Lycoperosides A-C, three stereoisomeric 23-acetoxyspirosolan-3β-ol β-lycotetraosides from Lycopersicon esculentum

Yahara, Shoji; Uda, Noriko; Nohara, Toshihiro

doi:10.1016/0031-9422(95)00854-3

Cited by 35 publications

(33 citation statements)

References 5 publications

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“…The mechanism for this reaction is tentatively speculated to be as follows: the acquisition of H-20 by pyridine caused a double-bond formation between C-20 and C-22 and the opening of an E-ring, followed by dehydration of C-23-OH to form a 22(N)-ene derivative, of which nitrogen was then protonated, and the transfer of the 22(N)-ene to the nitrogen raised the bond fission between C-20 and C- 22. In the case of spirosolane, particularly tomatidine (20), normal acetylation with pyridine and acetic anhydride at room temperature yielded d 20 (22) Fig. 10 Pregnane glycoside (17) isolated from overripe tomato pregnane compound (21). Therefore, this reaction is a new method to obtain pregnane compounds without the use of diosgenin (Fig.…”

Section: Chemical Conversions Of Tomato Sapogenolsmentioning

confidence: 96%

“…Recent studies have reported the following con- stituents of tomato: a bitter component named TFI [20], was isolated from tomato seeds; steroidal alkaloid glycosides, tomatine (12), and several spirosolane glycosides were obtained from the stems and leaves [21]; lactone [22], pregnane [23] and several spirosolane derivatives [24] from the roots of the tomato stock were reported. However, the steroidal alkaloid is thought to be absent in the ripe fruit.…”

Section: Tomato Glycosidesmentioning

confidence: 99%

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Physiological functions of solanaceous and tomato steroidal glycosides

et al. 2006

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Solanaceous plants are widely distributed. They are used as food and in folk medicine. Our studies focused on these plants, starting with Solanum lyratum and S. nigrum, which are used as anti-cancer and anti-herpes agents. Extensive investigations in 45 Solanum plant species revealed that a considerable amount of glycosides such as spirosolane, solanidane, spirostane and furostane is in these plants, and some of the isolated glycosides showed strong anti-proliferative activity against various cancer cell lines and anti-herpes activity. Furthermore, we have discovered a few new hypothetical biosynthetic routes in which the pathways for the biosynthesis of 16-acyl-pregnane and pregnane glycosides were the most interesting. The occurrence of these pregnane compounds indicates that they might be internally biosynthesized in the plant from furostanol glycosides by a reaction that is similar to Marker degradation. Furthermore, this may imply that the administration of steroidal glycosides may result in their metabolization into pregnane derivatives possessing various activities. In order to perform metabolic experiments using the steroidal glycosides, we recently isolated tomato glycosides from ripe tomato fruits for the first time. For this experiment, we examined the metabolites in urine obtained from persons that consumed tomatoes. We obtained androstane derivatives that were probably metabolized via pregnane derivatives from tomato glycoside. Hence, when a steroidal glycoside is administered, it may be metabolized into a type of steroidal hormone with various physiological activities.

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Section: Chemical Conversions Of Tomato Sapogenolsmentioning

confidence: 96%

Section: Tomato Glycosidesmentioning

confidence: 99%

Physiological functions of solanaceous and tomato steroidal glycosides

et al. 2006

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“…However, ␣-tomatin is structurally different from the potato alkaloids and even beneficial health effects in humans has been suggested, as this compound was shown to inhibit growth of various human cancer cell lines (Friedman et al, 2009) and can lower LDL-cholesterol in hamsters (Friedman et al, 2000). Besides ␣-tomatin and its dehydrogenated form ␣-dehydrotomatin, tomato fruits also contain a range of other structurally related triterpenoid glycosides, such as esculeosides and lycoperosides (Yahara et al, 1996;Fujiwara et al, 2004;Moco et al, 2006Moco et al, , 2007bMintz-Oron et al, 2008;Yamanaka et al, 2008). While ␣-tomatin is the best-known and most studied triterpenoid glycoside in tomato plants, recent studies indicate that it is not the major triterpenoid in the fruit.…”

Section: Tomato Metabolomics and Human Nutritionmentioning

confidence: 99%

Metabolomics of a Model Fruit: Tomato

Vos

Hall

Moing

2011

Annual Plant Reviews Volume 43

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Tomato has quickly become a favoured species for metabolomics research. Tomato fills a niche that cannot be occupied by Arabidopsis, particularly regarding studies on fleshy fruit. Variations in genotype and phenotype have been broadly exploited using metabolomics approaches in order to gain a better understanding of fundamental aspects of plant physiology, fruit growth and fruit development. The commercial importance of tomato as one of the world's most important and widely grown and consumed vegetables is a significant driving force behind this fruit research. Therefore, many metabolomics studies have specifically been focused on traits of importance to the food and agro-industries. Fruit quality, nutritional value as well as the influence on these traits of fruit storage, transport and processing into pasteurized and cooked products have also been subjects for extensive metabolomics analyses. These studies have already considerably expanded our knowledge, and continue to do so, concerning many aspects of the tomato fruit phenotype, both visible and chemical. Furthermore, increased knowledge of the genetics of tomato, the recently available draft of the tomato genome sequence as well as the emerging technologies for next generation sequencing, large-scale phenotyping and systems biology approaches have generated many novel research concepts that are also placing metabolomics analyses of tomatoes right at the forefront of fruit research.

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“…This conclusion was also supported by the chemical shift at C-20. 4) In 22aN-spirosolane derivatives, the C-20 signals appeared around d 35.0, while in 22bN-series (C-22R), it occurred around d 43.0. Isoesculeogenin A (1) appeared at d 44.1, suggesting the configuration at C-22 to be C-22bN (C-22R).…”

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confidence: 95%