Solanum glycoalkaloids

Figure 1. Aglycone skeletons of fungitoxic steroidal saponins and Solanum glycoalkaloids.

Acyl carrier protein, fatty acid synthase sequence, 45-46 Acyl carrier protein derivatives, desaturation, 13,l4f Acyl lipids, formation, 47-48 Aglycone skeletons saponins, 288f Solanum glycoalkaloids, 288f... 

Some Solanum glycoalkaloids have been characterized by GC-MS analysis of their permethyl derivatives (60, 170 cf. 370) and determined in living plants and herbarium specimens by use of a radioimmunoassay (371). Like digitonin and a-tomatine, the steroidal gjycoalkaloid mixture from potato (a-solanine and a-chaconine) is able to complex with 3/ -hydroxysterols in vitro (370) which can be used for the quantitative analysis of these alkaloids (379). 

Kuo KW, Hsu SH, Li YP, Lin WL, Uu LF, Chang LC, Un CC, Lin CN, Sheu HM (2000) Anticancer activity evaluation of the Solanum glycoalkaloid solamaigjne. Triggering apoptosis in human hepatoma cells. Biochem Pharmacol 60 1865-1873 Kupchan SM, Barboutis SJ, Know JR, Lau Cam CA (1965a) Beta-solamarine Tumor inhibitor... 

Figure 1 illustrates structures of common and uncommon Solanum glycoalkaloids. Figure 2 depicts structures of hydrolysis products of a-chaconine and a-solanine. Figures 3 and 4 show HPLC chromatograms of a-chaconine and a-solanine and hydrolysis products, and Figure 5 correlates HPLC and immunoassay measurements of potato glycoalkaloids. 

Wszelaki AL, Delwiche JF, Walker SD, Liggett RE, Scheerens JC and Kleinhenz MD (2005) Sensory quality and mineral and glycoalkaloid concentrations in organically and conventionally grown redskin potatoes (Solanum tuberosum). Journal of the Science of Food and Agriculture, 85, 720-726. 

Sanford L L, Deahl K L, Sinde S L and Ladd Jr T L (1992), Glycoalkaloid content in tubers from Solanum tuberosum populations selected for potato leafhopper resistance , Am Potato J, 69, 693-703. 

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. 

Johns, T., Alonso, J. G. (1990). Glycoalkaloid change during the domestication of the potato, Solanum Section Petota. Euphytica, 50, 203-210. 

Sorensen, K. K., Kirk, H. G., Olsson, K, Labouriau, R., Christiansen, J. (2008). A major QTL and an SSR marker associated with glycoalkaloid content in potato tubers from Solanum tuberosum x S. sparsipilum located on chromosome I. Theoretical and Applied Genetics, 117, 1-9. 

Yencho, G. C., Kowalski, S. R, Kobayashi, R. S., Sinden, S. L., Bonierbale, M. W., Deahl, K. L. (1998). QTL mapping of foliar glycoalkaloid aglycones in Solanum tuberosum x S. berthaultii potato progenies quantitative variation and plant secondary metabolism. Theoretical and Applied Genetics, 97, 563-574. 

In commercial potatoes (Solanum tuberosum) there are two major glycoalkaloids, a-chaconine and a-solanine, both trisaccharides of the common aglycone solanidine. These two compounds comprise about 95% of the glycoalkaloids in potato tubers. Their hydrolysis products, the p and 7 forms and solanidine, may also be present in relatively insignificant concentrations. The structures of these glycoalkaloids and their hydrolysis products are presented in Figure 6.1. 

Brown, C. R., Gulley, D., Yang, C. -P, Durst, R., Wrolstad, R. (2005). Variation of anthocyanin and carotenoid contents and associated antioxidant values in potato breeding lines. J. Am. Soc. Hortic. ScL, 130, 174-180. Brown, M. S., McDonald, G. M., Friedman, M. (1999). Sampling leaves of young potato Solanum tuberosum) plants for glycoalkaloid analysis. J. Agric. Food Chem., 47,2331-2334. 

Kozukue, N., Yoon, K. S., Byun, G. L, Misoo, S., Levin, C. E., Friedman, M. (2008). Distribution of glycoalkaloids in potato tubers of 59 accession of two wild and five cultivated Solanum species. J. Agric. Food Chem., 56, 11920-11928. 

Laha, M. K., Basu, P. K. (1983). Biological hydrolysis of glycoalkaloids from Solanum khasianum by a local strain of Aspergillus niger. Int. J. Crude Drug Res., 21, 153-155. 

Morris, S. C., Lee, T. FI. (1984). The toxieity and teratogenicity of Solanaceae glycoalkaloids, particularly those of the potato (Solanum tuberosum) a review. Food technology in Australia, 36,118-124. 

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. 

Chromatographic analysis of glycoalkaloids can be performed in a number of ways (321,322). The intact compounds can be analyzed by GC after derivatization (323). After hydrolysis the aglycone skeleton can be examined by GC without the need of derivatization (324). For routine determinations of the glycoalkaloids present in potato tubers, HPLC is probably the method of choice. Column acidity caused by active silanol sites on the packing surface strongly influences the chromatographic separation of Solanum alkaloids. In fact, basic compounds react with... 

The solasodine-based glycoalkaloids solamargine and solasonine were isolated from ripe fruits of 5. acculeatissimum. The total solasodine content of these fruits was 3.8%.35 The same glycoalkaloids were found in tissue cultures of S. acculeatissimum,36 while solasodine was isolated from tissue cultures of five Solanum... 

A glycoalkaloid present in various species of Solanum, particularly S. tuberosum (Solanaceae). 

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