Cyclopeptide Alkaloids from Discaria chacaye (Rhamnaceae) as Result of Symbiosis with Frankia (Actinomycetales)

Chem Biodivers. 2022 Sep;19(9):e202200630. doi: 10.1002/cbdv.202200630. Epub 2022 Aug 17.

Abstract

Cyclopeptide alkaloids with different biological activities are present in plants of the family Rhamnaceae. Plants of this family grow in a symbiotic relationship with aerobic Gram-positive actinomycetes belonging to the genus Frankia. This goal of this research was a study of the comparative profile of alkaloids present in Discaria chacaye and to establish a connection between the presence or absence of Frankia sp. and the alkaloids. In addition, insecticidal activities of the alkaloidal extract were examined. A total of 24 alkaloids were identified, of which 12 have a benzylisoquinoline skeleton, 9 were cyclopeptides, 2 isoquinolines, and 1 aporphine. The presence of cyclopeptide alkaloids is associated with Frankia nodules in the plant root. The alkaloid extracts showed insecticidal activity with mortality dose-dependence and LD50 values between 44 to 71 μg/mL.

Keywords: Discaria chacaye; Frankia genus; Rhamnaceae; benzylisoquinoline alkaloids; cyclopeptide alkaloids.

MeSH terms

  • Actinobacteria*
  • Actinomycetales*
  • Alkaloids* / pharmacology
  • Aporphines*
  • Benzylisoquinolines*
  • Frankia*
  • Isoquinolines
  • Peptides, Cyclic / pharmacology
  • Plant Extracts
  • Plants
  • Rhamnaceae*
  • Symbiosis

Substances

  • Alkaloids
  • Aporphines
  • Benzylisoquinolines
  • Isoquinolines
  • Peptides, Cyclic
  • Plant Extracts