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Sinigrin

$178

  • Brand : BIOFRON

  • Catalogue Number : BF-S3005

  • Specification : 98%

  • CAS number : 3952-98-5

  • Formula : C10H16KNO9S2

  • Molecular Weight : 397.46

  • PUBCHEM ID : 23682211

  • Volume : 20mg

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Catalogue Number

BF-S3005

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

397.46

Appearance

White needle crystal

Botanical Source

Sinapis alba

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

C=CCC(=NOS(=O)(=O)[O-])SC1C(C(C(C(O1)CO)O)O)O.[K+]

Synonyms

(−)-Sinigrin hydrate/Allyl glucosinolate/Kalium-[({[(1Z)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]sulfanyl}-3-buten-1-yliden]amino}oxy)sulfonyl]oxidanid/Kalium-1-S-[(1Z)-N-(sulfonatooxy)-3-butenimidoyl]-1-thio-β-D-glucopyranose/Myronate Potassium/1-Thio-b-D-glucopyranose 1-[N-(Sulfooxy)-3-butenimidate] Monopotassium Salt/Potassium Myronate/[({[(1Z)-1-{[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]sulfanyl}-3-buten-1-ylidene]amino}oxy)sulfonyl]oxidanide de potassium/Potassium 1-S-[(1Z)-N-(sulfonatooxy)-3-butenimidoyl]-1-thio-β-D-glucopyranose/Potassium [({[(1Z)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]sulfanyl}-3-buten-1-ylidene]amino}oxy)sulfonyl]oxidanide/Sinigroside/Potassium 1-S-[(1E)-N-(sulfonatooxy)-3-butenimidoyl]-1-thio-β-D-glucopyranose hydrate (1:1:1)/1-S-[(1Z)-N-(Sulfonatooxy)-3-butenan-1-imidoyl]-1-thio-β-D-glucopyranose de potassium/Sinigrin Hydrate/β-D-Glucopyranose, 1-S-[(1E)-1-[(sulfooxy)imino]-3-buten-1-yl]-1-thio-, potassium salt, hydrate (1:1:1)/Sinigrin/Potassium 1-S-[(1Z)-N-(sulfonatooxy)but-3-enimidoyl]-1-thio-β-D-glucopyranose/β-D-Glucopyranose, 1-S-[(1Z)-1-[(sulfooxy)imino]-3-buten-1-yl]-1-thio-, potassium salt (1:1)

IUPAC Name

potassium;[(E)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylbut-3-enylideneamino] sulfate

Density

Solubility

Water

Flash Point

Boiling Point

Melting Point

128 (dec.)(lit.)ºC

InChl

InChl Key

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#:3952-98-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

28483571

Abstract

Atherosclerosis is a complex inflammatory disease associated with elevated levels of atherogenic molecules for leukocyte recruitment. Sinigrin (2-propenylglucosinolate) is found mainly in broccoli, brussels sprouts, and black mustard seeds. Recently, sinigrin has received attention for its role in disease prevention and health promotion. In this study, we examined the effect of sinigrin on development of atherosclerosis in ApoE-/- mice and the expression of adhesion molecules in vascular smooth muscle cells (VSMCs). The serum concentrations of lactate dehydrogenase (LDH), triglyceride (TG), total cholesterol (TC), low density lipoprotein (LDL), calcium (Ca2+), and pro-inflammatory cytokines were reduced by sinigrin treatment in ApoE-/- mice. In addition, oral administration of sinigrin attenuated the mRNA expression of vascular cell adhesion molecule-1 (VCAM-1), intercellular adhesion molecule-1 (ICAM-1), C-C motif chemokine ligand 2 (CCL2), and CCL5 on aorta tissues and 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGR), liver X receptor (LXR), sterol regulatory element-binding protein-2 (SREBP-2), and low density lipoprotein receptor (LDLR) on liver tissues in ApoE-/- mice. To provide a potential mechanism underlying the action of sinigrin, we evaluated the in vitro effect of sinigrin on the expression of the VCAM-1 in TNF-α-induced VSMCs. The increased expression of VCAM-1 by TNF-α stimulation was significantly suppressed by the treatment of sinigrin (1-100 μg/ml) and sinigrin inhibited the nuclear translocation of NF-κB and the phosphorylation of p38 MAPK and JNK pathways, suggesting that sinigrin decreases the TNF-α-stimulated VCAM-1 expression through the suppression of NF-κB and MAP kinases signaling pathways. Overall, sinigrin has the potential to be used in reducing the risks of atherosclerosis.

KEYWORDS

2-Propenyl glucosinolate; ApoE(−/−) mice; Atherosclerosis; MOVAS cells; Sinigrin.

Title

Sinigrin Attenuates the Progression of Atherosclerosis in ApoE -/- Mice Fed a High-Cholesterol Diet Potentially by Inhibiting VCAM-1 Expression

Author

Yeon Jeong Jang 1 , Bongkyun Park 1 , Hee-Weon Lee 1 , Hye Jin Park 1 , Hyun Jung Koo 2 , Byung Oh Kim 3 , Eun-Hwa Sohn 4 , Sung Hee Um 5 , Suhkneung Pyo 6

Publish date

2017 Jun 25

PMID

28219839

Abstract

Sinigrin (2-propenyl glucosinolate) is found mainly in broccoli, brussels sprouts, and black mustard seeds. Recently, sinigrin has received attention for its role in disease prevention and health. This study investigated the effect of sinigrin on macrophage function, including the activity of Nod-like receptor protein 3 (NLRP3) inflammasome. In a concentration-dependent manner, sinigrin inhibited lipopolysaccharide (LPS)-induced nitric oxide (NO) production and the expression of COX-2 and prostaglandin E2 (PGE2) in RAW 264.7 cells. In addition, sinigrin significantly suppressed the production of tumor necrosis factor (TNF)-α and interleukin (IL)-6 via suppression of MAPK phosphorylation and nuclear factor-kappa B (NF-κB) activity. Treatment with sinigrin decreased IL-1β and IL-18 production and concurrently suppressed NLRP3, apoptosis-associated speck-like protein containing a caspase recruitment domain (ASC), and caspase-1 expression in LPS/ATP-stimulated cells, suggesting that the blocking of NLRP3 inflammasome activation prevented the production of both cytokines. Collectively, these results suggest that sinigrin has immunomodulatory effects by suppressing the production of inflammatory mediators, possibly by inhibiting the NF-κB/MAPK pathways or NLRP3 inflammasome activation. Our findings also provide evidence that the pharmacological modulation of sinigrin could have an anti-inflammatory effect.

KEYWORDS

2-Propenyl glucosinolate; ApoE(−/−) mice; Atherosclerosis; MOVAS cells; Sinigrin.

Title

Sinigrin Inhibits Production of Inflammatory Mediators by Suppressing NF-κB/MAPK Pathways or NLRP3 Inflammasome Activation in Macrophages

Author

Hee-Weon Lee 1 , Chung Gi Lee 1 , Dong-Kwon Rhee 1 , Sung Hee Um 2 , Sukneung Pyo 3

Publish date

2017 Apr

PMID

26571343

Abstract

Sinigrin is a major component of cruciferous vegetables such as cabbage, Brussels sprout, mustard greens and broccoli. The present study demonstrates the protective effects of sinigrin against the non-enzymatic glycation of albumin and lens crystallin based on fluorescence spectroscopy, circular dichroism and molecular interaction studies. Sinigrin was found to be a potent inhibitor for both the early (Amadori product) and advanced glycation end products (AGEs). In addition, the in vitro glycation studies of lens crystallin demonstrated the strong antiglycation activity of sinigrin. Computational studies using molecular docking approach revealed the interaction pattern of sinigrin with BSA and the binding affinity of sinigrin was found to be greater than the other potent natural inhibitors of glycation such as quercetin, apigenin, and curcumin.

KEYWORDS

Advanced glycation end products; Albumin; Sinigrin.

Title

Sinigrin, a Major Glucosinolate From Cruciferous Vegetables Restrains Non-Enzymatic Glycation of Albumin

Author

Saurabh Awasthi 1 , N T Saraswathi 2

Publish date

2016 Feb


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