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 116044, People s Republic of China The First Affiliated Hospital of Dalian Medical University, No.222 Zhongshan Road, Dalian 116011, People s Republic of China S1
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 1.... S5 Table S3. Crystal Data and Structure Refinement for Compound 2.... S6 Figure S4.The 1 H NMR (CDCl 3, 600 MHz) Spectrum of Compound 1.... S7 Figure S5.The 13 C NMR (CDCl 3, 150 MHz) Spectrum of Compound 1.... S7 Figure S6.The HSQC Spectrum of Compound 1.... S8 Figure S7. The HMBC Spectrum of Compound 1.... S8 Figure S8. The H- 1 H COSY Spectrum of Compound 1.... S9 Figure S9. The NOESY Spectrum of Compound 1.... S9 Figure S10. The HRESIMS of Compound 1.... S10 Figure S11. The 1 H NMR (CDCl 3, 600 MHz) Spectrum of Compound 2.... S11 Figure S12. The 13 C NMR (CDCl 3, 150 MHz) Spectrum of Compound 2.... S11 Figure S13. The HSQC Spectrum of Compound 2.... S12 Figure S14. The HMBC Spectrum of Compound 2.... S12 Figure S15. The 1 H- 1 H COSY Spectrum of Compound 2.... S13 Figure S16. The NOESY Spectrum of Compound 2.... S13 Figure S17. The HRESIMS of Compound 2.... S14 Check cif for compound 1... S15 Check cif for compound 2... S18 S2
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
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±2.4 30.3±3.1 RKO 36.5±1.3 30.7±1.9 H1299 33.8±4.4 25.3±2.5 IOSE-80 45.6±5.4 32.4±4.3 A2780 36.7±1.7 31.5±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
Table S2. Crystal Data and Structure Refinement for Compound 1. Identification code 11q_1 Empirical formula C 29H 44O 2 Formula weight 424.64 Temperature/K 99.98(10) Crystal system monoclinic Space group C2 a/å 19.56339(13) b/å 7.68013(7) c/å 16.52524(11) α/ 90 β/ 93.4366(6) γ/ 90 Volume/Å 3 2478.44(3) Z 4 ρ calcg/cm 3 1.138 μ/mm -1 0.524 F(000) 936.0 Crystal size/mm 3 0.11 0.1 0.08 Radiation CuKα (λ = 1.54184) 2Θ range for data collection/ 5.358 to 147.28 Index ranges -24 h 22, -9 k 8, -20 l 20 Reflections collected 25397 Independent reflections 4713 [R int = 0.0399, R sigma = 0.0240] Data/restraints/parameters 4713/1/299 Goodness-of-fit on F 2 1.066 Final R indexes [I>=2σ (I)] R 1 = 0.0379, wr 2 = 0.1036 Final R indexes [all data] R 1 = 0.0393, wr 2 = 0.1042 Largest diff. peak/hole / e Å -3 0.25/-0.28 Flack/Hooft parameter 0.08(10)/0.05(7) S5
Table S3. Crystal Data and Structure Refinement for Compound 2. Identification code 11q_2 Empirical formula C 29H 44O 2 Formula weight 424.64 Temperature/K 100.00(10) Crystal system orthorhombic Space group P2 12 12 1 a/å 8.79462(16) b/å 14.7893(2) c/å 19.5287(3) α/ 90 β/ 90 γ/ 90 Volume/Å 3 2540.03(7) Z 4 ρ calcg/cm 3 1.110 μ/mm -1 0.511 F(000) 936.0 Crystal size/mm 3 0.14 0.12 0.11 Radiation CuKα (λ = 1.54184) 2Θ range for data collection/ 7.498 to 147.202 Index ranges -10 h 9, -17 k 18, -24 l 23 Reflections collected 16445 Independent reflections 5024 [R int = 0.0334, R sigma = 0.0301] Data/restraints/parameters 5024/0/289 Goodness-of-fit on F 2 1.071 Final R indexes [I>=2σ (I)] R 1 = 0.0456, wr 2 = 0.1197 Final R indexes [all data] R 1 = 0.0484, wr 2 = 0.1217 Largest diff. peak/hole / e Å -3 0.28/-0.22 Flack/Hooft parameter -0.01(13)/-0.07(10) S6
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
Figure S6.The HSQC Spectrum of Compound 1. Figure S7. The HMBC Spectrum of Compound 1. S8
Figure S8. The H- 1 H COSY Spectrum of Compound 1. Figure S9. The NOESY Spectrum of Compound 1. S9
Figure S10. The HRESIMS of Compound 1. S10
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
Figure S13. The HSQC Spectrum of Compound 2. Figure S14. The HMBC Spectrum of Compound 2. S12
Figure S15. The 1 H- 1 H COSY Spectrum of Compound 2. Figure S16. The NOESY Spectrum of Compound 2. S13
Figure S17. The HRESIMS of Compound 2. S14
Check cif for compound 1 S15
Check cif for compound 1 S16
Check cif for compound 1 S17
Check cif for compound 2 S18
Check cif for compound 2 S19
Check cif for compound 2 S20