Isolation of Nocuolin A and Synthesis of New Oxadiazine Derivatives. Design, Synthesis, Molecular Docking, Apoptotic Evaluation, and Cathepsin B Inhibition.

Nocuolin A (1), an oxadiazine, was isolated from the cyanobacterium Nostoc sp. Its chemical structure was elucidated using NMR and mass spectroscopic data. From this compound, two new oxadiazines, 3-[(6R)-5,6-dihydro-4,6-dipentyl-2H-1,2,3-oxadiazin-2-yl]-3-oxopropyl acetate (2) and 4-{3-[(6R)-5,6-dihydro-4,6-dipentyl-2H-1,2,3-oxadiazin-2-yl]-3-oxopropoxy}-4-oxobutanoic acid (3), were synthesised. The chemical structures of these two compounds were elucidated by a combination of NMR and MS analysis. Compound 3 showed cytotoxicity against the ACHN (0.73 ± 0.10 µM) and Hepa-1c1c7 (0.91 ± 0.08 µM) tumour cell lines. Similarly, compound 3 significantly decreased cathepsin B activity in ACHN and Hepa-1c1c7 tumour cell lines at concentrations of 1.52 ± 0.13 nM and 1.76 ± 0.24 nM, respectively. In addition, compound 3 showed no in vivo toxicity in a murine model treated with a dose of 4 mg/kg body weight.

Anti-inflammatory activity of glycolipids isolated from cyanobacterium Nodularia harveyana.

Activity-guided fractionations from the freshwater cyanobacterium Nodularia harveyana led to the isolation of two monogalactosyldiacylglycerols (MGDG), two digalactosyldiacylglycerols (DGDG), two monoglucosyldiacylglycerols (MGlcDG) and 1-(O-hexose)-3,25-hexacosanediol (HG). Structures were elucidated by a combination of 1D and 2D NMR analysis, HRMS and GC-MS. The potential for inhibition against TNF-α and NF-κB production of these seven compounds was tested in THP-1 cells. All compounds showed activity, but compound 7 showed higher inhibitory activity of TNF-α and NF-κB, with IC50 of 4.88 ± 0.13 and 3.64 ± 0.45 µM, respectively.

Cybastacines A and B: Antibiotic Sesterterpenes from a Nostoc sp. Cyanobacterium.

Cybastacines A (1) and B (2) were discovered as a novel pentacyclic sesterterpenoid-alkaloid skeleton structure, with a guanidinium group. These molecules were isolated from a Nostoc sp. cyanobacterium collected in the Canary Islands. Their structures were elucidated primarily by a combination of spectroscopic analyses and X-ray diffraction. These compounds showed antibiotic activities against several clinically relevant bacterial strains.