Conversion of esculeoside A into esculeogenin B.
نویسندگان
چکیده
Conversion of the spirosolane-type glycoside, esculeoside A, a major component contained in the ripe tomato Lycopersicon esculentum fruits, into a solanocapsine-type sapogenol, esculeogenin B-2, (5alpha,22S,23R,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, and esculeogenin B-1, (5alpha,22R,23S,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, which are rare naturally occurring compounds was attained by acid hydrolysis with 2 N HCl in dioxane and water (1 : 1).
منابع مشابه
Esculeogenin A, a new tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in ApoE-deficient mice by inhibiting ACAT.
OBJECTIVE We recently identified esculeoside A, a new spirosolane-type glycoside, with a content in tomatoes that is 4-fold higher than that of lycopene. In the present study, we examined the effects of esculeoside A and esculeogenin A, a new aglycon of esculeoside A, on foam cell formation in vitro and atherogenesis in apoE-deficient mice. METHODS AND RESULTS Esculeogenin A significantly inh...
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Previously, we reported an interesting reaction by which esculeogenin A [(5alpha,22S,23S,25S)-3beta,23,27-trihydroxyspirosolane], a sapogenol of tomato-saponin, esculeoside A, was easily converted into a pregnane derivative, 5alpha-pregn-16-en-3beta-ol-20-one, merely by refluxing with pyridine and water. Its chemical mechanism including air oxidation is here described.
متن کاملChem. Pharm. Bull. 55(7) 1079—1081 (2007)
and their glycosides are normally 22R configuration. On the other hand, spirosolanes such as tomatidine, solasodine and their glycosides take both 22R and 22S configurations (Chart 1). To determine the configuration at C-22 is very important, because the difference in C-22 configuration relates to the chemical reactions and bio-activity, for example, as shown in the following reaction of spiros...
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متن کاملNew solanocapsine-type tomato glycoside from ripe fruit of Solanum lycopersicum.
A new solanocapsine-type tomato glycoside, a novel and interesting natural steroidal glycoside, was isolated from a mini tomato, Solanum lycopersicum L. The chemical structure of the new minor glycoside, esculeoside B-5 (3), was determined to be (5S,22R,23S,24R,25S)-22,26-epimino-16β,23-epoxy-3β,23,24-trihydroxycholestane 3-O-β-lycotetraoside.
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ورودعنوان ژورنال:
- Chemical & pharmaceutical bulletin
دوره 56 7 شماره
صفحات -
تاریخ انتشار 2008