New diterpenoid alkaloids from Aconitum heterophyllum Wall: Selective butyrylcholinestrase inhibitors

Figures & data

Table I.  ¹H- and ¹³C-NMR data of compound 1 and 2 (400 & 100 MHz, CDCl₃).

	Heterophyllinine-A (1)			Heterophyllinine-B (2)
C. No	δC	Multiplicity	δH, J HZ	δC	Multiplicity	δH, J HZ
1	41.2	CH2	1.89, 1.52, m	41.2	CH2	1.05, 1.41, m
2	23.1	CH2	1.74, 1.56, m	20.5	CH2	1.61, 1.50, m
3	33.2	CH2	1.34, 0.94, m	28.0	CH2	1.58, 1.32, m
4	39.3	C	–	41.0	C	–
5	38.0	CH	2.26, br s	50.1	CH	0.88, br s
6	28.8	CH2	1.71, m	77.9	CH	3.29, m
7	40.9	CH	2.40, m	41.8	CH2	1.67, 1.44, m
8	38.7	C	–	41.0	C	–
9	50.1	CH	2.02, t, 11.6	41.3	CH	0.59, m
10	50.5	C	–	38.0	C	–
11	27.5	CH2	0.93, 0.87, m	29.2	CH2	0.98, 0.86, m
12	38.0	CH	1.46, m	33.2	CH	1.90, m
13	27.5	CH2	1.41, 1.39, m	27.5	CH2	1.74, 1.52, m
14	29.1	CH2	1.70, 1.59, m	27.5	CH2	1.45, 0.98, m
15	77.8	CH	3.50, br s	77.9	CH	3.49, br s
16	156.7	C	–	156.8	C	–
17	110.3	CH2	5.03, 4.98, br s	110.2	CH2	5.03, 4.98, br s
18	20.5	CH3	0.82, br s	23.1	CH3	0.98, br s
19	51.0	CH2	2.91, 2.83, d, 10.27	100.0	CH	4.01, s
20	60.6	CH	3.62, d, 5.92	51.0	CH2	2.91, 2.82, d,
	59.6	CH2	3.07, 2.45, m	55.8	CH2	10.26
	55.8	CH2	3.15, t, 10.88	59.6	CH2	3.28, 2.54, m
	–	–	–	169.5	C	3.91, 3.79, m
	–	–	–	24.3	CH3	–
						2.02, br s

Table II.  Inhibition of acetylcholinestrase (AChE) and butyrylcholinestrase (BChE) by compounds 1, 2 and galanthamine.

Enzymes	Compounds	IC50 (μM) ± SEM	% Inhibition
AChE	Compound (1)	–	4.24
AChE	Compound (2)	–	6.94
BChE	Compound (1)	32.97 ± 0.533	79.1
BChE	Compound (2)	40.63 ± 1.11	82.75
AChE	Galanthamine^a	0.5 ± 0.001	85.21
BChE	Galanthamine^b	8.5 ± 0.02	81.36

^a,b Standard inhibitors of AChE and BChE