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Sinapine ( O ‐sinapoyl choline) is the major phenolic metabolite typically found in the oil‐rich seeds of Brassicaceae such as Camelina sativa and Brassica napus . It imparts a bitter taste to the seeds as a defence mechanism against herbivores, but it also renders them less palatable to livestock. To improve Camelina flour for human consumption or as animal feed, we reduced sinapine content through CRISPR/Cas9‐based genome editing of REF1 ( REDUCED EPIDERMAL FLUORESCENCE1 ), which encodes the NADP + ‐dependent coniferaldehyde/sinapaldehyde dehydrogenase (CALDH/SALDH), a key enzyme for sinapine biosynthesis in Arabidopsis thaliana and B. napus . Inactivation of all three homoeologues found in C. sativa lowered the sinapine content in seeds by an overall 56% in two cultivars indicating the presence of a REF1‐independent pathway for sinapine biosynthesis. Most importantly however, crucial agronomic seed traits such as total lipid or protein content of the seeds, seed weight or germination were not affected. Hence, the ref1 mutant lines produced here provide a valuable trait, that can be combined with other traits through gene stacking to obtain crops with significantly improved product quality. Furthermore, metabolite fingerprinting by ultra‐performance liquid chromatography‐electrospray ionisation‐quadrupole time‐of‐flight mass spectrometry of ref1 mutant lines revealed a contrasting phenylpropanoid profile in seeds and leaves, indicating that REF1 oxidises sinapaldehyde to sinapate in seeds and coniferyl aldehyde to ferulate in leaves. In contrast to Arabidopsis however, Camelina accumulates no comparable levels of sinapoyl malate, but substantial amounts of chlorogenic acid, of which an additional chlorogenic acid isomer distinguishes the two different Camelina cultivars as a metabolite marker.

The increase of blood pressure is accompanied by the changes in the morphology and function of vascular endothelial cells. Vascular endothelial injury and hypertension actually interact as both cause and effect. A large number of studies have proved that inflammation plays a significant role in the occurrence and development of hypertension, but the potential mechanism between inflammation and hypertensive endothelial injury is still ambiguous. The purpose of this study was to explore the association between the activation of NLRP3 inflammasome and hypertensive endothelial damage, and to demonstrate the protective effect of sinapine thiocyanate (ST) on endothelia in hypertension. The expression of NLRP3 gene was silenced by tail vein injection of adeno-associated virus (AAVs) in spontaneously hypertensive rats (SHRs), indicating that activation of NLRP3 inflammasome accelerated hypertensive endothelial injury. ST not only protected vascular endothelial function in SHRs by inhibiting the activation of NLRP3 inflammasome and the expression of related inflammatory mediators, but also improved AngII-induced huvec injury. In summary, our results show that alleviative NLRP3 inflammasome activation attenuates hypertensive endothelial damage and ST ameliorates vascular endothelial dysfunction in hypertension via inhibiting activation of the NLRP3 inflammasome.

The aim of this paper is to study the effect of the pH on the extraction of sinapic acid and its derivatives from mustard seed meal. Solutions of acidic pH (pH 2), basic pH (pH 12) and distilled water (uncontrolled pH ~ 4.5) were tested at different percentages of ethanol. The maximum extraction yield for sinapic acid (13.22 µmol/g of dry matter (DM)) was obtained with a buffered aqueous solution at pH 12. For ethyl sinapate, the maximum extraction yield reached 9.81 µmol/g DM with 70% ethanol/buffered aqueous solution at pH 12. The maximum extraction yield of sinapine (15.73 µmol/g DM) was achieved with 70% ethanol/buffered aqueous solution at pH 2. The antioxidant activity of each extract was assessed by DPPH assay; the results indicated that the extracts obtained at pH 12 and at low ethanol percentages (<50%) exhibit a higher antioxidant activity than extracts obtained at acidic conditions. Maximum antioxidant activity was reached at pH 12 with buffer solution (11.37 mg of Trolox Equivalent/g DM), which confirms that sinapic acid-rich fractions exhibit a higher antioxidant activity. Thus, to obtain rich antioxidant extracts, it is suggested to promote the presence of sinapic acid in the extracts.

Sinapine is a phenolic compound found in mustard (Brassica juncea) seed meal. It has numerous beneficial properties such as antitumor, neuroprotective, antioxidant, and hepatoprotective effects, making its extraction relevant. In this study, the extraction of sinapine was investigated using three methods: (i) from a mustard seed meal defatted by a supercritical CO2 (SC-CO2) pretreatment, (ii) by the implementation of high-voltage electrical discharges (HVEDs), (iii) and by the use of ultrasound. The use of SC-CO2 pretreatment resulted in a dual effect on the valorization of mustard seed meal, acting as a green solvent for oil recovery and increasing the yield of extracted sinapine by 24.4% compared to the control. The combination of ultrasound and SC-CO2 pretreatment further increased the yield of sinapine by 32%. The optimal conditions for ultrasound-assisted extraction, determined through a response surface methodology, are a temperature of 75 °C, 70% ethanol, and 100% ultrasound amplitude, resulting in a sinapine yield of 6.90 ± 0.03 mg/g dry matter. In contrast, the application of HVEDs in the extraction process was not optimized, as it led to the degradation of sinapine even at low-energy inputs.

Rapeseed polyphenols have cardiovascular protective effects. Sinapine, one main rapeseed polyphenol, possesses antioxidative, anti-inflammatory, and antitumor properties. However, no research has been published about the role of sinapine in alleviating macrophage foaming. This study aimed to reveal the macrophage foaming alleviation mechanism of sinapine by applying quantitative proteomics and bioinformatics analyses. A new approach was developed to retrieve sinapine from rapeseed meals by using hot-alcohol-reflux-assisted sonication combined with anti-solvent precipitation. The sinapine yield of the new approach was significantly higher than in traditional methods. Proteomics was performed to investigate the effects of sinapine on foam cells, and it showed that sinapine can alleviate foam cell formation. Moreover, sinapine suppressed CD36 expression, enhanced the CDC42 expression, and activated the JAK2 and the STAT3 in the foam cells. These findings suggest that the action of sinapine on foam cells inhibits cholesterol uptake, activates cholesterol efflux, and converts macrophages from pro-inflammatory M1 to anti-inflammatory M2. This study confirms the abundance of sinapine in rapeseed oil by-products and elucidates the biochemical mechanisms of sinapine that alleviates macrophage foaming, which may provide new perspectives for reprocessing rapeseed oil by-products.

In this study, phenolic compounds from an aqueous protein by-product from rapeseed meal (RSM) were identified by HPLC-DAD and HPLC-ESI-MS, including sinapine, sinapic acid, sinapoyl glucose, and 1,2-di-sinapoyl gentibiose. The main phenolic compound in this by-product was sinapine. We also performed acid hydrolysis to convert sinapine, and sinapic acid derivatives present in the permeate, to sinapic acid. The adsorption of phenolic compounds was investigated using five macroporous resins, including XAD4, XAD7, XAD16, XAD1180, and HP20. Among them, XAD16 showed the highest total phenolic contents adsorption capacities. The adsorption behavior of phenolic compounds was described by pseudo-second-order and Langmuir models. Moreover, thermodynamics tests demonstrated that the adsorption process of phenolic compounds was exothermic and spontaneous. The highest desorption ratio was obtained with 30% (v/v) and 70% (v/v) ethanol for sinapine and sinapic acid, respectively, with a desorption ratio of 63.19 ± 0.03% and 94.68 ± 0.013%. DPPH and ABTS tests revealed that the antioxidant activity of the hydrolyzed fraction was higher than the non-hydrolyzed fraction and higher than the one of vitamin C. Antioxidant tests demonstrated that these phenolic compounds could be used as natural antioxidants, which can be applied in the food industry.

Sinapine thiocyanate (ST), an alkaloid isolated from the seeds of cruciferous species, has exhibited anti-inflammatory, anti-malignancy, and anti-angiogenic effects in previous studies. However, the effects and molecular mechanisms of action of ST in pancreatic cancer (PC) are still limited. PC cells were treated with different concentrations (0, 20, 40, and 80 μM) of ST. The proliferative ability of PC cells was determined using cell count kit-8 (CCK-8), 5-ethynyl-2' deoxyuridine, colony formation, and flow cytometry assays. The mobility of PC cells was analyzed using wound healing assay, transwell assay, Western blotting, and immunofluorescence. High-throughput sequencing followed by bioinformatics analysis, reverse-transcriptase quantitative polymerase chain reaction (RT-qPCR), and Western blotting were performed to identify the key targets of ST. Finally, CCK-8 assay, wound healing assay, and xenograft tumor model were used to determine the relationship between ST and growth arrest and DNA damage-inducible alpha (GADD45A; the key target of ST) and malignant biological properties of PC and . ST significantly repressed the PC cell proliferation rate and colony formation and arrested cells in the G2/M phase. ST inhibited PC cell mobility and increased E-cadherin expression (an epithelial biomarker). GADD45A was considered the key target of ST in PC and was elevated in PC cells treated with ST. The inhibition of GADD45A significantly alleviated the suppressive effects of ST on PC cell proliferation and mobility . ST suppressed PC cell proliferation and increased GADD45A expression in tumor tissues. ST exhibited significant anti-tumor effects on PC cells by upregulating GADD45A. ST may be a potential drug for PC treatment.

To extract sinapine from rapeseed meal and investigate its antihypertensive function and mechanism. Blood pressure was measured before and after sinapine administration to evaluate sinapine’s immediate antihypertensive function. Twokidney, oneclip (2K1C) hypertensive rats were given sinapine for four weeks, with weekly blood pressure monitoring. The renin angiotensin aldosterone system (RAAS), including the levels of renin, angiotensin I (Ang I), angiotensin II (Ang II), aldosterone (ALD), angiotensin-converting enzyme (ACE) and other molecules related to blood pressure, such as NO, prostacyclin (PGI 2 ), endothelin-1 (ET1), and thromboxane A 2 (TXA 2 ), were measured in rat blood. The impact of sinapine on vascular endothelial cell (A10) calcium and potassium channels was assessed using the patch-clamp technique. One-time or long-term administration of sinapine significantly reduced the rats’ systolic blood pressure (SBP), diastolic pressure (DBP), and mean blood pressure (MBP). Sinapine also decreased the levels of Ang II and ALD. Furthermore, sinapine effectively inhibited ACE activation, increased NO levels, and blocked L-type calcium channels. Sinapine has an antihypertensive function and achieves this process through multiple targets.

Rapeseed is an important oil crop worldwide, with an annual production of more than 70 million tons. Rapeseed meal (RSM) is a by-product of rapeseed oil production and is second after soybean meal (SBM) in the world production of protein meal. Rapeseed meal derived from black-seeded winter oilseed rape ( L.) usually contains between 35 and 40% of crude protein (CP), which is considered to be one of the more valuable plant proteins. It has a good balance of essential amino acids and a very high protein efficiency ratio (PER=3.29). However, full utilisation of this protein is difficult due to presence of the non-protein components of the seed which are associated with it. These are called antinutritional factors and they limit the utilisation of RSM in monogastric animal nutrition. The main antinutritional factors in RSM are dietary fibre, glucosinolates, phytic acid, and phenolic compounds (sinapine, tannins). For many years, research has been conducted in many centres around the world to improve the nutritional value of RSM, which will consequently increase its use in feeding monogastric animals. The attempts that have been undertaken include breeding strategy, optimisation, modernisation and better control of the oil extraction process, as well as technological treatments of seeds and meal. This review provides information on how RSM has evolved in recent years, as well as on its nutritive value, particularly protein, fibre and glucosinolate content. Techniques which have been used to improve the nutritional value of rapeseed products are also discussed. However, the used methods do not allow for full replacement soybean meal by RSM in monogastric animal nutrition.

Summary Mutants with simultaneous germline mutations were obtained in all three F5H genes and all three FAD2 genes (one to eleven mutated alleles) in order to improve the feed value of the seed meal and the fatty acid composition of the seed oil. In mutants with multiple mutated F5H alleles, sinapine in seed meal was reduced by up to 100%, accompanied by a sharp reduction in the S‐monolignol content of lignin without causing lodging or stem break. A lower S‐lignin monomer content in stems can contribute to improved stem degradability allowing new uses of stems. Mutants in all six FAD2 alleles showed an expected increase in MUFA from 8.7% to 74% and a reduction in PUFA from 53% to 13% in the fatty acids in seed oil. Remarkably, some full FAD2 mutants showed normal growth and seed production and not the dwarfing phenotype reported in previous studies. The relation between germline mutation allele dosage and phenotype was influenced by the still ongoing activity of the CRISPR/Cas9 system, leading to new somatic mutations in the leaves of flowering plants. The correlations between the total mutation frequency (germline plus new somatic mutations) for F5H with sinapine content, and FAD2 with fatty acid composition were higher than the correlations between germline mutation count and phenotypes. This shows the importance of quantifying both the germline mutations and somatic mutations when studying CRISPR/Cas9 effects in situations where the CRISPR/Cas9 system is not yet segregated out.