1. Piper
capense L.f. Piperaceae
New amide alkaloid from the aerial part
of Piper capense L.f. (Piperaceae)
Kaou, A.M., Mahiou-Leddet, V., Canlet, C., Debrauwer, L., Hutter, S., Azas, N., & Ollivier, E.
(2010). New amide alkaloid from the aerial part of Piper capense L.f.
(Piperaceae). Fitoterapia, 81, 632–635.

2. Piper capense
Taxonomy
Kingdom Plantae
Division Magnoliophyta
Class Magnoliopsida
Family Piperaceae
Genus Piper
Species capense
Piper capense Piper nigrum

3. Piper capense

4. Piper capense

5. •
Piper capense
•
•
Plasmodium falciparum

6. •
Piper capense
•
•
Plasmodium falciparum

7. Grille
Grande
Comore

8. P. capense powder 1.1 kg
maceration, CH2Cl2 5 L, rt. 14-15 hr.
Residue CH2Cl2 soluble
Crude CH2Cl2 extract 21.5 g
18.0 g 3.5 g

9. 18.0 g
G1 G2 G3 G4 G5 G6 G7 G8 G9 G10
(225 mg) (220 mg)
G4.1 G4.2 G4.3 G4.4 G6.1 G6.2 G6.3
(95 mg)
Kaousine Apigenine dimethylether
(13 mg) (11 mg)

10. 3.5 g
F1 F2 F3 F4 F5 F6 F7 F8 F9
(26 mg) (2.15 g)
Piperchabamide A
(3.5 mg)
F8.1 F8.2 F8.3 F8.4 F8.5 F8.6 F8.7
Z-antiepilepsirine
(11 mg)

11. •
Piper capense
•
•
Plasmodium falciparum

12. Kaousine
12 5
13 6 4
11
O
14 10 8 3
15 7 N 2
9
O O

13. Kaousine
HREIMS
1H NMR m/z 245.1052
13C NMR
C14H15NO3
UN = C-(H/2)+(N/2)-(X/2)+1
= 14-(15/2)+(1/2)-(0/2)+1
=8

14. Kaousine
HREIMS 7.23, 7.28, 7.19, 7.28, 7.23
1H NMR
13C NMR
(UN = 4)
UN = 8-4
=4

15. Kaousine
HREIMS 169.6
1H NMR 174.7
C C
13C NMR
O O
(UN = 1) (UN = 1)
UN = 4-
(1+1) 2
=2

16. Kaousine
HREIMS
3.56 3.66
1H NMR
13C NMR
C C
O O
C O C
52.3 53.4
ᵟ

17. Kaousine
HREIMS
1H NMR
13C NMR
12 5
13 6 4
11
O
O
14 10 8 3
15 7 N 2
9
O
O O

18. 2D NMR
Kaousine
COSY
HMBC
H H
H
H
12 5
13 H 6 4
11
O
14 10 8 3
15 7 N 2
9
H H H
H
H O O

19. 2D NMR
Kaousine
COSY
HMBC
H H H
12 H H
H 11 H
5
13 6 4
H
O
10 8 3
14 N
9 7 2
H 15
H H H
H H H O O

20. 2D NMR
Kaousine
COSY
HMBC
H H H
12 H H
H 11 H
5
13 6 4
H
O
10 8 3
14 N
9 7 2
H 15
H H H
H H H O O

21. 2D NMR
Kaousine
COSY
HMBC
H H H
12 H H
H 11 H
5
13 6 4
H
O
10 8 3
14 N
9 7 2
H 15
H H H
H H H O O

22. Kaousine
HREIMS COSY
1H NMR HMBC
13C NMR
12 5
13 6 4
11
O
O
14 10 8 3
15 7 N 2
9
O
O O

23. Z-antiepilepsirine
3
O 6 4 2
5
10
9 1
7 8 1’
O
O N 2’
5’ 3’
4’

24. Z-antiepilepsirine
EIMS
1H NMR
m/z 259
13C NMR
C15H17NO3
UN = C-(H/2)+(N/2)-(X/2)+1
= 15-(17/2)+(1/2)-(0/2)+1
=8

25. Z-antiepilepsirine
EIMS
1H NMR 6.92, 6.75, 6.84
13C NMR
(UN = 4)
UN =
8-4
=4

26. Z-antiepilepsirine
EIMS
1H NMR 167.3
13C NMR C
O
(UN = 1)
UN = 4-(1) 2
=3 1

27. Z-antiepilepsirine
EIMS
1H NMR
13C NMR
3
O 6 4 2
5
10
9 1
7 8 1’
O
O
O N 2’
5’ 3’
4’

28. 2D NMR
Z-antiepilepsirine
HMBC
H H
3
H
H O 6 4 2
5
H H
10
9 1 H
H 7 8 1’
O
O N 2’ H
H
5’ 3’
H H
H 4’
H
H
H H

29. 2D NMR
Z-antiepilepsirine
HMBC
H H
3
H
H O 6 4 2
5
H H
10
9 1 H
H 7 8 1’
O
O N 2’ H
H
5’ 3’
H H
H 4’
H
H
H H

30. 2D NMR
Z-antiepilepsirine
HMBC
H H
3
H
H O 6 4 2
5
H H
10
9 1 H
H 7 8 1’
O O N 2’ H
H
5’ 3’
H H
H 4’
H
H
H H

31. Z-antiepilepsirine
EIMS HMBC
1H NMR
13C NMR
3
O 6 4 2
5
10
9 1
7 8 1’
O
O
O N 2’
5’ 3’
4’

32. Z-antiepilepsirine
EIMS HMBC
1H NMR
13C NMR
3
O 6 4 2
5
10
9 1
7 8 1’
O
O N 2’
5’ 3’
4’

33. Z-antiepilepsirine
3
O 6 5 4 2
10
9 1
7 8 1’
O
O N
N
2’
Z-antiepilepsirine
O 5’ 3’
4’
1-[1-oxo-3(3,4-methylenedioxy-5-methoxyphenyl)-2Z-propenyl]piperidine

34. Z-antiepilepsirine
O
O
O N
Z-antiepilepsirine
O
O
N
O
E form

35. Z-antiepilepsirine
O J=12.4 Hz O
J=12.4 Hz
O
O N
O N
Z-antiepilepsirine
O J~15 Hz O
piperine
O
N
J~15 Hz
O
E form

36. •
Piper capense
•
•
Plasmodium falciparum

37. compound Plasmodium falciparum, W2 THP1 cell line
(IC50) (IC50) SI
μg/ml μM μg/ml μM
Kaousine 20 82 34 139 1.7
Z-antiepilepsirine 7 27 >50 >193 >7
Apigenine 12.5 42 17 57 1.4
dimethylether
Chloroquine - 0.7 - 40 57

38. compound Plasmodium falciparum, W2 THP1 cell line
(IC50) (IC50) SI
μg/ml μM μg/ml μM
Kaousine 20 82 34 139 1.7
Z-antiepilepsirine 7 27 >50 >193 >7
Apigenine 12.5 42 17 57 1.4
dimethylether
Chloroquine - 0.7 - 40 57

39. compound Plasmodium falciparum, W2 THP1 cell line
(IC50) (IC50) SI
μg/ml μM μg/ml μM
Kaousine 20 82 34 139 1.7
Z-antiepilepsirine 7 27 >50 >193 >7
Apigenine 12.5 42 17 57 1.4
dimethylether
Chloroquine - 0.7 - 40 57

40. compound Plasmodium falciparum, W2 THP1 cell line
(IC50) (IC50) SI
μg/ml μM μg/ml μM
Kaousine 20 82 34 139 1.7
Z-antiepilepsirine 7 27 >50 >193 >7
Apigenine 12.5 42 17 57 1.4
dimethylether
Chloroquine - 0.7 - 40 57

41. compound Plasmodium falciparum, W2 THP1 cell line
(IC50) (IC50) SI
μg/ml μM μg/ml μM
Kaousine 20 82 34 139 1.7
Z-antiepilepsirine 7 27 >50 >193 >7
Apigenine 12.5 42 17 57 1.4
dimethylether
Chloroquine - 0.7 - 40 57

42. compound Plasmodium falciparum, W2 THP1 cell line
(IC50) (IC50) SI
μg/ml μM μg/ml μM
Kaousine 20 82 34 139 1.7
Z-antiepilepsirine 7 27 >50 >193 >7
Apigenine 12.5 42 17 57 1.4
dimethylether
Chloroquine - 0.7 - 40 57

43. compound Plasmodium falciparum, W2 THP1 cell line
(IC50) (IC50) SI
μg/ml μM μg/ml μM
Kaousine 20 82 34 139 1.7
Z-antiepilepsirine 7 27 >50 >193 >7
Apigenine 12.5 42 17 57 1.4
dimethylether
Chloroquine - 0.7 - 40 57

44. •
Piper capense
4 Kaousine Z-
antiepilepsirine
apigenine dimethylether piperchabamide A

45. •
O
O
N O
O N
O O
Kaousine Z-antiepilepsirine

46. •
Plasmodium falciparum
Kaousine Apigenine
(IC50=20 12.5 μg/ml)
Z-antiepilepsirine
(IC50=7 μg/ml)
Piperchabamide A