Novel propanamide analogue and antiproliferative diketopiperazines from mangrove Streptomyces sp. Q24

Nat Prod Res. 2017 Jun;31(12):1390-1396. doi: 10.1080/14786419.2016.1253079. Epub 2016 Nov 3.

Abstract

A new propanamide analogue (1), along with one known alkaloid (2) and four known diketopiperazines (3-6), was isolated from a cultured broth of the actinomycete Streptomyces sp. Q24 that was obtained from a sample of mangrove soil. The structures of these isolates were characterised as 3-acetylamino-N-2-thienyl-propanamide (1), N-acetyltryptamine (2), cyclo-(l-phenylalanine-l-4-hydroxyproline) (3), cyclo-(l-leucine-l-4-hydroxyproline) (4), cyclo-(l-phenylalanine-d-4-hydroxyproline) (5) and cyclo-(l-leucine-l-proline) (6) based on their NMR and HRESIMS data as well as optical rotation. Three diketopiperazines (3, 4, 6) showed activity in inhibiting the proliferation of human glioma U87-MG and U251 cells. This type of the new propanamide analogue (1) is first found from a nature source and the antiproliferative property of these three diketopiperazines against glioma cells is also reported herein for the first time.

Keywords: Mangrove Streptomyces sp; antiproliferative activity; diketopiperazines; glioma cells; new propanamide analogue.

MeSH terms

  • Amides / chemistry
  • Amides / isolation & purification*
  • Amides / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Diketopiperazines / chemistry
  • Diketopiperazines / isolation & purification*
  • Diketopiperazines / pharmacology
  • Fermentation
  • Humans
  • Soil Microbiology
  • Streptomyces / metabolism*
  • Tryptamines / pharmacology

Substances

  • Amides
  • Antineoplastic Agents
  • Diketopiperazines
  • Tryptamines
  • N-acetyltryptamine