Table 1 1H (800 MHz) and 13C NMR (200 MHz) spectroscopic data for compounds 1–4 in CDCl3 (δ in ppm, J in Hz).

From: Discovery from Hypericum elatoides and synthesis of hyperelanitriles as α-aminopropionitrile-containing polycyclic polyprenylated acylphloroglucinols

No.

1

2

3

4

δH

δC

δH

δC

δH

δC

δH

δC

1

 

69.4, C

 

70.0, C

 

69.3, C

 

70.1, C

2

 

194.3, C

 

199.8, C

 

194.1, C

 

200.3, C

3

 

112.7, C

 

112.6, C

 

112.0, C

 

113.0, C

4

 

199.8, C

 

193.8, C

 

199.5, C

 

193.8, C

5

 

59.4, C

 

59.8, C

 

59.4, C

 

59.9, C

6a

2.22, br d (14.3)

41.4, CH2

2.07, dd (14.3, 1.6)

41.7, CH2

2.25, br d (14.2)

41.3, CH2

2.06, dd (14.2, 1.8)

41.8, CH2

6b

1.93, dd (14.3, 7.1)

 

1.80, dd (14.3, 6.8)

 

1.92, dd (14.2, 7.2)

 

1.81, dd (14.2, 6.6)

 

7

1.71, m

39.7, CH

1.71, m

40.0, CH

1.72, m

39.6, CH

1.72, m

40.1, CH

8

 

51.3, C

 

51.4, C

 

51.3, C

 

51.4, C

9

 

210.2, C

 

210.8, C

 

210.6, C

 

210.5, C

10a

2.46, dd (13.5, 5.4)

26.2, CH2

2.66, dd (13.5, 8.5)

26.3, CH2

2.46, dd (13.5, 5.2)

26.2, CH2

2.68, dd (13.4, 8.3)

26.4, CH2

10b

2.40, dd (13.5, 8.5)

 

2.64, dd (13.5, 5.8)

 

2.42, dd (13.5, 8.5)

 

2.64, dd (13.4, 5.0)

 

11

4.81, t (6.2)

120.0, CH

4.81, t (6.2)

120.3, CH

4.84, t (6.8)

120.3, CH

4.87, t (6.3)

119.5, CH

12

 

133.6, C

 

133.4, C

 

133.4, C

 

134.4, C

13

1.66, s

26.1, CH3

1.57, s

26.1, CH3

1.67, s

26.1, CH3

1.65, s

25.9, CH3

14

1.40, s

17.8, CH3

1.70, s

18.2, CH3

1.43, s

17.9, CH3

1.73, s

18.2, CH3

15

 

170.0, C

 

169.2, C

 

170.2, C

 

169.1, C

16

 

132.3, C

 

132.5, C

 

132.5, C

 

132.4, C

17

6.99, d (7.6)

125.8, CH

7.40, d (7.6)

126.8, CH

6.85, d (7.6)

125.5, CH

7.14, d (7.6)

125.8, CH

18

7.44, t (7.6)

129.3, CH

7.57, t (7.6)

129.3, CH

7.38, t (7.6)

128.9, CH

7.51, overlap

128.8, CH

19

7.50, t (7.6)

129.7, CH

7.51, t (7.6)

130.5, CH

7.51, t (7.6)

129.9, CH

7.50, overlap

130.2, CH

20

7.54, t (7.6)

128.8, CH

7.40, t (7.6)

129.4, CH

7.60, t (7.6)

129.2, CH

7.46, t (7.6)

129.8, CH

21

7.19, d (7.6)

126.1, CH

6.88, d (7.6)

126.4, CH

7.45, d (7.6)

127.0, CH

7.03, d (7.6)

126.5, CH

22

4.16, dq (8.7, 7.1)

40.1, CH

4.11, dq (9.0, 7.0)

41.1, CH

4.04, dq (8.8, 7.1)

41.0, CH

4.19, dq (8.8, 7.3)

40.2, CH

23

 

117.4, C

 

117.9, C

 

117.8, C

 

117.3, C

24

1.63, d (7.1)

19.9, CH3

1.48, d (7.0)

20.6, CH3

1.54, d (7.1)

20.4, CH3

1.68, d (7.3)

20.0, CH3

25

1.35, s

18.5, CH3

1.08, s

18.1, CH3

1.32, s

18.5, CH3

1.08, s

18.0, CH3

26a

2.18, m

28.7, CH2

2.12, m

28.9, CH2

2.23, m

28.7, CH2

2.11, m

28.9, CH2

26b

1.98, m

 

2.03, m

 

1.97, m

 

2.01, m

 

27

4.90, t (6.9)

124.9, CH

4.88, t (6.8)

124.1, CH

4.88, t (6.9)

124.5, CH

4.90, t (6.8)

124.3, CH

28

 

132.3, C

 

132.8, C

 

132.8, C

 

132.6, C

29

1.70, s

25.8, CH3

1.64, s

25.7, CH3

1.71, s

25.8, CH3

1.65, s

25.7, CH3

30

1.51, s

17.7, CH3

1.51, s

17.9, CH3

1.58, s

17.8, CH3

1.49, s

17.9, CH3

31a

1.32, m

35.8, CH2

1.41, m

36.1, CH2

1.32, m

35.9, CH2

1.41, m

36.1, CH2

31b

1.15, m

 

1.21, m

 

1.14, m

 

1.21, m

 

32a

1.82, m

22.4, CH2

1.89, m

22.6, CH2

1.83, m

22.4, CH2

1.89, m

22.6, CH2

32b

1.77, m

 

1.82, m

 

1.78, m

 

1.83, m

 

33

5.01, t (7.0)

123.9, CH

5.03, t (7.0)

123.9, CH

5.00, t (7.0)

123.9, CH

5.03, t (7.0)

123.9, CH

34

 

131.9, C

 

131.9, C

 

131.8, C

 

131.9, C

35

1.65, s

25.7, CH3

1.66, s

25.7, CH3

1.65, s

25.7, CH3

1.66, s

25.7, CH3

36

1.55, s

17.6, CH3

1.57, s

17.6, CH3

1.55, s

17.6, CH3

1.57, s

17.6, CH3

37

1.10, s

19.1, CH3

1.31, s

19.2, CH3

1.10, s

19.1, CH3

1.30, s

19.2, CH3

–NH

13.33, d (8.7)

 

13.20, d (9.0)

 

13.49, d (8.8)

 

13.06, d (8.8)

 
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