CoChat
Sign Up
Cited by 60Circadian rhythm and melatoninPhytochemicals and Antioxidant ActivitiesFree Radicals and Antioxidants

The DOI matches its Crossref record; 456 of the 464 references it cites were found in a registry or an index, and 1 are not checked yet.

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

Open access
Galano, Annia, Castañeda-Arriaga, Romina, Pérez-González, Adriana, Tan, Dun-Xian, Reiter, Russel·2016·Molecules
DOI 10.3390/molecules21111442PMC PMC6274579
Open this paper in CoChat — free accountOpen PDF

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.

Overview

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.3390/molecules21111442

Cites

456 of 457 references verified0 citation errors · 0 not checkable

Statistics

Figures

Figure 1 Structure of melatonin (MLT).
Figure 1 Structure of melatonin (MLT).CC BY · PubMed Central
Figure 2 Phenolic melatonin-related compounds analyzed in this review.
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.
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].
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.
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

Verification

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Citations

Cites

3 retracted

Research works printed but not linked: 5

  1. Daulatzai, 2016, Fundamental role of pan-inflammation and oxidative-nitrosative pathways in neuropathogenesis of Alzheimer’s disease, Am. J. Neurodegener. Dis., 5, 1
  2. Wang, 2014, Electron paramagnetic resonance spin-trapping study of free radicals in gas phase of mainstream cigarette smoke using two spin traps, Tobacco Sci. Technol., 47, 47
  3. Poeggeler, 1995, Melatonin, a mediator of electron transfer and repair reactions, acts synergistically with the chain-breaking antioxidants ascorbate, trolox and glutathione, Neuroendocrinol. Lett., 17, 87
  4. Saxena, 2012, Flavonoids and phenolic acids as antioxidants in plants and human health, Int. J. Pharm. Sci. Rev. Res., 16, 130
  5. Chaudhari, 2015, Comparative antioxidant activity of twenty traditional Indian medicinal plants and its correlation with total flavonoid and phenolic content, Int. J. Pharm. Sci. Rev. Res., 30, 105

Cited by

Sorted by citations

See all 60

Related

See all

Metadata

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
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
Licence
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

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review