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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: [email protected](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
2
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
3
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.
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