Solarium alkaloids

C Spectra are also reported for some glucoside and mannoside derivatives of alcohols of a sterol type, " and for a series of steroidal Solarium alkaloids with various E/F-ring structures. ... 

Solasodine (0.01%), tomatidenol (0.001%), and a new Solarium alkaloid, solanaviol (0.05%), have been isolated from dried leaves of S. aviculare.21 Solanaviol was assigned the structure 12/3-hydroxysolasodine (15a) on the basis of mass-spectral and H and 13C n.m.r. studies and the conversion of solanaviol... 

The utility of high-performance liquid chromatography (h.p.l.c.) has been demonstrated in the separation of Solarium and Veratrum steroidal alkaloids.50 Methods have been described for the determination of Solarium alkaloids by paper chromatography51 and of crude glycoalkaloids by t.l.c.52... 

Hapepunine (72), occurring in Fvitillavia aamtsahataensis, is the first natural 166-hydroxy-22,26-epiminocholestane derivative encountered (Mitsuhashi et al., Tetrahedron Letters, 1978, 2099). Anrakorinine, from the same source, affords a tosylate which on reduction (LiAlH ) yields hapepunine (72). In its pmr-spectrum it lacks a methyl singlet at 6 0.96 ppm (present in hapepunine), but has an AB quartet (2H) at 3.62 and 3.88 ppm. Consequently it is formulated as 18-hydroxyhapepunine (73) idem, Phytochem., 1981, M, 157). Several indolizidine bases, also related to Solarium Alkaloids, have been encountered in the Fritil-laria group. Camtschatcanidine, for example, from F. aamtsohatoensis, is (74), on the basis of spectral comparison with solanidine on reduction (LiAlHi ) of its 0-tosyl-derivative solanidine (75) is formed (Mitsuhashi et al.. 

The glyco-alkaloid a-tomatine has been the subject of a detailed review, which covers chemical, biochemical, and biological aspects. The synthesis and biogenesis of steroidal Solarium alkaloids has also been reviewed. ... 

Each of the teratogenic expressions induced by Veratmm in sheep, which include not only craniofacial, but also limb, palate, and tracheal malformations that are induced at later gestational periods [45], has related counterparts in humans [46]. Although Veratmm species are not eaten by humans, many Solarium alkaloid-containing species are used as human foods [47]. For these reasons, numerous investigations of steroidal... 

Like rubijervine it has two hydroxyls, but in this case one is secondary and the other primary. It also has a basic tertiary nitrogen and one double bond. Aside from the different location of one of the hydroxyls, the two alkaloids display considerable similarity in their reactions. Although the direct relation of isorubijervine to a Solarium alkaloid has not been achieved, there is little doubt that it represents another isomer of hydroxysolanidine. In the following discussion the formula (XV) of Sato and Jacobs (58) will be used. In this formula the primary hydroxyl, which has as yet not been definitely located, is placed on C-18 of the solanidane skeleton. (See addendum on p. 312.)... 

Solanidine alkaloids. The second group of Solarium alkaloids, the solanidine alkaloids, also occur as glycoalka-loids. An example of this type is solanidine (49). 

For the quantitative determination of Solarium alkaloids in plant materials some new methods have been developed for instance, gravimetric procedures using the afore-mentioned cholesterol precipitation (15) for tetraosides, especially with saturated aglycones volumetric methods with titration of the bases in water-free solvents using aromatic sulfonic acids (26c, 47, 48) a number of simplified spectrophotometric methods by applying the Clarke reaction (49), that is, the hlue color obtained with paraformaldehyde-phosphoric acid in the case of J -unsaturated steroid alkamines and their glycosides (12, 50-52a, 525), or with the aid of amphi-indicators of the tropaeolin type (52,53-57,57a). The well-known Liebermann-Burchard reaction is not applicable to nitrogenous 3 -hydroxy-J -steroids (55). ... 

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