Co-Culture of the Fungus Fusarium tricinctum with Streptomyces … · 2019. 1. 3. · dJohn von...

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Supplementary information

Co-Culture of the Fungus Fusarium tricinctum with Streptomyces lividans

Induces Production of Cryptic Naphthoquinone Dimers

Mariam Moussa,a Weaam Ebrahim,a,b Michele Bonus,c Holger Gohlke,c,d Attila Mándi,e Tibor

Kurtán,e Rudolf Hartmann,f Rainer Kalscheuer,a Wenhan Lin,g Zhen Liu,a,* and Peter Prokscha,*

aInstitute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf,

Universitätsstrasse 1, 40225 Düsseldorf, Germany. E-mail: zhenfeizi0@sina.com(Z.L.), proksch@uni-

duesseldorf.de(P. P.)

bDepartment of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt

cInstitute of Pharmaceutical and Medicinal Chemistry, Heinrich-Heine-Universität Düsseldorf,

Universitätsstrasse 1, 40225 Düsseldorf, Germany

dJohn von Neumann Institute for Computing (NIC), Jülich Supercomputing Centre (JSC), and Institute for

Complex Systems - Structural Biochemistry (ICS-6), Forschungszentrum Jülich GmbH, Wilhelm-Johnen-

Straße, 52425 Jülich, Germany.

eDepartment of Organic Chemistry, University of Debrecen, Egyetem tér 1, Debrecen 4032, Hungary

fInstitute of Complex Systems - Structural Biochemistry, Forschungszentrum Jülich GmbH, Wilhelm-Johnen-

Straße, 52428 Jülich, Germany

gState Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2019

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Table of Contents 

S1. UV spectrum of compound 1. ................................................................................................................. 3 

S2. HRESIMS of compound 1. ..................................................................................................................... 4 

S3. 1H NMR (600 MHz, CDCl3-CD3OD 2:1) spectrum of compound 1. ..................................................... 5 

S4. 13C NMR (150 MHz, CDCl3-CD3OD 2:1) spectrum of compound 1. .................................................... 6 

S5. HSQC (600 and 150MHz, CDCl3-CD3OD 2:1) spectrum of compound 1. ............................................ 7 

S6. HMBC (600 and 150 MHz, CDCl3-CD3OD 2:1) spectrum of compound 1. .......................................... 8 

S7. Long-range HMBC (600 and 150 MHz, CDCl3-CD3OD 2:1) spectrum of compound 1. ...................... 9 

S8. UV spectrum of compound 2. ............................................................................................................... 10 

S9. HRESIMS of compound 2. ................................................................................................................... 11 

S10. 1H NMR (600 MHz, CDCl3) spectrum of compound 2. ..................................................................... 12 

S11. HSQC (600 and 150 MHz, CDCl3) spectrum of compound 2. ........................................................... 13 

S12. HMBC (600 and 150 MHz, CDCl3) spectrum of compound 2. .......................................................... 14 

S13. UV spectrum of compound 3. ............................................................................................................. 15 

S14. HRESIMS of compound 3. ................................................................................................................. 16 

S15. 1H NMR (600 MHz, CDCl3) spectrum of compound 3. ..................................................................... 17 

S16. HSQC (600 and 150 MHz, CDCl3) spectrum of compound 3. ........................................................... 18 

S17. HMBC (600 and 150 MHz, CDCl3) spectrum of compound 3. .......................................................... 19 

S18. UV spectrum of compound 4. ............................................................................................................. 20 

S19. HRESIMS of compound 4. ................................................................................................................. 21 

S20. 1H NMR (600 MHz, DMSO-d6) spectrum of compound 4. ............................................................... 22 

S21. HSQC (600 and 150 MHz, DMSO-d6) spectrum of compound 4. ..................................................... 23 

S22. HMBC (600 and 150 MHz, DMSO-d6) spectrum of compound 4. .................................................... 24 

S23. ROESY (600 and 150 MHz, DMSO-d6) spectrum of compound 4. ................................................... 25 

S24. UV spectrum of compound 5. ............................................................................................................. 26 

S25. HRESIMS of compound 5. ................................................................................................................. 27 

S26. 1H NMR (750 MHz, acetone-d6) spectrum of compound 5. ............................................................... 28 

S27. HSQC (750 and 175 MHz, acetone-d6) spectrum of compound 5. ..................................................... 29 

S28. HMBC (750 and 175 MHz, acetone-d6) spectrum of compound 5. ................................................... 30 

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Peak #3 100% at 33.64 min

-10,0

70,0

200 250 300 350 400 450 500 550 595

%

nm

277.6223.2

320.1

No spectra library hits found!

S1. UV spectrum of compound 1.

4  

S2. HRESIMS of compound 1.

5  

S3. 1H NMR (600 MHz, CDCl3-CD3OD 2:1) spectrum of compound 1.

6  

S4. 13C NMR (150 MHz, CDCl3-CD3OD 2:1) spectrum of compound 1.

7  

S5. HSQC (600 and 150MHz, CDCl3-CD3OD 2:1) spectrum of compound 1.

8  

S6. HMBC (600 and 150 MHz, CDCl3-CD3OD 2:1) spectrum of compound 1.

9  

S7. Long-range HMBC (600 and 150 MHz, CDCl3-CD3OD 2:1) spectrum of compound 1.

10  

Peak #5 100% at 39.20 min

-10,0

70,0

200 250 300 350 400 450 500 550 595

%

nm

277.2222.8

319.3

No spectra library hits found!

S8. UV spectrum of compound 2.

11  

S9. HRESIMS of compound 2.

12  

S10. 1H NMR (600 MHz, CDCl3) spectrum of compound 2.

13  

S11. HSQC (600 and 150 MHz, CDCl3) spectrum of compound 2.

14  

S12. HMBC (600 and 150 MHz, CDCl3) spectrum of compound 2.

15  

Peak #3 100% at 38.61 min

-10,0

70,0

200 250 300 350 400 450 500 550 595

%

nm

276.8222.4

318.7

No spectra library hits found!

S13. UV spectrum of compound 3.

16  

S14. HRESIMS of compound 3.

17  

S15. 1H NMR (600 MHz, CDCl3) spectrum of compound 3.

18  

S16. HSQC (600 and 150 MHz, CDCl3) spectrum of compound 3.

19  

S17. HMBC (600 and 150 MHz, CDCl3) spectrum of compound 3.

20  

Peak #2 100% at 29.03 min

-10,0

70,0

200 250 300 350 400 450 500 550 595

%

nm

223.1278.1

313.4

No spectra library hits found!

S18. UV spectrum of compound 4.

21  

S19. HRESIMS of compound 4.

22  

S20. 1H NMR (600 MHz, DMSO-d6) spectrum of compound 4.

23  

S21. HSQC (600 and 150 MHz, DMSO-d6) spectrum of compound 4.

24  

S22. HMBC (600 and 150 MHz, DMSO-d6) spectrum of compound 4.

25  

S23. ROESY (600 and 150 MHz, DMSO-d6) spectrum of compound 4.

26  

Peak #3 100% at 23.13 min

-10,0

70,0

200 250 300 350 400 450 500 550 595

%

nm

228.5242.7

263.1

No spectra library hits found!

S24. UV spectrum of compound 5.

27  

S25. HRESIMS of compound 5.

28  

S26. 1H NMR (750 MHz, acetone-d6) spectrum of compound 5.

29  

S27. HSQC (750 and 175 MHz, acetone-d6) spectrum of compound 5.

30  

S28. HMBC (750 and 175 MHz, acetone-d6) spectrum of compound 5.