Glycoalkaloids, steroid

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. 

Steroidal Alkaloids and Steroidal Glycoalkaloids Norditerpenoid Alkaloids Pyrrolizidine Alkaloids Indolizidine and Polyhydroxy Alkaloids Tropane Alkaloids Glycosides... 

ID TOCSY was used extensively in the proton assignment and structural characterization of glycoalkaloids, such as saponins [29, 35, 37, 38], where the assignment of both the steroidal and the carbohydrate parts of the molecules can benefit from the sequential connectivity information provided by this technique. 

Fig. 1A-C. Examples of different classes of saponins A the triterpenoid saponin avenacin A-1 from roots of Avena spp B the steroidal saponin gracillin, from Costus speciosus C the steroidal glycoalkaloid a-tomatine from tomato (Lycopersicon spp.)...

Krits, R, Fogelman, E., Ginzberg, I. (2007). Potato steroidal glycoalkaloid levels and the expression of key isoprenoid metabolic genes. Planta, 227, 143-150. 

Benilova, I. V., Arkhypova, V. M., Dzyadevych, S. V, Jaffrezic-Renault, N., Martelet, C., Soldatkin, A. P. (2006). Kinetic properties of butyrylcholinesterases immobilised on pH-sensitive field-effect transistor surface and inhibitory action of steroidal glycoalkaloids on these enzymes. Ukr. Biokhim. 7h., 78,131-141. 

Friedman, M., McDonald, G. M. (1999b). Steroidal glycoalkaloids. In R. Ikan (Ed.), Naturally Occurring Glycosides Chemistry, Distribution and Biological Properties (pp. 311-342). Wiley, New York and London. 

Heflmann, E. (1967). Biochemistry of steroidal saponins and glycoalkaloids. Floydia, 30,209-230. 

Kuronen, R, Vaananen, T., Pehu, E. (1999). Reversed-phase liquid chromatographic separation and simultaneous profiling of steroidal glycoalkaloids and their aglycones. J. Chromatogr. A, 863,25-35. 

McCue, K. F., Shepherd, L. V. T., Allen, P. V, Maccree, M. M., Rockhold, D. R., Corsini, D. L., Davies, H. V, Belknap, W. R. (2005). Metabolic compensation of steroidal glycoalkaloid biosynthesis in transgenic potato tubers using reverse genetics to confirm the in vivo enzyme function of a steroidal alkaloid galactosyltransferase. Plant science, 168, 267-273. 

Roddiek, J. G., Weissenberg, M., Leonard, A. L. (2001). Membrane disruption and enzyme inhibition by naturally-oeeurring and modified ehaeotriose-eontaining Solanum steroidal glycoalkaloids. Phytochemistry, 56,603-610. 

Sesbinia sesbin (L.) Merrill. Indian Tian Qing (root, leaf, bark, seed)57 Saponins, triterpene glycosides, steroid glycosides, glycoalkaloids, kaempferol trisaccharide.342 343 344 Diuretic, irregular menses, externally for bug bites, antitumor. 

Saponins are found in many major food crops and include a large number of examples of constitutive plant compounds with antimicrobial activity. Their name refers to the property of forming a stable foam when shaken with water, and they consist of triterpenoid, steroid or steroidal glycoalkaloid molecules bearing one or more sugar chains. Excellent general reviews on saponins have been published recently [2-6]. 

Fig. (1). Structure of the steroidal glycoalkaloid a-tomatine showing the aglycone moiety (tomatidine) and the tetrasaccharide moiety (p-lycotetraose).

Roddick, J.G. Complex formation between solanaceous steroidal glycoalkaloids and free sterols in vitro. Phytochemistry 1979 18 1467-1470. 

Transform Mass Spectrometry Mass Spectra of Glycoalkaloids and Steroid Glycosides," Biomed. and Env. Mass Spectrom., 13, 19-204 (1986). 

Two new steroidal alkaloids, 25-isosolafloridine (43a) and solacallinidine (43b), were isolated from among the hydrolysis products of the crude glycoalkaloids of S. callium.26 The two alkaloids had similar formulae, C27H45NO2 and C27H46N2O... 

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... 

Figure 7.13 Distribution of tropane and steroidal glycoalkaloids in the family Solanaceae. (After Wink, 2003.) (See Plate 19 in colour plate section.)...

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