FIDRES 0.091920 Hz RG 256 SWH 6024.096 Hz Supplementary … · 2017-09-22 · RG 256 DW 83.000 usec DE 6.50 usec TE 301.2 K D1 1.00000000 sec TD0 1 ===== CHANNEL f1 ===== SFO1 500.1324937

Supplementary Information

Isolation and Structural Characterization of Two New Furanoditerpenes from

Pterodon emarginatus (Fabaceae)

Leandra A. R. Oliveira,a Gerlon A. R. Oliveira,

b Geralda F. Lemes,

c Wanderson Romão,

d,e

Boniek G. Vaz,b Sérgio Albuquerque,

f Cristiana Gonçalez,

f Luciano M. Lião*

,b and

Maria Teresa F. Baraa

aFaculdade de Farmácia Universidade Federal de Goiás, Rua 240, s/n, Setor Leste Universitário,

74605-170 Goiânia-GO, Brazil

bInstituto de Química, Universidade Federal de Goiás, Campus Samambaia,

74690-900 Goiânia-GO, Brazil

cUniversidade Estadual de Goiás, Campus Anápolis de Ciências Exatas e Tecnológicas Henrique Santillo,

BR-153, km 98, 75001-970 Anápolis-GO, Brazil

dInstituto Federal de Educação, Ciência e Tecnologia do Espírito Santo, Campus Vila Velha,

Avenida Ministro Salgado Filho, 1000, 29106-010 Vila Velha-ES, Brazil

eLaboratório de Petroleômica e Química Forense, Departamento de Química,

Universidade Federal do Espírito Santo, Av. Fernando Ferrari, 514, 29075-910 Vitória-ES, Brazil

fFaculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo,

Av. do Café, s/n, 14040-903 Ribeirão Preto-SP, Brazil

Main spectroscopic data for compounds 1-3

Figure S1. 1H NMR spectrum (500 MHz, CDCl3) of compound 1.

______________________________

*e-mail: [email protected]

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

1.450

1.461

1.474

1.492

1.543

1.549

1.604

1.608

1.649

1.687

1.738

1.742

1.761

1.765

1.768

2.003

2.025

2.028

2.049

2.051

2.187

2.420

2.441

2.454

2.474

2.475

2.598

2.612

2.632

2.645

3.785

3.803

3.806

3.824

4.106

4.129

4.207

4.230

5.341

5.359

5.364

5.383

6.420

6.423

7.253

7.257

Current Data ParametersNAME n m-sodh1

EXPNO 13PROCNO 1

F2 - Acquisition Parameters

Date_ 20130409Time 12.18

INSTRUM spectPROBHD 5 mm TBI 1H/13

PULPROG zg30

TD 65536

SOLVENT CDCl3NS 16

DS 0SWH 6024.096 Hz

FIDRES 0.091920 Hz

AQ 5.4394879 secRG 256DW 83.000 usec

DE 6.50 usecTE 301.2 K

D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========SFO1 500.1324937 MHz

NUC1 1HP1 9.85 usec

PLW1 11.38700008 W

F2 - Processing parametersSI 65536

SF 500.1300109 MHzWDW EM

SSB 0LB 0 Hz

GB 0PC 1.00

ppm

7.253

7.257

ppm

2.003

2.025

2.028

2.049

2.051

ppm

4.106

4.129

4.207

4.230

ppm

6.420

6.423

5.4 ppm

5.341

5.359

5.364

5.383

ppm

3.785

3.803

3.806

3.824

2.52.6 ppm

2.420

2.441

2.454

2.474

2.475

2.598

2.612

2.632

2.645

Figure S2. 1H NMR spectrum (500 MHz, CDCl3) of compound 1, region between 1.0-1.8.

Figure S3. HSQC NMR contour map (500 MHz, CDCl3) of compound 1.

1.01.11.21.31.41.51.61.71.8 ppm

1.038

1.051

1.090

1.111

1.136

1.269

1.437

1.450

1.461

1.474

1.492

1.543

1.549

1.604

1.608

1.649

1.687

1.738

1.742

1.761

1.765

1.768


EXPNO 13PROCNO 1


Date_ 20130409Time 12.18


PULPROG zg30

TD 65536

SOLVENT CDCl3NS 16

DS 0SWH 6024.096 Hz

FIDRES 0.091920 Hz

AQ 5.4394879 secRG 256DW 83.000 usec


D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========SFO1 500.1324937 MHz

NUC1 1HP1 9.85 usec

PLW1 11.38700008 W



SSB 0LB 0 Hz

GB 0PC 1.00

ppm

1234567 ppm

160

140

120

100

80

60

40

20

0

Current Data Parameters

NAME n m-sodh1

EXPNO 200

PROCNO 1


Date_ 20130409

Time 14.21

INSTRUM spect

PROBHD 5 mm TBI 1H/13

PULPROG hsqcetgp

TD 4096

SOLVENT CDCl3

NS 20DS 16

SWH 6024.096 Hz

FIDRES 1.470727 Hz

AQ 0.3399680 sec

RG 912

DW 83.000 usec

DE 6.50 usec

TE 301.4 K

CNST2 145.0000000

D0 0.00000300 sec

D1 1.00000000 sec

D4 0.00172414 sec

D11 0.03000000 sec

D16 0.00020000 secIN0 0.00001330 sec

ZGOPTNS

======== CHANNEL f1 ========

SFO1 500.1324937 MHz

NUC1 1H

P1 10.00 usec

P2 20.00 usec

P28 1000.00 usec

PLW1 11.38700008 W

======== CHANNEL f2 ========

SFO2 125.7671682 MHz

NUC2 13C

CPDPRG[2 garpP3 13.40 usec

P4 26.80 usec

PCPD2 70.00 usec

PLW2 88.66999817 W

PLW12 3.24930000 W

====== GRADIENT CHANNEL =====

GPNAM[1] SMSQ10.100

GPNAM[2] SMSQ10.100

GPZ1 80.00 %

GPZ2 20.12 %

P16 1000.00 usec

F1 - Acquisition parameters

TD 256

SFO1 125.7672 MHz

FIDRES 146.851501 Hz

SW 298.917 ppm

FnMODE Echo-Antiecho

F2 - Processing parameters

SI 1024

SF 500.1300058 MHz

WDW QSINE

SSB 2

LB 0 Hz

GB 0

PC 1.00


SI 1024

MC2 echo-antiecho

SF 125.7577890 MHz

WDW øžb��kb�

SSB 2

LB 0 Hz

GB 0

Figure S4. HMBC NMR contour map (500 MHz, CDCl3) of compound 1.

Figure S5. 13

C NMR spectrum (500 MHz, CDCl3) of compound 1.

ppm

12345678 ppm

20

40

60

80

100

120

140

160

180


NAME n m-sodh1

EXPNO 300

PROCNO 1

F2 - Acquisition ParametersDate_ 20130409

Time 12.20

INSTRUM spect


PULPROG hmbcgplpndqf

TD 4096

SOLVENT CDCl3NS 20

DS 16

SWH 6024.096 Hz

FIDRES 1.470727 Hz

AQ 0.3399680 sec

RG 912DW 83.000 usec

DE 6.50 usec

TE 301.2 K

CNST2 145.0000000

CNST13 10.0000000

D0 0.00000300 sec

D1 1.00000000 secD2 0.00344828 sec

D6 0.05000000 sec

D16 0.00020000 sec

IN0 0.00001330 sec

======== CHANNEL f1 ========SFO1 500.1324937 MHz

NUC1 1H

P1 10.00 usec

P2 20.00 usec

PLW1 11.38700008 W

======== CHANNEL f2 ========SFO2 125.7703437 MHz

NUC2 13C

P3 13.40 usec

PLW2 88.66999817 W

====== GRADIENT CHANNEL =====GPNAM[1] SMSQ10.100

GPNAM[2] SMSQ10.100

GPNAM[3] SMSQ10.100

GPZ1 70.00 %

GPZ2 30.00 %

GPZ3 65.15 %

P16 1000.00 usec


TD 256

SFO1 125.7703 MHz


SW 298.910 ppmFnMODE QF


SI 2048

SF 500.1300000 MHz

WDW SINE

SSB 0LB 0 Hz

GB 0

PC 1.00


SI 1024

MC2 QFSF 125.7577890 MHz

WDW

SSB 0

LB 0 Hz

GB 0

180 160 140 120 100 80 60 40 20 ppm

16.35

17.99

20.90

21.93

22.54

25.90

30.61

36.96

38.37

38.71

39.53

46.93

49.47

54.96

67.04

72.62

75.81

77.46

107.25

123.94

141.88

148.25

171.23

172.59


EXPNO 2PROCNO 1


Date_ 20130415Time 11.42

INSTRUM spectPROBHD 5 mm BBO BB-1H

PULPROG zgpg30TD 32768

SOLVENT CDCl3NS 10728

DS 2SWH 29761.904 HzFIDRES 0.908261 Hz

AQ 0.5505024 secRG 912

DW 16.800 usecDE 6.50 usec

TE 298.3 KD1 0.50000000 sec

D11 0.03000000 secTD0 1

======== CHANNEL f1 ========

SFO1 125.7703643 MHzNUC1 13C

P1 8.88 usecPLW1 55.94699860 W

======== CHANNEL f2 ========SFO2 500.1320005 MHz

NUC2 1HCPDPRG[2 waltz16

PCPD2 80.00 usecPLW2 14.40799999 W

PLW12 0.50652999 WPLW13 0.32418001 W


SI 32768SF 125.7577824 MHz

WDW EMSSB 0LB 0 Hz

GB 0PC 1.40

78 ppm

75.807

77.460

ppm

36.957

38.366

38.715

39.534

22 ppm

20.897

21.929

22.541

Figure S6. NOESY experiment (500 MHz, DMSO-d6) for compound 1. Irradiation in hydrogen 5.

Figure S7. NOESY experiment (500 MHz, DMSO-d6) for compound 1. Irradiation in methyl group 17.



7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

1.228

1.235

1.254

1.261

1.263

1.277

1.300

1.387

1.391

1.414

1.418

1.453

1.468

1.488

1.526

1.553

1.683

1.712

2.018

2.040

2.043

2.064

2.166

2.415

2.436

2.448

2.469

2.584

2.597

2.618

2.631

3.831

3.850

3.870

5.304

5.309

5.327

5.332

5.350

6.420

6.423

7.255

7.259

Current Data ParametersNAME Composto 2

EXPNO 1PROCNO 1


Date_ 20120828Time 14.25


PULPROG zg30

TD 65536

SOLVENT CDCl3NS 32

DS 0SWH 9375.000 Hz

FIDRES 0.143051 Hz

AQ 3.4952533 secRG 144DW 53.333 usec


D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========SFO1 500.1328556 MHz

NUC1 1HP1 10.00 usec

PLW1 11.38700008 W



SSB 0LB 0 Hz

GB 0PC 1.00

ppm

7.255

7.259

ppm

6.420

6.423

5.35 ppm

5.304

5.309

5.327

5.332

5.350

2.52.6 ppm

2.415

2.436

2.448

2.469

2.584

2.597

2.618

ppm

3.831

3.850

3.870

2.05 ppm

2.018

2.040

2.043

2.064

1.001.051.101.151.201.251.301.351.401.451.501.551.601.651.701.75 ppm

0.959

0.986

0.994

1.013

1.018

1.059

1.064

1.087

1.201

1.209

1.228

1.235

1.254

1.261

1.263

1.277

1.300

1.387

1.391

1.414

1.418

1.453

1.468

1.488

1.526

1.553

1.683

1.712

Current Data ParametersNAME Composto 2

EXPNO 1PROCNO 1


Date_ 20120828Time 14.25


PULPROG zg30

TD 65536

SOLVENT CDCl3NS 32

DS 0SWH 9375.000 Hz

FIDRES 0.143051 Hz

AQ 3.4952533 secRG 144DW 53.333 usec


D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========SFO1 500.1328556 MHz


PLW1 11.38700008 W



SSB 0LB 0 Hz

GB 0PC 1.00



ppm

1234567 ppm

160

140

120

100

80

60

40

20

0


NAME Composto 2EXPNO 200

PROCNO 1


Time 14.29


PULPROG hsqcedetgpsisp2.3

TD 4096

SOLVENT CDCl3NS 16

DS 16

SWH 9375.000 HzFIDRES 2.288818 Hz

AQ 0.2184533 secRG 2050

DW 53.333 usec


CNST2 145.0000000CNST17 -0.5000000

D0 0.00000300 secD1 1.50000000 sec

D4 0.00172414 sec

D11 0.03000000 secD16 0.00020000 sec

D21 0.00344828 sec

D24 0.00086207 sec

IN0 0.00001590 sec

======== CHANNEL f1 ========

SFO1 500.1328556 MHzNUC1 1H

P1 7.40 usecP2 14.80 usec

P28 1000.00 usecPLW1 20.35199928 W

======== CHANNEL f2 ========

SFO2 125.7675981 MHz

NUC2 13CCPDPRG[2 garp

P3 13.40 usecP14 500.00 usec

P24 2000.00 usecP31 1900.00 usec

PCPD2 70.00 usec

PLW0 -1.00000000 WPLW2 88.66999817 W

PLW12 3.24930000 W

SPNAM[3] Crp60,0.5,20.1

SPOAL3 0.500

SPOFFS3 0 HzSPW3 24.32600021 W

SPNAM[7] Crp60comp.4SPOAL7 0.500

SPOFFS7 0 HzSPW7 24.32600021 W

SPNAM[18 Crp60_xfilt.2

SPOAL18 0.500SPOFFS18 0 Hz

SPW18 5.82889986 W

====== GRADIENT CHANNEL =====GPNAM[1] SINE.100

GPNAM[2] SINE.100

GPNAM[3] SINE.100GPNAM[4] SINE.100

GPZ1 80.00 %

GPZ2 20.10 %

GPZ3 11.00 %GPZ4 -5.00 %

P16 1000.00 usec

P19 600.00 usec

F1 - Acquisition parametersTD 128

SFO1 125.7676 MHzFIDRES 245.676102 Hz

SW 250.037 ppm

FnMODE Echo-Antiecho


SF 500.1300047 MHz

WDW QSINE

SSB 2

LB 0 HzGB 0

PC 1.00


SI 512MC2 echo-antiecho

SF 125.7577569 MHzWDW øžK��kK�

SSB 2LB 0 Hz

GB 0

ppm

12345678 ppm

20

40

60

80

100

120

140

160

180


NAME Composto 2

EXPNO 300

PROCNO 1


Time 15.33

INSTRUM spect



TD 4096

SOLVENT CDCl3NS 8

DS 16

SWH 7002.801 Hz

FIDRES 1.709668 Hz

AQ 0.2924544 sec


DE 10.00 usec

TE 301.2 K

CNST2 145.0000000

CNST13 8.0000000

D0 0.00000300 sec

D1 1.50000000 secD2 0.00344828 sec

D6 0.06250000 sec

D16 0.00020000 sec

IN0 0.00001890 sec

======== CHANNEL f1 ========SFO1 500.1324985 MHz

NUC1 1H

P1 7.40 usec

P2 14.80 usec

PLW1 20.35168076 W

======== CHANNEL f2 ========SFO2 125.7703648 MHz

NUC2 13C

P3 13.40 usec

PLW2 88.66959381 W

====== GRADIENT CHANNEL =====GPNAM[1] SINE.100

GPNAM[2] SINE.100

GPNAM[3] SINE.100

GPZ1 50.00 %

GPZ2 30.00 %

GPZ3 40.10 %

P16 1000.00 usec


TD 190

SFO1 125.7704 MHz


SW 210.344 ppmFnMODE QF


SI 2048

SF 500.1300071 MHz

WDW SINE

SSB 0LB 0 Hz

GB 0

PC 1.00


SI 512

MC2 QFSF 125.7577890 MHz

WDW

SSB 0

LB 0 Hz

GB 0

Figure S12. 13

C NMR spectrum (500 MHz, CDCl3) of compound 2.


2030405060708090100110120130140150160170 ppm

18.08

21.73

22.23

22.40

25.57

30.41

32.90

36.11

39.45

43.31

46.74

49.58

54.31

72.65

75.80

76.72

106.98

107.44

123.71

141.24

141.62

148.43

172.00


EXPNO 2PROCNO 1


Date_ 20130405Time 10.45

INSTRUM spectPROBHD 5 mm BBO BB-1H

PULPROG zgpg30TD 32768

SOLVENT CDCl3NS 16296DS 2

SWH 29761.904 HzFIDRES 0.908261 Hz

AQ 0.5505024 secRG 912


TE 298.3 KD1 0.50000000 sec

D11 0.03000000 secTD0 1

======== CHANNEL f1 ========

SFO1 125.7703643 MHzNUC1 13CP1 8.88 usec

PLW1 55.94699860 W

======== CHANNEL f2 ========SFO2 500.1320005 MHz

NUC2 1HCPDPRG[2 waltz16

PCPD2 80.00 usecPLW2 14.40799999 W

PLW12 0.50652999 WPLW13 0.32418001 W


SI 32768SF 125.7578089 MHzWDW EM

SSB 0LB 1.00 Hz

GB 0PC 1.40

77 ppm

75

.80

1

76

.72

1

ppm

21

.72

6

22

.22

9

1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0 ppm

1.301

1.360

1.387

1.435

1.447

1.459

1.468

1.530

1.557

1.668

1.700

1.764

1.784

2.087

2.344

2.364

2.387

2.406

2.420

2.425

2.620

2.630

2.652

2.663

3.286

3.306

3.325

3.345

3.379

3.396

3.703

5.196

5.215

5.219

5.238

6.138

6.142

7.214

Current Data ParametersNAME Composto 3 OK

EXPNO 1PROCNO 1


Date_ 20120823Time 11.10

INSTRUM spectPROBHD 5 mm TBI 1H/13PULPROG zg30

TD 65536SOLVENT CDCl3

NS 16DS 0

SWH 6024.096 HzFIDRES 0.091920 Hz

AQ 5.4394879 secRG 114

DW 83.000 usecDE 6.50 usecTE 294.7 K

D1 1.00000000 secTD0 1

======== CHANNEL f1 ========

SFO1 500.1325072 MHzNUC1 1H

P1 9.90 usecPLW1 8.48398972 W



SSB 0LB 0 Hz

GB 0PC 1.00

ppm

6.138

6.142

ppm

5.196

5.215

5.219

5.238

3.4 ppm

3.286

3.306

3.325

3.345

3.379

3.396

ppm

2.620

2.630

2.652

2.663

ppm

7.214

2.4 ppm

2.364

2.387

2.406

2.420

2.425



0.80.91.01.11.21.31.41.51.61.71.8 ppm

0.919

0.957

0.964

0.983

0.991

1.003

1.056

1.176

1.183

1.203

1.210

1.230

1.237

1.278

1.301

1.360

1.387

1.435

1.447

1.459

1.468

1.530

1.557

1.668

1.700

1.764

1.784

Current Data ParametersNAME Composto 3 OK

EXPNO 1PROCNO 1


Date_ 20120823Time 11.10


PULPROG zg30

TD 65536

SOLVENT CDCl3NS 16

DS 0SWH 6024.096 Hz

FIDRES 0.091920 Hz

AQ 5.4394879 secRG 114DW 83.000 usec


D1 1.00000000 sec

TD0 1

======== CHANNEL f1 ========SFO1 500.1325072 MHz

NUC1 1HP1 9.90 usec

PLW1 8.48398972 W



SSB 0LB 0 Hz

GB 0PC 1.00

ppm

1.01.52.02.53.03.54.04.55.05.56.06.57.0 ppm

140

120

100

80

60

40

20


NAME Composto 2

EXPNO 200PROCNO 1


Time 14.29

INSTRUM spect

PROBHD 5 mm TBI 1H/13PULPROG hsqcedetgpsisp2.3

TD 4096

SOLVENT CDCl3NS 16

DS 16

SWH 9375.000 Hz

FIDRES 2.288818 HzAQ 0.2184533 sec

RG 2050


TE 296.2 K

CNST2 145.0000000

CNST17 -0.5000000D0 0.00000300 sec

D1 1.50000000 sec

D4 0.00172414 secD11 0.03000000 sec

D16 0.00020000 sec

D21 0.00344828 sec

D24 0.00086207 secIN0 0.00001590 sec

======== CHANNEL f1 ========SFO1 500.1328556 MHz

NUC1 1H

P1 7.40 usec

P2 14.80 usecP28 1000.00 usec

PLW1 20.35199928 W

======== CHANNEL f2 ========

SFO2 125.7675981 MHz

NUC2 13C

CPDPRG[2 garpP3 13.40 usec

P14 500.00 usec

P24 2000.00 usecP31 1900.00 usec

PCPD2 70.00 usec

PLW0 -1.00000000 W

PLW2 88.66999817 WPLW12 3.24930000 W

SPNAM[3] Crp60,0.5,20.1


SPW3 24.32600021 W

SPNAM[7] Crp60comp.4


SPW7 24.32600021 W

SPNAM[18 Crp60_xfilt.2SPOAL18 0.500

SPOFFS18 0 Hz

SPW18 5.82889986 W


GPNAM[1] SINE.100

GPNAM[2] SINE.100GPNAM[3] SINE.100

GPNAM[4] SINE.100

GPZ1 80.00 %

GPZ2 20.10 %GPZ3 11.00 %

GPZ4 -5.00 %

P16 1000.00 usecP19 600.00 usec


TD 128SFO1 125.7676 MHz


SW 250.037 ppmFnMODE Echo-Antiecho


SI 1024SF 500.1300047 MHz

WDW QSINE

SSB 2LB 0 Hz

GB 0

PC 1.00


SI 512

MC2 echo-antiechoSF 125.7577569 MHz

WDW øžK��kK�

SSB 2LB 0 Hz

GB 0


ppm

1.01.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm

20

40

60

80

100

120

140

160

180

200

220


NAME Composto 3 OKEXPNO 300

PROCNO 1


Date_ 20120823Time 14.18



TD 4096SOLVENT CDCl3

NS 20DS 16

SWH 6024.096 Hz

FIDRES 1.470727 Hz

AQ 0.3399680 sec


DE 6.50 usec

TE 294.8 KCNST2 145.0000000

CNST13 10.0000000D0 0.00000300 sec

D1 1.00000000 sec

D2 0.00344828 secD6 0.05000000 sec

D16 0.00020000 secIN0 0.00001790 sec

======== CHANNEL f1 ========SFO1 500.1325072 MHz


P2 20.00 usec

PLW1 11.38700008 W

======== CHANNEL f2 ========SFO2 125.7703437 MHz

NUC2 13C

P3 13.40 usecPLW2 88.66999817 W


GPNAM[1] SMSQ10.100

GPNAM[2] SMSQ10.100GPNAM[3] SMSQ10.100

GPZ1 70.00 %GPZ2 30.00 %

GPZ3 65.15 %

P16 1000.00 usec


TD 256

SFO1 125.7703 MHz

FIDRES 109.113129 HzSW 222.095 ppm

FnMODE QF


SI 2048SF 500.1300218 MHz

WDW SINESSB 0

LB 0 HzGB 0

PC 1.00


SI 1024MC2 QF

SF 125.7577890 MHz

WDWSSB 0

LB 0 HzGB 0

Documents

FIDRES 0.091920 Hz RG 256 SWH 6024.096 Hz Supplementary … · 2017-09-22 · RG 256 DW 83.000 usec DE 6.50 usec TE 301.2 K D1 1.00000000 sec TD0 1 ===== CHANNEL f1 ===== SFO1 500.1324937