Tomato New Sapogenols, Isoesculeogenin A and Esculeogenin B

Yoshizaki, Miho; Matsushita, Sayaka; Fujiwara, Yukio; Ikeda, Tsuyoshi; Ono, M.; Nohara, Toshihiro

doi:10.1248/cpb.53.839

Cited by 14 publications

(9 citation statements)

References 6 publications

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“…As described above, only lycoperoside H (3) significantly increased the SC ceramide contents at 10 µM among the tomato seed saponins (1)(2)(3)(4)(6)(7)(8). Thus, we next evaluated the concentration dependency of lycoperoside H (3).…”

Section: Effects Of Tomato Seed Saponins (1-46-8) On the Ceramide Contents In Sc Of Rhek Modelsmentioning

confidence: 99%

“…As a result of the screening for active compounds for skin hydration using HaCaT cells, tomato seed saponins (1-4,6-8) were selected as the candidates which upregulate the mRNA expression of factors related to epidermal hydration. As a next step, we evaluated the effect of TSE and tomato seed saponins (1)(2)(3)(4)(6)(7)(8) on TEWL in RHEK models and whether they have hydrating activity. TSE (10 µg/mL) significantly decreased TEWL on days 5 and 7 (Figure 2A).…”

Section: Effects Of Tse and Saponins (1-46-8) On Tewl In Rhek Modelsmentioning

confidence: 99%

“…Figure 3A shows the effects of tomato seed saponins (1)(2)(3)(4)(6)(7)(8) on SC ceramide contents in RHEK models. Among tomato seed saponins, only lycoperoside H (3) significantly increased the total ceramide contents, and tigogenin 3-O-β-solatrioside (7) slightly increased the total ceramide contents but the difference was not significant.…”

Section: Effects Of Tomato Seed Saponins (1-46-8) On the Ceramide Contents In Sc Of Rhek Modelsmentioning

confidence: 99%

“…Among these, previous works regarding tomato saponins are limited. The spirosolane types of steroidal saponins have been isolated as lycoperosides [2,3] and escleosides [4][5][6][7] from tomato. Regarding the biological activities of these steroidal saponins, Fujiwara et al have reported that the oral administration of esculeoside A reduced serum cholesterol and low-density lipoprotein-cholesterol in apolipoprotein Edeficient mice [8].…”

Section: Introductionmentioning

confidence: 99%

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Lycoperoside H, a Tomato Seed Saponin, Improves Epidermal Dehydration by Increasing Ceramide in the Stratum Corneum and Steroidal Anti-Inflammatory Effect

et al. 2021

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Tomatoes are widely consumed, however, studies on tomato seeds are limited. In this study, we isolated 11 compounds including saponins and flavonol glycosides from tomato seeds and evaluated their effects on epidermal hydration. Among the isolated compounds, tomato seed saponins (10 µM) significantly increased the mRNA expression of proteins related to epidermal hydration, including filaggrin, involucrin, and enzymes for ceramide synthesis, by 1.32- to 1.91-fold compared with the control in HaCaT cells. Tomato seed saponins (10 µM) also decreased transepidermal water loss by 7 to 13 g/m2·h in the reconstructed human epidermal keratinization (RHEK) models. Quantitative analysis of the ceramide content in the stratum corneum (SC) revealed that lycoperoside H (1–10 µM) is a promising candidate to stimulate ceramide synthesis via the upregulation of ceramide synthase-3, glucosylceramide synthase, and β-glucocerebrosidase, which led to an increase in the total SC ceramides (approximately 1.5-fold) in concert with ceramide (NP) (approximately 2-fold) in the RHEK models. Evaluation of the anti-inflammatory and anti-allergic effects of lycoperoside H demonstrated that lycoperoside H is suggested to act as a partial agonist of the glucocorticoid receptor and exhibits anti-inflammatory effects (10 mg/kg in animal test). These findings indicate that lycoperoside H can improve epidermal dehydration and suppress inflammation by increasing SC ceramide and steroidal anti-inflammatory activity.

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Section: Effects Of Tomato Seed Saponins (1-46-8) On the Ceramide Contents In Sc Of Rhek Modelsmentioning

confidence: 99%

Section: Effects Of Tse and Saponins (1-46-8) On Tewl In Rhek Modelsmentioning

confidence: 99%

Section: Effects Of Tomato Seed Saponins (1-46-8) On the Ceramide Contents In Sc Of Rhek Modelsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Lycoperoside H, a Tomato Seed Saponin, Improves Epidermal Dehydration by Increasing Ceramide in the Stratum Corneum and Steroidal Anti-Inflammatory Effect

et al. 2021

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“…[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.…”

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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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