Kreysigia

The Lily botanical family (Liliaceae Adans., Juss.) (Table 14) is spread worldwide and contains more than 200 genera and around 3500 species. Some genera of this family produce L-tyrosine-derived alkaloids. The genus Kreysigia yields autumnaline, floramultine and kreysigine. 

Some typical genera Colchicum Erythronium Fritillaria Gagea Kreysigia Lilium Medeola... 

Specifically C-labeled 1 -phenethylisoquinolines were administered to Kreysigia multiflora plants, and the alkaloids were isolated and degraded to unambiguous sequences. The results show that the C-homoaporphine... 

Reviews of this group are available in one of these, coverage is limited to alkaloids elaborated by the Wurmbaeoideae plants. Several new reports concerning exhaustive isolation studies of Colchicum species as well as of Kreysigia multijlora, Merendera fitifolia, and M. jolantae plants have appeared. For the most part, known colchicine alkaloids have been found although structures of several new ones have not been defined. A study of composition of alkaloids in Colchicum luteum at various stages of development has been described. 

Of the homoproaporphine alkaloids kreysiginone (19), dihydro-kreysiginone (21), and bulbocodine (22), the former two (19 and 21) were isolated from Kreysigia multiflora (2a). The last was isolated from Bulhocodium vernum (16) and its structure has been determined recently by Santavy (17). 

Some years ago, three alkaloids, namely, kreysigine (31a), floramul-tine (32), and multifloramine (33), were isolated from Kreysigia multiflora 6, 20). Recently, a fourth alkaloid, (— )-kreysigine (31b) was isolated from Bvlbocodium vernum (17). The chemical behavior of this alkaloid has not been described. 

In order to distinguish between these possibilities, the [3- C] diphenolic isoquinolines 77a,b,c were administered to Kreysigia multiflora shoots which converted the homoaporphines 79a,b,c,d into... 

Before kreysiginone was isolated from a natural source diphenolic isoquinoline 76 had been oxidized with ferric chloride to yield homo-proaporphines 19 and 20 (40), one of which, dienone 19, was isolated from Kreysigia multiflora by Battersby (2a). Battersby also synthesized both dienones 19 and 20 by the same reaction of 76 with potassium ferricyanide. In this reaction he examined the phenol oxidation of the diphenolic isoquinoline 86 and obtained product 87 containing... 

Homoaporphine Alkaloids.—Full details of the research on the biosynthesis of the homoaporphine alkaloids of Kreysigia multiflora have been published. In essence there is no information additional to that published in preliminary form and reviewed. ... 

Their occurrence is limited to the Liliaceae, e. g., Col-chicum, Kreysigia, anAAndrocymbium species (see table). They are readily soluble in water, chloroform, and ethanol. Colchicine is one of the few natural tropolone derivatives, see, e. g., fomentariol. It occurs together with other, structurally related alkaloids (colchamine, colchicoside, colchiceine, colchiciline, colchifoline) in meadow saffron (autumnal crocus, naked lady, Col-chicum aummnale). Colchicine is a highly potent mi-... 

Oberlin-Zeisel reaction (Rgt. No. 102) yields brown-blue. Isolated from Kreysigia multiflora,... 

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