Cited by 60Circadian rhythm and melatoninPhytochemicals and Antioxidant ActivitiesFree Radicals and Antioxidants

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Phenolic Melatonin-Related Compounds: Their Role as Chemical Protectors against Oxidative Stress

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Galano, Annia, Castañeda-Arriaga, Romina, Pérez-González, Adriana, Tan, Dun-Xian, Reiter, Russel·2016·Molecules

DOI 10.3390/molecules21111442PMC PMC6274579

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Abstract

There is currently no doubt about the serious threat that oxidative stress (OS) poses to human health. Therefore, a crucial strategy to maintain a good health status is to identify molecules capable of offering protection against OS through chemical routes. Based on the known efficiency of the phenolic and melatonin (MLT) families of compounds as antioxidants, it is logical to assume that phenolic MLT-related compounds should be (at least) equally efficient. Unfortunately, they have been less investigated than phenols, MLT and its non-phenolic metabolites in this context. The evidence reviewed here strongly suggests that MLT phenolic derivatives can act as both primary and secondary antioxidants, exerting their protection through diverse chemical routes. They all seem to be better free radical scavengers than MLT and Trolox, while some of them also surpass ascorbic acid and resveratrol. However, there are still many aspects that deserve further investigations for this kind of compounds.

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Figure 1 Structure of melatonin (MLT).CC BY · PubMed Central

Figure 2 Phenolic melatonin-related compounds analyzed in this review.CC BY · PubMed Central

Figure 3 Schematic representation of the metabolic route connecting the naturally occurring phenolic melatonin-related compounds. Enzymes include cytochrome P450 (CP450), horseradish peroxidase (HRP), indoleamine 2,3-dioxygenase (IDO), eosinophil peroxidase (EPO), myeloperoxidase (MPO) and melatonin 2-hydroxylase (M2H). Oxidants include ROS and RNS.CC BY · PubMed Central

Figure 4 Relative rate constants (k) for the reactions with HOO• (a) in lipid solution; (b) in aqueous solution, at pH = 7.4. The x-axis values correspond to log(ki/kTrolox). Data on Trolox, ascorbic acid, resveratrol, caffeine, propyl gallate, and caffeic acid was taken from references [120,173,263,272,292,456].CC BY · PubMed Central

Figure 5 MLT, and related compounds, grouped according to their main AOC. A question mark next to the acronym of a compound means that further investigations are needed to confirm the proposed classification, thus its position can eventually change. AFMK = N1-acetyl-N2-formyl-5-methoxykynuramine, c3-OHM = cyclic 3-hydroxymelatonin.CC BY · PubMed Central

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Authors: Galano, A., Castañeda-Arriaga, R., Pérez-González, A., Tan, D.-X., & Reiter, R.
Affiliations: Universidad Autónoma Metropolitana (MX)
Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa, 09340 Mexico City, Mexico
Consejo Nacional de Ciencia y Tecnología (CONACYT)—Departamento de Química, División de Ciencias Básicas e Ingeniería, Universidad Autónoma Metropolitana-Iztapalapa, Av. San Rafael Atlixco No. 186, Col. Vicentina, Iztapalapa, 09340 Mexico City, Mexico
The University of Texas at San Antonio Health Science Center (US)
Corresponding author: Galano, Annia
ORCID: Galano, Annia
Pérez-González, Adriana
Reiter, Russel
Venue: Molecules
Publisher: MDPI AG
Published: 2016-10-29
Volume: 21
Issue: 11
Pages: 1442
ISSN: 1420-3049 (ISSN-L)
DOI: 10.3390/molecules21111442
PMC: PMC6274579
OpenAlex: W2543661053
Cited by: 60
References: 464
Citations by year: 2026: 4 · 2025: 7 · 2024: 6 · 2023: 4 · 2022: 7 · 2021: 6 · 2020: 7 · 2019: 7 · 2018: 8 · 2017: 4
FWCI: 0.66
Type: journal article
Language: en
Open access: gold
doi.org
Licence: cc-by
creativecommons.org/licenses/by/4.0/ (vor)
Locations: Molecules (publishedVersion, cc-by)
Europe PMC (PubMed Central) (publishedVersion, cc-by)
PubMed Central (publishedVersion, cc-by)
PubMed (publishedVersion)
DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
Funders: Consejo Nacional de Ciencia y Tecnología (2015-2025)
Universidad Autónoma Metropolitana unidad Iztapalapa
Topics: Life Sciences › Neuroscience › Endocrine and Autonomic Systems › Circadian rhythm and melatonin
Health Sciences › Medicine › Biochemistry (medical) › Phytochemicals and Antioxidant Activities
Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
Keywords: melatonin, oxidative stress, antioxidants, free radical scavenging, chemical protection, vitamin C, resveratrol, Trolox, melatonin metabolites
MeSH terms: Animals, Antioxidants, Chromans, Humans, Melatonin, Phenols, Free Radical Scavengers, Oxidative Stress

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