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Ikshusterol

$1,024

  • Brand : BIOFRON

  • Catalogue Number : BN-O1561

  • Specification : 98%(HPLC)

  • CAS number : 34427-61-7

  • Formula : C29H50O2

  • Molecular Weight : 430.7

  • PUBCHEM ID : 161816

  • Volume : 5mg

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Catalogue Number

BN-O1561

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

430.7

Appearance

Powder

Botanical Source

This product is isolated and purified from the herbs of Lycopodium obscurum Linn.

Structure Type

Steroids

Category

Standards;Natural Pytochemical;API

SMILES

CCC(CCC(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)C)C(C)C

Synonyms

stigmast-5-ene-3,7-diol, (3β,7α,8ξ)-/Ikshusterol/(3β,7α,8ξ)-stigmast-5-ene-3,7-diol/(3β,7α)-Stigmast-5-ene-3,7-diol/Stigmast-5-ene-3,7-diol, (3β,7α)-/stigmast-5-ene-3beta,7alpha-diol

IUPAC Name

(3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol

Density

1.0±0.1 g/cm3

Solubility

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

Flash Point

218.2±21.4 °C

Boiling Point

535.0±38.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C29H50O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h17-20,22-27,30-31H,7-16H2,1-6H3/t19-,20-,22+,23-,24+,25+,26-,27+,28+,29-/m1/s1

InChl Key

SXJVFYZNUGGHRG-GDDJFQTCSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:34427-61-7) 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

25765595

Abstract

Objectives: The aim of our study was to investigate vascular effects of oxysterols and oxyphytosterols on reactive oxygen species (ROS), endothelial progenitor cells, endothelial function and atherogenesis.

Methods: Male apoE-/-mice were treated with cholesterol, sitosterol, 7-ß-OH-cholesterol, 7-ß-OH-sitosterol, or cyclodextrin by daily intraperitoneal application. The respective concentrations in the plasma and in the arterial wall were determined by gas chromatography-flame ionization or mass spectrometry. ROS production was assessed by electron-spin resonance spectroscopy in the aorta, endothelial function of aortic rings and atherosclerosis in the aortic sinus was quantitated after 4 weeks.

Results: Compared to vehicle, there was no difference in plasma cholesterol levels and arterial wall concentrations after i.p. application of cholesterol. 7-ß-OH-cholesterol concentrations were increased in the plasma (33.7±31.5 vs. 574.57.2±244.92 ng/ml) but not in the arterial wall (60.1±60.1 vs. 59.3±18.2 ng/mg). Sitosterol (3.39±0.96 vs. 8.16±4.11 mg/dL; 0.08±0.04 vs. 0.16±0.07 μg/mg, respectively) and 7-ß-OH-sitosterol concentrations (405.1±151.8 vs. 7497±3223 ng/ml; 0.24±0.13 vs. 16.82±11.58 ng/mg, respectively) increased in the plasma and in the aorta. The i.p-application of the non-oxidized cholesterol or sitosterol did not induce an increase of plasma oxysterols or oxyphytosterols concentrations. Oxidative stress in the aorta was increased in 7-ß-OH-sitosterol treated mice, but not in mice treated with cholesterol, sitosterol, or 7-ß-OH-cholesterol. Moreover, cholesterol, sitosterol, 7-ß-OH-cholesterol, and 7-ß-OH-sitosterol did not affect endothelial-dependent vasodilation, or early atherosclerosis.

Conclusion: Increased oxyphytosterol concentrations in plasma and arterial wall were associated with increased ROS production in aortic tissue, but did not affect endothelial progenitor cells, endothelial function, or early atherosclerosis.

KEYWORDS

Atherosclerosis; Endothelial function; Oxyphytosterols; Oxysterols; Phytosterols; Sterols.

Title

Vascular Effects of Oxysterols and Oxyphytosterols in apoE -/- Mice

Author

Oliver Weingartner 1, Constanze Husche 2, Hans F Schott 2, Timo Speer 3, Michael Bohm 4, Charlotte M Miller 5, Florence McCarthy 5, Jogchum Plat 6, Dieter Lutjohann 2, Ulrich Laufs 4

Publish date

2015 May

PMID

27132025

Abstract

The most common phytosterols in the human diet are sitosterol and campesterol, which originate exclusively from plant derived food. These phytosterols are taken up by NPC1L1 transport from the intestine into the enterocytes together with cholesterol and other xenosterols. Phytosterols are selectively pumped back from the enterocytes into the intestinal lumen and on the liver site from hepatocytes into bile by heterodimeric ABCG5/G8 transporters. Like cholesterol, both phytosterols are prone to ring and side chain oxidation. It could be shown that oxyphytosterols, found in atherosclerotic tissue, are most likely of in situ oxidation (Schott et al.; Biochem. Biophys. Res. Commun. 2014 Apr 11;446(3):805-10). However, up to now, the entire mechanism of phytosterol oxidation is not clearly understood. Here, we provide further information about the oxidation of sitosterol and the transport of its oxidation products out of tissue. Our survey includes data of 104 severe aortic stenosis patients that underwent an elective aortic valve cusp replacement. We studied their phytosterol concentrations, as well as absolute and substrate corrected oxyphytosterol levels in plasma and valve cusp tissue. In addition, we also examined phytosterol and oxyphytosterol concentrations in plasma and tissues (from brain and liver) of 10 male ApoE knockout mice. The ratio of 7-oxygenated-sitosterol-to-sitosterol exceeds the ratio for 7-oxygenated-campesterol-to-campesterol in plasma and tissue of both humans and mice. This finding indicates that sitosterol is oxidized to a higher amount than campesterol and that a selective oxidative mechanism might exist which can differentiate between certain phytosterols. Secondly, the concentrations of oxyphytosterols found in plasma and tissue support the idea that oxysitosterols are preferably transported out of individual tissues. Selective oxidation of sitosterol and preferred transport of sitosterol oxidation products out of tissue seem to be a metabolic pathway of forced sitosterol clearance from tissue compartments.

KEYWORDS

Metabolism; Oxidation; Oxyphytosterol; Phytosterol; Sitosterol; Transport

Title

Oxidation of Sitosterol and Transport of Its 7-oxygenated Products From Different Tissues in Humans and ApoE Knockout Mice

Author

Hans-Frieder Schott 1, Sabine Baumgartner 2, Constanze Husche 3, Alexandra Luister 4, Silvia Friedrichs 3, Charlotte M Miller 5, Florence O McCarthy 5, Jogchum Plat 2, Ulrich Laufs 4, Oliver Weingartner 6, Dieter Lutjohann 7

Publish date

2017 May

PMID

25795151

Abstract

In this study, we compare the distribution of intraperitoneally injected sitosterol, 7β-hydroxysitosterol or vehicle only (control) for 28days in male ApoE-/- mice. Furthermore we examine its impact on surrogate markers of cholesterol biosynthesis and sterol absorption rate in plasma, brain and liver tissues from these animals. Injection of sitosterol revealed a 32.1% (P=0.013) lower plasma total cholesterol compared with control. Cholesterol corrected plasma and absolute brain and liver levels of sitosterol are 4.1-, 1.7-, and 7.2-fold (P<0.001 for all) higher, respectively. This is in accordance with a reduced plasma campesterol to cholesterol ratio (-16.2%; P=0.018) together with a 24.1% (P=0.047) lower concentration of hepatic lathosterol. After injection of 7β-hydroxysitosterol the concentrations of 7β-hydroxysitosterol in plasma, brain and liver are 21.0-, 65.8- and 42.7-fold (P<0.001 for all) higher, respectively, compared with control. Injection of 7β-hydroxysitosterol revealed significantly lower plasma cholesterol corrected cholestanol and campesterol (-44.2%; P=0.001 and -24.5; P=0.004) as well as lower absolute liver cholestanol levels (-31.9%; P<0.001) compared with control. Intraperitoneally injected sitosterol and 7β-hydroxysitosterol differently influence cholesterol metabolism in plasma and liver. We conclude that the polar 7β-hydroxysitosterol compound can pass the blood brain barrier with higher efficacy than its substrate, sitosterol. Though present in higher amounts in the brain, both, sitosterol and 7β-hydroxysitosterol do not influence cholesterol metabolism in the brain as proven by our surrogate markers.

KEYWORDS

ApoE−/− mice; Brain oxyphytosterols; Oxysterols; Phytosterols; Plant sterols; Sitosterol.

Title

7β-Hydroxysitosterol Crosses the Blood-Brain Barrier More Favored Than Its Substrate Sitosterol in ApoE-/- Mice

Author

Hans-Frieder Schott 1, Constanze Husche 1, Silvia Friedrichs 1, Charlotte M Miller 2, Florence O McCarthy 2, Ulrich Laufs 3, Jogchum Plat 4, Oliver Weingartner 5, Dieter Lutjohann 6

Publish date

2015 Jul;


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