Table 1.
L. albiflora | L. aurea | L. caldwelii | L. chinensis | L. guangxiensis | L. haywardii | L. incarnata | L. longituba | L. radiata | L. radiata var. pumila | L. sanguinea | L. sprengeri | L. squamigera | L. traubii | |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Belladine-type | ||||||||||||||
2R-Hydroxy-N,O-dimethylnorbelladine (1) | [34] | |||||||||||||
Crinine-type | ||||||||||||||
Amabiline (2) | [28] | |||||||||||||
Ambelline (3) | [32] | [32] | ||||||||||||
Crinine (4) | [35] | |||||||||||||
Crinamabine (5) | [32] | [32] | ||||||||||||
Crinamidine (6) | [32] | [32] | [32] | |||||||||||
Galanthamine-type | ||||||||||||||
1,2,11,12-Tetradehydrogalanthamine * (7) | [32] | |||||||||||||
11β-Hydroxygalanthamine (8) | [30] | [28] | ||||||||||||
N-Norgalanthamine/N-Demethylgalanthamine (9) | [31,32] | [32,35] | [30] | [32] | [34] | |||||||||
N-Allylnorgalanthamine (10) | [35] | [28] | ||||||||||||
Galanthamine N-oxide (11) | [36] | [37,38] | ||||||||||||
N-(Chloromethyl)galanthamine (12) | [31] | [30] | ||||||||||||
Galanthamine (13) | [39,40,41] | [32,41,42] | [41,43] | [32,35] | [41] | [36,41,42] | [30,41] | [13,28,32,37,38,41,42] | [41] | [41,44] | [34,41] | [45] | ||
O-Demethyllycoramine-N-oxide (14) | [37] | |||||||||||||
O-Demethyllycoramine (15) | [36] | [30,41] | [37,38,46] | [34] | ||||||||||
N-(Chloromethyl)lycoramine (16) | [31] | [30] | ||||||||||||
Lycoramine-N-oxide (17) | [39] | [32] | [32,37,38] | |||||||||||
Lycoramine (18) | [39,41] | [32,41] | [41,43] | [32,35] | [41] | [36,41] | [41] | [32,37,38,41] | [41] | [41,44] | [34,41] | [45] | ||
Norlycoramine (19) | [41] | [41] | [41] | [41] | [41] | [41] | [41] | |||||||
Narwedine (20) | [41] | [32] | [32,35] | [41] | [41] | |||||||||
Sanguinine (21) | [41] | [41] | [36] | [30,41] | [37,46] | [34] | ||||||||
Galanthindole-type | ||||||||||||||
Lycosinine B (22) | [44] | |||||||||||||
Haemanthamine-type | ||||||||||||||
3α-Hydroxy-6β-acetylbulbispermine (23) | [47] | |||||||||||||
3α-Methoxy-6β-acetylbulbispermine (24) | [47] | |||||||||||||
3α,6β-Diacetylbulbispermine (25) | [47] | |||||||||||||
6β-Acetyl-8-hydroxy-9-methoxycrinamine (26) | [48] | |||||||||||||
6-Hydroxycrinamine (27) | [13] | |||||||||||||
6β-Acetoxycrinamine (28) | [13,48] | |||||||||||||
Haemanthamine (29) | [39] | [32,41] | [41] | [41] | [32,41] | [41,44] | [34] | |||||||
Haemanthidine (30) | [39] | [42] | [30] | [38] | [44] | [34,41] | ||||||||
8-O-Demethylmaritidine (31) | [32,46] | |||||||||||||
11-Hydroxyvittatine-N-oxide (32) | [32] | |||||||||||||
11-Hydroxyvittatine (33) | [46] | [34] | ||||||||||||
Vittatine (34) | [31,32] | [32] | [32,38] | |||||||||||
Homolycorine-type | ||||||||||||||
2α-Methoxy-6-O-ethyloduline (35) | [14,37] | |||||||||||||
2α-Methoxy-6-O-methyloduline (36) | [49] | [32] | [14] | |||||||||||
2α-Hydroxy-6-O-methyloduline (37) | [39] | [31,32,49] | [13,32,37] | |||||||||||
2α-Hydroxy-6-O-n-butyloduline (38) | [31] | |||||||||||||
2α-Hydroxyoduline (39) | [49] | |||||||||||||
Oduline (40) | [32,49] | [32] | [14,32] | |||||||||||
2α-Hydroxy-8-O-demethylhomolycorine-N-oxide (41) | [48] | |||||||||||||
8-O-Demethylhomolycorine-N-oxide (42) | [50] | [48] | ||||||||||||
8-O-Demethylhomolycorine (43) | [41] | [14,38,41] | [41] | |||||||||||
9-O-Demethylhomolycorine (44) | [39] | [14,37] | ||||||||||||
9-O-Demethyl-2α-hydroxyhomolycorine (45) | [37] | |||||||||||||
8,9-Methylenedioxyhomolycorine-N-oxide (46) | [32,47] | |||||||||||||
8-O-Acetylhomolycorine-N-oxide (47) | [13] | |||||||||||||
Homolycorine-N-oxide (48) | [39] | [38,47] | ||||||||||||
Homolycorine (49) | [39,40] | [31,49] | [41] | [13,14,38,41,42] | [41] | [44] | ||||||||
O-n-Butyllycorenine (50) | [31] | |||||||||||||
O-Ethyllycorenine (51) | [14,37] | |||||||||||||
O-Methyllycorenine (52) | [31] | [14,37,38,41] | [44] | |||||||||||
O-Methyllycorenine-N-oxide (53) | [38] | |||||||||||||
2α-Methoxy-6-O-methyllycorenine (54) | [44] | |||||||||||||
Lycorenine (55) | [40] | [14,42] | [44] | |||||||||||
Radiatine (56) | [37] | |||||||||||||
Hippeastrine (57) | [39] | [31,32,49] | [13,14,32,37,38,41] | |||||||||||
Hippeastrine-N-oxide (58) | [39] | [38] | ||||||||||||
Unsevine (59) | [32] | |||||||||||||
Hostasinine-type | ||||||||||||||
Hostasinine A (60) | [39] | |||||||||||||
Ismine-type | ||||||||||||||
Ismine (61) | [34] | |||||||||||||
Lycorine-type | ||||||||||||||
Assoanine (62) | [41] | [41] | ||||||||||||
Caranine (63) | [41] | [41] | [41] | [41] | [41] | [41] | [41] | [41] | ||||||
Galanthine (64) | [41] | [41] | [41] | [41] | [36,41] | [41] | [46] | [41,44] | [41] | |||||
Incartine (65) | [41] | [41] | [41] | [41] | [36,41] | [30] | [41] | [41] | ||||||
N-(Chloromethyl)ungiminorine (66) | [37] | |||||||||||||
N-(Chloromethyl)narcissidine (67) | [30] | [44] | ||||||||||||
Narcissidine (68) | [44] | |||||||||||||
(−)-epi-Zephyranthine (69) | [37] | |||||||||||||
Anhydrolycorine (70) | [41] | [41] | [41] | [41] | [41] | [41] | [41] | [41] | [41] | |||||
Dihydrolycorine (71) | [32] | [32] | [13,37] | |||||||||||
11-Methoxylycorine (72) | [37] | |||||||||||||
Pseudolycorine (73) | [35] | [37,51] | [34] | |||||||||||
5,6-Dehydrodihydrolycorine (74) | [41] | [13] | ||||||||||||
5,6-Dehydrolycorine (75) | [32,47] | |||||||||||||
11,12-Didehydroanhydrolycorine (76) | [41] | [41] | [41] | [41] | [41] | [41] | [41] | [41] | [41] | |||||
2-Hydroxyanhydrolycorine-N-oxide (77) | [52] | |||||||||||||
1-O-(3′-Hydroxybutanoyl)lycorine (78) | [45] | |||||||||||||
6-Oxodihydrolycorine (79) | [13] | |||||||||||||
Lycorine (80) | [39,40,41] | [31,32,41,42] | [41,43] | [32,35] | [41] | [36,41,42] | [30,41] | [13,28,32,38,41,42] | [41] | [41,44] | [34,41] | [45] | ||
1,2-Dihydroxy-anhydrolycorine-N-oxide (81) | [50] | |||||||||||||
2-Hydroxy-6-oxoanhydrolycorine (82) | [50] | |||||||||||||
1,2-Dihydroxy-6-oxoanhydrolycorine (83) | [50] | |||||||||||||
Norpluviine (84) | [41] | [41] | ||||||||||||
Pluviine (85) | [31,32] | [32] | [41] | [41] | [32,37] | [41] | [44] | [41] | ||||||
Hippadine (86) | [32] | [30] | [37] | [44] | ||||||||||
Lycosprenine (87) | [44] | |||||||||||||
Sternbergine (88) | [45] | |||||||||||||
Tortuosine (89) | [44] | |||||||||||||
1-Hydroxyungeremine (90) | [48] | |||||||||||||
Ungiminorine (91) | [36] | [45] | ||||||||||||
Ungiminorine-N-oxide (92) | [36] | |||||||||||||
Montanine-type | ||||||||||||||
Montanine (93) | [41] | [41] | [41] | [41] | [34,41] | |||||||||
Pancratinine C/Squamigine (94) | [41] | [37] | [34] | |||||||||||
(−)-3-O-Menthylpancracine (95) | [37] | |||||||||||||
Pancracine (96) | [37] | |||||||||||||
Montabuphine (97) | [44] | |||||||||||||
Lycolongirine C (98) | [30] | |||||||||||||
Narciclasine-type | ||||||||||||||
7-Deoxynarciclasine/Lycoricidine (99) | [39] | [13] | [53] | [34] | [45] | |||||||||
Narciclasine/Lycoricidinol (100) | [39] | [16,37] | [53] | [34] | [45] | |||||||||
5,6-Dihydrobicolorine (101) | [13] | [44] | ||||||||||||
Bicolorine (102) | [46] | |||||||||||||
N-Methylcrinasiadine (103) | [30] | |||||||||||||
N-Isopentylcrinasiadine (104) | [44] | |||||||||||||
Crinasiadine (105) | [44] | |||||||||||||
5,6-Dihydro-5-methyl-2-hydroxyphenanthridine (106) | [50] | [47] | ||||||||||||
Trisphaeridine (107) | [30,41] | [46] | [41,44] | |||||||||||
Tazettine-type | ||||||||||||||
3-O-Ethyltazettinol (108) | [54] | |||||||||||||
Deoxydihydrotazettine (109) | [28] | |||||||||||||
Deoxypretazettine (110) | [30,41] | [28,41] | ||||||||||||
Tazettine (111) | [41] | [41] | [41] | [41] | [30,41] | [38,41] | [41] | [41,44] | [34,41] | |||||
6-O-Methylpretazettine (112) | [34] | |||||||||||||
3-Epimacronine (113) | [28] | |||||||||||||
3-Hydroxylatifaliumin C * (114) | [32] | [32] | ||||||||||||
Dihydrolatifaliumin C * (115) | [32] | [32] | [32] | |||||||||||
Latifaliumin C * (116) | [32] | |||||||||||||
Other structural types | ||||||||||||||
Norharmane (117) | [30] | |||||||||||||
Harmane (118) | [30] | |||||||||||||
Lycolongirine A (119) | [30] | |||||||||||||
Perlolyrine (120) | [30] | |||||||||||||
Colchicine (121) | [28] | |||||||||||||
N-Methoxycarbonyl-2-demethylisocorydione (122) | [48] | |||||||||||||
2-Demethylisocorydione (123) | [50] | |||||||||||||
Isocorydione (124) | [50] | |||||||||||||
8-Demethyldehydrocrebanine (125) | [50] | |||||||||||||
N-Methoxycarbonyllindcarpine (126) | [52] | |||||||||||||
N-Methoxycarbonylnandigerine (127) | [52] | |||||||||||||
10-O-Methylhernovine-N-oxide (128) | [52] |
* Tentative identification based on mass spectra.