Content variations of the tomato saponin esculeoside A in various processed tomatoes

It has been shown that commercial tomato juice packaged in 900 g plastic bottles contains rare, naturally occurring steroidal solanocapsine-type tomato glycosides in which the saponins consist of esculeosides B-1 (2) and B-2 (3) in 0.041% as major components lacking esculeoside A. We suggest that these saponins are derived from esculeoside A (1) when the juice in plastic bottles is prepared by treatment with boiling water, similar to the process used in preparing canned tomatoes. Herein, the obtained tomato saponins (2) and (3) provided sapogenols esculeogenin B 1 (4) and B 2 (5), respectively, by acid hydrolysis. The former was identical to esculeogenin B previously reported, and the latter was a new sapogenol characterized to be (5α,22S,23S,25S)-22,26-epimino-16β,23-epoxy-3β,23,27-trihydroxycholestane.

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“…7) In all cases, esculeoside A (1) was a major component. Next, we investigated the tomato saponins in Italian canned tomatoes.…”

Section: Saponins Esculeosides B-1 and B-2 Inmentioning

confidence: 90%

Saponins, Esculeosides B-1 and B-2, in Tomato Juice and Sapogenol, Esculeogenin B<sub>1</sub>

et al. 2015

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“…16,17) In previous work, we performed qualitative analyses of fresh tomato, tomato boiled in water, tomato heated in a microwave oven, freeze-dried tomato, and processed tomatoes from plastic bottles and cans before their development for health foods. 18) In all cases, esculeoside A was a major component. In this work, we investigated the tomato saponins in Italian canned tomatoes.…”

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confidence: 89%

Saponins Esculeosides B-1 and B-2 in Italian Canned Tomatoes

et al. 2013

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Italian canned tomatoes contain the tomato glycosides esculeosides B-1 (1, 0.0052%) and B-2 (2, 0.0068%) without esculeoside A. Herein, the structure of esculeoside B-1 (1) is characterized to be 3-O-β-lycotetraosyl (5S,22R,23S,25S)-22,26-epimino-16β,23-epoxy-3β,23,27-trihydroxycholestane 27-O-β-d-glucopyranoside. We hypothesized that these substances might be derived from esculeoside A when the cans are prepared with treatment in boiling water. To confirm that hypothesis, we refluxed esculeoside A with water for 6.5 h, providing esculeosides B-1 (1) and B-2 (2) in yields of 25.8% and 31.0%, respectively. Key words Solanum lycopersicum; canned tomato; tomato saponin; esculeoside A; esculeoside B-1; esculeoside B-2In 2003, Nohara and colleagues 1,2) isolated a tomato saponin, called esculeoside A, from the ripe fruits of tomato, Solanum lycopersicum L. and determined its structure ( Fig. 1). Tomato saponin is a significant component of ripened tomatoes and occurs at levels approximately 4-fold higher than those of lycopene. Thus far, the bioactivity of tomato has been attributed solely to lycopene. Therefore, carrying out pharmacological examinations of esculeoside A in the near future is important.Recently, Fujiwara et al. 3) have revealed that oral administration of esculeoside A to apolipoprotein E-deficient mice significantly reduces levels of serum cholesterol glycerides, low-density lipoprotein-cholesterol and the areas of atherosclerotic lesions without any detectable side effects. Our recent studies on the constituents of Solanum plants have revealed that pregnane glycosides are accompanied by normal spirostanol and furostanol glycosides [4][5][6][7][8][9][10][11][12] ; esculeogenin A is easily converted into a pregnane derivative by refluxing with aqueous pyridine, 13) and pregnane glycoside has been obtained from the over-ripe tomato fruit. 14) These facts strongly suggest that orally administered steroidal glycosides can be metabolized into pregnane derivatives, which are a type of steroidal hormone.Therefore, in further experiments, men consumed tomatoes and their urine was collected and separated with various column chromatographies to afford 3 androstane derivatives. 15)These androsterone analogs are normally excreted; however, because no excretions were detected in the control samples, the occurrence of androsterone analogs indicated excretion via the production of progesterone by subjects that had consumed tomatoes. The tomato steroidal glycoside might stimulate the hormone secretor or perhaps is itself metabolized into the pregnane. We hypothesize that orally administered steroidal glycosides such as spirostanol, furostanol and spirosolane glycosides are metabolized, introducing a hydroxyl group at C-23. These intermediates may then be metabolized into pregnane derivatives.Thus, we conclude that the tomato saponin esculeoside A

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“…FAB-MS were obtained with a glycerol matrix in the positive ion mode using a JEOL JMS-DX300 and a JMS-DX 303 HF spectrometer. The 1 H-and 13 C-NMR spectra were measured in pyridine-d 5 with JEOL a-500 spectrometer, and chemical shifts are given on a d (ppm) scale with tetramethylsilane (TMS) as the internal standard. Column chromatographies were carried out on a Diaion HP-20 (Mitsubishi Chemical Ind., Japan), and silica gel 60 (230-400 mesh, Merck, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…In Japanese tomatoes, mini tomatoes, Momotaro tomatoes, and midi tomatoes, we were the first to identify a steroidal saponin named esculeoside A (1) as a major tomato saponin in a yield of 0.0015-0.046%. [3][4][5] From Italian tomatoes, we isolated esculeoside B-1 (2) in a yield of 0.019%. 3,4) As other minor constituents of the ripe fruits of mini, midi, and Momotaro tomatoes, we have isolated many steroidal compounds so far by using various column chromatographies on Diaion HP-20, Chromatorex NH, and silica gel, as well as high-performance liquid chromatography on octadecylsilyl (ODS) silica, as shown in Fig.…”

Section: Notementioning

confidence: 99%

New Solanocapsine-Type Tomato Glycoside from Ripe Fruit of Solanum lycopersicum

Ohno

Ono

Nohara

2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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NoteFor metabolic analysis of steroidal glycosides, 1) we selected the tomato as part of our systematic investigation of the constituents of Solanum plants. 2) We recognized that the tomato would be appropriate because we were convinced that it had steroidal glycosides, as its aerial parts and immature fruits are rich sources of tomatine. Hence, we isolated steroidal glycosides from the ripe fruit. In Japanese tomatoes, mini tomatoes, Momotaro tomatoes, and midi tomatoes, we were the first to identify a steroidal saponin named esculeoside A (1) as a major tomato saponin in a yield of 0.0015-0.046%. [3][4][5] From Italian tomatoes, we isolated esculeoside B-1 (2) in a yield of 0.019%. 3,4) As other minor constituents of the ripe fruits of mini, midi, and Momotaro tomatoes, we have isolated many steroidal compounds so far by using various column chromatographies on Diaion HP-20, Chromatorex NH, and silica gel, as well as high-performance liquid chromatography on octadecylsilyl (ODS) silica, as shown in Fig. 1. [6][7][8] Esculeoside B-1 (2) corresponds to an isomer of esculeoside A (1).9) Detailed investigation of the constituents of local Italian tomatoes, processed tomato products, and imported canned tomatoes, tomato juice, and ketchup is currently in progress. Esculeoside B-1 (2) is the first example of a solanocapsine-type steroidal alkaloid glycoside, the fundamental skeleton of which is very rare and interesting in terms of its chemical structure and unknown pharmacological activity.Here, we report one example of its rare solanocapsine-type glycoside, esculeoside B-5 (3). A commercial mini tomato was blended briefly with water by a mixer and filtered with a filter paper; the resulting filtrate was then passed through a highly porous polystyrene gel (Diaion HP-20) after elution with water. The water eluate was discarded, and further elution with MeOH was performed to produce an eluate that was evaporated to produce a residue. The MeOH eluate was also subjected to reversed-phase silica gel column chromatography on ODS and elution with 60% MeOH, of which the eluate was evaporated to give a residue. It consisted almost entirely of esculeoside A; it was further chromatographed on silica gel with CHCl 3 : MeOH : H 2 Oϭ7 : 3 : 0.

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Content variations of the tomato saponin esculeoside A in various processed tomatoes

Cited by 21 publications

References 21 publications

Saponins, Esculeosides B-1 and B-2, in Tomato Juice and Sapogenol, Esculeogenin B<sub>1</sub>

Saponins, Esculeosides B-1 and B-2, in Tomato Juice and Sapogenol, Esculeogenin B<sub>1</sub>

Saponins Esculeosides B-1 and B-2 in Italian Canned Tomatoes

New Solanocapsine-Type Tomato Glycoside from Ripe Fruit of Solanum lycopersicum

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