Isolation and Structure Elucidation of Satosporin A and B: New Polyketides from Kitasatospora griseola

Abstract

Satosporins A and B, two novel glucosylated polyketides, were isolated from the actinomycete Kitasatospora griseola MF730-N6. The polyketides possess an unprecedented tricyclic ring system that was fully characterized using a combination of spectroscopic analyses and computational calculations. Satosporin A was quantitatively converted into its aglycon homologue, satosporin C, using a β-glucosidase. The determination of the absolute stereochemistry was achieved using solution TDDFT/ECD calculations and chemical derivatization methods.

Genus Kitasatospora, taxonomic features and diversity of secondary metabolites

“…The producing strain, compound name, activities of the compounds, reported by year, are shown in Table 3. 1,10,[26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42] Setamycin possesses antitrichomonal and antifungal activities. Phosalacine possesses herbicidal activity.…”

Natural products containing ‘decalin’ motif in microorganisms

“…167 The synthetic methods of the functional fragments of spirotetronates involving the intermolecular Diels-Alder reaction can be increasingly found in many reports. 168,169 3.11 Pyrrolizidines UCS1025-A (183) and -B (184), possessing the unprecedented furopyrrolizin-2,6-dione system, were isolated in 2000 from the broth of the fungus Acremonium sp. 170 Their structural elucidations were achieved by spectral data and X-ray crystallographic analysis, 171 indicating two more tautomeric isomers in UCS1025A.…”

Comparative Genomic Insights Into the Taxonomic Classification, Diversity, and Secondary Metabolic Potentials of Kitasatospora, a Genus Closely Related to Streptomyces

“…As the sister genus of Streptomyces , Kitasatospora has gradually attracted people’s attention ( Hao et al, 2020 ; Kim et al, 2020 ; Yun et al, 2020 ). So far, at least 50 bioactive compounds have been discovered from Kitasatospora strains ( Takahashi, 2017 ), such as setamycin, kitasetaline, and satosporin ( Ōmura et al, 1981 ; Aroonsri et al, 2012 ; Arens et al, 2013 ), exhibiting a wide range of bioactivities (e.g., antifungal, herbicidal, antitumor). Nevertheless, little is known about the potential differences in the secondary metabolism and genetics between genera.…”