Chromolactol, an Oxygenated Diterpene from the Indo-Pacific Nudibranch Goniobranchus
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1 Chromolactol, an Oxygenated Diterpene from the Indo-Pacific Nudibranch Goniobranchus coi: Spectroscopic and Computational Studies Ariyanti S. Dewi A,B, Gregory K. Pierens C, Karen L. Cheney D, Joanne T. Blanchfield A, and Mary J. Garson A,E A School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD 4072, Australia B Research Center for Marine and Fisheries Product Processing and Biotechnology, Ministry of Marine Affairs and Fisheries, Jakarta 10260, Indonesia C Centre for Advanced Imaging, The University of Queensland, Brisbane QLD 4072, Australia D School of Biological Sciences, The University of Queensland, Brisbane QLD 4072, Australia E Corresponding author. m.garson@uq.edu.au Table of contents Figure S1. Structures of stereoisomers of chromolactol... S2 Figure S2. Image of Goniobranchus coi... S2 Figure S3. H NMR spectrum of 1 (500 MHz, CDCl 1 3).... S3 Figure S4. H NMR spectrum of 1 (500 MHz, CDCl 1 3) down field region ( ppm).... S4 Figure S5. H NMR spectrum of 1 (500 MHz, CDCl 1 3) up field region (0-2.5 ppm).... S5 Figure S6. HSQC spectrum of 1 (700 MHz, CDCl 3).... S6 Figure S7. HMBC spectrum of 1 (700 MHz, CDCl 3).... S7 Figure S8. gcosy spectrum of 1 (700 MHz, CDCl 3).... S8 Figure S9. NOESY spectrum of 1 (700 MHz, CDCl 3).... S9 Figure S10. Overlay of lowest energy conformers of stereoisomers 1a and 1b of chromolactol... S10 Table S1. H NMR experimental and calculated chemical shifts... S11 1 Table S2. C NMR experimental and calculated chemical shifts... S11 13 Table S3. Computed DP4 probabilities for compounds 1a and 1b... S12 XYZ coordinates for isomer 1a... S13 XYZ coordinates for isomer 1b... S18 Table S4. Computed DP4 probabilities for cheloviolenes A and B... S23 S1
2 H HO H H H 13 O 11 H O O H HO H H H O H O O 1a 1b Figure S1. Structures of candidate diastereomers of chromolactol Figure S2. Image of Goniobranchus coi S2
3 Figure S3. 1 H NMR spectrum of 1 (500 MHz, CDCl 3). S3
4 Figure S4. 1 H NMR spectrum of 1 (500 MHz, CDCl 3) down field region ( ppm). S4
5 Figure S5. 1 H NMR spectrum of 1 (500 MHz, CDCl 3) up field region (0-2.5 ppm). S5
6 Figure S6. HSQC spectrum of 1 (700 MHz, CDCl 3). S6
7 Figure S7. HMBC spectrum of 1 (700 MHz, CDCl 3). S7
8 Figure S8. gcosy spectrum of 1 (700 MHz, CDCl 3). S8
9 Figure S9. NOESY spectrum of 1 (700 MHz, CDCl 3). S9
10 Figure S10. Overlay of lowest energy conformers of stereoisomers 1a and 1b of chromolactol 1a 1b S10
11 Table S1. 1 H NMR experimental and calculated chemical shifts # expt 1a 1b 1a b a b a b a b a b a b a b Table S2. 13 C NMR experimental and calculated chemical shifts # expt 1a 1b S11
12 Table S3. Computed DP4 probabilities for compounds 1a and 1b 1a 1b DP4 (H data) 45.8% 54.2% DP4 (C data) 68.1% 31.9% DP4 (all data) 64.3% 35.7% S12
13 XYZ coordinates for isomer 1a chromolactol1a % C C H H O H O C C C C H H H H O O C C H H C C C H H H H H C C C C C C H H H H H H H C H H S13
14 H C H H H C H H H chromolactol1a % C C H H O H O C C C C H H H H O O C C H H C C C H H H H H C C C C C C H H H H S14
15 H H H C H H H C H H H C H H H chromolactol1a % C C H H O H O C C C C H H H H O O C C H H C C C H H H H H C C C C S15
16 C C H H H H H H H C H H H C H H H C H H H chromolactol1a % C C H H O H O C C C C H H H H O O C C H H C C C H H H S16
17 H H C C C C C C H H H H H H H C H H H C H H H C H H H S17
18 XYZ coordinates for isomer 1b chromolactol1b % C C H H O H O C C C C H H H H O O C C H H C C C H H H H H C C C C C C H H H H H H H C H H S18
19 H C H H H C H H H chromolactol1b % C C H H O H O C C C C H H H H O O C C H H C C C H H H H H C C C C C C H H H H S19
20 H H H C H H H C H H H C H H H chromolactol1b % C C H H O H O C C C C H H H H O O C C H H C C C H H H H H C C C C S20
21 C C H H H H H H H C H H H C H H H C H H H chromolactol1b % C C H H O H O C C C C H H H H O O C C H H C C C H H H S21
22 H H C C C C C C H H H H H H H C H H H C H H H C H H H S22
23 Table S4. Computed DP4 probabilities for cheloviolenes A and B Cheloviolene A Cheloviolene B DP4 (H data) 83.1% 16.9% DP4 (C data) 44.3% 55.7% DP4 (all data) 79.6% 20.4% S23
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