truncateols o v, further isoprenylated cyclohexanols from the … · 2018. 9. 22. · 16 figure...
TRANSCRIPT
Truncateols OV, further isoprenylated cyclohexanols
from the sponge-associated fungus Truncatella
angustata with antiviral activities
Supporting Information
List of Contents
no. Content
1 Figure S1. The IR Spectrum of Compound 1
2 Figure S2. HRESIMS Data of Compound 1
3 Figure S3. The 1H NMR Spectrum of Compound 1 in DMSO-d6 (400 MHz)
4 Figure S4. The APT Spectrum of Compound 1 in DMSO-d6 (100 MHz)
5 Figure S5. The HSQC Spectrum of Compound 1 in DMSO-d6 (400 MHz for 1H)
6 Figure S6. The 1H-
1H COSY Spectrum of Compound 1 in DMSO-d6 (400 MHz)
7 Figure S7. The HMBC Spectrum of Compound 1 in DMSO-d6 (400 MHz for 1H)
8 Figure S8. The NOESY Spectrum of Compound 1 in DMSO-d6 (400 MHz)
9 Figure S9. The 1H NMR Spectrum of Compound 1a in CDCl3 (400 MHz)
10 Figure S10. The 1H NMR Spectrum of Compound 1b in CDCl3 (400 MHz)
11 Figure S11. The IR Spectrum of Compound 2
12 Figure S12. HRESIMS Data of Compound 2
13 Figure S13. The 1H NMR Spectrum of Compound 2 in DMSO-d6 (400 MHz)
14 Figure S14. The APT Spectrum of Compound 2 in DMSO-d6 (100 MHz)
15 Figure S15. The HSQC Spectrum of Compound 2 in DMSO-d6 (400 MHz for 1H)
16 Figure S16. The 1H-
1H COSY Spectrum of Compound 2 in DMSO-d6 (400 MHz)
17 Figure S17. The HMBC Spectrum of Compound 2 in DMSO-d6 (400 MHz for 1H)
18 Figure S18. The NOESY Spectrum of Compound 2 in DMSO-d6 (400 MHz)
19 Figure S19. The 1H NMR Spectrum of Compound 2a in CDCl3 (400 MHz)
20 Figure S20. The 1H NMR Spectrum of Compound 2b in CDCl3 (400 MHz)
21 Figure S21. The IR Spectrum of Compound 3
22 Figure S22. HRESIMS Data of Compound 3
23 Figure S23. The 1H NMR Spectrum of Compound 3 in DMSO-d6 (400 MHz)
24 Figure S24. The APT Spectrum of Compound 3 in DMSO-d6 (100 MHz)
25 Figure S25. The HSQC Spectrum of Compound 3 in DMSO-d6 (400 MHz for 1H)
26 Figure S26. The 1H-
1H COSY Spectrum of Compound 3 in DMSO-d6 (400 MHz)
27 Figure S27. The HMBC Spectrum of Compound 3 in DMSO-d6 (400 MHz for 1H)
28 Figure S28. The NOESY Spectrum of Compound 3 in DMSO-d6 (400 MHz)
29 Figure S29. The 1H NMR Spectrum of Compound 3a in CDCl3 (400 MHz)
30 Figure S30. The 1H NMR Spectrum of Compound 3b in CDCl3 (400 MHz)
31 Figure S31. The IR Spectrum of Compound 4
32 Figure S32. HRESIMS Data of Compound 4
33 Figure S33. The 1H NMR Spectrum of Compound 4 in DMSO-d6 (400 MHz)
34 Figure S34. The APT Spectrum of Compound 4 in DMSO-d6 (100 MHz)
35 Figure S35. The HSQC Spectrum of Compound 4 in DMSO-d6 (400 MHz for 1H)
36 Figure S36. The 1H-
1H COSY Spectrum of Compound 4 in DMSO-d6 (400 MHz)
37 Figure S37. The HMBC Spectrum of Compound 4 in DMSO-d6 (400 MHz for 1H)
38 Figure S38. The NOESY Spectrum of Compound 4 in DMSO-d6 (400 MHz for 1H)
39 Figure S39. The 1H NMR Spectrum of Compound 4a in CDCl3 (400 MHz)
40 Figure S40. The 1H NMR Spectrum of Compound 4b in CDCl3 (400 MHz)
41 Figure S41. The IR Spectrum of Compound 5
42 Figure S42. HRESIMS Data of Compound 5
43 Figure S43. The 1H NMR Spectrum of Compound 5 in DMSO-d6 (400 MHz)
44 Figure S44. The APT Spectrum of Compound 5 in DMSO-d6 (100 MHz)
45 Figure S45. The HSQC Spectrum of Compound 5 in DMSO-d6 (400 MHz for 1H)
46 Figure S46. The 1H-
1H COSY Spectrum of Compound 5 in DMSO-d6 (400 MHz)
47 Figure S47. The HMBC Spectrum of Compound 5 in DMSO-d6 (400 MHz for 1H)
48 Figure S48. The NOESY Spectrum of Compound 5 in DMSO-d6 (400 MHz for 1H)
49 Figure S49. The 1H NMR Spectrum of Compound 5a in CDCl3 (400 MHz)
50 Figure S50. The 1H NMR Spectrum of Compound 5b in CDCl3 (400 MHz)
51 Figure S51. The IR Spectrum of Compound 6
52 Figure S52. ESIMS Data of Compound 6
53 Figure S53. The 1H NMR Spectrum of Compound 6 in DMSO-d6 (400 MHz)
54 Figure S54. The APT Spectrum of Compound 49 in DMSO-d6 (100 MHz)
55 Figure S55. The HSQC Spectrum of Compound 50 in DMSO-d6 (400 MHz for 1H)
56 Figure S56. The 1H-
1H COSY Spectrum of Compound 6 in DMSO-d6 (400 MHz)
57 Figure S57. The HMBC Spectrum of Compound 6 in DMSO-d6 (400 MHz for 1H)
58 Figure S58. The NOESY Spectrum of Compound 6 in DMSO-d6 (500 MHz for 1H)
59 Figure S59. The CD Spectrum of Compound 6 in MeOH
60 Figure S60. The IR Spectrum of Compound 7
61 Figure S61. ESIMS Data of Compound 7
62 Figure S62. The 1H NMR Spectrum of Compound 7 in DMSO-d6 (400 MHz)
63 Figure S63. The APT Spectrum of Compound 7 in DMSO-d6 (100 MHz)
64 Figure S64. The HSQC Spectrum of Compound 7 in DMSO-d6 (400 MHz for 1H)
65 Figure S65. The 1H-
1H COSY Spectrum of Compound 7 in DMSO-d6 (400 MHz)
66 Figure S66. The HMBC Spectrum of Compound 7 in DMSO-d6 (400 MHz for 1H)
67 Figure S67. The NOESY Spectrum of Compound 7 in DMSO-d6 (400 MHz for 1H)
68 Figure S68. ESIMS Data of Compound 8
69 Figure S69. The 1H NMR Spectrum of Compound 8 in DMSO-d6 (400 MHz)
70 Figure S70. The APT Spectrum of Compound 8 in DMSO-d6 (100 MHz)
71 Figure S71. The HSQC Spectrum of Compound 8 in DMSO-d6 (400 MHz for 1H)
72 Figure S72. The 1H -1H COSY Spectrum of Compound 8 in DMSO-d6 (400 MHz)
73 Figure S73. The HMBC Spectrum of Compound 8 in DMSO-d6 (400 MHz for 1H)
74 Figure S74. The CD Spectrum of Compound 8 in MeOH
Figure S1. The IR Spectrum of Compound 1
Figure S2. HRESIMS Data of Compound 1
Figure S3. The 1H NMR Spectrum of Compound 1 in DMSO-d6 (400 MHz)
Figure S4. The APT Spectrum of Compound 1 in DMSO-d6 (100 MHz)
Figure S5. The HSQC Spectrum of Compound 1 in DMSO-d6 (400 MHz for 1H)
Figure S6. The 1H-
1H COSY Spectrum of Compound 1 in DMSO-d6 (400 MHz)
Figure S7. The HMBC Spectrum of Compound 1 in DMSO-d6 (400 MHz for 1H)
Figure S8. The NOESY Spectrum of Compound 1 in DMSO-d6 (400 MHz for 1H)
Figure S9. The 1H NMR Spectrum of Compound 1a in CDCl3 (400 MHz)
Figure S10. The 1H NMR Spectrum of Compound 1b in CDCl3 (400 MHz)
Figure S11. The IR Spectrum of Compound 2
Figure S12. HRESIMS Data of Compound 2
Figure S13. The 1H NMR Spectrum of Compound 2 in DMSO-d6 (400 MHz)
Figure S14. The APT Spectrum of Compound 2 in DMSO-d6 (100 MHz)
Figure S15. The HSQC Spectrum of Compound 2 in DMSO-d6 (400 MHz for 1H)
Figure S16. The 1H-
1H COSY Spectrum of Compound 2 in DMSO-d6 (400 MHz)
Figure S17. The HMBC Spectrum of Compound 2 in DMSO-d6 (400 MHz for 1H)
Figure S18. The NOESY Spectrum of Compound 2 in DMSO-d6 (400 MHz for 1H)
Figure S19. The 1H NMR Spectrum of Compound 2a in CDCl3 (400 MHz)
Figure S20. The 1H NMR Spectrum of Compound 2b in CDCl3 (400 MHz)
Figure S21. The IR Spectrum of Compound 3
Figure S22. HRESIMS Data of Compound 3
B4-2-3-ftms_140415135149 #4 RT: 0.08 AV: 1 NL: 2.34E8T: FTMS + p ESI Full ms [100.00-1000.00]
100 150 200 250 300 350 400 450 500 550 600 650 700
m/z
0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
85
90
95
100
Re
lative
Ab
un
da
nce
303.1565
333.1672
263.1642177.0909
351.1778 417.1369 583.3241 713.2818512.5032 619.5271
Figure S23. The 1H NMR Spectrum of Compound 3 in DMSO-d6 (400 MHz)
Figure S24. The APT Spectrum of Compound 3 in DMSO-d6 (100 MHz)
Figure S25. The HSQC Spectrum of Compound 3 in DMSO-d6 (400 MHz for 1H)
Figure S26. The 1H-
1H COSY Spectrum of Compound 3 in DMSO-d6 (400 MHz)
Figure S27. The HMBC Spectrum of Compound 3 in DMSO-d6 (400 MHz for 1H)
Figure S28. The NOESY Spectrum of Compound 3 in DMSO-d6 (400 MHz for 1H)
Figure S29. The 1H NMR Spectrum of Compound 3a in CDCl3 (400 MHz)
Figure S30. The 1H NMR Spectrum of Compound 3b in CDCl3 (400 MHz)
Figure S31. The IR Spectrum of Compound 4
Figure S32. HRESIMS Data of Compound 4
WatersXevo G2 Q-TOF/YCA166# 09-Mar-2015
m/z200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360
%
0
100
B4-3-3 10 (0.199) Cm (10:13) 1: TOF MS ES+ 4.72e5243.1087
240.0899
237.0836201.0827
235.1199
231.0482
205.0838
207.0865
225.0610215.0730
279.1595
253.0635
270.0535254.0731
298.1329
290.1441
280.1628
305.0254 340.1588
337.1253
321.0507307.1192332.1698
340.6599 354.1042
Figure S33. The 1H NMR Spectrum of Compound 4 in DMSO-d6 (400 MHz)
Figure S34. The APT Spectrum of Compound 4 in DMSO-d6 (100 MHz)
Figure S35. The HSQC Spectrum of Compound 4 in DMSO-d6 (400 MHz for 1H)
Figure S36. The 1H-
1H COSY Spectrum of Compound 4 in DMSO-d6 (400 MHz)
Figure S37. The HMBC Spectrum of Compound 4 in DMSO-d6 (400 MHz for 1H)
Figure S38. The NOESY Spectrum of Compound 4 in DMSO-d6 (400 MHz for 1H)
Figure S39. The 1H NMR Spectrum of Compound 4a in CDCl3 (400 MHz)
Figure S40. The 1H NMR Spectrum of Compound 4b in CDCl3 (400 MHz)
Figure S41. The IR Spectrum of Compound 5
Figure S42. HRESIMS Data of Compound 5
Figure S43. The 1H NMR Spectrum of Compound 5 in DMSO-d6 (400 MHz)
Figure S44. The APT Spectrum of Compound 5 in DMSO-d6 (100 MHz)
Figure S45. The HSQC Spectrum of Compound 5 in DMSO-d6 (400 MHz for 1H)
Figure S46. The 1H-
1H COSY Spectrum of Compound 5 in DMSO-d6 (400 MHz)
Figure S47. The HMBC Spectrum of Compound 5 in DMSO-d6 (400 MHz for 1H)
Figure S48. The NOESY Spectrum of Compound 5 in DMSO-d6 (400 MHz for 1H)
Figure S49. The 1H NMR Spectrum of Compound 5a in CDCl3 (400 MHz)
Figure S50. The 1H NMR Spectrum of Compound 5b in CDCl3 (400 MHz)
Figure S51. The IR Spectrum of Compound 6
Figure S52. HRESIMS Data of Compound 6
Figure S53. The 1H NMR Spectrum of Compound 6 in DMSO-d6 (500 MHz)
Figure S54. The APT Spectrum of Compound 6 in DMSO-d6 (125 MHz)
Figure S55. The HSQC Spectrum of Compound 6 in DMSO-d6 (500 MHz for 1H)
Figure S56. The 1H-
1H COSY Spectrum of Compound 6 in DMSO-d6 (500 MHz)
Figure S57. The HMBC Spectrum of Compound 6 in DMSO-d6 (500 MHz for 1H)
Figure S58. The NOESY Spectrum of Compound 6 in DMSO-d6 (500 MHz for 1H)
Figure S59. The CD Spectrum of Compound 6 in MeOH
Figure S60. The IR Spectrum of Compound 7
Figure S61. HRESIMS Data of Compound 7
Figure S62. The 1H NMR Spectrum of Compound 7 in DMSO-d6 (500 MHz)
WatersXevo G2 Q-TOF/YCA166# 09-Mar-2015
m/z120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 540 560 580 600 620
%
0
100
B5-7 NEGHRMS 12 (0.233) Cm (10:16-(2:5+22:51)) 1: TOF MS ES- 1.41e6359.1263
349.0977
313.1214277.1443
263.0691237.1125174.9550
115.5333
361.1238
367.1395393.1315
427.1137411.0933
443.1085
529.1057501.0585 569.3619591.2715
Figure S63. The APT Spectrum of Compound 7 in DMSO-d6 (125MHz)
Figure S64. The HSQC Spectrum of Compound 7 in DMSO-d6 (500 MHz for 1H)
Figure S65. The 1H-
1H COSY Spectrum of Compound 7 in DMSO-d6 (500 MHz)
Figure S66. The HMBC Spectrum of Compound 7 in DMSO-d6 (500 MHz for 1H)
Figure S67. The NOESY Spectrum of Compound 7 in DMSO-d6 (500 MHz for 1H)
Figure S68. ESIMS Data of Compound 8
Figure S69. The 1H NMR Spectrum of Compound 8 in DMSO-d6 (400 MHz)
Figure S70. The APT Spectrum of Compound 8 in DMSO-d6 (100 MHz)
Figure S71. The HSQC Spectrum of Compound 8 in DMSO-d6 (400 MHz for 1H)
Figure S72. The 1H-
1H COSY Spectrum of Compound 8 in DMSO-d6 (400 MHz)
Figure S73. The HMBC Spectrum of Compound 8 in DMSO-d6 (400 MHz for 1H)
Figure S74. The CD Spectrum of Compound 8 in MeOH