Octyl substituted butenolides from marine-derived Streptomyces koyangensis

Nat Prod Res. 2021 Aug;35(15):2602-2607. doi: 10.1080/14786419.2019.1686368. Epub 2019 Nov 6.

Abstract

A new butenolide derivative (1) featuring octyl substitution at γ-position, together with four known analogues (2-5) were isolated from marine-derived Streptomyces koyangensis SCSIO 5802. The structure of 1 was elucidated by HR-MS and NMR spectroscopic data analyses. The absolute configuration of the stereo centre in lactone ring of 1 was determined by comparison of CD spectrum with those of known compounds. Compound 1 exhibited mild antiviral activity against herpes simplex virus with EC50 value of 25.4 µM.

Keywords: (4S)-10-hydroxy-10-methyl-11-oxo-dodec-2-en-1,4-olide; Butenolide; Streptomyces koyangensis; antiviral activity; marine actinomycete.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry*
  • 4-Butyrolactone / isolation & purification
  • 4-Butyrolactone / pharmacology
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology
  • Herpes Simplex / drug therapy*
  • Herpes Simplex / physiopathology
  • Magnetic Resonance Spectroscopy
  • Streptomyces / chemistry*

Substances

  • Antiviral Agents
  • butenolide
  • 4-Butyrolactone

Supplementary concepts

  • Streptomyces koyangensis