LC-MS-Guided Isolation of Insulin Secretion-promoting. Monoterpenoid Carbazole Alkaloids from Murraya
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1 Supporting Information LC-MS-Guided Isolation of Insulin Secretion-promoting Monoterpenoid Carbazole Alkaloids from Murraya microphylla Xiao-Li Ma, Jun Li, Jiao Zheng, Xiao-Pan Gu, Daneel Ferreira, Jordan K. Zjawiony, Ming-Bo Zhao, Xiao-Yu Guo, Peng-Fei Tu, and Yong Jiang *, State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing , People s Republic of China Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing , People s Republic of China Department of BioMolecular Sciences, Division of Pharmacognosy, and Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, Mississippi , United States
2 *Corresponding author. Tel/Fax: List of Contents Table S1. X-ray Crystallographic Data of Microphyline A (1) a and Microphyline D (6) a Table S2. The corresponding relation between atom labels on the XRD structure and those assigned in Chart 1. Figure S1. The mass fragmentation patterns of 1 (A) and 6 (B). The neutral loss (136.0 Da) scanning (C) and UV spectrum (D) of 95% aqueous EtOH extract of the dried leaves and stems of Murraya microphylla. Figure S2. Comparison of the experimental ECD spectrum of 2 in MeOH (black) with the calculated ECD spectra of (1''R,4''S,5''R)-2 (blue) and (1''S,4''S,5''R)-2 (red). Figure S3. The key HMBC (arrows) and 1 H 1 H COSY (bold lines) correlations of 3/4, 9, and 10. Figure S4. Comparison of the experimental ECD spectrum of 3 in MeOH (black) with the calculated ECD spectra of (1''S,4''S,5''R)-3 (blue) and (1''R,4''S,5''R)-3 (red). Figure S5. Comparison of the experimental ECD spectrum of 4 in MeOH (black) with the calculated ECD spectra of (1''R,4''S,5''R)-4 (blue) and (1''S,4''S,5''R)-4 (red). Figure S6. Observed NOE correlations of 5 and 9. Figure S7. Comparison of the experimental ECD spectrum of 5 in MeOH (black) with the calculated ECD spectra of (1''S,4''S,5''R)-5 (blue) and (1''R,4''S,5''R)-5 (red). Figure S8. The chiral-phase HPLC separation (A) and comparison of the experimental ECD spectra of 7a and 7b in MeOH with the calculated ECD spectra for (4 S)-7a and (4 R)-7b (B). Figure S9. The chiral-phase HPLC separation (A) and the comparison of the experimental ECD spectra of 8a and 8b in MeOH with the calculated ECD spectra for (4 S)-8a and (4 R)-8b (B). Figure S10. Comparison of the experimental ECD spectrum of 9 in MeOH (black) with the calculated ECD spectra of (4''R)-9 (blue) and (4''S)-9 (red).
3 Figure S11. Comparison of the experimental ECD spectrum of 10 in MeOH (black) with the calculated ECD spectra of (3''S,4''S)-10 (blue) and (3''R,4''R)-10 (red). Figure S12. Comparison of the experimental ECD spectrum of 11 in MeOH (black) with the calculated ECD spectra of (3''S,4''S)-11 (blue) and (3''R,4''R)-11 (red). Figure S13. Comparison of the experimental ECD spectrum of 12 in MeOH (black) with the calculated ECD spectra of (3''S,4''S)-12 (blue) and (3''R,4''R)-12 (red). Figure S14. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 1 in acetone-d 6. Figure S15. 1 H 1 H COSY spectrum of 1 (in acetone-d 6 ). Figure S16. HSQC spectrum of 1 (in acetone-d 6 ). Figure S17. HMBC spectrum of 1 (in acetone-d 6 ). Figure S18. NOESY spectrum of 1 (in acetone-d 6 ). Figure S19. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 2 in acetone-d 6. Figure S20. 1 H 1 H COSY spectrum of 2 (in acetone-d 6 ). Figure S21. HSQC spectrum of 2 (in acetone-d 6 ). Figure S22. HMBC spectrum of 2 (in acetone-d 6 ). Figure S23. NOESY spectrum of 2 (in acetone-d 6 ). Figure S24. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 3 in acetone-d 6. Figure S25. 1 H 1 H COSY spectrum of 3 (in acetone-d 6 ). Figure S26. HSQC spectrum of 3 (in acetone-d 6 ). Figure S27. HMBC spectrum of 3 (in acetone-d 6 ). Figure S28. NOESY spectrum of 3 (in acetone-d 6 ). Figure S29. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 4 in acetone-d 6. Figure S30. 1 H 1 H COSY spectrum of 4 (in acetone-d 6 ). Figure S31. HSQC spectrum of 4 (in acetone-d 6 ). Figure S32. HMBC spectrum of 4 (in acetone-d 6 ). Figure S33. NOESY spectrum of 4 (in acetone-d 6 ). Figure S34. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 5 in acetone-d 6.
4 Figure S35. 1 H 1 H COSY spectrum of 5 (in acetone-d 6 ). Figure S36. HSQC spectrum of 5 (in acetone-d 6 ). Figure S37. HMBC spectrum of 5 (in acetone-d 6 ). Figure S38. NOESY spectrum of 5 (in acetone-d 6 ). Figure S39. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 6 in acetone-d 6. Figure S40. 1 H 1 H COSY spectrum of 6 (in acetone-d 6 ). Figure S41. HSQC spectrum of 6 (in acetone-d 6 ). Figure S42. HMBC spectrum of 6 (in acetone-d 6 ). Figure S43. NOESY spectrum of 6 (in acetone-d 6 ). Figure S44. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 7 in acetone-d 6. Figure S45. 1 H 1 H COSY spectrum of 7 (in acetone-d 6 ). Figure S46. HSQC spectrum of 7 (in acetone-d 6 ). Figure S47. HMBC spectrum of 7 (in acetone-d 6 ). Figure S48. NOESY spectrum of 7 (in acetone-d 6 ). Figure S49. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 8 in acetone-d 6. Figure S50. 1 H 1 H COSY spectrum of 8 (in acetone-d 6 ). Figure S51. HSQC spectrum of 8 (in acetone-d 6 ). Figure S52. HMBC spectrum of 8 (in acetone-d 6 ). Figure S53. NOESY spectrum of 8 (in acetone-d 6 ). Figure S54. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 9 in acetone-d 6. Figure S55. 1 H 1 H COSY spectrum of 9 (in acetone-d 6 ). Figure S56. HSQC spectrum of 9 (in acetone-d 6 ). Figure S57. HMBC spectrum of 9 (in acetone-d 6 ). Figure S58. NOESY spectrum of 9 (in acetone-d 6 ). Figure S59. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 10 in acetone-d 6. Figure S60. 1 H 1 H COSY spectrum of 10 (in acetone-d 6 ). Figure S61. HSQC spectrum of 10 (in acetone-d 6 ).
5 Figure S62. HMBC spectrum of 10 (in acetone-d 6 ). Figure S63. NOESY spectrum of 10 (in acetone-d 6 ). Figure S64. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 11 in acetone-d 6. Figure S65. 1 H 1 H COSY spectrum of 11 (in acetone-d 6 ). Figure S66. HSQC spectrum of 11 (in acetone-d 6 ). Figure S67. HMBC spectrum of 11 (in acetone-d 6 ). Figure S68. NOESY spectrum of 11 (in acetone-d 6 ). Figure S69. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 12 in acetone-d 6. Figure S70. 1 H 1 H COSY spectrum of 12 (in acetone-d 6 ). Figure S71. HSQC spectrum of 12 (in acetone-d 6 ). Figure S72. HMBC spectrum of 12 (in acetone-d 6 ). Figure S73. NOESY spectrum of 12 (in acetone-d 6 ). Figure S74. The MTT assay results of 1. Figure S75. The insulinotropic effect test of 1 in a dose dependent manner.
6 Table S1. X-ray Crystallographic Data of Microphyline A (1) a and Microphyline D (6) a Parameters Compound 1 Compound 6 Empirical formula C 29 H 35 NO 3 C 29 H 35 NO 3 Formula weight Temperature 120 K 120 K Wavelength Å Å Crystal system monoclinic orthorhombic Space group P2 1 Pbca Unit cell dimensions a = (7) Å, α = 90 a = (10), α = 90 b = (10) Å, β = b = (2) Å, β = 90 c = (15) Å, γ = 90 c = (2) Å, γ = 90 Volume (2) Å (8) Å 3 Z 2 8 Calculated density g/cm g/cm 3 Absorption coefficient mm mm -1 F (000) Crystal size mm mm 3 Theta range for data collection to to Index ranges -8 h 9, -12 k 12, -14 h 12, -22 k -18 l 18 21, -18 l 24 Reflections collected Independent reflections 4348 [R int = , R sigma = 4499 [R int = , R sigma = ] ] Data / restraints / parameters 4348 / 1 / / 0 / 306 Goodness of fit on F Final R indices [I 2σ(I)] R 1 = , wr 2 = R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = R 1 = , wr 2 = Largest diff. peak and hole 0.20/-0.22 e. Å /-0.36 e. Å 3 a Colorless crystals of 1/6 were obtained in acetone/h 2 O (10:1, v:v)
7 Table S2. The corresponding relationship between atom labels on the XRD structure and those assigned in Chart 1. Atom labels of 1 Atom labels of 6 in Chart 1 in the XRD structure in Chart 1 in the XRD structure C1 C1 C1 C1 C2 C2 C2 C2 C3 C3 C3 C3 C4 C4 C4 C4 C4a C4a C4a C4a C4b C4b C4b C4b C5 C5 C5 C5 C6 C6 C6 C6 C7 C7 C7 C7 C8 C8 C8 C8 C8a C8a C8a C8a C9a C9a C9a C9a O1' O1 O1' O1 C2' C3' C2' C3' C3' C2' C3' C2' C4' C1' C4' C1' C5' C4' C5' C4' C6' C5' C6' C5' C1'' C8' C1'' C11' C2'' C9' C2'' C10' C3'' C10' C3'' C9' C4'' C13' C4'' C8' C5'' C12' C5'' C13' C6'' C11' C6'' C12' C7'' C17' C7'' C14' C8'' C14' C8'' C15' C9'' C15' C9'' C16' C10'' C16' C10'' C17' OCH 3-6 O(2)C(7')H 3 OCH 3-6 O(2)C(7')H 3 OH-7 O(3)H O-7 O(3) N9 N9 N9 N9
8 Intensity, cps Intensity, cps Absorbance, mau 1.8e5 1.5e5 1.2e5 9.0e4 6.0e e m/z, Da 7.9e5 7.0e5 6.0e5 5.0e5 4.0e5 3.0e5 2.0e5 1.0e e5 2.4e5 2.0e5 1.6e5 1.2e5 8.0e4 4.0e4 0.0 H 3CO HO N H O A Da NL scanning of Da Intensity, cps m/z, Da UV spectrum of M. microphylla extract Time, min 7.0e4 6.0e4 5.0e4 4.0e4 3.0e4 2.0e4 1.0e4 0.0 H 3CO O N H O B Da C D Figure S1. The mass fragmentation patterns of 1 (A) and 6 (B). The NL (136.0 Da) scanning (C) and UV spectrum (D) of 95% aqueous EtOH extract of the dried leaves and stems of Murraya microphylla.
9 Figure S2. Comparison of the experimental ECD spectrum of 2 in MeOH (black) with the calculated ECD spectra of (1''R,4''S,5''R)-2 (blue) and (1''S,4''S,5''R)-2 (red).
10 H 3 CO H 3 CO HO N H O O N H O HO N H O 3/ Figure S3. The key HMBC (arrows) and 1 H 1 H COSY (bold lines) correlations of 3/4, 9, and 10.
11 Figure S4. Comparison of the experimental ECD spectrum of 3 in MeOH (black) with the calculated ECD spectra of (1''S,4''S,5''R)-3 (blue) and (1''R,4''S,5''R)-3 (red).
12 Figure S5. Comparison of the experimental ECD spectrum of 4 in MeOH (black) with the calculated ECD spectra of (1''R,4''S,5''R)-4 (blue) and (1''S,4''S,5''R)-4 (red)
13 5 9 Figure S6. Observed NOE correlations of 5 and 9.
14 Figure S7. Comparison of the experimental ECD spectrum of 5 in MeOH (black) with the calculated ECD spectra of (1''S,4''S,5''R)-5 (blue) and (1''R,4''S,5''R)-5 (red).
15 mau 100 7b a min A B Figure S8. The chiral-phase HPLC separation (A) and comparison of the experimental ECD spectra of 7a and 7b in MeOH with the calculated ECD spectra for (4 S)-7a and (4 R)-7b (B).
16 mau 8b a min A B Figure S9. The chiral-phase HPLC separation (A) and comparison of the experimental ECD spectra of 8a and 8b in MeOH with the calculated ECD spectra for (4 S)-8a and (4 R)-8b (B).
17 Figure S10. Comparison of the experimental ECD spectrum of 9 in MeOH (black) with the calculated ECD spectra of (4''R)-9 (blue) and (4''S)-9 (red).
18 Figure S11. Comparison of the experimental ECD spectrum of 10 in MeOH (black) with the calculated ECD spectra of (3''S,4''S)-10 (blue) and (3''R,4''R)-10 (red).
19 Figure S12. Comparison of the experimental ECD spectrum of 11 in MeOH (black) with the calculated ECD spectra of (3''S,4''S)-11 (blue) and (3''R,4''R)-11 (red).
20 Figure S13. Comparison of the experimental ECD spectrum of 12 in MeOH (black) with the calculated ECD spectra of (3''S,4''S)-12 (blue) and (3''R,4''R)-12 (red).
21 MC-b-1-c-2-b-H f1 (ppm) Figure S14. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 1 in acetone-d 6.
22 Figure S15. 1 H 1 H COSY spectrum of 1 (in acetone-d 6 ).
23 Figure S16. HSQC spectrum of 1 (in acetone-d 6 ). Figure S17. HMBC spectrum of 1 (in acetone-d 6 ).
24 Figure S18. NOESY spectrum of 1 (in acetone-d 6 ).
25 Figure S19. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 2 in acetone-d 6.
26 Figure S20. 1 H 1 H COSY spectrum of 2 (in acetone-d 6 ). Figure S21. HSQC spectrum of 2 (in acetone-d 6 ).
27 Figure S22. HMBC spectrum of 2 (in acetone-d 6 ). Figure S23. NOESY spectrum of 2 (in acetone-d 6 ).
28 Figure S24. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 3 in acetone-d 6.
29 Figure S25. 1 H 1 H COSY spectrum of 3 (in acetone-d 6 ).
30 Figure S26. HSQC spectrum of 3 (in acetone-d 6 ).
31 Figure S27. HMBC spectrum of 3 (in acetone-d 6 ).
32 Figure S28. NOESY spectrum of 3 (in acetone-d 6 ).
33 Figure S29. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 4 in acetone-d 6.
34 Figure S30. 1 H 1 H COSY spectrum of 4 (in acetone-d 6 ).
35 Figure S31. HSQC spectrum of 4 (in acetone-d 6 ). Figure S32. HMBC spectrum of 4 (in acetone-d 6 ).
36 Figure S33. NOESY spectrum of 4 (in acetone-d 6 ).
37 Figure S34. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 5 in acetone-d 6. Figure S35. 1 H 1 H COSY spectrum of 5 (in acetone-d 6 ).
38 Figure S36. HSQC spectrum of 5 (in acetone-d 6 ). Figure S37. HMBC spectrum of 5 (in acetone-d 6 ).
39 Figure S38. NOESY spectrum of 5 (in acetone-d 6 ).
40 Figure S39. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 6 in acetone-d 6.
41 Figure S40. 1 H 1 H COSY spectrum of 6 (in acetone-d 6 ). Figure S41. HSQC spectrum of 6 (in acetone-d 6 ).
42 Figure S42. HMBC spectrum of 6 (in acetone-d 6 ). Figure S43. NOESY spectrum of 6 (in acetone-d 6 ).
43
44 Figure S44. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 7 in acetone-d 6.
45 Figure S45. 1 H 1 H COSY spectrum of 7 (in acetone-d 6 ). Figure S46. HSQC spectrum of 7 (in acetone-d 6 ).
46 Figure S47. HMBC spectrum of 7 (in acetone-d 6 ).
47 Figure S48. NOESY spectrum of 7 (in acetone-d 6 ).
48 Figure S49. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 8 in acetone-d 6.
49 Figure S50. 1 H 1 H COSY spectrum of 8 (in acetone-d 6 ). Figure S51. HSQC spectrum of 8 (in acetone-d 6 ).
50
51 Figure S52. HMBC spectrum of 8 (in acetone-d 6 ). Figure S53. NOESY spectrum of 8 (in acetone-d 6 ).
52
53 Figure S54. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 9 in acetone-d 6.
54 Figure S55. 1 H 1 H COSY spectrum of 9 (in acetone-d 6 ).
55 Figure S56. HSQC spectrum of 9 (in acetone-d 6 ). Figure S57. HMBC spectrum of 9 (in acetone-d 6 ).
56 Figure S58. NOESY spectrum of 9 (in acetone-d 6 ).
57 Figure S59. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 10 in acetone-d 6.
58 Figure S60. 1 H 1 H COSY spectrum of 10 (in acetone-d 6 ).
59 Figure S61. HSQC spectrum of 10 (in acetone-d 6 ). Figure S62. HMBC spectrum of 10 (in acetone-d 6 ).
60 Figure S63. NOESY spectrum of 10 (in acetone-d 6 ).
61 Figure S64. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 11 in acetone-d 6.
62 Figure S65. 1 H 1 H COSY spectrum of 11 (in acetone-d 6 ).
63 Figure S66. HSQC spectrum of 11 (in acetone-d 6 ). Figure S67. HMBC spectrum of 11 (in acetone-d 6 ).
64 Figure S68. NOESY spectrum of 11 (in acetone-d 6 ).
65 Figure S69. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra of 12 in acetone-d 6.
66 Figure S70. 1 H 1 H COSY spectrum of 12 (in acetone-d 6 ). Figure S71. HSQC spectrum of 12 (in acetone-d 6 ).
67 Figure S72. HMBC spectrum of 12 (in acetone-d 6 ). Figure S73. NOESY spectrum of 12 (in acetone-d 6 ).
68 Figure S74. The MTT assay results of 1.
69 Figure S75. The insulinotropic effect test of 1 in a dose dependent manner.
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