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Novel rhythms of N¹-acetyl-N²-formyl-5-methoxykynuramine and its precursor melatonin in water hyacinth: importance for phytoremediation

Dun-Xian Tan^*,1, Lucien C. Manchester^,1, Paolo Di Mascio^,2, Glaucia R. Martinez, Fernanda M. Prado and Russel J. Reiter^*,3

^* Department of Cellular Structural Biology, The University of Texas, Health Science Center, San Antonio, Texas, USA;

Department of Biological Sciences, St Mary’s University, San Antonio, Texas, USA; and

Departamento de Bioquímica, Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil

³Correspondence: Department of Cellular Structural Biology, The University of Texas Health Science Center, 7703 Floyd Curl Dr., San Antonio, TX, 78229, USA. E-mail: reiter{at}uthscsa.edu

N¹-acetyl-N²-formyl-5-methoxykynuramine (AMFK) is a major metabolite of melatonin in mammals. To investigate whether AFMK exists in plants, an aquatic plant, water hyacinth, was used. To achieve this, LC/MS/MS with a deuterated standard was employed. AFMK was identified in any plant for the first time. Both it and its precursor, melatonin, were rhythmic with peaks during the late light phase. These novel rhythms indicate that these molecules do not serve as the chemical signal of darkness as in animals but may relate to processes of photosynthesis or photoprotection. These possibilities are supported by higher production of melatonin and AFMK in plants grown in sunlight (10,000–15,000 µW/cm²) compared to those grown under artificial light (400–450 µW/cm²). Melatonin and AFMK, as potent free radical scavengers, may assist plants in coping with harsh environmental insults, including soil and water pollutants. High levels of melatonin and AFMK in water hyacinth may explain why this plant more easily tolerates environmental pollutants, including toxic chemicals and heavy metals and is successfully used in phytoremediation. These novel findings could lead to improvements in the phytoremediative capacity of plants by either stimulating endogenous melatonin synthesis or by adding melatonin to water/soil in which they are grown.—Dun-Xian Tan, Lucien C. Manchester, Paolo Di Mascio, Glaucia R. Martinez, Fernanda M. Prado, and Russel J. Reiter. Novel rhythms of N¹-acetyl-N²-formyl-5-methoxykynuramine and its precursor melatonin in water hyacinth: importance for phytoremediation.

Key Words: plant • AFMK • circadian rhythm • antioxidant