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Mycosporine-Like Amino Acids and Their Derivatives as Natural Antioxidants

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Wada, Naoki, Sakamoto, Toshio, Matsugo, Seiichi·2015·Antioxidants

DOI 10.3390/antiox4030603PMC PMC4665425

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Abstract

Mycosporine-like amino acids (MAAs) are water-soluble molecules that absorb UV-A and UV-B radiation and disperse the energy as heat. MAAs show great diversity in their molecular structures, which exhibit a range of molecular weights spanning 188 to 1050 Daltons. MAAs are utilized in a wide variety of organisms including prokaryotes and eukaryotic micro-organisms that inhabit aquatic, terrestrial, and marine environments. These features suggest that MAAs are stable and fundamental molecules that allow these organisms to live under UV irradiation. MAAs are thought to have been greatly important to ancient forms of life on Earth, functioning as a primary sunscreen to reduce short-wavelength light. Structurally different MAAs might have been developed in MAA-producing organisms during their environmental adaptation. Harmful irradiation directly damages biomolecules, including lipids, proteins and DNA, and induces oxidative stress through radical-propagating processes. Thus, MAAs are expected to play an additional role in the antioxidant system. This review focuses on MAAs with radical scavenging activities. To cover all the reported MAAs known thus far, we surveyed the CAS database and have summarized the structures and the chemical and physical properties of these MAAs, including their antioxidant activities.

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Figure 1 Structural relationships of various mycosporine-like amino acids (MAAs). Note that ammonia is not used for MAA biosynthesis due to its toxicity; however, it is useful to simplify the figure by explaining the structural relationships of various types of MAAs.CC BY · PubMed Central

Figure 2 Chemical structure and spectroscopic properties of MAA precursors. Abbreviation is in parenthesis.CC BY · PubMed Central

Figure 3 Chemical structure and spectroscopic properties of aminocyclohexenone-type MAAs. Abbreviations are shown in parenthesis.CC BY · PubMed Central

Figure 4 Chemical structure and spectroscopic properties of aminocyclohexene imine-type MAAs. Abbreviation is in parenthesis.CC BY · PubMed Central

Scheme 1 Plausible hypothesis for the biosynthetic pathway of Euhalothece-362.CC BY · PubMed Central

Figure 5 Chemical structures and spectroscopic properties of derivatized MAAs. Abbreviations are in parenthesis.CC BY · PubMed Central

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Authors: Wada, N., Sakamoto, T., & Matsugo, S.
Affiliations: Kanazawa University (JP)
Corresponding author: Matsugo, Seiichi
ORCID: Wada, Naoki
Sakamoto, Toshio
Venue: Antioxidants
Publisher: MDPI AG
Published: 2015-09-07
Volume: 4
Issue: 3
Pages: 603-646
ISSN: 2076-3921 (ISSN-L)
DOI: 10.3390/antiox4030603
PMC: PMC4665425
OpenAlex: W1667784456
Cited by: 283
References: 126
Citations by year: 2026: 25 · 2025: 36 · 2024: 25 · 2023: 34 · 2022: 29 · 2021: 29 · 2020: 34 · 2019: 30 · 2018: 18 · 2017: 17 · 2016: 6
FWCI: 2.18
Type: journal article
Language: en
Open access: gold
dx.doi.org
Licence: cc-by
creativecommons.org/licenses/by/4.0/ (vor)
Locations: Antioxidants (publishedVersion, cc-by)
PubMed Central (publishedVersion, cc-by)
PubMed (publishedVersion)
DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
Topics: Health Sciences › Medicine › Dermatology › Skin Protection and Aging
Life Sciences › Immunology and Microbiology › Applied Microbiology and Biotechnology › Microbial Natural Products and Biosynthesis
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Microbial Metabolism and Applications
Keywords: mycosporine-like amino acids, natural antioxidants, free radical scavenging, UV protection, oxidative stress, UV-absorbing compounds

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Mycosporine-Like Amino Acids and Their Derivatives as Natural Antioxidants

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