6-Deoxy-13-hydroxy-8,11-dione-dihydrogranaticin B, an intermediate in granaticin biosynthesis, from Streptomyces sp. CPCC 200532

J Nat Prod. 2014 Sep 26;77(9):2130-3. doi: 10.1021/np500138k. Epub 2014 Aug 25.

Abstract

A new granaticin analogue and its hydrolysis product were isolated from Streptomyces sp. CPCC 200532. Their structures were determined to be 6-deoxy-13-hydroxy-8,11-dione-dihydrogranaticins B (1) and A (2), respectively, by detailed analysis of spectroscopic data. Compound 1 was regarded as an intermediate in granaticin biosynthesis, as it was bioconvertable to granaticin B. Compared to granaticin B, 1 showed similar cytotoxicity against cancer cell line HCT116, but decreased cytotoxicity against cancer cell lines A549, HeLa, and HepG2. Compound 2 displayed lower cytotoxicity than 1 against all four cancer cell lines tested.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Drug Screening Assays, Antitumor
  • HCT116 Cells
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Naphthoquinones / chemistry
  • Naphthoquinones / isolation & purification
  • Naphthoquinones / pharmacology
  • Streptomyces / chemistry*

Substances

  • 6-deoxy-13-hydroxy-8,11-dione-dihydrogranaticins B
  • Antineoplastic Agents
  • Naphthoquinones
  • dihydrogranaticin
  • granaticin