Food plants contain hundreds of bioactive phytochemicals arising from different secondary metabolic pathways. Among these, the metabolic route of the amino acid Tryptophan yields a large number of plant natural products with chemically and pharmacologically diverse properties. We propose the identifier "indolome" to collect all metabolites in the Tryptophan pathway. In addition, Tryptophan-rich plant sources can be used as substrates for the fermentation by yeast strains to produce pharmacologically active metabolites, such as Melatonin. To pursue this technological development, we have developed a UHPLC-MS/MS method to monitor 14 Tryptophan, Tryptamine, amino-benzoic, and pyridine metabolites. In addition, different extraction procedures to improve the recovery of Tryptophan and its derivatives from the vegetal matrix were tested. We investigated soybeans, pumpkin seeds, sesame seeds, and spirulina because of their botanical diversity and documented healthy effects. Four different extractions with different solvents and temperatures were tested, and water extraction at room temperature was chosen as the most suitable procedure to extract the whole Tryptophan metabolites pattern (called by us "indolome") in terms of ease, high efficiency, short time, low cost, and sustainability. In all plant matrices, Tryptophan was the most abundant indole compound, while the pattern of its metabolites was different in the diverse plants extracts. Overall, 5-OH Tryptamine and Kynurenine were the most abundant compounds, despite being 100-1000-fold lower than Tryptophan. Melatonin was undetected in all extracts, but sesame showed the presence of a Melatonin isomer. The results of this study highlight the variability in the occurrence of indole compounds among diverse food plants. The knowledge of Tryptophan metabolism in plants represents a relevant issue for human health and nutrition.

LC-MS/MS-Based Profiling of Tryptophan-Related Metabolites in Healthy Plant Foods / S. Vitalini, M. Dei Cas, F.M. Rubino, I. Vigentini, R. Foschino, M. Iriti, R. Paroni. - In: MOLECULES. - ISSN 1420-3049. - 25:2(2020 Jan 13). [10.3390/molecules25020311]

LC-MS/MS-Based Profiling of Tryptophan-Related Metabolites in Healthy Plant Foods

S. Vitalini
Co-primo
Methodology
;
M. Dei Cas
Co-primo
Methodology
;
F.M. Rubino
Secondo
Data Curation
;
I. Vigentini
Methodology
;
R. Foschino
Funding Acquisition
;
M. Iriti
Penultimo
Project Administration
;
R. Paroni
Ultimo
Writing – Review & Editing
2020

Abstract

Food plants contain hundreds of bioactive phytochemicals arising from different secondary metabolic pathways. Among these, the metabolic route of the amino acid Tryptophan yields a large number of plant natural products with chemically and pharmacologically diverse properties. We propose the identifier "indolome" to collect all metabolites in the Tryptophan pathway. In addition, Tryptophan-rich plant sources can be used as substrates for the fermentation by yeast strains to produce pharmacologically active metabolites, such as Melatonin. To pursue this technological development, we have developed a UHPLC-MS/MS method to monitor 14 Tryptophan, Tryptamine, amino-benzoic, and pyridine metabolites. In addition, different extraction procedures to improve the recovery of Tryptophan and its derivatives from the vegetal matrix were tested. We investigated soybeans, pumpkin seeds, sesame seeds, and spirulina because of their botanical diversity and documented healthy effects. Four different extractions with different solvents and temperatures were tested, and water extraction at room temperature was chosen as the most suitable procedure to extract the whole Tryptophan metabolites pattern (called by us "indolome") in terms of ease, high efficiency, short time, low cost, and sustainability. In all plant matrices, Tryptophan was the most abundant indole compound, while the pattern of its metabolites was different in the diverse plants extracts. Overall, 5-OH Tryptamine and Kynurenine were the most abundant compounds, despite being 100-1000-fold lower than Tryptophan. Melatonin was undetected in all extracts, but sesame showed the presence of a Melatonin isomer. The results of this study highlight the variability in the occurrence of indole compounds among diverse food plants. The knowledge of Tryptophan metabolism in plants represents a relevant issue for human health and nutrition.
Pumpkin; Sesame; Spirulina; Tryptamine; Tryptophan; functional foods; indole compounds; mass spectrometry; matrix extraction; nutraceuticals; soya
Settore BIO/12 - Biochimica Clinica e Biologia Molecolare Clinica
Settore AGR/12 - Patologia Vegetale
Settore AGR/16 - Microbiologia Agraria
Settore BIO/10 - Biochimica
   Semilavorati nutraceutici e tecnologici fermentati per il miglioramento nutrizionale di prodotti da forno tradizionali gluten-free
   REGIONE LOMBARDIA
   ID 145007
13-gen-2020
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/708919
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