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

Bertin, Matthew; Roduit, Alexandre; Sun, Jiadong; Alves, Gabriella; Via, Christopher; Gonzalez, Miguel; Zimba, Paul; Moeller, Peter

doi:10.3390/md15070206

i

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

2017
By Bertin, Matthew ; Roduit, Alexandre ; Sun, Jiadong ; ...

Details

Journal Title:

Marine Drugs
Personal Author:

Bertin, Matthew ; Roduit, Alexandre ; Sun, Jiadong ; Alves, Gabriella ; Via, Christopher ; Gonzalez, Miguel ; Zimba, Paul ; Moeller, Peter
NOAA Program & Office:

NOS (National Ocean Service) ; NCCOS (National Centers for Coastal Ocean Science)
Description:

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 C-13 NMR shifts of 3 to known depsipeptides with beta-hydroxy acid subunits. Tricholide B (2) showed moderate cytotoxicity to Neuro-2A murine neuroblastoma cells (EC50: 14.5 +/- 6.2 mu M).
Source:

Marine Drugs, 15(7), 11.
DOI:

https://doi.org/10.3390/md15070206
Document Type:

Journal Article
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CC BY
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Submitted
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urn:sha256:b83c88d014e6eb6339a4755470f8dd790cb975dc5387fdff4c8cbff30843a2ef
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https://repository.library.noaa.gov/view/noaa/20577/noaa_20577_DS1.pdf
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[PDF - 828.22 KB ]

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