Steroid alkaloid, Solarium

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. 

Solarium biflorum Loureiro Hong Si Xian (whole plant) Glycoside alkaloids, steroid alkaloid glycosides.55360-361 Detoxicant, for cough, swelling, dog bites. 

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... 

Steroidal Alkaloids.—In the biosynthesis of alkaloids such as solasodine (128), from cholesterol (129), it appears that the cholesterol side-chain is first functionalized at C-26 with the introduction of a hydroxy-group (cf. Vol. 8, p. 28 Vol. 7, p. 32). The 26-amino-compound, (25i )-26-aminocholesterol (130), has been found to act as a significant precursor for solasodine (128) in Solarium laciniatum, whereas (25i )-26-aminocholest-5-ene-3/ ,16/ -diol (131) was poorly utilized.105 This indicates that replacement of the hydroxy-group at C-26 by an amino-group may occur before further oxygenation elsewhere in the steroid nucleus (particularly at C-16). It may also be concluded from this and other evidence (cf. Vol. 9, p. 27) that oxidation at C-22 precedes hydroxylation at C-16. 

The alkaloid literature has been reviewed up to the end of June 1970, but for convenience most authors have started their literature surveys from January 1969 this inaugural volume, therefore, properly represents a summary of developments in the subject during an eighteen-month period. The whole field of alkaloid chemistry has been reviewed with the exception of the steroidal alkaloids of the Solarium and Veratrum groups. It has not proved possible owing to limitations of space to include these sub-groups in the present volume, and it is therefore planned to include a review of developments in this area during a two-year period in the second volume. 

Steroidal Alkaloids.—[26,27- C2]Cycloartanol (182) and [26,27- CJlanosterol (183) have been examined as precursors for solanidine (184) in Solarium chacoense, tomatidine (185) in Lycopersicon pimpinellifolium, and solanocapsine (186) in... 

Solarium and Veratrum Steroidal Alkaloids 2 Veratrum Alkaloids... 

Fig. 2 TLC-immunostainings of steroidal alkaloid glycosides in the crude extracts of Solarium species fruits. Cmde extracts were developed by a CHCI3 MeOH NH4OH solvent system on sihca gel TLC plate. After being transferred to a PVDF membrane, the membrane was treated with NaI04 and stained by MAb. Spots 1-3 were identified with khasianine, solamargine, and solasonine, respectively.

Table 7.3 Steroidal alkaloids (alkamines) alphabetically listed within the different structural types For 41 out of altogether 115 compounds from Solarium spp. (113 compounds), Lycianthes biflora, and Saracha punctata (one compound each) at least one corresponding glycoalktiloid was found and structurally elucidated, i.e., for 36% of the alkamines also corresponding glycosides are known (continued)...

Table 7.4 Update and additions to the catalogue of species in the reviews of Schreiber (1968), Ripperger and Schreiber (1981), and Ripperger (1998) on the occurrence of steroidal alkaloids within the genus Solarium (continued)... 

Thus, it may be assumed, that steroidal alkaloids, i.e., alkamines and/or glycoalkaloids, represent a common and consistent ttait in the genus Solarium. This was already assumed by Heftmann (1983) ( It is quite possible that they occur in all representatives of this genus ) and Hegnauer (1990) Solatium alkaloids are hardly absent in any species of the genus . 

UsubillagaA(1988) Solanudine, a steroidal alkaloid from Solarium nudum. Phytochemistry 27 3031-3032... 

Woody nightshade. Solarium dulcamara, has been used from the time of Galen (c. AD 180) for the treatment of cancers. Recent studies on the plant have shown that the steroidal alkaloid glycoside -solamarine is active against S 180 [344] however, its low therapeutic index precludes it from further pharmacological study. A number of steroidal alkaloid glycosides have been reported to have cytostatic activity [345], and solananine to be a mitotic poison [346]. 

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