Solanidine alkaloids

A O-Diacetyldihydropseudosolasodine (12a) gave the epimeric pyrrolidines (13) on treatment with bromine. When N-bromosuccinimide was used as oxidant, the ketone (12b) and the pyrrolidine (14) were also formed.17 The WolfF-Kishner reductions of solasodenone (9b) and of the epimeric 4,5 -dihydro-analogues have been reported.18 Solasodine gave the expected 5a,6-epoxide on treatment with perbenzoic acid.19 The preparation of an intermediate in the synthesis of the solanidine alkaloids has been reviewed.20... 

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

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. 

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... 

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. 

Solanum indicum L. Niu Zi Qie (Indian nightshade) (root, leaf, fruit) Diosgenin, solanidine, solanine, solasodine, alkaloids, carbohydrases, maltase, saccharase, melibiase.50 Antidote for poison, for urinary disease. 

A number of alkaloids (nitrogenous bases) are derived from steroids. An example is solanidine (Fig. 22-12), which is present in the skins and sprouts of potatoes, making both quite toxic. 

Solanidine and hapepunine have been isolated from Fritillaria verticillata, together with two new alkaloids, baimonidine (33a) and isoverticine (33b). The structures indicated were assigned mainly on the basis of the H and 13C n.m.r. spectra of the new alkaloids and were confirmed by the preparation of these alkaloids from verticinone (33c) by standard methods.70 The 13C n.m.r. spectra of a number of other cevanine derivatives have been reported.70 Fritillarine and a new alkaloid, C27H4303N, have been isolated from F. karelinii.71... 

Verazine (138) appears to be an important early intermediate in the biosynthesis of Veratrum grandiflorum alkaloids, e.g. solanidine (139).120 Apparent correlation between changes in arginine content and accumulation of verazine (138) in dormant V. grandiflorum rhizomes, as well as the observation that l-[15N]arginine is a much more effective source for solanidine biosynthesis than [15N]ammonium chloride, indicates that arginine is a primary source of alkaloidal nitrogen.121... 

Further exploration125 of the stereochemistry associated with modification of the steroidal side-chain into that of steroidal alkaloids such as solanidine (139) and tomatidine (140) has revealed that on formation of the furan ring in (140) tritium in the 16/8-configuration of cholesterol [as (143)] is retained but appears now in the 16a-configuration. Retention of the tritium excludes a C-16-oxo-intermediate, and the fact that an inversion of configuration is observed excludes hydroxylation with normal retention of configuration. Examination of the fate of the cholesterol 16/S-proton on incorporation into solanidine (139) revealed that during solanidine biosynthesis this proton is lost. 

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