Sinapic acid derivatives in defatted Oriental mustard (Brassica juncea L.) seed meal extracts using UHPLC-DAD-ESI-MS n and identification of compounds with antibacterial activity

Engels, Christina; Schieber, Andreas; Gänzle, Michael G.

doi:10.1007/s00217-012-1669-z

Cited by 130 publications

(98 citation statements)

References 33 publications

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“…These findings are similar to those of this study, although the MIC of sinapic acid against E. coli were different. Engels and others () observed that the inhibitory effects of sinapic acid was strong in the order of L. monocytogenes (MIC, 0.2 g/L) > S. aureus, B. subtilis, L. innocua (0.3 g/L) > P. fluorescens (0.6 g/L) > E. coli (0.7 g/L), which are similar results to those of this study in terms of relative antibacterial activity against each bacterial strain. On the other hand, the MIC of sinapic acid against L. plantarum was found to be greater than 0.7 g/L, indicating the antibacterial activity of sinapic acid is remarkably selective (Engels and others ).…”

Section: Resultssupporting

confidence: 90%

“…Engels and others () observed that the inhibitory effects of sinapic acid was strong in the order of L. monocytogenes (MIC, 0.2 g/L) > S. aureus, B. subtilis, L. innocua (0.3 g/L) > P. fluorescens (0.6 g/L) > E. coli (0.7 g/L), which are similar results to those of this study in terms of relative antibacterial activity against each bacterial strain. On the other hand, the MIC of sinapic acid against L. plantarum was found to be greater than 0.7 g/L, indicating the antibacterial activity of sinapic acid is remarkably selective (Engels and others ). Sinapic acid, a type of phenolic acid, is a weak acid that diffuses across microbial cell membranes as an undissociated acid, causing acidification of the cytoplasm and eventually cell death (Sánchez‐Maldonado and others ).…”

Section: Resultssupporting

confidence: 90%

“…Sinapic acid is also a more effective antioxidant than sinapine during lipid oxidation, as sinapine was shown to be slightly prooxidative or to have no inhibitory effect on hydroperoxide formation, whereas sinapic acid was shown to have higher antioxidative capacity at higher concentrations (Thiyam and others ). Moreover, sinapic acid has antibacterial effects against spoilage bacteria such as Staphylococcus aureus, Listeria monocytogenes , and Escherichia coli (Tesaki and others ; Engels and others ) as well as low inhibitory activity against Lactobacillus plantarum (Sánchez‐Maldonado and others ). However, the sinapine‐rich fraction of rapeseed flour extract was reported to have no antibacterial effects against spoilage bacteria (Nowak and others ).…”

Section: Introductionmentioning

confidence: 99%

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Effects of Hydrolyzed Rapeseed Cake Extract on the Quality Characteristics of Mayonnaise Dressing

Kim

Lee

2017

Journal of Food Science

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Crude extract of rapeseed cake was fractionated and alkaline-hydrolyzed to convert sinapine into sinapic acid, and the produced hydrolyzed extract showed higher antimicrobial and antioxidative activities than the crude extract. When the hydrolyzed extract was added to mayonnaise dressing, microbial stability increased along with physical characteristics and oxidative stability, thereby supporting the potential of hydrolyzed rapeseed extract as a food additive for quality management of mayonnaise dressing during storage.

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Section: Resultssupporting

confidence: 90%

Section: Resultssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

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Effects of Hydrolyzed Rapeseed Cake Extract on the Quality Characteristics of Mayonnaise Dressing

Kim

Lee

2017

Journal of Food Science

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“…2.6–5.0 mg/g expressed as the sinapic acid equivalent. Also several new compounds (kaempferol‐sinapoyl‐trihexoside, sinapoyl‐hexoside, disinapoyl‐dihexoside, disinapoyl‐hexoside, and sinapoyl conjugates) were found by Engels et al during their studies on antimicrobial properties of sinapic acid derivatives present in seeds of mustard ( Brassica juncea L.).…”

Section: Introductionmentioning

confidence: 95%

Identification and antioxidant activity of sinapic acid derivatives in Brassica napus L. seed meal extracts

Siger

Czubiński

Dwiecki

et al. 2013

Euro J Lipid Sci & Tech

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Sinapic acid and its derivatives are main phenolic compounds present in rapeseed. Identification and quantitative determination of those compounds were carried out in crude extracts as well as extracts after basic and acidic hydrolysis. The total phenolic content in the crude extracts, expressed as sinapic acid equivalent, ranged from 1577 to 1705 mg/100 g for cv. Visby and Bellevue, respectively. An increase in total phenolics contents was observed in extracts after hydrolysis in comparison to crude extracts. The predominant phenolic acids in rapeseed samples were trans‐sinapic and cis‐sinapic acids. The highest concentration of sinapic acid methyl ester (2533–2702 mg/100 g) was detected in the extract after basic hydrolysis. In turn, two sinapic acid derivatives, i.e., kaempferol 3‐dihexoside‐7‐sinapoyl‐hexoside and 3‐hexoside‐7‐sinapoyl‐hexoside, were detected in the hydrolysed extracts. Total peroxyl radical‐trapping potential (TRAP) of the investigated crude extracts amounted to 20.21 and 27.05 μM Trolox Eq/g in the case of cv. Visby and Bellevue, respectively. The increase in antioxidant activity of the analyzed extracts after basic and acidic hydrolysis was probably a result of the release of free phenolic compounds from their conjugates (esters, glycosides). Practical applications: The content and qualitative composition of the phenolic compounds in rapeseed have much influence on the stability, sensory, and nutritional characteristics of the products. During oil production process phenolic compounds may be transferred into final products and inhibit lipid oxidation. Rapeseed oil, among all commercially available oils, has the highest content of phenolic compounds, especially sinapic acid and their derivatives. That is why the antioxidant activity of phenolic compounds was investigated in the presented study. Determination of polar phenolics before and after hydrolysis indicates which compounds are responsible for antioxidant effect in oils and which are available for the human organism after digestion in the digestive tract.

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“…Actually, camalexin disrupts cell membrane of bacterial and fungal pathogens 24 . However, phenolic compounds like sinapic, phytic acids and derivatives of flavonols (qucercetin) have been considered as potent antioxidant with antimicrobial, anti-inflammatory and anticancer properties by many workers 14,25,26 . It is speculated that the mechanism of flavonoid antimicrobial activity is due to their ability to inhibition of microbial adhesion and inactivation of cell envelope transport proteins 14 .…”

Section: Resultsmentioning

confidence: 99%

In Vitro Antioxidant and Anti-rhizopus Activity of Methanolic Seed Extract of Camelina Sativa L.

Gupta

Kumar

2017

Def. Life. Sc. Jl.

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The antifungal efficacy of seed extracts (propanol, ethanol, methanol and sterile deionised water) of Camelina sativa cv. Calena (EC643910) against Rhizopus stolonifer was investigated by agar disc diffusion method. Among all extracts, methanolic seed extract (Disc 3) showed significant activity against R. stolonifer. However, no activity was observed against rest of the extracts (Disc 1, 2 and 4). The inhibition zones were ~35 mm for methanolic extract and ~41 mm for standard drug, respectively. The total phenol content was observed 13.5 µmol, 23.3 µmol, 42.9 µmol and 3.4 µmol gDW -1 in propanolic, ethanolic, methanolic and sterile deionised water extracts of Camelina, respectively. Likewise, the ascorbate peroxidase (APX) activity was observed highest in methanolic extract that was ~10.2, ~2.4 and ~5.7-folds higher as compared to propanolic, ethanolic and sterile deionised water extracts, respectively. Similarly, guaiacol peroxidase (GPX) activity was also observed highest in methanolic extract as compared to other extracts, which is ~7.3, ~1.9 and ~6.6-folds higher as compared to propanolic, ethanolic and sterile deionised water extracts, respectively. The findings of the study clearly speculate that the possibility of using methanolic seed extract of Camelina as a potential control measure against R. stolonifer, which may be used for the development of future herbal drug formulations.

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Sinapic acid derivatives in defatted Oriental mustard (Brassica juncea L.) seed meal extracts using UHPLC-DAD-ESI-MS n and identification of compounds with antibacterial activity

Cited by 130 publications

References 33 publications

Effects of Hydrolyzed Rapeseed Cake Extract on the Quality Characteristics of Mayonnaise Dressing

Effects of Hydrolyzed Rapeseed Cake Extract on the Quality Characteristics of Mayonnaise Dressing

Identification and antioxidant activity of sinapic acid derivatives in Brassica napus L. seed meal extracts

In Vitro Antioxidant and Anti-rhizopus Activity of Methanolic Seed Extract of Camelina Sativa L.

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