Table 1 1H NMR (600 MHz) and 13C NMR data for compounds 1–4 (δ in ppm, J in Hz).

From: (+)/(−)-Phaeocaulin A-D, four pairs of new enantiomeric germacrane-type sesquiterpenes from Curcuma phaeocaulis as natural nitric oxide inhibitors

Position

1 a

2 a

3 b

4 b

1H

13C c

1H

13C c

1H

13C d

1H

13C d

1

4.92 (dd, 10.6, 3.6)

128.4

4.90 (m)

129.2

5.01 (brs)

128.7

5.27 (d, 7.9)

130.7

2

2.06 (m)

26.9

2.16 (m)

28.4

2.16 (m)

27.0

2.14 (m)

29.3

 

2.20 (ddd, 24.0, 12.0, 3.3)

 

2.16 (m)

 

2.16 (m)

 

2.22 (m)

 

3

2.89 (m)

31.0

3.00 (m)

32.6

3.01 (m)

30.8

2.40 (m)

36.2

 

2.11 (m)

 

2.10 (m)

 

2.14 (m)

 

2.12 (m)

 

4

 

148.7

 

151.4

 

150.6

 

140.3

5

6.37 (s)

130.9

6.30 (s)

130.6

6.17 (brs)

127.7

3.45 (s)

50.7

6

 

195.3

 

196.0

 

191.1

 

197.1

7

 

153.7

 

156.3

 

158.1

 

154.7

8

 

92.8

4.64 (d, 9.8)

60.4

5.24 (brs)

80.1

 

110.4

9

2.24 (d, 12.8)

50.3

2.63 (dd, 11.8, 3.1)

47.3

2.86 (dd, 11.8, 3.7)

45.5

2.32 (d, 13.3)

49.9

 

2.69 (d, 12.8)

 

1.96 (m)

 

2.18 (m)

 

2.86 (d, 13.3)

 

10

 

139.4

 

138.1

 

133.6

 

135.4

11

 

140.3

 

140.9

 

132.9

 

130.5

12

 

172.1

 

175.1

 

172.9

 

170.4

13

1.93 (s)

10.1

1.91 (s)

10.8

2.03 (s)

9.9

2.00 (s)

10.6

14

1.88 (s)

25.2

1.92 (s)

25.9

1.93 (s)

25.0

4.95 (s)

119.2

       

5.12 (s)

 

15

1.66 (s)

18.8

1.61 (s)

17.7

1.60 (s)

16.6

1.64 (s)

17.8

  1. aSpectra were obtained in CD3OD.
  2. bSpectra were obtained in CDCl3.
  3. cRecorded at 75 MHz.
  4. dRecorded at 150 MHz.