rubesanolides c-e ms obc 2012 04 02 supp · e-mail: [email protected] ; fax: +86 852 3840100;tel: +86...
TRANSCRIPT
![Page 1: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/1.jpg)
1
Supporting Information
Rubesanolides C-E: The abietane diterpenoids isolated from Isodon rubescens and
evaluation of their anti-biofilm activity
Juan Zou,a, c Lutai Pan,*, a Qiji Li,a Jianxin Pu,c Ping Yao,d Min Zhu,e Jeffrey A. Banas,e Hongjie Zhang,* b and Handong Sunc a Guiyang College of Traditional Chinese Medicine, Guiyang 550002, Guizhou, People’s Republic of China. E-mail: [email protected] ; Fax:
+86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist University Road, Kowloon Tong, Kowloon, Hong Kong. Fax: +852 3411
2461; Tel: +852 3411 2956; E-mail: [email protected]
c State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences,
Kunming 650201, Yunnan, People’s Republic of China d Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street,
Chicago, Illinois 60612, United States, and College of Pharmacy. e Dows Institute for Dental Research, College of De ntistry, The University of Iowa, 418 Dental Science N, Iowa City, Iowa 52242, United States
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 2: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/2.jpg)
2
Table of Contents
No. Contents P. No. Contents P. 1 Figure S1. 1H NMR spectrum of rubesanolide C (1) 3 17 Figure S17. HRESIMS spectrum of rubesanolide D (2) . 19 2 Figure S2. 13C NMR spectra of rubesanolide C (1) 4 18 Figure S18. UV spectrum of rubesanolide D (2) 20 3 Figure S3. HSQC spectrum of rubesanolide C (1) 5 19 Figure S19. IR spectrum of rubesanolide D (2) 21 4 Figure S4. HMBC spectrum of rubesanolide C (1) 6 20 Figure S20. CD spectrum of rubesanolide D (2) 22 5 Figure S5. 1H-1H COSY spectrum of rubesanolide C (1) 7 21 Figure S21. 1H NMR spectrum of rubesanolide E (3) 23 6 Figure S6. ROESY spectrum of rubesanolide C (1) 8 22 Figure S22. 13C NMR spectra of rubesanolide E (3) 24 7 Figure S7. HRESIMS spectrum of rubesanolide C (1) 9 23 Figure S23. HSQC spectrum of rubesanolide E (3) 25 8 Figure S8. UV spectrum of rubesanolide C (1) 10 24 Figure S24. HMBC spectrum of rubesanolide E (3) 26 9 Figure S9. IR spectrum of rubesanolide C (1) 11 25 Figure S25. 1H-1H COSY spectrum of rubesanolide E (3) 27 10 Figure S10. CD spectrum of rubesanolide C (1) 12 26 Figure S26. ROESY spectrum of rubesanolide E (3) 28 11 Figure S11. 1H NMR spectrum of rubesanolide D (2) 13 27 Figure S27. HRESIMS spectrum of rubesanolide E (3) 29 12 Figure S12. 13C NMR spectrum of rubesanolide D (2) 14 28 Figure S28. UV spectrum of rubesanolide E (3) 30 13 Figure S13. HMQC spectrum of rubesanolide D (2) 15 29 Figure S29. IR spectrum of rubesanolide E (3) 31 14 Figure S14. HMBC spectrum of rubesanolide D (2) 16 30 Figure S30. CD spectrum of rubesanolide E (3) 32
15 Figure S15. 1H-1H COSY spectrum of rubesanolide D (2) 17 31 Figure S31. Key 2D correlations A) COSY (-in blue), HMBC (→in red) and ROESY of rubesanolides C (1) , D (2) and E (3).
33
16 Figure S16. ROESY spectrum of rubesanolide D (2) 18
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 3: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/3.jpg)
3
Figure S1. 1H NMR spectrum of rubesanolide C (1)
1.61.71.81.92.02.12.22.32.4f1 (ppm)
OO
H
OH
Rubesanolides C (1)
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 4: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/4.jpg)
4
Figure S2. 13C NMR spectra of rubesanolide C (1)
OO
H
OH
Rubesanolides C (1)
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 5: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/5.jpg)
5
Figure S3. HSQC spectrum of rubesanolide C (1)
OO
H
OH
Rubesanolides C (1)
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 6: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/6.jpg)
6
Figure S4. HMBC spectrum of rubesanolide C (1)
OO
H
OH
Rubesanolides C (1)
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 7: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/7.jpg)
7
Figure S5. 1H-1H COSY spectrum of rubesanolide C (1)
OO
H
OH
Rubesanolides C (1)
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 8: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/8.jpg)
8
Figure S6. ROESY spectrum of rubesanolide C (1)
OO
H
OH
Rubesanolides C (1)
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 9: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/9.jpg)
9
Figure S7. HRESIMS spectrum of rubesanolide C (1)
OO
H
OH
Rubesanolides C (1)
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 10: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/10.jpg)
10
Figure S8. UV spectrum of rubesanolide C (1)
OO
H
OH
Rubesanolides C (1)
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 11: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/11.jpg)
11
Figure S9. IR spectrum of rubesanolide C (1)
OO
H
OH
Rubesanolides C (1)
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 12: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/12.jpg)
12
Figure S10. CD spectrum of rubesanolide C (1)
OO
H
OH
Rubesanolides C (1)
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 13: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/13.jpg)
13
Figure S11. 1H NMR spectrum of rubesanolide D (2)
1.00
1.06
1.48
191
041.
9190
1.92
271.
9343
1.94
361.
9478
1.95
441.
9647
1.96
901.
9835
2.00
022.
0163
2.02
282.
0291
2.04
612.
0628
2.07
252.
0975
2.10
612.
1145
2.13
202.
1400
2.14
892.
1653
2.17
092.
1789
2.18
472.
1953
2.20
142.
2097
2.21
522.
2257
2.23
522.
2432
2.24
432.
2606
2.27
78
OO
H
OH
Rubesanolides D (2)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 14: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/14.jpg)
14
Figure S12. 13C NMR spectrum of rubesanolide D (2)
OO
H
OH
Rubesanolides D (2)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 15: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/15.jpg)
15
Figure S13. HMQC spectrum of rubesanolide D (2)
OO
H
OH
Rubesanolides D (2)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 16: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/16.jpg)
16
Figure S14. HMBC spectrum of rubesanolide D (2)
OO
H
OH
Rubesanolides D (2)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 17: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/17.jpg)
17
Figure S15. 1H-1H COSY spectrum of rubesanolide D (2)
OO
H
OH
Rubesanolides D (2)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 18: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/18.jpg)
18
Figure S16. NOESY spectrum of rubesanolide D (2)
OO
H
OH
Rubesanolides D (2)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 19: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/19.jpg)
19
Figure S17. HRESIMS spectrum of rubesanolide D (2)
OO
H
OH
Rubesanolides D (2)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 20: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/20.jpg)
20
Figure S18. UV spectrum of rubesanolide D (2)
OO
H
OH
Rubesanolides D (2)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 21: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/21.jpg)
21
Figure S19. IR spectrum of rubesanolide D (2)
OO
H
OH
Rubesanolides D (2)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 22: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/22.jpg)
22
Figure S20. CD spectrum of rubesanolide D (2)
OO
H
OH
Rubesanolides D (2)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 23: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/23.jpg)
23
Figure S21. 1H NMR spectrum of rubesanolide E (3)
1.00
2.11 2.
59
1.01
2.96
1.12
481.
1357
1.14
281.
1527
1.16
241.
1701
1.17
921.
1887
1.20
231.
2120
1.22
781.
2374
1.25
341.
2632
1.35
581.
3652
1.38
161.
3907
1.44
941.
4549
1.46
531.
4722
1.48
691.
4996
1.51
191.
5263
1.53
791.
5623
1.57
051.
5885
1.59
721.
6105
1.62
501.
6370
1.65
10
1.69
621.
7087
1.72
19
OO
H
Rubesanolides E (3)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 24: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/24.jpg)
24
Figure S22. 13C NMR spectra of rubesanolide E (3)
OO
H
Rubesanolides E (3)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 25: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/25.jpg)
25
Figure S23. HSQC spectrum of rubesanolide E (3)
OO
H
Rubesanolides E (3)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 26: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/26.jpg)
26
Figure S24. HMBC spectrum of rubesanolide E (3)
OO
H
Rubesanolides E (3)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 27: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/27.jpg)
27
Figure S25. 1H-1H COSY spectrum of rubesanolide E (3)
OO
H
Rubesanolides E (3)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 28: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/28.jpg)
28
Figure S26. ROESY spectrum of rubesanolide E (3)
OO
H
Rubesanolides E (3)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 29: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/29.jpg)
29
Figure S27. HRESIMS spectrum of rubesanolide E (3)
OO
H
Rubesanolides E (3)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 30: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/30.jpg)
30
Figure S28. UV spectrum of rubesanolide E (3)
OO
H
Rubesanolides E (3)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 31: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/31.jpg)
31
Figure S29. IR spectrum of rubesanolide E (3)
OO
H
Rubesanolides E (3)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 32: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/32.jpg)
32
Figure S30. CD spectrum of rubesanolide E (3)
OO
H
Rubesanolides E (3)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
![Page 33: Rubesanolides C-E ms OBC 2012 04 02 Supp · E-mail: ltpan@yahoo.cn ; Fax: +86 852 3840100;Tel: +86 852 3840100 b School of Chinese Medicine, Hong Kong Baptist University, 7 Baptist](https://reader033.vdocument.in/reader033/viewer/2022053112/608675cb96a3701f6f6e8bef/html5/thumbnails/33.jpg)
33
Figure S31. Key 2D correlations A) COSY (- in blue), HMBC (→ in red) and ROESY of rubesanolides C (1), D (2) and E (3)
Key COSY (—in blue), HMBC (→in red) and ROESY (↔in red) correlations for 1
Key COSY (— in blue), HMBC (→ in red) and ROESY (↔ in red) correlations for 2.
Key COSY (— in blue), HMBC (→ in red) and ROESY (↔ in red) correlations for 3.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012