Steroidal alkaloids biology

Keeler, R.F. (1986). Teratology of steroidal alkaloids, in Pelletier, S.W., Ed., Alkaloids chemical and biological perspectives, John Wiley and Sons, New York, pp. 389-425. 

Amiya T and Bando H (1988) Aconitum alkaloids. The Alkaloids, Chemistry and Pharmacology (ed Brossi A) Vol 34. Academic, San Diego, pp 95-179. Atta-ur-Rahman and Choudhary MI (1998) Chemistry and biology of steroidal alkaloids. The Alkaloids, Chemistry and Pharmacology (ed Cordell GA) Vol 50. Academic, San Diego, pp 61-108. Atta-ur-Rahman and Choudhary MI (1999) Diterpenoid and steroidal alkaloids. Nat Prod Rep 16, 619-635. Earlier reviews 1997, 14, 191-203 1995, 12, 361-379. 

Ripperger H (1998) Solanum steroid alkaloids an update. Alkaloids, Chemical and Biological Perspectives (ed Pelletier SW) Vol 12. Elsevier, Amsterdam, pp 103-185. 

In general, plants do very well in their environments, notwithstanding the omnipresence of a multitude of potential insect herbivores and a number of vertebrate herbivores as well. Some plant species are very insecticidal, as a consequence of their producing a variety of alkaloids including nicotine, piperine, lupine alkaloids, steroidal alkaloids, ephedrine, berberine, strychnine, gramine, and caffeine.37 These biologically active alkaloids also function as deterrents. In terms of families, caffeine is the the most widely distributed alkaloid, a fact that may be... 

The other steroids, such as bile acids (cholane), vitamin D, saponin steroids, steroid alkaloids, cardiac glycosides, and brassinosteroids, also have biologically important activities. Due to the metabolic versatility of steroid molecules, extremely complex mixtures are often encountered, necessitating the use of chromatographic methods (HPLC, TLC, GC) for their analyses. 

The gross biological activity of various classes of steroids has been briefly reviewed and their action at cellular and molecular levels discussed. The texts of the Plenary Lectures presented at the Sixth International Symposium on The Chemistry of Natural Products have been published these include papers on steroidal alkaloids and sapogenins, " synthetic cardenolides, mass spectrometry of steroids, photochemical transformations of steroids which have preparative value, and new methods of specific fluorination of steroids. A series of graduate lectures on selected topics has appeared. ... 

CHEMISTRY AND BIOLOGY OF STEROIDAL ALKALOIDS FROM MARINE ORGANISMS... 

Marine natural products have been extensively reviewed in many monographs and journals (1-17). Kobayashi and Ishibashi have reviewed marine alkaloids in general in this series (16), and our recent review (17) provides an account of toxic alkaloids of marine origin. This chapter is intended to provide the reader a brief description of the isolation, structure elucidation, synthetic studies, and biological screening of important classes of steroidal alkaloids and amines of marine origin. 

Chapter 4 offers an overview of the steroidal alkaloids from marine organisms by Atta-ur-Rahman and Choudhary. In addition to their unique sources and challenging structures, several of these alkaloids are currently of substantial biological interest. 

Several steroidal alkaloids have pharmaceutical interest, either because of their biological activity or as a raw material for the production of various steroids used in pharmacotherapy. Solanum glycoalkaliods (48-53) are examples of the latter. Most of the work on the production of steroidal alkaloids concerns this type of compound. 

Nino J, Correa YM, Mosquera OM. Biological activities of steroidal alkaloids from Solanum leucocarpum. Pharm Biol 2009 47(3) 255-9. 

Medium length to long (25-50 m) apolar capillary columns were shown to be best suited for the analysis of these compounds (Van Gelder et al. 1988, 1989). Figure 5 shows a GC separation of C27 steroidal alkaloids. Since different biological activities are associated with structural differences in the sugar moieties, isolation and identification of the glycosides remain necessary to examine toxicity. 

Bradley, V., D. J. Collins, F. W. Eastwood, M. C. Irvine, J. M. Swan, and D. E. Symon, Distribution of steroidal alkaloids in Australian species of Solanum in The Biology and Taxonomy of the Solanaceae (J. G. Hawkes, R. N. Lester, and A. D. Skewing, eds.), Linnear Society of London Symposium Series 7, 203-209, Academic Press, London, 1979. 

Keeler, R. F., Teratology of steroidal alkaloids, in Alkaloids Chemical and Biological Perspectives, Vol. 4 (S. W. Pelletier, ed.), 389-425, John Wiley Sons, New York, 1986. 

Roddick, J. G., Steroidal alkaloids of the Solanaceae, in Solana-ceae. Biology and Systematics (W. G. D Arcy, ed.), 201-222, Columbia University Press, New York, 1986. 

---