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Solanine (Nightshade Glycoalkaloids)
Published in Dongyou Liu, Handbook of Foodborne Diseases, 2018
Filomena Lelario, Laura Scrano, Sabino Aurelio Bufo, Maryam Bader, Donia Karaman, Ameen Thawabteh, Rafik Karaman
The major solanidane-type components of a comprehensive family of SGA are α-solanine and α-chaconine in potato plants (Solanum tuberosum). The spirosolane-type GA, solasonine and solamargine, are the major components of eggplant. Their structures contain the same core aglycone structure, solasodine, and a three-sugar unit (solatriose or chacotriose), that determines the structural difference. Solasodine-derived alkaloids do not have a marked toxicity as do solanidine-derived compounds, although they have some estrogenic effect that may affect male fertility and disrupt the cell membrane, resulting in alterations in the liver and central nervous system. Some beneficial and medicinal properties have been described for solamargine and solasonine such as inducing apoptosis in human cancer cells, cytolysis of the parasite Trypanosoma cruzii, and treating herpes viruses.
Steroidal Alkaloids
Published in Amritpal Singh Saroya, Contemporary Phytomedicines, 2017
Solasonine (Fig. 21.13) is a glycoalkaloid derived from solasodine. Solauricidine is the poisonous aglycone chemical compound of the glycoalkaloid solauricine. It closely resembles an isomer of solasonine. Solauricine is found in Solanum mauritianum Scop.
Catalog of Herbs
Published in James A. Duke, Handbook of Medicinal Herbs, 2018
Bittersweet contains the alkaloid solanine, which acts narcotically, and the glucoside dulcamarine. Glycoalkaloids present in the plant include: alpha-, beta-, and gamma-solad-ulcine (aglycone, soladulcidine [solasodan-3-ol], and alpha-, beta-, and gamma-solamarine (aglycone, delta-5-tomatiden-3 beta-ol). An isomer of gamma-solamarine, viz. gamma-solamarine, and a derhamnosyl derivative of alpha-solamarine, named delta-solamarine, have been identified. Soladulcine is tetraoside of soladulcidine, the sugars identified in the hydrolysate of the glycoalkaloid being d-xylose, l-rhamnose, d-galactose, and d-glucose. Alpha-solamarine is a trisaccharide of tomatiden-3 beta-ol, the sugar components being d-glucose, d-galactose, and l-rhamnose; the sugar components of beta- and gamma-solamarines are, respectively, d-glucose and l-rhamnose (2 mol); and d-glucose and l-rhamnose. The presence of solanine, solasonine, and solamargine in the plant has also been reported. Yamogenin, tigogenin, and diosgenin are present; the first two compounds occur in high concentrations in the inflorescence of the plant. From the roots, 15 alpha-hydroxy-sola-dulcidine, 15 alpha-hydroxysolasodine, 15 alpha-hydroxytomatidine, and 15 alpha-hydrox-ytomatidenol have been isolated. Green and yellowing fruits contain a higher percentage of glycoalkaloids than the ripe (red) fruits. As the fruit ripens, the glycoalkaloids and their aglycones tend to disappear, while the nitrogen-free sapogenins remain. Wild plants contain soladulcidine, while cultivated forms contain either soladulcidine or 5-tomatiden-3-beta-ol, or both.1 Fruits contain lycopene. A monohydroxy lycopene, lycoxanthin (C40H56O), and a dihydroxy lycopene, lycophyll (C40H56O2), have been identified. Resins, saponins, and tannins are also reported.27 Leaves contain the galactosides from cholesterol, brassicasterol, campesterol, stigmasterol, and beta-sitosterol and their palmitic-acid esters.33 Willuhn and May300 identified from tissue cultures the 4,4-dimethylsterols cycloartenol, cycloartanol 24-dihydrolanosterol, and 24-methylenecycloartanol, and the sterols cholesterol, 24-methyle-necholesterol, campesterol, stigmasterol, isofucosterol, and sitosterol. The main fatty acids of the petrolether soluble lipids of the callus are palmitic-, linoleic-, and linolenic-acid. On p. 99 of the same journal, Willuhn et al. report still other compounds from the seeds, e.g., tigogenin, diosgenin, soladulcidine, solasodine, 31-norlanosterol, lophenol, obtusifoliol, gramisterol, and citrostadienol.
Solanaceae glycoalkaloids: α-solanine and α-chaconine modify the cardioinhibitory activity of verapamil
Published in Pharmaceutical Biology, 2022
Szymon Chowański, Magdalena Winkiel, Monika Szymczak-Cendlak, Paweł Marciniak, Dominika Mańczak, Karolina Walkowiak-Nowicka, Marta Spochacz, Sabino A. Bufo, Laura Scrano, Zbigniew Adamski
Among the representatives of steroidal glycoalkaloids are alkaloids produced by the Solanaceae plant family, such as α-solanine, α-chaconine, α-solamargine, α-solasonine, and α-tomatine. These compounds are commonly found in many popular food products containing tomatoes, potatoes, or eggplants (Friedman 2004). Solanaceae glycoalkaloids (SGAs) show high biological activity. For vertebrates, SGAs were shown to decrease respiratory activity and blood pressure and to cause bradycardia and haemolysis; at high concentrations they have hepatotoxic activity and can act as irritating agents within the digestive tract (Friedman 2006). Their teratogenic activity was also confirmed (Blankemeyer et al. 1998).
Neuroprotective properties of solanum leaves in transgenic Drosophila melanogaster model of Alzheimer's disease
Published in Biomarkers, 2022
Opeyemi B. Ogunsuyi, Tosin A. Olasehinde, Ganiyu Oboh
Furthermore, it is crucial to note that these observed protective effects of the leaves could be associated with their constituent phytochemicals especially polyphenols and alkaloids as previously reported. (Ogunsuyi et al. 2021b) and shown in supplementary shown in tables S1 and S2, The identified phenolics include, luteolin, catechin derivatives, caffeic acid, chlorogenic acid and dihydroxycoumarin. Similarly, alpha solanine, alpha solasodine chaconine, solanidine, solamargine, demissine and solasonine were alkaloids. Caffeic acid, luteolin, coumarin, catechin, and chlorogenic acid found in both AE and BN leaves have been found to have antioxidant effects (Rice-Evans et al. 1997, Shahidi and Ambigaipalan 2015). Furthermore, plant alkaloids in particular have been proven to have neurological effects, with many of them possessing anticholinesterase and antimonoamine oxidase properties (Kong et al. 2004, Oboh et al. 2018, Ortiz et al. 2018). Specifically, Bushway et al. (Bushway et al. 1987) observed anticholinesterase activity in two solanaceous glycoalkaloids (-chaconine, -solanine) and two alkaloids (solanidine, and demissidine) isolated in both AE and BN leaves, while Kielczewska et al., (Kiełczewska et al. 2021) recently reported neuroprtoective properties and anticholinesterase effects of solasodine analogues. In addition Huang et al (Huang et al. 2013) reported that caffeic acid ameliorated impairment to BACE-1 in acrolein-induced neurotoxicity in mice, while Arai et al (Arai et al. 2016) and Sul et al., (Sul et al. 2009) reported it exhibited anti-amyloidogenic properties and protected against Aβ-induced neurotoxicity in PC12 neuronal cell line. Also, Ali et al (Ali et al. 2019) showed that luteolin was able to offer therapeutic potentials against transgenic drosophila model of AD expressing human Aβ42 by combination of antiamyloidogenic, anticholinesterase, antiapoptotic and antioxidant properties. Consequently, these constituent phytochemicals, found in both AE and BN leaves, possibly working independently and/or their interactions could be responsible for the multifactorial neuroprotective properties observed in this study.