Gade Hyldgaard, Mette; Purup, Stig; Bond, Andrew David; Frete, Xavier; Qu, Haiyan; Teglgaard Jensen, Katrine; Christensen, Lars Porskjær
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1 Syddansk Universitet Guaianolides and a seco-eudesmane from the resinous exudates of cushion bush (Leucophyta brownii) and evaluation of their cytostatic and anti-inflammatory activity Gade Hyldgaard, Mette; Purup, Stig; Bond, Andrew David; Frete, Xavier; Qu, Haiyan; Teglgaard Jensen, Katrine; Christensen, Lars Porskjær Published in: Journal of Natural Products DOI: /acs.jnatprod.5b00208 Publication date: 2015 Document version Publisher's PDF, also known as Version of record Citation for pulished version (APA): Gade Hyldgaard, M., Purup, S., Bond, A. D., Fretté, X., Qu, H., Teglgaard Jensen, K., & Christensen, L. P. (2015). Guaianolides and a seco-eudesmane from the resinous exudates of cushion bush (Leucophyta brownii) and evaluation of their cytostatic and anti-inflammatory activity. Journal of Natural Products, 78(8), General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. Users may download and print one copy of any publication from the public portal for the purpose of private study or research. You may not further distribute the material or use it for any profit-making activity or commercial gain You may freely distribute the URL identifying the publication in the public portal? Take down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Download date: 04. jan
2 Supporting Information Guaianolides and a seco-eudesmane from the Resinous Exudates of Cushion Bush (Leucophyta brownii) and Evaluation of Their Cytostatic and Anti-inflammatory Activity Mette G. Hyldgaard, Stig Purup, Andrew D. Bond, Xavier C. Fretté, Haiyan Qu, Katrine T. Jensen, and Lars P. Christensen*, Department of Chemical Engineering, Biotechnology and Environmental Technology, University of Southern Denmark, Campusvej 55, 5230 Odense M, Denmark Department of Animal Science, Aarhus University, Blichers Allé 20, 8830 Tjele, Denmark Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom Corresponding Author * Tel.: Fax: lpc@kbm.sdu.dk Supporting Information Contents Supporting information contains an analytical HPLC chromatogram of the dichloromethane extract of fresh aerial parts of Leucophyta brownii at 210 nm showing the separation and t R of the isolated compounds 1 10, 1 H, 13 C, DEPT, and 2D NMR ( 1 H 1 H COSY, NOESY, HSQC, and HMBC) spectra of compounds 1 10, crystal structures (ORTEP diagrams) of the sesquiterpene lactones 2 4, 7, and 8 with displacement ellipsoids at 50% probability for non-h atoms, and a description of physical (melting point, optical activity), spectroscopic (UV, IR) and spectrometric (APCIMS, HRESIMS) data of compounds 1 4 and 7 9 (page 5 to 92). 1
3 Supporting Information Contents Page Analytical HPLC chromatogram (Fig. S1) of the CH 2 Cl 2 extract from Leucophyta brownii Hydroxy-5 H,10 H-1,11(13)-guaidien-8,12-olide (1) [ ] 25 D, UV, IR, APCIMS, HRESIMS data of H NMR (400 MHz, CDCl 3 ) spectrum of 1 (Figs. S2 and S3) C NMR (100 MHz, CDCl 3 ) spectrum of 1 (Fig. S4)... 9 DEPT spectrum of 1 (Fig. S5) D NMR spectra (COSY, NOESY, HSQC, HMBC) of 1 (Figs. S6 S9) ,10 -Dihydroxy-5 H-1,11(13)-guaidien-8,12-olide (2) mp, [ ] 25 D, UV, IR, APCIMS, HRESIMS data and crystal structure (Fig. S10) of H NMR (400 MHz, methanol-d 4 ) spectrum of 2 (Fig. S11) C NMR (100 MHz, methanol-d 4 ) spectrum of 2 (Fig. S12) DEPT spectrum of 2 (Fig. S13) D NMR spectra (COSY, NOESY, HSQC, HMBC) of 2 (Figs. S14 S17) Hydroxy-1,2 -epoxy-5 H,10 H-11(13)-guaien-8,12-olide (3) mp, [ ] 25 D, UV, IR, APCIMS, HRESIMS data and crystal structure (Fig. S18) of H NMR (400 MHz, CDCl 3 ) spectrum of 3 (Figs. S19 and S20) C NMR (100 MHz, CDCl 3 ) spectrum of 3 (Fig. S21) DEPT spectrum of 3 (Fig. S22) D NMR spectra (COSY, NOESY, HSQC, HMBC) of 3 (Figs. S23 S26) Calocephalin (4) mp, [ ] 25 D, UV, IR, APCIMS, HRESIMS data and crystal structure (Fig. S27) of H NMR (400 MHz, CDCl 3 ) spectrum of 4 (Figs. S28 and S29) C NMR (100 MHz, CDCl 3 ) spectrum of 4 (Fig. S30) DEPT spectrum of 4 (Fig. S31) D NMR spectra (COSY, NOESY, HSQC, HMBC) of 4 (Figs. S32 S35)
4 Leucophytalin A [4 -acetoxy-1,2 -dihydroxy-5 H,10 H-11(13)-guaien-8,12-olide] (5) 1 H NMR (400 MHz, CDCl 3 ) spectrum of 5 (Figs. S36 S38) C NMR (100 MHz, CDCl 3 ) spectrum of 5 (Fig. S39) DEPT spectrum of 5 (Fig. S40) D NMR spectra (COSY, NOESY, HSQC, HMBC) of 5 (Figs. S41 S44) Leucophytalin B [2 -acetoxy-1,4 -epoxy-5 H,10 H-11(13)-guaien-8,12-olide] (6) 1 H NMR (400 MHz, methanol-d 4 ) spectrum of 6 (Figs. S45 and S46) C NMR (100 MHz, methanol-d 4 ) spectrum of 6 (Fig. S47) DEPT spectrum of 6 (Fig. S48) D NMR spectra (COSY, NOESY, HSQC, HMBC) of 6 (Figs. S49 S52) Pseudoivalin (7) mp, [ ] 25 D, UV, IR, APCIMS, HRESIMS data and crystal structure (Fig. S53) of H NMR (400 MHz, CDCl 3 ) spectrum of 7 (Figs. S54 and S55) C NMR (100 MHz, CDCl 3 ) spectrum of 7 (Fig. S56) DEPT spectrum of 7 (Fig. S57) D NMR spectra (COSY, NOESY, HSQC, HMBC) of 7 (Figs. S58 S61) Pseudoivalin acetate (8) mp, [ ] 25 D, UV, IR, APCIMS, HRESIMS data and crystal structure (Fig. S62) of H NMR (400 MHz, CDCl 3 ) spectrum of 8 (Figs. S63 and S64) C NMR (100 MHz, CDCl 3 ) spectrum of 8 (Fig. S65) DEPT spectrum of 8 (Fig. S66) D NMR spectra (COSY, NOESY, HSQC, HMBC) of 8 (Figs. S67 S70) Tomentosin (9) [ ] 25 D, UV, APCIMS and HRESIMS data of H NMR (400 MHz, CDCl 3 ) spectrum of 9 (Figs. S71 and S72) C NMR (100 MHz, CDCl 3 ) spectrum of 9 (Fig. S73) DEPT spectrum of 9 (Fig. S74) D NMR spectra (COSY, NOESY, HSQC, HMBC) of 9 (Figs. S75 S78)
5 Leucophytalin C [12-hydroxy-7 H-1,10-seco-eudesma-5(10),11(13)-dien-1-oic acid] (10) 1 H NMR (400 MHz, CDCl 3 ) spectrum of 10 (Figs. S79 and S80) C NMR (100 MHz, CDCl 3 ) spectrum of 10 (Fig. S81) DEPT spectrum of 10 (Fig. S82) D NMR spectra (COSY, NOESY, HSQC, HMBC) of 10 (Figs. S83 S86)
6 Fig. S1. Analytical HPLC chromatogram of the dichloromethane extract of fresh aerial parts of Leucophyta brownii at 210 nm (Peak numbers 1 10 in the HPLC chromatogram refer to compound numbers). 5
7 4 -Hydroxy-5 H,10 H-1,11(13)-guaidien-8,12-olide (1) Colorless resin-like oil; [ ] 25 D +153 (c 0.4, MeOH); UV (MeOH) max (log ) 205 (3.66) nm; IR (KBr) max 3338, 2926, 1771, 1660, 1110 cm -1 APCIMS: m/z 249 [M + H] + (14), 231 [M + H H 2 O] + (100); HRESIMS m/z (calcd for C 15 H 21 O 3, ). 6
8 1 H NMR 1 Fig. S2. 1 H NMR (400 MHz, CDCl 3 ) spectrum of compound 1. 7
9 1 H NMR 1 Fig. S3. 1 H NMR (400 MHz, CDCl 3 ) spectrum of compound 1 expanded in the region ppm. 8
10 13 C NMR 1 Fig. S4. 13 C NMR (100 MHz, CDCl 3 ) spectrum of compound 1. 9
11 DEPT 1 Fig. S5. DEPT spectrum of compound 1. 10
12 COSY 1 Fig. S6. 1 H 1 H COSY spectrum of compound 1. 11
13 NOESY 1 Fig. S7. NOESY spectrum of compound 1. 12
14 HSQC 1 Fig. S8. HSQC spectrum of compound 1. 13
15 HMBC 1 Fig. S9. HMBC spectrum of compound 1. 14
16 4,10 -Dihydroxy-5 H-1,11(13)-guaidien-8,12-olide (2) Colorless needle-like crystals; mp o C; [ ] 25 D +34 (c 0.4, MeOH); UV (MeOH) max (log ) 209 (3.84) nm; IR (KBr) max 3338, 2941, 1758, 1655, 1380, 1273, 1169 cm -1. APCIMS: m/z 265 [M + H] + (8), 247 [M H 2 O + H] + (51), 229 [M 2 H 2 O + H] + (100); HRESIMS m/z (calcd for C 15 H 21 O 4, ). Fig. S10. Crystal structure of compound 2 (ORTEP diagram) with displacement ellipsoids at 50% probability for non-h atoms. 15
17 1 H NMR 2 Fig. S11. 1 H NMR (400 MHz, methanol-d 4 ) spectrum of compound 2. 16
18 13 C NMR 2 Fig. S C NMR (100 MHz, methanol-d 4 ) spectrum of compound 2. 17
19 DEPT 2 Fig. S13. DEPT spectrum of compound 2. 18
20 COSY 2 Fig. S14. 1 H 1 H COSY spectrum of compound 2. 19
21 NOESY 2 Fig. S15. NOESY spectrum of compound 2. 20
22 HSQC 2 Fig. S16. HSQC spectrum of compound 2. 21
23 HMBC 2 Fig. S17. HMBC spectrum of compound 2. 22
24 4 -Hydroxy-1,2 -epoxy-5 H,10 H-11(13)-guaien-8,12-olide (3) Colorless crystals; mp o C; [ ] 25 D +31 (c 0.4, CHCl 3 ); UV (MeOH) max (log ) 210 (4.11) nm; IR (KBr) max 3497, 2949, 1757, 1658, 1398, 1271, 1131 cm -1 ; APCIMS: m/z 265 [M + H] + (13), 247 [M H 2 O + H] + (39), 229 [M 2 H 2 O + H] + (100); HRESIMS m/z (calcd for C 15 H 21 O 4, ). Fig. S18. Crystal structure of compound 3 (ORTEP diagram) with displacement ellipsoids at 50% probability for non-h atoms. 23
25 1 H NMR 3 Fig. S19. 1 H NMR (400 MHz, CDCl 3 ) spectrum of compound 3. 24
26 1 H NMR 3 Fig. S20. 1 H NMR (400 MHz, CDCl 3 ) spectrum of compound 3 expanded in the region ppm. 25
27 13 C NMR 3 Fig. S C NMR (100 MHz, CDCl 3 ) spectrum of compound 3. 26
28 DEPT 3 Fig. S22. DEPT spectrum of compound 3. 27
29 COSY 3 Fig. S23. 1 H 1 H COSY spectrum of compound 3. 28
30 NOESY 3 Fig. S24. NOESY spectrum of compound 3. 29
31 HSQC 3 Fig. S25. HSQC spectrum of compound 3. 30
32 HMBC 3 Fig. S26. HMBC spectrum of compound 3. 31
33 Calocephalin [4 -acetoxy-1,2 -epoxy-5 H,10 H-11(13)-guaien-8,12-olide] (4) Colorless crystals; mp o C; [ ] 25 D +14 (c 0.4, CHCl 3 ); UV (MeOH) (log ) 212 (4.12) nm; IR (KBr) max 3425, 2920, 1746, 1716, 1657, 1459, 1370, 1263, 1115, 1007 cm -1 ; APCIMS: m/z 307 [M + H] + (23), 264 [M + H Ac] + (16), 247 [M + H HOAc] + (100), 229 [M + H HOAc H 2 O] + (93); HRESIMS m/z (calcd for C 17 H 23 O 5, ). Fig. S27. Crystal structure of calocephalin (4) [ORTEP diagram] with displacement ellipsoids at 50% probability for non-h atoms. 32
34 1 H NMR 4 Fig. S28. 1 H NMR (400 MHz, CDCl 3 ) spectrum of calocephalin (4). 33
35 1 H NMR 4 Fig. S29. 1 H NMR (400 MHz, CDCl 3 ) spectrum of calocephalin (4) expanded in the region ppm. 34
36 13 C NMR 4 Fig. S C NMR (100 MHz, CDCl 3 ) spectrum of calocephalin (4). 35
37 DEPT 4 Fig. S31. DEPT spectrum of calocephalin (4). 36
38 COSY 4 Fig. S32. 1 H 1 H COSY spectrum of calocephalin (4). 37
39 NOESY 4 Fig. S33. NOESY spectrum of calocephalin (4). 38
40 HSQC 4 Fig. S34. HSQC spectrum of calocephalin (4). 39
41 HMBC 4 Fig. S35. HMBC spectrum of calocephalin (4). 40
42 1 H NMR 5 Fig. S36. 1 H NMR (400 MHz, CDCl 3 ) spectrum of the new compound 5. 41
43 1 H NMR 5 Fig. S37. 1 H NMR (400 MHz, CDCl 3 ) spectrum of the new compound 5 expanded in the region ppm. 42
44 1 H NMR 5 Fig. S38. 1 H NMR (400 MHz, CDCl 3 ) spectrum of the new compound 5 expanded in the region ppm. 43
45 13 C NMR 5 Fig. S C NMR (100 MHz, CDCl 3 ) spectrum of the new compound 5. 44
46 DEPT 5 Fig. S40. DEPT spectrum of the new compound 5. 45
47 COSY 5 Fig. S41. 1 H 1 H COSY spectrum of the new compound 5. 46
48 NOESY 5 Fig. S42. NOESY spectrum of the new compound 5. 47
49 HSQC 5 Fig. S43. HSQC spectrum of the new compound 5. 48
50 HMBC 5 Fig. S44. HMBC spectrum of the new compound 5. 49
51 1 H NMR 6 Fig. S45. 1 H NMR (400 MHz, methanol-d 4 ) spectrum of the new compound 6. 50
52 1 H NMR 6 Fig. S46. 1 H NMR (400 MHz, methanol-d 4 ) spectrum of the new compound 6 expanded in the region ppm. 51
53 13 C NMR 6 Fig. S C NMR (100 MHz, methanol-d 4 ) spectrum of the new compound 6. 52
54 DEPT 6 Fig. S48. DEPT spectrum of the new compound 6. 53
55 COSY 6 Fig. S49. 1 H 1 H COSY spectrum of the new compound 6. 54
56 NOESY 6 Fig. S50. NOESY spectrum of the new compound 6. 55
57 HSQC 6 Fig. S51. HSQC spectrum of the new compound 6. 56
58 HMBC 6 Fig. S52. HMBC spectrum of the new compound 6. 57
59 Pseudoivalin [4 -hydroxy-5 H-10,11(13)-guaidien-8,12-olide] (7) Colorless crystals; mp o C; [ ] 25 D 146 (c 0.4, CHCl 3 ); UV (MeOH) max (log ) 214 (4.15) nm; IR (KBr) max 3578, 3342, 2971, 1772, 1754, 1640, 1308, 1105 cm -1 ; APCIMS: m/z 249 [M + H] + (21), 231 [M + H H 2 O] + (100); HRESIMS m/z (calcd for C 15 H 21 O 3, ). Fig. S53. Crystal structure of pseudoivalin (7) [ORTEP diagram] with displacement ellipsoids at 50% probability for non-h atoms. 58
60 1 H NMR 7 Fig. S54. 1 H NMR (400 MHz, CDCl 3 ) spectrum of pseudoivalin (7). 59
61 1 H NMR 7 Fig. S55. 1 H NMR (400 MHz, CDCl 3 ) spectrum of pseudoivalin (7) expanded in the region ppm. 60
62 13 C NMR 7 Fig. S C NMR (100 MHz, CDCl 3 ) spectrum of pseudoivalin (7). 61
63 DEPT 7 Fig. S57. DEPT spectrum of pseudoivalin (7). 62
64 COSY 7 Fig. S58. 1 H 1 H COSY spectrum of pseudoivalin (7). 63
65 NOESY 7 Fig. S59. NOESY spectrum of pseudoivalin (7). 64
66 HSQC 7 Fig. S60. HSQC spectrum of pseudoivalin (7). 65
67 HMBC 7 Fig. S61. HMBC spectrum of pseudoivalin (7). 66
68 Pseudoivalin acetate [4 -acetoxy-5 H-10,11(13)-guaidien-8,12-olide] (8) Colorless crystals; mp o C; [ ] 25 D 164 (c 0.4, CHCl 3 ); UV (MeOH) max (log ) 207 (4.05) nm; IR (KBr) max 3430, 2942, 1766, 1725, 1664, 1373, 1260, 1117, 1060 cm -1 ; APCIMS: m/z 248 [M + H Ac] + (21), 231 [M + H HOAc] + (100); HRESIMS m/z (calcd for C 17 H 22 O 4 Na, ). Fig. S62. Crystal structure of pseudoivalin acetate (8) [ORTEP diagram] with displacement ellipsoids at 50% probability for non-h atoms. 67
69 1 H NMR 8 Fig. S63. 1 H NMR (400 MHz, CDCl 3 ) spectrum of pseudoivalin acetate (8). 68
70 1 H NMR 8 Fig. S64. 1 H NMR (400 MHz, CDCl 3 ) spectrum of pseudoivalin acetate (8) expanded in the region ppm. 69
71 13 C NMR 8 Fig. S C NMR (100 MHz, CDCl 3 ) spectrum of pseudoivalin acetate (8). 70
72 DEPT 8 Fig. S66. DEPT spectrum of pseudoivalin acetate (8). 71
73 COSY 8 Fig. S67. 1 H 1 H COSY spectrum of pseudoivalin acetate (8). 72
74 NOESY 8 Fig. S68. NOESY spectrum of pseudoivalin acetate (8). 73
75 HSQC 8 Fig. S69. HSQC spectrum of pseudoivalin acetate (8). 74
76 HMBC 8 Fig. S70. HMBC spectrum of pseudoivalin acetate (8). 75
77 Tomentosin (9) Colorless oil; [ ] D (c 0.4, CHCl 3 ); UV (MeOH) max (log ) 215 (4.12) nm; APCIMS: m/z 249 [M + H] + (100), 231 [M + H H 2 O] + (65); HRESIMS m/z (calcd for C 15 H 21 O 3, ). 76
78 1 H NMR 9 Fig. S71. 1 H NMR (400 MHz, CDCl 3 ) spectrum of tomentosin (9). 77
79 1 H NMR 9 Fig. S72. 1 H NMR (400 MHz, CDCl 3 ) spectrum of tomentosin (9) expanded in the region ppm. 78
80 13 C NMR 9 Fig. S C NMR (100 MHz, CDCl 3 ) spectrum of tomentosin (9). 79
81 DEPT 9 Fig. S74. DEPT spectrum of tomentosin (9). 80
82 COSY 9 Fig. S75. 1 H 1 H COSY spectrum of tomentosin (9). 81
83 NOESY 9 Fig. S76. NOESY spectrum of tomentosin (9). 82
84 HSQC 9 Fig. S77. HSQC spectrum of tomentosin (9). 83
85 HMBC 9 Fig. S78. HMBC spectrum of tomentosin (9). 84
86 1 H NMR 10 Fig. S79. 1 H NMR (400 MHz, CDCl 3 ) spectrum of the new compound
87 1 H NMR 10 Fig. S80. 1 H NMR (400 MHz, CDCl 3 ) spectrum of the new compound 10 expanded in the region ppm. 86
88 13 C NMR 10 Fig. S C NMR (100 MHz, CDCl 3 ) spectrum of the new compound
89 13 C NMR 10 Fig. S82. DEPT spectrum of the new compound
90 COSY 10 Fig. S83. 1 H 1 H COSY spectrum of the new compound
91 NOESY 10 Fig. S84. NOESY spectrum of the new compound
92 HSQC 10 Fig. S85. HSQC spectrum of the new compound
93 HMBC 10 Fig. S86. HMBC spectrum of the new compound
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