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Intracellular biosynthesis of melatonin and other indolic compounds in Saccharomyces and non-Saccharomyces wine yeasts

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Abstract

Certain bioactive compounds that derive from tryptophan have been determined in fermented foods, which suggests that the role of yeast is putative in origin. Melatonin is a neurohormone in humans that plays an important role in health. The activity of other compounds, such as 3-indoleacetic acid, has been recently highlighted, and interest in elucidating the conditions of their production has grown. However, the biosynthesis of melatonin by yeasts remains unclear to a large extent. Therefore, this work was undertaken to demonstrate the unequivocal synthesis of melatonin and other compounds that derive from tryptophan metabolism by yeast by determining them in the intracellular compartment. By high-resolution mass spectrometry and a validated method, tryptophan itself, melatonin, serotonin, N-acetyl-5-hydroxytryptamine and 3-indoleacetic acid, were identified in the intracellular compartment of Saccharomyces and non-Saccharomyces wine yeasts.

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Abbreviations

5-HT:

Serotonin

5-HTRP:

5-Hydroxytryptophan

l-TRP:

l-tryptophan

TRYP:

Tryptamine

N-acetyl-5-HT:

N-acetyl-5-hydroxytryptamine

l-TRP EE:

l-tryptophan ethyl ester

TOL:

Tryptophol

3IAA:

3-Indoleacetic acid

MLT:

Melatonin

References

  1. Stürtz M, Cerezo AB, Cantos-Villar E, Garcia-Parrilla MC (2011) Determination of the melatonin content of different varieties of tomatoes (Lycopersicon esculentum) and strawberries (Fragaria ananassa). Food Chem 127:1329–1334

    Article  CAS  PubMed  Google Scholar 

  2. González-Gómez D, Lozano M, Fernández-León MF et al (2009) Detection and quantification of melatonin and serotonin in eight Sweet Cherry cultivars (Prunus avium L.). Eur Food Res Technol 229:223–229

    Article  CAS  Google Scholar 

  3. Garrido M, Gonzalez-Gomez D, Lozano M et al (2013) A Jerte Valley cherry product provides beneficial effects on sleep quality. Influence on aging. J Nutr Heal Aging 17:553–560

    Article  CAS  Google Scholar 

  4. Maldonado MD, Moreno H, Calvo JR (2009) Melatonin present in beer contributes to increase the levels of melatonin and antioxidant capacity of the human serum. Clin Nutr 28:188–191

    Article  CAS  PubMed  Google Scholar 

  5. Mercolini L, Saracino MA, Bugamelli F et al (2008) HPLC-F analysis of melatonin and resveratrol isomers in wine using an SPE procedure. J Sep Sci 31:1007–1014

    Article  CAS  PubMed  Google Scholar 

  6. Rodriguez-Naranjo MI, Gil-Izquierdo A, Troncoso AM et al (2011) Melatonin: a new bioactive compound in wine. J Food Compos Anal 24:603–608

    Article  CAS  Google Scholar 

  7. Rodriguez-Naranjo MI, Torija MJ, Mas A et al (2012) Production of melatonin by Saccharomyces strains under growth and fermentation conditions. J Pineal Res 53:219–224

    Article  CAS  PubMed  Google Scholar 

  8. Fernández-Pachón MS, Medina S, Herrero-Martín G et al (2014) Alcoholic fermentation induces melatonin synthesis in orange juice. J Pineal Res 56:31–38

    Article  CAS  PubMed  Google Scholar 

  9. Vázquez J, González B, Sempere V et al (2017) Melatonin reduces oxidative stress damage induced by hydrogen peroxide in Saccharomyces cerevisiae. Front Microbiol 8:1–14

    Google Scholar 

  10. Bisquert R, Muñiz-Calvo S, Guillamón JM (2018) Protective role of intracellular melatonin against oxidative stress and UV radiation in Saccharomyces cerevisiae. Front Microbiol 9:1–11

    Article  Google Scholar 

  11. Vigentini I, Gardana C, Fracassetti D et al (2015) Yeast contribution to melatonin, melatonin isomers and tryptophan ethyl ester during alcoholic fermentation of grape musts. J Pineal Res 58:388–396

    Article  CAS  PubMed  Google Scholar 

  12. Gil C, Gómez-Cordovés C (1986) Tryptophol content of young wines made from Tempranillo, Garnacha, Viura and Airén grapes. Food Chem 22:59–65

    Article  CAS  Google Scholar 

  13. Maslov L, Jeromel A, Herjavec S et al (2011) Indole-3-acetic acid and tryptophan in Istrian Malvasia grapes and wine. J Food Agric Environ 9:29–33

    CAS  Google Scholar 

  14. Gil-Agustí M, Carda-Broch S, Monferrer-Pons L, Esteve-Romero J (2007) Simultaneous determination of tyramine and tryptamine and their precursor amino acids by micellar liquid chromatography and pulsed amperometric detection in wines. J Chromatogr A 1156:288–295

    Article  CAS  PubMed  Google Scholar 

  15. Sprenger J, Hardeland R, Fuhrberg B, Han SZ (1999) Melatonin and other 5-methoxylated indoles in yeast: Presence in high concentrations and dependence on tryptophan availability. Cytologia (Tokyo) 64:209–213

    Article  CAS  Google Scholar 

  16. Fernández-Cruz E, Álvarez-Fernández MA, Valero E et al (2016) Validation of an analytical method to determine melatonin and compounds related to l-tryptophan metabolism using UHPLC/HRMS. Food Anal Methods 9:3327–3336

    Article  Google Scholar 

  17. Riou C, Nicaud J, Barre P, Gaillardin C (1997) Stationary-phase gene expression in saccharomyces cerevisiae during wine fermentation. Yeast 915:903–915

    Article  Google Scholar 

  18. Gonzalez B, François J, Renaud M (1997) A rapid and reliable method for metabolite extraction in yeast using boiling buffered ethanol. Yeast 13:1347–1356

    Article  CAS  PubMed  Google Scholar 

  19. Mas A, Guillamon JM, Torija MJ et al (2014) Bioactive compounds derived from the yeast metabolism of aromatic amino acids during alcoholic fermentation. Biomed Res Int 2014:1–7

    Article  Google Scholar 

  20. Prusty R, Grisafi P, Fink GR (2004) The plant hormone indoleacetic acid induces invasive growth in Saccharomyces cerevisiae. Proc Natl Acad Sci U S A 101:4153–4157

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. González B, Vázquez J, Cullen PJ et al (2018) Aromatic amino acid-derived compounds induce morphological changes and modulate the cell growth of wine yeast species. Front Microbiol 9:1–16

    Article  Google Scholar 

  22. Gardana C, Iriti M, Stuknyte M et al (2014) “Melatonin isomer” in wine is not an isomer of the melatonin but tryptophan-ethylester. J Pineal Res 57:435–441

    Article  CAS  PubMed  Google Scholar 

  23. Fernández-Cruz E, Álvarez-Fernández MA, Valero E et al (2017) Melatonin and derived l-tryptophan metabolites produced during alcoholic fermentation by different wine yeast strains. Food Chem 217:431–437

    Article  CAS  PubMed  Google Scholar 

  24. Curiel JA, Morales P, Gonzalez R, Tronchoni J (2017) Different non-saccharomyces yeast species stimulate nutrient consumption in S. cerevisiae mixed cultures. Front Microbiol 8:1–9

    Article  Google Scholar 

  25. González B, Vázquez J, Morcillo-Parra M et al (2018) The production of aromatic alcohols in non-Saccharomyces wine yeast is modulated by nutrient availability. Food Microbiol 74:64–74

    Article  CAS  PubMed  Google Scholar 

  26. Borrull A, López-Martínez G, Poblet M et al (2015) New insights into the toxicity mechanism of octanoic and decanoic acids on Saccharomyces cerevisiae. Yeast 32:451–460

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

This work was supported by the Ministry of Economy, Industry and Competitiveness, Spain (Grant no AGL2016-77505-C3).

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Correspondence to José Manuel Guillamón.

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Fernandez-Cruz, E., González, B., Muñiz-Calvo, S. et al. Intracellular biosynthesis of melatonin and other indolic compounds in Saccharomyces and non-Saccharomyces wine yeasts. Eur Food Res Technol 245, 1553–1560 (2019). https://doi.org/10.1007/s00217-019-03257-5

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  1. Edwin Fernandez-Cruz
  2. Sara Muñiz-Calvo
  3. Ricardo Bisquert
  4. José Manuel Guillamón