Polysubstituted Cyclopentene Benzamides and Dianthramide Alkaloids from Delphinium anthriscifolium Hance

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 beta-D-glucose unit. Compound 13 bears a chlorine substituent. At a concentration of 10 mu M, 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%.

Automated summary

Thirteen new benzamide alkaloids were isolated from Delphinium anthriscifolium. Compound 1 possesses a previously undescribed carbon framework. Compound 2 is an artifact formed during the extraction process. Compound 7 is glycosylated while compound 13 contains a chlorine substituent. Compounds 6, 8, and 10-12 showed significant inhibition of LPS-induced NO production in cells.