Laingolide, a novel 15-membered macrolide from Lyngbya bouillonii (cyanophyceae)

Klein, D.; Braekman, Jean Claude; Daloze, Désiré; Hoffmann, Lucien; Demoulin, V.

doi:10.1016/0040-4039(96)01728-5

Cited by 67 publications

(43 citation statements)

References 2 publications

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“…These units could be initiated by the incorporation of a propionyl unit and after two acetate extensions, a glycine and two additional acetate units are condensed into the linear chain with methionine incorporation [16]. It is interesting to note that the enamide functionality in bouillonamide ( 1 ) is present in two other L. bouillonii compounds, laingolide and laingolide A, as well as in the scytophycins, a class of potent cytotoxic cyanobacterial metabolites [7,17,18]. …”

Section: Resultsmentioning

confidence: 99%

Bouillonamide: A Mixed Polyketide–Peptide Cytotoxin from the Marine Cyanobacterium Moorea bouillonii

2013

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The tropical marine cyanobacterium, Moorea bouillonii, has gained recent attention as a rich source of bioactive natural products. Continued chemical investigation of this cyanobacterium, collected from New Britain, Papua New Guinea, yielded a novel cytotoxic cyclic depsipeptide, bouillonamide (1), along with previously reported molecules, ulongamide A and apratoxin A. Planar structure of bouillonamide was established by extensive 1D and 2D NMR experiments, including multi-edited HSQC, TOCSY, HBMC, and ROESY experiments. In addition to the presence of α-amino acid residues, compound 1 contained two unique polyketide-derived moieties, namely a 2-methyl-6-methylamino-hex-5-enoic acid (Mmaha) residue and a unit of 3-methyl-5-hydroxy-heptanoic acid (Mhha). Absolute stereochemistry of the α-amino acid units in bouillonamide was determined mainly by Marfey’s analysis. Compound 1 exhibited mild toxicity with IC50’s of 6.0 µM against the neuron 2a mouse neuroblastoma cells.

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Section: Resultsmentioning

confidence: 99%

Bouillonamide: A Mixed Polyketide–Peptide Cytotoxin from the Marine Cyanobacterium Moorea bouillonii

2013

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“…In the apratoxins, these domains include highly methylated amino acids joined by proline ester and thiazoline moieties to the novel ketide 3,7-dihydroxy-2,5,8,8-tetramethylnonanoic acid. Similar ketide motifs (e.g., 7-dihydroxy-2,5,8,8-tetramethylnonanoic acid) have been encountered in isolates of the cyanobacterium Lyngbya bouillonii (10,11).…”

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confidence: 95%

Total synthesis of the marine cyanobacterial cyclodepsipeptide apratoxin A

Chen

Forsyth

2004

Proc. Natl. Acad. Sci. U.S.A.

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“…Examples include laingolide, laingolides A and B, madangolide and palmyrolide A, all of which have 15-membered macrolide rings containing a rare N -methyl enamide functionality. 5–8 These metabolites were all obtained from marine cyanobacteria belonging to the order Oscillatoriales.…”

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confidence: 99%

Sanctolide A, a 14-membered PK–NRP hybrid macrolide from the cultured cyanobacterium Oscillatoria sancta (SAG 74.79)

Kang¹,

Krunić²,

Orjala³

2012

Tetrahedron Letters

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Sanctolide A (1), a 14-membered polyketide-nonribosomal peptide (PK-NRP) hybrid macrolide, was isolated from the cultured cyanobacterium Oscillatoria sancta (SAG 74.79). The planar structure was determined using various spectroscopic techniques including HRESIMS, and 1D and 2D NMR analyses. The relative configuration was assigned by J-based configurational analysis in combination with NOE correlations. The absolute configuration was determined by Mosher ester and enantioselective HPLC analyses. The structure of sanctolide A (1) features a rare N-methyl enamide and a 2-hydroxyisovaleric acid, which are incorporated to form a 14-membered macrolide ring structure, comprising a new type of cyanobacterial macrolides derived from a PKS-NRPS hybrid biosynthetic pathway.

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Laingolide, a novel 15-membered macrolide from Lyngbya bouillonii (cyanophyceae)

Cited by 67 publications

References 2 publications

Bouillonamide: A Mixed Polyketide–Peptide Cytotoxin from the Marine Cyanobacterium Moorea bouillonii

Bouillonamide: A Mixed Polyketide–Peptide Cytotoxin from the Marine Cyanobacterium Moorea bouillonii

Total synthesis of the marine cyanobacterial cyclodepsipeptide apratoxin A

Sanctolide A, a 14-membered PK–NRP hybrid macrolide from the cultured cyanobacterium Oscillatoria sancta (SAG 74.79)

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