Isolation, characterization and antiproliferative activity of new metabolites from the South African endemic red algal species Laurencia alfredensis
Open accessAbstract
The marine red algae of the genus Laurencia have been widely studied for their structurally diverse and biologically active secondary metabolites. We report here the natural product investigation of the organic extract of a newly identified South African endemic species, Laurencia alfredensis. A sequence of column chromatography, preparative TLC and normal phase HPLC resulted in the isolation of eleven compounds comprising three labdane-type diterpenes (1–3), four polyether triterpenes (4–7), three cholestane-type ecdysteroids (8–10) and a glycolipid (11). Compounds 1–3, 5–8 and 10 have not previously been reported, while compound 9 is reported here for the first time from a natural source and the known compound 11 isolated for the first time from the genus Laurencia. The structural elucidation and the relative configuration assignments of the compounds were accomplished by extensive use of 1D- and 2D-NMR, HR-ESI-MS, UV and IR spectroscopic techniques, while the absolute configuration of compound 1 was determined by single-crystal X-ray diffraction analysis. All compounds were evaluated against the MDA-MB-231 breast and HeLa cervical cancer cell lines. Compound 2 exhibited low micromolar antiproliferative activity (IC50 = 9.3 µM) against the triple negative breast carcinoma and compound 7 was similarly active (IC50 = 8.8 µM) against the cervical cancer cell line.
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Three new ecdysteroids, alfredensterol (211), 3-deacetoxy alfredensterol (212), and 14α-hydroxy alfredensterol (213), were isolated from Laurencia alfredensis.
“These are alfredensterol (211), 3-deacetoxy alfredensterol (212), and 14α-hydroxy alfredensterol (213), isolated from Laurencia alfredensis (red algae)147.”
From The Phytochemical, Biological, and Medicinal Attributes of Phytoecdysteroids: An Updated Review (2021) · cites this paper as [147]
Alfredensterol, 3-deacetoxy alfredensterol, and 14α-hydroxy alfredensterol exhibited moderate antiproliferative activity against MDA-MB-231 and HeLa cell lines.
“Evaluated antiproliferative activity against MDA-MB-231 breast and HeLa human cervical cancer cell lines and exhibited moderate activity.”
From The Phytochemical, Biological, and Medicinal Attributes of Phytoecdysteroids: An Updated Review (2021) · cites this paper as [147]
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The Phytochemical, Biological, and Medicinal Attributes of Phytoecdysteroids: An Updated Review
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- Authors
- Dziwornu, G. A., Caira, M. R., Mare, J.-A. D. L., Edkins, A. L., Bolton, J. J., Beukes, D. R., & Sunassee, S. N.
- Affiliations
- University of Cape Town (ZA)
- Rhodes University (ZA)
- University of the Western Cape (ZA)
- South African Medical Research Council (ZA)
- Corresponding author
- Sunassee, Suthananda N.
- ORCID
- Venue
- Molecules
- Publisher
- MDPI AG
- Published
- 2017-03-23
- Volume
- 22
- Issue
- 4
- Pages
- 513
- ISSN
- 1420-3049 (ISSN-L)
- PMC
- PMC6154597
- OpenAlex
- W2597837741
- Cited by
- 25
- References
- 35
- Citations by year
- 2026: 2 · 2025: 2 · 2023: 2 · 2022: 4 · 2021: 2 · 2020: 4 · 2019: 4 · 2018: 3 · 2017: 2
- FWCI
- 4.10
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- Locations
- Molecules (publishedVersion, cc-by)
- Europe PMC (PubMed Central) (publishedVersion, other-oa)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Funders
- National Research Foundation (98566, 90641, 105829)
- South African Medical Research Council
- Cancer Association of South Africa
- Rhodes University
- University of Cape Town
- National Treasury
- Medical Research Council
- Topics
- Life Sciences › Agricultural and Biological Sciences › Aquatic Science › Seaweed-derived Bioactive Compounds
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive Natural Diterpenoids Research
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Marine Sponges and Natural Products
- Keywords
- Laurencia, red algae, marine natural products, labdane diterpenes, glycolipids, antiproliferative activity, triple-negative breast cancer, cervical cancer, MDA-MB-231 cells, HeLa cells, structure elucidation, absolute configuration, novel metabolites
- MeSH terms
- Drug Screening Assays, Antitumor, Glycolipids, HeLa Cells, Humans, Terpenes, Triterpenes, Molecular Structure, Crystallography, X-Ray, Ecdysteroids, Laurencia, Cell Line, Tumor, Cell Proliferation
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