Curare Alkaloids: Constituents of a Matis Dart Poison
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1 Supporting information Curare Alkaloids: Constituents of a Matis Dart Poison Gonzalo R. Malca Garcia, Lothar Hennig, Irina V. Shelukhina, Denis S. Kudryavtsev, Rainer W. Bussmann, Victor I. Tsetlin,*, and Athanassios Giannis *, Institut für Organische Chemie, Fakultät für Chemie und Mineralogie, Universität Leipzig, Johannisallee 29, Leipzig, Tel./Fax: +49(0) / +49(0) , Germany Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Department of Molecular Basis of Neurosignaling, Miklukho-Maklaya Street, 16/10, Moscow, Tel./Fax: (007) , Russia William L. Brown Center, Missouri Botanical Garden, P.O. Box 299, St. Louis, MO , Tel. (314) , USA giannis@uni-leipzig.de; vits@mx.ibch.ru 1
2 Table of Contents S1. Matis weapon. 6 S2. Crude poison. 7 S3. General scheme of the BBIQA s extraction S4. Fractionation results. 9 S5. Figures A and B S6. The structure of the new BBIQA s (1-5, d-tubocurarine). 11 S7. Comparison with SciFinder data base results 12 S8. 1 H NMR (400 MHz) spectrum of BBIQA 1 in methanol-d S9. 13 C NMR (100 MHz) spectrum of BBIQA 1 in methanol-d S10. APT spectrum of BBIQA 1 in methanol-d 4 15 S11. COSY spectrum of BBIQA 1 in methanol-d 4 16 S12. HSQC spectrum of BBIQA 1 in methanol-d S13. HMBC spectrum of BBIQA 1 in methanol-d 4 18 S14. NOESY spectrum of BBIQA 1 in methanol-d S15. HR-MS spectrum of BBIQA 1 20 S16. 1 H NMR (400 MHz) spectrum of BBIQA 2 in methanol-d
3 S C NMR (100 MHz) spectrum of BBIQA 2 in methanol-d S18. APT spectrum of BBIQA 2 in methanol-d S19. COSY spectrum of BBIQA 2 in methanol-d S20. HSQC spectrum of BBIQA 2 in methanol-d S21. HMBC spectrum of BBIQA 2 in methanol-d S22. HR-MS spectrum of BBIQA 2 27 S23. 1 H NMR (400 MHz) spectrum of BBIQA 3 in methanol-d S C NMR (100 MHz) spectrum of BBIQA 3 in methanol-d S25. APT spectrum of BBIQA 3 in methanol-d S26. COSY spectrum of BBIQA 3 in methanol-d 4 31 S27. HSQC spectrum of BBIQA 3 in methanol-d 4 32 S28. HMBC spectrum of BBIQA 3 in methanol-d 4 33 S29. NOESY spectrum of BBIQA 3 in methanol-d S30. HR-MS spectrum of BBIQA S31. 1 H NMR (400 MHz) spectrum of BBIQA 4 in methanol-d S C NMR (100 MHz) spectrum of BBIQA 4 in methanol-d S33. APT spectrum of BBIQA4 in methanol-d
4 S34. COSY spectrum of BBIQA 4 in methanol-d 4 39 S35. HSQC spectrum of BBIQA 4 in methanol-d 4 40 S36. HMBC spectrum of BBIQA 4 in methanol-d 4 41 S37. NOESY spectrum of BBIQA 4 in methanol-d S38. HR-MS spectrum of BBIQA S39. 1 H NMR (400 MHz) spectrum of BBIQA 5 in methanol-d S C NMR (100 MHz) spectrum of BBIQA 5 in methanol-d S41. APT spectrum of BBIQA 5 in methanol-d S42. COSY spectrum of BBIQA 5 in methanol-d S43. HSQC spectrum of BBIQA 5 in methanol-d 4 48 S44. HMBC spectrum of BBIQA 5 in methanol-d 4 49 S45. NOESY spectrum of BBIQA 5 in methanol-d S46. HR-MS spectrum of BBIQA S47. 1 H NMR (400 MHz) spectrum of d-tubocurarine in methanol-d S C NMR (400 MHz) spectrum of d-tubocurarine in methanol-d 4 53 S49. APT spectrum of d-tubocurarine in methanol-d 4 54 S50. COSY spectrum of d-tubocurarine in methanol-d
5 S51. HSQC spectrum of d-tubocurarine in methanol-d 4 56 S52. HMBC spectrum of d-tubocurarine in methanol-d S53. NOESY spectrum of d-tubocurarine in methanol-d S54. HR-MS spectrum of d-tubocurarine.. 59 S55. ECD spectrum
6 S1. Matis weapon 6
7 S2. Crude poison 7
8 S3. General scheme of the BBIQA s extraction 8
9 S4. Fractionation results Dried poison Fractions (mg)* weigh (g) A B C *All undissolved material was removed by filtration after solution in 2% aqueous acetic acid. 9
10 S5. Figures A and B Figure A. Diethyl ether extraction from 2% aqueous HOAc Figure B. BBIQA`s dried (Fraction C, rich in BBIQA`s). solution (brown color rich in BBIQA`s). 10
11 S6. Structure of the new BBIQA`s (1-5, d-tubocurarine) 11
12 S7. Comparison with SciFinder data base results C 34H 36N 2O 6 1 C 36H 38N 2O 6 2 C 34H 34N 2O 6 3 C 36H 36N 2O 7 4 C 37H 38N 2O 7 5 Characteristics Characteristics Characteristics Characteristics Characteristics Seco form Cyclic form Cyclic form Cyclic form Cyclic form N-unsubstituted N,N-dimethylsubstituted N-unsubstituted N - acetylated, N- unsubstituted N - acetylated, N- methylsubstituted 2x-OCH 3 2x-OCH 3 2x-OCH 3 2x-OCH 3 2x-OCH 3 11 aromatic CH 10 aromatic CH 9 aromatic CH 10 aromatic CH 10 aromatic CH 3x OH 2x OH 3x OH 3x OH 3x OH Same molecular formula: 472 CAS numbers (10/05/2015) Containing 3 BBIQA derivatives Same molecular formula: 345 CAS numbers (10/05/2015) Containing 74 BBIQA derivatives Same molecular formula: 335 CAS numbers (10/05/2015) Containing 10 BBIQA derivatives Same molecular formula: 120 CAS numbers (10/05/2015) Containing 3 BBIQA derivatives Same molecular formula: 114 CAS numbers (10/05/2015) Containing 11 BBIQA derivatives Seco form Cyclic form Cyclic form Cyclic form Cyclic form N-unsubstituted N,N-dimethylsubstituted N-unsubstituted N-methylsubstituted, N- unsubstituted N-Oxygen, N- methylsubstituted 2x-OCH 3 2x-OCH 3 2x-OCH 3 3x-OCH 3 2x-OCH 3 11 aromatic CH 10 aromatic CH 9 aromatic CH 7 aromatic CH 10 aromatic CH 12
13 S8. 1 H NMR (400 MHz) spectrum of BBIQA 1 in methanol-d 4 13
14 S9. 13 C NMR (100 MHz) spectrum of BBIQA 1 in methanol-d 4 14
15 S10. APT spectrum of BBIQA 1 in methanol-d 4 15
16 S11. COSY spectrum of BBIQA 1 in methanol-d 4 16
17 S12. HSQC spectrum of BBIQA 1 in methanol-d 4 17
18 S13. HMBC spectrum of BBIQA 1 in methanol-d 4 18
19 S14. NOESY spectrum of BBIQA 1 in methanol-d 4 19
20 S15. HR-MS spectrum of BBIQA 1 20
21 S16. 1 H NMR (400 MHz) spectrum of BBIQA 2 in methanol-d 4 21
22 S C NMR (100 MHz) spectrum of BBIQA 2 in methanol-d 4 22
23 S18. APT spectrum of BBIQA 2 in methanol-d 4 23
24 S19. COSY spectrum of BBIQA 2 in methanol-d 4 24
25 S20. HSQC spectrum of BBIQA 2 in methanol-d 4 25
26 S21. HMBC spectrum of BBIQA 2 in methanol-d 4 26
27 S22. HR-MS spectrum of BBIQA 2 27
28 S23. 1 H NMR (400 MHz) spectrum of BBIQA 3 in methanol-d 4 28
29 S C NMR (100 MHz) spectrum of BBIQA 3 in methanol-d 4 29
30 S25. APT spectrum of BBIQA 3 in methanol-d 4 30
31 S26. COSY spectrum of BBIQA 3 in methanol-d 4 31
32 S27. HSQC spectrum of BBIQA 3 in methanol-d 4 32
33 S28. HMBC spectrum of BBIQA 3 in methanol-d 4 33
34 S29. NOESY spectrum of BBIQA 3 in methanol-d 4 34
35 S30. HR-MS spectrum of BBIQA 3 35
36 S31. 1 H NMR (400 MHz) spectrum of BBIQA 4 in methanol-d 4 36
37 S C NMR (100 MHz) spectrum of BBIQA 4 in methanol-d 4 37
38 S33. APT spectrum of BBIQA 4 in methanol-d 4 38
39 S34. COSY spectrum of BBIQA 4 in methanol-d 4 39
40 S35. HSQC spectrum of BBIQA 4 in methanol-d 4 40
41 S36. HMBC spectrum of BBIQA 4 in methanol-d 4 41
42 S37. NOESY spectrum of BBIQA 4 in methanol-d 4 42
43 S38. HR-MS spectrum of BBIQA 4 43
44 S39. 1 H NMR (400 MHz) spectrum of BBIQA 5 in methanol-d 4 44
45 S C NMR (100 MHz) spectrum of BBIQA 5 in methanol-d 4 45
46 S41. APT spectrum of BBIQA 5 in methanol-d 4 46
47 S42. COSY spectrum of BBIQA 5 in methanol-d 4 47
48 S43. HSQC spectrum of BBIQA 5 in methanol-d 4 48
49 S44. HMBC spectrum of BBIQA 5 in methanol-d 4 49
50 S45. NOESY spectrum of BBIQA 5 in methanol-d 4 50
51 S46. HR-MS spectrum of BBIQA 5 51
52 S47. 1 H NMR (400 MHz) spectrum of d-tubocurarine in methanol-d 4 52
53 S C NMR (400 MHz) spectrum of d-tubocurarine in methanol-d 4 53
54 S49. APT spectrum of d- Tubocurarine in methanol-d 4 54
55 S50. COSY spectrum of d-tubocurarine in methanol-d 4 55
56 S51. HSQC spectrum of d-tubocurarine in methanol-d 4 56
57 S52. HMBC spectrum of d-tubocurarine in methanol-d 4 57
58 S53. NOESY spectrum of d-tubocurarine in methanol-d 4 58
59 S54. HR-MS spectrum of d-tubocurarine 59
60 S55. ECD spectrum 3 60
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