Total Structure Determination of Apratoxin A, a Potent Novel Cytotoxin from the Marine Cyanobacterium Lyngbya majuscula
Abstract
Apratoxin A (1), a potent cytotoxin with a novel skeleton, has been isolated from the marine cyanobacterium Lyngbya majuscula Harvey ex Gomont. This cyclodepsipeptide of mixed peptide-polyketide biogenesis bears a thiazoline ring flanked by polyketide portions, one of which possesses an unusual methylation pattern. Its gross structure has been elucidated by spectral analysis, including various 2D NMR techniques. The absolute configurations of the amino acid-derived units were determined by chiral HPLC analysis of hydrolysis products. The relative stereochemistry of the new dihydroxylated fatty acid unit, 3,7-dihydroxy-2,5,8,8-tetramethylnonanoic acid, was elucidated by successful application of the J-based configuration analysis originally developed for acyclic organic compounds using carbon-proton spin-coupling constants ((2,3)J(C,H)) and proton-proton spin-coupling constants ((3)J(H,H)); its absolute stereochemistry was established by Mosher analysis. The conformation of 1 in solution was mimicked by molecular modeling, employing a combination of distance geometry and restrained molecular dynamics. Apratoxin A (1) possesses IC(50) values for in vitro cytotoxicity against human tumor cell lines ranging from 0.36 to 0.52 nM; however, it was only marginally active in vivo against a colon tumor and ineffective against a mammary tumor.
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Cyanobacteria are a rich source of highly bioactive natural products, and in particular, protease inhibitors from numerous chemical classes.
“Cyanobacteria are known to be a rich source of highly bioactive natural products32–35, and in particular, protease inhibitors from numerous chemical classes36–41.”
From Native metabolomics identifies the rivulariapeptolide family of protease inhibitors (2022) · cites this paper as [35]
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- Authors
- Luesch, H., Yoshida, W. Y., Moore, R. E., Paul, V. J., & Corbett, T. H.
- Affiliations
- University of Hawaiʻi at Mānoa (US)
- Corresponding author
- Moore, Richard E.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-05-15
- Volume
- 123
- Issue
- 23
- Pages
- 5418-5423
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1971910884
- Cited by
- 373
- References
- 24
- Citations by year
- 2026: 9 · 2025: 12 · 2024: 15 · 2023: 22 · 2022: 22 · 2021: 21 · 2020: 16 · 2019: 15 · 2018: 26 · 2017: 19 · 2016: 14 · 2015: 22 · 2014: 17 · 2013: 24 · 2012: 12
- FWCI
- 6.68
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Cancer Institute (CA-53001)
- National Institute of General Medical Sciences (GM 44796, S06GM044796)
- Topics
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Physical Sciences › Chemistry › Spectroscopy › Molecular spectroscopy and chirality
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
- Keywords
- Lyngbya majuscula, marine cyanobacteria, cytotoxin, cyclodepsipeptides, absolute configuration, relative configuration, molecular modeling, cytotoxicity, cancer cell lines
- MeSH terms
- Adenocarcinoma, Cyanobacteria, Animals, Bacterial Toxins, Breast Neoplasms, Cell Survival, Colonic Neoplasms, Cytotoxins, Female, Humans, Male, Marine Toxins, Peptides, Cyclic, Tumor Cells, Cultured, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Inhibitory Concentration 50, Depsipeptides, Mice
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