TABLE III.

¹³C-NMR Data of Manzamine-type Alkaloids in CDCl₃.

Alkaloids 1-8
Atom	1 (9)	2 (8)	3 (8)	3a (22)^a	4 (7)^b	5 (9)	6 (9)	7 (11)	8 (10,27)
1	143.6s	146.2s	145.8s	53.9d	60.0d	142.8s	142.5s	143.3s	59.9d
3	137.5d	137.0d	137.4d	42.1t	66.9t	138.4d	137.8d	137.9d	43.2t
4	113.8d	113.7d	113.0d	21.7t	43.6t	113.4d	113.7d	114.7d	22.4t
4a	129.3s	129.2s	128.1s	109.5s	127.7s	129.4s	130.2s	129.8s	109.0s
4b	121.1s	121.1s	121.9s	128.0s	109.4s	121.6s	122.8s	123.2s	127.8s
5	120.9d	121.3d	121.6d	119.0d	119.2d	121.3d	112.0d	112.6d	118.0d
6	119.2d	118.8d	119.0d	120.3d	118.0d	119.9d	120.9d	120.7d	119.3d
7	127.9d	128.8d	127.6d	123.1d	129.8d	128.3d	113.0d	114.3d	121.4d
8	112.8d	111.3d	111.8d	112.2d	111.0d	111.9d	143.4s	143.8s	111.0d
8a	141.4s	140.5s	140.6s	138.1s	141.0s	140.6s	129.9s	130.6s	135.5s
9a	133.3s	134.9s	135.5s	115.9s	133.8s	133.3s	133.2s	132.9s	134.2s
10	141.2s	44.5d	34.7t	27.7t	135.4s	140.3s	140.9s	141.9s	143.9s
11	135.1d	60.2d	52.8t	52.9t	134.5d	138.0d	137.3d	134.6d	130.1d
12	71.3s	60.4s			69.8s	68.4s	69.0s	71.2s	70.1s
13	39.1t	18.6t	48.9t	48.9t	40.9t	40.5t	39.9t	39.2t	40.6t
14	20.6t	22.7t	26.0t	23.0t	21.9t	21.2t	21.4t	20.7t	21.9t
15	126.8d	127.7d	23.3t	25.0	128.7d	127.9d	127.9d	126.7d	129.4d
16	132.8d	131.8d	24.9t	26.8t	132.2d	132.0d	130.1d	133.0d	129.1d
17	24.9t	23.5t	130.9d	132.1d	33.3t	25.2t	25.5t	24.7t	29.1t
18	26.4t	26.7t	130.9d	132.1d	27.1t	26.3t	26.6t	26.5t	28.6t
19	24.5t	24.3t	24.9t	26.8t	22.7t	24.8t	25.0t	24.5t	29.2t
20	53.3t	50.8t	23.3t	25.0t	53.6t	52.5t	52.8t	53.4t	53.4t
21			26.0t	23.0t	23.0t
22	49.1t	47.5t	48.9t	48.9t	49.8t	49.3t	49.6t	49.1t	49.6t
23	33.5t	32.3t			32.0t	33.2t	34.0t	33.4t	32.3t
24	41.0d	32.5d			37.9d	41.7d	42.3d	41.3d	44.6d
25	46.9s	44.0s			47.6s	46.5s	47.3s	47.1s	43.5s
26	78.0d	59.7d			75.5d	80.8d	81.7d	78.3d	59.2d
28	53.3t	39.4t			55.1t	52.6t	53.0t	53.7t	59.2t
29	26.2t	23.4t			26.2t	32.4t	32.7t	26.4t	29.2t
30	24.2t	18.1t			25.9t	44.3t	45.1t	24.2t	29.2t
31	28.3t	27.9t			28.4t	214.8s	216.2s	28.4t	25.0t
32	142.3d	132.3d			136.4d	38.7t	38.8t	142.8d	131.6d
33	123.5d	131.3d			121.4d	24.4t	24.4t	123.3d	131.1d
34	57.0d	27.3t			51.0t	63.2d	63.6d	57.4d	26.2t
35	44.7t	44.7t			44.8t	46.5t	46.6t	44.8t	37.3t
36	70.3t	56.6t			68.8t	68.4t	69.0t	70.2t	65.7t
Alkaloids 9–17
Atom	9 (10)	10 (27)	11 (17)	12 (14)	13 (14)	14 (12)	15 (13)	16 (13)	17 (17)

1	144.1s	56.1d	145.6s	142.9s	143.3s	158.9s	60.8d	69.5d	158.8s
3	138.6d	41.3t	139.6d	137.9d	137.0d	48.8t	43.9t	53.0t	48.8t
4	113.4d	21.7t	115.3d	113.4d	113.9d	19.1t	22.3t	21.9t	19.2t
4a	129.4s	109.7s	123.5s	129.0s	129.1s	117.1s	110.3s	110.3s	116.2s
4b	121.9s	126.6s	132.1s	122.3s	121.7s	125.5s	129.5s	129.0s	126.0s
5	121.6d	117.1d	123.1d	106.7d	106.0d	119.7d	109.5d	109.3d	103.4d
6	120.0d	118.6d	121.7d	150.3s	149.8s	120.2d	119.9d	119.9d	149.8s
7	129.4d	120.6d	130.3d	118.5d	118.4d	124.3d	106.8d	106.9d	114.5d
8	111.7d	110.0d	114.1d	112.3d	113.3d	121.1d	143.0s	143.1s	112.9d
8a	140.2s	134.8s	135.7s	134.7s	136.2s	136.1s	125.1s	125.3s	135.2s
9a	133.8s	132.6s	141.3s	134.3s	134.0s	127.6s	144.8s	144.9s	128.3s
10	142.5s	143.3s	143.5s	139.8s	141.3s	139.0s	132.8s	131.6s	138.9s
11	131.7d	128.6d	138.4d	136.6d	134.9d	140.8d	132.7d	132.1d	140.2d
12	70.4s	68.9s	70.7s	69.4s	71.2s	69.9s	70.6s	71.1s	69.9s
13	40.9t	39.6t	50.5t	41.7t	39.2t	40.5t	39.6t	39.8t	40.3t
14	22.2t	21.0t	128.3d	21.8t	20.8t	21.6t	20.6t	20.6t	21.4t
15	128.2d	128.4d	140.6d	128.5d	126.9d	128.4d	127.6d	126.8d	128.9d
16	131.2d	127.9d	74.4d	132.3d	132.8d	132.3d	131.7d	132.9d	132.4d
17	32.5t	28.1t	37.2t	26.1t	25.0t	25.9t	24.9t	24.8t	25.5t
18	28.7t	27.5t	27.4t	26.3t	26.4t	25.8t	26.4t	26.3t	26.2t
19	29.2t	28.2t	22.5t	22.9t	24.6t	25.6t	24.4t	24.4t	25.1t
20	53.5t	52.8t	55.9t	53.2t	53.4t	53.4t	53.3t	53.2t	53.4t
22	49.7t	48.6t	45.3t	49.8t	49.2t	49.5t	49.1t	49.1t	49.4t
23	29.2t	31.7t	33.3t	32.5t	33.4t	32.5t	33.7t	33.4t	32.6t
24	46.7d	46.2d	42.2d	39.3d	40.8d	40.8d	37.5d	37.4d	38.2d
25	43.5s	42.9s	49.1s	45.4s	47.0s	46.9s	46.7s	44.6s	46.8s
26	59.2d	58.1d	74.7d	75.2d	78.0d	75.1d	78.9d	78.9d	75.2d
28	37.5t	58.1t	53.1t	55.3t	53.4t	50.9t	53.5t	53.3t	51.2t
29	26.2t	28.2t	34.5t	28.0t	26.4t	31.3t	26.3t	26.3t	29.6t
30	25.1t	28.2t	27.2t	26.8t	24.3t	25.6t	24.0t	24.0t	28.2t
31	29.2t	24.1t	30.1t	79.6d	28.3t	28.1t	28.6t	28.7t	25.8t
32	131.0d	130.6d	136.9d	40.7t	142.4d	134.9d	142.5d	142.1d	135.2d
33	129.4d	130.0d	131.4d	36.9t	123.6d	129.6d	123.6d	123.6d	128.2d
34	59.2t	25.1t	57.3d	103.9s	57.1d	55.0t	57.5d	57.5d	55.2d
35	29.2t	37.0t	45.3t	51.4t	44.7t	44.5t	43.2t	42.5t	44.6t
36	65.6t	64.9t	65.6t	66.5t	70.3t	68.6t	70.9t	70.9t	68.9t
N-Me								44.4q

Alkaloids 18–22, and 25
Atom	18 (17)	19 (16)^c	20 (16)^c	21 (16)^c	22 (16)^c	25 (15)	25 (15)
						Unit A	Unit B
1	159.8s	143.8s	135.0s	135.0s	136.6s	147.6s	57.5d
3	48.8t	137.8d	132.9d	133.1d	61.9t	136.6d	38.4t
4	19.1t	113.5d	115.2d	115.3d	20.3t	113.6d	23.3t
4a	117.1s	129.4s	120.5s	120.3s	108.3s	129.3s	107.7s
4b	125.5s	122.1s	122.5s	122.5s	126.5s	120.9s	127.2s
5	119.7d	121.8d	121.2d	121.2d	119.1d	121.0d	117.9d
6	120.1d	120.3d	121.3d	121.4d	121.0d	118.5d	118.2d
7	124.2d	129.0d	127.8d	127.8d	123.5d	127.4d	120.2d
8	112.0d	112.0d	112.0d	111.9d	112.0d	110.6d	110.5d
8a	136.1s	140.5s	141.3s	141.1s	137.8s	140.7s	135.9s
9a	127.7s	133.9s	136.8s	136.9s	129.9s	135.8s	135.3s
10	140.1s	140.0s	141.3s	137.8s	134.5s	53.0d	38.8d
11	133.5d	138.8d	140.8d	134.6d	141.1d	58.8d	74.7d
12	70.2s	69.7s	70.0s	70.5s	69.9s	60.3s	64.2s
13	40.7t	41.9t	41.3t	41.0t	41.2t	40.1t	31.1t
14	21.9t	22.2t	22.0t	26.5t	21.9t	24.0t	18.7t
15	129.3d	128.6d	128.8d	131.1d	128.8d	130.8d	130.2d
16	129.2d	132.6d	132.9d	132.4d	132.9d	132.2d	130.8d
17	29.1t	NR	NR	NR	NR	24.9t	24.9t
18	28.6t	NR	NR	NR	NR	28.2t	27.6t
19	29.1t	NR	NR	NR	NR	26.1t	26.9t
20	53.4t	NR	NR	NR	NR	52.8t	46.8t
22	49.5t	NR	NR	NR	NR	127.3d	62.0d
23	32.3t	NR	NR	NR	NR	116.3s	23.0t
24	45.0d	NR	NR	NR	NR	34.6d	40.3d
25	43.2s	NR	NR	NR	NR	35.6s	45.2s
26	59.2d	78.8d	75.3d	59.4d	75.1d	60.6d	66.8d
28	59.2t	55.8t	51.4t	54.8t	51.3t	47.7t	48.3t
29	29.1t	23.2t	33.7t	29.8t	33.9t	26.9t	27.6t
30	29.1t	37.4t	26.0t	29.0t	26.0t	28.1t	26.6t
31	25.0t	79.8d	28.4t	32.9t	28.4t	23.4t	24.2t
32	131.0d	28.4t	134.7d	130.0d	134.8d	129.5d	130.6d
33	131.4d	41.0t	130.4d	129.5d	130.3d	132.5d	131.2d
34	26.2t	104.2s	55.7d	25.4t	55.0d	18.4t	20.9t
35	37.4t	51.9t	43.9t	22.8t	44.1t	32.9t	32.7t
36	65.6t	67.1t	69.3t	65.8t	63.9t	49.9t	56.3t

¹³C−, ¹⁵N-NMR Data of Manzamine-type Alkaloids 26, 57-59 in CDCl₃^d
Atom	26 (18)	26 (18)	57 (58)	58 (58)	59 (58)
	Unit A	Unit B
1	142.8s	143.0s	143.9s	142.6s	143.8s
N2	273.7s	273.7s	298.0s	299.0s	ND
3	138.7d	138.8d	138.8d	138.3d	138.2d
4	113.4d	113.5d	114.2d	114.3d	113.9d
4a	129.3s	129.4s	129.9s	130.1s	130.1s
4b	121.8s	121.8s	122.0s	123.4s	112.0s
5	121.6d	121.6d	121.8d	111.9d	122.1d
6	120.1d	120.1d	120.4d	120.9d	120.6d
7	128.4d	128.4d	128.8d	113.6d	128.4d
8	111.5d	111.5d	112.3d	143.6s	111.9d
8a	139.8s	139.9s	140.8s	130.6s	140.3s
N9	83.6p	83.6p	109.0p	105.4p	ND
9a	133.5s	133.6s	133.8s	133.2s	133.2s
10	139.8s	140.8s	142.8s	140.1s	142.9s
11	137.2d	137.2d	132.7d	132.2d	135.5d
12	70.8s	69.3s	80.5s	80.3s	80.4s
13	40.4t	41.6t	40.3t	39.8t	41.4t
14	21.7t	21.8t	23.1t	22.5t	23.6t
15	128.0d	128.3d	129.9d	129.3d	127.8d
16	132.5d	132.8d	129.8d	129.4d	133.2d
17	25.9t	25.8t	25.4t	25.0t	24.6t
18	26.7t	26.7t	30.0t	29.7t	29.7t
19	25.6t	26.1t	30.1t	29.6t	30.1t
20	44.6t	53.1t	59.3t	58.9t	58.8t
N21	13.5s	13.0s	36.1s	NO	ND
22	49.6t	49.7t	50.1t	49.7t	49.3t
23	32.4t	32.2t	32.1t	32.8t	33.8t
24	39.8d	39.2d	46.3d	45.9d	43.2d
25	45.3s	45.3s	38.6s	38.0s	39.9s
26	75.5d	75.9d	67.2d	66.8d	68.8d
N27	57.4s	37.4s	73.5s	73.2s	ND
28	47.2t	44.6t	54.1t	53.7t	54.1t
29	29.7t	30.0t	23.3t	22.7t	22.4t
30	72.2d	72.7d	33.1t	31.7t	33.9t
31	84.4d	67.2d	206.2s	205.1s	29.6t
32	39.5t	22.8t	30.9t	30.5t	133.4d
33	26.5t	26.6t	30.5t	30.0t	124.1d
34	89.7s	104.5s	101.8s	101.6s	94.9s
35	53.1t	51.2t	47.4t	47.2t	49.1t
36	68.7t	67.0t	66.3t	66.0t	69.9t

¹³C-NMR Data of Manzamine-related Natural Alkaloids 27, 28, 30, 35–39 in CDCl₃.
Atom	27 (14)	28 (14)	30 (22)^a	35 (10)	36 (10)	37 (25)	38 (25)	39 (26)
1	136.4s	155.8s		193.3d	194.3d	66.0t	65.2t	64.3d
2			42.8t
3	137.9d	49.1t	23.8t					53.6t
4	118.4d	18.8t	25.1t					38.0d
4a	131.5s	118.0s						43.3d
4b	120.6s	124.7s
5	121.7d	120.3d	26.5t					27.6t
6	120.5d	119.9d	132.2d					47.4t
7	129.6d	125.1d	132.2d
8	111.8d	112.2d	26.5t					50.8t
8a	140.8s	136.9s						45.1s
9			25.1t					141.8s
9a	136.5s	125.1s
10	184.2s	182.9s	23.8t	142.6s	144.7s	144.3s	143.8s	122.6d
11	129.7s	126.3s	42.8t	157.6d	151.7d	130.4d	126.8d	54.1t
12				70.2s	69.9s	71.6s	70.6s	26.1t
13	143.6d	144.2d		38.9t	40.4t	42.1t	41.2t	25.6t
14				21.0t	21.4t	23.0t	22.6t	22.9t
15	143.3d	144.2d		127.9d	129.3d	129.1d	130.5d	131.2d
16				132.5d	131.4d	134.6d	128.9d	130.9d
17				25.6t	29.2t	27.1t	30.0t	21.0t
18				26.7t	29.2t	28.6t	29.6t	41.6t
19				25.3t	26.2t	26.9t	25.5t	56.2t
20				53.5t	37.1t	55.0t	59.4t	21.1t
21								27.2t
22				49.4t	49.5t	51.2t	49.9t	25.0t
23				31.6t	31.4t	33.6t	30.2t	131.5d
24				34.0d	40.2d	39.9d	44.1d	132.0d
25				46.4s	42.6s	48.7s	43.9s	25.6t
26				76.3d	59.8d	78.8d	60.3d	37.0t
28				51.4t	53.5t	54.5t	52.4t
29				29.8t	29.2t	30.1t	29.4t
30				25.3t	25.0t	26.5t	29.7t
31				28.2t	28.6t	29.7t	23.0t
32				137.1d	131.2d	141.5d	130.9d
33				127.7d	129.2d	127.6d	132.0d
34				55.4d	59.3d	55.8d	29.7d
35				44.6t	29.2t	46.3t	37.5t
36				69.2t	65.6t	71.3t	65.3t
N-Me	35.2q	35.2q

¹³C−, ¹⁵N-NMR Data of Manzamine-type Alkaloids 60–66 in CDCl₃^d
Atom	60 (61)	61 (61)	62 (59)	63 (59)	64 (60)	65 (60)	66 (60)
1	61.3	69.2	53.5	60.1	143.1s	143.5,s	139.4,s
N2	ND	ND	46.3	40.4	ND	ND	ND
3	43.7	53.0	49.3	23.0	137.7d	136.7d	116.2d
4	22.2	22.0	23.0	108.3	113.7d	113.6d	129.5d
4a	109.4	109.4	108.7	127.4	130.3s	129.9s	134.8s
4b	136.2	136.5	127.4	118.2	121.6s	122.2s	123.5s
5	117.4	117.4	118.2	111.9	121.3d	105.3d	105.6d
6	120.8	120.8	119.0	118.9	119.9d	151.4s	153.2s
7	118.5	118.6	121.3	121.3	128.5d	118.5d	123.1d
8	112.0	111.9	111.3	111.3	112.3d	113.0d	114.1d
8a	127.0	126.7	136.1	136.1	141.1s	134.7s	139.4s
N9	ND	ND	123.8	ND	ND	ND	ND
9a	132.5	143.3	134.7	134.9	133.8s	136.1s	136.9s
10	144.1	143.3	43.0	40.4	141.7s	139.5s	143.7s
11	132.5	133.4	74.5	74.7	137.2d	136.9d	143.7d
12	70.7	71.0	64.7	64.6	68.6s	69.9s	72.5s
13	39.5	39.6	31.0	31.4	40.5t	41.0t	41.2t
14	20.6	20.6	18.6	18.7	21.7t	21.9t	21.6t
15	127.2	127.0	130.0	130.1	127.8d	128.7d	134.8d
16	132.8	132.9	131.1	131.0	132.7d	132.0d	127.5d
17	24.9	24.9	25.0	25.0	25.7t	26.3t	23.6t
18	26.4	26.4	27.6	27.6	26.9t	27.1t	26.1t
19	24.5	24.5	27.0	27.0	25.0t	22.8t	22.8t
20	53.3	53.2	46.6	46.7	52.8t	53.5t	53.2t
N21	ND	ND	36.9	ND	ND	ND	ND
22	49.1	49.3	57.9	58.6	49.8t	50.2t	49.7t
23	33.9	33.6	26.8	27.9	33.4t	32.5t	31.5t
24	37.1	37.5	33.6	39.4	42.4d	40.1d	39.5d
25	46.8	46.9	45.2	45.3	45.9s	45.5s	42.7s
26	78.8	78.8	66.9	66.7	81.9d	75.6d	79.7d
N27	ND	ND	32.6	ND	ND	ND	ND
28	53.3	53.3	48.0	48.1	53.5t	53.5t	53.2t
29	26.2	26.2	27.3	27.4	31.7t	32.4t	38.1t
30	24.4	24.4	26.2	26.2	48.2t	48.2t	41.2t
31	28.3	28.3	24.3	24.3	70.6d	79.9d	25.8t
32	141.9	141.8	131.1	130.8	36.8t	37.2t	23.6t
33	124.1	124.1	130.8	130.6	25.0t	26.3t	31.5t
34	57.1	57.2	21.4	21.2	63.8d	65.4d	66.9d
35	43.1	42.6	33.3	33.1	46.2t	47.3t	197.2s
36	70.8	71.1	57.5	57.2	68.9t	66.9t	63.5t
37		44.2	45.2	49.6
38			208.6	207.4
39			30.9	30.6

Recorded in CD₃OD.

Recorded in C₆D₆+CD₃OD

19–22 were recorded in CD₂Cl₂. NR = not reported in the original literature.

Nitromethane was used as external standard for ¹⁵N-NMR, s = quaternary, p = protonated nitrogens. NO = not observed. ND = not determined.