1. Isolation of Isotrichophycin C and Trichophycins G-I from a Collection of Trichodesmium thiebautii
- Author
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Roberta Teta, Riley D. Kirk, Kelly M McManus, Alfonso Mangoni, Matthew J. Bertin, Christopher W. Via, Silvia Scarpato, Alexandre F Roduit, James S Lotti, Mcmanus, K. M., Kirk, R. D., Via, C. W., Lotti, J. S., Roduit, A. F., Teta, R., Scarpato, S., Mangoni, A., and Bertin, M. J.
- Subjects
Metabolite ,Pharmaceutical Science ,Antineoplastic Agents ,Cyanobacteria ,Article ,Mass Spectrometry ,Analytical Chemistry ,Murine neuroblastoma ,chemistry.chemical_compound ,Mice ,Tandem Mass Spectrometry ,Cell Line, Tumor ,Drug Discovery ,Metabolome ,Animals ,Trichodesmium thiebautii ,Phylogeny ,Pharmacology ,biology ,Molecular Structure ,Chemistry ,Organic Chemistry ,Absolute configuration ,DNA ,biology.organism_classification ,Isolation (microbiology) ,Trichodesmium ,Complementary and alternative medicine ,Biochemistry ,Molecular networking ,Molecular Medicine ,Chlorine - Abstract
The trichophycin family of compounds are chlorinated polyketides first discovered from environmental collections of a bloom-forming Trichodesmium sp. cyanobacterium. In an effort to fully capture the chemical space of this group of metabolites, the utilization of MS/MS-based molecular networking of a Trichodesmium thiebautii extract revealed a metabolome replete with halogenated compounds. Subsequent MS-guided isolation resulted in the characterization of isotrichophycin C and trichophycins GāI (1ā4). These new metabolites had intriguing structural variations from those trichophycins previously characterized, which allowed for a comparative study to examine structural features that are associated with toxicity to murine neuroblastoma cells. Additionally, we propose the absolute configuration of the previously characterized trichophycin A (5). Overall, the metabolome of the Trichodesmium bloom is hallmarked by an unprecedented amount of chlorinated molecules, many of which remain to be structurally characterized.
- Published
- 2020