22/?,255-Solanidines

Structures of the steroidal alkaloids whose relative teratogenic potencies are listed in Table 2 and whose embryolethality and teratogenicity is recorded in Table 3 are provided as follows jervine (1), cyclopamine (2), tomatidine (4), and solasodine (6) are listed in the text. Structures for 22/ , 255-solanidine, a-solanine, and ct-chaconine are provided in Fig. (10). In solanidine-N-oxide, the electron pair on the nitrogen atom of solanidine in Fig. (10) is replaced by an oxygen atom. Dihydrosolanidine refers to solanidine with a reduced C-5, C-6 linkage. Dihydrojervine refers to the jervine structure (1) with the C-12, C-13 bond saturated and tetrahydrojervine has both C-5, C-6 and C-12, C-13 linkages saturated. Dihydrosolasodine is shown as structure 6 having C-5, C-6 saturated. 

In addition to the alkaloids such as cyclobuxiae-D (129) and solanidine (130) where the stmctural similarities to steroids are clear (although it must be remembered that detailed evidence actually linkiag the compounds is lacking) there are the less obvious (but nonetheless also clearly related) Veratrum alkaloids. These compounds, of which protoverattine A [143-57-7] (131), obtained from the rhizome of Veratrum album L. (LiUaceae), is a... 

Firbas stated that at least two of these alkaloidal glucosides occur in young potato shoots, solanine and solaneine, and that these may be accompanied by solanidine, a basic decomposition product of solanine. Solaneine was later shown to be a mixture of solanine and solanidine. 

Solaneine, isolated by Firbas and examined by Davis, has been shown by Soltys to be a mixture of solanine and solanidine. 

Solanidine contains at least three CMe groups, and since it yields dihydrosolanidine, m.p. 219-220°, must contain one ethylenic linkage. When solanidine is heated with copper powder at 160-300°/ll mm., it is converted into solanidone, C27H41ON, m.p. 218°, which yields an oxime, m.p. 228°, and condenses with benzaldehyde or amyl nitrite to give compounds indicating the existence in solanidone of the group —CHj—CO—CH — and therefore in solanidine of —CHjj—CHOH—CHa—... 

Solasodine (solanidine-s), C27H43O2N. H2O. This formula was first used by Rochelmeyer (1939) and was confirmed by Briggs, Newbold and Stace. The alkaloid results from the acid hydrolysis, usually in... 

Colour Reactions. Rochelmeyer (1939) has provided a list of colour reactions given by solasodine and solasodiene (solanosodine), with reagents usually applied to the sterols, and Briggs et al. have found that when concentrated sulphuric acid (1 mil) is carefully added to a solution of solasonine or solasodine in hot alcohol (1 mil) a characteristic, intense, greenish-yellow fluorescence is produced, a reaction which is not given by solanine or solanidine. They have also found that intense colours are formed when solasonine or solasodine is mixed with resorcinol, or one of a variety of aldehydes, and boiled with concentrated hydrochloric acid. Colours are also produced with this test by cholesterol, digitonin, jacobine carbazole, pyrrole, or nicotine, the most intense colours being formed with p-hydroxybenzaldehyde or anisaldehyde. 

Solangustidine solangustine, 671 Solanidine, 661, 662, 671, 708, 712, 713 dehydrogenation products, 663 heterocyclic residue, 665 proximate derivatives, 664 structure, 665, 667 Solanine, 661... 

MOEHS, C.P., ALLEN, P.V., FRIEDMAN, M, BELKNAP, W.R., Cloning and expression of solanidine UDP-glucose glycosyltransferase from potato, Plant J., 11 227-236. 

The fruit of a number of solanaceous plants, including tomato Lycopersicon esculentum), potato Solanum tuberosum) and eggplant Solarium melongena esculentum), have cholinesterase-inhibiting effects (Krasowski et al. 1997). They contain solanaceous glycoalkaloids o-solanine and o-chaconine, which are triglycosides of solanidine, a steroidal alkaloid derived from cholesterol. They are the only plant chemicals known to inhibit both acetlycholinesterase and butyrylcholinesterase, both in vitro and in vivo. 

Some quinoline alkaloids from the aerial parts of Skimmia laureola (DC.) Dene have shown antiChE activity in vitro and methyl isoplatydesmine (49) was shown to be the most active inhibitor of both AChE and BuChE. Solanidine (50), related compounds and glycosides are... 

Saponins Steroid alkaloids Cholestane Conessine Cyclopamine Jervine Pregnenolone Protoveratrine A Protoveratrine B Solanidine Solasodine Squal amine Tomatidine... 

These alkaloids can also be derived from non-aminoacid precursors. The N atom is inserted into the molecule at a relatively late stage, for example, in the case of steroidal or terpenoid skeletons. Certainly, the N atom can also be donated by an amino acid source across a transamination reaction, if there is a suitable aldehyde or ketone. Pseudoalkaloids can be acetate and phenylalanine-derived or terpenoid, as well as steroidal alkaloids. Examples of pseudoalkaloids include such compounds as coniine, capsaicin, ephedrine, solanidine, caffeine, theobromine and pinidine (Figure 6). More examples appear in Table 1. 

Steroid alkaloids Solanaceae Liliaceae Solanum tuberosum Lycopersicon esculentum Veratrum album Solanidine Tomatine Jervine Cyclop amine Cycloposine Protoveratrine A Protoveratrine B... 

Alkaloids are active bioagents in animal tissues. There is clear scientific evidence of this. Crawford and Kocan" " have tested the toxicity of steroidal alkaloids from the potato Solanum tuberosum), such as a-chaconine, a-solanine, solanidine and solasodine, and Veratrum alkaloid, jervine on fish. The results of Crawford and Kocan s research proved that rainbow trout exhibited a toxic response to chaconine, solasidine and solanine, while medaka only did so to chaconine and solanine. Embryo mortality was observed as an effect of toxicity in both species. Many other alkaloids are known to disturb or cause disorder in animal reproductive systems. For example, gossypol from cotton-seed oil is known as a clear reducer of spermatogenesis and premature abortion of the embryo. 

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