DOCSLIB.ORG

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

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Saponins Esculeosides B-1 and B-2 in Italian Canned Tomatoes 764 Note Chem. Pharm. Bull. 61(7) 764–767 (2013) Vol. 61, No. 7 Saponins Esculeosides B-1 and B-2 in Italian Canned Tomatoes Hideyuki Manabe,a Yukio Fujiwara,b Tsuyoshi Ikeda, a Masateru Ono,c Kotaro Murakami,a Jian-Rong Zhou,a Kazumi Yokomizo,a and Toshihiro Nohara*,a a Faculty of Pharmaceutical Sciences, Sojo University; 4–22–1 Ikeda, Kumamoto 860–0082, Japan: b Graduate School of Medical Sciences, Faculty of Life Sciences, Kumamoto University; 1–1–1 Honjo, Kumamoto 860–8556, Japan: and c School of Agriculture, Tokai University; 5435 Aso, Kumamoto 869–1404, Japan. Received March 11, 2013; accepted April 16, 2013 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, pro- viding 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; esculeo- side B-2 In 2003, Nohara and colleagues1,2) isolated a tomato sa- from the over-ripe tomato fruit.14) These facts strongly suggest ponin, called esculeoside A, from the ripe fruits of tomato, that orally administered steroidal glycosides can be metabo- Solanum lycopersicum L. and determined its structure (Fig. lized into pregnane derivatives, which are a type of steroidal 1). Tomato saponin is a significant component of ripened to- hormone. matoes and occurs at levels approximately 4-fold higher than Therefore, in further experiments, men consumed tomatoes those of lycopene. Thus far, the bioactivity of tomato has been and their urine was collected and separated with various col- attributed solely to lycopene. Therefore, carrying out pharma- umn chromatographies to afford 3 androstane derivatives.15) cological examinations of esculeoside A in the near future is These androsterone analogs are normally excreted; however, important. because no excretions were detected in the control samples, Recently, Fujiwara et al.3) have revealed that oral admin- the occurrence of androsterone analogs indicated excretion via istration of esculeoside A to apolipoprotein E-deficient mice the production of progesterone by subjects that had consumed significantly reduces levels of serum cholesterol glycerides, tomatoes. The tomato steroidal glycoside might stimulate the low-density lipoprotein-cholesterol and the areas of athero- hormone secretor or perhaps is itself metabolized into the sclerotic lesions without any detectable side effects. Our pregnane. We hypothesize that orally administered steroidal recent studies on the constituents of Solanum plants have glycosides such as spirostanol, furostanol and spirosolane revealed that pregnane glycosides are accompanied by normal glycosides are metabolized, introducing a hydroxyl group at spirostanol and furostanol glycosides4–12); esculeogenin A is C-23. These intermediates may then be metabolized into preg- easily converted into a pregnane derivative by refluxing with nane derivatives. aqueous pyridine,13) and pregnane glycoside has been obtained Thus, we conclude that the tomato saponin esculeoside A Fig. 1. Structure of Esculeoside A The authors declare no conflict of interest. * To whom correspondence should be addressed. e-mail: [email protected] © 2013 The Pharmaceutical Society of Japan July 2013 765 Fig. 2. Structures of Esculeoside B-1 (1) is metabolized into various steroidal hormones such as preg- is very rare. nane, which has anti-osteoporosis, anti-menopausal disorder, Compound 1 was obtained as an amorphous powder show- 16,17) and anti-tumor activity in the body. In previous work, we ing [α]D −42.6° (pyridine). Positive high-resolution fast atom performed qualitative analyses of fresh tomato, tomato boiled bombardment mass spectrometry exhibited a quasi-molecular in water, tomato heated in a microwave oven, freeze-dried ion at m/z 1228.5966 (Calcd for C56H93NO28+H: 1228.5962). tomato, and processed tomatoes from plastic bottles and cans The signals on the 1H- and 13C-NMR of 1 were very similar before their development for health foods.18) In all cases, es- to those of 2. In particular, the signals originating from the culeoside A was a major component. In this work, we investi- sugar moieties of 1 were almost superimposable on those gated the tomato saponins in Italian canned tomatoes. of 2. The sapogenol moiety of 1 showed 3 methyl groups at Commercially available Italian cans, containing 400 g of δ 0.72 (3H, s, H3-19), 0.85 (3H, s, H3-18), and 1.29 (3H, d, 1 ingredients, were chosen for the experiments in order to com- J=6.1 Hz, H3-21) in the H-NMR spectrum (pyridine-d5), and pare the respective ingredients in each cans. Trademarks of it exhibited signals assigned to C-22–C-27 on the sapogenol Matured Whole Tomatoes (Del Monte, i), Whole Tomatoes moiety at δ 61.9, 96.6, 40.2, 33.2, 42.3, and 70.4, respec- 13 (Aeon Co., Ltd., ii), Matured Whole Tomatoes (Kagome Co., tively, in the C-NMR (pyridine-d5) spectrum. Therefore, the Ltd., iii), and Whole Peeled Italian Tomatoes (Spigadoro, iv) structure of 1 was also deduced to be a solanocapsine type were used. Each was individually blended with water and glycoside—that is, a stereo-isomer of 2. The signal assigned passed through filter paper to produce a filtrate, which was to H3-21 appeared at δ 1.29 higher field than that in 2, in this then passed through a highly porous polystyrene gel (Diaion signal appeared at δ 1.62 owing to 1,3-diaxial configuration. HP-20) and rinsed with water. Methanol was then passed Therefore, in 1, the 21-Me group does not lie in a 1,3-diaxial through the gel to produce an eluate, which was evaporated configuration. Moreover, nuclear Overhauser effect was ob- to produce a residue. This methanolic residue was subjected served between H-20 and H-22 in 2 but not in 1. Consequent- to reversed phase silica gel column chromatography, octa- ly, the structure of 1 was deduced to be 3-O-β-lycotetraosyl decylsilane (ODS), and then eluted with 40%, 60%, and 100% (5S,22R,23S,25S)-22,26-epimino-16β,23-epoxy-3β,23,27-trihy- methanol. The eluate from the 40% methanol contained aro- droxycholestane 27-O-β-D-glucopyranoside, which was desig- matics, that from the 60% methanol was composed of tomato nated as esculeoside B-1. saponins, and the final methanol eluate included less polar Thus, because the saponins esculeosides B-1 (1) and B-2 (2) substances. The respective yields are shown in Experimental. were isolated from Italian canned tomatoes, we hypothesized The 60% methanol eluates from the ODS column ap- that the esculeoside A in Italian tomatoes transforms into parently lacked esculeoside A but contained esculeoside B esculeosides B-1 and B-2 when these tomatoes are canned on thin-layer chromatography with CHCl3–MeOH–water via sterilization with boiling water. Therefore, we considered (7 : 3 : 0.5, 6 : 4 : 1). Therefore, they were combined to give a whether esculeoside A would change to esculeoside B when residue (390.6 mg, 0.024%), which was then passed through refluxed with water. To investigate this question, we refluxed the ODS column again with 55% methanol to provide 2 toma- esculeoside A (104.0 mg) with water in an oil bath for 6.5 h. to saponins: 1, 85.5 mg (0.0052%) and 2, 112.0 mg (0.0068%). Using thin-layer chromatography, we found that esculeoside Compound 2 was obtained as an amorphous powder show- A was almost quantitatively converted to a more polar sub- ing [α]D −49.2° (pyridine). The results of positive high- stance. The reaction mixture was evaporated in vacuo to give resolution fast atom bombardment mass spectrometry showed a residue (98.1 mg, 97.4%), which was passed through an ODS (m/z): 1228.5964 (Calcd for C56H93NO28+H: 1228.5962). column, yielding in 2 compounds identified as esculeoside This compound was identified with the previously isolated B-1 (1, 26.0 mg, 25.8%) and B-2 (2, 31.2 mg, 31.0%). Thus, es- esculeoside B, 3-O-β-lycotetraosyl (5S,22S,23R,25S)-22,26- culeoside A is transferred into esculeosides B-1 and B-2 when epimino-16β,23-epoxy-3β,23,27-trihydroxycholestane 27-O-β- Italian tomatoes are produced in cans. Although we have re- 2) D-glucopyranoside, and renamed esculeoside B-2. This sapo- ported that esculeoside A is partly converted to esculeogenins genol moiety is called a solanocapsine type,2) and its glycoside B-1 and B-2 via refluxing with HCl in 50% aqueous diox- 766 Vol. 61, No. 7 Chart 1. Transformation of Esculeoside A into Esculeosides B-1 (1) and B-2 (2) ane,19) conversion of 1 directly into esculeoside B-1 (1) and residue was subjected to reversed phase silica gel column B-2 (2) as the glycoside only via refluxing with water has been chromatography, ODS, and then eluted with 40%, 60%, and attained for the first time. The proposed reaction mechanism 100% methanol. The eluate from the 40% methanol con- is shown in Chart 1.20) tained aromatics, that from the 60% methanol was composed Thus, we showed that Italian canned tomatoes contain of tomato saponins, and the final methanol eluate included tomato glycosides esculeosides B-1 (1) and B-2 (2), and we less polar substances.
Load more

Recommended publications
  • Bioactive Compounds of Tomatoes As Health Promoters
    48 Natural Bioactive Compounds from Fruits and Vegetables, 2016, Ed. 2, 48-91 CHAPTER 3 Bioactive Compounds of Tomatoes as Health Promoters José Pinela1,2, M. Beatriz P. P Oliveira2, Isabel C.F.R. Ferreira1,* 1 Mountain Research Centre (CIMO), ESA, Polytechnic Institute of Bragança, Campus de Santa Apolónia, Ap. 1172, 5301-855 Bragança, Portugal 2 REQUIMTE/LAQV, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, n° 228, 4050-313 Porto, Portugal Abstract: Tomato (Lycopersicon esculentum Mill.) is one of the most consumed vegetables in the world and probably the most preferred garden crop. It is a key component of the Mediterranean diet, commonly associated with a reduced risk of chronic degenerative diseases. Currently there are a large number of tomato cultivars with different morphological and sensorial characteristics and tomato-based products, being major sources of nourishment for the world’s population. Its consumption brings health benefits, linked with its high levels of bioactive ingredients. The main compounds are carotenoids such as β-carotene, a precursor of vitamin A, and mostly lycopene, which is responsible for the red colour, vitamins in particular ascorbic acid and tocopherols, phenolic compounds including hydroxycinnamic acid derivatives and flavonoids, and lectins. The content of these compounds is variety dependent. Besides, unlike unripe tomatoes, which contain a high content of tomatine (glycoalkaloid) but no lycopene, ripe red tomatoes contain high amounts of lycopene and a lower quantity of glycoalkaloids. Current studies demonstrate the several benefits of these bioactive compounds, either isolated or in combined extracts, namely anticarcinogenic, cardioprotective and hepatoprotective effects among other health benefits, mainly due to its antioxidant and anti-inflammatory properties.
    [Show full text]
  • Tomato Juice Saponin, Esculeoside B Ameliorates Mice Experimental Dermatitis
    Functional Foods in Health and Disease 2018; 8(4): 228-241 Page 228 of 241 Research Article Open Access Tomato juice saponin, esculeoside B ameliorates mice experimental dermatitis *Jian-Rong Zhou, Jun Urata, Takuya Shiraishi, Chiaki Tanaka, Toshihiro Nohara, Kazumi Yokomizo Department of Presymptomatic Medical Pharmacology, Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto 860-0082, Japan Corresponding author: Jian-Rong Zhou, PhD, Department of Presymptomatic Medical Pharmacology, Faculty of Pharmaceutical Sciences, Sojo University, 4-22-1 Ikeda, Nishiku, Kumamoto 860-0082, Japan Submission Date: February 16th, 2018, Acceptance Date: April 27th, 2018, Publication Date: April 30th, 2018 Citation: Zhou J., Urata J., Shiraishi T., Tanaka C., Nohara T., Yokomizo K., Tomato juice saponin, esculeoside B ameliorates mice experimental dermatitis. Functional Foods in Health and Disease 2018; 8(4): 228-241 ABSTRACT Background: Allergic diseases like atopic dermatitis have recently increased. A naturally occurring glycoside, Esculeoside B, has been identified as a major component in tomato juice from the can. Accordingly, the present study investigated the effects of esculeoside B on experimental dermatitis mice. Results: Oral treatment with 10 mg/kg of esculeoside B on the experimental dermatitis mice for 4 weeks significantly decreased the skin clinical score of 2.0 compared to the control score of 5.0. Furthermore, the scratch frequency of mice treated with esculeoside B was lower compared to the Functional Foods in Health and Disease 2018; 8(4): 228-241 Page 229 of 241 control group. Overall, the administration of esculeoside B significantly inhibited T lymphocyte proliferation and demonstrated a tendency to decrease in IL-4 production.
    [Show full text]
  • A High-Throughput Extraction and Analysis Method for Steroidal Glycoalkaloids in Tomato
    fpls-11-00767 June 19, 2020 Time: 15:23 # 1 METHODS published: 18 June 2020 doi: 10.3389/fpls.2020.00767 A High-Throughput Extraction and Analysis Method for Steroidal Glycoalkaloids in Tomato Michael P. Dzakovich1, Jordan L. Hartman1 and Jessica L. Cooperstone1,2* 1 Department of Horticulture and Crop Science, The Ohio State University, Columbus, OH, United States, 2 Department of Food Science and Technology, The Ohio State University, Columbus, OH, United States Tomato steroidal glycoalkaloids (tSGAs) are a class of cholesterol-derived metabolites uniquely produced by the tomato clade. These compounds provide protection against biotic stress due to their fungicidal and insecticidal properties. Although commonly reported as being anti-nutritional, both in vitro as well as pre-clinical animal studies have indicated that some tSGAs may have a beneficial impact on human health. However, the paucity of quantitative extraction and analysis methods presents a major obstacle for determining the biological and nutritional functions of tSGAs. To address Edited by: this problem, we developed and validated the first comprehensive extraction and Heiko Rischer, VTT Technical Research Centre ultra-high-performance liquid chromatography tandem mass spectrometry (UHPLC- of Finland Ltd., Finland MS/MS) quantification method for tSGAs. Our extraction method allows for up to 16 Reviewed by: samples to be extracted simultaneously in 20 min with 93.0 ± 6.8 and 100.8 ± 13.1% José Juan Ordaz-Ortiz, Instituto Politécnico Nacional recovery rates for tomatidine and alpha-tomatine, respectively. Our UHPLC-MS/MS (CINVESTAV), Mexico method was able to chromatographically separate analytes derived from 18 tSGA peaks Elzbieta˙ Rytel, representing 9 different tSGA masses, as well as two internal standards, in 13 min.
    [Show full text]
  • Anticarcinogenic, Cardioprotective, and Other Health Benefits Of
    Review pubs.acs.org/JAFC Anticarcinogenic, Cardioprotective, and Other Health Benefits of Tomato Compounds Lycopene, α‑Tomatine, and Tomatidine in Pure Form and in Fresh and Processed Tomatoes Mendel Friedman* Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Albany, California 94710, United States ABSTRACT: Tomatoes produce the bioactive compounds lycopene and α-tomatine that are reported to have potential health- promoting effects in animals and humans, but our understanding of the roles of these compounds in the diet is incomplete. Our current knowledge gained from the chemistry and analysis of these compounds in fresh and processed tomatoes and from studies on their bioavailability, bioactivity, and mechanisms of action against cancer cells and other beneficial bioactivities including antibiotic, anti-inflammatory, antioxidative, cardiovascular, and immunostimulating effects in cells, animals, and humans is discussed and interpreted here. Areas for future research are also suggested. The collated information and suggested research might contribute to a better understanding of the agronomical, biochemical, chemical, physiological, molecular, and cellular bases of the health-promoting effects and facilitate and guide further studies needed to optimize the use of lycopene and α-tomatine in pure form and in fresh tomatoes and processed tomato products to help prevent or treat human disease. KEYWORDS: anticarcinogenic effects, cardiovascular effects, lycopene, α-tomatine, tomatidine, fresh and processed tomatoes, chemistry, analysis, biosynthesis, bioactivity, bioavailability, mechanisms, human health, research needs ■ INTRODUCTION In addition to investigations of the beneficial properties of Tomatoes are a major source of nourishment for the world’s the tomato products described above, the use of tomato-based population.
    [Show full text]
  • The First EFSA Approved Natural Cardio-Protective Functional Ingredient
    10/07/2016 Fruitflow®: the first European Food Safety Authority­approved natural cardio­protective functional ingredient | SpringerLink Fruitflow®: the first European Food Safety Authority­approved natural cardio­ protective functional ingredient European Journal of Nutrition pp 1–22 Niamh O’Kennedy, Daniel Raederstor◘, Asim K. Duttaroy Open Access | Review First Online: 07 July 2016 DOI (Digital Object Identifier): 10.1007/s00394-016-1265-2 Cite this article as: O’Kennedy, N et al. Eur J Nutr (2016). doi:10.1007/s00394-016-1265-2 Social mentions: 10 Abstract Hyperactive platelets, in addition to their roles in thrombosis, are also important mediators of atherogenesis. Antiplatelet drugs are not suitable for use where risk of a cardiovascular event is relatively low. It is therefore important to find alternative safe antiplatelet inhibitors for the vulnerable population who has hyperactive platelets in order to reduce the risk of cardiovascular disease. Potent antiplatelet factors were identified in water­soluble tomato extract (Fruitflow®), which significantly inhibited platelet aggregation. Human volunteer studies demonstrated the potency and bioavailability of active compounds in Fruitflow®. Fruitflow® became the first product in Europe to obtain an approved, proprietary health claim under Article 13(5) of the European Health Claims Regulation 1924/2006 on nutrition and health claims made on foods. Fruitflow® is now commercially available in different countries worldwide. In addition to its reduction in platelet reactivity, Fruitflow®
    [Show full text]
  • Cytotoxic Activity of Alkaloids from the Fruits of Piper Nigrum
    See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/329269696 Cytotoxic Activity of Alkaloids from the Fruits of Piper nigrum Article in Natural product communications · November 2018 CITATIONS READS 0 85 1 author: Thao Quyen Cao Wonkwang University 16 PUBLICATIONS 21 CITATIONS SEE PROFILE All content following this page was uploaded by Thao Quyen Cao on 07 December 2018. The user has requested enhancement of the downloaded file. Volume 13. Issue 11. Pages 1419-1568. 2018 ISSN 1934-578X (printed); ISSN 1555-9475 (online) www.naturalproduct.us NPC Natural Product Communications EDITOR-IN-CHIEF HONORARY EDITOR DR. PAWAN K AGRAWAL PROFESSOR GERALD BLUNDEN Natural Product Inc. The School of Pharmacy & Biomedical Sciences, 7963, Anderson Park Lane, University of Portsmouth, Westerville, Ohio 43081, USA Portsmouth, PO1 2DT U.K. [email protected] [email protected] EDITORS ADVISORY BOARD PROFESSOR MAURIZIO BRUNO Department STEBICEF, Prof. Giovanni Appendino Prof. Niel A. Koorbanally University of Palermo, Viale delle Scienze, Novara, Italy Durban, South Africa Parco d’Orleans II - 90128 Palermo, Italy Prof. Chiaki Kuroda [email protected] Prof. Norbert Arnold Halle, Germany Tokyo, Japan PROFESSOR CARMEN MARTIN-CORDERO Department of Pharmacology, Faculty of Pharmacy, Prof. Yoshinori Asakawa Prof. Hartmut Laatsch Tokushima, Japan Gottingen, Germany University of Seville, Seville, Spain [email protected] Prof. Vassaya Bankova Prof. Marie Lacaille-Dubois PROFESSOR VLADIMIR I. KALININ Sofia, Bulgaria Dijon, France G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Prof. Roberto G. S. Berlinck Prof. Shoei-Sheng Lee Far Eastern Branch, Russian Academy of Sciences, São Carlos, Brazil Taipei, Taiwan Pr.
    [Show full text]
  • Schedule of Talks
    44th ACS Western Regional Meeting October 3-6, 2013 Hyatt Regency Santa Clara B. Charpentier and J. Gunzner-Toste, Program Chairs THURSDAY MORNING Napa I Chemistry and the Law: Where Chemistry Meets the Law The America Invents Act Sponsored by the ACS Division of Chemistry and the Law S. Thompson, Organizer, Presiding 8:30 1. An Introduction to the America Invents Act. S. Thompson 9:15 2. Practical Implications of the Leahy-Smith America Invents Act: Avoiding Prior Art Pitfalls and Other Traps for the Unwary. R. M. Thiessen 10:00 Intermission. 10:30 3. The AIA 1 Year on: the New Landscape for Challenging Patents. R. G. Bone 11:15 4. How does the new patent law impact the research of biotech scientists and managers. A. Y. Nie Camino Real Ethnobotanical Drugs Ethnobotany as Inspiration for Drug Discovery and Development Sponsored by the ACS Division of Medicinal Chemistry M. Tempesta, Organizer, Presiding 8:30 5. Traditional medicine inspired drug discovery for some modern day diseases. A. Gunatilaka 9:00 6. Scientific and regulatory challenges in the US Botanical Marketplace. J. M. Betz 9:30 7. The Discovery of SP-303 (Crofelemer/Fulyzaq), a Novel Polyphenol Isolated from Croton lechleri. M. S. Tempesta 10:00 Intermission. 10:30 8. The development of the first oral botanical drug Fulyzaq™: connecting ethnobotany, conservation, biocultural diversity, global public health and indigenous knowledge. S. R. King, P. Chaturvedi, F. C. Ayala Flores, C. G. Lozano Diaz, E. K. Tsajamen, G. C. Mashian, M. F. Pariona, E. N. Meza, E. L. Soto 11:00 9.
    [Show full text]
  • Friday Morning – Abstracts 130 - 225
    Friday morning – Abstracts 130 - 225 WRM 130 Survey of Analytical Techniques Useful for Thin Film Material Evaluation in High Technology Applications Hugh E. Gotts, [email protected] NanoAnalysis, Air Liquide Electronics, Fremont, CA 94538, United States The pervasive use of organic and inorganic materials to produce thin films in semiconductor, MEMS, Flat panel, and PV industries have challenged the sensitivity and specificity of modern analytical and physical chemical techniques. The necessity to continuously produce films of a consistent thickness, purity, and morphology requires analytical tools which are capable of measuring the required parameters quickly and accurately. As this symposium will concentrate on the application of a set of analytical methodologies, this talk will provide a guide to the techniques used. It is important to characterize the composition of organo-metallic precursors via a gas chromatographic technique (GC-MS or TC-TCD/FID). Non-volatile thermally labile materials are typically analyzed using a liquid chromatographic approach (LC-MS). Trace metal (TM) content in precursor materials are accurately determined using a variety of Inductively Coupled Plasma- Mass Spectroscopy (ICP-MS) techniques. Once the thin film has been produced, TM measurements are performed utilizing LA-ICP-MS, dynamic SIMS or TOF-SIMS. Morphology is determined utilizing AFM, SEM or TEM techniques. Other techniques will be discussed as appropriate. WRM 131 Characterization of Precursors used in Semiconductor Manufacturing using a diverse set of Analytical Techniques Conor Mckenna, [email protected], Vani Thirumala. Fab Materials Operations, Intel Corp., Santa Clara, CA 95054, United States The demands of cutting edge semiconductor manufacturing process technology require an ever- expanding range of materials to enable continued innovation for both processor performance and efficiency.
    [Show full text]
  • New Solanocapsine-Type Tomato Glycoside from Ripe Fruit of Solanum Lycopersicum
    November 2011 Note Chem. Pharm. Bull. 59(11) 1403—1405 (2011) 1403 New Solanocapsine-Type Tomato Glycoside from Ripe Fruit of Solanum lycopersicum a b ,a Mizuho OHNO, Masateru ONO, and Toshihiro NOHARA* a Faculty of Pharmaceutical Sciences, Sojo University; 4–22–1 Ikeda, Kumamoto 860–0082, Japan: and b School of Agriculture, Tokai University; 5435 Aso, Kumamoto 869–1404, Japan. Received May 26, 2011; accepted August 18, 2011; published online August 23, 2011 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-16b,23-epoxy-3b,23,24-trihydroxycholestane 3-O-b-lycotetraoside. Key words tomato fruit; Solanum lycopersicum; solanocapsine-type glycoside; tomato glycoside For metabolic analysis of steroidal glycosides,1) we se- local Italian tomatoes, processed tomato products, and im- lected the tomato as part of our systematic investigation of ported canned tomatoes, tomato juice, and ketchup is cur- the constituents of Solanum plants.2) We recognized that the rently in progress. tomato would be appropriate because we were convinced that Esculeoside B-1 (2) is the first example of a solanocap- it had steroidal glycosides, as its aerial parts and immature sine-type steroidal alkaloid glycoside, the fundamental skele- fruits are rich sources of tomatine. Hence, we isolated ton of which is very rare and interesting in terms of its chem- steroidal glycosides from the ripe fruit. In Japanese tomatoes, ical structure and unknown pharmacological activity.
    [Show full text]
  • Reduction in Hypercholesterolemia and Risk Of
    GRASAS Y ACEITES, 61 (4), OCTUBRE-DICIEMBRE, 378-389, 2010, ISSN: 0017-3495 DOi:10.3989/gya.021210 Reduction in hypercholesterolemia and risk of cardiovascular diseases by mixtures of plant food extracts: a study on plasma lipid profile, oxidative stress and testosterone in rats By Doha A. Mohamed, Thanaa E. Hamed and Sahar Y. Al-Okbi * Food Sciences and Nutrition Department, National Research Centre, Dokki, Cairo, Egypt (*Corresponding author: S_Y_alokbi@ hotmail.com) RESUMEN cias mostraron una mejora del perfil lipídico del plasma, un significativo incremento en la testosterona, y un descenso Reducción de las enfermedades cardiovasculares e del estrés oxidativo con una prometedora prevención de las hipercolesterolemia por mezclas de extractos de plan- enfermedades cardiovasculares y ateroesclerosis. El efecto tas comestibles: un estudio del perfil lipídico, estrés anti-aterogénico de las mezclas de los extractos puede ser oxidativo y testosterona en ratas. debida a la presencia de compuestos fenólicos, fitoesteroles, tocoferoles y ácidos grasos insaturados. El presente estudio fue dirigido a preparar y evaluar ia in- fluencia de dos mezclas de extractos de plantas comestibles PALABRAS CLAVE: Estrés oxidativo - Hipereolesterole- sobre ei perfil lipídico del plasma, estrés oxidativo y nivel de mia - Mezclas de extraetos - Perfil lipfdieo - Testosterona. testosterona en ratas alimentadas con una dieta hipercoieste- rolemica. La salubridad de las mezclas de extractos estudia- das fue evaluada mediante la determinación de las funciones Summary del hígado y dei riñon. El contenido totai de fenoles, tocofero- les, ácidos grasos, y materia insaponificable (UNSAP) fueron Reduction in hypercholesterolemia and risk of determinado en la mezclas de extractos. Las ratas fueron ali- cardiovascular diseases by mixtures of plant food extract: mentadas con dietas hipercoiesterolémica junto con una do- a study on plasma lipid profile, oxidative stress and sis oral diaria de (300 mg/kg de peso) cada mezcla I y II du- testosterone in rats.
    [Show full text]
  • A Longterm Comparison of the Influence of Organic And
    Research Article Received: 3 August 2012 Revised: 25 September 2012 Accepted article published: 15 October 2012 Published online in Wiley Online Library: 9 November 2012 (wileyonlinelibrary.com) DOI 10.1002/jsfa.5951 A long-term comparison of the influence of organic and conventional crop management practices on the content of the glycoalkaloid α-tomatine in tomatoes Eunmi Koh,a Stephen Kaffkab and Alyson E Mitchella∗ Abstract BACKGROUND: α-Tomatine, synthesized by Lycopersicon and some Solanum species, is a steroidal glycoalkaloid which functions to protect against pathogens and insects. Although glycoalkaloids are generally considered toxic, α-tomatine appears to be well tolerated in humans. α-Tomatine has numerous potential health benefits including the ability to inhibit cancer cell growth in in vitro studies. α-Tomatine is influenced by numerous agronomic factors including fertilization and nitrogen availability. Herein, the levels of α-tomatine were compared in dried tomato samples (Lycopersicon esculentum L. cv. Halley 3155) produced in organic and conventional cropping systems that had been archived over the period from 1994 to 2004 from the Long Term Research on Agricultural Systems project (LTRAS) at UC Davis. RESULTS: The α-tomatine levels of tomatoes in both cropping systems ranged from 4.29 to 111.85 µgg−1 dry weight. Mean levels of α-tomatine were significantly higher in the organically grown tomatoes than conventional ones (P < 0.001). In the organic management system, α-tomatine content was also significantly (P < 0.001) different between cropping years, suggesting that other influencing factors such as environmental conditions also affect α-tomatine content in tomato. CONCLUSIONS: The organically produced tomatoes had higher average α-tomatine content than their conventional counterpart over the 10-year study.
    [Show full text]
  • Spatially Resolved Metabolic Distribution for Unraveling The
    Anal Bioanal Chem DOI 10.1007/s00216-016-0118-4 RESEARCH PAPER Spatially resolved metabolic distribution for unraveling the physiological change and responses in tomato fruit using matrix-assisted laser desorption/ionization–mass spectrometry imaging (MALDI–MSI) Junya Nakamura1 & Tomomi Morikawa-Ichinose2 & Yoshinori Fujimura2 & Eisuke Hayakawa3 & Katsutoshi Takahashi4 & Takanori Ishii2 & Daisuke Miura2 & Hiroyuki Wariishi1,2,5,6 Received: 28 October 2016 /Revised: 21 November 2016 /Accepted: 24 November 2016 # The Author(s) 2016. This article is published with open access at Springerlink.com Abstract Information on spatiotemporal metabolic behavior more than 30 metabolite-derived ions, including primary and is indispensable for a precise understanding of physiological secondary metabolites, simultaneously. To investigate spatio- changes and responses, including those of ripening processes temporal metabolic alterations during physiological changes and wounding stress, in fruit, but such information is still at the whole-tissue level, MALDI–MSI was performed using limited. Here, we visualized the spatial distribution of metab- the different ripening phenotypes of mature green and mature olites within tissue sections of tomato (Solanum lycopersicum red tomato fruits. Although apparent alterations in the locali- L.) fruit using a matrix-assisted laser desorption/ionization– zation and intensity of many detected metabolites were not mass spectrometry imaging (MALDI–MSI) technique com- observed between the two tomatoes, the amounts of glutamate bined with a matrix sublimation/recrystallization method. and adenosine monophosphate, umami compounds, increased This technique elucidated the unique distribution patterns of in both mesocarp and locule regions during the ripening pro- cess. In contrast, malate, a sour compound, decreased in both regions. MALDI–MSI was also applied to evaluate more local Electronic supplementary material The online version of this article (doi:10.1007/s00216-016-0118-4) contains supplementary material, metabolic responses to wounding stress.
    [Show full text]