1 Supporting Information to: 5 -Cardenolides from Kanahia laniflora Inhibit Inotropic Acetylcholine Receptors Cailean Clarkson1 Ian R. Mellor2 Maja Lambert1 Jerzy W. Jaroszewski1 Affiliation: 1 Department of Medicinal Chemistry, The Danish University of Pharmaceutical Sciences, Copenhagen, Denmark 2 School of Biology, University of Nottingham, Nottingham, United Kingdom Correspondence: Prof. Jerzy W. Jaroszewski Department of Medicinal Chemistry The Danish University of Pharmaceutical Sciences Universitetsparken 2 2100 Copenhagen Denmark Fax: +45-3530-6040 E-mail: jj@dfuni.dk © Georg Thieme Verlag KG · DOI 10.1055/s-2006-951704 (10.1055/s-2006-951736) · Planta Med 2006; 72: e372–e374 · Clarkson C et al. 2 Table S1 1H-NMR data for 5 -cardenolides 1
4 isolated from Kanahia lanifloraa 2b 3 4 1 1.07 m 1.14 t (12.3) 1.12 t (12.1) 1 1.87 m 2.50 dd (12.5, 4.5) 1.88 m Position 1 2 4.07 ddd (11.8, 10.0, 4.4) 4.09 ddd (12.0, 10.1, 4.3) 3.90 ddd (12.0, 9.9, 4.5) 4.09 ddd (12.0, 10.0, 4.4) 3 3.94 t (10.6, 4.7) 3.88 ddd (10.4, 10.1, 5.3) 3.98 ddd (11.2, 9.9, 4.5) 3.96 ddd (11.6, 10.0, 4.8) 4 1.40 m; 1.48 m 1.45 m; 1.76 m 1.47 m; 1.59 m 5 1.24 m 1.52 m 1.26 m 6 1.12 m; 2.04 m 1.14 m; 1.98 m 1.09 m; 1.95 m 7 1.28 m; 1.43 m 1.25 m; 1.46 m 1.26 m; 1.44 m 8 1.60 m 1.54 m 1.51 m 9 1.09 m 1.31 m 1.04 m 11 1.32 m; 1.52 m 1.26 m; 1.73 m 1.26 m; 1.56 m 12 1.58 m; 1.72 m 1.32 m; 1.52 m 1.36 m; 1.51 m 15 4.54 m 1.70 m; 2.12 m 1.68 m; 2.00 m 1.67 m; 2.06 m 16 2.64 m 1.88 m; 2.17 m 1.87 m; 2.16 m 1.86 m; 2.15 m 17 2.64 m 2.83 m 2.76 dd (9.6, 5.6) 2.78 dd (9.5, 5.8) 18 0.92 s 1.24 s 0.82 s 0.88 s 19 0.86 s 1.23 s 10.01 s 0.87 s 21 4.80 dd (18.2, 1.7) 4.91 dd (18.4, 1.6) 4.79 dd (18.1, 1.9) 4.80 dd (18.1. 1.7) 5.04 dd (18.2, 1.7) 5.03 dd (18.4, 1.5) 4.94 dd (18.1, 1.7) 4.97 dd (18.1, 1.7) 22 5.85 br t (1.5) 5.89 br t (1.5) 5.83 br t (1.7) 5.87 br t (1.5) 1 4.58 s 4.45 s 4.58 s 4.60 s 3 4.76 dd (12.0, 5.1) 3.58 dd ( 12.1, 4.9) 4.76 dd (12.1, 5.1) 4.77 dd (12.2, 5.2) 1.55 m; 1.61 m 1.71 m; 1.86 m 1.74 m; 1.86 m 4 5 3.69 dqd (11.7, 6.1, 1.6) 3.65 m 3.70 dqd (11.3, 6.1, 1.8) 3.70 dqd (11.2, 6.2, 1.8) 6 1.30 d (6.1) 1.23 d (6.2) 1.30 d (6.1) 1.30 d (6.2) CH3CO 2.15 s - 2.17 s 2.16 s a 400 MHz spectra in chloroform-d unless otherwise stated; multiplicity of signals is given as follows: s, singlet; d, doublet; dd, double doublet; ddd, double double doublet; br t, broad triplet; dqd, double quartet doublet; m, multiplet; coupling constants (apparent splittings) are given in parentheses as numerical values in Hz;  values for 2
4 assigned using COSY, HSQC and HMBC spectra, partial assignment for 1 performed by comparison with literature data [5], [6]. b In methanol-d4.. © Georg Thieme Verlag KG · DOI 10.1055/s-2006-951704 (10.1055/s-2006-951736) · Planta Med 2006; 72: e372–e374 · Clarkson C et al. 3 Table S2 13C-NMR data for 5 -cardenolides 1
4 isolated from Kanahia lanifloraa Position 1 2b 3 4 1 42.5 43.4 35.9 42.8 2 69.3 70.2 69.1 69.1 3 72.9 74.2 71.6 72.3 4 32.4 33.6 33.1 32.1 5 45.2 46.5 43.3 44.9 6 28.1 28.7 27.3 27.3 7 27.0 29.2 26.7 27.6 8 40.9 41.9 42.4 41.2 9 49.7 51.3 48.5 49.6 10 38.5 39.1 52.7 38.1 11 21.4 22.6 21.8 21.3 12 38.9 39.7 39.4 40.0 13 49.1 51.0 49.4 49.6 14 82.1 86.2 85.2 85.3 15 73.7 33.5 32.3 33.1 16 37.5 28.0 26.8 26.8 17 49.2 52.1 50.5 50.9 18 16.9 16.6 15.6 15.9 19 14.2 14.4 206.8 13.9 20 174.8 178.4 174.3 174.5 21 73.8 75.4 73.3 73.0 22 118.5 118.1 117.6 117.6 23 174.0 177.3 174.0 174.3 1 96.6 97.7 95.9 95.9 2 91.3 92.8 90.8 90.8 3 76.1 74.0 75.7 75.9 4 35.8 41.0 35.4 35.6 5 68.1 69.5 67.7 67.5 6 21.2 21.4 20.9 20.9 CH3CO 21.5 - 21.2 21.1 CH3CO 172.8 - 172.4 172.5 a 100 MHz spectra in chloroform-d unless otherwise stated;  values for 2
4 assigned using HSQC, HMBC, and DEPT spectra, those for 1 assigned by comparison with literature data [5], [6]. b In methanol-d4. © Georg Thieme Verlag KG · DOI 10.1055/s-2006-951704 (10.1055/s-2006-951736) · Planta Med 2006; 72: e372–e374 · Clarkson C et al.