Eleven new C19-diterpenoid alkaloids from Delphinium elatum cv. Pacific Giant.

Abstract

Diterpenoid alkaloids, the main components of plants of the genera Aconitum, Delphinium, and Garrya, are a group of natural products with notable chemical properties and biological activities. Several C19-diterpenoid alkaloid components from Delphinium elatum cv. Pacific Giant, as well as their derivatives, exhibited cytotoxic activity against lung, prostate, cervical, and vincristine-resistant cervical cancer cell lines. In the current phytochemical investigation on the seeds of D. elatum cv. Pacific Giant, eleven new C19-diterpenoid alkaloids, elapaciline (1), meladine (2), melapacitine (3), iminoeladine (4), 19-oxopaciline (5), 19-oxopacinine (6), N-deethyldelpheline (7), N-deethylpacinine (8), N-deethyl-19-oxoeladine (9), N-deethyl-N-formyleladine (10), and N-deethyl-N-formyldelpheline (11), together with 15 known C19-diterpenoid alkaloids were isolated. Their structures were elucidated by extensive spectroscopic methods including NMR (1D and 2D), IR, and MS (HRMS). Three known diterpenoid alkaloids, 6-dehydrodelcorine (12), delelatine (23), and 6-dehydroeldelidine (24), were isolated for the first time from this plant. Six of the new C19-diterpenoid alkaloids (2, 4-7, and 11) and three of the known diterpenoid alkaloids (18, 23, and 24) were evaluated for cytotoxic activity against five human tumor cell lines.