Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
CC BY-ND-NC 4.0 · Synlett 2019; 30(03): 263-274
DOI: 10.1055/s-0037-1611063
DOI: 10.1055/s-0037-1611063
account
Chlorophyll Breakdown – How Chemistry Has Helped to Decipher a Striking Biological Enigma
Further Information
Publication History
Received: 07 August 2018
Accepted after revision: 20 September 2018
Publication Date:
31 October 2018 (online)
Dedicated to Professor Franz-Peter Monforts on the occasion of his 70th birthday.
Abstract
How the fall colors arise and how chlorophyll (Chl) breakdown occurs in higher plants has remained enigmatic until three decades ago. Fundamental insights into this fascinating puzzle have been gained, meanwhile, by basic contributions from plant biology and chemistry. This short review is a personal account of key advances from synthetic, mechanistic, and structural chemistry that led to the discovery of the bilin-type Chl catabolites and helped elucidate the metabolic processes that generated them from Chl.
1 Introduction
2 Discovery and Structure Elucidation of a First Non-Green Chl Catabolite
3 Structure Elucidation of Fleetingly Existent Blue-Fluorescent Chl Catabolites
4 The Red Chl Catabolite – Key Ring-Opened Tetrapyrrole Accessed by Partial Synthesis
5 Synthesis of ‘Primary’ Fluorescent Chl Catabolites by Reduction of Red Chl Catabolite
6 Nonfluorescent Chl Catabolites from Isomerization of Fluorescent Chl Catabolites
7 Persistent Fluorescent Chl Catabolites and Blue-Luminescent Bananas
8 Discovery, Structure Elucidation, and Biological Formation of Dioxobilin-Type Chl Catabolites
9 Occurrence, Partial Synthesis, and Structure of Phyllochromobilins, the Colored Bilin-Type Chl Catabolites
10 Conclusion and Outlook
-
References
- 1 Kräutler B, Matile P. Acc. Chem. Res. 1999; 32: 35
- 2 Hendry GA. F, Houghton JD, Brown SB. New Phytol. 1987; 107: 255
- 3 Matile P. Chimia 1987; 41: 376
- 4 Kräutler B, Jaun B, Bortlik K, Schellenberg M, Matile P. Angew. Chem. Int. Ed. 1991; 30: 1315
- 5 Kräutler B. Angew. Chem. Int. Ed. 2016; 55: 4882
- 6 Hörtensteiner S, Kräutler B. Biochim. Biophys. Acta 2011; 1807: 977
- 7 Hörtensteiner S. Plant Mol. Biol. 2013; 82: 505
- 8 Kräutler B. Chem. Soc. Rev. 2014; 43: 6227
- 9 The Chemistry of Linear Oligopyrroles and Bile Pigments. Falk H. Springer; Wien: 1989
- 10 Wilks A. Heme Degradation: Mechanistic and Physiological Implications. In Tetrapyrroles: Birth, Life and Death. Warren MJ, Smith AG. Landes Bioscience; Austin Texas: 2008: 101-115
- 11 Thomas H, Bortlik K, Rentsch D, Schellenberg M, Matile P. New Phytol. 1989; 111: 3
- 12 Bortlik K, Peisker C, Matile P. J. Plant Physiol. 1990; 136: 161
- 13 Kräutler B, Jaun B, Amrein W, Bortlik K, Schellenberg M, Matile P. Plant Physiol. Biochem 1992; 30: 333
- 14 Matile P, Hörtensteiner S, Thomas H, Kräutler B. Plant Physiol. 1996; 112: 1403
- 15 Brown SB, Houghton JD, Hendry GA. F. Chlorophyll Breakdown. In Chlorophylls. Scheer H. CRC Press; Boca Raton: 1991: 465-489
- 16 Wilks A, Ikeda-Saito M. Acc. Chem. Res. 2014; 47: 2291
- 17 Matile P, Schellenberg M, Peisker C. Planta 1992; 187: 230
- 18 Hörtensteiner S, Vicentini F, Matile P. New Phytol. 1995; 129: 237
- 19 Mühlecker W, Ongania KH, Kräutler B, Matile P, Hörtensteiner S. Angew. Chem. Int. Ed. 1997; 36: 401
- 20a Mühlecker W, Kräutler B. Plant Physiol. Biochem. 1996; 34: 61
- 20b Mühlecker W, Kräutler B, Ginsburg S, Matile P. Helv. Chim. Acta 1993; 76: 2976
- 21 Mühlecker W, Kräutler B, Moser D, Matile P, Hörtensteiner S. Helv. Chim. Acta 2000; 83: 278
- 22a Engel N, Jenny TA, Mooser V, Gossauer A. FEBS Lett. 1991; 293: 131
- 22b Engel N, Curty C, Gossauer A. Plant Physiol. Biochem. 1996; 34: 77
- 23 Kräutler B, Mühlecker W, Anderl M, Gerlach B. Helv. Chim. Acta 1997; 80: 1355
- 24 Iturraspe J, Gossauer A. Tetrahedron 1992; 48: 6807
- 25 Iturraspe J, Engel N, Gossauer A. Phytochem. 1994; 35: 1387
- 26 Rodoni S, Mühlecker W, Anderl M, Kräutler B, Moser D, Thomas H, Matile P, Hörtensteiner S. Plant Physiol. 1997; 115: 669
- 27 Pružinska A, Tanner G, Anders I, Roca M, Hörtensteiner S. Proc. Natl. Acad. Sci. USA 2003; 100: 15259
- 28 Pružinska A, Anders I, Aubry S, Schenk N, Tapernoux-Lüthi E, Müller T, Kräutler B, Hörtensteiner S. Plant Cell 2007; 19: 369
- 29 Hörtensteiner S, Rodoni S, Schellenberg M, Vicentini F, Nandi OI, Qui YL, Matile P. Plant Biol. 2000; 2: 63
- 30 Hörtensteiner S, Wüthrich KL, Matile P, Ongania KH, Kräutler B. J. Biol. Chem. 1998; 273: 15335
- 31 Kräutler B, Hörtensteiner S. Handbook of Porphyrin Science. Vol. 28. Ferreira GC, Kadish KM, Smith KM, Guilard R. World Scientific Publishing; USA: 2013: 117-185
- 32 Kuai B, Chen J, Hörtensteiner S. J. Exp. Bot. 2017; 69: 751
- 33 Oberhuber M, Kräutler B. ChemBiochem 2002; 3: 104
- 34 Oberhuber M, Berghold J, Kräutler B. Angew. Chem. Int. Ed. 2008; 47: 3057
- 35 Dammeyer T, Frankenberg-Dinkel N. Photochem. Photobiol. Sci. 2008; 7: 1121
- 36a Sugishima M, Okamoto Y, Noguchi M, Kohchi T, Tamiaki H, Fukuyama K. J. Mol. Biol. 2010; 402: 879
- 36b Wüthrich KL, Bovet L, Hunziker PE, Donnison IS, Hörtensteiner S. Plant J. 2000; 21: 189
- 37 Oberhuber M, Berghold J, Breuker K, Hörtensteiner S, Kräutler B. Proc. Natl. Acad. Sci. USA 2003; 100: 6910
- 38 Müller T, Vergeiner S, Kräutler B. Int. J. Mass Spectrom. 2014; 365-366: 48-55
- 39 Kräutler B. The Porphyrin Handbook. Vol. 13. Kadish KM, Smith KM, Guilard R. Elsevier; Oxford: 2003: 183-209
- 40 Berghold J, Breuker K, Oberhuber M, Hörtensteiner S, Kräutler B. Photosynth. Res. 2002; 74: 109
- 41 Oberhuber M, Berghold J, Mühlecker W, Hörtensteiner S, Kräutler B. Helv. Chim. Acta 2001; 84: 2615
- 42 Curty C, Engel N. Phytochem. 1996; 42: 1531
- 43 Moser S, Scherzer G, Kräutler B. Chem. Biodiversity 2017; 14: e1700368
- 44 Li C, Wurst K, Berghold J, Podewitz M, Liedl KR, Kräutler B. Chem. Eur. J. 2018; 24: 2987
- 45 Moser S, Müller T, Ebert M.-O, Jockusch S, Turro NJ, Kräutler B. Angew. Chem. Int. Ed. 2008; 47: 8954
- 46a Vergeiner C, Banala S, Kräutler B. Chem. Eur. J. 2013; 19: 12294
- 46b Müller T, Kräutler B. Gerontology 2011; 57: 521
- 47 Moser S, Müller T, Holzinger A, Lütz C, Jockusch S, Turro NJ, Kräutler B. Proc. Natl. Acad. Sci. USA 2009; 106: 15538
- 48 Moser S, Müller T, Holzinger A, Lütz C, Kräutler B. Chem. Eur. J. 2012; 18: 10873
- 49 Banala S, Moser S, Müller T, Kreutz C, Holzinger A, Lütz C, Kräutler B. Angew. Chem. Int. Ed. 2010; 49: 5174
- 50 Kräutler B, Banala S, Moser S, Vergeiner C, Müller T, Lütz C, Holzinger A. FEBS Lett. 2010; 584: 4215
- 51 Erhart T, Mittelberger C, Liu XJ, Podewitz M, Li CJ, Scherzer G, Stoll G, Valls J, Robatscher P, Liedl KR, Oberhuber M, Kräutler B. Chem. Eur. J. 2018; DOI: in press; 10 1002/chem.201803128.
- 52 Moser S, Müller T, Oberhuber M, Kräutler B. Eur. J. Org. Chem. 2009; 21
- 53 Kräutler B. Photochem. Photobiol. Sci. 2008; 7: 1114
- 54a Berghold J, Eichmüller C, Hörtensteiner S, Kräutler B. Chem. Biodiversity 2004; 1: 657
- 54b Berghold J, Müller T, Ulrich M, Hörtensteiner S, Kräutler B. Monatsh. Chem. 2006; 137: 751
- 54c Pružinska A, Tanner G, Aubry S, Anders I, Moser S, Müller T, Ongania K.-H, Kräutler B, Youn J.-Y, Liljegren SJ, Hörtensteiner S. Plant Physiol. 2005; 139: 52
- 54d Erhart T, Mittelberger C, Vergeiner C, Scherzer G, Holzner B, Robatscher P, Oberhuber M, Kräutler B. Chem. Biodiversity 2016; 13: 1441
- 55 Roiser M, Müller T, Kräutler B. J. Agric. Food Chem. 2015; 63: 1385
- 56 Müller T, Ulrich M, Ongania K.-H, Kräutler B. Angew. Chem. Int. Ed. 2007; 46: 8699
- 57a Scherl M, Müller T, Kräutler B. Chem. Biodiversity 2012; 9: 2605
- 57b Ríos JJ, Roca M, Pérez-Gálvez A. J. Agric. Food Chem. 2014; 62: 10576
- 57c Vergara-Dominguez H, Rios JJ, Gandul-Rojas B, Roca M. Food Chem. 2016; 212: 604
- 58 Losey FG, Engel N. J. Biol. Chem. 2001; 276: 8643
- 59 Müller T, Rafelsberger M, Vergeiner C, Kräutler B. Angew. Chem. Int. Ed. 2011; 50: 10724
- 60 Christ B, Süssenbacher I, Moser S, Bichsel N, Egert A, Müller T, Kräutler B, Hörtensteiner S. Plant Cell 2013; 25: 1868
- 61 Süssenbacher I, Kreutz C, Christ B, Hörtensteiner S, Kräutler B. Chem. Eur. J. 2015; 21: 11664
- 62 Christ B, Schelbert S, Aubry S, Süssenbacher I, Müller T, Kräutler B, Hörtensteiner S. Plant Physiol. 2012; 158: 628
- 63 Hauenstein M, Christ B, Das A, Aubry S, Hörtensteiner S. Plant Cell 2016; 28: 2510
- 64 Süssenbacher I, Hörtensteiner S, Kräutler B. Angew. Chem. Int. Ed. 2015; 54: 13777
- 65 Mittelberger C, Yalcinkaya H, Pichler C, Gasser J, Scherzer G, Erhart T, Schumacher S, Holzner B, Janik K, Robatscher P, Müller T, Kräutler B, Oberhuber M. J. Agric. Food Chem. 2017; 65: 2651
- 66 Christ B, Hauenstein M, Hortensteiner S. Plant J. 2016; 88: 505
- 67 Ríos JJ, Pérez-Gálvez A, Roca M. Food Res. Int. 2014; 65: 255
- 68 Süßenbacher I, Christ B, Hörtensteiner S, Kräutler B. Chem. Eur. J. 2014; 20: 87
- 69 Moser S, Ulrich M, Müller T, Kräutler B. Photochem. Photobiol. Sci. 2008; 7: 1577
- 70 Ulrich M, Moser S, Müller T, Kräutler B. Chem. Eur. J. 2011; 17: 2330
- 71 Lightner DA. Progr. Chem. Org. Nat. Prod. 2013; 98: 1
- 72 Li CJ, Wurst K, Jockusch S, Gruber K, Podewitz M, Liedl KR, Kräutler B. Angew. Chem. Int. Ed. 2016; 55: 15760
- 73 Li C, Kräutler B. J. Porphyrins Phthalocyanines 2016; 20: 388
- 74 Vergeiner C, Ulrich M, Li C, Liu X, Müller T, Kräutler B. Chem. Eur. J. 2015; 21: 136
- 75a Wakana D, Kato H, Momose T, Sasaki N, Ozeki Y, Goda Y. Tetrahedron Lett. 2014; 55: 2982
- 75b Roca M, Rios JJ, Chahuaris A, Perez-Galvez A. Food Res. Int. 2017; 100: 332
- 76 Li C. J.; Erhart T.; Liu X. J.; Kräutler B. manuscript in preparation.
- 77 Li C, Ulrich M, Liu X, Wurst K, Müller T, Kräutler B. Chem. Sci. 2014; 5: 3388
- 78 Li C, Kräutler B. Dalton Trans. 2015; 44: 10116
- 79 Li C. J.; Kräutler B. manuscript in preparation.
- 80 Li C. J.; Kräutler B.; unpublished work.
- 81 Suzuki Y, Shioi Y. Plant Cell Physiol. 1999; 40: 909
- 82 Tanaka R, Tanaka A. Biochim. Biophys. Acta 2011; 1807: 968
- 83 Erhart T, Vergeiner S, Kräutler B, Müller T. Angew. Chem. Int. Ed. 2018; DOI: in press; 10 1002/anie.201807818.
- 84 Thomas H, Huang L, Young M, Ougham H. BMC Evol. Biol. 2009; 9: 163
- 85 Matile P, Duggelin T, Schellenberg M, Rentsch D, Bortlik K, Peisker C, Thomas H. Plant Physiol. Biochem. 1989; 27: 595
- 86 Kashiyama Y, Yokoyama A, Kinoshita Y, Shoji S, Miyashiya H, Shiratori T, Suga H, Ishikawa K, Ishikawa A, Inouye I, Ishida K, Fujinuma D, Aoki K, Kobayashi M, Nomoto S, Mizoguchi T, Tamiaki H. Proc. Natl. Acad. Sci. USA 2012; 109: 17328
- 87 Jockusch S, Turro NJ, Banala S, Kräutler B. Photochem. Photobiol. Sci. 2014; 13: 407
- 88 Apel K, Hirt H. Annu. Rev. Plant Biol. 2004; 55: 373
- 89 Buchanan BB, Gruissem W, Jones RL. Biochemistry and Molecular Biology of Plants. Am. Soc. Plant Physiologists; Rockville: 2001
- 90 Scherl M, Müller T, Kreutz C, Huber RG, Zass E, Liedl KR, Kräutler B. Chem. Eur. J. 2016; 22: 9498
- 91 Demmig-Adams B, Adams III WW, Mattoo A. Photoprotection Photoinhibition Gene Regulation and Environment. In Advances in Photosynthesis and Respiration. Vol. 21. Springer; Dordrecht: 2006