The Sponge-Derived Fijianolide Polyketide Class: Further Evaluation of Their Structural and Cytotoxicity Properties
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1 The Sponge-Derived Fijianolide Polyketide Class: Further Evaluation of Their Structural and Cytotoxicity Properties Tyler A. Johnson, Karen Tenney, Robert H. Cichewicz, Brandon I. Morinaka, Kimberly N. White, Taro Amagata, Balanehru Subramanian, Joseph Media, Susan L. Mooberry, Frederick A. Valeriote and Phillip Crews. *, [Supporting Information] Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California, Santa Cruz, California 95064, Josephine Ford Cancer Center, Henry Ford Health System, Detroit, Michigan 48202, and Southwest Foundation for Biomedical Research, San Antonio, Texas [Contents] Chart S1. Isolation scheme Table S1. Summary of Cacospongia mycofijiensis type natural products studied by others Table S2. 1 H and 13 C NMR data of 1 in C 6 D 6. Table S3. 1 H and 13 C NMR data of 2 in C 6 D 6 Table S4. 1 H, 13 C, COSY and HMBC NMR data of 7 in C 6 D 6 and CDCl 3 Table S5. 1 H and 13 C NMR data of 8 in C 6 D 6 Table S6. 1 H, 13 C, COSY and HMBC NMR data of 9 in C 6 D 6 and acetone d 6 Table S7. 1 H, 13 C, COSY and HMBC NMR data of 10 in C 6 D 6 Table S8. 1 H, 13 C, and COSY NMR data of 11 in C 6 D 6 Table S9. 1 H, 13 C, and COSY NMR data of 12 in C 6 D 6 Table S10. NOE Enhancements observed for H-23, H-26 and H-27 of Fijianolide G (10) in C 6 D 6 Table S11. Cytotoxicity in zone units of the fijianolides from the disk diffusion soft agar colony formation assay Figure S1. Selected examples of cytotoxic marine-derived polyketides Figure S2. 1 H NMR spectrum of Fijianolide A (1), (500 MHz, C 6 D 6 ) Figure S3. 13 C NMR spectrum of Fijianolide A (1), (125 MHz, C 6 D 6 ) Figure S4. 1 H NMR spectrum of Fijianolide B (2), (500 MHz, C 6 D 6 ) Figure S5. 13 C NMR spectrum of Fijianolide B (2), (125 MHz, C 6 D 6 ) Figure S6. 1 H NMR spectrum of Fijianolide D (7), (500 MHz, CDCl 3 ) Figure S7. 13 C NMR spectrum of Fijianolide D (7), (125 MHz, C 6 D 6 ) Figure S8. 1 H NMR spectrum of Fijianolide E (8), (500 MHz, C 6 D 6 ) Figure S9. 13 C NMR spectrum of Fijianolide E (8), (125 MHz, C 6 D 6 ) Figure S10. 1 H NMR spectrum of Fijianolide F (9), (500 MHz, C 6 D 6 ) Figure S C NMR spectrum of Fijianolide F (9), (125 MHz, C 6 D 6 ) Figure S12. 1 H NMR spectrum of Fijianolide G (10), (500 MHz, C 6 D 6 ) Figure S C NMR spectrum of Fijianolide G (10), (125 MHz, C 6 D 6 ) Figure S14. 1 H NMR spectrum of Fijianolide H (11), (500 MHz, C 6 D 6 ) Figure S C NMR spectrum of Fijianolide H (11), (125 MHz, C 6 D 6 ) Figure S16. 1 H NMR spectrum of Fijianolide I (12), (500 MHz, C 6 D 6 ) Figure S C NMR spectrum of Fijianolide I (12), (125 MHz, C 6 D 6 ) Figure S18. NOE enhancement of H-23 of 9 in benzene-d 6 at 600 MHz Figure S19. NOE enhancement of H-26 of 9 in benzene-d 6 at 600 MHz Figure S20. NOE enhancement of H-27 of 9 in benzene-d 6 at 600 MHz Figure S21. NOE enhancement of H-30 of 9 in benzene-d 6 at 600 MHz Figure S22. NOE enhancement of H-23 of 10 in benzene-d 6 at 600 MHz Figure S23. NOE enhancement of H-26 of 10 in benzene-d 6 at 600 MHz Figure S24. NOE enhancement of H-27 of 10 in benzene-d 6 at 600 MHz S1
2 Figure S25. Gradient LCMS chromatogram of 1 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. Figure S26. Gradient LCMS chromatogram of 2 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. Figure S27. Gradient LCMS chromatogram of 7 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. Figure S28. Gradient LCMS chromatogram of 8 using: 10:90 to 100 (50min) in CH 3 CN/H 2 O. Figure S29. Gradient LCMS chromatogram of 9 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. Figure S30. Gradient LCMS chromatogram of 10 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. Figure S31. Gradient LCMS chromatogram of 11 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. Figure S32. Gradient LCMS chromatogram of 12 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. S2
3 Chart S1. Isolation of the fijianolides, latrunculin A and mycothiazole S3
4 Table S1. Summary of Cacospongia mycofijiensis Type Natural Products Studied by Others Entry number Taxonomic identification Collection Site Major Constituents 1 unidentifiable (Bergquist) a American Samoa 1, 4, s3 2 Negombata magnifica b, c Djibouti 4, s4 3 N. magnifica d Egypt 4 4 Hyatella sp. (Bergquist) e Indonesia 1, 2, 4 5 N. magnifica d Israel s4 6 Fasciospongia rimosa (Hooper) f, g Japan 1, 2, s1, 3, 4 7 Cacospongia mycofijiensis h Marshall Islands 1, 2, 4 8 N. magnifica c Saudi Arabia 4 9 N. magnifica c Saudi Arabia s4 10 Dactylospongia sp. (Hooper) i Vanuatu 1, 2, s2, 4, 5 a Gulavita, N. L.; Gunasekera, S. P. and Pomponi, S. A. J. Nat. Prod. 1992, 55, 4, b Previously known as Latrunculia magnifica. c Ilan, M. Biol. Bull. 1995, 188: d Groweiss, A.; Shmeuli, U. Kashman, Y. Marine Toxins of Latrunculia magnifica. J. Org. Chem. 1983, 48, e Corley, D. G., Herb, R.; Moore, R. E.; Scheuer, P. J. J. Org. Chem. 1988, 53, f g Tanaka, J.; Higa, T.; Bernardineli, G.; Jefford, C. Chemistry. Lett. 1996, 255. Tanaka J., Higa, T. Tetrahedron Lett. 1996, 37, h Mooberry, S. L.; Tien, G.; Hernandez, A. H.; Plubrukarn, A.; Davidson, B. Cancer Research 1999, 59, i Cutignano, A.; Bruno, I.; Bifulco, G.; Casapullo, A.; Debitus, C.; Gomez- Paloma, L.; Riccio, R. Eur. J. Org. Chem. 2001, S4
5 Table S2. 1 H and 13 C NMR a data of 1 in C 6D 6 1 position H (J in HZ) C C mult C d (12.0) CH ddd (11.4, 9.6, 6.0) CH 4a 3.08 ddd (15.9, 10.8, 4.8) 36.1 CH 2 4b 2.28 m dddd (10.2, 7.2, 4.8, 3.0) 73.2 CH ddt (10.2, 2.4, 1.2) CH m CH 8a 1.81 dd (15.0, 9.6) 32.1 CH 2 8b 1.61 m tt (12.2, 2.4) 66.7 CH 10a 1.51 ddd (13.8, 9.6, 1.8) 43.0 CH 2 10b 0.93 ddd (13.8, 9.0, 1.8) ddd (14.4, 7.8, 6.6) 27.4 CH 12a 2.19 m 46.0 CH 2 12b 2.03 m C dd (15.6, 10.2) 35.8 CH ddd (6.6, 4.2, 1.2) 71.5 CH dd (4.8, 1.8) 75.5 CH ddd (10.2, 5.4, 4.8) 78.3 CH ddd (13.8, 7.8, 1.8) 35.2 CH ddd (3.9, 3.6, 1.2) 77.0 CH dd (6.0, 5.4) 82.0 CH ddd (15.6, 6.0, 1.8) CH ddd (15.6, 5.4, 1.8) CH dddd (11.4, 5.4, 4.8, 0.6) 73.5 CH 24a 2.01 m 36.1 CH 2 24b 1.66 dt (16.8, 3.0) C bs CH 27a 4.11 brs 65.7 CH 2 27b 4.04 brs d (6.6) 20.2 CH s, 4.89 s CH s 23.0 CH 3 a measured at 500 MHz ( 1 H) and 125 MHz ( 13 C) ` S5
6 Table S3. 1 H and 13 C NMR a data of 2 in C 6D 6 2 position H (J in HZ) C C mult C d (12.0) CH ddd (11.4, 9.6, 3.6) CH 4a 3.90 m 34.1 CH 2 4b 2.15 ddd (16.8, 6.6, 3.6) m 73.3 CH dq (10.2, 3.0) CH ddd (9.6, 4.8, 2.4) CH 8a 1.79 m 32.1 CH 2 8b 1.71 (17.8, 7.8, 4.2) dd (9.0, 3.0) 68.0 CH 10a 1.55 dd (14.4, 8.4) 44.0 CH 2 10b 1.19 ddd (14.4, 4.2, 3.0) m 30.0 CH 2.60 dd (13.2, 4.8) 12a 46.0 CH 2 12b 1.80 m C 14a 2.15 m 35.8 CH 2 14b 2.14 m m 67.6 CH dd (3.2, 2.8) 60.7 CH ddd (9.0, 3.6, 2.4) 51.6 CH 18a 2.22 ddd (13.8, 3.0, 1.2) 33.7 CH 2 18b 1.48 ddd (14.4, 8.4, 3.6) ddd (9.6, 5.4, 1.8) 72.7 CH m 73.4 CH ddd (16.2, 5.4, 1.8) CH ddd (15.6, 4.8, 1.2) CH m 73.4 CH 24a 1.95 m 36.1 CH 2 24b 1.62 m C brs CH 27a 4.11 brs 65.8 CH 2 27b 4.04 brs d (6.6) 21.1 CH s, 4.89 s CH s 23.0 CH 3 a measured at 500 MHz ( 1 H) and 125 MHz ( 13 C) S6
7 Table S4. 1 H and 13 C NMR a data of 7 in C 6D 6 and CDCl 3 b 7 position H (J in HZ) b C C mult. COSY HMBC C d (11.5) CH ddd (10.5,10.0, 7.0) CH 2, 4a 4a 3.16 ddd (11.0, 11.0,4.5) 35.8 CH 2 3, 5 2, 3, 5, 6 4b 2.51 ddd (11.0, 10.5, 7.0) m 73.3 CH ddd (10.5, 4.5, 3.0) CH ddd (10.5, 5.0, 2.5) CH 6, 8 6, 8 8a 2.00 dd (14.0, 9.0) 32.1 CH 2 7, 9 8b 1.95 ddd (11.0, 6.0, 2.5) m 66.7 CH 8, a 1.51 ddd (13.5, 9.5, 2.0) 42.9 CH 2 9, 11 9, 11, 12 10b 1.15 ddd (14.0, 10.0, 2.5) m 27.3 CH 10, 28 12a 2.11 dd (13.5, 6.5) 45.9 CH 2 12b 1.95 m C (H14a,b, H18a,18b, H24a,b)* 35.1 CH ddd (9.5, 2.5, 2.5) 71.4 CH 14, m 76.1 CH 15, 17 15, ddd (10.5, 5.0, 5.0) 78.4 CH 16, (H14a,b, H18a,18b, H24a,b)* 34.2 CH 2 17, 19 19, dd (3.5, 3.5) 76.8 CH 18, dd (4.5, 4.5) 81.4 CH 19, ddd (16.0, 5.0, 1.0) CH 20, 22 20, ddd (15.5, 6.0, 1.5) 130 CH 21, 23 20, ddd (10.5, 5.5, 5.0) 75.7 CH 22, 24 24, (H14a,b, H18a,18b, H24a,b)* 36.2 CH , C s CH C d (6.5) 20.1 CH , 11, s CH 2 12, s 22.2 CH 3 24, 25, 26 a measured at 500 MHz ( 1 H) and 125 MHz ( 13 C) b sample run in CDCl 3 * can be interchanged ` S7
8 Table S5. 1 H and 13 C NMR a data of 8 in C 6D 6 8 position H (J in Hz) b C C mult C d (11.5) CH ddd (11.0,10.5, 2.5) CH 4a 3.90 m 34.1 CH 2 4b 2.02 m m 73.3 CH brd (10.5) CH brd (10.5) CH 8a 1.79 m 32.1 CH 2 8b 1.67 m ddd (8.5, 5.0, 4.0) 68.1 CH 10a 1.50 brd (17.0) 44.0 CH 2 10b 1.20 ddd (16.0, 4.5, 3.5) m 30.0 CH 12a 2.60 dd (13.0, 4.5) 46.4 CH 2 12b 1.85 dd (13.0, 10.0) C brs 37.6 CH m 67.4 CH dd (2.0, 2.0) 60.8 CH brd (10.5) 52.1 CH 18a 2.16 m 34.2 CH2 18b 1.40 m ddd (11.0, 6.0, 1.0) 72.4 CH brd (9.0) 72.5 CH m CH m CH brdd (14.0, 3.0) 75.7 CH 24b 1.60 m 34.4 CH 2 24a 1.25 m C s CH C d (6.5) 20.1 CH brs, 4.96 brs CH s 22.2 CH 3 a measured at 500 MHz ( 1 H) and 125 MHz ( 13 C) S8
9 Table S6. 1 H and 13 C NMR a data of 9 in C 6D 6 and acetone d 6 b 9 position H (J in Hz) C C mult. COSY HMBC b C d (11.5) CH ddd (11.5,10.5, 7.0) CH 2, 4a 1 4a 3.05 ddd (14.0, 10.5, 5.0) 35.7 CH 2 3, 5 2, 3, 5 4b 2.15 ddd (14.0, 11.5, 6.5) m 73.2 CH dd (10.0, 2.5) CH ddd (10.5, 7.5, 2.5) CH 6, 8 6, 8 8a 1.84 ddd (12.5, 10.0, 2.5) 32.1 CH 2 7, 9 8b 1.60 dd (14.0, 2.5) dq (10.0, 2.4) 66.7 CH 8, a 1.55 dt (14.0, 9.5) 42.9 CH 2 9, 11 9, 11, 12 10b 0.93 ddd (13.5, 8.5, 2.0) m 27.3 CH 10, 28 12a 2.11 dd (14.0, 7.5) 45.9 CH 2 12b 2.05 m C m 35.7 CH ddd (9.5, 3.5, 2.5) 71.4 CH 14, dd (5.0, 2.5) 75.7 CH 15, 17 15, ddd (11.5, 6.0, 2.0) 78.3 CH 16, m 35.3 CH 2 17, 19 19, dt (4.0, 4.0) 76.9 CH 18, dd (4.0, 3.5) 81.7 CH 19, dd (13.0, 4.0) CH 20, 22 20, dd (14.5, 4.5) CH 21 20, dddd (11.4, 3.6, 2.8, 0.6) 64.6 CH 22, 24 24a 1.50 m 36.1 CH b 1.39 dd (14.5, 11.5) C d (4.2) 59.5 CH dd (12.0, 4.2) 88.5 CH 26, OH d (6.5) 20.1 CH , 11, s, 4.87 s CH 2 12, s 21.7 CH 3 24, 25, 26 OH 3.30 d (12.0) 27 a measured at 500 MHz ( 1 H) and 125 MHz ( 13 C) b sample run in acetone d 6 S9
10 Table S7. 1 H and 13 C NMR a data of 10 in C 6D 6 10 position H (J in Hz) C C mult. COSY HMBC C d (12.0) CH ddd (11.4,10.2, 3.6) CH 2, 4a 1 4a 3.92 m 34.1 CH 2 3, 5 2, 3, 5 4b 1.46 m m 73.1 CH brd (10.2) CH brd (10.2) CH 6, 8 6, 8 8a 1.81 m 32.1 CH 2 7, 9 8b 1.70 m m 68.0 CH 8, a 1.54 ddd (16.8, 9.0, 2.4) 43.9 CH 2 9, 11 9, 11, 12 10b 1.20 ddd (14.4, 4.8, 3.0) m 29.9 CH 10, 28 12a 2.61 dd (12.6, 6.0) 46.3 CH 2 12b 1.90 dd (13.2, 10.2) C 14a 2.16 dd (13.2, 3.6) 35.7 CH b 2.15 m m 67.5 CH 14, dd (2.4, 2.4) 60.7 CH 15, 17 15, ddd (9.0, 3.0, 1.2) 52.0 CH 16, 18 18a 2.05 ddd (10.2, 4.2, 1.2) 33.6 CH 2 17, 19 19, 20 18b 2.02 ddd (10.8, 3.6, 1.2) m 72.6 CH 18, brd (10.2) 73.3 CH 19, m CH 20, 22 20, m CH 21 20, m 64.4 CH 22, 24 24a 1.50 m 36.1 CH b 1.27 m C d (4.2) 59.5 CH d (4.2) 88.4 CH 26, OH d (6.6) 21.0 CH , 11, s, 4.92 s CH 2 12, s 21.7 CH 3 24, 26 OH 3.25 d (12.0) 27 a measured at 500 MHz ( 1 H) and 125 MHz ( 13 C) S10
11 Table S8. 1 H and 13 C NMR a data of 11 in C 6D 6 position H (J in Hz) C C mult. COSY C d (12.0) CH ddd (11.4,10.8, 7.2) CH 2, 4a 4a 3.08 ddd (14.4, 10.2, 4.8) 35.8 CH 2 3, 5 4b 2.16 ddd (15.6, 11.4, 7.0) 3, m 73.2 CH 4, dt (10.8, 3.6) CH ddd (10.2, 6.0, 2.4) CH 6, 8 8a 1.78 ddd (16.8, 9.0, 4.2) 32.1 CH 2 9 8b 1.60 m dq (10.2, 1.8) 66.7 CH 8, 8 10a 1.57 m 42.8 CH b 0.92 ddd (14.4, 9.6, 1.8) m 27.4 CH 10, 28 12a 2.04 m 46.0 CH 2 12b 2.02 m C 14a 2.25 m 35.7 CH b 2.24 m ddd (9.0, 3.6, 2.4) 71.3 CH dd (4.8, 1.8) 75.4 CH 15, ddd (10.8, 3.6, 2.4) 78.2 CH 16, 18 18a 2.06 m 35.1 CH b 2.02 m dd (3.6, 3.6) 76.8 CH 18, dd (4.8,4.8) 81.9 CH 19, dd (15.0, 4.8) CH 20, dd (15.6, 4.8) CH dddd (12.0, 4.8, 2.4, 1.0) 66.6 CH 22, 24 24a 1.93 dd (15.0, 10.8) 36.1 CH b 1.45 m C brs CH 27, brs 96.8 CH 26, d (6.6) 20.2 CH brs, 4.87 brs CH s 22.5 CH 3 26, 27 OMe 3.34 s 54.9 CH 3 11 a measured at 500 MHz ( 1 H) and 125 MHz ( 13 C) S11
12 Table S9. 1 H and 13 C NMR a data of 12 in C 6D 6 12 position H (J in Hz) C C mult. COSY C d (12.0) CH ddd (12.0,10.5, 7.0) CH 2, 4a 4a 3.12 ddd (11.0, 5.0, 1.2) 35.8 CH 2 3, 5 4b 2.12 m 3, m 73.3 CH 4, ddd (10.5, 3.0, 1.5) CH dd (10.5, 5.5) CH 6, 8 8a 1.84 ddd (12.5, 9.5, 2.0) 32.1 CH 2 9 8b 1.50 m tt (10.0, 2.5) 66.8 CH 8, 8 10a 1.55 m 42.8 CH b 0.94 ddd (13.5, 9.0, 2.0) m 27.4 CH 10, 28 12a 2.15 m 46.0 CH 2 12b 2.05 m C 14a 2.35 m 35.7 CH b 2.34 m dt (9.5, 3.0) 71.5 CH dd (9.0, 6.5) 75.6 CH 15, ddd (10.5, 5.5, 5.1) 78.4 CH 16, 18 18a 2.15 m 35.1 CH b 2.02 m dt (4.5, 3.5) 77.0 CH 18, dd (4.5, 3.5) 82.0 CH 19, ddd (16.0, 5.5, 1.0) CH 20, ddd (15.5, 5.0, 1.0) CH dddd (10.7, 4.5, 2.0, 1.0) 66.6 CH 22, 24 24a 2.15 m 36.1 CH b 1.60 m C brs CH 27, brs 89.0 CH 26, d (6.0) 20.2 CH brs, 4.89 brs CH s 22.7 CH 3 26, 27 a measured at 500 MHz ( 1 H) and 125 MHz ( 13 C) S12
13 Table 10. 1D 1 H NMR Difference of NOE Enhancements a Observed for Fijianolide G (10) at H-23, b H-26, c H-27 d and CH 3-30 e in C 6 D 6. Expt H irrad NOE rel enhanc inten a A a 1.1 B C a Relative enhanced intensity data based on setting the height of the weakest difference NOE peak as 1. b Actual spectrum is shown in Figure S22. c Actual spectrum is shown in Figure S23. d Actual spectrum is shown in Figure S24. S13
14 Table S11. Cytotoxicity in zone units of the fijianolides in the disk diffusion soft agar colony formation assay a Compound Conc. Murine tumor cell lines Human tumor cell lines μg/disk L1210 C 38 H-116 H-125 CEM CFU-GM Fijianolide A Fijianolide B > Fijianolide D Fijianolide E Fijianolide F Fijianolide G Fijianolide H Fijianolide I a measured in zone units: 200 zone units = 6mm. Murine cell lines: L1210 (lymphocytic leukemia), C38 (colon adenocarcinoma), CFU(GM) (colony-forming unit-granulocyte macrophage; normal hematopoietic); Human cell lines: H116 (colon), H125 (lung), CEM (leukemia), CFU(GM) (colony-forming unit-granulocyte macrophage; normal hematopoietic). b Significant selectivity is defined by a difference of 250 zone units. S14
15 Figure S1. Selected examples of cytotoxic marine-derived polyketides. S15
16 Figure S2. 1 H NMR spectrum of fijianolide A (1), (500 MHz, C 6 D 6 ) S16
17 Figure S3. 13 C NMR spectrum of fijianolide A (1), (125 MHz, C 6 D 6 ) S17
18 Figure S4. 1 H NMR spectrum of fijianolide B (2), (500 MHz, C 6 D 6 ) S18
19 Figure S5. 13 C NMR spectrum of fijianolide B (2), (125 MHz, C 6 D 6 ) S19
20 Figure S6. 1 H NMR spectrum of fijianolide D (7), (500 MHz, CDCl Figure S ) C NMR spectrum of fijianolide B (2), (125 MHz, C 6 D 6 ) S20 19
21 Figure S7. 13 C NMR spectrum of fijianolide D (7), (125 MHz, C 6 D 6 ) S21 20
22 Figure S8. 1 H NMR spectrum of fijianolide E (8), (500 MHz, C 6 D 6 ) S22
23 Figure S9. 13 C NMR spectrum of fijianolide E (8), (125 MHz, C 6 D 6 ) S23 22
24 Figure S10. 1 H NMR spectrum of fijianolide F (9), (500 MHz, C 6 D 6 ) S24
25 Figure S C NMR spectrum of fijianolide F (9), (125 MHz, C 6 D 6 ) S25
26 Figure S12. 1 H NMR spectrum of fijianolide G (10), (500 MHz, C 6 D 6 ) S26
27 Figure S C NMR spectrum of fijianolide G (10), (125 MHz, C 6 D 6 ) S27
28 Figure S14. 1 H NMR spectrum of fijianolide H (11), (500 MHz, C 6 D 6 ) S28
29 Figure S C NMR spectrum of fijianolide H (11), (125 MHz, C 6 D 6 ) S29
30 Figure S16. 1 H NMR spectrum of fijianolide I (12), (500 MHz, C 6 D 6 ) S30
31 Figure S C NMR spectrum of fijianolide I (12), (125 MHz, C 6 D 6 ) S31
32 Figure S18. NOE enhancement of H-23 of 9 in benzene-d 6 at 600 MHz. S32
33 Figure S19. NOE enhancement of H-26 of 9 in benzene-d 6 at 600 MHz. S33
34 Figure S20. NOE enhancement of H-27 of 9 in benzene-d 6 at 600 MHz. S34
35 Figure S21. NOE enhancement of CH 3-30 of 9 in benzene-d 6 at 600 MHz. S35
36 Figure S22. NOE enhancement of H-23 of 10 in benzene-d 6 at 600 MHz. S36
37 Figure S23. NOE enhancement of H-26 of 10 in benzene-d 6 at 600 MHz. S37
38 Figure S24. NOE enhancement of H-27 of 10 in benzene-d 6 at 600 MHz. S38
39 Figure S25. Gradient LCMS chromatogram of 1 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. Figure S26. Gradient LCMS chromatogram of 2 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. S39
40 Figure S27. Gradient LCMS chromatogram of 7 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. Figure S28. Gradient LCMS chromatogram of 8 using: 10:90 to 100 (50min) in CH 3 CN/H 2 O. S40
41 Figure S29. Gradient LCMS chromatogram of 9 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. Figure S30. Gradient LCMS chromatogram of 10 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. S41
42 Figure S31. Gradient LCMS chromatogram of 11 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. Figure S32. Gradient LCMS chromatogram of 12 using: 30:70 to 80:20 (50min) in CH 3 CN/H 2 O. S42
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# School of Pharmaceutical Sciences, Zhengzhou University, 100 Kexue Avenue, Zhengzhou, Henan , China.
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