Table 1 1H (600 MHz) and 13C (150 MHz) NMR Data for Dysivillosins A–D (1–4) in Pyr-d 5.

From: Dysivillosins A–D, Unusual Anti-allergic Meroterpenoids from the Marine Sponge Dysidea villosa

Position

1

2

3

4

δ C

δ H (J in Hz)

δ C

δ H (J in Hz)

δ C

δ H (J in Hz)

δ C

δ H (J in Hz)

1α

19.5, CH2

2.33, m

22.8, CH2

2.35, m

19.1, CH2

2.39, m

22.5, CH2

2.41, m

1β

 

1.63, m

 

1.55, dd (12.0, 2.4)

 

1.57, m

 

1.53, dd (12.0, 3.6)

2a

26.3, CH2

2.38, m

28.0, CH2

1.93, m

26.1, CH2

2.23, m

27.9, CH2

1.92, m

2b

 

2.14, m

 

1.59, m

 

2.07, m

 

1.35, m

3α

120.4, CH

5.16, brs

32.6, CH2

2.36, m

120.4, CH

4.98, brs

32.5, CH2

2.26, td (15.0, 4.8)

3β

   

2.11, m

   

1.96, m

4

143.6, C

 

159.4, C

 

143.1, C

 

159.0, C

 

5

38.0, C

 

39.9, C

 

37.8, C

 

39.8, C

 

6α

35.6, CH2

0.89, td (13.2, 3.6)

36.4, CH2

1.29, dd (13.2, 3.6)

35.5, CH2

0.75, td (13.2, 3.6)

36.3, CH2

1.14, td (13.2, 3.6)

6β

 

1.49, dt (12.6, 3.0)

 

1.45, m

 

1.41, dt (12.6, 3.6)

 

1.35, m

7α

27.4, CH2

1.32, m

27.4, CH2

1.42, m

27.0, CH2

1.20, dd (13.2, 3.6)

27.0, CH2

1.41, m

7β

 

1.37, td (12.6, 1.2)

 

1.39, m

 

1.30, td (13.2, 3.0)

 

1.35, m

8

36.0, CH

1.81, m

36.3, CH

1.76, m

35.9, CH

1.69, m

36.2, CH

1.63, m

9

41.8, C

 

42.2, C

 

41.3, C

 

41.6, C

 

10

45.9, CH

1.55, d (12.0)

48.2, CH

1.36, dd (12.0, 2.4)

45.9, CH

1.39, dd (12.6, 1.2)

48.3, CH

1.20, dd (12.0, 1.8)

11a

17.6, CH3

1.45, br s

102.6, CH2

4.46, s

17.5, CH

1.35, br s

102.6, CH2

4.32, s

11b

   

4.38, s

   

4.28, s

12

19.6, CH3

1.03, s

20.0, CH3

1.06, s

19.5, CH3

0.96, s

20.0, CH3

0.99, s

13

17.3, CH3

1.20, d (6.6)

17.4, CH3

1.20, d (6.6)

16.6, CH3

1.09, d (6.6)

16.8, CH3

1.10, d (6.6)

14

17.4, CH3

0.94, s

17.3, CH3

0.93, s

17.3, CH3

0.87, s

17.2, CH3

0.88, s

15a

37.8, CH2

3.13, s

37.7, CH2

3.09, d (14.4)

37.2, CH2

3.20, d (14.4)

37.3, CH2

3.12, d (14.4)

15b

   

3.04, d (14.4)

 

2.93, d (14.4)

 

2.88, d (14.4)

16

128.4, C

 

128.2, C

 

124.1, C

 

123.9, C

 

17

153.9, C

 

153.8, C

 

147.9, C

 

149.7, C

 

18

106.1, CH

7.74, s

106.1, CH

7.69, s

122.3, C

 

122.4, C

 

19

120.8, C

 

120.8, C

 

105.0, CH

7.68, d (2.4)

105.1, CH

7.63, d (3.0)

20

147.8, C

 

147.8, C

 

154.3, C

 

154.2, C

 

21

114.9, CH

7.59, s

114.6, CH

7.53, s

120.0, CH

7.26, d (2.4)

119.7, CH

7.20, d (3.0)

22

117.0, C

 

117.0, C

 

117.3, C

 

117.2, C

 

23

129.1, CH

8.13, dd (7.8, 1.8)

129.1, CH

8.10, dd (7.8, 1.8)

129.5, CH

8.21, dd (7.2, 1.8)

129.4, CH

8.18, dd (7.8, 1.8)

24

118.4, CH

7.17, dd (7.8, 4.8)

118.4, CH

7.16, dd (7.8, 4.8)

118.6, CH

7.21, dd (7.2, 4.8)

118.5, CH

7.16, dd (7.8, 4.8)

25

145.4, CH

8.46, dd (4.8, 1.8)

145.4, CH

8.45, dd (4.8, 1.8)

145.8, CH

8.52, dd (4.8, 1.8)

145.8, CH

8.50, dd (4.8, 1.8)

27

163.5, C

 

163.5, C

 

163.3, C

 

163.3, C

 

17-OH

 

11.65, br s

 

11.63, br s

 

11.67, br s

 

11.63, br s

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