Quaternary alkaloids of Argemone mexicana

Figures & data

Figure 1.  Structure of alkaloids 1–4 isolated from the whole plant of Argemone mexicana.

Table 1.  500 MHz ¹H NMR (CDCl₃ + 20% CD₃OD) spectroscopic data of alkaloids 1–4.

Position of hydrogen	^1H NMR, δH (ppm) (multi, J in Hz)
	1	2	3	4
1	6.85 (1H, s)	7.45 (1H, s)	7.65 (1H, s)	6.85 (1H, s)
4	7.45 (1H, s)	7.05 (1H, s)	7.15 (1H, s)	7.45 (1H, s)
5	3.28 (2H, m)	3.19 (2H, m)	3.40 (2H, m)	3.38 (2H, t, 6)
6	5.05 (2H, m)	4.94 (2H, m)	5.14 (2H, m)	5.15 (2H, t, 6)
8	9.95 (1H, s)	9.60 (1H, s)	9.90 (1H, s)	—
11	7.91 (1H, m)	7.97 (1H, d, 8.5)	8.17 (1H, d, 9)	7.92 (1H, d, 8.5)
12	7.91 (1H, m)	7.89 (1H, d, 8.5)	8.10 (1H, d, 9)	7.90 (1H, d, 8.5)
13	8.40 (1H, s)	8.45 (1H, s)	8.75 (1H, s)	8.40 (1H, s)
2-OMe	4.25 (3H, s)	4.22 (3H, s)	—	—
3-OMe	4.10 (3H, s)	—	4.43 (3H, s)	—
2,3-O-CH2-O	—	—	—	6.10 (2H, s)
9-OMe	4.41 (3H, s)	4.07 (3H, s)	4.28 (3H, s)	4.18 (3H, s)
10-OMe	—	4.01 (3H, s)	4.22 (3H, s)	4.25 (3H, s)

Table 2.  125 MHz ¹³C NMR (CDCl₃ + 20% CD₃OD) spectroscopic data of alkaloids 1–4.

Position of carbon	^13C NMR, δC (ppm)
	1	2	3	4
1	114.36	114.68	108.75	108.8
2	149.06	149.97	148.72	140.0
3	150.97	144.18	150.70	152.5
4	108.54	108.36	105.36	105.5
4a	128.53	128.32	130.44	124.5
5	26.29	26.54	27.52	27.1
6	56.22	56.27	56.15	55.9
8	144.53	144.33	145.59	159.0
8a	119.48	121.67	122.22	122.7
9	148.33	148.06	144.98	148.0
10	144.06	150.33	151.02	152.0
11	126.00	126.53	126.88	127.1
12	121.67	119.67	120.15	119.0
12a	133.32	133.75	133.66	133.5
13	123.67	123.00	123.14	123.5
14	138.75	138.63	138.26	137.7
14a	117.68	117.48	120.26	117.0
2-OMe	56.33	56.33	—	—
3-OMe	56.27	—	56.26	—
2,3-O-CH2-O	—	—	—	102.0
9-OMe	61.84	61.99	62.44	62.0
10-OMe	—	56.84	57.15	56.8