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. 2017 Jun 30;15(7):206.
doi: 10.3390/md15070206.

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

Matthew J Bertin  1 , Alexandre F Roduit  2 , Jiadong Sun  3 , Gabriella E Alves  4 , Christopher W Via  5 , Miguel A Gonzalez  6 , Paul V Zimba  7 , Peter D R Moeller  8
Affiliations

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

Matthew J Bertin et al. Mar Drugs. .

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).

Keywords: Trichodesmium thiebautii; cyanobacteria; depsipeptide; macrocycle.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of tricholide A (1), tricholide B (2) and unnarmicin D (3). The configuration of C-16 and C-17 in 1 and 2 is relative and noted by (*).
Figure 2
Figure 2
Selected 2D NMR correlations for 1 and 3.
See this image and copyright information in PMC

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