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glucosinolates
LWT-FOOD SCIENCE AND TECHNOLOGY · 2025 · IF 6.6

Extraction of glucosinolates from Raphani semen using natural green deep eutectic solvents combined with ultrasound-assisted techniques: process optimization, component analysis, and antibacterial activity evaluation

Mengqi Yan,Sen Li,Ruitong Du,Kang Yang,Zejun Liu,Bingyou Yang,Haixue Kuang,Zhibin Wang

In this study, developed an efficient and environmentally friendly method for selectively extracting glucosinolates (GLS) from Raphani semen ( R. semen ) by integrating ultrasound-assisted extraction (UAE) with natural deep eutectic solvents (NADES). The extraction efficiency of 19 different NADES for GLS in R . semen under ultrasonic conditions was investigated, and it was found that betaine-levulinic acid exhibited outstanding dissolution performance. The extraction process was optimized using response surface methodology (RSM). Under optimal conditions, the GLS yield reached 93.86 mg/g, outperforming traditional solvents. Meanwhile, nine GLS compounds were identified using UHPLC-Q-TOF MS, and the interaction of the most abundant GLS with the solvent was simulated using molecular dynamics (MD). The extract exhibited significant antibacterial activity against Staphylococcus aureus ( S . aureus ) and Escherichia coli ( E . coli ). Additionally, the combination of the extract with ampicillin sodium demonstrated excellent additive and synergistic effects against E . coli and S . aureus , respectively. More importantly, compared to antibiotics, the extract has a reduced tendency to develop resistance. Overall, this promising and low-cost extraction technology provides a new strategy for further exploration of potential novel antimicrobial agents or adjuvants to combat bacterial infections.

研究领域: 植物化学 · 天然产物研究 · 药理学
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JOURNAL OF PLANT GROWTH REGULATION · 2024 · IF 3.9

Effects of LED Light Quality on Broccoli Microgreens Plant Growth and Nutrient Accumulation

Luo Liping,Zhang Gaowei,Liang Wenjing,Wu Dong,Sun Qifang,Hao Yingbin

Broccoli microgreens represent a novel type of vegetable characterized by high levels of bioactive compounds. Here, we investigated the effects of light-emitting diode (LED) light quality on the development and nutritional uptake of broccoli microgreens. The plants were exposed to five distinct light treatments: white, single red, and red: blue at 5:1, 5:3, and 5:5 ratios. The soluble sugars, nutrients, and secondary metabolites of broccoli sprout extracts were examined using high-performance liquid chromatography and ultra-high-performance liquid chromatography quadrupole time-of-flight mass spectrometry under various light-quality conditions. In addition, the expression levels of genes encoding important enzymes in the glucosinolates (GLs) biosynthesis pathway were examined using quantitative real-time polymerase chain reaction. Overall, the findings demonstrated that mixed red-blue light, especially the 5:1 red: blue ratio, was beneficial for broccoli microgreens in terms of their hypocotyl length, fresh weight, edible rate, soluble proteins, vitamin C, total phenolics, total flavonoids, and GLs. Our findings provide a foundation and reference point for selecting the most appropriate LED light ratio in microgreens production.

研究领域: 植物学 · 农业科学 · 食品科学
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JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES · 2020 · IF 0.992

Isolation, identification, biological estimation, and profiling of glucosinolates in Isatis indigotica roots

Qihui Guo,Yanzhi Sun,Qingjiu Tang,Hongchao Zhang,Zhihong Cheng

Four main glucosinolates (progoitrin, epiprogoitrin, gluconapin, and neoglucobrassicin) were isolated and identified from Isatis indigotica roots (Isatidis Radix). Among these, neoglucobrassicin was the first indole glucosinolate isolated from this herb, and its structure was elucidated by NMR, MS, and X-ray diffraction analysis. The glucosinolate components of Isatidis Radix have been profiled by combined use of a conventional preparative column chromatography method and a new UHPLC-QTOF-MS/MS method, and validated by simultaneous analysis of intact and desulfurized GLS. A total of 16 glucosinolates (GLS) including 12 aliphatic GLS, two aromatic GLS, and two indole GLS were identified on the basis of their UV profiles, MS/MS data, and/or by comparison with reference substances. Among these nine GLS were reported from I. indigotica for the first time. The total GLS, four isolated GLS, and (R,S)-goitrin (a degraded product of progoitrin and epiprogoitrin) have been estimated in vitro for anti-influenza viral, anti-bacterial, and anti-inflammatory activities. All the glucosinolate samples were inactive against H3N2 virus and four pathogenic bacteria, and two previously unnoticed GLS (gluconapin and neoglucobrassicin) showed significantly anti-inflammatory activity against the respiratory burst of mouse macrophages.

CAS / MDL: 64-18-6 76-05-1
研究领域: 药理学 · 分析化学 · 植物科学
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FOOD CHEMISTRY · 2024 · IF 8.5

Effects and mechanism of metal ions on the stability of glucosinolates in aqueous solution

Mintong Tian,Purui Yu,Zehua Li,Ce Liu,Hao Liang,Qipeng Yuan

Glucosinolates (GLs) are important precursors of anticancer isothiocyanates in cruciferous plants. However, GLs in aqueous solution have been found to decompose under certain conditions, and the effect of metal ions remains unclear. In this study, high-purity glucoraphanin and glucoraphenin were used to explore the effects of metal ions with thermal treatment. The degree of GLs decomposition was affected by the type and concentration of metal ions, temperature, and duration of heating. Fe 3+ (1 mM) was found to cause the decomposition of 78.1 % of glucoraphanin and 94.7 % of glucoraphenin in 12 h at 100 °C, while Cu 2+ completely decomposed both GLs. The decomposition products were all the corresponding nitriles, and decomposition dynamic curves were first-order. In addition to accelerating hydrolysis, metal ions may promote the generation of nitriles as catalysts. The exploration of GLs decomposition could help to adopt more effective methods to avoid the formation of toxic compounds.

研究领域: 植物化学 · 食品科学 · 分子生物学
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FOOD CHEMISTRY · 2022 · IF 9.231

Determination of glucosinolates in rapeseed meal and their degradation by myrosinase from rapeseed sprouts

Chong Xie,Wanmei Li,Rongguang Gao,Lihua Yan,Pei Wang,Zhenxin Gu,Runqiang Yang

The utilization of rapeseed meal in food is limited due to its abundant glucosinolates (GLs). In this study, an LC-MS/MS method for GLs determination in rapeseed meal was developed. Then, the degradation of GLs using rapeseed sprouts derived myrosinase (MYR) was investigated. Results showed that 11 kinds of GLs were identified in rapeseed meal. The LC-MS/MS method had a high linearity (R 2  greater than 0.9999), repeatability (RSD < 5%) and recovery rate (92%-102%). The optimum condition for hydrolyzing GLs in rapeseed meal was reacting for 4 h with the addition of 2236.35 U/g MYR, 9.63 μg/g ascorbic acid and 26.68 μg/g EDTA. Under this condition, more than 80% of GLs were degraded and the yields of isothiocyanates and oxazolidinone-2-thione were 859.30 μg/g and 685.59 μg/g, respectively. To conclude, this study reported a reliable method for GLs determination and an effective way to degrade GLs in rapeseed meal.

研究领域: 食品科学 · 分析化学 · 酶学
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FOOD RESEARCH INTERNATIONAL · 2022 · IF 7.425

Microwave bag cooking affects the quality, glucosinolates content and hydrolysate production of broccoli florets

Wenxiu Zheng,Wenhao Wang,Desheng Fu,Tianyu Zhang,Zhengrui Liang,Ling Yan,Changhong Liu,Lei Zheng

Appropriate processing and cooking technologies can effectively improve the content of bioactive compounds in vegetables. The effects of microwave bag cooking on broccoli floret quality attributes, glucosinolates (GLSs) content and hydrolysate production were investigated in this study. Microwave bag cooking not only preserved the color of the florets, but also enhanced the total phenolic and flavonoid content, as well as total chlorophyll and ascorbic acid content. Furthermore, the majority of the microorganisms were inactivated, and the structure of the florets was greatly destroyed, thereby increasing antioxidant capacity and promoting the release of GLSs and myrosinase activity in the florets. Moreover, microwave bag cooking significantly enriched the sulforaphane (SFN) and indole-3-carbinol (I3C) production of broccoli florets in the meantime, demonstrating that it was a convenient and quick cooking option to satisfy the requirements of modern consumers.

CAS / MDL: 700-06-1 4478-93-7
研究领域: 食品科学 · 营养学 · 生物化学
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Horticultural Plant Journal · 2022 · IF 4.24

Effects of fresh-cut and storage on glucosinolates profile using broccoli as a case study

Xiaoxin Huang,Bing Cheng,Yaqin Wang,Guangmin Liu,Liping Hu,Xiaolu Yu,Hongju He

Glucosinolates (GLS) contribute to the unique flavour, nutrition, and plant defence of the Cruciferous vegetables. Understanding the GLS changes through postharvest processing is essential for defined preservation. In this study, four different fresh-cut types, whole flower (W), floret (F), quarterly cut floret (QF) and shredded floret (FS) of broccoli, were stored for 0, 1, 2 and 3 day (s) to explore GLS responses to postharvest treatments. As a result, seven GLS were identified, mainly including glucoraphanin (RAA), neoglucobrassicin (NEO), and glucobrassicin (GBC) and accounting for 52.69%, 20.12% and 14.99% of the total GLS (21.92 ± 0.48) μmol · g -1 DW, respectively. FS had the sharpest decrease in GLS after three days of storage (6.55 ± 0.37) μmol · g -1 DW, while QF had the least (10.16 ± 0.33) μmol · g -1 DW. All GLS components decreased over storage, except for 4-methoxyglucobrassicin (4 ME) in FS and QF, suggesting its key role in serious wound defence. The results suggested certain postharvest approaches influenced the flavour and nutrition of broccoli.

CAS / MDL: 7681-52-9 7558-79-4
研究领域: 食品科学 · 植物化学
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FOOD RESEARCH INTERNATIONAL · 2025 · IF 8

Thermal stability, and in vitro and in vivo metabolism of four main glucosinolates in Isatis indigotica roots

Yanzhi Sun,Qihui Guo,Zhihong Cheng

The glucosinolates (GLSs) and their degradation products (such as goitrin) in Isatis indigotica roots have been the subject of considerable research interest due to their antiviral activities. The degradation mechanism and products of GLSs under the endogenous myrosinase are well-established. Nevertheless, it remains uncertain whether GLSs in I. indigotica roots can undergo thermal decomposition, or whether the two principal GLSs (progoitrin and epiprogoitrin) can biotransform into the bioactive goitrin in the absence of myrosinase. In this study, the thermal stability and metabolic behavior of four main GLSs (including progoitrin, epiprogoitrin, gluconapin, and neoglucobrassicin) were estimated for the first time. Gluconapin demonstrated the most robust thermal stability among the four GLSs, retaining its structural integrity even at 100 °C. The remaining three GLSs were found to be stable only at lower temperatures (0–20 °C), exhibiting degradation at 40 °C and complete degradation at 60 °C. The degraded products of the three GLSs were subjected to analysis by static headspace GC–MS, which were identified as isothiocyanates, thiocyanates, nitriles, and enols. The four GLSs were not biotransformed into their respective products by simulated gastric fluid, simulated intestinal fluid, rat liver microsomes, or human intestinal flora. The in vivo metabolism study of the aliphatic glucosinolates (progoitrin, epiprogoitrin, gluconapin, and sinigrin) in mice revealed that the intact GLS and their metabolites of these four GLSs were undetected in the mice plasma by UPLC-ESI-MS/MS, indicating that the GLS were poorly absorbed into the blood. However, only a common minor metabolite of the four GLSs were identified in the urine of the mice, along with abundant intact GLSs. The metabolite was identified as N -acetylcysteine conjugates by LC-MS, with the aid of the reported mercapturic acid metabolic pathway of GLSs. The findings of this study indicated that the GLSs are predominantly excreted in urine in their original forms and are not absorbed into the bloodstream. In conclusion, the two principal GLSs (progoitrin and epiprogoitrin) in I. indigotica roots are unable to undergo conversion to active goitrin under conditions of heat stress or physiological stress in the absence of myrosinase.

CAS / MDL: 103-90-2
研究领域: 药物化学 · 天然产物化学 · 药代动力学 · 植物化学 · 生物转化
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JOURNAL OF FOOD COMPOSITION AND ANALYSIS · 2020 · IF 3.721

Metabolomic analysis based on EESI-MS indicate blue LED light promotes aliphatic-glucosinolates biosynthesis in broccoli sprouts

Ahui Xue,Wenjing Liang,Shide Wen,Yuanyuan Gao,Xueyong Huang,Yuzhen Tong,Yingbin Hao,Liping Luo

Broccoli sprouts are rich in secondary metabolites, especially glucosinolates (GLs). The synthesis of GLs can be modified by light. In this study, extractive electrospray ionization-mass spectrometry (EESI-MS) was used to analyze the broccoli sprouts extracts (BSE) under different light quality treatments. Multivariable statistical methods were used to analyze the difference of different light quality treatments. Quantitative real-time polymerase chain reaction (qRT-PCR) was used to analyze the gene expression of key enzymes in the aliphatic-GLs biosynthesis pathway. Nineteen compounds, including 7 GLs, 3 phenolic acids, 6 amino acids and 3 organic acids were simultaneously detected in one minute by EESI-MS. Relative expression of MYB28 , BCAT4 , CYP79F1 , CYP83A1 and AOP3 were mostly upregulated in R5B5 (light ratios of red/blue 5:5) treatment. These findings suggest that blue light improving the accumulation of secondary metabolites in broccoli sprouts, and the R5B5 treatment was most beneficial. Furthermore, we established EESI-MS method to simultaneous and rapid detection of secondary metabolites in broccoli sprouts, especially GLs. This study could provide a reference for selecting proper LED lighting conditions to produce broccoli sprouts with high content of bioactive components, and provides light regulation technology and theoretical basis for the industrialized production of sprouts.

研究领域: 植物学 · 代谢组学 · 农业科学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2023 · IF 6

Molecular networking and equivalently quantitative ion strategy for discovery and quantification of glucosinolates in cauliflower and broccoli by liquid chromatography tandem mass spectrometry

E. Hengchao,Shuting Peng,Zhiyong Zhao,Xueqin Yao,Yanmei Zhang,Xiaobei Li,Xianli Yang,Tingting Fan,Xiaoyan Zhao,Changyan Zhou

Glucosinolates (GSLs) are unique secondary metabolites in cauliflower and broccoli, which have diverse biological activities. In this study, a molecular networking combined with the equivalently quantitative ion strategy was built based on liquid chromatography tandem mass spectrometry (LC-MS/MS) for the discovery and quantification of GSLs in cauliflower and broccoli. Firstly, 19 GSLs were identified including 2 new compounds, 4-hydroxyneoglucobrassicin and gluco-4-hydroxyneoglucobrassicin. Moreover, the shared fragment ion m/z 96.0 was set as the equivalently quantitative ion to quantify GSLs. This method could use only one reference standard (or one calibration curve) to efficiently quantify all aliphatic and phenyl GSLs in cauliflower and broccoli. This method was fully validated with good linearity, recovery and sensitivity, and subsequently applied in GSLs quantification. The developed strategy could also be applied in GSLs discovery and quantification in other Brassicaceae vegetables.

CAS / MDL: 631-61-8
研究领域: 分析化学 · 食品科学 · 植物科学 · 植物化学
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FOOD RESEARCH INTERNATIONAL · 2023 · IF 8.1

Identification of glucosinolates and volatile odor compounds in microwaved radish (Raphanus sativus L.) seeds and the corresponding oils by UPLC-IMS-QTOF-MS and GC × GC-qMS analysis

Xiao Jia,Pei Yu,Qi An,Jingnan Ren,Gang Fan,Zelan Wei,Xixiang Li,Siyi Pan

The effect of microwave treatment on the content of glucosinolates (GSL) in radish seeds and volatile odor compounds in the microwaved radish seed oils (MRSO) is still unclear. In this study, a total of 13 GSL were identified and quantified in five radish seed varieties by UPLC-IMS-QTOF-MS, among which glucoraphenin, glucoraphasatin, glucoerucin accounting for up to 90 %. Total GSL decreased by 47.39–67.88% after microwave processing. Moreover, 58 odor compounds were identified in MRSO, including 6 sulfides, 12 nitriles, 2 isothiocyanates, 10 alcohols, 12 aldehydes, 5 ketones, 6 acids, and 5 others. The major odor compounds were (methyldisulfanyl)methane, dimethyltrisulfane, (methylsulfinyl)methane, 3-(methylsulfanyl)-1-propanol, methyl thiocyanate, hexanenitrile, 5-(methylsulfanyl)pentanenitrile, and 4-isothiocyanato-1-butene with odor activity value (OAV) higher than 1. The principal components analysis (PCA) results can distinguish MRSO from five different radish seed varieties, three of which (H20-18, H20-19 and H20-28) were in one group and other two (H20-23 and H20-26) were in another group. In addition, aliphatic GSL showed positive correlations with sulfides, isothiocyanates, and nitriles, while negative correlations with alcohols. This work provides a new insight into the odor contribution of GSL degradation products.

研究领域: 食品科学 · 分析化学 · 植物生物化学
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