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

Marine Drugs

Paul V. Zimba¹  Jiadong Sun²  Miguel A. Gonzalez²  Christopher W. Via²  Matthew J. Bertin²  Alexandre F. Roduit²  Gabriella E. Alves²  Peter D. R. Moeller³ 

[1] Center for Coastal Studies and Department of Life Sciences, Texas A&Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA;M Corpus Christi, 6300 Ocean Drive, Corpus Christi, TX 78412, USA;

关键词: Trichodesmium thiebautii;    macrocycle;    depsipeptide;    cyanobacteria;   

DOI  :  10.3390/md15070206

来源: DOAJ

【 摘 要 】

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).

【 授权许可】

Unknown