Chelidonium majus L. (Papaveraceae) is broadly distributed over Georgia. It is a perennial herbaceous plant, the alkaloids of which are known for their cytotoxic activity [1]. The alkaloids chelidonine, protopine, L-stylopine, chelerythrine, and berberine were isolated earlier during studies of the species growing in Georgia [2].

Herein we communicate results of further research on the composition of alkaloids in C. majus. The specimen was the aerial part of the plant collected near Tbilisi during seed ripening.

Ground herb (2 kg) was extracted with EtOH by standing at room temperature. The organic solvent was distilled off. The thick extract was treated with HCl (5%) and then made basic using NH4OH (25%). Alkaloids were extracted with CHCl3 to afford an amorphous total that was separated over a column of silica gel with gradient elution by CHCl3:MeOH (1:0→0:1, v/v) to afford two bases that were identified based on an analysis of spectral data compared with the literature. 1H and 13C NMR spectra were recorded in CDCl3 + CD3OD on a Bruker-400 spectrometer (400 MHz for 1H; 100, for 13C).

HPLC analysis of the total was performed on an Agilent-1100 chromatograph using Silicagel-ODS (250 × 6 mm), 25°C, mobile phase H2O + AcCN (pH 7.5) at flow rate 1 mL/min.

Compound 1, white crystalline base, mp 206–208°C (CHCl3:EtOAc). PMR spectrum (400 MHz, δ, ppm, J/Hz): 2.57–2.72 (2H, m, H-6a/H-5a), 2.73–2.89 (1H, t, H-13), 3.02–3.18 (2H, m, H-5b/H-6b), 3.2–3.3 (1H, dd, J = 11.0), 3.47–3.63 (2H, t), 4.1 (1H, d, J = 15.3), 5.7–6.3 (4H, 2OCH2O), 6.6 (1H, s, H-4), 6.35 (1H, d, J = 8.0, H-12), 6.69 (1H, d, J = 8.0, H-11), 6.73 (1H, s, H-1). 13C NMR spectrum (100 MHz, δ, ppm): 105.42 (C-1), 144.86 (C-2), 146.07 (C-3), 108.32 (C-4), 127.64 (C-4a), 29.45 (C-5), 51.12 (C-6), 52.80 (C-8), 117.0 (C-8a), 146.07 (C-9).

HPLC analysis of total alkaloids showed that the retention time of chelidonine was 45.559 min; of tetrahydrocoptisine, 47.555; of stylopine, 54.125. A comparison of the results with the literature identified 1 as tetrahydrocoptisine [3–5].

Compound 2, amorphous base. PMR spectrum (400 MHz, δ, ppm): 2.5–2.75 (2H, m, H-5a/H-6b), 3.01–3.3 (2H, m, H-5b/H-6a), 4.8 (6H, s, 2 × OCH3), 6.0 (2H, s, OCH2O), 6.72 (1H, s, H-4), 6.74 (1H, d, H-12), 6.81 (1H, d, H-11), 7.01 (1H, s, H-1). 13C NMR spectrum (100 MHz, δ, ppm): 107.24 (C-1), 147.12 (C-2), 147.00 (C-3), 108.72 (C-4), 126.8 (C-4a), 29.43 (C-5), 51.0 (C-6), 54.06 (C-8), 116.5 (C-8a), 149.55 (C-9), 145.67 (C-10), 109.75 (C-11), 123.83 (C-12), 128.0 (C-12a), 36.44 (C-13), 63.0 (C-14), 131.21 (C-14a), 102.31 (2,3-OCH2O), 55.78 (C-10, OCH3), 59.5 (C-9, OCH3).

According to an analysis of the results and a comparison with the literature, 2 was identified as tetrahydroberberine [3, 5].