Alkaloids from the stem bark of Strychnos icaja

作者:Tchinda Alembert T*; Tamze Victorine; Ngono Annie R N; Ayimele Godfred A; Cao Martine; Angenot Luc; Frederich Michel
来源:Phytochemistry Letters, 2012, 5(1): 108-113.
DOI:10.1016/j.phytol.2011.11.004

摘要

A comprehensive phytochemical study of the stem bark of Strychnos icaja was done for the first time and led to the isolation of two new monoindole alkaloids 15-hydroxyvomicine (1) and 12-methoxyicajine (2) along with 13 known alkaloids: the monoindoles N-methyl-sec-iso-pseudostrychnine (3), vomicine (4), icajine (5), 19,20-alpha-epoxy-12-methoxyicajine (6), 19,20-alpha-epoxy-12,15-dihydroxy-11-methoxyicajine (7), 19,20-alpha-epoxy-15-hydroxynovacine (8), 15-hydroxyicajine (9), 12-hydroxystrychnine (10), strychnine (11) and the tertiary bisindoles sungucine (12), isosungucine (13), strychnogucine C (14) and bisnordihydrotoxiferine (15). Apart from 10 and 11, the other alkaloids were isolated for the first time from the stem bark of this plant. The hemisynthetic derivative, N-b-chloromethosungucine (16) and the previously reported synthetic compound 3 were isolated from a natural source for the first time. Fractions and some isolated compounds were tested against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum. The bisindole alkaloids were most active with IC50 ranging from 0.72 to 3.41 mu g/ml whilst the monomers 1 and 3 were slightly active (IC50 39.92 and 40.27 mu g/ml respectively) and 6 inactive. The structures of the compounds were determined based on the analysis of their spectral data. The full H-1 and C-13 NMR data of compounds 3, 6 and 7 are also reported in the present work for the first time.