Sanctolide A, a 14-membered PK-NRP hybrid macrolide from the cultured cyanobacterium Oscillatoria sancta (SAG 74.79) |
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Authors: | Kang Hahk-Soo Krunic Aleksej Orjala Jimmy |
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Institution: | Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, 833 South Wood Street, University of Illinois at Chicago, Chicago, IL 60612, USA |
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Abstract: | 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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Keywords: | Cyanobacteria Oscillatoria sancta 14-Membered macrolide PK-NRP hybrid Brine shrimp toxicity |
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