Polysubstituted Cyclopentene Benzamides and Dianthramide Alkaloids from Delphinium anthriscifolium Hance

J Nat Prod. 2022 Apr 22;85(4):1157-1166. doi: 10.1021/acs.jnatprod.2c00107. Epub 2022 Apr 6.

Abstract

Thirteen new benzamide alkaloids, delphiniumines A-M (1-13), together with one known analogue (14), were isolated from Delphinium anthriscifolium Hance. All of the structures were determined by spectroscopic and spectrometric analyses. Absolute configuration for 1 was established using experimental and calculated ECD data, as well as by X-ray crystallography analysis. Compound 1 possesses a previously undescribed polysubstituted cyclopentene carbon framework. Compound 2 was isolated as an artifact from 1 during the extraction process. Compound 7 is glycosylated with a β-D-glucose unit. Compound 13 bears a chlorine substituent. At a concentration of 10 μM, compounds 6, 8, and 10-12 suppressed LPS-induced NO production in RAW264.7 cells with inhibition rates ranging from 40.3% to 78.8%.

Publication types

  • Review
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids* / chemistry
  • Benzamides
  • Cyclopentanes / pharmacology
  • Delphinium* / chemistry
  • Diterpenes* / chemistry
  • Molecular Structure

Substances

  • Alkaloids
  • Benzamides
  • Cyclopentanes
  • Diterpenes