Saponins, Esculeosides B-1 and B-2, in Tomato Juice and Sapogenol, Esculeogenin B&lt;sub&gt;1&lt;/sub&gt;

Nohara, Toshihiro; Fujiwara, Yukio; Zhou, Jian-Rong; Urata, Jun; Ikeda, Tsuyoshi; Murakami, Kōtarō; El‐Aasr, Mona; Ono, M.

doi:10.1248/cpb.c15-00449

Cited by 16 publications

(20 citation statements)

References 10 publications

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“…2). In the case of esculeoside B, multiple diastereomers have been previously reported in tomato products which explains our observation of multiple peaks for this analyte (Hövelmann et al, 2019; Manabe et al, 2013; Nohara et al, 2015). Validation experiments, including confirmation of peak identities using high-resolution mass spectrometry, were next carried out using the finalized chromatographic gradient.…”

Section: Resultssupporting

confidence: 80%

A High-Throughput Extraction and Analysis Method for Steroidal Glycoalkaloids in Tomato

Dzakovich

Hartman

Cooperstone

2019

Preprint

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19Tomato steroidal glycoalkaloids (tSGAs) are a class of cholesterol-derived metabolites uniquely 20 produced by the tomato clade. These compounds provide protection against biotic stress due to 21 their fungicidal and insecticidal properties. Although commonly reported as being anti-nutritional, 22 both in vitro as well as pre-clinical animal studies have indicated that some tSGAs may have a 23 beneficial impact on human health. However, the paucity of quantitative extraction and analysis 24 methods presents a major obstacle for determining the biological and nutritional functions of 25 tSGAs. To address this problem, we developed and validated the first comprehensive extraction 26 and UHPLC-MS/MS quantification method for tSGAs. Our extraction method allows for up to 16 27 samples to be extracted simultaneously in 20 minutes with 93.0 ± 6.8% and 100.8 ± 13.1% 28 recovery rates for tomatidine and alpha-tomatine, respectively. Our ultra-high-performance liquid 29 chromatography tandem mass spectrometry (UHPLC-MS/MS) method was able to 30 chromatographically separate analytes derived from 16 tSGAs representing 9 different tSGA 31 masses, as well as two internal standards, in 13 minutes. Tomato steroidal glycoalkaloids that did 32 not have available standards were annotated using high resolution mass spectrometry as well as 33 product ion scans that provided fragmentation data. Lastly, we utilized our method to survey a 34 variety of commonly consumed tomato-based products. Total tSGA concentrations ranged from 35 0.7 to 3.4 mg/serving and represent some of the first reported tSGA concentrations in tomato-36 based products. Our validation studies indicate that our method is sensitive, robust, and able to be 37 used for a variety of applications where concentrations of biologically relevant tSGAs need to be 38 quantified. 39 40 Introduction 41Solanaceous plants produce a spectrum of cholesterol derived compounds called steroidal 42 glycoalkaloids. While each solanaceous clade produces its own unique assortment of steroidal 43 glycoalkaloids, these metabolites share commonality in their role as phytoanticipins and anti-44 herbivory agents (Etalo et al., 2015; Fontaine et al., 1948; Irving et al., 1945; Ökmen et al., 2013). 45Tomato (Solanum lycopersicum and close relatives) is no exception, and over 100 tomato steroidal 46 glycoalkaloids (tSGAs, Fig. 1) have been suggested (Iijima et al., 2013(Iijima et al., , 2008. Although these 47 compounds are typically reported as anti-nutritional (Ballester et al., 2016; Cárdenas et al., 2016 Cárdenas et al., , 48 2015 Itkin et al., 2013), other studies suggest a health-promoting role. In fact, emerging evidence 49 suggests that some tSGAs may play a role in positive health outcomes associated with tomato 50 consumption (Cayen, 1971; Choi et al., 2012; Cooperstone et al., 2017; Lee et al., 2004). While 51 these compounds continue to be evaluated both in planta and in vivo, there is a lack of quantitative 52 and validated methods to extract and measure tSGAs from tomato...

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Section: Resultssupporting

confidence: 80%

A High-Throughput Extraction and Analysis Method for Steroidal Glycoalkaloids in Tomato

Dzakovich

Hartman

Cooperstone

2019

Preprint

View full text Add to dashboard Cite

show abstract

“…We observed multiple peaks for many of our masses indicating the presence of multiple isobaric tSGAs (likely including structural isomers) (Figure 2). In the case of esculeoside B, multiple diastereomers have been previously reported in tomato products which explains our observation of multiple peaks for this analyte (Manabe et al, 2013;Nohara et al, 2015;Hövelmann et al, 2019). Validation experiments, including confirmation of peak identities using high-resolution mass spectrometry, were next carried out using the finalized chromatographic gradient.…”

Section: Development Of Chromatographic Gradientmentioning

confidence: 69%

A High-Throughput Extraction and Analysis Method for Steroidal Glycoalkaloids in Tomato

2020

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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 this problem, we developed and validated the first comprehensive extraction and ultra-high-performance liquid chromatography tandem mass spectrometry (UHPLC-MS/MS) quantification method for tSGAs. Our extraction method allows for up to 16 samples to be extracted simultaneously in 20 min with 93.0 ± 6.8 and 100.8 ± 13.1% recovery rates for tomatidine and alpha-tomatine, respectively. Our UHPLC-MS/MS method was able to chromatographically separate analytes derived from 18 tSGA peaks representing 9 different tSGA masses, as well as two internal standards, in 13 min. Tomato steroidal glycoalkaloids that did not have available standards were annotated using high resolution mass spectrometry as well as product ion scans that provided fragmentation data. Lastly, we utilized our method to survey a variety of commonly consumed tomato-based products. Total tSGA concentrations ranged from 0.2 to 3.4 mg/serving and represent some of the first reported tSGA concentrations in tomatobased products. Our validation studies indicate that our method is sensitive, robust, and able to be used for a variety of applications where concentrations of biologically relevant tSGAs need to be quantified.

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“…Specificity of these biomarkers can be considered given as well, since esculeogenin B sulfonate and the hydroxy-esculeogenin B isomers were just detectable in traces, or not at all, in most of the blank urine samples provided after 3 days of avoiding any tomato-based foods. Furthermore, the occurrence of the corresponding metabolic precursors esculeoside B-1 and B-2 has only been reported in tomato juice, [26] canned tomatoes, [27] and ripe tomato fruits [23] so far. The latter implies that these metabolites are potentially applicable as urinary biomarkers for the intake of fresh tomato products as well.…”

Section: Urinary Excretion Of Steroidal Alkaloids After Tomato Juice Intakementioning

confidence: 99%

Mass Spectrometry–Based Analysis of Urinary Biomarkers for Dietary Tomato Intake

Hövelmann

Lewin

Steinert

et al. 2020

Molecular Nutrition Food Res

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In this study, the applicability of several -carboline, imidazole, and steroidal alkaloids as biomarkers for tomato juice intake is evaluated. Methods and results: Over the course of a 2-week crossover dietary intervention study, 14 volunteers were given low and high doses of tomato juice after 3 days of avoiding tomato-based products. On the day of consumption and the following days, volunteers provided urine samples that were quantitatively analyzed by high-performance liquid chromatography-tandem mass spectrometry. Herein, glucose-derived -carboline alkaloids are determined as supporting, yet non-specific dietary biomarkers for tomato juice intake. Several imidazole alkaloids represent further biomarkers, which are shown to specifically indicate consumption of tomato juice for 24 h and partly >24 h. Additionally, steroidal alkaloids derived from esculeogenin B are determined to be specific biomarkers for tomato juice detectable for at least 48 h after consumption. The intake of low and high amounts of tomato juice is significantly distinguishable based on the urinary excretion of all determined biomarkers as well. Conclusions: The dietary intake of tomato juice is conclusively traceable based on urinary excretion of multiple -carboline, imidazole, and steroidal alkaloids, and can be determined for up to 48 h after consumption. Furthermore, different intake doses can clearly be distinguished based on their urinary excretion.

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

Cited by 16 publications

References 10 publications

A High-Throughput Extraction and Analysis Method for Steroidal Glycoalkaloids in Tomato

A High-Throughput Extraction and Analysis Method for Steroidal Glycoalkaloids in Tomato

A High-Throughput Extraction and Analysis Method for Steroidal Glycoalkaloids in Tomato

Mass Spectrometry–Based Analysis of Urinary Biomarkers for Dietary Tomato Intake

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