Cytotoxic Spliceostatin Analogs from Pseudomonas sp

Chem Biodivers. 2019 Sep;16(9):e1900266. doi: 10.1002/cbdv.201900266. Epub 2019 Aug 8.

Abstract

Two new spliceostatin analogs, designed as spliceostatins J and K (1 and 2), were isolated and identified from the culture of Pseudomonas sp., along with two known ones, FR901464 (3) and spliceostatin E (4). Their structures were elucidated by detailed interpretation of their spectroscopic data, especially 2D-NMR and HR-ESI-MS. Spliceostatin J (1) represented the first example of spliceostatins bearing an unusual hexahydrofuro[3,4-b]furan moiety. Biological assay showed all the isolated compounds except 1 displayed potent cytotoxic activities against two cancer cell lines (MDA-MB-231 and A-549). Structure-activity-relationship studies revealed that the tetrahydropyran ring in spliceostatin analogs was necessary for their bioactive retention.

Keywords: Pseudomonas; bacteria; biological activity; cytotoxicity; spliceostatin.

MeSH terms

  • A549 Cells
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Furans / chemistry
  • Furans / isolation & purification
  • Furans / pharmacology*
  • Humans
  • Lactones / chemistry
  • Lactones / isolation & purification
  • Lactones / pharmacology*
  • Molecular Structure
  • Pseudomonas / chemistry*
  • Pyrans / chemistry
  • Pyrans / isolation & purification
  • Pyrans / pharmacology
  • Pyrones / chemistry
  • Pyrones / isolation & purification
  • Pyrones / pharmacology*
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification
  • Spiro Compounds / pharmacology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • FR 901464
  • Furans
  • Lactones
  • Pyrans
  • Pyrones
  • Spiro Compounds
  • spliceostatin E