Helvetica Chimica Acta Vol. 87 (2004)
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isomer of 6. Fr. 2, 4, and 5 were rechromatographed (CaCO3) to obtain the corresponding main components.
Repeated (2Â) CC of Fr. 2 (CaCO3; acetone/hexane 4 :96) resulted in Fr. 21 ((9Z)-1 and (9'Z)-1 [23]), Fr. 22 (2;
5.1mg after recrystallization from benzene/hexane 1:5), and Fr. 23 ((Z)-isomers of 2) [24]. Fr. 4 was
resubmitted (2Â) to CC (CaCO3; benzene/hexane 2 :3; 5 Â 30 cm), and the following two fractions were
obtained: Fr. 41, compound 1 (4.8 mg after recrystallization from benzene/hexane 1:5); and Fr. 42, compound 4
[19]. Repeated CC (2Â) of Fr. 5 (benzene/hexane 5 :95 to 10 :90) resulted in Fr. 51 (6) and Fr. 52 ((13Z)-6 and/
or (13'Z)-6) [13][21][25][26].
6. Analytical Data of 3'-Epilutein (2). 6.1. Sample Isolated from Sorrel. M.p. 152 1548. UV/VIS (benzene):
487, 457, 433. UV/VIS (EtOH): 475.5, 447.0, 423.5. CD (EtOH, r.t.): 209 ( 3.8), 217 (1.0), 242.5 (10.8), 266
(0), 281( À6.4), 301(0), 331( 4.1). 1H- and 13C-NMR: see the Table. EI-MS: 568 (100, M ), 550 (9), 476 (3),
235 (4), 223 (6), 209 (9), 197 (11), 173 (12), 157 (18), 145 (27), 134 (16), 119 (17), 105 (14), 95 (10), 81 (7), 69
(6), 55 (6), 43 (10).
6.2. Sample Isolated from Caltha palustris. M.p. 156 1588. UV/VIS (benzene): 487, 457, 433. UV/VIS
(EtOH): 475, 446, 423. CD (EtOH, r.t.): 208 ( 9.3), 217.5 (4.8), 241.5 (13.4), 268 (0), 281 (À 5.1), 296.5 (0),
330.5 ( 5). 1H- and 13C-NMR: see the Table. EI-MS: 568 (100, M ), 550 (16), 476 (4), 422 (1), 235 (3), 223 (4),
209 (7), 197 (6), 173 (6), 157 (9), 145 (11), 134 (6), 119 (11), 105 (6), 95 (6), 81 (4), 69 (4), 55 (3), 43 (2).
6.3. Sample Prepared by Reduction. M.p. 153 1558. UV/VIS (benzene): 487, 457, 433. UV/VIS (EtOH):
476, 446.7, 423.5. CD (EtOH, r.t.): 207 ( 5.0), 218.5 (1.5), 242.5 (11.4), 266.5 (0), 281.5 (À6.8), 300 (0), 331
(4.5). 1H- and 13C-NMR: see the Table. EI-MS: 568 (100, M ), 550 (7), 476 (7), 420 (1), 235 (4), 223 (11), 209
(15), 197 (13), 173 (14), 157 (21), 145 (32), 134 (22), 119 (35), 105 (26), 95 (23), 81 (14), 69 (12), 55 (15), 43
(16).
6.4. Sample Prepared by Epimerization. M.p. 148 1500. UV/VIS (benzene): 487, 457, 433. UV/VIS (EtOH):
475, 446, 423. CD (EtOH, r.t.): 242.5 ( 9.6), 268 (0), 280 (À4.8), 302.5 (0), 334.5 ( 3.4). 1H- and 13C-NMR:
see the Table. EI-MS: 568 (100, M ), 550 (11), 476 (5), 422 (2), 235 (5), 223 (8), 209 (11), 197 (10), 173 (10), 157
(15), 145 (22), 134 (14), 119 (23), 105 (16), 95 (14), 81 (9), 69 (8), 55 (9), 43 (8).
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