Solanum steroidal glycoalkaloids: structural diversity, biological activities, and biosynthesis

Abstract

Chemical structures of typical Solanum steroidal glycoalkaloids from eggplant, tomato, and potato.

High-Performance Liquid Chromatography–Mass Spectrometry Analysis of Glycoalkaloids from Underexploited Solanum Species and Their Acetylcholinesterase Inhibition Activity

“…For the Cluster 1 plants (S. melanocerasum, S. nigrum, and S. retroflexum), the primary glycoalkaloids present in all plants were 15, 17, 20, 28, and 46. In the Cluster 2 plants, three predominant compounds (16, 17, and 26) that belong to solanidine-type glycoalkaloids were present across all the species [19,34]. The clustering is consistent with the fact that S. nigrum, S. retroflexum, and S. melanocerasum belong to the Morelloid clade and have been shown to be genetically related based on morphological and molecular data [40,41].…”

“…Compounds 15 and 17 were identified against the analytical standards for solamarine and solamargine, respectively. Compounds 1 and 29 were identified as isomers of hydroxysolamargine based on the molecular ion [M + H] + of 884.50 and the aglycone fragment of 430.33, which corresponds to hydroxylated solasodine [19]. Hydroxy-solamargine was previously reported in the fruits of S. nigrum, as well as in S. melongena, in correlation with solamargine [17,18].…”

“…An aglycone with a molecular mass of 430.33 was present in four assigned glycoalkaloids. This aglycone likely corresponds to the hydroxylated solanidine [19]. A fragment corresponding to jurubidine, a cyclized 3β-aminospirostane aglycone (m/z of 416.35) was present in three compounds.…”

“…A pseudo-molecular ion of 414.33, corresponding to solanidine aglycone, was present in the MS spectra of 13 assigned glycoalkaloids. Solanidine, also known as solatubin or solanid-5-en-3-ol, contains an oxazaspirodecane ring system and is present in solamargine-and solasonine-type glycoalkaloids [19,34]. An aglycone with a molecular mass of 430.33 was present in four assigned glycoalkaloids.…”

Application of TLC and UHPLC–QTOF–MS for the identification of aqueous two-phase extracted UV–fluorescent metabolites from Solanum retroflexum

“…3b and Table 1), respectively [21]. Alpha-tomatidine was composed of a tomatidine aglycone unit glycosylated by four monosaccharides which included d-galactose, 2 × d-glucose and d-xylose, whereas tomatidine galactoside contained d-galactose as a saccharide [22]. Therefore, this indicated that the transition from m/z 1034 to m/z 578, which is alpha-tomatine to tomatidine galactoside, occurred with the loss of 3 monosaccharaides which consisted of 2 × d-glucose and d-xylose.…”