Supporting information. Imidazole Alkaloids and their Zinc Complexes from the Calcareous. Marine Sponge Leucetta chagosensis
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1 Supporting information Imidazole lkaloids and their Zinc Complexes from the Calcareous Marine Sponge Leucetta chagosensis Wei-ZhuoTang,, Zhong-Zhen Yang, Wei Wu, Jie Tang, Fan Sun, Shu-Ping Wang, Chun-Wei Cheng, Fan Yang, *, and Hou-Wen Lin*, Research Center for Marine rugs, State Key Laboratory of ncogenes and Related Genes, epartment of Pharmacy, Renji Hospital, School of Medicine, Shanghai Jiao Tong University, Shanghai 001, People s Republic of China College of Biological and Environmental Engineering, Changsha University, Changsha 100, People s Republic of China 1
2 Contents Photo of the Calcareous Marine Sponge Leucetta chagosensis (o. X106). Experimental Section Table S1. 1 H(600 Hz) and C(10 Hz) MR Spectroscopic ata of 6 and in CCl 3. Figure S1. The mass spectral fragmentation patterns of compounds 1() and (B) observed by tandem mass spectrometric. Figure S. etailed structures of Zn complexes of naamidine J () and pyronaamidine (). Figure S3. Structures for known compounds isolated from the marine sponge Leucetta chagosensis. Figure S. 1 H MR spectrum of new compound 1 in MS-d 6. Figure S. C MR spectrum of new compound 1 in MS-d 6. Figure S6. EPT spectrum of new compound 1 in MS-d 6. Figure S. HSQC spectrum of new compound 1 in MS-d 6. Figure S8. HMBC spectrum of new compound 1 in MS-d 6. Figure S9. 1 H- 1 H CSY spectrum of new compound 1 in MS-d 6.. Figure S10. ESY spectrum of new compound 1 in MS-d 6. Figure S. HRESIMS spectrum of new compound 1. Figure S1. UV spectrum of new compound 1 in MeH. Figure S. IR spectrum of new compound 1. Figure S1. 1 H MR spectrum of new compound in MS-d 6. Figure S1. C MR spectrum of new compound in MS-d 6. Figure S. EPT spectrum of new compound in MS-d 6. Figure S1. HSQC spectrum of new compound in MS-d 6. Figure S. HMBC spectrum of new compound in MS-d 6. Figure S19. 1 H- 1 H CSY spectrum of new compound in MS-d 6.. Figure S0. ESY spectrum of new compound in MS-d 6. Figure S1. HRESIMS spectrum of new compound. Figure S. UV spectrum of new compound in MeH. Figure S3. IR spectrum of new compound. Figure S. 1 H MR spectrum of new compound 3 in MS-d 6. Figure S. C MR spectrum of new compound 3 in MS-d 6. Figure S6. EPT spectrum of new compound 3 in MS-d 6. Figure S. HSQC spectrum of new compound 3 in MS-d 6. Figure S8. HMBC spectrum of new compound 3 in MS-d 6. Figure S9. 1 H- 1 H CSY spectrum of new compound 3 in MS-d 6.. Figure S30. ESY spectrum of new compound 3 in MS-d 6. Figure S31. HRESIMS spectrum of new compound 3. Figure S3. UV spectrum of new compound 3 in MeH. Figure S33. IR spectrum of new compound 3. Figure S3. 1 H MR spectrum of new compound in CCl 3. Figure S3. C MR spectrum of new compound in CCl 3. Figure S36. EPT spectrum of new compound in CCl 3.
3 Figure S3. HSQC spectrum of new compound in CCl 3. Figure S38. HMBC spectrum of new compound in CCl 3. Figure S39. 1 H- 1 H CSY spectrum of new compound in CCl 3. Figure S0. ESY spectrum of new compound in CCl 3. Figure S1. HRESIMS spectrum of new compound. Figure S. UV spectrum of new compound in MeH. Figure S3. IR spectrum of new compound. Figure S. 1 H MR spectrum of new compound in MS-d 6. Figure S. C MR spectrum of new compound in MS-d 6. Figure S6. EPT spectrum of new compound in MS-d 6. Figure S. HSQC spectrum of new compound in MS-d 6. Figure S8. HMBC spectrum of new compound in MS-d 6. Figure S9. 1 H- 1 H CSY spectrum of new compound in MS-d 6. Figure S0. ESY spectrum of new compound in MS-d 6. Figure S1. HRESIMS spectrum of new compound. Figure S. UV spectrum of new compound in MeH. Figure S3. IR spectrum of new compound. 3
4 Photo of the Calcareous Marine Sponge Leucetta chagosensis (o. X106).
5 Table S1. 1 H(600 Hz) and C(10 Hz) MR Spectroscopic ata of 6 and in CCl 3 6 position δ C, type δ H (J in Hz) δ C, type δ H (J in Hz)., C., C 1.0, C., C 6.0, C 1., C 6 9.3, CH 3.90, brs 9.9, CH 3.93, d (.6) 3., d (.6) 3.3, CH 3.89, brs 31.1, CH 3.86, d (1.0) 3.1, d (1.0) 9 1.6, C 1., C 1., C 1.3, C.3, C.8, C , CH 3 3.6, s 30., CH 3 3.6, s 1.8, CH 3.8, s., CH 3.9, s -CH 3 6.1, CH , s 6.1, CH 3 3.8, s 1-CH 3.9, CH , s 6.0, CH 3 3.3, s -CH 3., CH 3 3.6, s., CH 3 3., s , C 19., C 1., CH 6.1, d (1.0) 1.3, CH 6., d (1.8) 3.1, C., C 19., C 19., C 1., CH 6.3, d (8.) 1.6, CH 6., d (8.) , CH 6., dd (8.,1.0) 10.1,CH 6.61,dd (8., 1.8) 1 1.6, C 0.0, C 19., CH., d (8.3).8, CH 6.66, d (8.6) 3., CH 6.9, d (8.3) 3.6, CH 6.9, d (8.6).3, C., C., CH 6.9, d (8.3) 3.6, CH 6.9, d (8.6) 6 19., CH., d (8.3).8, CH 6.66, d (8.6)
6 Figure S1. The mass spectral fragmentation patterns of compounds 1() and (B) observed by tandem mass spectrometric. 6
7 Figure S. etailed structures of bis(naamidine J)zinc () and bis(pyronaamidine)zinc ().
8 Figure S3. Structures for known compounds isolated from the marine sponge Leucetta chagosensis. 8
9 Figure S. 1 H MR spectrum of new compound 1 in MS-d 6. H B C 9 Leuchagodine (1) 9
10 Figure S. C MR spectrum of new compound 1 in MS-d 6. H B C 9 Leuchagodine (1) 10
11 Figure S6. EPT spectrum of new compound 1 in MS-d 6. H B C 9 Leuchagodine (1)
12 Figure S. HSQC spectrum of new compound 1 in MS-d 6. H B C 9 Leuchagodine (1) 1
13 Figure S8. HMBC spectrum of new compound 1 in MS-d 6. H B C 9 Leuchagodine (1)
14 Figure S9. 1 H- 1 H CSY spectrum of new compound 1 in MS-d 6. H B C 9 Leuchagodine (1) 1
15 Figure S10. ESY spectrum of new compound 1 in MS-d 6. H B C 9 Leuchagodine (1) 1
16 H 0 10 B C Figure S. HRESI spectrum of new compound 1. Leuchagodine (1)
17 Figure S1. UV spectrum of new compound 1 in MeH. H B C 9 Leuchagodine (1) 1
18 Figure S. IR spectrum of new compound 1 in MeH. H B C 9 Leuchagodine (1)
19 Figure S1. 1 H MR spectrum of new compound in MS-d 6. 0 H H H B C 9 Leuchagodine B () 8 19
20 Figure S1. C MR spectrum of new compound in MS-d 6. 0 H H H B C 9 Leuchagodine B () 8 0
21 0 H H H B C 9 Leuchagodine B () 8 Figure S. EPT spectrum of new compound in MS-d 6. 1
22 0 H H H Leuchagodine B () 10 B C 9 8 Figure S1. HSQC spectrum of new compound in MS-d 6.
23 0 H H H Leuchagodine B () 10 B C 9 8 Figure S. HMBC spectrum of new compound in MS-d 6. 3
24 0 H H H Leuchagodine B () 10 B C 9 8 Figure S19. 1 H- 1 H CSY spectrum of new compound in MS-d 6.
25 0 H H H Leuchagodine B () 10 B C 9 8 Figure S0. ESY spectrum of new compound in MS-d 6.
26 Figure S1. HRESIMS spectrum of new compound. 0 H H H Leuchagodine B () 10 B C 9 8 6
27 0 H H H B C 9 Leuchagodine B () 8 Figure S. UV spectrum of new compound in MeH.
28 0 H H H Leuchagodine B () 10 B C 9 8 Figure S3. IR spectrum of new compound. 8
29 Figure S. 1 H MR spectrum of new compound 3 in MS-d 6. H 3' ' 1 ' 1 ' 6' 1' B C 1 Kealiinine (3) 9
30 Figure S. C MR spectrum of new compound 3 in MS-d 6. H 3' ' 1 ' 1 ' 6' 1' B C 1 Kealiinine (3) 30
31 Figure S6. EPT spectrum of new compound 3 in MS-d 6. H 3' ' 1 ' 1' 1 ' 6' B C Kealiinine (3) 31
32 Figure S. HSQC spectrum of new compound 3 in MS-d 6. H 3' ' 1 ' 1' 1 ' 6' B C Kealiinine (3) 3
33 Figure S8. HMBC spectrum of new compound 3 in MS-d 6. H 3' ' 1 ' 1' 1 ' 6' B C Kealiinine (3) 33
34 Figure S9. 1 H- 1 H CSY spectrum of new compound 3 in MS-d 6. H 3' ' 1 ' 1' 1 ' 6' B C Kealiinine (3) 3
35 H 3' ' 1 ' 1' 1 ' 6' B C Figure S30. ESY spectrum of new compound 3 in MS-d 6. Kealiinine (3) 3
36 H 3' ' 1 ' 1' 1 ' 6' B C Figure S31. HRESIMS spectrum of new compound 3. Kealiinine (3) 36
37 Figure S3. UV spectrum of new compound 3 in MeH. H 3' ' 1 ' 1 ' 6' 1' B C 1 Kealiinine (3) 3
38 Figure S33. IR spectrum of new compound 3. H 3' ' 1 ' 1 ' 6' 1' B C 1 Kealiinine (3) 38
39 Figure S3. 1 H MR spectrum of new compound in CCl 3. 1 ' 3' ' B 1 6' ' 1" Bis(naamidine J)znic () C " Zn + 39
40 Figure S3. C MR spectrum of new compound in CCl 3. 1 ' 3' ' B 1 6' ' 1" Bis(naamidine J)znic () C " Zn + 0
41 Figure S36. EPT spectrum of new compound in CCl 3. 1 ' 3' ' B 1 6' ' 1" Bis(naamidine J)znic () C " Zn + 1
42 Figure S3. HSQC spectrum of new compound in CCl 3. 1 ' 3' ' B 1 6' ' 1" Bis(naamidine J)znic () C " Zn +
43 Figure S38. HMBC spectrum of new compound in CCl 3. 1 ' 3' ' B 1 6' ' 1" Bis(naamidine J)znic () C " Zn + 3
44 Figure S39. 1 H- 1 HCSY spectrum of new compound in CCl 3. 1 ' 3' ' B 1 6' ' 1" C Bis(naamidine J)znic () " Zn +
45 Figure S0. ESY spectrum of new compound in CCl 3. 1 ' 3' ' B 1 6' ' 1" Bis(naamidine J)znic () C " Zn +
46 Figure S1. HRESIMS spectrum of new compound. 1 ' 3' ' B 1 6' ' 1" Bis(naamidine J)znic () C " Zn + 6
47 Figure S. UV spectrum of new compound in MeH. 1 ' 3' ' B 1 6' ' 1" Bis(naamidine J)znic () C " Zn +
48 Figure S3. IR spectrum of new compound. 1 ' 3' ' B 1 6' ' 1" Bis(naamidine J)znic () C " Zn + 8
49 Figure S. 1 H MR spectrum of new compound in MS-d ' H ' 3' B 1 6' ' 1" Bis(pyronaamidine)zinc () C " Zn + 9
50 Figure S. C MR spectrum of new compound in MS-d ' 6 H ' 3' B 1 6' ' 1" Bis(pyronaamidine)zinc () C " Zn + 0
51 Figure S6. EPT spectrum of new compound in MS-d ' 6 H ' 3' B 1 6' ' 1" Bis(pyronaamidine)zinc () C " Zn + 1
52 Figure S. HSQC spectrum of new compound in MS-d ' 6 H ' 3' B 6' 1 ' 1" Bis(pyronaamidine)zinc () C " Zn +
53 Figure S8. HMBC spectrum of new compound in MS-d ' 6 H ' 3' B 6' 1 ' 1" Bis(pyronaamidine)zinc () C " Zn + 3
54 Figure S9. 1 H- 1 H CSY spectrum of new compound in MS-d ' 6 H ' 3' B 1 6' ' 1" Bis(pyronaamidine)zinc () C " Zn +
55 Figure S0. ESY spectrum of new compound in MS-d ' 6 H ' 3' B 6' 1 ' 1" Bis(pyronaamidine)zinc () C " Zn +
56 Figure S1. HRESIMS spectrum of new compound ' H ' 3' B 1 6' ' 1" Bis(pyronaamidine)zinc () C " Zn + 6
57 Figure S. UV spectrum of new compound in MeH ' 6 H ' 3' B 6' 1 ' 1" C Bis(pyronaamidine)zinc () " Zn +
58 Figure S3. IR spectrum of new compound ' 6 H ' 3' B 1 6' ' 1" Bis(pyronaamidine)zinc () C " Zn + 8
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