Tricholides A and B and unnarmicin D: New hybrid PKS-NRPS macrocycles isolated from an environmental collection of Trichodesmium thiebautii

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dc.contributor.authorBertin, Matthew J.
dc.contributor.authorRoduit, Alexandre F.
dc.contributor.authorSun, Jiadong
dc.contributor.authorAlves, Gabriella E.
dc.contributor.authorVia, Christopher W.
dc.contributor.authorGonzalez, Miguel A.
dc.contributor.authorZimba, Paul V.
dc.contributor.authorMoeller, Peter D. R.
dc.date.accessioned2021-10-27T21:59:53Z
dc.date.available2021-10-27T21:59:53Z
dc.date.issued6/30/2017
dc.description.abstractBioassay-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)en_US
dc.identifier.citationBertin, M.J., Roduit, A.F., Sun, J., Alves, G.E., Via, C.W., Gonzalez, M.A., Zimba, P.V. and Moeller, P.D., 2017. Tricholides A and B and unnarmicin D: new hybrid PKS-NRPS macrocycles isolated from an environmental collection of Trichodesmium thiebautii. Marine drugs, 15(7), p.206.en_US
dc.identifier.doihttps://doi.org/10.3390/md15070206
dc.identifier.urihttps://hdl.handle.net/1969.6/89884
dc.language.isoen_USen_US
dc.publisherMDPIen_US
dc.rightsAttribution 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjecttrichodesmium thiebautiien_US
dc.subjectmacrocycleen_US
dc.subjectdepsipeptideen_US
dc.subjectcyanobacteriaen_US
dc.titleTricholides A and B and unnarmicin D: New hybrid PKS-NRPS macrocycles isolated from an environmental collection of Trichodesmium thiebautiien_US
dc.typeArticleen_US

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