Cytotoxic Spliceostatins from Burkholderia sp. and Their Semisynthetic Analogues

J Nat Prod. 2014 Aug 22;77(8):1864-70. doi: 10.1021/np500342m.

Abstract

The spliceostatin class of natural products was reported to be potent cytotoxic agents via inhibition of the spliceosome, a key protein complex in the biosynthesis of mature mRNA. As part of an effort to discover novel leads for cancer chemotherapy, we re-examined this class of compounds from several angles, including fermentation of the producing strains, isolation and structure determination of new analogues, and semisynthetic modification. Accordingly, a group of spliceostatins were isolated from a culture broth of Burkholderia sp. FERM BP-3421, and their structures identified by analysis of spectroscopic data. Semisynthesis was performed on the major components 4 and 5 to generate ester and amide derivatives with improved in vitro potency. With their potent activity against tumor cells and unique mode of action, spliceostatins can be considered potential leads for development of cancer drugs.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Burkholderia / chemistry*
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Pyrans / chemical synthesis
  • Pyrans / chemistry
  • Pyrans / isolation & purification*
  • Pyrans / pharmacology*
  • RNA, Messenger / biosynthesis
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Spiro Compounds / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Pyrans
  • RNA, Messenger
  • Spiro Compounds
  • spliceostatin A