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:
[email protected]
© 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.
