Sulfated Purine Alkaloid Glycosides from the Pupal Case Built by the Bruchid Beetle Bruchidius dorsalis Inside the Seed of Gleditsia japonica

Chem Biodivers. 2018 Aug;15(8):e1800154. doi: 10.1002/cbdv.201800154. Epub 2018 Jul 3.

Abstract

Three new sulfated isoguanine alkaloid glycosides, designated as saikachinoside A monosulfate (1), saikachinoside A disulfate (2), and locustoside B disulfate (3), have been isolated from the pupal case of the wild bruchid seed beetle Bruchidius dorsalis (Chrysomelidae, Bruchinae) infesting the seed of Gleditsia japonica Miq. (Fabaceae). Their structures were determined by spectroscopic methods and the inhibitory activity of 2 and 3 against acid phosphatase was evaluated.

Keywords: Bruchidius dorsalis; Gleditsia japonica; bruchid seed beetle; pupal case; sulfated purine alkaloid.

MeSH terms

  • Acid Phosphatase / antagonists & inhibitors
  • Acid Phosphatase / metabolism
  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Coleoptera / chemistry*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology
  • Gleditsia / chemistry*
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Molecular Conformation
  • Pupa / chemistry
  • Purines / chemistry
  • Purines / isolation & purification
  • Purines / pharmacology*
  • Seeds / chemistry*
  • Structure-Activity Relationship
  • Sulfates / chemistry
  • Triticum / enzymology

Substances

  • Alkaloids
  • Enzyme Inhibitors
  • Glycosides
  • Purines
  • Sulfates
  • Acid Phosphatase
  • purine