Supporting Information Chalcones from Angelica keiskei: Evaluation of ...
Supporting Information
Chalcones from Angelica keiskei: Evaluation of Their Heat Shock Protein Inducing Activities
Yun-Seo Kil,† Seul-Ki Choi,† Yun-Sil Lee,† Mahtab Jafari,‡ and Eun-Kyoung Seo*,†
†
College of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University,
Seoul 120-750, Korea ‡
Department of Pharmaceutical Sciences, University of California, Irvine, California 92697,
United States
Figure S1. Figure S2. Figure S3. Figure S4. Figure S5. Figure S6. Figure S7. Figure S8. Figure S9. Figure S10. Figure S11.
1
H NMR spectrum (400 MHz, CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 13 C NMR spectrum (100 MHz, CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 1 H-1H COSY NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 1 H-1H NOESY NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 1 H-13C HSQC NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 1 H-13C HMBC NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 1 H NMR spectrum (400 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ........................... 13 C NMR spectrum (100 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ........................... 1 H-1H COSY NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ........................... 1 H-1H NOESY NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ........................... 1 H-13C HSQC NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ...........................
3 4 5 6 7 8 9 10 11 12 13 1
Figure S12. 1H-13C HMBC NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ........................... Figure S13. 1H NMR spectrum (400 MHz, acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ................................ Figure S14. 13C NMR spectrum (100 MHz, acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ................................ Figure S15. 1H-1H COSY NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ................................ Figure S16. 1H-1H NOESY NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ................................ Figure S17. 1H-13C HSQC NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ................................ Figure S18. 1H-13C HMBC NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)3-methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ............................ Figure S19. 1H NMR spectrum (400 MHz, CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4)..................................................................................... Figure S20. 13C NMR spectrum (100 MHz, CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4)..................................................................................... Figure S21. 1H-1H COSY NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4)..................................................................................... Figure S22. 1H-1H NOESY NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4)..................................................................................... Figure S23. 1H-13C HSQC NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4)..................................................................................... Figure S24. 1H-13C HMBC NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4).................................................................................. Figure S25. 1H NMR spectrum (400 MHz, acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) .................................... Figure S26. 13C NMR spectrum (100 MHz, acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) .................................... Figure S27. 1H-1H COSY NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) .................................... Figure S28. 1H-1H NOESY NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) .................................... Figure S29. 1H-13C HSQC NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) .................................... Figure S30. 1H-13C HMBC NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) ................................... Figure S31. 1H NMR spectrum (400 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(6E)-2hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6) .............................. Figure S32. 13C NMR spectrum (100 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(6E)-2hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6) .............................. Figure S33. HPLC chromatogram of (±)-4,2',4'-trihydroxy-3'-[(6E)-2-hydroxy-7-methyl3-methylene-6-octenyl]chalcone (6).................................................................
14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35
2
Figure S1. 1H NMR spectrum (400 MHz, CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7-methoxy3,7-dimethyl-2,5-octadienyl]chalcone (1)
3
Figure S2.
13
C NMR spectrum (100 MHz, CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7-
methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1)
4
Figure S3. 1H-1H COSY NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7-methoxy3,7-dimethyl-2,5-octadienyl]chalcone (1)
5
Figure S4. 1H-1H NOESY NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1)
6
Figure S5. 1H-13C HSQC NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1)
7
Figure S6. 1H-13C HMBC NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1)
8
Figure S7. 1H NMR spectrum (400 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6-hydroxy7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
9
Figure S8.
13
C NMR spectrum (100 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6-
hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
10
Figure S9. 1H-1H COSY NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6-hydroxy7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
11
Figure S10. 1H-1H NOESY NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
12
Figure S11. 1H-13C HSQC NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
13
Figure S12. 1H-13C HMBC NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
14
Figure S13. 1H NMR spectrum (400 MHz, acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3-methyl5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
15
Figure S14.
13
C NMR spectrum (100 MHz, acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3-
methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
16
Figure S15. 1H-1H COSY NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3-methyl5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
17
Figure S16. 1H-1H NOESY NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
18
Figure S17. 1H-13C HSQC NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
19
Figure S18. 1H-13C HMBC NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
20
Figure S19.
1
H NMR spectrum (400 MHz, CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
21
Figure S20.
13
C NMR spectrum (100 MHz, CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
22
Figure S21.
1
H-1H COSY NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
23
Figure S22.
1
H-1H NOESY NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
24
Figure S23.
1
H-13C HSQC NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
25
Figure S24.
1
H-13C HMBC NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
26
Figure S25. 1H NMR spectrum (400 MHz, acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro-2methoxyfurano)-4'-methoxychalcone (5)
27
Figure S26. 13C NMR spectrum (100 MHz, acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro-2methoxyfurano)-4'-methoxychalcone (5)
28
Figure S27. 1H-1H COSY NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro-2methoxyfurano)-4'-methoxychalcone (5)
29
Figure S28. 1H-1H NOESY NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro2-methoxyfurano)-4'-methoxychalcone (5)
30
Figure S29. 1H-13C HSQC NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro-2methoxyfurano)-4'-methoxychalcone (5)
31
Figure S30. 1H-13C HMBC NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro2-methoxyfurano)-4'-methoxychalcone (5)
32
Figure S31. 1H NMR spectrum (400 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(6E)-2hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6)
33
Figure S32.
13
C NMR spectrum (100 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(6E)-2-
hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6)
34
Figure S33. HPLC chromatogram of (±)-4,2',4'-trihydroxy-3'-[(6E)-2-hydroxy-7-methyl-3methylene-6-octenyl]chalcone (6). Analytical HPLC was carried out on a Waters instrument composed of a 1525 binary HPLC pump and a 2487 dual wavelength absorbance detector, with an Phenomenex Luna 5µ C18(2) column (5 µm, 250 mm × 4.60 mm i.d.). Purity evaluation of 6 was subjected to an analytical HPLC [mobile phase: 0–20 min, MeOH-H2O (3:2 → 4:1); 20– 40 min, MeOH-H2O (4:1 → 9:1); 40–60 min, MeOH-H2O (9:1→ 1:0), flow rate: 1 mL/min, detection: UV 365 nm].
35
Chalcones from Angelica keiskei: Evaluation of Their Heat Shock Protein Inducing Activities
Yun-Seo Kil,† Seul-Ki Choi,† Yun-Sil Lee,† Mahtab Jafari,‡ and Eun-Kyoung Seo*,†
†
College of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University,
Seoul 120-750, Korea ‡
Department of Pharmaceutical Sciences, University of California, Irvine, California 92697,
United States
Figure S1. Figure S2. Figure S3. Figure S4. Figure S5. Figure S6. Figure S7. Figure S8. Figure S9. Figure S10. Figure S11.
1
H NMR spectrum (400 MHz, CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 13 C NMR spectrum (100 MHz, CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 1 H-1H COSY NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 1 H-1H NOESY NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 1 H-13C HSQC NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 1 H-13C HMBC NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1) ..................................... 1 H NMR spectrum (400 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ........................... 13 C NMR spectrum (100 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ........................... 1 H-1H COSY NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ........................... 1 H-1H NOESY NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ........................... 1 H-13C HSQC NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ...........................
3 4 5 6 7 8 9 10 11 12 13 1
Figure S12. 1H-13C HMBC NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2) ........................... Figure S13. 1H NMR spectrum (400 MHz, acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ................................ Figure S14. 13C NMR spectrum (100 MHz, acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ................................ Figure S15. 1H-1H COSY NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ................................ Figure S16. 1H-1H NOESY NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ................................ Figure S17. 1H-13C HSQC NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ................................ Figure S18. 1H-13C HMBC NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)3-methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3) ............................ Figure S19. 1H NMR spectrum (400 MHz, CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4)..................................................................................... Figure S20. 13C NMR spectrum (100 MHz, CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4)..................................................................................... Figure S21. 1H-1H COSY NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4)..................................................................................... Figure S22. 1H-1H NOESY NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4)..................................................................................... Figure S23. 1H-13C HSQC NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4)..................................................................................... Figure S24. 1H-13C HMBC NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'methoxychalcone (4).................................................................................. Figure S25. 1H NMR spectrum (400 MHz, acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) .................................... Figure S26. 13C NMR spectrum (100 MHz, acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) .................................... Figure S27. 1H-1H COSY NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) .................................... Figure S28. 1H-1H NOESY NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) .................................... Figure S29. 1H-13C HSQC NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) .................................... Figure S30. 1H-13C HMBC NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3dihydro-2-methoxyfurano)-4'-methoxychalcone (5) ................................... Figure S31. 1H NMR spectrum (400 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(6E)-2hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6) .............................. Figure S32. 13C NMR spectrum (100 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(6E)-2hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6) .............................. Figure S33. HPLC chromatogram of (±)-4,2',4'-trihydroxy-3'-[(6E)-2-hydroxy-7-methyl3-methylene-6-octenyl]chalcone (6).................................................................
14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35
2
Figure S1. 1H NMR spectrum (400 MHz, CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7-methoxy3,7-dimethyl-2,5-octadienyl]chalcone (1)
3
Figure S2.
13
C NMR spectrum (100 MHz, CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7-
methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1)
4
Figure S3. 1H-1H COSY NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7-methoxy3,7-dimethyl-2,5-octadienyl]chalcone (1)
5
Figure S4. 1H-1H NOESY NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1)
6
Figure S5. 1H-13C HSQC NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1)
7
Figure S6. 1H-13C HMBC NMR spectrum (CDCl3) of 4,2',4'-trihydroxy-3'-[(2E,5E)-7methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1)
8
Figure S7. 1H NMR spectrum (400 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6-hydroxy7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
9
Figure S8.
13
C NMR spectrum (100 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6-
hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
10
Figure S9. 1H-1H COSY NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6-hydroxy7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
11
Figure S10. 1H-1H NOESY NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
12
Figure S11. 1H-13C HSQC NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
13
Figure S12. 1H-13C HMBC NMR spectrum (CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(2E)-6hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2)
14
Figure S13. 1H NMR spectrum (400 MHz, acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3-methyl5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
15
Figure S14.
13
C NMR spectrum (100 MHz, acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3-
methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
16
Figure S15. 1H-1H COSY NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3-methyl5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
17
Figure S16. 1H-1H NOESY NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
18
Figure S17. 1H-13C HSQC NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
19
Figure S18. 1H-13C HMBC NMR spectrum (acetone-d6) of 4,2',4'-trihydroxy-3'-[(2E)-3methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3)
20
Figure S19.
1
H NMR spectrum (400 MHz, CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
21
Figure S20.
13
C NMR spectrum (100 MHz, CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
22
Figure S21.
1
H-1H COSY NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
23
Figure S22.
1
H-1H NOESY NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
24
Figure S23.
1
H-13C HSQC NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
25
Figure S24.
1
H-13C HMBC NMR spectrum (CD3OD) of 2',3'-furano-4-hydroxy-4'-
methoxychalcone (4)
26
Figure S25. 1H NMR spectrum (400 MHz, acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro-2methoxyfurano)-4'-methoxychalcone (5)
27
Figure S26. 13C NMR spectrum (100 MHz, acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro-2methoxyfurano)-4'-methoxychalcone (5)
28
Figure S27. 1H-1H COSY NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro-2methoxyfurano)-4'-methoxychalcone (5)
29
Figure S28. 1H-1H NOESY NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro2-methoxyfurano)-4'-methoxychalcone (5)
30
Figure S29. 1H-13C HSQC NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro-2methoxyfurano)-4'-methoxychalcone (5)
31
Figure S30. 1H-13C HMBC NMR spectrum (acetone-d6) of (±)-4-hydroxy-2',3'-(2,3-dihydro2-methoxyfurano)-4'-methoxychalcone (5)
32
Figure S31. 1H NMR spectrum (400 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(6E)-2hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6)
33
Figure S32.
13
C NMR spectrum (100 MHz, CDCl3) of (±)-4,2',4'-trihydroxy-3'-[(6E)-2-
hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6)
34
Figure S33. HPLC chromatogram of (±)-4,2',4'-trihydroxy-3'-[(6E)-2-hydroxy-7-methyl-3methylene-6-octenyl]chalcone (6). Analytical HPLC was carried out on a Waters instrument composed of a 1525 binary HPLC pump and a 2487 dual wavelength absorbance detector, with an Phenomenex Luna 5µ C18(2) column (5 µm, 250 mm × 4.60 mm i.d.). Purity evaluation of 6 was subjected to an analytical HPLC [mobile phase: 0–20 min, MeOH-H2O (3:2 → 4:1); 20– 40 min, MeOH-H2O (4:1 → 9:1); 40–60 min, MeOH-H2O (9:1→ 1:0), flow rate: 1 mL/min, detection: UV 365 nm].
35
