Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2017

Grandiflodines A and B, two novel diterpenoid alkaloids from

Delphinium grandiflorum

Neng-Hua Chen,ab Yu-Bo Zhang,ab Wen Li, ab Pan Li,ab Li-Feng Chen,ab Yao-Lan Li,ab

Guo-Qiang Li, c* and Guo-Cai Wangab*

a Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, , 510632, P. R.

b Province Key Laboratory of Pharmacodynamic Constituents of TCM and New

Drugs Research, Jinan University, Guangzhou 510632, P. R. China

c University, Foshan, 528000, China

* Corresponding authors: E-mail: [email protected] (G. C. Wang), [email protected] (G. Q. Li) Contents

Figure S1. The HR-ESI-MS of compound 1 ...... 1

Figure S2. The UV of compound 1 in MeOH ...... 1

Figure S3. The IR (KBr disc) of compound 1 ...... 2

1 Figure S4. The H NMR spectrum of compound 1 in DMSO-d6 ...... 2

13 Figure S5. The C NMR spectrum of compound 1 in DMSO-d6 ...... 3

Figure S6. The DEPT-135 NMR spectrum of compound 1 in DMSO-d6 ...... 3

1 1 Figure S7. The H- H COSY spectrum of compound 1 in DMSO-d6 ...... 4

Figure S8. The HSQC spectrum of compound 1 in DMSO-d6...... 4

Figure S9. The HMBC spectrum of compound 1 in DMSO-d6...... 5

Figure S10. The NOESY spectrum of compound 1 in DMSO-d6 ...... 5

Figure S11. The HR-ESI-MS of compound 2 ...... 6

Figure S12. The UV of compound 2 in MeOH ...... 6

Figure S13. The IR (KBr disc) of compound 2 ...... 7

1 Figure S14. The H NMR spectrum of compound 2 in CDCl3...... 7

13 Figure S15. The C NMR spectrum of compound 2 in CDCl3...... 8

Figure S16. The DEPT-135 NMR spectrum of compound 2 in CDCl3...... 8

1 1 Figure S17. The H- H COSY spectrum of compound 2 in CDCl3...... 9

Figure S18. The HSQC NMR spectrum of compound 2 in CDCl3 ...... 9

Figure S19. The HMBC spectrum of compound 2 in CDCl3 ...... 10

Figure S20. The NOESY spectrum of compound 2 in CDCl3...... 10 Figure S1. The HR-ESI-MS of compound 1

Figure S2. The UV of compound 1 in MeOH

1 Figure S3. The IR (KBr disc) of compound 1

1 Figure S4. The H NMR spectrum of compound 1 in DMSO-d6

2 13 Figure S5. The C NMR spectrum of compound 1 in DMSO-d6

Figure S6. The DEPT-135 NMR spectrum of compound 1 in DMSO-d6

3 1 1 Figure S7. The H- H COSY spectrum of compound 1 in DMSO-d6

Figure S8. The HSQC spectrum of compound 1 in DMSO-d6

4 Figure S9. The HMBC spectrum of compound 1 in DMSO-d6

Figure S10. The NOESY spectrum of compound 1 in DMSO-d6

5 Figure S11. The HR-ESI-MS of compound 2

Figure S12. The UV of compound 2 in MeOH

6 Figure S13. The IR (KBr disc) of compound 2

1 Figure S14. The H NMR spectrum of compound 2 in CDCl3

7 13 Figure S15. The C NMR spectrum of compound 2 in CDCl3

Figure S16. The DEPT-135 NMR spectrum of compound 2 in CDCl3

8 1 1 Figure S17. The H- H COSY spectrum of compound 2 in CDCl3

Figure S18. The HSQC NMR spectrum of compound 2 in CDCl3

9 Figure S19. The HMBC spectrum of compound 2 in CDCl3

Figure S20. The NOESY spectrum of compound 2 in CDCl3

10