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3. Tricholides A and B and Unnarmicin D: New Hybrid PKS-NRPS Macrocycles Isolated from an Environmental Collection of Trichodesmium thiebautii.

Author

Bertin, Matthew J., Roduit, Alexandre F., Jiadong Sun, Alves, Gabriella E., Via, Christopher W., Gonzalez, Miguel A., Zimba, Paul V., and Moeller, Peter D. R.

Abstract

Bioassay-guided isolation of the lipophilic extract of Trichodesmium thiebautii bloom material led to the purification and structure characterization of two new hybrid polyketide-non-ribosomal peptide (PKS-NRPS) macrocyclic compounds, tricholides A and B (1 and 2). A third macrocyclic compound, unnarmicin D (3), was identified as a new depsipeptide in the unnarmicin family, given its structural similarity to the existing compounds in this group. The planar structures of 1-3 were determined using 1D and 2D NMR spectra and complementary spectroscopic and spectrometric procedures. The absolute configurations of the amino acid components of 1-3 were determined via acid hydrolysis, derivitization with Marfey's reagent and HPLC-UV comparison to authentic amino acid standards. The absolute configuration of the 3-hydroxydodecanoic acid moiety in 3 was determined using a modified Mosher's esterification procedure on a linear derivative of tricharmicin (4) and additionally by a comparison of 13C NMR shifts of 3 to known depsipeptides with β-hydroxy acid subunits. Tricholide B (2) showed moderate cytotoxicity to Neuro-2A murine neuroblastoma cells (EC50: 14.5 ± 6.2 μM). [ABSTRACT FROM AUTHOR]

Published
2017
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4. Isolation of Isotrichophycin C and Trichophycins G-I from a Collection of Trichodesmium thiebautii

Author

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 G−I (1−4). 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

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