Crinum latifolium

Latisoline (577) is a novel glucosyl alkaloid that was isolated from Crinum latifolium (36), and the structural assignment was based on its hydrolysis with emulsin to provide the aglycone latisodine (578) and D-glucose. Further support... 

Latifine (594) is a new phenolic base isomeric with cheiylline (595) that has been isolated from Crinum latifolium L. (227). The (S) configuration at C-4 of 594 was deduced from an observed negative Cotton effect in the ORD curve of 594 and 595, and this assignment was confirmed by an X-ray analysis of the N-bromobenzamide derivative of 594. 

A new 4-arylisoquinoline alkaloid, latifine, isolated from Crinum latifolium, has been identified as an isomer (21, R = OH, R =H) of cherylline (21, R =H, R =0H) (S. Kobayashi, T. Tokomuto and Z. Taira, Chem.Comm., 1984, 1043). A novel synthesis of cherylline has been achieved from the iminium salt (19) by treatment with diazomethane, cyclisation of the resulting aziridinium salt (20) and hydrogenolytic removal of the benzyl groups (T. Kametani, et al., J.chem.Soc., Perkin I, 1982, 2935. 

The flower stem fluid of Crinum latifolium 31) has been examined, from which numerous Amaryllidaceae alkaloids have been isolated. Among them, two lycorine-type alkaloids, 2-epi-lycorine (4) and 2-epi-pancrassidine (7), are included, structures of which were determined by spectroscopy. 

Since the previously published review (8), novel 4-aryltetrahydroiso-quinoline type alkaloids have not been found in the Amaryllidaceae plants. Only latifine (437) has been isolated from the bulbs of Crinum latifolium (200). The structure was confirmed by spectroscopic evidence. X-ray crystallographic analysis, and synthesis (198). 

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