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. 2009 Mar 23;14(3):1245–1262. doi: 10.3390/molecules14031245

Table 4.

13C-NMR data (in CDCl3) of diterpenes from Aristolochia species.

Carbon Compound / δC (in ppm)
1 [56] 2 [13] 3 [31] 4 [13] 6 [28] 8 [57,58] 10 [59] 11 [28] 12 [13] 13 [28] 14 [56] 15 [28] 16 [13] 17 [33] 18 [33]
1 42.0 39.2 40.3 40.9 40.35 41.1 40.4 39.82 40.4 40.66 41.0 40.73 42.0 39.10 41.13
2 18.6 18.2 18.6 18.6 17.97a 19.8 18.6 18.39a 18.7 19.06 18.5 19.05a 18.6 20.07 19.52
3 42.0 42.0 41.9 42.0 35.55 38.7 42.0 34.33 42.1 38.39 41.9 38.03 43.8 35.00 38.23
4 33.2 33.1 33.2 33.6 38.50 43.9 33.2 48.47 33.3 43.66 33.2 43.55 33.2 43.60 44.66
5 56.2 56.1a 56.2 56.1a 56.90b 57.0 56.2 56.68b 55.9 56.96 56.1 56.65 55.8 49.80 57.49
6 20.4 20.6 20.4 20.7 20.49 23.0 20.2 20.10 19.3 22.00 19.2 20.70 19.2 19.51 22.28
7 40.3 40.3 42.0 40.4 42.31 42.8 41.1 42.02 32.5 41.52 40.3 39.24 39.2 40.84 41.71
8 45.3 45.3 44.7 45.1 45.17 45.0 45.4 45.20 43.4 44.51 42.5 48.81 48.8 47.63 44.17
9 56.8 56.0a 56.7 56.0a 56.70b 56.3 55.9 55.20b 50.8 55.40 55.0 47.57 48.3 47.89 55.55
10 39.3 38.0 39.4 39.2 39.15 40.1 39.3 39.44 39.2 39.64 39.4 39.72 39.4 40.00 40.09
11 18.0 18.5 18.3 18.3 17.93a 19.0 19.3 18.13a 18.2 19.06 18.5 18.75a 18.6 77.52 18.43
12 26.9 31.2 26.3 31.3 26.06 26.8 29.2 26.90 27.0 27.06 29.7 25.31 25.6 33.97 33.53
13 49.0 44.7 45.5 41.4 48.64 45.9 42.7 48.93 36.0 45.64 47.9 40.92 41.1 44.41 44.28
14 37.7 40.8 37.3 38.1 37.36 37.8 38.6 37.81 36.0 37.88 37.5 43.71 40.4 39.79 40.13
15 58.0 45.0 53.4 44.7 57.66 53.9 48.9 57.80 65.7 55.54 55.2 135.39 135.7 47.41 49.39
16 79.4 55.9 81.9 45.9 79.16 81.7 66.4 79.29 69.5 89.16 222.5 145.82 145.6 155.24 156.32
17 24.5 182.5 66.4 14.8 24.05 66.5 50.4 24.47c 59.9 70.05 - 60.63 61.1 104.09 103.69
18 33.5 33.5 33.5 33.2 26.89 29.3 33.6 24.26c 33.6 28.93 33.6 28.87 35.5 30.08 29.38
19 21.6 21.5 21.5 21.6 64.98 180.1 21.6 205.80 21.6 182.64 21.7 180.90 21.5 184.05 184.00
20 18.0 17.3 17.8 17.4 18.11 16.0 17.8 16.40 17.5 15.74 18.0 15.25 17.6 15.93 16.02
1’ 108.39
2’ 26.81
3’ 26.91
Carbon Compound / δC (in ppm)
19 [56] 20 [57](?) 22 [34] 22 [34] (P) 22 [34](D) 23 [60] 27 [26] 27 [34] 29 [61] 30 [38] 30 [38] 31 [39] 32 [39] 33 [38] 33 [39]
1 41.3 40.5 39.79 40.9 40.3 38.7 18.3 17.4 17.3 17.5 18.2 17.7 17.6 17.3 18.3
2 18.7 18.3 20.07 19.7 19.0 27.6 26.8 27.6 27.5 27.1 26.8 24.1 24.0 27.5 26.9
3 42.0 35.7 40.84 38.5 37.9 80.6 120.5 120.6 120.4 120.0 120.4 123.2 123.1 120.5 120.4
4 33.3 39.3 43.60 43.7 42.5 42.7 144.5 144.4 144.4 143.7 144.4 139.9 139.9 144.5 144.4
5 56.1 56.9 49.80 49.5 46.3 55.8 38.2 38.3a 38.3 38.0a 38.4 38.5 38.2 38.3a 38.2
6 20.3 20.5 35.00 30.4 29.3 20.1 36.9 36.5 35.9 36.4 36.8 37.8 37.7 36.4b 36.8
7 40.4 41.7 77.52 76.2 75.0 41.3 27.6 27.0 26.8 26.4 27.5 28.8 28.7 26.9 27.5
8 44.2 44.0 47.63 48.9 48.0 43.9 36.2 36.3 36.1 36.0 36.1 37.3 37.2 36.4b 36.3
9 56.1 56.2 47.89 47.4 48.6 55.8 40.0 38.7a 38.1 38.3a 39.9 39.9 39.9 38.4a 38.3
10 39.3 38.7 40.00 39.5 38.8 39.6 46.4 46.6 46.4 46.1 46.3 44.5 44.5 46.6 46.5
11 18.1 18.2 19.51 18.5 17.7 18.3 35.5 35.1b 35.5 35.0b 35.4 35.1 35.0 35.0 36.3
12 33.3 33.2 33.97 34.0 33.3 33.0 29.5 35.6b 35.4 35.8b 29.4 29.4 29.3 36.9a 35.0
13 44.2 44.2 44.41 44.3 43.4 43.9 30.9 31.0 30.6 30.6 31.0 30.9 31.1 164.4 164.6
14 39.9 39.7 39.10 39.1 38.4 38.5 41.6 41.7 36.5 41.0 41.5 41.6 41.5 114.9 114.8
15 49.2 49.1 47.41 46.6 45.6 48.8 179.4 179.8 62.8 172.8 173.8 179.4 173.8 172.0 172.1
16 156.0 155.9 155.24 156.2 155.4 155.4 19.9 19.9 19.6 19.5 19.9 19.8 19.8 19.5 19.5
17 102.8 103.0 104.09 103.6 103.2 103.1 16.0 16.1 15.7 15.5 15.9 16.0 15.9 15.9 16.0
18 33.7 27.1 30.08 28.6 28.5 22.8 19.9 18.4 18.3 18.0 19.9 33.0 33.0 18.3 20.0
19 21.7 65.6 184.05 178.2 179.0 64.3 18.0 20.0 19.3 19.5 18.0 20.1 19.9 20.0 18.0
20 17.6 18.1 15.93 15.7 15.4 18.3 18.5 18.1 17.8 17.8 18.4 17.4 17.3 17.9 18.3
C=O 178.6
MeCO 20.8
OMe 50.6 51.3 51.3
Carbon Compound / δC (in ppm)
34 [62] 35 [63] 36 [38] 37 [38] 38 [40] 39 [41] 40 [41] 41 [41] 42 [41] 43 [41] 44 [38] 45 [40] 46 [40] 47 [38] 48 [41]
1 18.37 18.40 17.5 18.6 18.1 29.4 16.2 18.2 27.3a 28.9 35.1a 35.6 35.6 35.6a 34.3a
2 26.98 26.92 27.1 24.1 27.7 125.6 30.3 27.4 65.6 69.5 199.1 201.2 200.2 200.0 200.5
3 120.52 120.46 120.0 123.3 120.3 171.0 76.2 120.4 122.1 124.4 128.5 125.5 125.5 125.5 127.4
4 144.60 144.50 143.7 139.8 144.4 168.7 76.5 144.5 150.1 147.9 168.6 173.4 171.0 172.6 172.6
5 38.28 38.30 38.0a 37.9 38.3 50.6 38.3 38.1 38.0 38.0 38.6c 40.0 38.8 39.9b 39.7
6 36.94 36.99 36.4 37.6a 36.1 34.4 32.4 36.8 36.4 36.5 36.8b 36.0 35.5 34.8a 35.5
7 27.61 27.63 26.4 28.9 26.8 28.3 26.4 26.8 27.2a 27.2 29.0 27.0 26.9 26.9 26.8
8 36.36 36.41 36.0 37.5 36.8 37.1 36.0 36.1 36.3 35.9 37.3 36.1 36.1 36.1 35.8
9 38.72 38.72 38.3a 38.9 38.1 37.5 41.2 38.3 38.9 38.6 39.3c 38.6 38.6 38.8b 38.3
10 46.53 46.60 46.0 44.9 46.3 53.9 40.7 46.3 40.4 45.2 45.7 45.7 45.7 45.6 45.5
11 36.63 36.72 34.2 35.0 31.8 33.5 32.2 31.8 31.0 31.8 35.4a 34.9 34.9 34.9a 31.1
12 32.95 32.97 37.7 37.0a 35.2 35.5 35.4 35.3 36.4 35.2 36.2b 36.0 34.7 35.9a 34.7a
13 140.93 143.22 160.8 164.5 73.3 73.0 73.5 73.4 73.2 73.3 30.7 30.8 30.4 30.9 73.0
14 123.13 118.03 114.5 115.1 145.2 144.9 145.0 145.1 146.4 145.0 41.4 41.5 36.9 41.3 144.8
15 59.51 61.44 166.5 172.4 111.6 111.9 111.6 111.8 110.9 111.9 178.7 178.9 63.0 173.4 111.9
16 16.52 16.70 18.5 19.6 27.4 27.8 27.4 27.7 26.3 27.7 19.9 19.9 19.9 19.8 27.7
17 16.07 15.98 15.5 16.1 15.8 15.0 15.9 15.9 15.8 15.9 16.0 15.7 15.8 15.7 15.6
18 18.45 17.92 18.0 20.0 18.3 11.7 21.3 18.0 17.9 17.7 20.5 18.4 18.5 18.4 18.9b
19 20.03 19.99 19.5 33.2 19.8 16.9 17.2 19.8 18.3 19.9 32.1 18.9 18.7 18.9 18.2b
20 18.07 18.34 17.8 17.9 17.8 18.2 18.5 18.4 18.3 18.5 18.0 17.9 18.0 18.0 17.9
C=O 170.94 178.9
MeCO 20.94 20.8
OMe 50.1 51.4
Compound / δC (in ppm)
Carbon 49 [38] 50 [38] 51 [38] 54 [41] 56 [46] 57 [40] 58 [64] 60 [40] 61 [54]A 62 [55] 63 [65] 65 (?) [66] 66 [40] 67 [40]
1 35.4a 35.4a 35.6a 22.0 74.18 39.1 39.8 39.0 40.4 33.1 39.1 19.45 43.9 36.9
2 200.3 200.0 200.2 79.2 128.68 18.2 - 18.2 19.0 21.7 19.4 22.36 19.5 19.0
3 128.5 125.3 125.4 116.7 136.84 42.1 41.9 41.9 42.7 35.4 42.1 24.51 42.0 41.2
4 167.5 172.3 172.7 155.0 80.48 33.1 - 33.3 33.7 39.1 33.6 33.64 34.5 33.2
5 38.6b 39.8b 39.9b 37.8 37.16 55.9 56.1 55.8 56.9 36.6 55.5 55.59 57.5 51.8
6 36.7a 34.8a 34.9a 33.2 25.59 18.1 23.5 18.1 21.1 28.6 24.5 32.75 69.4 19.0
7 28.9 26.7 26.9 27.1 17.33 41.3 44.7 40.5 45.1 37.4 38.3 38.41 47.7 33.5
8 36.6 36.1 36.1 36.4 47.58 73.3 74.4 73.3 73.9 160.6 148.3 148.17 144.0 125.4
9 39.9b 38.7 38.7b 39.1 35.28 59.3 61.3 58.2 62.3 48.6 56.2 57.20 56.7 140.4
10 45.7 45.6 45.8 40.4 44.49 38.9 39.2 38.8 39.8 40.0 39.7 39.80 40.9 37.2
11 34.0 34.2a 34.0a 30.7 41.90 22.3 20.5 22.4 20.0 27.5 21.5 38.96 21.6 25.3
12 36.8a 35.9a 35.9a 36.1 70.66 42.1 44.5 41.9 46.2 29.8 40.1 42.21 39.5 41.7
13 160.3 162.6 160.3 73.9 124.79 30.9 163.9 30.9 73.3 30.8 164.3 160.69 160.7 31.1
14 115.2 115.1 115.3 146.3 108.40 40.5 114.7 144.7 147.5 41.4 114.6 115.73 115.2 145.9
15 167.0 171.2 167.1 111.2 139.66 177.9 171.5 111.8 110.7 179.8 171.8 166.40 167.3 112.0
16 19.1 19.3 19.1 25.0 143.96 19.5 19.4 19.5 27.8 19.8 19.2 14.51 19.0 20.0
17 15.9 15.5 15.7 15.6 175.48 30.5 24.0 30.4 24.5 102.5 106.4 21.73 110.3 19.4
18 20.5 18.2 18.4 18.3 172.37 21.5 21.5 21.5 33.7 18.2 33.6 25.26 23.6 21.5
19 32.1 18.7 18.9 18.1 27.00 33.3 33.4 33.1 21.8 20.8 21.7 33.64 33.7 33.2
20 17.8 17.6 17.9 18.4 24.31 - 15.4 - 15.8 15.9 14.5 106.53 17.1 19.3
1’ 50.8
2’
3’ 50.7 50.56 50.8

a, b, and c may be interchanged for the same structure; (*) reassigned 13C-NMR data in CDCl3; (P) 13C-NMR data in C5D5N; (D) 13C-NMR data in DMSO-d6; (A) 13C-NMR data in acetone-d6; (?) solvent not given