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Sinapine

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-S2022

  • Specification : 98%

  • CAS number : 18696-26-9

  • Formula : C16H24NO5+

  • Molecular Weight : 310.36

  • PUBCHEM ID : 5280385

  • Volume : 20mg

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Catalogue Number

BF-S2022

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

310.36

Appearance

Powder

Botanical Source

Sinapis alba

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

C[N+](C)(C)CCOC(=O)C=CC1=CC(=C(C(=C1)OC)O)OC

Synonyms

Sinapine/2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium/Sinapine bisulphate/sinapic acid choline ester/Sinapoylcholine/O-sinapoylcholine

IUPAC Name

2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium

Density

Solubility

Methanol; Water

Flash Point

Boiling Point

Melting Point

171.0-173.5ºC (dec.)

InChl

InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1

InChl Key

HUJXHFRXWWGYQH-UHFFFAOYSA-O

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:18696-26-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31203621

Abstract

Choline and its metabolites have diverse and important functions in many physiological processes, especially for anabolic metabolism in growth and reproduction. Besides endogenous biosynthesis and direct choline supplement, choline esters in the diet are another source of choline in the body. Phenolic choline esters are a group of unique dietary choline esters rich in the seeds of Brassicaceae plants, among which sinapine is a choline ester of sinapic acid abundant in rapeseed. In this study, 40 nursery pigs were fed with rapeseed-derived feed ingredients (RSF) or soybean meal for 3 weeks (20 pigs/diet). The metabolic fate of sinapine-derived choline in RSF was examined by comparing the distribution of choline and its metabolites in digesta, liver, and serum samples by liquid chromatography-mass spectrometry analysis. The results showed that choline was released from extensive hydrolysis of sinapine in the small intestine. However, sinapine-derived choline did not increase the levels of choline and its major metabolites, including betaine, phosphocholine, and glycerophosphocholine, in the liver and serum. Instead, RSF feeding increased trimethylamine (TMA), the microbial metabolite of choline, in the large intestine and further increased trimethylamine N-oxide (TMAO), the oxidation metabolite of TMA, in the liver and serum. Overall, these results suggested that sinapine-derived choline from rapeseed feeding had limited influences on the post-absorption choline pool as a result of its low bioavailability but may serve as a major source of TMAO through microbial metabolism in nursery pigs. Improving the bioavailability of sinapine-derived choline might have the potential to modify the nutritional values and functionalities of rapeseed meal in swine feeding.

KEYWORDS

TMA; TMAO; choline; pig; rapeseed; sinapine

Title

Identification of Sinapine-Derived Choline from a Rapeseed Diet as a Source of Serum Trimethylamine N-Oxide in Pigs.

Author

Chen H1, Peng L2, Perez de Nanclares M3, Trudeau MP, Yao D, Cheng Z1, Urriola PE, Mydland LT3, Shurson GC, Overland M3, Chen C.

Publish date

2019 Jul 10

PMID

31165837

Abstract

Non-alcoholic fatty liver disease (NAFLD) is associated with low-grade chronic inflammation and intestinal dysbiosis. In this study, we investigated the potential benefits of sinapine, a rapeseed polyphenol known to exert anti-inflammatory and anti-oxidant effects, on high-fat diet (HFD)-induced NAFLD in C57BL/6 J mice and the underlying mechanisms. Four week-old mice were randomly divided into four groups and fed a low-fat diet (LFD), a HFD, a HFD with common rapeseed oil (HFD + CRO) and a HFD with sinapine in rapeseed oil (HFD + SRO) for 12 weeks. Supplementation with sinapine reduced the body weight of HFD mice by 10.99%, and decreased the levels of TG and LDL-C by 15.67% and 73.62%, respectively. In addition, sinapine also suppressed the intestinal NF-κB and TNF-α expressions and enhanced the adipose tissue IRS-1 expression in the HFD mice (P < 0.05). In terms of effects on the gut microbiota, sinapine induced a decrease in the ratio of Firmicutes to Bacteroidetes and increased the abundance of probiotics, such as Lactobacillaceae, Akkermansiaceae and Blautia, along with metabolite short-chain fatty acid (SCFA)-mediated upregulation of G protein-coupled receptor 43 (GPR43) to inhibit expression of inflammatory factors. Our collective results strongly supported the fact that the utility of sinapine as a prebiotic agent could prevent gut dysbiosis and obesity-related chronic diseases, such as insulin resistance (IR) and NAFLD.

Title

Sinapine reduces non-alcoholic fatty liver disease in mice by modulating the composition of the gut microbiota.

Author

Li Y 1, Li J , Su Q , Liu Y .

Publish date

2019 Jun 19

PMID

30409660

Abstract

Sinapine is the main secondary metabolite present in rapeseed pomace (RSP) with its concentration being dependent on rapeseed processing, growing conditions, extraction parameters and the country of origin. Here we report, the concentration of sinapine from an extract of defatted RSP harvested in the North East of Scotland. Using liquid chromatography tandem mass spectrometry, the most abundant phenolic compound in the RSP extract was, as expected, sinapine (109.1 mg/g RSP extract). Additionally, sinapic, caffeic, ferulic and syringic acids were identified (0.159-3.91 mg/g RSP extract). Sinapine together with the phenolics at the concentration present in the RSP extract, exhibited ≥50% activity relative to the extract in antioxidant assays. Furthermore, sinapine provided plasmid DNA (pBR322) protection, from 2,2′-azobis(2-amidinopropane) dihydrochloride and inhibited acetylcholinesterase activity by 85%. Molecular docking was utilised to explain the inhibitory activity. RSP can be an excellent source of bioactive compounds for pharmaceuticals, food additive and nutraceutical applications.

Copyright © 2018 Elsevier Ltd. All rights reserved.

KEYWORDS

Acetylcholinesterase (AChE); Antioxidant assays; Canola; LC-MS/MS; Phenolic acids; Plasmid DNA (pBR322); Rapeseed pomace; Sinapine

Title

Determination of sinapine in rapeseed pomace extract: Its antioxidant and acetylcholinesterase inhibition properties.

Author

Yates K1, Pohl F1, Busch M2, Mozer A2, Watters L3, Shiryaev A4, Kong Thoo Lin P5.

Publish date

2019 Mar 15


Description :

Sinapine is an alkaloid from seeds of the cruciferous species which shows favorable biological activities such as antioxidant and radio-protective activities.