10.1071/CH11036 © CSIRO 2011 Australian Journal of Chemistry, 2011, 64(6), 757–765

Structures and Anatomical Distribution of Oxygenated Diterpenes in

the Australian Nudibranch Chromodoris reticulata

Suciati, Lynette K. Lambert, Mary J. Garson

Accessory Publication

Figure S1. Structures of diterpenes 1-6 S2 Figure S2. 1H NMR spectra for diterpene 1 in CDCl3 and in C6D6 S3 Figure S3. 1H NMR spectra for diterpenes 2-3 in CDCl3 S4 Figure S4. 1H NMR spectra for diterpenes 4-5 in CDCl3 S5 Figure S5. 1H NMR spectrum for diterpene 6 in CDCl3 S6 Figure S6. HMBC and NOESY spectra of diterpene 1 in CDCl3 S7 Figure S7. HMBC and NOESY spectra of diterpene 2 in CDCl3 S8 Figure S8. HMBC and NOESY spectra of diterpene 3 in CDCl3 S9 Figure S9. HMBC and NOESY spectra of diterpene 4 in CDCl3 S10 Figure S10. HMBC and NOESY spectra of diterpene 5 in CDCl3 S11 Figure S11. HMBC and NOESY spectra of diterpene 6 in CDCl3 S12

S2

Figure S1. Structures of Diterpenes 1-6 Isolated from Chromodoris reticulata

S3

1.01.52.02.53.03.54.04.55.0 ppm

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 Figure S2. 1H NMR spectra of diterpene 1 in CDCl3 and in C6D6

1H NMR of Diterpene 1 (CDCl3)

1H NMR of Diterpene 1 (C6D6)

H-11 H-15β H-15α

X

X X

X

H-13

H-11

H-15

4.3 ppm

H-15 2.9 ppm

H-13

2.02.12.22.3 ppm

H-14 H-12β

H-12α

H-13 H-14

X

H-15β H-15α

3.63.7 ppm

H-13

2.32.4 ppm

H-12α

S4

1.01.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm

1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0 ppm

Figure S3. 1H NMR spectra of diterpenes 2-3 in CDCl3

1H NMR of Diterpene 2

1H NMR of Diterpene 3

H-15

H-17

H-15α H-15β

OMe OAc

H-13

X

H-17

X X

X

H-7

OAc

2.72.82.9 ppm

H-14 H-13

H-14 H-13

2.42.62.8 ppm

H-13

H-14 H-7β

S5

1.01.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm

1.52.02.53.03.54.04.55.05.56.0 ppm Figure S4. 1H NMR spectra of diterpenes 4-5 in CDCl3

1H NMR of Diterpene 4

1H NMR of Diterpene 5

H-17

X

X OMe

OAc

X H-7 X

H-15α H-15β H-13 H-14

2.52.62.72.8 ppm

H-13 H-14

H-15 H-17 H-7 H-3 H-6

17 OH

OAc

X

4.34.44.5 ppm

H-3 H-6

2.82.9 ppm

17 OH H-13 H-14

S6

12345678910 ppm

Figure S5. 1H NMR spectrum of diterpene 6 in CDCl3

1H NMR of Diterpene 6

H-6

H-17 H-15

H-7

X X OMe

X H-13

3.253.30 ppm

H-13

2.502.55 ppm

H-14 H-12β

S7

Figure S6. HMBC and NOESY spectra of diterpene 1 in CDCl3

HMBC (CDCl3, 500 MHz)

NOESY (CDCl3, 500 MHz)

S8

Figure S7. HMBC and NOESY spectra of diterpene 2 in CDCl3

HMBC (CDCl3, 500 MHz)

NOESY (CDCl3, 500 MHz)

S9

Figure S8. HMBC and NOESY spectra of diterpene 3 in CDCl3

HMBC (CDCl3, 500 MHz)

NOESY (CDCl3, 500 MHz)

S10

Figure S9. HMBC and NOESY spectra of diterpene 4 in CDCl3

NOESY (CDCl3, 500 MHz)

HMBC (CDCl3, 750 MHz)

S11

Figure S10. HMBC and NOESY spectra of diterpene 5 in CDCl3

HMBC (CDCl3, 500 MHz)

NOESY (CDCl3, 500 MHz)

S12

Figure S11. HMBC and NOESY spectra of diterpene 6 in CDCl3

HMBC (CDCl3, 900 MHz)

NOESY (CDCl3, 750 MHz)