Supplementary Information

Transcrição

1 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. Bara a a Faculdade de Farmácia Universidade Federal de Goiás, Rua 2, s/n, Setor Leste Universitário, Goiânia-GO, Brazil b Instituto de Química, Universidade Federal de Goiás, Campus Samambaia, Goiânia-GO, Brazil c Universidade Estadual de Goiás, Campus Anápolis de Ciências Exatas e Tecnológicas Henrique Santillo, BR-153, km 98, Anápolis-GO, Brazil d Instituto Federal de Educação, Ciência e Tecnologia do Espírito Santo, Campus Vila Velha, Avenida Ministro Salgado Filho, 0, Vila Velha-ES, Brazil e Laboratório de Petroleômica e Química Forense, Departamento de Química, Universidade Federal do Espírito Santo, Av. Fernando Ferrari, 514, Vitória-ES, Brazil f Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Av. do Café, s/n, -903 Ribeirão Preto-SP, Brazil Main roscopic data for compounds Figure S1. 1 H NMR rum (500 MHz, CDCl 3 ) of compound 1. * lucianoliao@ufg.br EXPNO 13 Date_ 1309 Time Hz sec RG K O MHz 9.85 usec MHz W

2 Figure S2. 1 H NMR rum (500 MHz, CDCl 3 ) of compound 1, region between EXPNO 13 Date_ 1309 Time Hz sec RG K O MHz 9.85 usec MHz W Figure S3. HSQC NMR contour map (500 MHz, CDCl 3 ) of compound EXPNO 0 Date_ 1309 Time hsqcetgp TD 96 NS Hz sec K D sec sec sec ZGOPTNS O MHz.00 usec usec O MHz CPDPRG[2 garp 13. usec P4 26. usec usec PLW W PLW W GPNAM[1] SMSQ10. GPNAM[2] SMSQ10. GPZ1.00 % GPZ2.12 % usec TD 256 O MHz Hz FnMO Echo-Antiecho MHz W QSINE MC2 echo-antiecho MHz W øžbkb

3 Figure S4. HMBC NMR contour map (500 MHz, CDCl 3 ) of compound 1. 1 EXPNO 300 Date_ 1309 Time 12. hmbcgplpndqf TD 96 NS Hz sec K CNST D2 D sec sec sec O MHz.00 usec O MHz 13. usec PLW W GPNAM[1] SMSQ10. GPNAM[2] SMSQ10. GPNAM[3] SMSQ10. GPZ % GPZ % GPZ % usec TD 256 O MHz Hz FnMO SI MHz W SINE MC MHz W 78 SI MHz W PC 1. Figure S5. 13 C NMR rum (500 MHz, CDCl 3 ) of compound EXPNO 2 Date_ Time PROBHD 5 mm BBO BB- zgpg30 TD NS DS Hz Hz sec 16.0 usec K sec 1 O MHz 8.88 usec PLW W O MHz CPDPRG[2 waltz16.00 usec PLW W PLW W PLW W

4 Figure S6. NOESY experiment (500 MHz, DMSO-d 6 ) for compound 1. Irradiation in hydrogen 5. Figure S7. NOESY experiment (500 MHz, DMSO-d 6 ) for compound 1. Irradiation in methyl group 17.

5 Figure S8. 1 H NMR rum (500 MHz, CDCl 3 ) of compound Composto 2 EXPNO 1 Date_ 828 Time NS Hz Hz sec RG usec K O MHz MHz W Figure S9. 1 H NMR rum (500 MHz, CDCl 3 ) of compound 2, region between Composto 2 EXPNO 1 Date_ 828 Time NS Hz Hz sec RG usec K O MHz MHz W

6 Figure S10. HSQC NMR contour map (500 MHz, CDCl 3 ) of compound Composto 2 EXPNO 0 Date_ 828 Time hsqcedetgpsisp2.3 TD Hz Hz sec RG usec K CNST sec D sec sec D21 D sec sec O MHz 7. usec 14. usec usec PLW W O MHz CPDPRG[2 garp 13. usec usec usec usec usec PLW W PLW W PLW W SPNAM[3] Crp,0.5,.1 SPOAL SPOFFS3 0 Hz SPW W SPNAM[7] Crpcomp.4 SPOAL SPOFFS7 0 Hz SPW W SPNAM[18 Crp_xfilt.2 SPOAL SPOFFS18 0 Hz SPW W GPNAM[1] SINE. GPNAM[2] SINE. GPNAM[3] SINE. GPNAM[4] SINE. GPZ1.00 % GPZ2.10 % GPZ % GPZ % usec usec TD 128 O MHz Hz FnMO Echo-Antiecho MHz W QSINE SI 512 MC2 echo-antiecho MHz W øžkkk Figure S11. HMBC NMR contour map (500 MHz, CDCl 3 ) of compound 2. 1 Composto 2 EXPNO 300 Date_ 831 Time hmbcgplpndqf TD 96 NS Hz Hz sec 71.0 usec K CNST sec D2 D sec sec sec O MHz 7. usec 14. usec PLW W O MHz 13. usec PLW W GPNAM[1] SINE. GPNAM[2] SINE. GPNAM[3] SINE. GPZ % GPZ % GPZ3.10 % usec TD 190 O MHz Hz FnMO SI MHz W SINE SI 512 MC MHz W

7 Figure S C NMR rum (500 MHz, CDCl 3 ) of compound 2. n m-sodh2 EXPNO 2 Date_ 1305 Time PROBHD 5 mm BBO BB- zgpg30 TD DS Hz Hz sec 16.0 usec K sec 1 O MHz 8.88 usec PLW W O MHz CPDPRG[2 waltz16.00 usec PLW W PLW W PLW W SI MHz W LB 1.00 Hz PC MHz W Figure S13. 1 H NMR rum (500 MHz, CDCl 3 ) of compound Composto 3 OK EXPNO 1 Date_ 823 Time Hz sec RG K O MHz 9.90 usec PLW W

8 Figure S14. 1 H NMR rum (500 MHz, CDCl 3 ) of compound 3, region between Composto 3 OK EXPNO 1 Date_ 823 Time Hz sec RG K O MHz 9.90 usec PLW W MHz W Composto 2 EXPNO Figure S15. HSQC NMR contour map (500 MHz, CDCl 3 ) of compound 3. Date_ 828 Time hsqcedetgpsisp2.3 TD Hz Hz sec RG usec K CNST sec D sec sec D21 D sec sec O MHz 7. usec 14. usec usec PLW W O MHz CPDPRG[2 garp 13. usec usec usec usec usec PLW W PLW W PLW W SPNAM[3] Crp,0.5,.1 SPOAL SPOFFS3 0 Hz SPW W SPNAM[7] Crpcomp.4 SPOAL SPOFFS7 0 Hz SPW W SPNAM[18 Crp_xfilt.2 SPOAL SPOFFS18 0 Hz SPW W GPNAM[1] SINE. GPNAM[2] SINE. GPNAM[3] SINE. GPNAM[4] SINE. GPZ1.00 % GPZ2.10 % GPZ % GPZ % usec usec TD 128 O MHz Hz FnMO Echo-Antiecho MHz W QSINE SI 512 MC2 echo-antiecho MHz W øžk kk

9 Composto 3 OK EXPNO Figure S16. HMBC NMR contour map (500 MHz, CDCl 3 ) of compound 3. Date_ 823 Time hmbcgplpndqf TD 96 NS Hz sec K CNST D2 D sec sec sec O MHz.00 usec O MHz 13. usec PLW W GPNAM[1] SMSQ10. GPNAM[2] SMSQ10. GPNAM[3] SMSQ10. GPZ % GPZ % GPZ % usec TD 256 O MHz Hz FnMO SI MHz W SINE MC MHz W