Hörtensteiner and Bernhard Kräutler

Biochimica et Biophysica Acta (BBA) - Bioenergetics, 2011, 1807, 977
DOI: 10.1016/j.bbabio.2010.12.007

A Chlorophyll-Derived Phylloxanthobilin Is a Potent Antioxidant That Modulates Immunometabolism in Human PBMC

Cornelia A. Karg, Lucia Parráková, Dietmar Fuchs, Harald Schennach, Bernhard Kräutler, Simone Moser and Johanna M. Gostner

Antioxidants, 2022, 11, 2056
DOI: 10.3390/antiox11102056

Chlorophyll Catabolites – Chemical and Structural Footprints of a Fascinating Biological Phenomenon

Simone Moser, Thomas Müller, Michael Oberhuber and Bernhard Kräutler

Eur J Org Chem, 2009, 2009, 21
DOI: 10.1002/ejoc.200800804

An evergreen mind and a heart for the colors of fall

Sylvain Aubry, Bastien Christ, Bernhard Kräutler, Enrico Martinoia, Howard Thomas, Cyril Zipfel and Karl-Josef Dietz

Journal of Experimental Botany, 2021, 72, 4625
DOI: 10.1093/jxb/erab162

Chlorophyll catabolites in conditioned media of green microalga Desmodesmus subspicatus

Krzysztof Grabski, Natalia Baranowski, Joanna Skórko-Glonek and Zbigniew Tukaj

J Appl Phycol, 2016, 28, 889
DOI: 10.1007/s10811-015-0618-1

Non-fluorescent and yellow chlorophyll catabolites in Japanese plum fruits (Prunus salicina, Lindl.)

María Roca, José Julián Ríos, Alexandra Chahuaris and Antonio Pérez-Gálvez

Food Research International, 2017, 100, 332
DOI: 10.1016/j.foodres.2017.07.029

Phyllobilins from Senescence-Associated Chlorophyll Breakdown in the Leaves of Basil (Ocimum basilicum) Show Increased Abundance upon Herbivore Attack

Simone Moser, Theresia Erhart, Sigrid Neuhauser and Bernhard Kräutler

J. Agric. Food Chem., 2020, 68, 7132
DOI: 10.1021/acs.jafc.0c02238

Side‐chain modifications of phyllobilins may not be essential for chlorophyll degradation in Arabidopsis

Mareike Hauenstein, Stefan Hörtensteiner and Sylvain Aubry

Plant Direct, 2022, 6
DOI: 10.1002/pld3.441

Phyllobilins – Bioactive Natural Products Derived from Chlorophyll – Plant Origins, Structures, Absorption Spectra, and Biomedical Properties

Cornelia A. Karg, Masahiko Taniguchi, Jonathan S. Lindsey and Simone Moser

Planta Med, 2023, 89, 637
DOI: 10.1055/a-1955-4624

Chlorophyll‐Derived Yellow Phyllobilins of Higher Plants as Medium‐Responsive Chiral Photoswitches

Chengjie Li, Klaus Wurst, Steffen Jockusch, Karl Gruber, Maren Podewitz, Klaus R. Liedl and Bernhard Kräutler

Angew Chem Int Ed, 2016, 55, 15760
DOI: 10.1002/anie.201609481

In Search of Bioactivity – Phyllobilins, an Unexplored Class of Abundant Heterocyclic Plant Metabolites from Breakdown of Chlorophyll

Simone Moser and Bernhard Kräutler

Israel Journal of Chemistry, 2019, 59, 420
DOI: 10.1002/ijch.201900012

The biochemistry and molecular biology of chlorophyll breakdown

Benke Kuai, Junyi Chen and Stefan Hörtensteiner

Journal of Experimental Botany, 2018, 69, 751
DOI: 10.1093/jxb/erx322

Pyro‐Phyllobilins: Elusive Chlorophyll Catabolites Lacking a Critical Carboxylate Function of the Natural Chlorophylls

Chengjie Li, Klaus Wurst, Joachim Berghold, Maren Podewitz, Klaus R. Liedl and Bernhard Kräutler

Chemistry A European J, 2018, 24, 2987
DOI: 10.1002/chem.201705331

NMR-based characterization of a novel yellow chlorophyll catabolite, Ed-YCC, isolated from Egeria densa

Daigo Wakana, Hiroki Kato, Tadayuki Momose, Nobuhiro Sasaki, Yoshihiro Ozeki and Yukihiro Goda

Tetrahedron Letters, 2014, 55, 2982
DOI: 10.1016/j.tetlet.2014.03.114

Phylloxanthobilins are Abundant Linear Tetrapyrroles from Chlorophyll Breakdown with Activities Against Cancer Cells

Cornelia A. Karg, Pengyu Wang, Florian Kluibenschedl, Thomas Müller, Lars Allmendinger, Angelika M. Vollmar and Simone Moser

Eur J Org Chem, 2020, 2020, 4499
DOI: 10.1002/ejoc.202000692

Impulse Lecture “Phyllobilins – An Underexplored Family of Natural Products at the Center of a Scientific and Personal Journey”

Simone Moser

Planta Med, 2023, 89, 1276
DOI: 10.1055/s-0043-1773810

Cytochrome P450 CYP89A9 Is Involved in the Formation of Major Chlorophyll Catabolites during Leaf Senescence in Arabidopsis

Bastien Christ, Iris Süssenbacher, Simone Moser, Nicole Bichsel, Aurelie Egert, Thomas Müller, Bernhard Kräutler and Stefan Hörtensteiner

The Plant Cell, 2013, 25, 1868
DOI: 10.1105/tpc.113.112151

Der Chlorophyllabbau in höheren Pflanzen – Phyllobiline als weitverbreitete, aber kaum sichtbare Zeichen von Reifung, Seneszenz und Zelltod

Bernhard Kräutler

Angewandte Chemie, 2016, 128, 4964
DOI: 10.1002/ange.201508928

Characterization of Phyllobilins in Hops: Antioxidant and Potentially Bitter Senescence-Related Metabolites

Christian Nadegger, Patricia Frei, Christian A. Elvert, Cornelia A. Karg, Johanna M. Gostner, Jonathan S. Lindsey, Christoph R. Kreutz, Stefan Schwaiger, Thomas Müller and Simone Moser

J. Agric. Food Chem., 2025, 73, 17637
DOI: 10.1021/acs.jafc.5c03549

Synthesis, spectroscopic and crystallographic analysis of the Zn-complex of a di(β,β′-sulfoleno)pyrrin: model for Zn-complexes of bilirubin and of phylloxanthobilins

Chengjie Li, Klaus Wurst, Yaqing Feng and Bernhard Kräutler

Monatsh Chem, 2016, 147, 1031
DOI: 10.1007/s00706-016-1748-0

How the Colourless ‘Nonfluorescent’ Chlorophyll Catabolites Rust

Markus Ulrich, Simone Moser, Thomas Müller and Bernhard Kräutler

Chemistry A European J, 2011, 17, 2330
DOI: 10.1002/chem.201003313

Stereo‐ and Regioselective Phyllobilane Oxidation in Leaf Homogenates of the Peace Lily (Spathiphyllum wallisii): Hypothetical Endogenous Path to Yellow Chlorophyll Catabolites

Clemens Vergeiner, Markus Ulrich, Chengjie Li, Xiujun Liu, Thomas Müller and Bernhard Kräutler

Chemistry A European J, 2015, 21, 136
DOI: 10.1002/chem.201404783

Water deficit induces chlorophyll degradation via the ‘PAO/phyllobilin’ pathway in leaves of homoio‐ (Craterostigma pumilum) and poikilochlorophyllous (Xerophyta viscosa) resurrection plants

BASTIEN CHRIST, AURÉLIE EGERT, IRIS SÜSSENBACHER, BERNHARD KRÄUTLER, DOROTHEA BARTELS, SHAUN PETERS and STEFAN HÖRTENSTEINER

Plant Cell & Environment, 2014, 37, 2521
DOI: 10.1111/pce.12308

Profile of Chlorophyll Catabolites in Senescent Leaves of Epipremnun aureum Includes a Catabolite Esterified with Hydroxytyrosol 1-O-Glucoside

María Roca and Antonio Pérez-Gálvez

J. Nat. Prod., 2020, 83, 873
DOI: 10.1021/acs.jnatprod.9b00546

A yellow chlorophyll catabolite in leaves of Urtica dioica L.: An overlooked phytochemical that contributes to health benefits of stinging nettle

Cornelia A. Karg, Christian Doppler, Charlotte Schilling, Franziska Jakobs, Marlene C.S. Dal Colle, Nadine Frey, David Bernhard, Angelika M. Vollmar and Simone Moser

Food Chemistry, 2021, 359, 129906
DOI: 10.1016/j.foodchem.2021.129906

Rising levels of antioxidative phyllobilins in stored agricultural produce and their impact on consumer acceptance

Cornelia A. Karg, Christina M. Neubig, Jutta Roosen and Simone Moser

npj Sci Food, 2021, 5
DOI: 10.1038/s41538-021-00101-7

Chlorophyll breakdown during fruit ripening: Qualitative analysis of phyllobilins in the peel of apples (Malus domestica Borkh.) cv. ‘Gala’ during different shelf life stages

Lisa Marie Gorfer, Luca Vestrucci, Valentina Grigoletto, Valentina Lazazzara, Angelo Zanella, Peter Robatscher, Matteo Scampicchio and Michael Oberhuber

Food Research International, 2022, 162, 112061
DOI: 10.1016/j.foodres.2022.112061

Von Chlorophyll abstammende gelbe Phyllobiline höherer Pflanzen als umgebungsgesteuerte, chirale Photoschalter

Chengjie Li, Klaus Wurst, Steffen Jockusch, Karl Gruber, Maren Podewitz, Klaus R. Liedl and Bernhard Kräutler

Angewandte Chemie, 2016, 128, 15992
DOI: 10.1002/ange.201609481

Update on the biochemistry of chlorophyll breakdown

Stefan Hörtensteiner

Plant Mol Biol, 2013, 82, 505
DOI: 10.1007/s11103-012-9940-z

A Dioxobilane as Product of a Divergent Path of Chlorophyll Breakdown in Norway Maple

Thomas Müller, Martina Rafelsberger, Clemens Vergeiner and Bernhard Kräutler

Angew Chem Int Ed, 2011, 50, 10724
DOI: 10.1002/anie.201103934

Chlorophyll Breakdown in Senescent Banana Leaves: Catabolism Reprogrammed for Biosynthesis of Persistent Blue Fluorescent Tetrapyrroles

Clemens Vergeiner, Srinivas Banala and Bernhard Kräutler

Chemistry A European J, 2013, 19, 12294
DOI: 10.1002/chem.201301907

Structures of Chlorophyll Catabolites in Bananas (Musa acuminata) Reveal a Split Path of Chlorophyll Breakdown in a Ripening Fruit

Simone Moser, Thomas Müller, Andreas Holzinger, Cornelius Lütz and Bernhard Kräutler

Chemistry A European J, 2012, 18, 10873
DOI: 10.1002/chem.201201023

Chlorophyll Catabolites in Senescent Leaves of the Plum Tree (Prunus domestica)

Theresia Erhart, Cecilia Mittelberger, Clemens Vergeiner, Gerhard Scherzer, Barbara Holzner, Peter Robatscher, Michael Oberhuber and Bernhard Kräutler

Chemistry & Biodiversity, 2016, 13, 1441
DOI: 10.1002/cbdv.201600181

A Blue Zinc Complex of a Dioxobilin‐Type Pink Chlorophyll Catabolite Exhibiting Bright Chelation‐Enhanced Red Fluorescence

Chengjie Li, Maren Podewitz and Bernhard Kräutler

Eur J Inorg Chem, 2021, 2021, 1904
DOI: 10.1002/ejic.202100206

Tetrapyrrolische Pigmente aus dem Häm‐ und Chlorophyllabbau interagieren mit Aktin

Cornelia A. Karg, Shuaijun Wang, Nader Al Danaf, Ryan P. Pemberton, Denzil Bernard, Maibritt Kretschmer, Sabine Schneider, Themistoklis Zisis, Angelika M. Vollmar, Don C. Lamb, Stefan Zahler and Simone Moser

Angewandte Chemie, 2021, 133, 22753
DOI: 10.1002/ange.202107813

Pathogen-Induced Leaf Chlorosis: Products of Chlorophyll Breakdown Found in Degreened Leaves of Phytoplasma-Infected Apple (Malus × domestica Borkh.) and Apricot (Prunus armeniaca L.) Trees Relate to the Pheophorbide a Oxygenase/Phyllobilin Pathway

Cecilia Mittelberger, Hacer Yalcinkaya, Christa Pichler, Johanna Gasser, Gerhard Scherzer, Theresia Erhart, Sandra Schumacher, Barbara Holzner, Katrin Janik, Peter Robatscher, Thomas Müller, Bernhard Kräutler and Michael Oberhuber

J. Agric. Food Chem., 2017, 65, 2651
DOI: 10.1021/acs.jafc.6b05501

Chlorophyll Catabolites in Senescent Leaves of the Lime Tree (Tilia cordata)

Mathias Scherl, Thomas Müller and Bernhard Kräutler

Chemistry & Biodiversity, 2012, 9, 2605
DOI: 10.1002/cbdv.201200203

Yellow Dioxobilin‐Type Tetrapyrroles from Chlorophyll Breakdown in Higher Plants—A New Class of Colored Phyllobilins

Chengjie Li, Theresia Erhart, Xiujun Liu and Bernhard Kräutler

Chemistry A European J, 2019, 25, 4052
DOI: 10.1002/chem.201806038

Facile retro-Dieckmann cleavage of a pink phyllobilin: new type of potential downstream steps of natural chlorophyll breakdown

Chengjie Li and Bernhard Kräutler

Monatsh Chem, 2023, 154, 1359
DOI: 10.1007/s00706-022-02894-z

Mass spectrometry: the indispensable tool for plant metabolomics of colourless chlorophyll catabolites

María Roca, José J. Ríos and Antonio Pérez-Gálvez

Phytochem Rev, 2018, 17, 453
DOI: 10.1007/s11101-017-9543-z

Tetrapyrrolic Pigments from Heme‐ and Chlorophyll Breakdown are Actin‐Targeting Compounds

Cornelia A. Karg, Shuaijun Wang, Nader Al Danaf, Ryan P. Pemberton, Denzil Bernard, Maibritt Kretschmer, Sabine Schneider, Themistoklis Zisis, Angelika M. Vollmar, Don C. Lamb, Stefan Zahler and Simone Moser

Angew Chem Int Ed, 2021, 60, 22578
DOI: 10.1002/anie.202107813

Isolation, characterization, and antioxidative activity of a dioxobilin-type phylloxanthobilin from savoy cabbage

Cornelia A. Karg, Charlotte M. Schilling, Lars Allmendinger and Simone Moser

J. Porphyrins Phthalocyanines, 2019, 23, 881
DOI: 10.1142/S1088424619500718

A liquid chromatography–mass spectrometry platform for the analysis of phyllobilins, the major degradation products of chlorophyll in Arabidopsis thaliana

Bastien Christ, Mareike Hauenstein and Stefan Hörtensteiner

The Plant Journal, 2016, 88, 505
DOI: 10.1111/tpj.13253