Isolation and Structure Elucidation of Cytotoxic Saccharothriolides D to F from a Rare Actinomycete Saccharothrix sp. and Their Structure-Activity Relationship

J Nat Prod. 2016 Jul 22;79(7):1891-5. doi: 10.1021/acs.jnatprod.6b00372. Epub 2016 Jun 22.

Abstract

Three new 10-membered macrolides, saccharothriolides D-F (1-3), were isolated from a rare actinomycete, Saccharothrix sp. A1506. The planar structures were determined from analysis of extensive NMR and HR-ESI-MS data, and the absolute configurations were established by ECD spectroscopy analysis. Saccharothriolides D (1) and E (2) were determined to be C-2 epimers of saccharothriolides A (4) and B (5), respectively. Saccharothriolide F (3) was identified to be a demethylated congener of saccharothriolides D (1) and A (4) at the C-2 position. The availability of compounds 1-6 enabled a structure-activity relationship study that revealed the importance of the phenolic hydroxy group at C-2″ and the stereochemistry of C-2 for the inhibition of human fibrosarcoma HT1080 cell growth.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinomycetales / chemistry*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Macrolides
  • saccharothriolide D
  • saccharothriolide E
  • saccharothriolide F