A unique macrolactam derivative via a [4+6]-cycloaddition from Streptomyces niveus

Bioorg Med Chem Lett. 2016 Mar 15;26(6):1599-1604. doi: 10.1016/j.bmcl.2016.02.002. Epub 2016 Feb 2.

Abstract

One new macrolactam derivative, nivelactam (1) and one new polyenoic acid derivative, niveamide (2), along with two other known 20-atom macrolactams (3 and 4) were isolated from the fermentation broth of Streptomyces niveus, which obtained from the forest soil in northeastern China. The structures of 1 and 2 were elucidated on the basis of HRESIMS, IR, and NMR spectroscopic data analyses. Compound 1 was proposed as an intramolecular [4+6]-cycloaddition product of 3 by S. niveus, and displayed moderate cytotoxic activity against a panel of human tumor cell lines in vitro, with IC50 values ranging from 3.76 ± 0.58 to 15.02 ± 2.81 μM.

Keywords: Cycloaddition; Cytotoxicity; In vitro; Macrolactam; Streptomyces niveus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cycloaddition Reaction*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Lactams, Macrocyclic / chemistry*
  • Lactams, Macrocyclic / isolation & purification*
  • Lactams, Macrocyclic / metabolism
  • Lactams, Macrocyclic / pharmacology
  • Molecular Structure
  • Streptomyces / chemistry*
  • Streptomyces / metabolism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Lactams, Macrocyclic