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. 2020 Jul 6;25(13):3079. doi: 10.3390/molecules25133079

Table 2.

1H- and 13C-NMR chemical shifts of 1–3 in DMSO-d6.

Terpendole N (1) a
Position δCc, type δHd (multi, J Hz) HMBC Position δCc, type δHd (multi, J Hz) HMBC
1-NH - 10.08 (s) 2, 18, 19, 24 18 76.8, C - -
2 180.2, C - - 18-OH - 5.72 (s) 18, 19
3 74.6, C - - 19 128.9, C - -
3-OH - 3.74 (s) 3, 16, 25 20 136.7, C - -
4 44.9, C - - 21 121.9, CH 6.81 (d, 7.6) 19, 23
5 23.2, CH2 1.15–1.21 (m) 4 22 128.8, CH 7.11 (t, 7.6) 20, 24
1.92 (m) 23 107.5, CH 6.63 (d, 7.6) 19, 21
6 28.1, CH2 1.32 (m) 4, 7, 12 24 141.7, C - -
1.88 (m) 25 19.5, CH3 1.08 (s) 3, 16
7 70.5, CH 4.02 (dd, 10.2, 7.4) 6, 11, 12 26 16.7, CH3 0.59 (s) 4, 5, 13
27 74, C - -
9 70.9, CH 3.34 (d, 9.6) 27, 28, 29 28 16.7, CH3 1.14 (s) 9, 27, 29
29 28.3, CH3 1.073 (s) 9, 27, 28
10 70.1, CH 3.92 (d, 9.6) - 31 92, CH 5.42 (d, 6.4) 10, 27, 34
11 59.1, CH 3.33 (br s) 7, 9, 12 33 122.5, CH 5.05 (br d, 6.4) 35, 36
12 66.8, C - - 34 137.5, C - -
13 75.9, C - - 35 18.4, CH3 1.61 (d, 1.2) 34, 36
13-OH - 4.18 (s) 4, 13, 14 36 25, CH3 1.63 (s) 34, 35
14 25.5, CH2 0.81–0.90 (m) 4 37 29.7, CH2 2.87 (m) 19, 20, 21, 39
1.04–1.08 (m) 3.03 (m)
15 23.7, CH2 1.10 (d, 4.8) 17 38 62.9, CH 3.02 (m) 20
1.27 (s) 39 57.8, C - -
16 37.5, CH 1.27–1.34 (m) - 40 18.9, CH3 1.27 (s) 41
17 37.1, CH2 1.68 (dd, 12.6, 10.6) 2, 3, 15, 18 41 24.7, CH3 1.23 (s) 38, 39, 40
2.29 (d, 12.6)
Terpendole O (2) a
Position δCc, type δHd (multi, J Hz) HMBC Position δCc, type δHd (multi, J Hz) HMBC
1-NH - 10.69 (s) 2, 18, 19, 24 18 114.3, C - -
2 152.3, C - - 18-OH - - -
3 49.9, C - - 19 124.1, C - -
3-OH - - - 20 128.0, C - -
4 42.1, C - - 21 118.2, CH 6.71 (d, 7.2) 19, 23
5 25.5, CH2 1.67 (br d, 6.4) 26 22 119.5, CH 6.86 (t, 7.6) 20, 24
2.42 (br d, 6.4) 23 110.1, CH 7.12 (d, 8.0) 19, 21
6 28.53, CH2 2.12 (br m) - 24 139.7, C - -
25 16, CH3 1.16 (s) 2, 3, 4
7 70.6, CH 4.26 (t, 8.8) 9, 11 26 18, CH3 1.02 (s) 3, 4, 5, 13
27 74.1, C - -
9 71, CH 3.40 (d, 9.6) 7, 27, 28, 29 28 16.7, CH3 1.22 (s) 9, 27, 29
29 28.2, CH3 1.12 (s) 9, 27, 28
10 70.1, CH 4.04 (d, 9.6) 27 31 91.9, CH 5.50 (d, 6.4) 10, 27, 34
11 58.9, CH 3.50 (br. s) 7, 9, 12 33 122.5, CH 5.10 (d, 6.4) 35, 36
12 67.0, C - - 34 137.4, C - -
13 76.5, C - - 35 18.3, CH3 1.63 (d, 0.8) 33, 34, 36
13-OH - 4.50 (s) 4 36 25.0, CH3 1.64 (s) 33, 34, 35
14 28.38, CH2 1.46 (br m) - 37 32.3, CH2 2.93 (m) 21
1.52 (br s) 3.01 (dd, 16, 8.4)
15 20.3, CH2 1.46 (br m) - 38 63.4, CH 2.93 (m) 20, 21
1.80 (br m) 39 57.9, C - -
16 49.6, CH 2.71 (br m) - 40 18.7, CH3 1.32 (s) 38, 39, 41
17 28.58, CH2 2.45 (br s) 2, 3, 18 41 24.6, CH3 1.23 (s) 38, 39, 40
2.71 (br m)
Terpendole P (3) b
Position δCc, type δHd (multi, J Hz) HMBC Position δCc, type δHd (multi, J Hz) HMBC
1-NH - 10.81 (s) 2, 18, 19, 24 18 114.7, C - -
2 150.6, C - - 19 124.1, C - -
3 38.3, C - - 20 117.8, CH 7.26 (d, 7.8) 18, 22
3-OH - - - 21 118.4, CH 6.88 (td, 7.8, 1.2) 19, 23
4 48.3, C - - 22 119.5, CH 6.93 (td, 7.8, 1.2) 20, 24
5 27.9, CH2 2.05 (m) 3, 4, 7, 13 23 111.7, CH 7.24 (d, 7.8) 19, 21
24 140.1, C - -
6 28.2, CH2 1.75 (m)2.30 (m) - 25 16.2, CH3 0.99 (s) 2, 3, 4, 16
26 18, CH3 1.12 (s) 3, 4, 5, 13
7 70.6, CH 3.86 (m) 9, 12 27 76.9, C - -
28 21.4, CH3 1.17 (s) 9, 27, 29
9 75.5, CH 3.25 (d, 9.0) 7, 11, 27, 28, 29 29 23.9, CH3 1.16 (s) 9, 27, 28
31 58.1, CH2 3.87 (m) 10, 27, 34
10 65.5, CH 3.89 (m) - 3.91 (m)
10-OH - 4.78 (d, 4.2) 9, 10, 11 33 122.1, CH 5.18 (dd, 7.0, 1.2) 35, 36
11 63.1, CH 3.32 (s) 9, 10, 12 34 134.5, C - -
12 62.9, C - - 35 17.7, CH3 1.58 (s) 34, 36
13 66.9, C - - 36 25.3, CH3 1.65 (s) 33, 34, 35
14 54.7, CH 3.19 (d, 5.4) 12, 13
15 24.5, CH2 2.02 (m) 13, 17
1.85 (m)
16 45, CH 2.63 (m) 2, 3, 4, 18
17 26.7, CH2 2.17 (m) 2, 3, 15, 18
2.62 (m)

a 13C (100 MHz) and 1H (400 MHz) spectra were taken on an NMR 400 MHz spectrometer (Agilent). b13C (150 MHz) and 1H (600 MHz) spectra were taken on an NMR 600 MHz spectrometer (Bruker). Chemical shifts are shown with reference to c DMSO-d6 as δ 39.5, d DMSO- d6 as δ 2.48. Multiplicity of signals as follows: s = singlet, d = doublets, dd = double doublets, t = triplet, m = multi. Coupling constants (Hz) were determined by the 1H-1H decoupling experiments.