Chlorophyll catabolism - Structures, mechanisms, conversions

Journal of Photochemistry and Photobiology B: Biology

Volumn 32, Issue 3, 1996, Pages 141-151

  Gossauer, Albert ^a   Engel, Norbert ^a  

^a Organisch chemisches Institut   (Switzerland)

Author keywords

Autumnal chlorophyll degradation; Chlorella protothecoides; Chlorophyll catabolism in green algae; Chlorophyll catabolites in a chlorophyte; Chlorophyll catabolites in angiosperms; Linear tetrapyrroles

Indexed keywords

CHLOROPHYLL; MACROCYCLIC COMPOUND; OXYGEN 18; UNSPECIFIC MONOOXYGENASE;

CATABOLISM; CHLORELLA; GREEN ALGA; HIGHER PLANT; NONHUMAN; OXIDATION; PRIORITY JOURNAL; REVIEW;

ALGAE; AUXENOCHLORELLA PROTOTHECOIDES; CHLORELLA PROTOTHECOIDES; CHLOROPHYTA; EMBRYOPHYTA; MAGNOLIOPHYTA;

EID: 0029872091     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/1011-1344(95)07257-8     Document Type: Article

References (82)

1. F.G. Kohl, Untersuchungen über das Karotin und seine physiologische Bedeutung, Leipzig, 1902, p. 109.
2. F.-C. Czygan, Sekundär-Carotinoide in Grünalgen. II. Untersuchungen zur Biogenese, Archiv. Mikrobiol., 62 (1968) 209-236.
3. For comprehensive reviews see (a) G.A.F. Hendry, J.D. Houghton and S .B. Brown, The degradation of chlorophyll - A biological enigma, New Phytol, 107 (1987) 255-302;
4. (b) S.B. Brown, J.D. Houghton and G.F. Hendry, Chlorophyll breakdown, in H. Scheer (ed.), Chlorophylls, CRC Press, Boca Raton, FL, 1991, pp. 465-489.
5. Y. Oshio and E. Hase, Studies on red pigments excreted by cells of Chlorella protothecoides during the process of bleaching induced by glucose or acetate I. Chemical properties of the red pigments, Plant Cell Physiol., 10 (1969) 41-49; II. Mode of formation of the red pigments, Plant Cell Physiol., 10 (1969) 51-59.
6. Y. Oshio and E. Hase, Studies on red pigments excreted by cells of Chlorella protothecoides during the process of bleaching induced by glucose or acetate I. Chemical properties of the red pigments, Plant Cell Physiol., 10 (1969) 41-49; II. Mode of formation of the red pigments, Plant Cell Physiol., 10 (1969) 51-59.
7. H. Nakamura, B. Musicki, Y. Kishi and O. Shimomura, Structure of the light emitter in krill (Euphausia pacifica) bioluminescence, J. Am. Chem. Soc., 110 (1988) 2683-2695.
8. R.L. Metcalf, A study of the metabolism of chlorophyll in the squash bug Anasa tristis DeGeer, Entomol. Soc. Am., 38 (1945) 397-402.
9. H. Nakamura, Y. Kishi, O. Shimomura, D. Morse and J.W. Hastings, Structure of dinoflagellate luciferin and its enzymatic and nonenzymatic air-oxidation products, J. Am. Chem. Soc., 111 (1989) 7607-7611.
10. M. Doi, Y. Shioi and T. Sasa, Purification and characterisation of a blue-colored red fluorescent protein from the silkworm (Bombyx mori L.) larvae, Comp. Biochem. Physiol., 83B (1986) 569-573.
11. J.I. Kusuda, J.-I. Mukai, A biliprotein from the digestive juice of Bombyx mori L. Its purification and partial structural study of the chromophore, Comp. Biochem. Physiol., 39B (1971) 317-323.
12. K. Hayashiya, Red fluorescent protein in the digestive juice of the silkworm larvae fed on host-plant mulberry leaves, Ent. Exp. Appl., 24 (1978) 228-236.
13. K. Miyake, M. Ohtomi, H. Yoshizawa, Y. Sakamoto, K. Nakayama and M. Okada, Water soluble pigments containing xylose and glucose in gametangia of the green alga, Bryopis maxima, Plant Cell Physiol., 36 (1995) 109-113.
14. J. Dupont and P.A. Siegenthaler, A parallel study of pigment bleaching and cytochrome breakdown during ageing of thylakoid membranes, Plant Cell Physiol., 27 (1986) 473-484.
15. E. Stahl, Zur Biologie des Chlorophylls, Laubfarbe und Himmelslicht Vergilbung und Etiolement, Verlag Gustav Fischer, Jena 1909, p. 132.
16. For comprehensive review see: P. Matile, Vom Ergrünen und Vergilben der Blätter, Edited by the Naturforschender Gesellschaft in Zürich, 1991.
17. For a comprehensive review on plant senescence see: L.D. Noodén, A.C. Leopold (eds.), Senescence and Aging in Plants, Academic Press, Inc., 1988.
18. K. Bortlik, H. Gut and P. Matile, Yellowing and non-yellowing trees: a comparison of protein- and chlorophyll-loss in senescent leaves, Bot. Helv., 97 (1987) 323-328.
19. E. Martinoia, U. Heck, M.J. Dalling and P. Matile, Changes in chloroplasts number and chloroplast constituents in senescing barley leaves, Biochem. Physiol. Pflanz., 178 (1983) 147-155.
20. P. Matile, Seneszenz bei Pflanzen und ihre Bedeutung für den Stickstoff-Haushalt, CHIMIA, 41 (1987) 376-381.
21. P. Matile, T. Düggelin, M. Schellenberg, D. Rentsch, K. Bortlik, C. Peisker and H. Thomas, How and why is chlorophyll broken down in senescent leaves?, Plant Physiol. Biochem., 27 (1989) 595-604.
22. R. Willstätter and A. Stoll, Untersuchungen über Chlorophyll, Springer Verlag, Berlin, 1911.
23. R.B. Woodward, Totalsynthese des Chlorophylls, Angew. Chem., 72 (1960) 651-662.
24. I. Flemming, Absolute configuration and structure of chlorophyll, Nature, 216 (1967) 151-152.
25. H. Brockman jr., Zur absoluten Konfiguration des Chlorophylls, Angew. Chem., 80 (1968) 233-234; Angew. Chem. Int. Ed. Engl., 7 (1968) 22-25.
26. H. Brockman jr., Zur absoluten Konfiguration des Chlorophylls, Angew. Chem., 80 (1968) 233-234; Angew. Chem. Int. Ed. Engl., 7 (1968) 22-25.
27. Commission on the nomenclature of biological chemistry. Definitive rules for the nomenclature of amino acids, steroides, vitamins and carotenoides,J. Am. Chem. Soc., 82 (1960) V-15, 5582.
28. G.P. Moss, Nomenclature of tetrapyrroles: Recommendations 1986, Pure Appl. Chem., 59 (1987) 779-832.
29. J. Merritt and K.L. Loening, Nomenclature of tetrapyrroles: Recommendations 1978, Eur. J. Biochem., 108 (1980) 1-30.
30. R. Panico, W.H. Powell and J.-C. Richer (eds.), A guide to IUPAC nomenclature of organic compounds: Recommendations 1993, Blackwell, Oxford 1993.
31. R. Ziegler and S.H. Schanderl, Chlorophyll degradation and the kinetics of dephytylated derivatives in a mutant of Chlorella, Photosynthetica, 3 (1969) 45-54.
32. D. Amir-Shapira, E.E. Goldschmidt and A. Altman, Chlorophyll catabolism in senescing plant tissues: in vivo breakdown intermediates suggest different degradative pathways from citrus fruit and parsley leaves, Proc. Natl. Acad. Sci. USA, 84 (1987) 1901-1908.
33. W. Terpstra, Identification of chlorophyllase as glycoprotein, FEBS Lett., 126 (1981) 231-235.
34. J.W.J. Lambers, H.W. Velthuis and W. Terpstra, Molecular mass estimation of chlorophyllase in situ by radiation inactivation analysis. Studies on the composition of the isolated enzyme, Biochim. Biophys. Acta, 831 (1985) 213-224.
35. K. Tanaka, T. Kakumo, J. Yamashita and T. Horio, Purification and properties of chlorophyllase from greened rye seedlings, J. Biochem. (Tokyo), 92 (1982) 1763-1773.
36. W. Terpstra and J.W.J. Lambers, Interactions between chlorophyllase, chlorophyll a, plant lipids and magnesium, Biochim. Biophys. Acta, 746 (1983) 23-31.
37. H. Thomas, K. Bortlik, D. Rentsch, M. Schellenberg and P. Matile, Catabolism of chlorophyll in vivo: significance of polar chlorophyll catabolites in a non-yellowing senescence mutant of Festuca pratensis Huds., New Phytol., 111 (1989) 3-8.
38. K. Bortlik, C. Peisker and P. Matile, A novel type of chlorophyll catabolite in senescent barley leaves, J. Plant Physiol., 136 (1990) 161-165.
39. M. Langmeier, S. Ginsburg and P. Matile, Chlorophyll breakdown in senescent leaves; demonstration of Mg-dechelatase activity, Physiol. Plant., 89 (1993) 347-353.
40. Y. Shioi, K. Watanabe, N. Tomita, T. Tsuchiya and K. Takamiya, New Substance and enzyme involving in breakdown of chlorophylls: properties of Mg-dechelating substance and pheophorbidase, paper presented at Tetrapyrrole Photoreceptors, June 5-10, 1995, Freising, Germany.
41. 2-Hydroxychlorophyll a, the first product of the reaction of chlorophyll-oxidase, J. Plant Physiol., 115 (1984) 85-89.
42. B. Lüthy, E. Martinoia, P. Matile and H. Thomas, Thylakoid-associated "chlorophyll oxidase": distinction from lipoxygenase, Z. Pflanzenphysiol. 113 (1984) 423-434.
43. B. Lüthy, P. Matile and H. Thomas, Properties of linolenic acid-dependent chlorophyll oxidation activity in thylakoid membranes, J. Plant Physiol., 123 (1986) 169-180.
44. L.G. Johnston and W.F. Watson, The allomerization of chlorophyll, J. Chem. Soc., (1956) 1203-1212, and references cited therein.
45. P. Matile, Catabolism of chlorophyll: involvement of peroxidase?, Z. Pflanzenphysiol., 99 (1980) 475-478.
46. E. Martinoia, M.J. Dalling and P. Matile, Catabolism of chlorophyll: demonstration of chloroplast-localized peroxidative and oxidative activities, Z. Pflanzenphysiol., 107 (1982) 269-279.
47. S. Ginsburg, M. Schellenberg and P. Matile, Cleavage of chlorophyll-porphyrin. Requirement for reduced ferredoxin and oxygen, Plant Physiol., 105 (1994) 545-554.
48. M. Schellenberg, P. Matile and H. Thomas, Breakdown of chlorophyll in chloroplasts of senescent barley leaves depends on ATP, J. Plant Physiol., 136 (1990) 564-568.
49. H. Thomas, B. Lüthy and P. Matile, Leaf senescence in a non-yellowing mutant of Festuca pratensis Huds., Planta, 164 (1985) 400-405.
50. B. Lüthy, H. Thomas and P. Matile, Linolenic acid-dependent Chlorophyll oxidase activity: a property of photosystem I and II, J. Plant Physiol., 123 (1986) 203-209.
51. S. Schoch and J. Brown, The action of chlorophyllase in chlorophyll-protein complexes, J. Plant Physiol., 126 (1987) 483-494.
52. N. Engel, T.A. Jenny, V. Mooser and A. Gossauer, Chlorophyll catabolism in Chlorella protothecoides. Isolation and structure elucidation of a red biline derivative, FEBS Lett., 293 (1991) 131-133.
53. B. Kräutler, B. Jaun, K. Bortlik, M. Schellenberg and P. Matile, On the enigma of chlorophyll degradation: The constitution of a secoporphinoid catabolite, Angew. Chem., 103 (1991) 1354-1357; Angew. Chem. Int. Ed. Engl., 30 (1991) 1315-1318.
54. B. Kräutler, B. Jaun, K. Bortlik, M. Schellenberg and P. Matile, On the enigma of chlorophyll degradation: The constitution of a secoporphinoid catabolite, Angew. Chem., 103 (1991) 1354-1357; Angew. Chem. Int. Ed. Engl., 30 (1991) 1315-1318.
55. B. Kräutler, B. Jaun, W. Amrein, K. Bortlik, M. Schellenberg and P. Matile, Breakdown of chlorophyll: Constitution of a secoporphinoid chlorophyll catabolite isolated from senescent barley leaves, Plant Physiol. Biochem., 30 (1992) 333-346.
56. N. Engel, A. Gossauer, K. Gruber and C. Kratky, X-Ray molecular structure of a red bilin derivative from Chlorella protothecoides, Helv. Chim. Acta, 76 (1993) 2236-2238.
57. J. Iturraspe and A. Gossauer, A biomimetical partial synthesis of a red chlorophyll-a catabolite from Chlorella protothecoides, Tetrahedron, 48 (1992) 6807-6812.
58. W. Mühlecker, B. Kräutler, S. Ginsburg and P. Matile, Breakdown of chlorophyll: a tetrapyrrolic chlorophyll catabolite from senescent rape leaves, Helv. Chim. Acta, 76 (1993) 2976-2980.
59. B. Kräutler, Breakdown of chlorophyll: the constitution of tetrapyrrolic chlorophyll catabolites from senescent plant leaves, Plant Physiol. Biochem., in press.
60. For a review see: R. Schmid and A.F. McDonagh in D. Dolphin (ed.), The Porphyrins, Academic Press, New York, 1979, Vol. VI, 257ff.
61. For a review see: S.I. Beale, Biosynthesis of Phycobilines, Chem. Rev., 95 (1993) 785-802.
62. A. Gossauer, Die Chemie der Pyrrole, Springer Verlag, 1974, 113ff.
63. A. Gossauer, Catabolism of Tetrapyrroles, Chimia, 48 (1994) 352-361.
64. R. Ziegler, A. Blaheta, N. Guha and B. Schönegge, Enzymatic formation of pheophorbide and pyropheophorbide during chloropyll degradation in a mutant of Chlorella fusca SHIHIRA et KRAUS, J. Plant Physiol., 132 (1988) 327-332.
65. N. Engel, C. Curty and A. Gossauer, Chlorophyll catabolism in Chlorella protothecoides: Facts and Artefacts, Plant Physiol. Biochem., in press.
66. J. Iturraspe, N. Engel and A. Gossauer, Chlorophyll catabolism. Isolation and structure elucidation of chlorophyll b catabolites in Chlorella protothecoides, Phytochemistry, 35 (1994) 1387-1390.
67. S. Hörtensteiner, F. Vincentini and P. Matile, Chlorophyll breakdown in senescent cotyledons of rape, Brassica napus L.; Enzymatic cleavage of phaeophorbide a in vitro, New Phytol., 129 (1995) 237-246.
68. H. Ito, Y. Tanaka, H. Tsuji and A. Tanaka, Conversion of chlorophyll b to chlorophyll a in isolated cucumber etioplasts, Arch. Biochem. Biophys., 306 (1993) 148-151.
69. H. Ito, S. Takaichi, H. Tsuji and A. Tanaka, Properties of synthesis of chlorophyll a from chlorophyll b in cucumber etioplasts, J. Biol. Chem., 269 (1994) 22034-22038.
70. 1OH] pheophorbide a in oat seedlings, paper presented at Tetrapyrrole Photoreceptors, June 5-10, 1995, Freising, Germany.
71. F.T. Wolf, Changes in chlorophyll a and b in autumn leaves, Am. J. Bot., 43 (1956) 714-718.
72. J.E. Sanger, Quantitative investigations of leaf pigments from their inception in buds through autumn coloration to decomposition in falling leaves, Ecology, 52 (1971) 1075-1089.
73. J. Iturraspe and A. Gossauer, Formation of oxoniachlorins on photooxydation of 20-trifluoroacetoxy- and 20-chloro-chlorophyll derivatives, Photochem. Photobiol., 54 (1991) 43-49.
74. J. Iturraspe and A. Gossauer, Dependence of the regioselectivity of photo-oxidative ring opening of the chlorophyll macrocycle on the complexed metal ion, Helv. Chim. Acta, 74 (1991) 1713-1717.
75. C. Curty, N. Engel, J. Iturraspe and A. Gossauer, Mechanism of photo-oxygenation of the Cd(II) complex of pyropheophorbide a methyl ester, Photochem. Photobiol., 61 (1995) 552-556.
76. C. Curty, N. Engel and A. Gossauer, Evidence for a monooxygenase-catalyzed primary process in the catabolism of chlorophyll, FEBS Lett., 364 (1995) 41-44.
77. C. van den Hoek, H.M. Jahns and D.G. Mann, Algen, 3rd ed., G. Thieme Verlag, Stuttgart, 1993, Chap. 30.
78. T. Düggelin, M. Schellenberg, K. Bortlik and P. Matile, Vacuolar location of Lipofuscin- and prolin-like compounds in senescent barley leaves, J. Plant Physiol., 133 (1988) 492-497.
79. M. Schellenberg, P. Matile and H. Thomas, Production of a presumptive chlorophyll catabolite in vitro: requirement for reduced ferredoxin, Planta, 191 (1993) 417-120.
80. S. Ginsburg and P. Matile, Identification of catabolites of chlorophyll-porphyrin in senescent rape cotyledons, Plant Physiol., 102 (1993) 521-527.
81. P. Matile, S. Ginsburg, M. Schellenberg and H. Thomas, Catabolites of chlorophyll in senescing barley leaves are localized in the vacuoles of mesophyll cells, Proc. Natl. Acad. Sci. USA, 85 (1988) 9529-9532.
82. J. Iturraspe, N. Engel, P. Matzinger, V. Mooser and A. Gossauer, Chlorophyll catabolism. Part 3. Structure elucidation and partial synthesis of a new red bilin derivative from Chlorella protothecoides, Photochem. Photobiol., 58 (1993) 116-119.