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Apo-12’-lycopenal

$640

  • Brand : BIOFRON

  • Catalogue Number : BN-O1438

  • Specification : 95%(HPLC)

  • CAS number : 1071-52-9

  • Formula : C25H34O

  • Molecular Weight : 350.5

  • PUBCHEM ID : 10904256

  • Volume : 5mg

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Catalogue Number

BN-O1438

Analysis Method

Specification

95%(HPLC)

Storage

2-8°C

Molecular Weight

350.5

Appearance

Botanical Source

Structure Type

Category

SMILES

CC(=CCCC(=CC=CC(=CC=CC(=CC=CC=C(C)C=O)C)C)C)C

Synonyms

Apo-12’-lycopenal/.12'-Apo-/Apo-12'-lycopenal/2,4,6,8,10,12,14,18-Eicosaoctaenal, 2,7,11,15,19-pentamethyl-, (2E,4E,6E,8E,10E,12E,14E)-/.apo-12'-lycopenal/(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-Pentamethyl-2,4,6,8,10,12,14,18-icosaoctaenal

IUPAC Name

(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal

Density

0.9±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

243.2±13.8 °C

Boiling Point

506.7±19.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

CTKROHWZDNWNMY-MSWJQUEKSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:1071-52-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30449105

Abstract

Apo-lycopenals, lycopene metabolites produced by an initial cleavage by β,β-carotene-9′,10′-oxygenase, exhibit diverse biologically active effects. In this study, we investigated the effect of apo-lycopenals on the activation of nuclear receptors involved in glucose and lipid metabolism. Only apo-12′-lycopenal exhibited selective and dose-dependent transactivation activity for peroxisome proliferator-activated receptor γ (PPARγ), whereas neither apo-6′- nor apo-8′-lycopenals displayed this activity ((7.83 ± 0.66)-, (1.32 ± 0.10)-, and (1.31 ± 0.37)-fold higher activity relative to control, respectively). Additionally, apo-12′-lycopenal promoted adipocyte differentiation of 3T3-L1 cells and subsequently increased the mRNA levels of PPARγ (a (2.36 ± 0.07)-fold increase relative to control; p < 0.01) and its target genes, as well as enhanced adiponectin secretion (a (3.25 ± 0.27)-fold increase relative to control; p < 0.01) and insulin-stimulated glucose uptake (1486 ± 85 pmol/well; p < 0.001) in 3T3-L1 cells. Our results indicated that apo-12'-lycopenal promoted adipocyte differentiation by direct binding and activation of PPARγ.

KEYWORDS

PPARγ; adipocyte differentiation; apo-12′-lycopenal; glucose uptake; lycopene metabolites

Title

Apo-12'-lycopenal, a Lycopene Metabolite, Promotes Adipocyte Differentiation via Peroxisome Proliferator-Activated Receptor γ Activation.

Author

Takahashi S1, Waki N1, Mohri S2, Takahashi H2, Ara T2, Aizawa K1, Suganuma H1, Kawada T2, Goto T2.

Publish date

2018 Dec 19

PMID

16702320

Abstract

The health benefits of lycopene as an anticarcinogenic compound have been widely studied but little is known about the metabolic products of lycopene produced in vivo. We investigated lycopene metabolites in the liver of F344 male rats that had been prefed a lycopene-containing diet (0.25 g lycopene/kg diet). After 30 d of feeding, they were given a single oral dose of 14C-labeled lycopene (421.8 kBq). The metabolic products of both nonradioactive and 14C-labeled lycopene in rat liver were extracted and separated using HPLC and analyzed by UV/VIS spectrometry, online radioactive detection, and off-line and in-line positive ion electrospray ionization MS. Among a number of metabolite products formed, we identified apo-8′-lycopenal (lambdamax = 473 nm and m/z = 417). The putative compound, apo-12′-lycopenal, was detected but no apo-10′-lycopenal was present. A number of other very polar, short-chain and/or short chromophore compounds with UV/VIS absorption <300 nm were present but were not characterized. These data show that lycopene is cleaved in vivo by rats at different positions to produce apo-12'-lycopenal, and other unidentified metabolites in addition to apo-8'-lycopenal. Apo-8'-lycopenal and the putative apo-12'-lycopenal are identified as lycopene metabolites in rat liver in vivo.

Title

Apo-8'-lycopenal and apo-12'-lycopenal are metabolic products of lycopene in rat liver.

Author

Gajic M1, Zaripheh S, Sun F, Erdman JW Jr.

Publish date

2006 Jun

PMID

21207319

Abstract

Lycopene is associated with a reduced risk of prostate cancer. However, lycopene may not be wholly responsible for the effects seen in vivo or in cell culture systems. Apo-lycopenals or other lycopene metabolites, whether produced by cleavage enzymes within the body or consumed with tomato products, can be found in tissues at concentrations equivalent to physiological retinoid concentrations. Therefore, it is plausible that lycopenoids, like retinoids, are bioactive within tissues. Androgen-independent DU145 prostate cancer cells were treated with lycopene, apo-8′-lycopenal, or apo-12′-lycopenal. DU145 cell proliferation was significantly reduced by supra-physiological levels of lycopene and apo-12′-lycopenal, in part, through alteration of the normal cell cycle. Levels of the gap junction protein, connexin 43, were unaltered by lycopene or apo-lycopenal treatment while cell apoptosis rates significantly decreased. We further confirmed that connexin 43 protein levels were unaltered by lycopene treatment in mouse embryonic fibroblasts, or in Dunning R3327-H rat prostate tumor. The present data indicate that lycopene and apo-12′-lycopenal reduce the proliferation of prostate cancer cells, in part, by inhibiting normal cell cycle progression.

Copyright © 2011, Taylor & Francis Group, LLC

Title

Lycopene and apo-12'-lycopenal reduce cell proliferation and alter cell cycle progression in human prostate cancer cells.

Author

Ford NA1, Elsen AC, Zuniga K, Lindshield BL, Erdman JW Jr.

Publish date

2011


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