Physiological functions of solanaceous and tomato steroidal glycosides

Nohara, Toshihiro; Ikeda, Tsuyoshi; Fujiwara, Yukio; Matsushita, Sayaka; Noguchi, Eishin; Yoshimitsu, Hitoshi; Ono, M.

doi:10.1007/s11418-006-0021-y

Cited by 33 publications

(30 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Every Solanum lycopersicum L. tomato reviewed in this study including Momotaro, mini, medium, yellow and black tomatoes from Japan, and European and American varieties contains tomato saponin, esculeoside A (1), [1][2][3][4] as a major ingredient occurring at levels approximately four times higher than those of lycopene.…”

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

confidence: 99%

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

et al. 2015

Self Cite

View full text Add to dashboard Cite

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.

show abstract

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

confidence: 99%

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

et al. 2015

Self Cite

View full text Add to dashboard Cite

show abstract

“…e-mail: none@ph.sojo-u.ac.jp is metabolized into various steroidal hormones such as pregnane, which has anti-osteoporosis, anti-menopausal disorder, and anti-tumor activity in the body. 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.…”

mentioning

confidence: 99%

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

et al. 2013

Self Cite

View full text Add to dashboard Cite

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

show abstract

“…Their biosynthesis has also been implicated in the pathophysiology of cardiovascular diseases, cancer, colonic adenomas and Alzheimer's 17 .…”

mentioning

confidence: 99%

Untitled

2012

IJPSR

View full text Add to dashboard Cite

This article reviews, connected the gap between the folkloric use of Solanum nigrum and the results of evidence based experiments. Although Solanum nigrum is a rich source of one of plants most dreaded toxins solanine, it has appreciably monstrated its potential as a reservoir of antioxidants having hepatoprotective, anti-tumor, cytostatic, anti-convulsant, anti-ulcerogenic and anti-inflammatory.effects. The review encompasses in-vitro, in vivo and clinical studies done on Solanum nigrum, while examining.whether or not correct scientific measures have been taken in generating experimental evidences for its traditional uses. This review would afford research scientist to know how much is known and what is left undone in the investigation of Solanum nigrum. The compounds considered in this revieware flavonoids and other phenolics, alkaloids (especially indole terpenoid and purine alkaloids), essential oils and other terpenoids, cannabinoids, lucosinolates and isothiocyanates, and compounds having human hormone activity. The review concludes with a discussion of the possible evolutionary mechanisms that have led to the evolution of UV-B regulation of secondary metabolite accumulation. Many Ayurveda philosophers and healers praised about the properties of this plant and utilized in various disorders. Here, a review made on the screening of Solanum nigrum for various activities. It is found that the drug is very potential and can be used for various applications as mentioned in Ayurveda. Black nightshade grows as a weed, found in the dry parts of India and other parts of the world. It has a medicinal usage and has been used as a traditional folk medicine for treating various ailments such as pain, fever and liver disorders. Generally, black nightshade is very rich in nutritive values, which are capable of supplying minerals, vitamins, hormones and proteins. This herb elaborates a wide variety of medicinal properties such as anticancer, antioxidant, neuroprotective, cytoprotective, antimicrobial, antinociceptive and antipyretic properties.

show abstract

Physiological functions of solanaceous and tomato steroidal glycosides

Cited by 33 publications

References 42 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

Untitled

Contact Info

Product

Resources

About