Natural Nitric Oxide (NO) inhibitors from the rhizomes of Curcuma phaeocaulis. Supplementary Information

Transcription

1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Natural Nitric xide (N) inhibitors from the rhizomes of Curcuma phaeocaulis Supplementary Information Jiang-ao Ma, ab Feng Zhao, c Ying Wang, b Yue Liu, b Su-Yu Gao, b Li-Qin Ding, a Li-Xia Chen,* b and Feng Qiu* a a School of Chinese Materia Medica and Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 30093, People s Republic of China. b Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 006, People s Republic of China c School of Pharmacy, Yantai University, Yantai , People s Republic of China *Corresponding author: Feng Qiu, PD School of Chinese Materia Medica and Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 32 Anshanxi Road, Nankai District, Tianjin 30093, People s Republic of China. Tel: fengqiu200708@63.com Lixia Chen, PD Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University. Tel: syzyclx@63.com

2 Contents of Supporting Information No. Contents: Pages: Figure S-S8 3 C NMR, NMR, - CSY, SQC, MBC, NESY, Rh 2 (CCF 3 ) 4 -induced CD spectra, RESIMS spectra of phasalvione () 3-0 Figure S9-S6 Figure S7-S22 Figure S23-S27 Figure S28-S33 Figure S34-S39 Figure S40-S45 3 C NMR, NMR, - CSY, SQC, MBC, NESY, Rh 2 (CCF 3 ) 4 -induced CD spectra, RESIMS spectra of phaeocaudione (2) 3 C NMR, NMR, SQC, MBC, NESY, RESIMS spectra of phaeocauone (3) 3 C NMR, NMR, SQC, MBC, RESIMS spectra of 3- methyl-4-(3-oxobutyl)-benzoic acid (4) 3 C NMR, NMR, SQC, MBC, NESY, RESIMS spectra of 8β()-elema-,3,7()-trien-8,2-lactam (5) 3 C NMR, NMR, SQC, MBC, NESY, RESIMS spectra of 8β-methoxy-isogermafurenolide (6) 3 C NMR, NMR, SQC, MBC, NESY, CD, RESIMS spectra of phaeusmane I (7) Figure S46-S5 Figure S52-S53 3 C NMR, NMR, SQC, MBC, NESY, RESIMS spectra of phaeoheptanoxide (8) Chiral PLC analytical chromatograms for compounds

3 Figure S. 3 C NMR spectra of phasalvione ()

4 Figure S2. NMR spectra of phasalvione ()

5 Figure S3. - CSY spectra of phasalvione ()

6 Figure S4. SQC spectra of phasalvione ()

7 Figure S5. MBC spectra of phasalvione ()

8 Figure S6. NESY spectra of phasalvione ()

9 Figure S7. Rh 2 (CCF 3 ) 4 -induced CD spectra of phasalvione () 9

10 Figure S8. RESIMS spectra of phasalvione () 0

11 Figure S9. 3 C NMR spectra of phaeocaudione (2)

12 Figure S0. NMR spectra of phaeocaudione (2)

13 Figure S. - CSY spectra of phaeocaudione (2)

14 Figure S2. SQC spectra of phaeocaudione (2)

15 Figure S3. MBC spectra of phaeocaudione (2)

16 Figure S4. NESY spectra of phaeocaudione (2)

17 Figure S5. Rh 2 (CCF 3 ) 4 -induced CD spectra of phaeocaudione (2) 7

18 Figure S6. RESIMS spectra of phaeocaudione (2) 8

19 Figure S7. 3 C NMR spectra of phaeocauone (3)

20 Figure S8. NMR spectra of phaeocauone (3)

21 Figure S9.SQC spectra of phaeocauone (3)

22 Figure S20.MBC spectra of phaeocauone (3)

23 Figure S2. NESY spectra of phaeocauone (3)

24 Figure S22. RESIMS spectra of phaeocauone (3) 24

25 Figure S23. 3 C NMR spectra of 3-methyl-4-(3-oxobutyl)-benzoic acid (4)

26 Figure S24. NMR spectra of 3-methyl-4-(3-oxobutyl)-benzoic acid (4)

27 4 4 Figure S25. SQC spectra of 3-methyl-4-(3-oxobutyl)-benzoic acid (4)

28 Figure S26. MBC spectra of 3-methyl-4-(3-oxobutyl)-benzoic acid (4)

29 Figure S27. RESIMS spectra of 3-methyl-4-(3-oxobutyl)-benzoic acid (4) 29

30 Figure S28. 3 C NMR spectra of 8β()-elema-,3,7()-trien-8,2-lactam (5) N

31 Figure S29. NMR spectra of 8β()-elema-,3,7()-trien-8,2-lactam (5) N

32 Figure S30. SQC spectra of 8β()-elema-,3,7()-trien-8,2-lactam (5) N

33 Figure S3. MBC spectra of 8β()-elema-,3,7()-trien-8,2-lactam (5) N

34 Figure S32. NESY spectra of 8β()-elema-,3,7()-trien-8,2-lactam (5) N

35 Figure S33. RESIMS spectra of 8β()-elema-,3,7()-trien-8,2- lactam (5) 35

36 Figure S34. 3 C NMR spectra of 8β-methoxy-isogermafurenolide (6) C

37 Figure S35. NMR spectra of 8β-methoxy-isogermafurenolide (6) C

38 Figure S36. SQC spectra of 8β-methoxy-isogermafurenolide (6) C

39 Figure S37. MBC spectra of 8β-methoxy-isogermafurenolide (6) C

40 Figure S38. NESY spectra of 8β-methoxy-isogermafurenolide (6) C

41 Figure S39. RESIMS spectra of 8β-methoxy-isogermafurenolide (6) 4

42 Figure S40. 3 C NMR spectra of phaeusmane I (7) N 7 42

43 Figure S4. NMR spectra of phaeusmane I (7) N 7 43

44 Figure S42. SQC spectra of phaeusmane I (7) N 7 44

45 Figure S43. MBC spectra of phaeusmane I (7) N 7 45

46 Figure S44. NESY spectra of phaeusmane I (7) N 7 46

47 Figure S45. RESIMS spectra of phaeusmane I (7) 47

48 Figure S46. 3 C NMR spectra of phaeoheptanoxide (8)

49 Figure S47. NMR spectra of phaeoheptanoxide (8)

50 Figure S48. SQC spectra of phaeoheptanoxide (8)

51 Figure S49. MBC spectra of phaeoheptanoxide (8)

52 Figure S50. NESY spectra of phaeoheptanoxide (8)

53 Figure S5. RESIMS spectra of phaeoheptanoxide (8) 53

54 Figure S52. Chiral PLC analytical chromatograms for compounds 5 and 6 Figure S53. Chiral PLC analytical chromatogram for compound 7 54