Ol902971w Si 002

Two new quinochalcones from the florets of
Carthamus tinctorius
Jian-Shuang Jiang, Jun He, Zi-Ming Feng, Pei-Cheng Zhang*
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union
Medical College (Key Laboratory of Bioactive Substances and Resources Utilization of
Chinese Herbal Medicine, Ministry of Education), Beijing 100050, People’s Republic of
China
S1
Supporting Information
Figure S1. UV spectrum of saffloquinoside A (1) in MeOH
Figure S2. IR spectrum of saffloquinoside A (1)
Figure S3. ESI spectrum of saffloquinoside A (1) in MeOH
Figure S4. HRESIMS spectrum of saffloquinoside A (1) in MeOH
1
Figure S5. H NMR spectrum of saffloquinoside A (1) in DMSO-d6
13
Figure S6. C NMR spectrum of saffloquinoside A (1) in DMSO-d6
Figure S7. HSQC NMR spectrum of saffloquinoside A (1) in DMSO-d6
Figure S8. HMBC NMR spectrum of saffloquinoside A (1) in DMSO-d6
Figure S9. GCOSY NMR spectrum of saffloquinoside A (1) in DMSO-d6
Figure S10. TOCSY NMR spectrum of saffloquinoside A (1) in DMSO-d6
Figure S11. ROESY NMR spectrum of saffloquinoside A (1) in DMSO-d6
Figure S12. CD spectrum of saffloquinoside A (1) in MeOH
Figure S13. UV spectrum of saffloquinoside B (2) in MeOH
Figure S14. IR spectrum of saffloquinoside B (2)
Figure S15. ESI spectrum of saffloquinoside B (2) in MeOH
S2
Figure S16. HRESIMS spectrum of saffloquinoside B (2) in MeOH
1
Figure S17. H NMR spectrum of saffloquinoside B (2) in DMSO-d6
1
Figure S18. H NMR spectrum of saffloquinoside B (2) in DMSO-d6+D2O
13
Figure S19. C NMR spectrum of saffloquinoside B (2) in DMSO-d6
Figure S20. HSQC NMR spectrum of saffloquinoside B (2) in DMSO-d6
Figure S21. HMBC NMR spectrum of saffloquinoside B (2) in DMSO-d6
Figure S22. GCOSY NMR spectrum of saffloquinoside B (2) in DMSO-d6
Figure S23. TOCSY NMR spectrum of saffloquinoside B (2) in DMSO-d6
Figure S24. NOE NMR spectrum of saffloquinoside B (2) in DMSO-d6+D2O
Figure S25. CD spectrum of saffloquinoside B (2) in MeOH
Figure S26. CD spectrum of safflomin C in MeOH
Figure S27. CD spectrum of safflor yellow A in MeOH
Figure S28. CD spectrum of hydroxysafflor yellow A in MeOH
Figure S29. CD spectrum of anhydrosafflor yellow B in MeOH
Figure S30. CD spectrum of cartormin in MeOH
S3
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
saffloquinoside A (1)
Figure S1. UV spectrum of saffloquinoside A (1) in MeOH
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
Figure S2. IR spectrum of saffloquinoside A (1)
S4
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
Figure S3. ESI spectrum of saffloquinoside A (1) in MeOH
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
Figure S4. HRESIMS spectrum of saffloquinoside A (1) in MeOH
S5
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
Figure S5. 1H NMR spectrum of saffloquinoside A (1) in DMSO-d6
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
Figure S6. 13C NMR spectrum of saffloquinoside A (1) in DMSO-d6
S6
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
Figure S7. HSQC NMR spectrum of saffloquinoside A (1) in DMSO-d6
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
Figure S8. HMBC NMR spectrum of saffloquinoside A (1) in DMSO-d6
S7
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
Figure S9. GCOSY NMR spectrum of saffloquinoside A (1) in DMSO-d6
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
Figure S10. TOCSY NMR spectrum of saffloquinoside A (1) in DMSO-d6
S8
HO
HO
HO
O
HO OH
O O O OH
HO
HO OH O OH
Figure S11. ROESY NMR spectrum of saffloquinoside A (1) in DMSO-d6
0
HO
HO
HO
O
-2 HO OH
O O O OH
Mol. CD HO
HO OH O OH
-4 saffloquinoside A (1)
262 nm, -4.22904
-6
200 300 400 500
Wavelength [nm]
Figure S12. CD spectrum of saffloquinoside A (1) in MeOH
S9
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
saf floquinoside B (2)
Figure S13. UV spectrum of saffloquinoside B (2) in MeOH
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S14. IR spectrum of saffloquinoside B (2)
S10
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S15. ESI spectrum of saffloquinoside B (2) in MeOH
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S16. HRESIMS spectrum of saffloquinoside B (2) in MeOH
S11
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S17. 1H NMR spectrum of saffloquinoside B (2) in DMSO-d6
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S18. 1H NMR spectrum of saffloquinoside B (2) in DMSO-d6+D2O
S12
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S19. 13C NMR spectrum of saffloquinoside B (2) in DMSO-d6
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S20. HSQC NMR spectrum of saffloquinoside B (2) in DMSO-d6
S13
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S21. HMBC NMR spectrum of saffloquinoside B (2) in DMSO-d6
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S22. GCOSY NMR spectrum of saffloquinoside B (2) in DMSO-d6
S14
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S23. TOCSY NMR spectrum of saffloquinoside B (2) in DMSO-d6
HO
HO
HO
O
HO OH
O O OH
HO O OH
O
HO
HO OH
HO
Figure S24. NOE NMR spectrum of saffloquinoside B (2) in DMSO-d6+D2O
S15
4 HO
HO
HO
O
0
Mol. CD
HO OH
O O OH
-4 HO
HO
O
O OH
HO OH
HO
-8
200 300 400 500
Wavelength [nm]
Figure S25. CD spectrum of saffloquinoside B (2) in MeOH
1
0
HO
HO
HO
O
Mol. CD -5 HO OH
O OH
HO
HO
O OH O
266.5 nm, -7.72423 OH

safflomin C
-10
200 300 400 500
Wavelength [nm]
Figure S26. CD spectrum of safflomin C in MeOH
S16
3 HO
HO
HO
2
O
HO OH
HO O O OH
0
HO
O O OH
HO
Mol. CD -2
safflor yellow A
-4 255.5 nm, -3.23082
-6
-7
200 300 400 500
Wavelength [nm]
Figure S27. CD spectrum of safflor yellow A in MeOH
0
HO
HO
HO
O
-5 HO OH
HO O OH
Mol. CD
O
HO
OH OH O
HO
-10 HO
hydroxysaff lor yellow A

268 nm, -11.9315
-15
200 300 400 500
Wavelength [nm]
Figure S28. CD spectrum of hydroxysafflor yellow A in MeOH
S17
20
OH
HO
HO
HO
287 nm, -7.76292

O O
270 nm, -8.97664

HO OH
10 HO O OH HO O
OH
HO OH
OH O O
O
OH
HO OH
OH
Mol. CD 0 OH
OH
anhydrosafflor yellow B
-10
-20
200 300 400 500
Wavelength [nm]
Figure S29. CD spectrum of anhydrosafflor yellow B in MeOH
5
HO
OH
0
OH
-5 O
HO
Mol.CD
H OH
-10 N O OH
O
-15
HO OH O OH
-20 cartormin
-25
200 300
Wavelength [nm]
Figure S30. CD spectrum of cartormin in MeOH
S18

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Two new quinochalcones from the florets of

Jian-Shuang Jiang, Jun He, Zi-Ming Feng, Pei-Cheng Zhang*

Medical College (Key Laboratory of Bioactive Substances and Resources Utilization of

Chinese Herbal Medicine, Ministry of Education), Beijing 100050, People’s Republic of

Figure S1. UV spectrum of saffloquinoside A (1) in MeOH

Figure S2. IR spectrum of saffloquinoside A (1)

Figure S3. ESI spectrum of saffloquinoside A (1) in MeOH

Figure S4. HRESIMS spectrum of saffloquinoside A (1) in MeOH

Figure S7. HSQC NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S8. HMBC NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S9. GCOSY NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S10. TOCSY NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S11. ROESY NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S12. CD spectrum of saffloquinoside A (1) in MeOH

Figure S13. UV spectrum of saffloquinoside B (2) in MeOH

Figure S14. IR spectrum of saffloquinoside B (2)

Figure S15. ESI spectrum of saffloquinoside B (2) in MeOH

Figure S20. HSQC NMR spectrum of saffloquinoside B (2) in DMSO-d6

Figure S21. HMBC NMR spectrum of saffloquinoside B (2) in DMSO-d6

Figure S22. GCOSY NMR spectrum of saffloquinoside B (2) in DMSO-d6

Figure S23. TOCSY NMR spectrum of saffloquinoside B (2) in DMSO-d6

Figure S24. NOE NMR spectrum of saffloquinoside B (2) in DMSO-d6+D2O

Figure S25. CD spectrum of saffloquinoside B (2) in MeOH

Figure S26. CD spectrum of safflomin C in MeOH

Figure S27. CD spectrum of safflor yellow A in MeOH

Figure S28. CD spectrum of hydroxysafflor yellow A in MeOH

Figure S29. CD spectrum of anhydrosafflor yellow B in MeOH

Figure S30. CD spectrum of cartormin in MeOH

Figure S1. UV spectrum of saffloquinoside A (1) in MeOH

Figure S2. IR spectrum of saffloquinoside A (1)

Figure S3. ESI spectrum of saffloquinoside A (1) in MeOH

Figure S4. HRESIMS spectrum of saffloquinoside A (1) in MeOH

Figure S5. 1H NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S6. 13C NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S7. HSQC NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S8. HMBC NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S9. GCOSY NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S10. TOCSY NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S11. ROESY NMR spectrum of saffloquinoside A (1) in DMSO-d6

Figure S12. CD spectrum of saffloquinoside A (1) in MeOH

Figure S13. UV spectrum of saffloquinoside B (2) in MeOH

Figure S14. IR spectrum of saffloquinoside B (2)

Figure S15. ESI spectrum of saffloquinoside B (2) in MeOH

Figure S16. HRESIMS spectrum of saffloquinoside B (2) in MeOH

Figure S17. 1H NMR spectrum of saffloquinoside B (2) in DMSO-d6

Figure S18. 1H NMR spectrum of saffloquinoside B (2) in DMSO-d6+D2O

Figure S19. 13C NMR spectrum of saffloquinoside B (2) in DMSO-d6

Figure S20. HSQC NMR spectrum of saffloquinoside B (2) in DMSO-d6

Figure S21. HMBC NMR spectrum of saffloquinoside B (2) in DMSO-d6

Figure S22. GCOSY NMR spectrum of saffloquinoside B (2) in DMSO-d6

Figure S23. TOCSY NMR spectrum of saffloquinoside B (2) in DMSO-d6

Figure S24. NOE NMR spectrum of saffloquinoside B (2) in DMSO-d6+D2O

Figure S25. CD spectrum of saffloquinoside B (2) in MeOH

266.5 nm, -7.72423 OH

Figure S26. CD spectrum of safflomin C in MeOH

-4 255.5 nm, -3.23082

Figure S27. CD spectrum of safflor yellow A in MeOH

hydroxysaff lor yellow A

Figure S28. CD spectrum of hydroxysafflor yellow A in MeOH

287 nm, -7.76292

270 nm, -8.97664

Figure S29. CD spectrum of anhydrosafflor yellow B in MeOH