Spirosolane type

Solasodlns (spirosolane-type) Solanidine (solanidane-type)... 

Selenadiazole 256 Selenophene 107 Senoxepin 532 Serotonin 146 Sildenafil 480 Silthiofam 567 Simazine 412 Sirius Blue 150 Solanidane type 433 Sparteine 423 Spirosolane type 433 Squalene epoxide 25 Stibabenzene 437 Strychnine 532 Sulbactam 212 Sulfadiazine 472 Sulfamethoxazole 190 Sulfapyridine 379 Sulfolane 107 3-Sulfolene 105 Swainsonine 157 Sydnones 250 Systems... 

The structural features of the solanum alkaloids are based on two primary skeletal configurations solanidane, with or without glycoside functionalities, as featured by the toxic and teratogenic steroidal alkaloids a-chaconine and a-solanine with the indolizidine type E-F ring (Figure 2.7a) and the spirosolane... 

Potato GAs usually belong to one of two structural types, either solanidanes or spirosolanes (Figure 14.3). Solanine and chaconine, both solanidanes, often comprise upwards of 90% of the total GA complement of domesticated potatoes, with chaconine often more abundant than solanine (Griffiths et al., 1997 Sotelo and Serrano, 2000). 

Appendix) is graphically emphasized in Fig. (11) with values of the relative teratogenic potency of individual steroidal alkaloids from Table 2 placed adjacent to their structural type. The variance in values for the jervanes, solanidanes, and spirosolanes primarily reflects the level of saturation at C-5, C-6 e.g., 100 vs. 40 for jervanes, 32 vs. 9 for solanidanes, and 6 vs. 4 for spirosolanes. In each instance the higher value... 

Steroidal alkaloids of the Solanaceae can therefore be divided into two categories based on the aglycone the solanidine- and the solasodine-type alkaloids. The basic skeleton of the former alkaloids is known as solanidane, and that of the latter alkaloids is known as a spirosolane skeleton. 

Hydroxy-spirosolanes (Fig. 7.19). Solasodine is the dominating congener of the 25/ -series (22ot/V-configurated) and even the most frequent individual aglycone of all types of solanaceous glycoalkaloids. It was detected unequivocally in 207 out of 367 steroidal alkaloid-positive Solanum spp. (56%). 

The nomenclature used in this chapter follows the recommendations for the nomenclature ol Solanum alkamines published some time ago (7) and which has been accepted in general by most of the other authors. According to these proposals the heterocyclic basic ring system of the spiroaminoketal alkaloids (solasodine type, I) is named spirosolane (VI) in analogy with the similarly constructed but nitrogen-free... 

The most significant chemical progress in the last 10 years is the finding that in addition to the long known alkaloids with spirosolane and solanidane skeleton there are a number of new ones which represent novel types of structure (II, IV, V). Extensive investigations have progressed further to establish the complete stereochemistry of the alkaloids as well as to confirm these statements by a number of new partial and total syntheses. 

Epiminocholest-22 N)-ene Skeleton. Cyclic azomethines of the structural type CXXXI have been obtained, as mentioned above, by isolation from plant materials (see tomatillidine, verazine, the alkamines from S. congestiflorum), by acetylation of spirosolanes under strong acidic conditions 265, 271, 272), leading to 16)3-acetoxy substituted derivatives, by alkaline treatment of the V-chloro derivatives of 16-unsubstituted 282,286) and 16a-hydroxylated 254,255) 22,26-epimino-cholestanes, as well as by photolytic decomposition of the iV-nitroso-0,0-diacetate LXXXIX which gave the azomethine diacetate XCII 256, 257). 

---