Marine Natural Products as Novel Antioxidant Prototypes
Open accessAbstract
Pure natural products isolated from marine sponges, algae, and cyanobacteria were examined for antioxidant activity using a 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) solution-based chemical assay and a 2',7'-dichlorodihydrofluorescein diacetate (DCFH-DA) cellular-based assay. The DCFH system detects only antioxidants that penetrate cellular membranes. Potent antioxidants were identified and the results from each system compared. The algal metabolites cymopol (1), avrainvilleol (3), and fragilamide (4), and the invertebrate constituent puupehenone (5) showed strong antioxidant activity in both systems. Several compounds were active in the DPPH assay but significantly less active in the DCFH system. The green algal metabolite 7-hydroxycymopol (2) was isolated from Cymopolia barbataand its structure determined. Compound 2 was significantly less active in the DCFH system than cymopol (1). The sponge metabolites (1S)-(+)-curcuphenol (6), aaptamine (7), isoaaptamine (8), and curcudiol (9) and the cyanobacterial pigment scytonemin (10) showed strong antioxidant activity in the DPPH assay, but were relatively inactive in the DCFH system. Thus, cellular uptake dramatically affects the potential significance of antioxidants discovered using only the DPPH assay. The apparent "proantioxidants" hormothamnione A diacetate (11) and Laurencia monomer diacetate (12) require metabolic activation for antioxidant activity. Significant advantages are achieved using both a solution- and cellular-based assay to discover new antioxidants.
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MAA are multifunctional photoprotective compounds acting as chemical and biological anti-oxidants.
“it is clear that MAA are multifunctional photoprotective compounds acting as chemical and biological anti-oxidants.”
From Mycosporine-Like Amino Acids for Skin Photoprotection (2019) · cites this paper as [79]
MAA have antioxidant properties, demonstrated with different MAA from a large variety of species.
“This has been demonstrated with different MAA from a large variety of species [78-81].”
From Mycosporine-Like Amino Acids for Skin Photoprotection (2019) · cites this paper as [79]
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- Authors
- Takamatsu, S., Hodges, T. W., Rajbhandari, I., Gerwick, W. H., Hamann, M. T., & Nagle, D. G.
- Affiliations
- Oregon State University (US)
- Corresponding author
- Nagle, Dale G.
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-04-17
- Volume
- 66
- Issue
- 5
- Pages
- 605-608
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- PMC
- PMC4969048
- OpenAlex
- W2044128001
- Cited by
- 278
- References
- 43
- Citations by year
- 2026: 5 · 2025: 8 · 2024: 11 · 2023: 13 · 2022: 11 · 2021: 14 · 2020: 19 · 2019: 15 · 2018: 7 · 2017: 19 · 2016: 9 · 2015: 8 · 2014: 15 · 2013: 16 · 2012: 22
- FWCI
- 3.21
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Journal of Natural Products (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Cancer Institute (CA52955, U19CA052955)
- National Institute of Allergy and Infectious Diseases (R01AI036596)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Marine Sponges and Natural Products
- Life Sciences › Agricultural and Biological Sciences › Aquatic Science › Seaweed-derived Bioactive Compounds
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Keywords
- marine natural products, antioxidant activity, marine sponges, marine algae, cyanobacteria, DPPH assay, cellular uptake, aaptamine, curcuphenol, scytonemin, structure-activity relationship
- MeSH terms
- Cyanobacteria, Animals, Antioxidants, Biological Products, Biphenyl Compounds, Jamaica, Picrates, Porifera, Stereoisomerism, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Eukaryota
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