Dehydrotomatine and α-Tomatine Content in Tomato Fruits and Vegetative Plant Tissues

Kozukue, Nobuyuki; Han, Jae-Sook; Lee, Kap-Rang; Friedman, Mendel

doi:10.1021/jf0306845

Cited by 117 publications

(109 citation statements)

References 29 publications

(38 reference statements)

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“…They suggested that the low oral toxicity of tomatine might be due to its ability of forming an insoluble complex with cholesterol in vivo which can then be eliminated through feces. Kozukue et al (2004) have suggested that biosynthesis/degradation of dehydrotomatine and -tomatine may be under distinct genetic control in the leaves of tomato plants. In this study, the contents of tomatine and tomatidine in the 50 tomato accessions were measured (Table 1).…”

Section: Discussionmentioning

confidence: 99%

Chemical Constitutions and Antioxidant Activities of Tomato Leaf Extracts

Lee¹,

Lee²,

Ma³

et al. 2016

Plant Breed. Biotech.

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This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/4.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. ABSTRACT The present study aimed to determine the contents of five flavonols and two glycoalkaloids as well as the antioxidant activities of leaf ethanol extracts of 50 tomato accessions. The antioxidant activity was assessed using different tests: 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), 2,2-diphenyl-1-picryl hydrazyl (DPPH), nitric oxide (NO), and total polyphenol content (TPC). Flavonols and glycoalkaloids contents were determined using a high performance liquid chromatography-diode array detector system. Among five flavonols and two glycoalkaloids, naringenin and tomatine were detected in tomato leaves at high concentrations. Of the 50 tomato accessions, IT 229711, IT2365203, and IT 207224 were found to have the highest contents of quercetin, kaempferol, and tomatine, respectively. Leaf extract of IT189949 exhibited the highest relative antioxidant capacity index (RACI). Among the five flavonols, myricetin showed positive correlations with DPPH, ABTS, and NO, while isorhamnetin had positive correlation with DPPH. These results will expand the chemical constitution database and provide information on tomato leaves. They are valuable for the development of functional foods or feed-additives.

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Section: Discussionmentioning

confidence: 99%

Chemical Constitutions and Antioxidant Activities of Tomato Leaf Extracts

Lee¹,

Lee²,

Ma³

et al. 2016

Plant Breed. Biotech.

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“…UDP-Gal was readily used as a donor, producing a novel product with a mass-to-charge ratio of 578 m/z ([M+H]), corresponding to galactosylated tomatidine (Figure 3). Dehydrotomatidine (414 m/z; Figure 3), identified in the tomatidine standard as a contaminant (Kozukue et al, 2004), was also galactosylated by GAME1 (product 576 m/z). UDP-Glc was also incorporated to some extent, however, not exceeding 5% of the Gal incorporation under identical concentrations and conditions.…”

Section: Functional Characterization Of the Game1 Recombinant Enzyme mentioning

confidence: 99%

“…A proposed pathway that represents the biosynthesis and metabolism of SAs during tomato fruit development (from the immature green to the RR stage) was generated based on previously published data (Friedman, 2002;Kozukue et al, 2004;Moco et al, 2007;Iijima et al, 2008Iijima et al, , 2009Mintz-Oron et al, 2008) and the data from this study ( Figure 6). …”

Section: Mg Fruit Of Game1i Plants Display Altered Levels Of Sasmentioning

confidence: 99%

“…The major SA in tomato, a-tomatine, was reported to be present in the green tissues of the plant together with dehydrotomatine (Kozukue et al, 2004). Whereas a-tomatine levels decrease as the fruit matures and ripens, recent studies suggest a ripening-dependent conversion of a-tomatine into esculeoside A, the most abundant SA in the red-ripe (RR) tomato fruit (Fujiwara et al, 2004;Moco et al, 2007;Iijima et al, 2008;Mintz-Oron et al, 2008;Yamanaka et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

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GLYCOALKALOID METABOLISM1 Is Required for Steroidal Alkaloid Glycosylation and Prevention of Phytotoxicity in Tomato

et al. 2011

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Steroidal alkaloids (SAs) are triterpene-derived specialized metabolites found in members of the Solanaceae family that provide plants with a chemical barrier against a broad range of pathogens. Their biosynthesis involves the action of glycosyltransferases to form steroidal glycoalkaloids (SGAs). To elucidate the metabolism of SGAs in the Solanaceae family, we examined the tomato (Solanum lycopersicum) GLYCOALKALOID METABOLISM1 (GAME1) gene. Our findings imply that GAME1 is a galactosyltransferase, largely performing glycosylation of the aglycone tomatidine, resulting in SGA production in green tissues. Downregulation of GAME1 resulted in an almost 50% reduction in a-tomatine levels (the major SGA in tomato) and a large increase in its precursors (i.e., tomatidenol and tomatidine). Surprisingly, GAME1-silenced plants displayed growth retardation and severe morphological phenotypes that we suggest occur as a result of altered membrane sterol levels caused by the accumulation of the aglycone tomatidine. Together, these findings highlight the role of GAME1 in the glycosylation of SAs and in reducing the toxicity of SA metabolites to the plant cell.

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“…The knowledge on the role of glycoalkaloids in pollen is scarce, but the different levels of glycoalkaloids observed in different stages of pollen development might be important to ensure an optimal defense against biotic attacks during plant reproduction. This idea would agree with the finding that the concentration of α-tomatin has been reported to be 2-fold higher in flowers than in leaves of tomato plants ( Kozukue et al 2004). …”

Section: Alkaloidssupporting

confidence: 91%

Identification of metabolites involved in heat stress response in different tomato genotypes

Paupière¹

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Propositions1. Since tomato pollen is sensitive to temperature variations, results from climate chamber experiments with controlled temperature cannot be extrapolated to pollen thermotolerance in commercial tomato production.(this thesis)2. The pollen isolation protocol is a critical determinant for the success of pollen metabolomics studies.(this thesis)3. The choice of the p-value has an undesirably strong influence on a study's conclusions.4. Nutrition should be considered as the first medicine. MeatlessMonday is an effective policy to reduce global warming.6. The health of science rests on scientist's honesty. If Dutch were not Dutch but French, most of them would not speak EnglishPropositions belonging to the thesis, entitled Contents ___________________________________________________________________________ Chapter 1General introduction 1 Chapter 2The metabolic basis of pollen thermo-tolerance: Perspectives for breeding 13 Chapter 3The effect of isolation methods of tomato pollen on the results of metabolic profiling 39 Chapter 4Untargeted metabolomic analysis of tomato pollen development and heat stress response 63 Chapter 5Screening for pollen tolerance to high temperatures in tomato 83 Chapter 6Metabolites associated with thermo-tolerance of tomato pollen 95 Chapter 7General discussion 133 References Climate changeClimate is unequivocally changing. In 2014, IPCC released the fifth assessment report on climate change and stated that "the atmosphere and ocean have warmed, the amounts of snow and ice have diminished and sea level has risen" (IPCC 2014). The main cause for this global warming is extremely likely to be due to anthropogenic activities that are widely acknowledged by climate specialists (Cook et al. 2013). Heat waves and extreme temperatures are expected to be more frequent and to last longer (Meehl and Tebaldi 2004). This climate change is expected to affect the world of today in many ways, including the extinction of species that cannot escape their environment and a decrease in food productivity. For instance, the well documented heat wave of 2003 in Europe led to a yield loss of 25% and 21% for maize and wheat in France, respectively, with an overall economic loss in the European Union estimated at 13 billion euros (IPCC 2007). The direct effect on the human population is not to be underestimated, especially if one takes into account that the world population is predicted to rise from 7.3 billion up to 11 billion by the middle of the 21 st century, thus alarming the decision-makers (Porter and Semenov 2005). From the reduction of greenhouse gas emission with the Kyoto protocol (Oberthur and Hermann 1999) to the recent COP21 agreement to limit the temperature increase of 2˚C (Iyer et al. 2015), policymakers mull over mitigation options. A synergy of policies and adaptation strategies may enhance the efficacy to respond to climate change and limit the consequences on living organisms and ecosystems. The adaption of crops is nested in the identification of genotypes tolerant to temperature...

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Dehydrotomatine and α-Tomatine Content in Tomato Fruits and Vegetative Plant Tissues

Cited by 117 publications

References 29 publications

Chemical Constitutions and Antioxidant Activities of Tomato Leaf Extracts

Chemical Constitutions and Antioxidant Activities of Tomato Leaf Extracts

GLYCOALKALOID METABOLISM1 Is Required for Steroidal Alkaloid Glycosylation and Prevention of Phytotoxicity in Tomato

Identification of metabolites involved in heat stress response in different tomato genotypes

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