Lipid Peroxidation and Cyclooxygenase Enzyme Inhibitory Compounds

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1 Lipid Peroxidation and Cyclooxygenase Enzyme Inhibitory Compounds from Prangos haussknechtii Amila A. Dissanayake, Baram A. H. Ameen, and Muraleedharan G. Nair,* Bioactive Natural Products and Phytoceuticals Laboratory, Department of Horticulture, Michigan State University, East Lansing, 48824, MI, USA Department of Science, Charmo University, Chamchamal-Sualimani, Kurdistan Region, Iraq Supplemental data For compound 1 Figure S1. 1 H NMR spectrum of 1 in CDCl3 3 Figure S2. 13 C NMR spectrum of 1 in CDCl3 4 Figure S3. HSQC spectrum of 1 in CDCl3...5 Figure S4. HMBC spectrum of 1 in CDCl3.6 Figure S5. 1 H 1 H COSY spectrum of 1 in CDCl3 7 Figure S6. NOESY spectrum of 1 in CDCl3 (δh = 4.85) 8 Figure S7. HR-ESITOFMS (positive) of 1.9 Figure S8. Elemental composition of 1 calculated by single mass analysis.. 10 Figure S9. IR spectrum of 1 in KBr..11 Figure S10. UV/Vis spectrum of 1 in methanol..12 For compound 2 Figure S11. 1 H NMR spectrum of 2 in CDCl3..13 Figure S C NMR spectrum of 2 in CDCl3..14 Figure S13. HMBC spectrum of 2 in CDCl Figure S14. NOESY spectrum of 2 in CDCl3 (δh = 4.84) 16 Figure S15. HR-ESITOFMS (positive) of 2 17 Figure S16. Elemental composition of 2 calculated by single mass analysis 18 Figure S17. IR spectrum of 2 in KBr 19 Figure S18. UV/Vis spectrum of 2 in methanol..20 For compound 3 Figure S19. 1 H NMR spectrum of 3 in CDCl3..21 Figure S C NMR spectrum of 3 in CDCl3..22 Figure S21. DEPT spectrum of 3 in CDCl Figure S22. HSQC spectrum of 3 in CDCl3 24 Figure S23. HMBC spectrum of 3 in CDCl3..25 Figure S24. 1 H 1 H COSY spectrum of 3 in CDCl3 26 Figure S25. NOESY spectrum of 3 in CDCl3.27 Figure S26. HR-ESITOFMS (negative) of 3.28 Figure S27. Elemental composition of 3 calculated by single mass analysis 29 Figure S28. IR spectrum of 3 in KBr 30 Figure S29. UV/Vis spectrum of 3 in methanol 31

2 For compound 4 Figure S30. 1 H NMR spectrum of 4 in D2O.32 Figure S C NMR spectrum of 4 in D2O 33 Figure S32. DEPT spectrum of 4 in D2O..34 Figure S33. HSQC spectrum of 4 in D2O..35 Figure S34. HR-ESITOFMS (positive) of 4 36 Figure S35. Elemental composition of 4 calculated by single mass analysis 37 Figure S36. IR spectrum of 4 in KBr 38 Figure S37. UV/Vis spectrum of 4 water..39 Figure S38. HOMODEC NMR spectrum of 4 D2O (δh = 3.71).40 Figure S39. HOMODEC NMR spectrum of 4 D2O (δh = 1.67).41 Figure S40. HOMODEC NMR spectrum of 4 D2O (δh = 3.64).42 Figure S41. HOMODEC NMR spectrum of 4 D2O (δh = 1.94).43 Figure S42. HOMODEC NMR spectrum of 4 D2O (δh = 1.45).44 Figure S43. HOMODEC NMR spectrum of 4 D2O (δh = 0.97).45 Figure S44. HMBC spectrum of 4 in D2O..46 Figure S45. 1 H 1 H COSY spectrum of 4 in D2O 47 Figure S46. NOESY spectrum of 4 in D2O..48 Bio assay results Table 1. MTT, LPO and COX assay results for compounds 1-4 isolated from P. haussknechtii.49 For known compounds Figure S47. Chemical structures of known compounds isolated from P. haussknechtii.50 Figure S48. 1 H NMR spectrum of isoimperatorin in CDCl3 51 Figure S C NMR spectrum of isoimperatorin in CDCl3.52 Figure S50. HSQC spectrum of isoimperatorin in CDCl3.53 Figure S51. 1 H NMR spectrum of osthol in CDCl3 54 Figure S C NMR spectrum of osthol in CDCl3.55 Figure S53. 1 H NMR spectrum of oxypeucedanin in CDCl3.56 Figure S C NMR spectrum of oxypeucedanin in CDCl3.57 Figure S55. 1 H NMR spectrum of malic acid in D2O..58 Figure S C NMR spectrum of malic acid in D2O 59 Figure S57. 1 H NMR spectrum of p-coumaric acid in CD3OD.60 Figure S C NMR spectrum of p-coumaric acid in CD3OD 61 Figure S59. 1 H NMR spectrum of 3-phenyllactic acid in D2O.62 Figure S C NMR spectrum of 3-phenyllactic acid in D2O 63 Figure S61. DEPT spectrum of 3-phenyllactic acid in D2O 64 Figure S62. HMBC spectrum of 3-phenyllactic acid in D2O.65 Figure S63. 1 H NMR spectrum of ferulic acid in CD3OD 66 Figure S C NMR spectrum of ferulic acid in CD3OD.67 Figure S65. DEPT spectrum of ferulic acid in CD3OD.68 Bio assay results Table 2. LPO and COX assay results for known compounds isolated from P. haussknechtii.69

3 Figure S1. 1 H NMR spectrum of 1 in CDCl 3 CDCl 3

4 Figure S2. 13 C NMR spectrum of 1 in CDCl 3 CDCl 3

5 Figure S3. HSQC spectrum of 1 in CDCl 3 CDCl 3 CDCl 3

6 Figure S4. HMBC spectrum of 1 in CDCl 3 CDCl 3 CDCl 3

7 Figure S5. 1 H 1 H COSY spectrum of 1 in CDCl 3 CDCl 3 CDCl 3

8 Figure S6. NOESY spectrum of 1 in CDCl 3 (δh = 4.85)

9 Figure S7. HR-ESITOFMS (positive) of 1

10 Figure S8. Elemental composition of 1 calculated by single mass analysis

11 Figure S9. IR spectrum of 1 in KBr

12 Figure S10. UV/Vis spectrum of 1 in methanol

13 Figure S11. 1 H NMR spectrum of 2 in CDCl 3 CDCl 3

14 Figure S C NMR spectrum of 2 in CDCl 3 CDCl 3

15 Figure S13. HMBC spectrum of 2 in CDCl 3 CDCl 3 CDCl 3

16 Figure S14. NOESY spectrum of 2 in CDCl 3 (δh = 4.84)

17 Figure S15. HR-ESITOFMS (positive) of 2

18 Figure S16. Elemental composition of 2 calculated by single mass analysis

19 Figure S17. IR spectrum of 2 in KBr

20 Figure S18. UV/Vis spectrum of 2 in methanol

21 Figure S19. 1 H NMR spectrum of 3 in CDCl 3 CDCl 3

22 Figure S C NMR spectrum of 3 in CDCl 3 CDCl 3

23 Figure S21. DEPT spectrum of 3 in CDCl 3 CDCl 3

24 Figure S22. HSQC spectrum of 3 in CDCl3

25 Figure S23. HMBC spectrum of 3 in CDCl 3 CDCl 3

26 Figure S24. 1 H 1 H COSY spectrum of 3 in CDCl 3 CDCl 3 CDCl 3

27 Figure S25. NOESY spectrum of 3 in CDCl3

28 Figure S26. HR-ESITOFMS (positive) of 3

29 Figure S27. Elemental composition of 3 calculated by single mass analysis

30 Figure S28. IR spectrum of 3 in KBr

31 Figure S29. UV/Vis spectrum of 3 in methanol

32 Figure S30. 1H NMR spectrum of 4 in D 2 O

33 Figure S C NMR spectrum of 4 in D 2 O

34 Figure S32. DEPT spectrum of 4 in D 2 O

35 Figure S33. HSQC spectrum of 4 in D 2 O

36 Figure S34. HR-ESITOFMS (positive) of 4

37 Figure S35. Elemental composition of 4 calculated by single mass analysis

38 Figure S36. IR spectrum of 4 in KBr

39 Figure S37. UV/Vis spectrum of 4 water

40 Figure S38. HOMODEC NMR spectrum of 4 D 2 O (δh = 3.71)

41 Figure S39. HOMODEC NMR spectrum of 4 D 2 O (δh = 1.67)

42 Figure S40. HOMODEC NMR spectrum of 4 D 2 O (δh = 3.64)

43 Figure S41. HOMODEC NMR spectrum of 4 D 2 O (δh = 1.94)

44 Figure S42. HOMODEC NMR spectrum of 4 D 2 O (δh = 1.45)

45 Figure S43. HOMODEC NMR spectrum of 4 D 2 O (δh = 0.97)

46 Figure S44. HMBC spectrum of 4 in D 2 O

47 Figure S45. 1 H 1 H COSY spectrum of 4 in D 2 O

48 Figure S46. NOESY spectrum of 4 in D 2 O

49 Table 1. MTT, LPO and COX assay results for compounds 1-4 isolated from P. haussknechtii Concentration MTT a,b LPO a,c COX-1 a,d COX-2 a,d (absorbance) (fluorescence) (Inhibition %) (Inhibition %) µm ± 0.02 ND e ND e ND e 73.1 µm ± ± ± ± µm ± ± ± ± µm ± ± ± ± µm ND e 15.9 ± ± ± µm ± ± 2.4 ND e ND e 72.6 µm ± ± ± ± µm ± ± ± ± µm ± ± ± ± µm ND e ND e 21.1 ± ± µm ND e 60.3 ± 2.2 ND e ND e 89.3 µm ± ± ± ± µm ± ± 1.4 ND e ND e 22.3 µm ± ± 0.8 ND e ND e 11.1 µm ± 0.01 ND e ND e ND e µm ND e ND e ND e ND e 69.8 µm ± ± ± ± µm ± ± ± ± µm ± ± ± ± µm ± ± ± ± 1.5 a Values are expressed as mean ± SEM (n = 2). b Positive controls vitamin C and TBHQ gave absorbance values of 0.49 and 0.50 at and µm, respectively. c Commercial antioxidants BHT, BHA and TBHQ with IC 50 values of 10 µm, 6.9 µm and 5 µm, respectively. d The standards aspirin, ibuprofen and naproxen with IC 50 values of 600 µm, 72.8 µm and 52.2 µm, respectively for the inhibition of COX-1 enzyme activity and Celebrex and naproxen with IC 50 values of 1.3 µm and 52.2 µm, respectively for the inhibition of COX-2 enzyme activity. e Data not available.

50 Figure S47. Chemical structures of known compounds H 3 C CH 3 O O O O O O H 3 C O O O O O CH 3 H 3 C CH 3 CH 3 Osthol Isoimperatorin Oxypeucedanin HO O OH HO O OH H 3 C HO O O OH HO O OH O OH p-coumaric acid 3-phenyllacetic acid ferulic acid malic acid

51 Figure S48. 1 H NMR spectrum of isoimperatorin in CDCl 3 CDCl3

52 Figure S C NMR spectrum of isoimperatorin in CDCl 3 CDCl 3

53 Figure S50. HSQC spectrum of isoimperatorin in CDCl 3 CDCl 3 CDCl 3

54 Figure S51. 1 H NMR spectrum of osthol in CDCl 3 CDCl 3

55 Figure S C NMR spectrum of osthol in CDCl 3 CDCl 3

56 Figure S53. 1H NMR spectrum of oxypeucedanin in CDCl 3 CDCl 3

57 Figure S C NMR spectrum of oxypeucedanin in CDCl 3 CDCl 3

58 Figure S55. 1 H NMR spectrum of malic acid in CD 3 OD D 2 O

59 Figure S C NMR spectrum of malic acid in CD 3 OD

60 Figure S57. 1 H NMR spectrum of p-coumaric acid in CD 3 OD CD 3 OD

61 Figure S C NMR spectrum of p-coumaric acid in CD 3 OD CD 3 OD

62 Figure S59. 1 H NMR spectrum of 3-phenyllactic acid in D 2 O D 2 O

63 Figure S60. 13C NMR spectrum of 3-phenyllactic acid in D 2 O

64 Figure S61. DEPT spectrum of 3-phenyllactic acid in D 2 O

65 Figure S62. HMBC spectrum of 3-phenyllactic acid in D 2 O D 2 O

66 Figure S63. 1H NMR spectrum of ferulic acid in CD 3 OD CD 3 OH

67 Figure S C NMR spectrum of ferulic acid in CD 3 OD CD 3 OD

68 Figure S65. DEPT spectrum of ferulic acid in CD 3 OD CD 3 OD

69 Table 2. LPO and COX assay results for known compounds isolated from P. haussknechtii LPO Compound Concentration a,b COX-1 a,c COX-2 a,c (fluorescence) (Inhibition %) (Inhibition %) isoimperatorin 92.6 µm 65.5 ± ± ± 1.8 osthol µm 56.0 ± ± ± µm ND d 46.7 ± ± µm ND d 35.8 ± ± µm ND d 19.6 ± ± 0.2 oxypeucedanin 87.4 µm 38.5 ± ± ± 1.8 malic acid µm 73.0 ± ± ± 1.8 a Values are expressed as mean ± SEM (n = 2). b Commercial antioxidants BHT, BHA and TBHQ with IC 50 values of 10 µm, 6.9 µm and 5 µm, respectively. c The standards aspirin, ibuprofen and naproxen with IC 50 values of 600 µm, 72.8 µm and 52.2 µm, respectively for the inhibition of COX-1 enzyme activity and Celebrex and naproxen with IC 50 values of 1.3 µm and 52.2 µm, respectively for the inhibition of COX-2 enzyme activity.

Supporting information

Supporting information Antimicrobial Metabolites from Streptomyces sp. SN0280 Hui Tian, Jamil Shafi, Mingshan Ji,, Yuhui Bi, and Zhiguo Yu *,, College of Plant Protection, Shenyang Agricultural University,