Supporting Information for. Update of spectroscopic data for 4-hydroxyldictyolactone and dictyol E isolated from a Halimeda stuposa - Dictyota
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1 1 Supporting Information for Update of spectroscopic data for 4-hydroxyldictyolactone and dictyol E isolated from a Halimeda stuposa - Dictyota sp. Assemblage Simon P. B. Ovenden, Jonathan L. Nielson, Catherine H. Liptrot, Richard H. Willis, Dianne M. Tapiolas, Anthony D. Wright and Cherie A. Motti, * Australian Institute of Marine Science, PMB no. 3, Townsville MC, Townsville, 4810, Australia Current address: Defence Science & Technology Organisation, 506 Lorimer St. Fishermans Bend, Victoria, 3207, Australia Current address: ACD Labs UK, Building A, Trinity Court, Wokingham Road, Bracknell, Berkshire, RG42 1PL, England Current address: James Cook University, Townsville, QLD 4811, Australia. Current address: University of Hawaii at Hilo, College of Pharmacy, 34 Rainbow Drive, Hilo, Hawaii 96720, USA. * To whom correspondence should be addressed: Tel.: Fax.: c.motti@aims.gov.au. Defence Science & Technology Organisation, ACD Labs UK, James Cook University, Australian Institute of Marine Science, University of Hawaii at Hilo.
2 2 Table of Contents. Page No Figure S1. 1 H NMR spectrum (300 MHz) of 4-hydroxydictyolactone (1) in CDCl Figure S2. 13 C NMR spectrum (75 MHz) of 4-hydroxydictyolactone (1) in CDCl Figure S3. COSY spectrum (300 MHz) of 4-hydroxydictyolactone (1) in CDCl Figure S4. HSQC spectrum (300 MHz) of 4-hydroxydictyolactone (1) in CDCl Figure S5. HMBC spectrum (300 MHz) of 4-hydroxydictyolactone (1) in CDCl Figure S6. 1 H NMR spectrum (300 MHz) of dictyol E (2) in CDCl Figure S7. COSY spectrum (300 MHz) of dictyol E (2) in CDCl Figure S8. HSQC spectrum (300 MHz) of dictyol E (2) in CDCl Figure S9. HMBC spectrum (300 MHz) of dictyol E (2) in CDCl Table S1. 1 H and 13 C NMR data (300 MHz and 75 MHz, CDCl 3 ) for the trans- and cis-conformers of 4-hydroxydictyolactone (1). 12 Table S2. Comparison of calculated dihedral angles from the 16 possible stereoisomers of the H-3 C-20 trans-conformers and the corresponding cis-conformers of 1 with observed 1 H- 1 H couplings from the 1 H NMR. * indicates those stereoisomers/conformers that match the 1 H NMR data
3 S1. 1 H NMR of 1 3
4
5 S3. COSY NMR of f2 (ppm)
6 S4. HSQC NMR of f2 (ppm)
7 S5. HMBC NMR of f2 (ppm)
8 S6. 1 H NMR of E E+08 E E+08 E E+08 E E+08 E+08 E E+00 -E
9 S7. COSY NMR of f2 (ppm)
10 S8. HSQC NMR of f2 (ppm)
11 S9. HMBC NMR of f2 (ppm)
12 12 Table S1. 1 H and 13 C NMR data (300 MHz and 75 MHz, CDCl 3 ) for the trans- and cis-conformers of 4-hydroxydictyolactone (1). Trans-conformer (major compound) Cis-conformer (minor compound) No. 13 C H C H COSY ghmbc δ (m) δ (m, J Hz) δ (m) δ (m, J Hz) (s) (d) 3.40 (1H, dd, 7.8, 1.2) H 2-18 C-1, C-3, C-4, C-9, C-10, C (d) 3.86 (m) 3 5 (d) 4 (1H, br s) C-1, C-2, C-4, C-5, C-10, C-11, C-17, C (br s) (d) 4.30 (1H, dd, 4.2, 2.2) H a -5, H b -5 C-2, C (d) 4.22 (m) (t) 2.33 (1H, dd, 1, 2.2) 2.18 (1H, dd, 1, 4.2) H-4, H b -5 H-4, H a -5 C-3, C-4, C-6, C-7, C-20 C-3, C-4, C-6, C-7, C-20 ND 2.81 (m) 2.32 (m) (s) (d) 5.32 (1H, ddq, 11.4, 4.2, 0.7) H a -8, H b -8, H 3-20 C-5, C (d) 5.61 (m) (t) 3.20 (1H, dddd, 17.5, 11.4, 2.2, 2.2) 2.98 (1H, ddd, 17.5, 7.4, 4.2) H-7, H b -8, H-9 H-7, H a -8, H-9 C-1, C-6, C-7, C-9 C-1, C-6, C-7, C-9 ND 3.21 (m) 2.66 (m) (d) 6.94 (1H, dt, 7.4, 2.2) H a -8, H b -8 C-2, C-7, C-8, C (d) 6.88 (dt, 8.0, 3.3) (d) 1.71 (1H, m) H 3-17 C-2, C-3, C-4, C-11, C-12, C (d) 1.72 (m) (t) 1.19 (2H, m) H 2-12 ND (t) 1.93 (2H, m) H 2-11, H-13 C-14 ND (d) 2 (1H, t hept, 7.2, 1.4) H 2-12, H 3-15, H 3-16 C-15, C (d) 7 (1H, t hept, 7.2, 1.4) (s) (q) 1.57 (3H, s) H-13 C-13, C-14, C (q) 1.59 (3H, s) (q) 1.66 (3H, s) H-13 C-13, C-14, C (q) 1.74 (3H, s) (q) 7 (3H, d, 6.7) H-10 C-3, C-10, C (q) 6 (d, 6.7) (t) 4.45 (1H, dd, 9.7, 1.2) 4.10 (1H, dd, 9.7, 7.8) H-2, H b -18 H-2, H a -18 C-1, C-2, C-3, C-19 C (t) 4.41 (dd, 9.6, 1.6) 4.14 (dd, 9.6, 7.3) (s) ND (q) 1.90 (3H, br d, 0.7) H-7 C-5, C-6, C (q) 1.59 (br s) ND = Not detected
13 13 Table S2. Comparison of calculated dihedral angles from the 16 possible stereoisomers of the H-3 C-20 trans-conformers and the corresponding cis-conformers of 1 with observed 1 H- 1 H couplings from the 1 H NMR. * indicates those stereoisomers/conformers that match the 1 H NMR data. C-2, C-3, C-4, C-10 configuration 1 H- 1 H correlation Calculated dihedral angle Φ Calculated J (Hz) Relevant observed 1 H- 1 H couplings SSSS trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. SSSS cis H2-C2-C3-H NA H3-C3-C4-H NA H3-C3-C10-H NA SSSR trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. SSSR cis H2-C2-C3-H NA H3-C3-C4-H NA H3-C3-C10-H NA *SSRR trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. SSRR cis H2-C2-C3-H NA H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H NA SRRR trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. SRRR cis H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H NA *SSRS trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H No observed coupling: H-3 (br s)
14 H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. SSRS cis H2-C2-C3-H NA H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H NA SRRS trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. SRRS cis H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. SRSR-trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. SRSR-cis H2-C2-C3-H H3-C3-C4-H4 34 NA H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. SRSS trans H2-C2-C3-H NA H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. SRSS cis H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. RSRS trans H2-C2-C3-H NA H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. RSRS cis H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H NA *RRSR trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. RRSR cis H2-C2-C3-H NA H3-C3-C4-H No observed coupling: H-3 (br s) 14
15 H3-C3-C10-H NA RSSR trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. RSSR cis H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H NA RSRR trans H2-C2-C3-H NA H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H NA RSRR cis H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H NA RRRR trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. RRRR cis H2-C2-C3-H NA H3-C3-C4-H NA H3-C3-C10-H NA RRRS trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H NA RRRS cis H2-C2-C3-H NA H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. *RRSS trans H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H No observed coupling: H-3 (br s), H-10 couples to H 3-17 only. RRSS cis H2-C2-C3-H NA H3-C3-C4-H No observed coupling: H-3 (br s) H3-C3-C10-H NA RSSS trans H2-C2-C3-H NA H3-C3-C4-H NA 15
16 H3-C3-C10-H NA RSSS cis H2-C2-C3-H No observed coupling: H-2 couples to H 2-18 only H3-C3-C4-H NA H3-C3-C10-H NA 16
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