Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly
Abstract
Hectochlorin (1) was isolated from marine isolates of Lyngbya majuscula collected from Hector Bay, Jamaica, and Boca del Drago Beach, Bocas del Toro, Panama. The planar structure was deduced by one- and two-dimensional NMR spectroscopy. X-ray crystallography was used to determine the absolute stereochemistry of hectochlorin as 2S,3S,14S,22S. Hectochlorin is equipotent to jasplakinolide (5) in its ability to promote actin polymerization, but unlike jasplakinolide, is unable to displace a fluorescent phalloidin analogue from polymerized actin. In addition, hectochlorin shows both a unique profile of cytotoxicity by the COMPARE algorithm and potent inhibitory activity toward the fungus Candida albicans. Structurally, hectochlorin resembles dolabellin and the recently reported lyngbyabellin class of compounds.
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Lyngbyabellin B exerts cytotoxic effects via cell cycle inhibition.
“A similar mechanistic effect was reported for the cyclic depsipeptide coibamide A, isolated from Leptolyngbya sp. [100], and lyngbyabellin B, isolated from Lyngbya majuscule [182].”
From Marine Natural Products: A Source of Novel Anticancer Drugs (2019) · cites this paper as [182]
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Marine Natural Products: A Source of Novel Anticancer Drugs
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- Authors
- Marquez, B. L., Watts, K. S., Yokochi, A., Roberts, M. A., Verdier-Pinard, P., Jimenez, J. I., Hamel, E., Scheuer, P. J., & Gerwick, W. H.
- Affiliations
- College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, Department of Biochemistry and Biophysics, Oregon State University, Corvallis, Oregon 97331, Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, Screening Technologies Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute at Frederick, National Institutes of Health, Frederick, Maryland 21702, and Chemistry Department, University of Hawaii at Monoa,...
- University of Hawaiʻi at Mānoa (US)
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-06-01
- Volume
- 65
- Issue
- 6
- Pages
- 866-871
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- OpenAlex
- W1978850646
- Cited by
- 181
- References
- 15
- Citations by year
- 2026: 6 · 2025: 4 · 2024: 8 · 2023: 7 · 2022: 16 · 2021: 15 · 2020: 12 · 2019: 11 · 2018: 8 · 2017: 11 · 2016: 6 · 2015: 6 · 2014: 6 · 2013: 8 · 2012: 8
- FWCI
- 2.87
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Natural Products (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institutes of Health
- National Cancer Institute (CA52955)
- National Institute of Environmental Health Sciences (P30-ES03850, P30ES003850)
- Topics
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Marine Sponges and Natural Products
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive Natural Diterpenoids Research
- Keywords
- Lyngbya majuscula, actin polymerization, absolute configuration, jasplakinolide, cytotoxicity, structure elucidation
- MeSH terms
- Actins, Cyanobacteria, Anti-Bacterial Agents, Antifungal Agents, Candida albicans, Jamaica, Lactones, Lyngbya Toxins, Molecular Conformation, Panama, Peptides, Cyclic, Thiazoles, Molecular Structure, Fluorescein-5-isothiocyanate, Crystallography, X-Ray, Nuclear Magnetic Resonance, Biomolecular, Inhibitory Concentration 50, Depsipeptides
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