Antibacterial C-Geranylflavonoids from Paulownia tomentosa Fruits

Antibacterial C-Geranylflavonoids from
Paulownia tomentosa Fruits
Karel Šmejkal,*,† Stanislav Chudík,† Pavel Klou#ek,‡ Radek Marek,§,* Josef Cva#ka,) Marie
Urbanová,|| Ond.ej Julínek,|| Ladislav Kokoška, Tereza Šlapetová,† Pavla Holubová,† Aleš
Zima,† and Margita Dvorská†
Department of Natural Drugs, University of Veterinary and Pharmaceutical Sciences
Brno, Palackého 1-3, CZ-612 42 Brno, Czech Republic, Department of Crop Production,
Faculty of Agrobiology, Food and Natural Resources, Czech University of Life Sciences
Prague, Kamýcká 129, CZ-165 21 Prague 6-Suchdol, Czech Republic, National Center for
Biomolecular Research, Faculty of Science, Masaryk University, Kamenice 5/A4, CZ-625
00 Brno, Czech Republic, Mass Spectrometry Group, Institute of Organic Chemistry and
Biochemistry, v.v.i., Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ166 10 Prague 6, Czech Republic, Department of Physics and Measurements and
Department of Analytical Chemistry, Institute of Chemical Technology, Technická 5, CZ166 28 Prague 6, Czech Republic, and Department of Crop Sciences and Agroforestry in
Tropics and Subtropics, Institute of Tropics and Subtropics, Czech University of Life
Sciences Prague, Kamýcká 129, CZ-165 21 Prague 6-Suchdol, Czech Republic
Table S1. 13C NMR and 1H-13C HMBC of 1-4. 1H-13C HMBC (adjusted to 7.5 Hz) correlations are from the
carbon(s) to the protons indicated.
position
C-2
C-3
C-4
C-4a
C-5
C-6
C-7
C-8
C-8a
C-1´
C-2´
C-3´
C-4´
C-5´
C-6´
C-1´´
C-2´´
C-3´´
C-4´´
C-5´´
C-6´´
C-7´´
C-8´´
C-9´´
C-10´´
3´-OMe
5´-OMe
1 (DMSO-d6)
BC
HMBC
78.4 2´, 6´
42.1
196.4 3, 8
101.4 8
160.5 1´´
107.5 8, 1´´, 2´´
164.4 8, 1´´
94.4
160.5
129.5 2, 3, 2´, 5´
111.0 2´, 6´
147.5 5´
146.9 2´, 6´
115.1
119.6 2, 2´
20.5 2´´
122.1 1´´, 4´´, 5´´
134.0 1´´, 4´´, 5´´
16.0 2´´
35.1 2´´, 4´´, 6´´
33.3 5´´, 6´´, 9´´
73.4
148.1 6´´, 9´´, 10´´
109.7 10´´
17.6
56.1
-
2 (DMSO-d6)
BC
HMBC
78.6 3, 2´, 6´
42.2
196.3 3, 8
101.4 8
160.5 1´´
107.7 8
164.4 8, 1´´
94.3
160.4 8
128.7 2´, 3´, 6´
102.2 6´
148.2 2´
134.3 2´, 6´
146.6 6´
107.5 2´
20.5
122.4 1´´, 4´´, 5´´
133.7 1´´, 4´´, 5´´
15.8 5´´
39.7 4´´
26.2
124.1 5´´, 6´´, 9´´,10´´
130.6 6´´, 9´´, 10´´
25.5
17.5
55.8
-
3 (CDCl3)
BC
HMBC
79.3 2´, 6´
43.5 2
195.9
102.8 8
161.2 1´´
107.2 1´´
164.0 8, 1´´
95.6
160.9 8
129.6 2, 6´
103.2
147.2 2´, 6´
135.2 2´, 6´
147.2 2, 6´
103.2
21.0
121.3 1´´
138.9 1´´, 4´´
16.1
39.7 4´´
26.4
123.8 9´´
131.9 9´´
25.6
17.7
56.3
56.3
4(DMSO-d6)
BC
HMBC
78.6 3, 2´, 6´
42.2
196.2 3, 8
101.3 8
160.5 1´´
107.4 8, 1´´
164.9 8, 1´´
94.5
160.5 8
129.5 3, 2´, 5´
111.0 6´
147.5 5´
146.9 2´, 6´
115.1 2´
119.6 2´
20.6
123.1 1´´, 4´´
133.1 1´´, 4´´, 5´´
15.9 2´´, 5´´
41.9 2´´, 4´´,7´´
123.1 5´´, 7´´
140.6 5´´, 9´´, 10´´
68.8 6´´, 9´´, 10´´
30.1 7´´
30.1 7´´
55.6
-