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Table 1 13 C NMR (150 MHz) and 1 H NMR spectroscopic data (600 MHz) of 14 in CDCl3

From: Azaphilones produced by Penicillium maximae with their cell death-inducing activity on Adriamycin-treated cancer cell

Position

1

 

Position

2

 

3

 

4

 
 

δC

δH (J in Hz)

 

δC

δH (J in Hz)

δC

δH (J in Hz)

δC

δH (J in Hz)

1

63.7

4.88 (d, J = 13.2)

4.99 (d, J = 13.2)

1

63.9

4.80 (d, J = 12.6)

5.06 (d, J = 12.6)

63.9

a 4.86 (d, J = 13.2)

b 5.04 (d, J = 13.2)

68.2

a 4.49 (dd, J = 4.8, 11.4)

b 4.22 (m)

3

162.7

 

3

161.9

 

161.9

 

161.0

 

4

104.3

5.31 (s)

4

105.0

5.37 (s)

104.4

5.33 (s)

104.8

5.70 (s)

5

149.0

 

5

149.0

 

147.8

 

151.6

 

6

26.4

a 2.88 (dd, J = 6.6, 19.2)

b 2.43 (overlapped)

6

32.5

a 2.75 (m)

b 2.69 (m)

32.0

a 2.84 (d-like, J = 19.2)

b 2.63 (d-like, J = 19.2)

113.2

5.78 (s)

7

42.1

3.26 (dd, J = 4.8, 12.6)

7

73.0

4.16 (m)

74.9

5.33 (overlapped)

199.4

 

8

82.7

 

8

75.6

 

74.0

 

76.4

 

9

188.5

 

9

195.9

 

195.2

 

74.5

4.14 (d, J = 2.4)

10

114.6

 

10

112.2

 

112.8

 

36.6

3.00 (m)

11

117.6

5.86 (d, J = 15.6)

11

118.1

5.89 (d, J = 15.0)

117.9

5.89 (d, J = 15.6)

118.9

5.89 (d, J = 16.2)

12

142.6

6.96 (d, J = 15.6)

12

141.1

6.93 (d, J = 15.0)

141.3

6.95 (d, J = 15.6)

140.6

6.92 (d, J = 16.2)

13

132.1

 

13

132.1

 

132.1

 

132.1

 

14

147.6

5.61 (d, J = 9.6)

14

146.6

5.58 (d, J = 9.6)

146.7

5.59 (d, J = 10.2)

146.1

5.57 (d, J = 9.6)

15

35.0

2.43 (overlapped)

15

34.9

2.44 (m)

35.0

2.44 (m)

34.9

2.44 (m)

16

30.1

1.28 (m)

1.40 (m)

16

30.1

1.29 (m)

1.40 (m)

30.1

1.29 (m)

1.39 (m)

30.2

1.30 (m)

1.41 (m)

17

11.9

0.83 (t, J = 7.8)

17

11.9

0.83 (t, J = 7.8)

11.9

0.84 (t, J = 7.2)

11.9

0.85 (t, J = 7.2)

18

20.3

0.97 (d, J = 7.8)

18

20.3

0.98 (d, J = 6.0)

20.3

0.98 (d, J = 6.6)

20.4

0.98 (d, J = 6.0)

19

12.4

1.77 (s)

19

12.4

1.79 (s)

12.4

1.79 (s)

12.4

1.79 (s)

20

21.7

1.62 (s)

20

23.5

1.33 (s)

24.2

1.39 (s)

23.3

1.36 (s)

21

169.3

 

COCH3

  

170.6

   

22

56.6

3.59 (d, J = 12.6)

COCH 3

  

21.1

2.02 (s)

  

23

200.3

        

24

30.0

2.46 (s)