Melatonin in higher plants: Occurrence and possible functions

Journal of Pineal Research

Volumn 39, Issue 4, 2005, Pages 333-341

  Kolář, Jan ^a   Macháčková, Ivana ^a  

^a INSTITUTE OF EXPERIMENTAL BOTANY   (Czech Republic)

Author keywords

Antioxidant; Circadian rhythms; Higher plants; Melatonin; Melatonin determination; Photoperiodism; Reactive oxygen species

Indexed keywords

ANTIOXIDANT; AUXIN; MELATONIN; PHYTOHORMONE;

DINOFLAGELLATE; GAS CHROMATOGRAPHY; HERBIVORY; HORMONE ACTION; HORMONE DETERMINATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHOTOPERIODICITY; RELIABILITY; SHORT SURVEY; ANIMAL; CHEMISTRY; CIRCADIAN RHYTHM; DRUG EFFECT; MASS FRAGMENTOGRAPHY; METABOLISM; PHYSIOLOGY; PLANT; REVIEW;

ANIMALS; ANTIOXIDANTS; CHROMATOGRAPHY, LIQUID; CIRCADIAN RHYTHM; DINOFLAGELLIDA; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MELATONIN; PHOTOPERIOD; PLANT GROWTH REGULATORS; PLANTS;

EID: 27744508271     PISSN: 07423098     EISSN: 1600079X     Source Type: Journal    
DOI: 10.1111/j.1600-079X.2005.00276.x     Document Type: Short Survey

References (106)

1. Lerner AB Chase JD Takahashi Y et al. Isolation of melatonin, the pineal factor that lightens melanocytes. J Am Chem Soc 1958 80 : 2587
2. Brainard GC Petterborg LJ Richardson BA et al. Pineal melatonin in Syrian hamsters: circadian and seasonal rhythms in animals maintained under laboratory and natural conditions. Neuroendocrinology 1982 35 : 342 348.
3. Lewy AJ. Melatonin as a marker and phase-resetter of circadian rhythms in humans. In : Melatonin After Four Decades: An Assessment of its Potential. Olcese J, ed. Kluwer Academic/Plenum Publishers, New York, 2000 pp. 425 434.
4. Mayer I Bornestaf C Borg B. Melatonin in non-mammalian vertebrates: physiological role in reproduction? Comp Biochem Physiol [A] 1997 118 : 515 531.
5. Mayer I Elofsson H Bergman U et al. Diel plasma melatonin profile in a cyclostome, the river lamprey. J Fish Biol 1998 53 : 906 909.
6. Hardeland R Fuhrberg B. Ubiquitous melatonin - presence and effects in unicells, plants and animals. Trends Comp Biochem Physiol 1996 2 : 25 45.
7. Vivien-Roels B Pevet P. Melatonin: presence and formation in invertebrates. Experientia 1993 49 : 642 647.
8. Hardeland R Poeggeler B. Non-vertebrate melatonin. J Pineal Res 2003 34 : 233 241.
9. Poeggeler B Balzer I Hardeland R et al. Pineal hormone melatonin oscillates also in the dinoflagellate Gonyaulax polyedra. Naturwissenschaften 1991 78 : 268 269.
10. Hardeland R. Melatonin and 5-methoxytryptamine in non-metazoans. Reprod Nutr Develop 1999 39 : 399 408.
11. Dubbels R Reiter RJ Klenke E et al. Melatonin in edible plants identified by radioimmunoassay and by high performance liquid chromatography-mass spectrometry. J Pineal Res 1995 18 : 28 31.
12. Hattori A Migitaka H Iigo M et al. Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int 1995 35 : 627 634.
13. Van Tassel DL Roberts NJ O'Neill SD. Melatonin from higher plants: isolation and identification of N-acetyl-5-methoxytryptamine. Plant Physiol 1995 108 ( Suppl. 101.
14. Manchester LC Tan DX Reiter RJ et al. High levels of melatonin in the seeds of edible plants. Possible function in germ tissue protection. Life Sci 2000 67 : 3023 3029.
15. Burkhardt S Tan DX Manchester LC et al. Detection and quantification of the antioxidant melatonin in Montmorency and Balaton tart cherries (Prunus cerasus). J Agric Food Chem 2001 49 : 4898 4902.
16. Poeggeler B Hardeland R. Detection and quantification of melatonin in a dinoflagellate, Gonyaulax polyedra: solutions to the problem of methoxyindole destruction in non-vertebrate material. J Pineal Res 1994 17 : 1 10.
17. Van Tassel DL. Identification and Quantification of Melatonin in Higher Plants, Ph.D. thesis. University of California, Davis, California, USA, 1997.
18. Van Tassel DL Roberts N Lewy A et al. Melatonin in plant organs. J Pineal Res 2001 31 : 8 15.
19. Murch SJ Krishnaraj S Saxena PK. Tryptophan is a precursor for melatonin and serotonin biosynthesis in in vitro regenerated St. John's wort (Hypericum perforatum L. cv. Anthos) plants. Plant Cell Rep 2000 19 : 698 704.
20. Fuhrberg B Balzer I Hardeland R et al. The vertebrate pineal hormone melatonin is produced by the brown alga Pterygophora californica and mimics dark effects on growth rate in the light. Planta 1996 200 : 125 131.
21. Kolář J Macháčková I Eder J et al. Melatonin: occurrence and daily rhythm in Chenopodium rubrum. Phytochemistry 1997 44 : 1407 1413.
22. Hernández-Ruiz J Cano A Arnao MB. Melatonin: a growth-stimulating compound present in lupin tissues. Planta 2004 220 : 140 144.
23. Van Tassel DL O'Neill SD. Putative regulatory molecules in plants: evaluating melatonin. J Pineal Res 2001 31 : 1 7.
24. Kolář J. The Daily Rhythm of Melatonin in Chenopodium rubrum Plants - in Czech, MSc thesis. Faculty of Natural Sciences, Charles University, Prague, Czech Republic, 1996.
25. Wolf K kolář J Witters E et al. Daily profile of melatonin levels in Chenopodium rubrum L. depends on photoperiod. J Plant Physiol 2001 158 : 1491 1493.
26. Kolář J. Effects of Melatonin on Circadian Rhythms and Photoperiodism in Higher Plants, PhD thesis. Faculty of Natural Sciences, Charles University, Prague, Czech Republic, 2003.
27. Rolčík J Lenobel R Siglerová V et al. Isolation of melatonin by immunoaffinity chromatography. J Chromatogr B 2002 775 : 9 15.
28. Vaňková R Gaudinová A Süssenbeková H et al. Comparison of oriented and random antibody immobilization in immunoaffinity chromatography of cytokinins. J Chromatogr A 1998 811 : 77 84.
29. Sundberg B Sandberg G Crozier A. Purification of indole-3-acetic acid in plant extracts by immunoaffinity chromatography. Phytochemistry 1986 25 : 295 298.
30. Chen G Huo Y Tan DX et al. Melatonin in Chinese medicinal herbs. Life Sci 2003 73 : 19 26.
31. Maywood ES Hastings MH Max M et al. Circadian and daily rhythms of melatonin in the blood and pineal gland of free-running and entrained Syrian hamsters. J Endocr 1993 136 : 65 73.
32. Menaker M Wisner S. Temperature-compensated circadian clock in the pineal of Anolis. Proc Natl Acad Sci USA 1983 80 : 6119 6121.
33. Vondrašová-Jelínková D Hájek I Illnerová H. Adjustment of the human melatonin and cortisol rhythms to shortening of the natural summer photoperiod. Brain Res 1999 816 : 249 253.
34. Lewy AJ Markey SP. Analysis of melatonin in human plasma by gas chromatography negative chemical ionization mass spectrometry. Science 1978 201 : 741 743.
35. Wong PSH Yoshioka K Xie F et al. In vivo microdialysis liquid chromatography tandem mass spectrometry for the on-line monitoring of melatonin in rat. Rapid Commun Mass Spectrom 1999 13 : 407 411.
36. Mei H Hsieh YS Nardo C et al. Investigation of matrix effects in bioanalytical high-performance liquid chromatography/tandem mass spectrometric assays: application to drug discovery. Rapid Commun Mass Spectrom 2003 17 : 97 103.
37. Smeraglia J Baldrey SF Watson D. Matrix effects and selectivity issues in LC-MS-MS. Chromatographia 2002 55 : S95 S99.
38. Matuszewski BK Constanzer ML Chavez-Eng CM. Matrix effect in quantitative LC/MS/MS analyses of biological fluids: a method for determination of finasteride in human plasma at picogram per milliliter concentrations. Anal Chem 1998 70 : 882 889.
39. Fu I Woolf EJ Matuszewski BK. Effect of the sample matrix on the determination of indinavir in human urine by HPLC with turbo ion spray tandem mass spectrometric detection. J Pharm Biomed Anal 1998 18 : 347 357.
40. Sugden D. Melatonin biosynthesis in the mammalian pineal gland. Experientia 1989 45 : 922 932.
41. Reiter RJ. The melatonin rhythm: both a clock and a calendar. Experientia 1993 49 : 654 664.
42. Cassone VM. Effects of melatonin on vertebrate circadian systems. Trends Neurosci 1990 13 : 457 464.
43. Pévet P Bothorel B Slotten H et al. The chronobiotic properties of melatonin. Cell Tissue Res 2002 309 : 183 191.
44. Bartness TJ Goldman BD. Mammalian pineal melatonin: a clock for all seasons. Experientia 1989 45 : 939 945.
45. Goldman BD. Mammalian photoperiodic system: formal properties and neuroendocrine mechanisms of photoperiodic time measurement. J Biol Rhythm 2001 16 : 283 301.
46. Balzer I Bartolomaeus B Höcker B. Circadian Rhythm of Melatonin Content in Chlorophyceae. Abstracts of the Workshop of the European Society for Chronobiology: News From the Plant Chronobiology Research. Markgrafenheide, Germany, 1998.
47. Lüning K Kadel P. Circatidal Control of Melatonin Content in a Marine Organism: Melatonin Peaks at Night at High Water in the Intertidal Red Macroalga Porphyra umbilicalis. Abstracts of the Second Workshop of the European Society for Chronobiology: News From the Plant Chronobiology Research. Markgrafenheide, Germany, 2000.
48. Balzer I Hardeland R. Photoperiodism and effects of indoleamines in a unicellular alga, Gonyaulax polyedra. Science 1991 253 : 795 797.
49. Fischer J Hardeland R. Melatonin resets the circadian oscillator in Pyrocystis acuta. In : Cell Biological Problems in Chronobiology. Hardeland R, ed. Universitaet Goettingen, Goettingen, 1994 pp. 71 74.
50. Hardeland R. Melatonin and 5-methoxytryptamine did not mediate short-day effects in the Lemnacean species Spirodela polyrhiza, Lemna minor and Lemna trisulca. In : Cell Biological Problems in Chronobiology. Hardeland R, ed. Universitaet Goettingen, Goettingen, 1994 pp. 136 137.
51. Wolf K. Circadian Oscillations of Melatonin in Chenopodium rubrum plants - in Czech, MSc thesis. Faculty of Natural Sciences, Charles University, Prague, Czech Republic, 2000.
52. Kolář J Johnson CH Macháčková I. Exogenously applied melatonin (N-acetyl-5-methoxytryptamine) affects flowering of the short-day plant Chenopodium rubrum. Physiol Plant 2003 118 : 605 612.
53. Cumming BG Seabrook JEA. Chenopodium. In : CRC Handbook of Flowering. Halevy AH, ed. CRC Press, Boca Raton, 1985 pp. 196 228.
54. 3H-melatonin to calmodulin. Life Sci 1993 53 : 201 207.
55. 2+/calmodulin-dependent kinase II activity by melatonin. Biochim Biophys Acta 1996 1290 : 191 196.
56. Antón-Tay F Martínez I Tovar R et al. Modulation of the subcellular distribution of calmodulin by melatonin in MDCK cells. J Pineal Res 1998 24 : 35 42.
57. Pozo D Reiter RJ Calvo JR et al. Physiological concentrations of melatonin inhibit nitric oxide synthase in rat cerebellum. Life Sci 1994 55 : PL455 PL460.
58. Wölfler A Schauenstein K Liebmann PM. Lack of calmodulin antagonism of melatonin in T-lymphocyte activation. Life Sci 1998 63 : 835 842.
59. Snedden WA Fromm H. Calmodulin as a versatile calcium signal transducer in plants. New Phytol 2001 151 : 35 66.
60. Benítez-King G Antón-Tay F. Calmodulin mediates melatonin cytoskeletal effects. Experientia 1993 49 : 635 641.
61. Jackson WT. Regulation of mitosis II. Interaction of isopropyl-N-phenyl- carbamate and melatonin. J Cell Sci 1969 5 : 745 755.
62. Banerjee S Margulis L. Mitotic arrest by melatonin. Exp Cell Res 1973 78 : 314 318.
63. Reiter RJ Tan DX Osuna C et al. Actions of melatonin in the reduction of oxidative stress. A review. J Biomed Res 2000 7 : 444 458.
64. Reiter RJ Tan DX Mayo JC et al. Melatonin as an antioxidant: biochemical mechanisms and pathophysiological implications in humans. Acta Biochim Polon 2003 50 : 1129 1146.
65. Tan DX Reiter RJ Manchester LC et al. Chemical and physical properties and potential mechanisms: melatonin as a broad spectrum antioxidant and free radical scavenger. Curr Top Med Chem 2002 2 : 181 197.
66. Rodriguez C Mayo JC Sainz RM et al. Regulation of antioxidant enzymes: a significant role for melatonin. J Pineal Res 2004 36 : 1 9.
67. Tan DX Manchester LC Hardeland R et al. Melatonin: a hormone, a tissue factor, an autocoid, a paracoid, and an antioxidant vitamin. J Pineal Res 2003 34 : 75 78.
68. Tan DX Chen LD Poeggeler B et al. Melatonin: a potent endogenous hydroxyl radical scavenger. Endocrine J 1993 1 : 57 60.
69. Tan DX Manchester LC Reiter RJ et al. Melatonin directly scavenges hydrogen peroxide: a potentially new metabolic pathway of melatonin biotransformation. Free Radical Biol Med 2000 29 : 1177 1185.
70. 2 -formyl-5-methoxykynuramine, quercetin or resveratrol. J Pineal Res 2005 38 : 107 115.
71. Poeggeler B Reiter RJ Hardeland R et al. Melatonin and structurally related endogenous indoles act as potent electron donors and radical scavengers in vitro. Redox Rep 1996 2 : 179 184.
72. Zhang H Squadrito GI Pryor WA. The reaction of melatonin with peroxynitrite: formation of melatonin radical cation and absence of stable nitrated products. Biochem Biophys Res Commun 1998 25 : 83 87.
73. Mahal HS Sharma HS Mukherjee T. Antioxidant properties of melatonin: a pulse radiolysis study. Free Radical Biol Med 1999 26 : 577 585.
74. Marshall KA Reiter RJ Poeggeler B. Evaluation of the antioxidant activity of melatonin in vitro. Free Radical Biol Med 1996 21 : 307 315.
75. Mayo JC Sainz RM Antolín I et al. Melatonin regulation of antioxidant enzyme gene expression. Cell Mol Life Sci 2002 59 : 1706 1713.
76. Urata Y Honma S Goto S et al. Melatonin induces γ-glutamylcysteine synthetase mediated by activator portein-1 in human vascular endothelial cells. Free Rad Biol Med 1999 27 : 838 847.
77. Baydas G Gursu MF Yilmaz S et al. Daily rhythm of glutathione peroxidase activity, lipid peroxidation and glutathione levels in tissues of pinealectomized rats. Neurosci Lett 2002 323 : 195 198
78. Antolin I Rodriguez C Sainz RM et al. Neurohormone melatonin prevents cell damage: effect on gene expression for antioxidant enzymes. FASEB J 1996 10 : 882 890.
79. Jou MJ Peng TI Reiter RJ et al. Visualization of the antioxidative effects of melatonin at the mitochondrial level during oxidative stress-induced apoptosis of rat brain astrocytes. J Pineal Res 2004 37 : 55 70.
80. Pappolla MA Chyan YJ Poegeller B et al. An assessment of the antioxidant and antiamyloidogenic properties of melatonin: implications for Alzheimer's disease. J Neural Transm 2000 107 : 203 231.
81. Pappolla MA Reiter RJ Bryant-Thomas TK et al. Oxidative mediated neurodegeneration in Alzheimer's disease: melatonin and related antioxidants as neuroprotective agents. Curr Med Chem 2003 3 : 233 243.
82. Gitto E Karbownik M Reiter RJ et al. Effects of melatonin treatment in septic newborns. Pediat Res 2001 50 : 756 760.
83. Gitto E Reiter RJ Karbownik M et al. Respiratory distress syndrome in the newborn: role of oxidative stress. Intens Care Med 2001 27 : 1116 1123.
84. Poon AMS Pang SF. 2[125I] iodomelatonin binding sites in spleens of guinea pigs. Life Sci 1992 50 : 1719 1726.
85. Acuna-Castroviejo D Escames G Carozo A et al. Melatonin, mitochondrial homeostasis and mitochondrial-related diseases. Curr Top Med Chem 2002 2 : 133 152.
86. Martin M Macias M Escames G et al. Melatonin but not vitamins C and E maintains glutathione homeostasis in t-butylhydroperoxide induced mitochondrial oxidative stress. FASEB J 2000 14 : 1677 1679.
87. Martin M Macias M Leon J et al. Melatonin increases the activity of oxidative phosphorylation enzymes and the production of ATP in rat brain and liver mitochondria. Int J Biochem Cell Biol 2001 1212 : 1 10.
88. Leon J Acuna-Castroviejo D Escames G et al. Melatonin mitigates mitochondrial malfunction. J Pineal Res 2005 38 : 1 9.
89. Lopez-Burillo S Tan DX Mayo JC et al. Melatonin, xanthurenic acid, resveratrol, EGCG, vitamin C and alpha-lipoic acid differentially reduce oxidative DNA damage induced by Fenton reagents: a study of their individual and synergistic actions. J Pineal Res 2003 34 : 269 277.
90. Antolín I Hardeland R. Suppression of the Gonyaulax glow peak by paraquat and its restoration by melatonin. In : Biological Rhythms and Antioxidative Protection. Hardeland R, ed. Cuvillier, Goettingen, 1997 pp. 86 97.
91. Hardeland R Burkhardt S Antolín I et al. Melatonin and 5-methoxytryptamine in the bioluminescent dinoflagellate Gonyaulax polyedra: restoration of the circadian glow peak after suppression of indoleamine biosynthesis or oxidative stress. In : Melatonin After Four Decades: An Assessment of Its Potential. Olcese J, ed. Kluwer Academic/Plenum Publishers, New York, 2000 pp. 387 390.
92. Fletcher RA Sopher C. Retardation of Leaf Senescence by Melatonin Indicates that it Acts as an Antioxidant in Plants. 5th Canadian Pineal and Melatonin Symposium, Guelph, 1997 Abstract No. 7.
93. Katekar GF. Auxins: on the nature of the receptor site and molecular requirements for auxin activity. Phytochemistry 1979 18 : 223 233.
94. Edmonds K Riggs N Spurrier R. Effects of Melatonin and Auxin Administration on Growth in Arabidopsis thaliana and Coleus and on Testicular Development in Rice Rats. Abstracts of the Seventh Meeting of the Society for Research on Biological Rhythms, Jacksonville, FL, USA, 2000.
95. Hardeland R Reiter RJ Poeggeler B et al. The significance of the metabolism of the neurohormone melatonin: antioxidative protection and formation of bioactive substances. Neurosci Biobehav Rev 1993 17 : 347 357.
96. Murch SJ Campbell SS Saxena PK. The role of serotonin and melatonin in plant morphogenesis: regulation of auxin-induced root organogenesis in in vitro-cultured explants of St. John's wort (Hypericum perforatum L.). In Vitro Cell Dev Biol - Plant 2001 37 : 786 793.
97. Reiter RJ Tan DX Burkhardt S et al. Melatonin in plants. Nutr Rev 2001 59 : 286 290.
98. Reiter RJ Manchester LC Tan DX. Melatonin in walnuts: influence on levels of melatonin and total antioxidant capacity of blood. Nutrition 2005 21 : 920 924.
99. Finocchiaro L Callebert J Launay JM et al. Melatonin biosynthesis in Drosophila: its nature and its effects. J Neurochem 1988 50 : 382 387.
100. Thomas JC Saleh EF Alammar N et al. The indole alkaloid tryptamine impairs reproduction in Drosophila melanogaster. J Econ Entomol 1998 91 : 841 846.
101. Thomas JC Adams DG Nessler CL et al. Tryptophan decarboxylase, tryptamine, and reproduction of the whitefly. Plant Physiol 1995 109 : 717 720.
102. Brusco LI Marquez M Cardinali DP. Monozygotic twins with Alzheimer's disease treated with melatonin: case report. J Pineal Res 1998 25 : 260 263.
103. Blask DE Dauchy RT Sauer LA. Melatonin uptake and growth prevention in rat hepatoma 7288CTC in response to dietary melatonin: melatonin receptor-mediated inhibition of tumor linoleic acid metabolism to the growth signaling molecule 13-hydroxyoctadecadienoic acid and the potential role of phytomelatonin. Carcinogenesis 2004 25 : 951 960.
104. Murch SJ Saxena PK. Mammalian neurohormones: potential significance in reproductive physiology of St. John's Wort (Hypericum perforatum L.)? Naturwissenschaften 2002 89 : 555 560.
105. Murch SJ Simmons CB Saxena PK. Melatonin in feverfew and other medicinal plants. Lancet 1997 350 : 1598 1599.
106. Murch SJ Vasantha Rupasinghe HP Goodenowe D et al. A metabolomic analysis of medicinal diversity in Huang-qin (Scutellaria baicalensis Georgi) genotypes: discovery of novel compounds. Plant Cell Rep 2004 23 : 419 425.