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Mar. Drugs 2017, 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

1
Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA
2
Center for Coastal Studies and Department of Life Sciences, Texas A&M Corpus Christi, 6300 Ocean Drive, Corpus Christi, TX 78412, USA
3
Emerging Toxins Program, National Ocean Service/NOAA, Hollings Marine Laboratory, 331 Fort Johnson Road, Charleston, SC 29412, USA
*
Author to whom correspondence should be addressed.
Received: 10 May 2017 / Revised: 10 June 2017 / Accepted: 27 June 2017 / Published: 30 June 2017
(This article belongs to the Special Issue Compounds from Cyanobacteria II, 2017)
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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 13 were determined using 1D and 2D NMR spectra and complementary spectroscopic and spectrometric procedures. The absolute configurations of the amino acid components of 13 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). View Full-Text
Keywords: Trichodesmium thiebautii; macrocycle; depsipeptide; cyanobacteria Trichodesmium thiebautii; macrocycle; depsipeptide; cyanobacteria
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Bertin, M.J.; Roduit, A.F.; Sun, J.; Alves, G.E.; Via, C.W.; Gonzalez, M.A.; Zimba, P.V.; Moeller, P.D.R. Tricholides A and B and Unnarmicin D: New Hybrid PKS-NRPS Macrocycles Isolated from an Environmental Collection of Trichodesmium thiebautii. Mar. Drugs 2017, 15, 206.

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