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Pharmacological potential of green tomato glycoalcaloids: an overview

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Glycoalkaloids are characteristic secondary metabolites in plants of the Solanaceae family. Although perceived as potentially toxic, these compounds display different bioactivities and pharmacological effects. The glycoalkaloids esculeoside A and tomatine (which comprises a junction of α-tomatine and dehydrotomatine) can be found in tomato plants. Structurally, dehydrotomatine differs from α-tomatine by having a double bond in the steroidal B ring of the aglycone; but both glycoalkaloids have the same tetrasaccharide (lycotetraose) side chain. Therefore, while α-tomatine has lycotetraose bonded to the aglycone tomatidine, dehydrotomatine has the side chain attached to the aglycone tomatidenol. Up to 500 mg/kg FW of tomatine can be found in unripe (green) tomatoes, levels that decrease with ripening (approximately 5 mg/kg FW in ripe red tomatoes) [1]. On the other hand, the content of esculeoside A, which is stored in ripe red tomatoes, is comparable to or higher than that of lycopene [2]. Thus, the levels of esculeoside A increase as the fruit matures, contrary to that observed for tomatine.

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Solanaceae family

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Pinela, José; Añibarro-Ortega, Mikel; Oliveira, Beatriz; Ferreira, Isabel C.F.R.; Barros, Lillian (2021). Pharmacological potential of green tomato glycoalcaloids: an overview. In 2021 #RSCPoster Twitter Conference

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