Quinoxaline-, dopamine-, and amino acid-derived metabolites from the edible insect Protaetia brevitarsis seulensis

Arch Pharm Res. 2017 Sep;40(9):1064-1070. doi: 10.1007/s12272-017-0942-x. Epub 2017 Aug 5.

Abstract

Edible insects have been reported to produce metabolites showing various pharmacological activities, recently emerging as rich sources of health functional food. In particular, the larvae of Protaetia brevitarsis seulensis (Kolbe) have been used as traditional Korean medicines for treating diverse diseases, such as breast cancer, inflammatory disease, hepatic cancer, liver cirrhosis, and hepatitis. However, only few chemical investigations were reported on the insect larvae. Therefore, the aim of this study was to discover and identify biologically active chemical components of the larvae of P. brevitarsis seulensis. As a result, a quinoxaline-derived alkaloid (1) was isolated, which was not reported previously from natural sources. In addition, other related compounds (2, 4-10, 15, 16) were also encountered for the first time from the larvae. The structures of all the isolated compounds were established mainly by analysis of HRESIMS, NMR, and electronic circular dichroism data. Compound 5 exhibited inhibition of tyrosinase with IC50 value of 44.8 µM.

Keywords: Alkaloids; Protaetia brevitarsis seulensis; Quinoxaline; Tyrosinase.

MeSH terms

  • Amino Acids / chemistry
  • Amino Acids / isolation & purification*
  • Animals
  • Circular Dichroism
  • Coleoptera / metabolism*
  • Dopamine / chemistry
  • Dopamine / isolation & purification*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology
  • Inhibitory Concentration 50
  • Larva
  • Magnetic Resonance Spectroscopy
  • Medicine, Korean Traditional
  • Monophenol Monooxygenase / antagonists & inhibitors
  • Quinoxalines / chemistry
  • Quinoxalines / isolation & purification*

Substances

  • Amino Acids
  • Enzyme Inhibitors
  • Quinoxalines
  • Monophenol Monooxygenase
  • Dopamine