Supporting Information · Structures of the isolated compounds 7–15 from Alternaria sp. sb23....

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Supporting Information

Trichothecenes from an Endophytic Fungus Alternaria sp. sb23

Ying Gao, Jia Zhou, Hanli Ruan

Affiliation

School of Pharmacy, Tongji Medical College of Huazhong University of Science and

Technology, Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation,

Wuhan, People’s Republic of China

Correspondence

Prof. Dr. Hanli Ruan

School of Pharmacy

Tongji Medical College of Huazhong University of Science and Technology

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation

Hangkonglu 13

Wuhan 430030

People’s Republic of China

Phone: +86 13339986848

[email protected]

© Georg Thieme Verlag KG · 10.1055/a-1091-8831 · Planta Med · Gao Y et al.

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Table of contents

Table 1S. Cytotoxic activities of compound 1–3 against HT-29 and MCF-7 cell lines.

Figure 1S. Structures of the isolated compounds 7–15 from Alternaria sp. sb23.

Figure 2S. Cytotoxic activities of compound 4–6 against HT-29 and MCF-7 cell lines.

Figure 3S. HRESIMS spectrum of alterchothecene A (1).

Figure 4S. IR spectrum of compound 1.

Figure 5S. UV spectrum of compound 1.

Figure 6S–11S. 1D and 2D NMR spectra of compound 1.

Figure 12S. HRESIMS spectrum of alterchothecene B (2).




Figure 21S. HRESIMS spectrum of alterchothecene C (3).




Figure 30S. HPLC-HRESIMS analysis of the crude extract.


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Table 1S. Cytotoxic activities of compound 1–3 against HT-29 and MCF-7 cell lines.

a positive control

Fig. 1S. Structures of the isolated compounds 7–15 from Alternaria sp. sb23.

Compounds Concentration (μM) Cell Viability (%)

HT-29 MCF-7

1 50 81.38 73.37

2 50 83.58 87.75

3 50 75.45 70.26

Doxorubicin hydrochloridea

3.125 59.94 52.87


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Fig. 2S. Cytotoxic activities of compound 4–6 against HT-29 and MCF-7 cell lines.


5

Fig. 3S. (+)-HRESIMS spectrum of alterchothecene A (1).

1 #23 RT: 0.22 AV: 1 NL: 1.34E9T: FTMS + c ESI Full ms [100.0000-1500.0000]

364 366 368 370 372 374 376 378 380 382 384m/z

0

50000000

100000000

150000000

200000000

250000000

300000000

350000000

400000000

450000000

500000000

550000000

600000000

650000000

700000000

750000000

800000000

850000000

900000000

950000000

1000000000

1050000000

1100000000

1150000000

1200000000

1250000000

1300000000

Re

lativ

e A

bu

nd

an

ce

373.16156

374.16479

374.30212 376.31784 381.38315371.14587368.20605 383.39883377.32108366.37244

372.14966

379.13516369.38297 384.40277363.33267 364.28271


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Fig. 4S. IR spectrum of compound 1.

3462

.85

2978

.34

2951

.64

2925

.63

2890

.01

1712

.25

1680

.25

1649

.20

1437

.69

1417

.38

1382

.44

1365

.90

1290

.99

1246

.00

1231

.11

1187

.67

1114

.58

1082

.84 10

35.7

810

08.4

299

0.18

952.

3693

5.48

907.

7087

9.92

817.

1879

0.25

772.

6575

2.26

697.

0665

5.11

629.

4859

6.11

581.

5854

4.02

526.

7151

1.65

495.

9747

0.48

447.

8043

3.92

419.

24

500100015002000250030003500

Wavenumber cm-1

4045

5055

6065

7075

Tra

nsm

ittan

ce [

%]

Fig. 5S. UV spectrum of compound 1.


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Fig. 6S. 1H NMR spectrum (400 MHz) of 1 in CDCl3.


8

Fig. 7S. 13C NMR and DEPT spectra (100 MHz) of 1 in CDCl3.


9

Fig. 8S. 1H–1H COSY spectrum of 1 in CDCl3.


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Fig. 9S. HSQC spectrum of 1 in CDCl3.

Fig. 10S. HMBC spectrum of 1 in CDCl3.


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Fig. 11S. NOESY spectrum of 1 in CDCl3.

Fig. 12S. (+)-HRESIMS spectrum of alterchothecene B (2).

GX-12 #11 RT: 0.30 AV: 1 NL: 3.17E7T: FTMS + p ESI Full ms [100.00-800.00]

100 150 200 250 300 350 400 450 500 550 600 650 700 750 800m/z

0

10

20

30

40

50

60

70

80

90

100

Re

lativ

e A

bun

da

nce

359.1836

695.3781

371.1834 709.3572

391.1733317.1730

259.1674 407.1682 727.3676524.2720 627.3515215.1435121.5956675.3515


12


3433

.32

2971

.54

2944

.77

2855

.31

1772

.26

1712

.69

1647

.01

1560

.28

1542

.47

1521

.63

1508

.24

1439

.64

1417

.08

1383

.56

1295

.72

1246

.74

1231

.07

1187

.37

1122

.19

1080

.94

1035

.24

999.

9699

0.70

930.

3492

0.02

874.

5885

0.55

817.

3178

7.96

777.

3174

9.99

739.

2369

6.24

650.

1862

9.45

590.

3756

5.72

553.

1952

7.26

517.

7849

9.92

481.

2346

2.85

435.

0940

9.68

500100015002000250030003500

Wavenumber cm-1

7075

8085

Tra

nsm

ittan

ce [

%]



13



14



15



16



17




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Fig. 21S. (+)-HRESIMS spectrum of alterchothecene C (3).

GX-8 #12 RT: 0.33 AV: 1 NL: 2.45E7T: FTMS + p ESI Full ms [100.00-800.00]

100 150 200 250 300 350 400 450 500 550 600 650 700 750 800m/z

0

10

20

30

40

50

60

70

80

90

100

Re

lativ

e A

bun

da

nce

415.1732

373.1628540.2896

275.1623477.1558

293.1729

491.1715347.1471 447.1630763.3312721.3204247.1310 619.3105

575.2841

201.1277117.8929


19


3450

.11

2962

.94

2925

.13

2853

.76

1737

.80

1716

.96

1680

.13

1647

.50

1629

.43

1581

.68

1511

.55

1439

.50

1415

.61

1367

.98

1238

.33

1183

.51

1114

.73

1076

.72

1034

.07

972.

41

879.

8686

1.10

846.

6981

7.59

751.

6673

3.15

715.

9369

6.39

657.

6864

2.96

624.

0560

4.31

585.

2755

0.29

500100015002000250030003500

Wavenumber cm-1

5055

6065

7075

80

Tra

nsm

ittan

ce [

%]



20



21



22



23



24



25


Fig. 30S. HPLC-HRESIMS analysis of the crude extract.

RT: 0.00 - 39.97

0 5 10 15 20 25 30 35Time (min)

0

10

20

30

40

50

60

70

80

90

100

Re

lativ

e A

bu

nd

an

ce

15.74

15.60

4.744.60 16.14

4.80 16.46

16.5414.805.4616.6914.5716.8313.53

10.34 17.3413.3310.02 21.0317.6912.47

9.625.69 21.6928.6122.569.21 31.5424.26 31.74 38.6638.488.86 29.620.21 1.45

NL:1.30E9TIC MS

质谱sb-2-3

a


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RT: 13.35 - 14.95

13.4 13.5 13.6 13.7 13.8 13.9 14.0 14.1 14.2 14.3 14.4 14.5 14.6 14.7 14.8 14.9Time (min)

0

10

20

30

40

50

60

70

80

90

100

110

120

130

140

150

160

Re

lativ

e A

bun

da

nce 14.14

NL:2.63E4m/z= 373.1583-373.1613 MS

质谱SB-2-3

RT: 0.00 - 39.97

0 5 10 15 20 25 30 35Time (min)

0

10

20

30

40

50

60

70

80

90

100

Rela

tive A

bundance

15.20 NL:2.09E4m/z= 359.1821-359.1851 MS

质谱SB-2-3alterchothecene B

(a): The total ionic chromatograms of crude extract; (b): selected ionic chromatograms at m/z

373.1583-373.1613 [M+Na]+ of extract for 1; (c): selected ionic chromatograms at m/z

359.1821-359.1851 [M+Na]+ of extract for 2.

compound 2

m/z 356.1826

[M+Na]+

c

b

compound 1

m/z 373.1585

[M+Na]+


Supporting Information · Structures of the isolated compounds 7–15 from Alternaria sp. sb23....

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Transcript of Supporting Information · Structures of the isolated compounds 7–15 from Alternaria sp. sb23....