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