Esculeoside A

This natural product can be obtained using column chromatographies of high-porous polystyrene gels and reversed silica gels from a methanolic extract of many varieties of tomatoes. It will appear as colorless needles when synthesized using this method. == Biosynthesis ==

Evidence suggests that α-tomatine is a precursor of esculeoside A. In order for α-tomatine to be converted to esculeoside A, isomerization of the F-ring is required. The mechanism for this reaction is unclear at this time but research from Iijima and colleagues in 2009 suggest a glycosylation step in the putative pathway from α-tomatine to esculeoside A depends on the plant hormone ethylene. == Occurrence ==

Potatoes, eggplant, and tomatoes are all solanaceous plants that contain unique glycoalkaloids. == Potential health benefits ==

Studies have shown esculeoside A may be metabolized into derivatives that perform various beneficial activities in the human body including anti-osteoporosis, anti-menopausal disorder and anti-tumor activities. The potential health benefits of esculeoside A appear to change with factors such as the age of the tomato fruit, the heat used in processing tomatoes, and the pH used in processing. The highest amounts of esculeoside A were found in the outer skin and wall (pericarp wall) of the tomato fruit. Mature tomatoes tended to show higher amounts of esculeoside A than extracts taken from immature tomatoes. Extracts of esculeoside A in the Katsumata study were shown to be stable when heated until the point of 225 °C. This same study found esculeoside A extracts in water at pH 7-11 were stable throughout the heat sterilization process but unstable under acidic conditions. Collectively, research suggests daily intake of esculeoside A from tomatoes could have many benefits. ==References==