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Pinosylvin

$250

  • Brand : BIOFRON

  • Catalogue Number : BF-P3005

  • Specification : 98%

  • CAS number : 22139-77-1

  • Formula : C14H12O2

  • Molecular Weight : 212.24

  • PUBCHEM ID : 5280457

  • Volume : 25mg

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Catalogue Number

BF-P3005

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

212.24

Appearance

Off-white crystalline powder

Botanical Source

Pinus tabuliformis

Structure Type

Stilbenes

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC=C(C=C1)C=CC2=CC(=CC(=C2)O)O

Synonyms

3,5-dihydroxystilbene/E-3,5-Stilbenediol/5-Styrylresorcinol/3,5-TRANS-DIHYDROXYSTILBENE/5-[(E)-2-Phenylvinyl]-1,3-benzenediol/Pisylvin/1,3-Benzenediol, 5-(2-phenylethenyl)-/5-[(E)-2-Phenylethenyl]-1,3-benzenediol/5-[(E)-2-phenylethenyl]benzene-1,3-diol/5-[(E)-2-Phenylvinyl]benzene-1,3-diol/trans-3,5-Dihydroxystilbene/5-(2-phenylethenyl)benzene-1,3-diol/(trans)-3,5-stilbenediol/5-(2-phenylvinyl)benzene-1,3-diol/5-(2-phenylethenyl)-1,3-benzenediol/1,3-Benzenediol, 5-[(E)-2-phenylethenyl]-/Pinosylvin

IUPAC Name

5-[(E)-2-phenylethenyl]benzene-1,3-diol

Density

1.3±0.1 g/cm3

Solubility

Methanol; Chloroform

Flash Point

194.9±15.5 °C

Boiling Point

397.6±17.0 °C at 760 mmHg

Melting Point

155.5-156°

InChl

InChI=1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+

InChl Key

YCVPRTHEGLPYPB-VOTSOKGWSA-N

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#:22139-77-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30027566

Abstract

Resveratrol at high concentrations (50-100 μmol/L) is known to induce cell death in leukemia cells. Here, we investigated whether pinosylvin, a resveratrol analogue, induced cell death in leukemia cells. Cell death was found to be markedly elevated by 50- to 100-μmol/L pinosylvin in THP-1 and U937 cells. It was also shown that pinosylvin induced caspase-3 activation, flip-flop of phosphatidylserine, LC3-II accumulation, LC3 puncta, and p62 degradation in both THP-1 and U937 cells. These data indicate that pinosylvin-induced cell death may occur through apoptosis and autophagy. In addition, we showed that pinosylvin down-regulates AMP-activated protein kinase α1 (AMPKα1) in leukemia cells. Therefore, we correlated AMPKα1 down-regulation and leukemia cell death. AMPKα1 inhibition appeared to decrease pinosylvin-induced apoptosis and autophagy in leukemia cells, implying that AMPK is a key regulator of leukemia cell death. Moreover, we found that both pinosylvin-induced autophagy and apoptotic progress were reduced in AMPKα1-overexpressed leukemia cells, when compared with vector-transfected cells. Cell death was elevated by AMPKα1 overexpression, whereas pinosylvin-induced cell death was markedly decreased by caspase-3 inhibitors or autophagy inhibitors. These results suggest that pinosylvin-induced depletion of AMPKα1 enhances cell death via apoptosis and autophagy in leukemia cells.

KEYWORDS

AMPK; LC3; apoptosis; autophagy; pinosylvi

Title

Pinosylvin Enhances Leukemia Cell Death via Down-Regulation of AMPKα Expression

Author

Jina Song 1 , Youngsik Seo 1 , Heonyong Park 1

Publish date

2018 Oct

PMID

29555013

Abstract

Pinosylvin is known to have anti-inflammatory activity in endothelial cells. In this study, we found that pinosylvin had a pro-apoptotic activity in lipopolysaccharide (LPS)-preconditioned leukocytes. This finding suggests that pinosylvin has an effect on the resolution of inflammation. To understand the detailed mechanism, we examined if pinosylvin enhances cyclooxygenase (COX) or lipoxygenase (LOX) activity in THP-1 and U937 cells. LOX activity was found to be markedly increased by pinosylvin, whereas COX activity was not altered. Furthermore, we found that pinosylvin enhanced both levels of ALOX 15 mRNA and protein, implying that LOX activity, elevated by pinosylvin, is attributed to upregulation of ALOX 15 expression. From this cell signaling study, pinosylvin appeared to promote phosphorylations of ERK and JNK. ERK or JNK inhibitors were found to attenuate ALOX 15 expression and LPS-induced apoptosis promoted by pinosylvin. In conclusion, pinosylvin enhances the apoptosis of LPSpreconditioned leukocytes by up-regulating ALOX 15 expression through ERK and JNK. These findings suggest that pinosylvin may induce the resolution of inflammation. [BMB Reports 2018; 51(6): 302-307].

KEYWORDS

AMPK; LC3; apoptosis; autophagy; pinosylvi

Title

Pinosylvin Exacerbates LPS-induced Apoptosis via ALOX 15 Upregulation in Leukocytes

Author

Ohseong Kwon 1 , Youngsik Seo 1 , Heonyong Park 1

Publish date

2018 Jun

PMID

27116968

Abstract

Pinosylvin as a bioactive stilbene is of great interest for food supplements and pharmaceuticals development. In comparison to conventional extraction of pinosylvin from plant sources, biosynthesis engineering of microbial cell factories is a sustainable and flexible alternative method. Current synthetic strategies often require expensive phenylpropanoic precursor and inducer, which are not available for large-scale fermentation process. In this study, three bioengineering strategies were described to the development of a simple and economical process for pinosylvin biosynthesis in Escherichia coli. Firstly, we evaluated different construct environments to give a highly efficient constitutive system for enzymes of pinosylvin pathway expression: 4-coumarate: coenzyme A ligase (4CL) and stilbene synthase (STS). Secondly, malonyl coenzyme A (malonyl-CoA) is a key precursor of pinosylvin bioproduction and at low level in E. coli cell. Thus clustered regularly interspaced short palindromic repeats interference (CRISPRi) was explored to inactivate malonyl-CoA consumption pathway to increase its availability. The resulting pinosylvin content in engineered E. coli was obtained a 1.9-fold increase depending on the repression of fabD (encoding malonyl-CoA-ACP transacylase) gene. Eventually, a phenylalanine over-producing E. coli consisting phenylalanine ammonia lyase was introduced to produce the precursor of pinosylvin, trans-cinnamic acid, the crude extraction of cultural medium was used as supplementation for pinosylvin bioproduction. Using these combinatorial processes, 47.49 mg/L pinosylvin was produced from glycerol.

KEYWORDS

Biosynthesis; CRISPRi; Combinatorial bioengineering; Pinosylvin.

Title

A Novel Process for Obtaining Pinosylvin Using Combinatorial Bioengineering in Escherichia Coli

Author

Jing-Long Liang 1 2 , Li-Qiong Guo 1 2 , Jun-Fang Lin 3 4 , Ze-Qi He 1 , Fa-Ji Cai 1 , Jun-Fei Chen 5

Publish date

2016 Jun


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