Supplementary Materials Preparative Separation and Purification of Trichothecene Mycotoxins from the Marine Fungus Fusarium sp. LS68 by High-Speed Counter-current Chromatography in Stepwise Elution Mode Yong Liu 1, Xuezhen Zhou 1, C. Benjamin Naman 1,2,3 ,Yanbin Lu 4, Lijian Ding 1,2,*and Shan He 1,2,* 1
2 3
Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Research Center, Ningbo University, Ningbo 315211, China; E-Mails:
[email protected] (Y.L.);
[email protected] (X.Z);
[email protected] (L.D.). Key Laboratory of Marine Biotechnology of Zhejiang Province, Ningbo University, Ningbo, Zhejiang 315211, China; Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, CA 92093, USA
4
Institute of Seafood, Zhejiang Gongshang University, Hangzhou 310012, China
* Correspondence:
[email protected] (S.H.),
[email protected] (L.D.); Tel.: +86-574-8760-0458 (S.H.).
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Table of Contents
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Figure S1a. 1H NMR spectrum of compound 1 (CDCl3, 600 MHz)
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Figure S1b. 13C NMR spectrum of compound 1 (CDCl3, 150 MHz)
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Figure S1c. HRESIMS spectrum of compound 1
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Figure S1d. UV spectrum of compound 1
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Figure S2a. 1H NMR spectrum of compound 2 (CDCl3, 600 MHz)
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Figure S2b. 13C NMR spectrum of compound 2 (CDCl3, 150 MHz)
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Figure S2c. HRESIMS spectrum of compound 2
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Figure S2d. UV spectrum of compound 2
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Figure S3a. 1H NMR spectrum of compound 3 (CDCl3, 600 MHz)
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Figure S3b.13CNMR spectrum of compound 3 (CDCl3, 150 MHz)
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Figure S3c. HRESIMS spectrum of compound 3
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Figure S3d. UV spectrum of compound 3
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Figure S4a. 1H NMR spectrum of compound 4 (CDCl3, 600 MHz)
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Figure S4b.13CNMR spectrum of compound 4 (CDCl3, 150 MHz)
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Figure S4c. HRESIMS spectrum of compound 4
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Figure S4d. UV spectrum of compound 4
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Table S1. NMR data of compound 1 in CDCl3
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Table S2. NMR data of compound 2 in CDCl3
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Table S3. NMR data of compound 3 in CDCl3
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Table S4. NMR data of compound 4 in CDCl3
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Table S5. Specific rotation values of compounds 1–4
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Table S6. UV values of compounds 1–4.
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2
Figure S1a. 1H NMR spectrum of compound 1 (CDCl3, 600 MHz)
Figure S1b. 13C NMR spectrum of compound 1 (CDCl3, 150 MHz)
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Figure S1c. HRESIMS spectrum of compound 1
Figure S1d. UV spectrum of compound 1
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Figure S2a. 1H NMR spectrum of compound 2 (CDCl3, 600 MHz)
Figure S2b.13C NMR spectrum of compound 2 (CDCl3, 150 MHz) 5
Figure S2c. HRESIMS spectrum of compound 2
Figure S2d. UV spectrum of compound 2
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Figure S3a. 1H NMR spectrum of compound 3 (CDCl3, 600 MHz)
Figure S3b.13CNMR spectrum of compound 3 (CDCl3, 150 MHz) 7
Figure S3c. HRESIMS spectrum of compound 3
Figure S3d. UV spectrum of compound 3
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Figure S4a. 1H NMR spectrum of compound 4 (CDCl3, 600 MHz)
Figure S4b.13CNMR spectrum of compound 4 (CDCl3, 150 MHz)
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Figure S4c. HRESIMS spectrum of compound 4
Figure S4d. UV spectrum of compound 4
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Table S1. NMR data of compound 1 in CDCl3 Position 2 3 4
literature data (1H 600 MHz, 13C 150 MHz)1 δH (mult, J)
δC
δH (mult, J)
δC
3.83 (1H, d, 5.0 Hz)
79.5
3.83 (1H, d, 5.1 Hz)
79.4
36.1
2.50 (1H,m); 2.05 (1H, m)
36.0
74.4
6.21 (1H, dd, 8.1, 3.9 Hz)
74.4
2.51 (1H, dd, 15.0, 8.0 Hz); 2.04 (1H, ddd, 15.0, 5.0, 4.0 Hz) 6.20 (1H, dd, 8.0, 4.0 Hz)
5 6 7
8
experimental data(1H 600 MHz, 13C 150 MHz)
2.02 (1H, ddd, 12.6, 12.6, 5.5 Hz) 1.65 (1H, ddd, 12.6, 5.5, 1.4 Hz) 2.01 (1H, ddd, 12.6, 12.6, 5.5 Hz);
2.00
(1H, ddd, 12.6, 5.5, 1.4 Hz)
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48.6
48.6
42.9
42.9
21.8
2.03 (1H, m); 1.65 (1H, m)
21.8
27.9
2.00 (2H, m)
27.8
140.4
140.4
10
5.46 (1H, brd)
119.1
5.48 (1H, m)
119.0
11
3.89 (1H, brd)
67.5
3.90 (1H, d, 5.7 Hz)
67.4
12
65.8
13
3.12 (1H, d, 4.1 Hz); 2.80 (1H, d, 4.1 Hz)
48.4
14
0.77 (3H, s)
6.9
15
4.29 (1H, d, 12.5 Hz); 3.92 (1H, d, 12.5 Hz)
64.0
16
1.69 (3H, brs)
23.5
1ʹ 2ʹ
5ʹ
3.14 (1H, d, 4.1 Hz); 2.82 (1H, d, 4.0 Hz)
48.3
0.79 (3H, s)
6.8
4.31 (1H, d, 12.5 Hz); 3.93 (1H, d, 12.5 Hz) 1.71 (3H, m)
166.7 5.94 (1H, brs)
117.4
3ʹ 4ʹ
65.8
2.48
(1H, dd, 13.0, 6.8,