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. 2014 Dec 29;13(1):102–127. doi: 10.3390/md13010102

Table 4.

1H and 13C NMR data (500 MHz, CDCl3) data for paradoxquinol (10) and paradoxquinone (15).

Paradoxquinol (10) Paradoxquinone (15)
Position δC a, Type δH (J in Hz) gCOSY gHMBCAD δC a, type δH (J in Hz) gCOSY gHMBCAD
1 187.7, C 188.0, C
2 148.1, C 148.5, C
3 132.1, CH 6.46, s 1′ 132.3, CH 6.46, bs 5, 1′ 1, 4, 5
4 187.9, C 188.0, C
5 140.6, C * 133.2, CH 6.54, bs 3, 7 1, 3, 4
6 141.5, C * 145.9, C
7 12.4, CH3 2.03, s 1, 5, 6 16.0, CH3 2.05, s 5 1, 5, 6
8 12.1, CH3 2.00, s 4, 5, 6 3, 2′, 18′ 1, 2, 3, 2′, 3′
1′ 27.4, CH2 3.12, d (7.0) 3, 2′, 18′ 1, 2, 3, 2′, 3′ 27.5, CH2 3.13, d (7.5) 1′, 18 1′, 4′, 18′
2′ 118.2, CH 5.15, t (7.0) 1′, 18′ 4′ 118.1, CH 5.15, t (7.5)
3′ 139.5, C 139.8, C 2′, 3′, 5′, 18′
4′ 39.5, CH2 2.06, m 2′, 5′, 6′, 18′ 39.6, CH2 2.07, m 6′, 18′w, 19′w 3′, 4′, 6′, 7′
5′ 26.3, CH2 2.12, m 6′ 4′, 6′ 26.2, CH2 2.11, m 5′ 4′, 5′, 19′
6′ 124.4, CH 5.11, m 5′, 19′ 4′, 8′ 124.2, CH 5.10, m
7′ 134.7, C 135.1, C 6′, 7′, 10′
8′ 39.5, CH2 2.06, m 19′ 39.3, CH2 2.02, m 10′, 20′w 7′, 10′, 11′
9′ 26.0, CH2 2.21, m 10′ 26.2, CH2 2.11, m 9′, 20′ 9′, 12′, 20′
10′ 130.5, CH 5.53, t (7.0) 9′ 12′, 20′ 126.1, CH 5.38, t (7.0)
11′ 138.9, C 136.7, C 13a′ 10′, 11′, 13′, 14′, 20′
12′ 76.9, CH 4.16, dd (5.5, 7.5) 13a′, 13b′ 10′ 77.2, CH 3.97, dd (5.5, 7.5) 12′, 17′
13a′ 35.1, CH2 2.26, m 12′, 14′ 34.2, CH2 2.20, m 12′, 17′ 11′, 12′, 14′, 15′
13b′ 2.43, ddd (7.5, 8.5, 14.5) 12′, 13a′, 14′ 12′, 14′ 2.27, m 17′
14′ 119.9, CH 5.11, m 16′, 17′ 120.3, CH 5.09, m
15′ 135.4, C 134.6, C 14′, 15′
16′ 18.1, CH3 1.65, s 13a′, 13b′ 14′, 15′, 17′ 18.0, CH3 1.63, s 14′, 15′, 16′
17′ 25.9, CH3 1.73, s 13a′, 13b′, 14′ 14′, 15′, 16′ 25.9, CH3 1.72, s 2′, 3′
18′ 16.1, CH3 1.62, s 1′, 2′ 2′, 3′, 4′ 16.1, CH3 1.61, s 7′
19′ 16.1, CH3 1.60, s 5′, 6′ 6′, 7′, 8′ 16.1, CH3 1.61, s 10′, 11′
20′ 58.5, CH2 4.26, d (3.5) 10′, 11′. 12′ 11.7, CH3 1.61, s
12′-OH ND b ND b
20′-OH ND b

a Carbon NMR assignments made on the basis of gHSQCAD and gHMBCAD NMR experiments. b Signal not detected. * Indicates signals interchangeable