Rinderidine and oblongifolidine new pyrrolizidine alkaloids from Rindera oblongifolia M. Popov and their absolute configurations

Nat Prod Res. 2024 Apr;38(7):1157-1167. doi: 10.1080/14786419.2022.2134865. Epub 2022 Oct 18.

Abstract

The alkaloid composition of Rindera oblongifolia was studied, in which the pyrrolizidine alkaloids echinatine and trachelanthamine N-oxide, as well as two new quaternary salts namely rinderidine and the oblongifolidine were isolated. The structures of the isolated new alkaloids were elucidated by NMR spectroscopy. The absolute configuration of lindelofine, trachelanthamine N-oxide, rinderidine and oblongifolidine was established by single crystal X-ray diffraction as: 1 R, 4 R, 8 R, 2'S, 3'R; 1 R, 4S, 8S, 2'S, 3'R; 4 R, 7S, 8 R, 2'S, 3'S; 4 R, 7S, 8 R, 2'S, 3'S (7''S, 8''R) respectively. Both new pyrrolizidine alkaloids showed no cytotoxicity against four cancer cell lines such as HeLa, НEр-2, HBL-100 and CCRF-CEM.

Keywords: Rindera oblongifolia; X-ray analysis; absolute configuration; cytotoxicity; pyrrolizidine alkaloids.

MeSH terms

  • Alkaloids* / chemistry
  • Alkaloids* / pharmacology
  • Antineoplastic Agents*
  • Boraginaceae* / chemistry
  • HeLa Cells
  • Humans
  • Oxides
  • Pyrrolizidine Alkaloids* / chemistry
  • Pyrrolizidine Alkaloids* / pharmacology

Substances

  • Pyrrolizidine Alkaloids
  • Alkaloids
  • Antineoplastic Agents
  • Oxides