structures and anatomical distribution of oxygenated diterpenes … · hmbc and noesy spectra of...
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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)