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Esculeoside A (2), a spirosolane steroidal glycoside, is a major constituent isolated from Solanum lycopersicum, a commercial strain of mini tomatoes. The content variability of esculeoside A (2) was examined in mini, midi, and Momotaro tomatoes and various processed tomato products. In the green immature tomato fruit, tomatine (1) is oxidized at C-23 and C-27 to produce esculeoside A (2) in the ripe fruit. Further, esculeoside A (2) is partly converted to 3β-hydroxy-5α-pregn-16-en-20-one 3-O-β-lycotetraoside (6), a pregnane glycoside, in the overripe fruit. Esculeogenin A (3), the sapogenol of 2, is easily converted into 3β,16β-dihydroxy-5α-pregn-20-one (17). Metabolic studies showed excretion of androstane derivatives in the urine of human volunteer subjects after tomato consumption. Esculeogenin A (3) inhibited the accumulation of cholesterol esters in macrophages through its effects on acyl-Co
cholesterol acyl transferase (ACAT). Oral administration of esculeoside A (2) to apoE-deficient mice significantly reduced serum levels of cholesterol, triglycerides, and LDL-cholesterol and ameliorated the severity of atherosclerotic lesions.
Faculty of Pharmaceutical Sciences, Sojo University, 22-1, 4-Chome, Ikeda, Kumamoto 860-0082, Japan, School of Agriculture, Tokai University, 5435, Aso, Kumamoto 869-1404, Japan, Graduate School of Pharmaceutical Sciences, Faculty of Life Sciences, Kumamo
This article was published in the following journal.
Name: Journal of natural products
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The aglucon moiety of a saponin molecule. It may be triterpenoid or steroid, usually spirostan, in nature.
A highly toxic saponin occurring in HOLOTHUROIDEA. This marine toxin is an anionic surfactant, hemolyzing ERYTHROCYTES.
A plant genus of the family LILIACEAE. Members contain benzoquinones, steroidal saponin, and ribosome-inactivating proteins.
A species of gram-negative bacteria, in the genus XANTHOMONAS, causing disease in TOMATO and pepper crops.
A plant genus of the family LILIACEAE. Members contain anemarans (POLYSACCHARIDES), hinokiresinol, mangiferin (a xanthone), and timosaponin (a steroidal saponin).
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