Supporting Information

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1 Supporting Information Ebracpenes A and B, Unusual Ring C-seco and Ring D-aromatic Nor-triterpenoids from Euphorbia ebracteolata and Lipase Inhibitory Evaluation Chao Wang,,# Qingsong Yan,,# Yifei Wang,,# Shanshan Huang, Jing Ning, Lei Feng, Chengpeng Sun, Baojing Zhang, Dawei Li,*, and Xiaochi Ma*, College of Pharmacy, Academy of Integrative Medicine, and National-Local Joint Engineering Research Center for Drug Research and Development of Neurodegenerative Disease, Dalian Medical University, Dalian , People s Republic of China The First Affiliated Hospital of Dalian Medical University, No.222 Zhongshan Road, Dalian , People s Republic of China S1

2 Table of Contents Figure S1. The Structure of α-onocerin and 21α-hydroxyserrat-14-en-3β-yl p-dihydrocoumarate.... S3 Figure S2. 2D Docking Analysis of Compound 1 and Lipase.... S3 Figure S3. 2D Docking Analysis of Compound 2 and Lipase.... S4 Table S1. The Cytotoxicity of Compounds 1 and 2 against Various Cells (IC 50 μm)... S4 Table S2. Crystal Data and Structure Refinement for Compound S5 Table S3. Crystal Data and Structure Refinement for Compound S6 Figure S4.The 1 H NMR (CDCl 3, 600 MHz) Spectrum of Compound S7 Figure S5.The 13 C NMR (CDCl 3, 150 MHz) Spectrum of Compound S7 Figure S6.The HSQC Spectrum of Compound S8 Figure S7. The HMBC Spectrum of Compound S8 Figure S8. The H- 1 H COSY Spectrum of Compound S9 Figure S9. The NOESY Spectrum of Compound S9 Figure S10. The HRESIMS of Compound S10 Figure S11. The 1 H NMR (CDCl 3, 600 MHz) Spectrum of Compound S11 Figure S12. The 13 C NMR (CDCl 3, 150 MHz) Spectrum of Compound S11 Figure S13. The HSQC Spectrum of Compound S12 Figure S14. The HMBC Spectrum of Compound S12 Figure S15. The 1 H- 1 H COSY Spectrum of Compound S13 Figure S16. The NOESY Spectrum of Compound S13 Figure S17. The HRESIMS of Compound S14 Check cif for compound 1... S15 Check cif for compound 2... S18 S2

3 Figure S1. The Structure of α-onocerin and 21α-hydroxyserrat-14-en-3β-yl p-dihydrocoumarate. α-onocerin 21α-hydroxyserrat-14-en-3β-yl p-dihydrocoumarate Figure S2. 2D Docking Analysis of Compound 1 and Lipase. S3

4 Figure S3. 2D Docking Analysis of Compound 2 and Lipase. Table S1. The Cytotoxicity of Compounds 1 and 2 against Various Cells (IC50 μm) Cells Ebracpene A (1) Ebracpene B (2) CCD841 CoN 33.4± ±3.1 RKO 36.5± ±1.9 H ± ±2.5 IOSE ± ±4.3 A ± ±3.6 CCD 841 CoN: Homo sapiens colon normal cells RKO: Human colon cancer cells H1299: Human lung cancer cells IOSE-80: Human ovarian epithelial cells A2780: Human ovarian cancer cells S4

5 Table S2. Crystal Data and Structure Refinement for Compound 1. Identification code 11q_1 Empirical formula C 29H 44O 2 Formula weight Temperature/K 99.98(10) Crystal system monoclinic Space group C2 a/å (13) b/å (7) c/å (11) α/ 90 β/ (6) γ/ 90 Volume/Å (3) Z 4 ρ calcg/cm μ/mm F(000) Crystal size/mm Radiation CuKα (λ = ) 2Θ range for data collection/ to Index ranges -24 h 22, -9 k 8, -20 l 20 Reflections collected Independent reflections 4713 [R int = , R sigma = ] Data/restraints/parameters 4713/1/299 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = Largest diff. peak/hole / e Å /-0.28 Flack/Hooft parameter 0.08(10)/0.05(7) S5

6 Table S3. Crystal Data and Structure Refinement for Compound 2. Identification code 11q_2 Empirical formula C 29H 44O 2 Formula weight Temperature/K (10) Crystal system orthorhombic Space group P a/å (16) b/å (2) c/å (3) α/ 90 β/ 90 γ/ 90 Volume/Å (7) Z 4 ρ calcg/cm μ/mm F(000) Crystal size/mm Radiation CuKα (λ = ) 2Θ range for data collection/ to Index ranges -10 h 9, -17 k 18, -24 l 23 Reflections collected Independent reflections 5024 [R int = , R sigma = ] Data/restraints/parameters 5024/0/289 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = Largest diff. peak/hole / e Å /-0.22 Flack/Hooft parameter -0.01(13)/-0.07(10) S6

7 Figure S4.The 1 H NMR (CDCl3, 600 MHz) Spectrum of Compound 1. Figure S5.The 13 C NMR (CDCl3, 150 MHz) Spectrum of Compound 1. S7

8 Figure S6.The HSQC Spectrum of Compound 1. Figure S7. The HMBC Spectrum of Compound 1. S8

9 Figure S8. The H- 1 H COSY Spectrum of Compound 1. Figure S9. The NOESY Spectrum of Compound 1. S9

10 Figure S10. The HRESIMS of Compound 1. S10

11 Figure S11. The 1 H NMR (CDCl3, 600 MHz) Spectrum of Compound 2. Figure S12. The 13 C NMR (CDCl3, 150 MHz) Spectrum of Compound 2. S11

12 Figure S13. The HSQC Spectrum of Compound 2. Figure S14. The HMBC Spectrum of Compound 2. S12

13 Figure S15. The 1 H- 1 H COSY Spectrum of Compound 2. Figure S16. The NOESY Spectrum of Compound 2. S13

14 Figure S17. The HRESIMS of Compound 2. S14

15 Check cif for compound 1 S15

16 Check cif for compound 1 S16

17 Check cif for compound 1 S17

18 Check cif for compound 2 S18

19 Check cif for compound 2 S19

20 Check cif for compound 2 S20