Rapid high-performance liquid chromatographic method for the quantification of .alpha.-tomatine in tomato

Keukens, E.A.J.; Hop, Margareth E. C. M.; Jongen, W.M.F.

doi:10.1021/jf00047a020

Cited by 20 publications

(12 citation statements)

References 9 publications

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“…Previous chromatography-based methods to quantify both potato and tSGAs relied on photodiode array detectors and set 208 nm (Del Giudice et al, 2015; Kozukue et al, 2004; Kozukue and Friedman, 2003; Tajner-Czopek et al, 2014). Given that the molar extinction coefficient for alpha-tomatine is only 5000 M -1 c -1 , (Keukens et al, 1994), photodiode array detectors are not sensitive enough for detecting low quantities of these compounds, nor distinguishing between different alkaloids. Moreover, photodiode array detectors are often set to 200 nm to quantify tSGAs which is a non-specific wavelength where many compounds (including mobile phases) can absorb light (Friedman and Levin, 1998, 1992; Keukens et al, 1994).…”

Section: Resultsmentioning

confidence: 99%

“…Given that the molar extinction coefficient for alpha-tomatine is only 5000 M -1 c -1 , (Keukens et al, 1994), photodiode array detectors are not sensitive enough for detecting low quantities of these compounds, nor distinguishing between different alkaloids. Moreover, photodiode array detectors are often set to 200 nm to quantify tSGAs which is a non-specific wavelength where many compounds (including mobile phases) can absorb light (Friedman and Levin, 1998, 1992; Keukens et al, 1994). Mass spectrometers offer substantial gains in sensitivity through the use of MRM experiments and the ability to differentiate numerous analytes in a single run.…”

Section: Resultsmentioning

confidence: 99%

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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: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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

Dzakovich

Hartman

Cooperstone

2019

Preprint

View full text Add to dashboard Cite

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“…The disadvantages of GC determination include that the SGAs must be hydrolyzed to the corresponding alkaloids and the multistep procedure may not always be quantitative. Also, a-tomatine present in tomato and certain wild potato species may not be readily detected by the methodology developed for potato SGAs (Deahl et al, 1993;Bushway et al, 1994;Friedman et al, 1994;Keukens et al, 1994). Structural analysis of SGAs has been advanced significantly through the application of modem methods of mass spectrometry (Chen et al, 1994).…”

Section: Discussionmentioning

confidence: 99%

Potato Glycoalkaloids: A Burden or a Blessing?

Valkonen

Keskitalo²,

Vasara

et al. 1996

Critical Reviews in Plant Sciences

110

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Steroidal glycoalkaloids (SGAs) are produced following the general steroid biosynthesis pathway, starting from acetyl-coenzyme A and followed by the intermediates mevalonic acid, squalene, cycloartenol, and cholesterol. a-Chaconine and a-solanine are the main SGAs of the cultivated potato (Solanurn tuberosum), whereas many other SGAs are known in the wild potato species. Low concentrations of SGAs improve the taste of potato, but concentrations greater than 200 mgkg can have toxic effects on animals and humans. SGAs have antimicrobial activity and confer resistance to some insects, but many such pests of potato are not greatly affected. Certain environmental conditions and wounding enhance SGA accumulation in tubers in the field and storage. Low production of SGAs is a dominant character inherited in a relatively simple manner and can be selected for in potato-breeding programs, whereas the use of wild potato germplasm tends to increase the SGA accumulation in the breeding lines. Further efforts are likely to be directed toward the reduction of the SGA content in the edible potato products through breeding and biotechnological methodologies, whereas potato genotypes with high SGA production may be developed for use in the pharmaceutical industry.

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“…Elution was at 1.0 mL/min with a step gradient from 100% Buffer A (20 m M KH 2 PO 4 pH 5.0) to 100% Buffer B (20 m M KH 2 PO 4 pH 5.0: acetonitrile, 25:75, v/v) as described by Keukens et al (1994) The column was maintained at room temperature, and the injection volume was 25 μL. Detection of peaks was monitored at 220 nm.…”

Section: Methodsmentioning

confidence: 99%

Evaluating Maize for Allelochemicals That Affect European Corn Borer (Lepidoptera: Crambidae) Larval Development

et al. 2001

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or tight husk cover, and biochemical components are thought to be involved (Grier and Davis, 1980; Joyce European corn borer (ECB), Ostrinia nubilalis (Hü bner), larvae and Davis, 1995;Warnock et al., 1997), but the compodevelop resistance to management protocols in laboratory and field environments. Laboratory bioassays, tissue elemental analyses, and nents are not easily separated in field studies. Laborafield resistance evaluations were conducted on ear tissues of maize, tory bioassays, without the confounding effects of bio-Zea mays L., to (i) identify genotypes and tissues which affect ECB physical components, may facilitate the detection of development, (ii) isolate tissue extracts detrimentally affecting larvae, allelochemicals in sweet corn tissues affecting ECB lar-(iii) determine if high performance liquid chromatography (HPLC) val development (Warnock et al., 1997). absorption peaks are associated with biological activity, (iv) determine Three types of compounds occurring in corn tissues if ferulic acid and p-coumaric acid affect ECB larvae, and (v) deterhave been shown to affect insects detrimentally in labomine if laboratory and field resistance are related. Tissue and genotype ratory bioassays: caffeic acid derivatives, flavonoid glydid not affect larval survival. Silk tissue from W182E, 'Apache', MN cosides, and the hydroxamic acid family typified by 3153, and MN 276 reduced 10-d larval weight, increased time to puchlorogenic acid, maysin, and DIMBOA (2,4-dihydroxypation, reduced pupal weight, and increased time to moth emergence compared with kernel tissue, which did not differ from the cellulose ison,

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Rapid high-performance liquid chromatographic method for the quantification of .alpha.-tomatine in tomato

Cited by 20 publications

References 9 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

Potato Glycoalkaloids: A Burden or a Blessing?

Evaluating Maize for Allelochemicals That Affect European Corn Borer (Lepidoptera: Crambidae) Larval Development

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