Labdane-type Diterpenoids from the Fruits of Vitex trifolia
Supporting Information
Labdane-type Diterpenoids from the Fruits of Vitex trifolia Cheng-Jian Zheng,†, Jian-Yong Zhu,†, Wu Yu,† Xue-Qin Ma,†,‡ Khalid Rahman,§ and Lu-Ping Qin*,† †
Department of Pharmacognosy, School of Pharmacy, Second Military Medical
University, Shanghai 200433, People’s Republic of China ‡
Department of Pharmaceutical Analysis, School of Pharmacy, NingXia Medical
University, Yinchuan 750004, People’s Republic of China §
Faculty of Science, School of Biomolecular Sciences, Liverpool John Moores
University, Liverpool L3 3AF, UK
Supporting Information S1. 1H NMR (400 MHz, CDCl3) spectrum of vitextrifolin A (1) S2. 13C NMR (100 MHz, CDCl3) spectrum of vitextrifolin A (1) S3. 1H-1H COSY spectrum of vitextrifolin A (1) in CDCl3 S4. HSQC spectrum of vitextrifolin A (1) in CDCl3 S5. HMBC spectrum of vitextrifolin A (1) in CDCl3 S6. NOESY spectrum of vitextrifolin A (1) in CDCl3 S7. HRESIMS spectrum of vitextrifolin A (1) S8. IR (KBr disc) spectrum of vitextrifolin A (1) S9. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin B (2) 1
S10. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin B (2) S11. 1H-1H COSY spectrum of vitextrifolin B (2) in CDCl3 S12. HSQC spectrum of vitextrifolin B (2) in CDCl3 S13. HMBC spectrum of vitextrifolin B (2) in CDCl3 S14. NOESY spectrum of vitextrifolin B (2) in CDCl3 S15. HRESIMS spectrum of vitextrifolin B (2) S16. IR (KBr disc) spectrum of vitextrifolin B (2) S17. 1H NMR (600 MHz, CD3OD) spectrum of vitextrifolin C (3) S18. 13C NMR (150 MHz, CD3OD) spectrum of vitextrifolin C (3) S19. 1H-1H COSY spectrum of vitextrifolin C (3) in CD3OD S20. HSQC spectrum of vitextrifolin C (3) in CD3OD S21. HMBC spectrum of vitextrifolin C (3) in CD3OD S22. NOESY spectrum of vitextrifolin C (3) in CD3OD S23. HRESIMS spectrum of vitextrifolin C (3) S24. IR (KBr disc) spectrum of vitextrifolin C (3) S25. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin D (4) S26. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin D (4) S27. 1H-1H COSY spectrum of vitextrifolin D (4) in CDCl3 S28. HSQC spectrum of vitextrifolin D (4) in CDCl3 S29. HMBC spectrum of vitextrifolin D (4) in CDCl3 S30.NOESY spectrum of vitextrifolin D (4) in CDCl3 S31. HRESIMS spectrum of vitextrifolin D (4) S32. IR (KBr disc) spectrum of vitextrifolin D (4) S33.1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin E (5) S34. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin E (5) S35. 1H-1H COSY spectrum of vitextrifolin E (5) in CDCl3 S36. HSQC spectrum of vitextrifolin E (5) in CDCl3 S37. HMBC spectrum of vitextrifolin E (5) in CDCl3 S38. NOESY spectrum of vitextrifolin E (5) in CDCl3 S39. HRESIMS spectrum of vitextrifolin E (5) 2
S40. IR (KBr disc) spectrum of vitextrifolin E (5) S41. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin F (6) S42. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin F (6) S43. 1H-1H COSY spectrum of vitextrifolin F (6) in CDCl3 S44. HSQC spectrum of vitextrifolin F (6) in CDCl3 S45. HMBC spectrum of vitextrifolin F (6) in CDCl3 S46. NOESY spectrum of vitextrifolin F (6) in CDCl3 S47. HRESIMS spectrum of vitextrifolin F (6) S48. IR (KBr disc) spectrum of vitextrifolin F (6) S49. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin G (7) S50. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin G (7) S51. 1H-1H COSY spectrum of vitextrifolin G (7) in CDCl3 S52. HSQC spectrum of vitextrifolin G (7) in CDCl3 S53. HMBC spectrum of vitextrifolin G (7) in CDCl3 S54. NOESY spectrum of vitextrifolin G (7) in CDCl3 S55. HRESIMS spectrum of vitextrifolin G (7) S56. IR (KBr disc) spectrum of vitextrifolin G (7)
3
S1. 1H NMR (400 MHz, CDCl3) spectrum of vitextrifolin A (1)
5.2
ZJM-29 ZJM-29 CDCl3 1H
5.4
4.956 4.941 4.926
H-15
5.0
1.00
4.8
H-3
4.6
1.09
4.4
4.540 4.522 4.511 4.251
H-16
4.2
0.91
4.0
MeO-16
3.8 3.6 3.2 3.0 2.4 2.2 2.0 1.6
2.030 1.685 1.681 1.674 1.649 1.643
Ac-1'
1.8
1.34 4.34 1.62 2.43 3.75
2.419 2.403 2.387 2.371
H-14β H-14α
2.8 2.6 f1 (ppm)
1.22
3.491 3.423
MeO-15
3.4
2.97 2.83
1.4 1.0 0.8
8 H-1
H-19
H-17
0.6
2.82 2.78 3.84 3.25
H-20
1.2
2.29 1.86
0.4
4
1.379 1.369 1.252 0.883 0.862 0.833 0.815 0.798
S2. 13C NMR (100 MHz, CDCl3) spectrum of vitextrifolin A (1)
180
170
C-1'
ZJM-29-二维 ZJM-29 DEPT135 CDCl3 BB+DEPT135
190
160
150
140
130
120
110
100
90 80 f1 (ppm)
70
60
50
40
30
20
10
0
-10
-20
5
S3. 1H-1H COSY spectrum of vitextrifolin A (1) in CDCl3
ZJM-29-二维 ZJM-29 CDCl3
6.0
COSY
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
0.5
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6
S4. HMQC spectrum of vitextrifolin A (1) in CDCl3
ZJM-29-二维 ZJM-29 CDCl3
5.4
HSQC
5.0
4.6
4.2
3.8
3.4
3.0 f2 (ppm)
2.6
2.2
1.8
1.4
1.0
0.6
10
20
30
40
50
60
70
80
90
100
110
7
S5. HMBC spectrum of vitextrifolin A (1) in CDCl3
8
S6. NOESY spectrum of vitextrifolin A (1) in CDCl3
4.8
CDCl3
5.0
ZJM-29 ZJM-29
5.2
NOESY
4.6
4.4
4.2
4.0
3.8
3.6
3.4
3.2
3.0 2.8 f2 (ppm)
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
9
S7. HRESIMS spectrum of vitextrifolin A (1)
10
S8. IR (KBr disc) spectrum of vitextrifolin A (1)
11
S9. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin B (2)
zmj-55 zmj-55
5.2
5.0
4.8
4.6
4.4
4.2
4.0
3.8
3.6
3.4
3.0
2.8 f1 (ppm)
MeO-15
3.2
2.4
-H-14β
2.6
2.2
Ac
2.0
1.8
1.6
1.4
1.2
-H-20
1.0
0.6
-H-17
19 H-
0.8
0.4
12
S10. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin B (2)
zmj-55 zmj-55
170
160
150
140
130
120
110
100
90
80 f1 (ppm)
70
60
50
40
30
20
10
0
-10
13
S11. 1H-1H COSY spectrum of vitextrifolin B (2) in CDCl3
zmj-55 zmj-55 cosy
5.0
4.5
4.0
3.5
3.0 f2 (ppm)
2.5
2.0
1.5
1.0
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
14
S12. HSQC spectrum of vitextrifolin B (2) in CDCl3
f1 (ppm)
15
S13. HMBC spectrum of vitextrifolin B (2) in CDCl3
zmj-55 zmj-55 hmbc
5.5
5.0
4.5
4.0
3.5
3.0 f2 (ppm)
2.5
2.0
1.5
1.0
10
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
16
S14. NOESY spectrum of vitextrifolin B (2) in CDCl3
5.0
zmj-55 zmj-55 noesy
5.2
4.8
4.6
4.4
4.2
4.0
3.8
3.6
3.4
3.2
3.0 2.8 2.6 f2 (ppm)
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
17
S15. HRESIMS spectrum of vitextrifolin B (2)
18
S16. IR (KBr disc) spectrum of vitextrifolin B (2)
19
S17. 1H NMR (600 MHz, CD3OD) spectrum of vitextrifolin C (3) zmj-65 zmj-65
Ac
20
S18. 13C NMR (150 MHz, CD3OD) spectrum of vitextrifolin C (3)
zmj-65 zmj-65
180
170
160
150
140
130
120
110
100
90 80 f1 (ppm)
70
60
50
40
30
20
10
0
21
S19. 1H-1H COSY spectrum of vitextrifolin C (3) in CDCl3
zmj-65 zmj-65 cosy
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
22
S20. HSQC spectrum of vitextrifolin C (3) in CDCl3
zmj-65 zmj-65 hsqc
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
10
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
190
23
S21. HMBC spectrum of vitextrifolin C (3) in CDCl3
f1 (ppm)
24
S22. NOESY spectrum of vitextrifolin C (3) in CDCl3
zmj-65 zmj-65 noesy
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
25
S23. HRESIMS spectrum of vitextrifolin C (3)
26
S24. IR (KBr disc) spectrum of vitextrifolin C (3)
27
S25. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin D (4)
zmj-66 zmj-66
6.2
6.0
5.8
5.6
5.4
5.2
5.0
4.8
4.6
4.4
4.2
4.0
3.8
3.6 3.4 f1 (ppm)
3.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
28
S26. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin D (4)
zmj-66 zmj-66
180
170
160
150
140
130
120
110
100 90 f1 (ppm)
80
70
60
50
40
30
20
10
29
S27. 1H-1H COSY spectrum of vitextrifolin D (4) in CDCl3
5.8
zmj-66 zmj-66 cosy
6.0
5.6
5.4
5.2
5.0
4.8
4.6
4.4
4.2
4.0
3.8
3.6 3.4 f2 (ppm)
3.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
30
S28. HSQC spectrum of vitextrifolin D (4) in CDCl3
zmj-66 zmj-66 hsqc
6.5
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
0.5
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
31
S29. HMBC spectrum of vitextrifolin D (4) in CDCl3
zmj-66 zmj-66 hmbc
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
32
S30.NOESY spectrum of vitextrifolin D (4) in CDCl3
33
S31. HRESIMS spectrum of vitextrifolin D (4)
34
S32. IR (KBr disc) spectrum of vitextrifolin D (4)
35
S33.1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin E (5)
zmj-72 zmj-72
6.0
H-14
5.8
5.6
5.4
5.2
5.0
4.6
H-16
4.8
4.4
4.2
4.0
3.8
3.6
3.4 3.2 f1 (ppm)
3.0
H-11
2.8
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
36
S34. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin E (5)
zmj-72 zmj-72
210
200
190
180
170
160
150
140
130
120
110 f1 (ppm)
100
90
80
C
70
60
50
40
30
20
10
37
S35. 1H-1H COSY spectrum of vitextrifolin E (5) in CDCl3
zmj-72 zmj-72 cosy
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
38
S36. HSQC spectrum of vitextrifolin E (5) in CDCl3
zmj-72 zmj-72 hsqc
6.0
5.5
5.0
4.5
4.0
3.5
3.0 f2 (ppm)
2.5
2.0
1.5
1.0
0.5
0
10
20
30
40
50
60
70
80
90
100
110
120
130
39
S37. HMBC spectrum of vitextrifolin E (5) in CDCl3
zmj-72 zmj-72 hmbc
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
20
40
60
80
100
120
140
160
180
200
40
S38. NOESY spectrum of vitextrifolin E (5) in CDCl3
zmj-72 zmj-72 noesy
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
41
S39. HRESIMS spectrum of vitextrifolin E (5)
42
S40. IR (KBr disc) spectrum of vitextrifolin E (5)
43
S41. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin F (6)
44
S42. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin F (6)
45
S43. 1H-1H COSY spectrum of vitextrifolin F (6) in CDCl3
46
S44. HSQC spectrum of vitextrifolin F (6) in CDCl3
47
S45. HMBC spectrum of vitextrifolin F (6) in CDCl3
48
S46. NOESY spectrum of vitextrifolin F (6) in CDCl3
49
S47. HRESIMS spectrum of vitextrifolin F (6)
50
S48. IR (KBr disc) spectrum of vitextrifolin F (6)
51
S49. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin G (7)
52
S50. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin G (7)
53
S51. 1H-1H COSY spectrum of vitextrifolin G (7) in CDCl3
54
S52. HSQC spectrum of vitextrifolin G (7) in CDCl3
55
S53. HMBC spectrum of vitextrifolin G (7) in CDCl3
56
S54. NOESY spectrum of vitextrifolin G (7) in CDCl3
57
S55. HRESIMS spectrum of vitextrifolin G (7)
58
S56. IR (KBr disc) spectrum of vitextrifolin G (7)
59
Labdane-type Diterpenoids from the Fruits of Vitex trifolia Cheng-Jian Zheng,†, Jian-Yong Zhu,†, Wu Yu,† Xue-Qin Ma,†,‡ Khalid Rahman,§ and Lu-Ping Qin*,† †
Department of Pharmacognosy, School of Pharmacy, Second Military Medical
University, Shanghai 200433, People’s Republic of China ‡
Department of Pharmaceutical Analysis, School of Pharmacy, NingXia Medical
University, Yinchuan 750004, People’s Republic of China §
Faculty of Science, School of Biomolecular Sciences, Liverpool John Moores
University, Liverpool L3 3AF, UK
Supporting Information S1. 1H NMR (400 MHz, CDCl3) spectrum of vitextrifolin A (1) S2. 13C NMR (100 MHz, CDCl3) spectrum of vitextrifolin A (1) S3. 1H-1H COSY spectrum of vitextrifolin A (1) in CDCl3 S4. HSQC spectrum of vitextrifolin A (1) in CDCl3 S5. HMBC spectrum of vitextrifolin A (1) in CDCl3 S6. NOESY spectrum of vitextrifolin A (1) in CDCl3 S7. HRESIMS spectrum of vitextrifolin A (1) S8. IR (KBr disc) spectrum of vitextrifolin A (1) S9. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin B (2) 1
S10. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin B (2) S11. 1H-1H COSY spectrum of vitextrifolin B (2) in CDCl3 S12. HSQC spectrum of vitextrifolin B (2) in CDCl3 S13. HMBC spectrum of vitextrifolin B (2) in CDCl3 S14. NOESY spectrum of vitextrifolin B (2) in CDCl3 S15. HRESIMS spectrum of vitextrifolin B (2) S16. IR (KBr disc) spectrum of vitextrifolin B (2) S17. 1H NMR (600 MHz, CD3OD) spectrum of vitextrifolin C (3) S18. 13C NMR (150 MHz, CD3OD) spectrum of vitextrifolin C (3) S19. 1H-1H COSY spectrum of vitextrifolin C (3) in CD3OD S20. HSQC spectrum of vitextrifolin C (3) in CD3OD S21. HMBC spectrum of vitextrifolin C (3) in CD3OD S22. NOESY spectrum of vitextrifolin C (3) in CD3OD S23. HRESIMS spectrum of vitextrifolin C (3) S24. IR (KBr disc) spectrum of vitextrifolin C (3) S25. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin D (4) S26. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin D (4) S27. 1H-1H COSY spectrum of vitextrifolin D (4) in CDCl3 S28. HSQC spectrum of vitextrifolin D (4) in CDCl3 S29. HMBC spectrum of vitextrifolin D (4) in CDCl3 S30.NOESY spectrum of vitextrifolin D (4) in CDCl3 S31. HRESIMS spectrum of vitextrifolin D (4) S32. IR (KBr disc) spectrum of vitextrifolin D (4) S33.1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin E (5) S34. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin E (5) S35. 1H-1H COSY spectrum of vitextrifolin E (5) in CDCl3 S36. HSQC spectrum of vitextrifolin E (5) in CDCl3 S37. HMBC spectrum of vitextrifolin E (5) in CDCl3 S38. NOESY spectrum of vitextrifolin E (5) in CDCl3 S39. HRESIMS spectrum of vitextrifolin E (5) 2
S40. IR (KBr disc) spectrum of vitextrifolin E (5) S41. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin F (6) S42. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin F (6) S43. 1H-1H COSY spectrum of vitextrifolin F (6) in CDCl3 S44. HSQC spectrum of vitextrifolin F (6) in CDCl3 S45. HMBC spectrum of vitextrifolin F (6) in CDCl3 S46. NOESY spectrum of vitextrifolin F (6) in CDCl3 S47. HRESIMS spectrum of vitextrifolin F (6) S48. IR (KBr disc) spectrum of vitextrifolin F (6) S49. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin G (7) S50. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin G (7) S51. 1H-1H COSY spectrum of vitextrifolin G (7) in CDCl3 S52. HSQC spectrum of vitextrifolin G (7) in CDCl3 S53. HMBC spectrum of vitextrifolin G (7) in CDCl3 S54. NOESY spectrum of vitextrifolin G (7) in CDCl3 S55. HRESIMS spectrum of vitextrifolin G (7) S56. IR (KBr disc) spectrum of vitextrifolin G (7)
3
S1. 1H NMR (400 MHz, CDCl3) spectrum of vitextrifolin A (1)
5.2
ZJM-29 ZJM-29 CDCl3 1H
5.4
4.956 4.941 4.926
H-15
5.0
1.00
4.8
H-3
4.6
1.09
4.4
4.540 4.522 4.511 4.251
H-16
4.2
0.91
4.0
MeO-16
3.8 3.6 3.2 3.0 2.4 2.2 2.0 1.6
2.030 1.685 1.681 1.674 1.649 1.643
Ac-1'
1.8
1.34 4.34 1.62 2.43 3.75
2.419 2.403 2.387 2.371
H-14β H-14α
2.8 2.6 f1 (ppm)
1.22
3.491 3.423
MeO-15
3.4
2.97 2.83
1.4 1.0 0.8
8 H-1
H-19
H-17
0.6
2.82 2.78 3.84 3.25
H-20
1.2
2.29 1.86
0.4
4
1.379 1.369 1.252 0.883 0.862 0.833 0.815 0.798
S2. 13C NMR (100 MHz, CDCl3) spectrum of vitextrifolin A (1)
180
170
C-1'
ZJM-29-二维 ZJM-29 DEPT135 CDCl3 BB+DEPT135
190
160
150
140
130
120
110
100
90 80 f1 (ppm)
70
60
50
40
30
20
10
0
-10
-20
5
S3. 1H-1H COSY spectrum of vitextrifolin A (1) in CDCl3
ZJM-29-二维 ZJM-29 CDCl3
6.0
COSY
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
0.5
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6
S4. HMQC spectrum of vitextrifolin A (1) in CDCl3
ZJM-29-二维 ZJM-29 CDCl3
5.4
HSQC
5.0
4.6
4.2
3.8
3.4
3.0 f2 (ppm)
2.6
2.2
1.8
1.4
1.0
0.6
10
20
30
40
50
60
70
80
90
100
110
7
S5. HMBC spectrum of vitextrifolin A (1) in CDCl3
8
S6. NOESY spectrum of vitextrifolin A (1) in CDCl3
4.8
CDCl3
5.0
ZJM-29 ZJM-29
5.2
NOESY
4.6
4.4
4.2
4.0
3.8
3.6
3.4
3.2
3.0 2.8 f2 (ppm)
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
9
S7. HRESIMS spectrum of vitextrifolin A (1)
10
S8. IR (KBr disc) spectrum of vitextrifolin A (1)
11
S9. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin B (2)
zmj-55 zmj-55
5.2
5.0
4.8
4.6
4.4
4.2
4.0
3.8
3.6
3.4
3.0
2.8 f1 (ppm)
MeO-15
3.2
2.4
-H-14β
2.6
2.2
Ac
2.0
1.8
1.6
1.4
1.2
-H-20
1.0
0.6
-H-17
19 H-
0.8
0.4
12
S10. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin B (2)
zmj-55 zmj-55
170
160
150
140
130
120
110
100
90
80 f1 (ppm)
70
60
50
40
30
20
10
0
-10
13
S11. 1H-1H COSY spectrum of vitextrifolin B (2) in CDCl3
zmj-55 zmj-55 cosy
5.0
4.5
4.0
3.5
3.0 f2 (ppm)
2.5
2.0
1.5
1.0
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
14
S12. HSQC spectrum of vitextrifolin B (2) in CDCl3
f1 (ppm)
15
S13. HMBC spectrum of vitextrifolin B (2) in CDCl3
zmj-55 zmj-55 hmbc
5.5
5.0
4.5
4.0
3.5
3.0 f2 (ppm)
2.5
2.0
1.5
1.0
10
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
16
S14. NOESY spectrum of vitextrifolin B (2) in CDCl3
5.0
zmj-55 zmj-55 noesy
5.2
4.8
4.6
4.4
4.2
4.0
3.8
3.6
3.4
3.2
3.0 2.8 2.6 f2 (ppm)
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
17
S15. HRESIMS spectrum of vitextrifolin B (2)
18
S16. IR (KBr disc) spectrum of vitextrifolin B (2)
19
S17. 1H NMR (600 MHz, CD3OD) spectrum of vitextrifolin C (3) zmj-65 zmj-65
Ac
20
S18. 13C NMR (150 MHz, CD3OD) spectrum of vitextrifolin C (3)
zmj-65 zmj-65
180
170
160
150
140
130
120
110
100
90 80 f1 (ppm)
70
60
50
40
30
20
10
0
21
S19. 1H-1H COSY spectrum of vitextrifolin C (3) in CDCl3
zmj-65 zmj-65 cosy
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
22
S20. HSQC spectrum of vitextrifolin C (3) in CDCl3
zmj-65 zmj-65 hsqc
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
10
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
190
23
S21. HMBC spectrum of vitextrifolin C (3) in CDCl3
f1 (ppm)
24
S22. NOESY spectrum of vitextrifolin C (3) in CDCl3
zmj-65 zmj-65 noesy
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
25
S23. HRESIMS spectrum of vitextrifolin C (3)
26
S24. IR (KBr disc) spectrum of vitextrifolin C (3)
27
S25. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin D (4)
zmj-66 zmj-66
6.2
6.0
5.8
5.6
5.4
5.2
5.0
4.8
4.6
4.4
4.2
4.0
3.8
3.6 3.4 f1 (ppm)
3.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
28
S26. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin D (4)
zmj-66 zmj-66
180
170
160
150
140
130
120
110
100 90 f1 (ppm)
80
70
60
50
40
30
20
10
29
S27. 1H-1H COSY spectrum of vitextrifolin D (4) in CDCl3
5.8
zmj-66 zmj-66 cosy
6.0
5.6
5.4
5.2
5.0
4.8
4.6
4.4
4.2
4.0
3.8
3.6 3.4 f2 (ppm)
3.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
30
S28. HSQC spectrum of vitextrifolin D (4) in CDCl3
zmj-66 zmj-66 hsqc
6.5
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
0.5
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
31
S29. HMBC spectrum of vitextrifolin D (4) in CDCl3
zmj-66 zmj-66 hmbc
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
32
S30.NOESY spectrum of vitextrifolin D (4) in CDCl3
33
S31. HRESIMS spectrum of vitextrifolin D (4)
34
S32. IR (KBr disc) spectrum of vitextrifolin D (4)
35
S33.1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin E (5)
zmj-72 zmj-72
6.0
H-14
5.8
5.6
5.4
5.2
5.0
4.6
H-16
4.8
4.4
4.2
4.0
3.8
3.6
3.4 3.2 f1 (ppm)
3.0
H-11
2.8
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
36
S34. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin E (5)
zmj-72 zmj-72
210
200
190
180
170
160
150
140
130
120
110 f1 (ppm)
100
90
80
C
70
60
50
40
30
20
10
37
S35. 1H-1H COSY spectrum of vitextrifolin E (5) in CDCl3
zmj-72 zmj-72 cosy
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
38
S36. HSQC spectrum of vitextrifolin E (5) in CDCl3
zmj-72 zmj-72 hsqc
6.0
5.5
5.0
4.5
4.0
3.5
3.0 f2 (ppm)
2.5
2.0
1.5
1.0
0.5
0
10
20
30
40
50
60
70
80
90
100
110
120
130
39
S37. HMBC spectrum of vitextrifolin E (5) in CDCl3
zmj-72 zmj-72 hmbc
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
20
40
60
80
100
120
140
160
180
200
40
S38. NOESY spectrum of vitextrifolin E (5) in CDCl3
zmj-72 zmj-72 noesy
6.0
5.5
5.0
4.5
4.0
3.5 f2 (ppm)
3.0
2.5
2.0
1.5
1.0
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
41
S39. HRESIMS spectrum of vitextrifolin E (5)
42
S40. IR (KBr disc) spectrum of vitextrifolin E (5)
43
S41. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin F (6)
44
S42. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin F (6)
45
S43. 1H-1H COSY spectrum of vitextrifolin F (6) in CDCl3
46
S44. HSQC spectrum of vitextrifolin F (6) in CDCl3
47
S45. HMBC spectrum of vitextrifolin F (6) in CDCl3
48
S46. NOESY spectrum of vitextrifolin F (6) in CDCl3
49
S47. HRESIMS spectrum of vitextrifolin F (6)
50
S48. IR (KBr disc) spectrum of vitextrifolin F (6)
51
S49. 1H NMR (600 MHz, CDCl3) spectrum of vitextrifolin G (7)
52
S50. 13C NMR (150 MHz, CDCl3) spectrum of vitextrifolin G (7)
53
S51. 1H-1H COSY spectrum of vitextrifolin G (7) in CDCl3
54
S52. HSQC spectrum of vitextrifolin G (7) in CDCl3
55
S53. HMBC spectrum of vitextrifolin G (7) in CDCl3
56
S54. NOESY spectrum of vitextrifolin G (7) in CDCl3
57
S55. HRESIMS spectrum of vitextrifolin G (7)
58
S56. IR (KBr disc) spectrum of vitextrifolin G (7)
59
