New benzoxazine secondary metabolites from an arctic actinomycete

Mar Drugs. 2014 Apr 30;12(5):2526-38. doi: 10.3390/md12052526.

Abstract

Two new secondary metabolites, arcticoside (1) and C-1027 chromophore-V (2), were isolated along with C-1027 chromophore-III and fijiolides A and B (3-5) from a culture of an Arctic marine actinomycete Streptomyces strain. The chemical structures of 1 and 2 were elucidated through NMR, mass, UV, and IR spectroscopy. The hexose moieties in 1 were determined to be d-glucose from a combination of acid hydrolysis, derivatization, and gas chromatographic analyses. Arcticoside (1) and C-1027 chromophore-V (2), which have a benzoxazine ring, inhibited Candida albicans isocitrate lyase. Chromophore-V (2) exhibited significant cytotoxicity against breast carcinoma MDA-MB231 cells and colorectal carcinoma cells (line HCT-116), with IC₅₀ values of 0.9 and 2.7 μM, respectively.

MeSH terms

  • Antifungal Agents / pharmacology
  • Antineoplastic Agents / pharmacology
  • Arctic Regions
  • Benzoxazines / chemistry*
  • Benzoxazines / metabolism*
  • Benzoxazines / pharmacology
  • Candida albicans / drug effects
  • Cell Line, Tumor
  • Cell Proliferation
  • Hexoses / chemistry
  • Humans
  • Streptomyces / chemistry*

Substances

  • Antifungal Agents
  • Antineoplastic Agents
  • Benzoxazines
  • Hexoses