TY - JOUR A1 - Hoffmann, Holger A1 - Ott, Christiane A1 - Raupbach, Jana A1 - Andernach, Lars A1 - Renz, Matthias A1 - Grune, Tilman A1 - Hanschen, Franziska S. T1 - Assessing bioavailability and bioactivity of 4-Hydroxythiazolidine-2-Thiones, newly discovered glucosinolate degradation products formed during domestic boiling of cabbage JF - Frontiers in nutrition N2 - Glucosinolates are plant secondary metabolites found in cruciferous vegetables (Brassicaceae) that are valued for their potential health benefits. Frequently consumed representatives of these vegetables, for example, are white or red cabbage, which are typically boiled before consumption. Recently, 3-alk(en)yl-4-hydroxythiazolidine-2-thiones were identified as a class of thermal glucosinolate degradation products that are formed during the boiling of cabbage. Since these newly discovered compounds are frequently consumed, this raises questions about their potential uptake and their possible bioactive functions. Therefore, 3-allyl-4-hydroxythiazolidine-2-thione (allyl HTT) and 4-hydroxy-3-(4-(methylsulfinyl) butyl)thiazolidine-2-thione (4-MSOB HTT) as degradation products of the respective glucosinolates sinigrin and glucoraphanin were investigated. After consumption of boiled red cabbage broth, recoveries of consumed amounts of the degradation products in urine collected for 24 h were 18 +/- 5% for allyl HTT and 21 +/- 4% for 4-MSOB HTT (mean +/- SD, n = 3). To investigate the stability of the degradation products during uptake and to elucidate the uptake mechanism, both an in vitro stomach and an in vitro intestinal model were applied. The results indicate that the uptake of allyl HTT and 4-MSOB HTT occurs by passive diffusion. Both compounds show no acute cell toxicity, no antioxidant potential, and no change in NAD(P)H dehydrogenase quinone 1 (NQO1) activity up to 100 mu M. However, inhibition of glycogen synthase kinases-3 (GSK-3) in the range of 20% for allyl HTT for the isoform GSK-3 beta and 29% for 4-MSOB HTT for the isoform GSK-3 alpha at a concentration of 100 mu M was found. Neither health-promoting nor toxic effects of 3-alk(en)yl-4-hydroxythiazolidine-2-thiones were found in the four tested assays carried out in this study, which contrasts with the properties of other glucosinolate degradation products, such as isothiocyanates. KW - stomach model KW - glycogen synthase kinase-3 KW - cytotoxicity KW - antioxidant potential KW - intestinal model KW - cellular uptake KW - isothiocyanate Y1 - 2022 U6 - https://doi.org/10.3389/fnut.2022.941286 SN - 2296-861X VL - 9 PB - Frontiers Media CY - Lausanne ER - TY - JOUR A1 - Witzel, Katja A1 - Abu Risha, Marua A1 - Albers, Philip A1 - Börnke, Frederik A1 - Hanschen, Franziska S. T1 - Corrigendum : Identification and characterization of three epithiospecifier protein isoforms in Brassica oleracea / Witzel, Katja; Abu Risha, Marua; Albers, Philip; Börnke, Frederike; Hanschen, Franziska S. - Lausanne: Frontiers Media, 2019. - Frontiers in plant science : FPLS. - 10 (2019) art. 1552. - doi: 10.3389/fpls.2019.01552 JF - Frontiers in plant science : FPLS KW - epithionitrile KW - expression profile KW - functional complementation KW - glucosinolate hydrolysis KW - nitrile KW - specifier proteins KW - tissue KW - specificity Y1 - 2020 U6 - https://doi.org/10.3389/fpls.2020.00523 SN - 1664-462X VL - 11 PB - Frontiers Media CY - Lausanne ER - TY - JOUR A1 - Heinze, Mandy A1 - Hanschen, Franziska S. A1 - Wiesner-Reinhold, Melanie A1 - Baldermann, Susanne A1 - Gräfe, Jan A1 - Schreiner, Monika A1 - Neugart, Susanne T1 - Effects of Developmental Stages and Reduced UVB and Low UV Conditions on Plant Secondary Metabolite Profiles in Pak Choi (Brassica rapa subsp chinensis) JF - Journal of agricultural and food chemistry : a publication of the American Chemical Society N2 - Pak choi (Brassica rapa subsp. chinensis) is rich in secondary metabolites and contains numerous antioxidants, including flavonoids; hydroxycinnamic acids; carotenoids; chlorophylls; and glucosinolates, which can be hydrolyzed to epithionitriles, nitriles, or isothiocyanates. Here, we investigate the effect of reduced exposure to ultraviolet B (UVB) and UV (UVA and UVB) light at four different developmental stages of pak choi. We found that both the plant morphology and secondary metabolite profiles were affected by reduced exposure to UVB and UV, depending on the plant’s developmental stage. In detail, mature 15- and 30-leaf plants had higher concentrations of flavonoids, hydroxycinnamic acids, carotenoids, and chlorophylls, whereas sprouts contained high concentrations of glucosinolates and their hydrolysis products. Dry weights and leaf areas increased as a result of reduced UVB and low UV. For the flavonoids and hydroxycinnamic acids in 30-leaf plants, less complex compounds were favored, for example, sinapic acid acylated kaempferol triglycoside instead of the corresponding tetraglycoside. Moreover, also in 30-leaf plants, zeaxanthin, a carotenoid linked to protection during photosynthesis, was increased under low UV conditions. Interestingly, most glucosinolates were not affected by reduced UVB and low UV conditions. However, this study underlines the importance of 4-(methylsulfinyl)butyl glucosinolate in response to UVA and UVB exposure. Further, reduced UVB and low UV conditions resulted in higher concentrations of glucosinolate-derived nitriles. In conclusion, exposure to low doses of UVB and UV from the early to late developmental stages did not result in overall lower concentrations of plant secondary metabolites. KW - flavonoids KW - hydroxycinnamic acids KW - carotenoids KW - glucosinolates KW - nitriles KW - UVB reduction Y1 - 2018 U6 - https://doi.org/10.1021/acs.jafc.7b03996 SN - 0021-8561 SN - 1520-5118 VL - 66 IS - 7 SP - 1678 EP - 1692 PB - American Chemical Society CY - Washington ER - TY - JOUR A1 - Chen, Xiaomin A1 - Hanschen, Franziska S. A1 - Neugart, Susanne A1 - Schreiner, Monika A1 - Vargas, Sara A. A1 - Gutschmann, Björn A1 - Baldermann, Susanne T1 - Boiling and steaming induced changes in secondary metabolites in three different cultivars of pak choi (Brassica rapa subsp. chinensis) JF - Journal of Food Composition and Analysis N2 - Pak choi (Brassica rapa subsp. chinensis) is a leafy vegetable that is widely available in Asia and consumed in rising quantities in Europe. Pak choi contains high levels of secondary plant metabolites, such as carotenoids, chlorophylls, glucosinolates, phenolic compounds, and vitamin K, which are beneficial for humans if consumed on a regular basis. The evaluation of the genotype-induced variation of secondary plant metabolites revealed that the cultivar ‘Amur’ contained the highest concentration of secondary plant metabolites. Furthermore, steaming retained more chlorophylls, glucosinolates, phenolic acids and flavonoid compounds than boiling. In contrast, both domestic cooking methods – boiling, and steaming – reduced the formation of glucosinolate breakdown products, especially the undesired epithionitriles and nitriles but less of the health-beneficial isothiocyanates. KW - Pak choi KW - Secondary metabolites KW - Glucosinolates KW - Carotenoids KW - Chlorophylls KW - Flavonoids KW - Vitamin K KW - Domestic cooking Y1 - 2019 U6 - https://doi.org/10.1016/j.jfca.2019.06.004 SN - 0889-1575 SN - 1096-0481 VL - 82 PB - Elsevier CY - San Diego ER - TY - JOUR A1 - Klopsch, Rebecca A1 - Baldermann, Susanne A1 - Hanschen, Franziska S. A1 - Voss, Alexander A1 - Rohn, Sascha A1 - Schreiner, Monika A1 - Neugart, Susanne T1 - Brassica-enriched wheat bread: Unraveling the impact of ontogeny and breadmaking on bioactive secondary plant metabolites of pak choi and kale JF - Food chemistry N2 - Consumption of Brassica vegetables is linked to health benefits, as they contain high concentrations of the following secondary plant metabolites (SPMs): glucosinolate breakdown products, carotenoids, chlorophylls, and phenolic compounds. Especially Brassica vegetables are consumed as microgreens (developed cotyledons). It was investigated how different ontogenetic stages (microgreens or leaves) of pak choi (Brassica rapa subsp. chinensis) and kale (Brassica oleracea var. sabellica) differ in their SPM concentration. The impact of breadmaking on SPMs in microgreens (7 days) and leaves (14 days) in pak choi and kale as a supplement in mixed wheat bread was assessed. In leaves, carotenoids, chlorophylls, and phenolic compounds were higher compared to those of microgreens. Breadmaking caused a decrease of SPMs. Chlorophyll degradation was observed, leading to pheophytin and pyropheophytin formation. In kale, sinapoylgentiobiose, a hydroxycinnamic acid derivative, concentration increased. Thus, leaves of Brassica species are suitable as natural ingredients for enhancing bioactive SPM concentrations in bread. KW - Ontogeny KW - Brassica KW - Glucosinolate breakdown product KW - Flavonoid KW - Carotenoid KW - Thermal processing Y1 - 2019 U6 - https://doi.org/10.1016/j.foodchem.2019.05.113 SN - 0308-8146 SN - 1873-7072 VL - 295 SP - 412 EP - 422 PB - Elsevier CY - Oxford ER - TY - JOUR A1 - Witzel, Katja A1 - Abu Risha, Marua A1 - Albers, Philip A1 - Börnke, Frederik A1 - Hanschen, Franziska S. T1 - Identification and Characterization of Three Epithiospecifier Protein Isoforms in Brassica oleracea JF - Frontiers in plant science N2 - Glucosinolates present in Brassicaceae play a major role in herbivory defense. Upon tissue disruption, glucosinolates come into contact with myrosinase, which initiates their breakdown to biologically active compounds. Among these, the formation of epithionitriles is triggered by the presence of epithiospecifier protein (ESP) and a terminal double bond in the glucosinolate side chain. One ESP gene is characterized in the model plant Arabidopsis thaliana (AtESP; At1g54040.2). However, Brassica species underwent genome triplication since their divergence from the Arabidopsis lineage. This indicates the presence of multiple ESP isoforms in Brassica crops that are currently poorly characterized. We identified three B. oleracea ESPs, specifically BoESP1 (LOC106296341), BoESP2 (LOC106306810), and BoESP3 (LOC106325105) based on in silico genome analysis. Transcript and protein abundance were assessed in shoots and roots of four B. oleracea vegetables, namely broccoli, kohlrabi, white, and red cabbage, because these genotypes showed a differential pattern for the formation of glucosinolate hydrolysis products as well for their ESP activity. BoESP1 and BoESP2 were expressed mainly in shoots, while BoESP3 was abundant in roots. Biochemical characterization of heterologous expressed BoESP isoforms revealed different substrate specificities towards seven glucosinolates: all isoforms showed epithiospecifier activity on alkenyl glucosinolates, but not on non-alkenyl glucosinolates. The pH-value differently affected BoESP activity: while BoESP1 and BoESP2 activities were optimal at pH 6-7, BoESP3 activity remained relatively stable from pH 4 to 7. In order test their potential for the in vivo modification of glucosinolate breakdown, the three isoforms were expressed in A. thaliana Hi-0, which lacks AtESP expression, and analyzed for the effect on their respective hydrolysis products. The BoESPs altered the hydrolysis of allyl glucosinolate in the A. thaliana transformants to release 1-cyano-2,3-epithiopropane and reduced formation of the corresponding 3-butenenitrile and allyl isothiocyanate. Plants expressing BoESP2 showed the highest percentage of released epithionitriles. Given these results, we propose a model for isoform-specific roles of B. oleracea ESPs in glucosinolate breakdown. KW - epithionitrile KW - expression profile KW - functional complementation KW - glucosinolate hydrolysis KW - nitrile KW - specifier proteins KW - tissue specificity Y1 - 2019 U6 - https://doi.org/10.3389/fpls.2019.01552 SN - 1664-462X VL - 10 PB - Frontiers Research Foundation CY - Lausanne ER - TY - JOUR A1 - Wiesner-Reinhold, Melanie A1 - Schreiner, Monika A1 - Baldermann, Susanne A1 - Schwarz, Dietmar A1 - Hanschen, Franziska S. A1 - Kipp, Anna Patricia A1 - Rowan, Daryl D. A1 - Bentley-Hewitt, Kerry L. A1 - McKenzie, Marian J. T1 - Mechanisms of Selenium Enrichment and Measurement in Brassicaceous Vegetables, and Their Application to Human Health JF - Frontiers in plant science N2 - Selenium (Se) is an essential micronutrient for human health. Se deficiency affects hundreds of millions of people worldwide, particularly in developing countries, and there is increasing awareness that suboptimal supply of Se can also negatively affect human health. Selenium enters the diet primarily through the ingestion of plant and animal products. Although, plants are not dependent on Se they take it up from the soil through the sulphur (S) uptake and assimilation pathways. Therefore, geographic differences in the availability of soil Se and agricultural practices have a profound influence on the Se content of many foods, and there are increasing efforts to biofortify crop plants with Se. Plants from the Brassicales are of particular interest as they accumulate and synthesize Se into forms with additional health benefits, such as methylselenocysteine (MeSeCys). The Brassicaceae are also well-known to produce the glucosinolates; S-containing compounds with demonstrated human health value. Furthermore, the recent discovery of the selenoglucosinolates in the Brassicaceae raises questions regarding their potential bioefficacy. In this review we focus on Se uptake and metabolism in the Brassicaceae in the context of human health, particularly cancer prevention and immunity. We investigate the close relationship between Se and S metabolism in this plant family, with particular emphasis on the selenoglucosinolates, and consider the methodologies available for identifying and quantifying further novel Se-containing compounds in plants. Finally, we summarize the research of multiple groups investigating biofortification of the Brassicaceae and discuss which approaches might be most successful for supplying Se deficient populations in the future. KW - Brassica vegetables KW - selenium KW - biofortification KW - glucosinolates KW - human health KW - immune system KW - cancer KW - analytical methods Y1 - 2017 U6 - https://doi.org/10.3389/fpls.2017.01365 SN - 1664-462X VL - 8 PB - Frontiers Research Foundation CY - Lausanne ER -