New Natural Dibenzocycloheptylamine Alkaloids: A Possible Catabolic Route for the Colchicine Alkaloids

Chemical constituents of the different parts ofColchicum baytopiorumand their cytotoxic activities on K562 and HL60 cell lines

“…Nine known alkaloids, namely, colchicine (1), 2-demethylcolchicine (2), 3-demethylcolchicine (3), 3-demethyl-N-formyl-N-deacetylcolchicine (4), colchifoline (5), 2-demethylcolchifoline (6), demecolcine (7), 2-demethyldemecolcine (8), and 2-demethyl--lumicolchicine (12), were isolated from the all separated parts of C. baytopiorum (Figure 1). The structures of the isolated compounds were elucidated using a series of spectrophotometric (UV, IR; 1 H-NMR, ESI-MS) methods by comparison of these spectral data with the literature (Fabian et al, 1955;Cross et al, 1965;Freyer et al, 1987;Husek et al, 1990;Abu-Zarga et al, 1991;Al-Tel et al, 1991) and TLC by comparison with authentic samples. The structures of three other alkaloids, namely, cornigerine (9), N-formyl-N-deacetylcolchicine (10), and 3-demethyldemecolcine (11) (Figure 1), were only determined by LC/MS/MS analysis (m/z values = 358, 386, 358, respectively).…”

Central-to-axial chirality transfer in the benzannulation reaction of optically pure Fischer carbene complexes in the synthesis of allocolchicinoids

“…Phenol 7a: pale yellow crystals; mp 148-148.5 °C; 1 H NMR (300 MHz, CDCl 3 ) δ 1.03 (t, 3H, J = 7. 4 Reaction with 3-Hexyne-This reaction was carried out in benzene with complex 6e (R 1 = Me, R 2 = Et) to give 7j in 58% yield. Only one diastereomer obtained which was identified as the (aR,7R; aS,7S) diastereomer 7 (R L = Et, R S = Et).…”

“…Phenol 7j: yellowish oil; 1 H NMR (500 MHz, CDCl 3 ) δ 0.99 (t, 3H, J = 7.1 Hz, CH 2 CH 3 ), 1.206 (t, 3H, J = 7.4 Hz, CH 2 CH 3 ), 1.214 (t, 3H, J = 7. 4…”

“…Phenol 11a (R 1 = Me, R 2 = Me, R L = Pr, R S = H): yellowish crystals, mp 104.5-105 °C. 1 H NMR (400 MHz, CDCl 3 ) δ 1.00 (t, 3H, J = 7 4. Hz, CH 2 CH 2 CH 3 ), 1.63-1.75 (m, 2H, CH 3 CH 2 CH 2 ), 2.19-2.29 (m, 1H, C5-Ha), 2.31-2.48 (m, 3H, C5-Hb, C6-H 2 ), 2.65-2.79 (m, 2H, CH 3 CH 2 CH 2 ), 2.90 (s, 3H, C7-OCH 3 ), 3.72 (s, 3H, OCH 3 ), 3.82 (s, 3H, OCH 3 ), 3.88 (s, 6H,2OCH 3 ), 5.07 (d, 1H, J = 5.5 Hz, C7-H), 6.63 (s, 1H, C4-H), 6.70 (s, 1H, OH, exchange with D 2 O), 6.78 (s, 1H, C9-H); 13 C NMR (100 MHz, CDCl 3 ) δ 14.0 (CH 3 ), 23.4 (CH 2 ), 31.1 (CH 2 ), 33.3 (CH 2 ), 39.9 (CH 2 ), 55.8 (CH 3 ), 56.2 (CH 3 ), 56.7 (CH 3 ), 61.1 (CH 3 ), 61.9 (CH 3 ), 73.8 (CH), 108.6 (CH), 112.9 (CH), 123.0 (C), 124.9 (C), 125.5 (C), 132.1 (C), 137.5 (C), 140.3 (C), 145.8 (C), 149.2 (C), 151.1 (C), 152.3 (C); IR (mix.…”

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

“…From Colchicum decaisnei (Liliaceae), some dibenzocycloheptadienes (dibenzocycloheptylamines) were isolated (1208), which are 'outsiders' in this chapter, but are treated here nonetheless because their structures show more similarities to the dibenzocyclooctadiene lignans than to any other group of substances within this review. The constitution of jerusalemine (526) was confirmed by a non-stereoselective synthesis, whereas that of salimine (527) had to be revised to correspond to the structure shown in Fig.…”