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Ergosterol peroxide

$600

  • Brand : BIOFRON

  • Catalogue Number : BN-O1512

  • Specification : 98%(HPLC)

  • CAS number : 2061-64-5

  • Formula : C28H44O3

  • Molecular Weight : 428.7

  • PUBCHEM ID : 5351516

  • Volume : 5mg

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Catalogue Number

BN-O1512

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

428.7

Appearance

Cryst.

Botanical Source

This product is isolated and purified from the herbs of Isodon eriocalyx

Structure Type

Steroids

Category

Standards;Natural Pytochemical;API

SMILES

CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C24C=CC5(C3(CCC(C5)O)C)OO4)C

Synonyms

5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol/Ergosterol peroxide/Peroxyergosterol/(3S,5S,8S,9R,10R,13R,14R,17R)-17-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol/3b,5a-Etheno-1H-benz[c]indeno[5,4-e][1,2]dioxin-7-ol, 2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-9a,11a-dimethyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl]-, (1R,3aR,3bS,5aS,7S,9aR,9bR,11aR)-/Ergosterol endoperoxide/(1S,2R,5R,6R,9R,10R,13S,15S)-5-[(2R,3E,5R)-5,6-Dimethyl-3-hepten-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0.0.0]nonadec-18-en-13-ol/Ergosterol 5.alpha.,8.alpha.-epidioxide/Ergosterol 5.α.,8.α.-epidioxide/ergosterol-5,8-peroxide/5α,8α-Ergosta-6,22-dien-3β-ol, 5,8-epidioxy-

IUPAC Name

(1S,2R,5R,6R,9R,10R,13S,15S)-5-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.01,9.02,6.010,15]nonadec-18-en-13-ol

Density

1.1±0.1 g/cm3

Solubility

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

Flash Point

256.0±28.7 °C

Boiling Point

499.7±45.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1

InChl Key

VXOZCESVZIRHCJ-KGHQQZOUSA-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#:2061-64-5) 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

29149595

Abstract

Vms1 translocates to damaged mitochondria in response to stress, whereupon its binding partner, Cdc48, contributes to mitochondrial protein homeostasis. Mitochondrial targeting of Vms1 is mediated by its conserved mitochondrial targeting domain (MTD), which, in unstressed conditions, is inhibited by intramolecular binding to the Vms1 leucine-rich sequence (LRS). Here, we report a 2.7 a crystal structure of Vms1 that reveals that the LRS lies in a hydrophobic groove in the autoinhibited MTD. We also demonstrate that the oxidized sterol, ergosterol peroxide, is necessary and sufficient for Vms1 localization to mitochondria, through binding the MTD in an interaction that is competitive with binding to the LRS. These data support a model in which stressed mitochondria generate an oxidized sterol receptor that recruits Vms1 to support mitochondrial protein homeostasis.

KEYWORDS

ROS signaling; S. cerevisiae; biochemistry; lipid signaling; liposomes; mitochondrial quality control; oxidative stress; protein degradation; sterols; structure-function.

Title

Sterol Oxidation Mediates Stress-Responsive Vms1 Translocation to Mitochondria

Author

Jason R Nielson 1, Eric K Fredrickson 1, T Cameron Waller 1, Olga Zurita Rendon 2, Heidi L Schubert 1, Zhenjian Lin 3, Christopher P Hill 4, Jared Rutter 5

Publish date

2017 Nov 16

PMID

30560887

Abstract

As part of our ongoing search for novel therapeutic structures from microorganism, the chemical examination of marine fungus Phoma sp. resulted in the isolation of ergosterol, ergosterol peroxide (EP), and 9,11-dehydroergosterol peroxide (DEP). The bioassay results demonstrated that the three isolates reduced the viability of various cancer cells, with EP being highest in human lung cancer cell line A549 cells. EP induced caspase-dependent apoptosis through mitochondrial damage in A549 cells. Additionally, EP-induced ROS generation and apoptosis were attenuated by ROS-generating enzymes inhibitors and antioxidant N-acetylcysteine, indicated that ROS played an important role in EP-mediated apoptosis in A549 cells. Furthermore, it was observed that EP induced ROS-dependent autophagy, which attenuated apoptosis in A549 cells. On the other hand, EP reduced the LPS/ATP-induced proliferation and migration of A549 cells through attenuated NLRP3 inflammasome activity. Additionally, EP showed synergistic cytotoxic effect with antitumor drug Sorafenib in A549 cell viability inhibition. Furthermore, Micro-Western Array and Western blot analyses demonstrated that the protein levels of EGFR, HSP27, MEK5, AKT1, mTOR, Smad2, Smad3, TAB1, NF-κB, and HIF1-α decreased, while the levels of p-p38α, p-ERK1/2, p-JNK, fibronectin and p27 increased. Collectively, the results of this study demonstrated that EP might be useful to develop a therapeutic candidate for lung cancer complications.

Title

Ergosterol Peroxide From Marine Fungus Phoma Sp. Induces ROS-dependent Apoptosis and Autophagy in Human Lung Adenocarcinoma Cells

Author

Han-Ying Wu 1 2 3, Feng-Ling Yang 1, Lan-Hui Li 4, Yerra Koteswara Rao 5, Tz-Chuen Ju 6, Wei-Ting Wong 7, Chih-Yu Hsieh 5, Michael V Pivkin 8, Kuo-Feng Hua 9 10 11, Shih-Hsiung Wu 12

Publish date

2018 Dec 18;

PMID

28436318

Abstract

Ergosterol peroxide (EP; 5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol) is a C28-sterol and a component of many medicinal mushrooms. Since its discovery nearly a century ago, many sources and biological effects of this compound have been described. Effects range from antimicrobial to cytotoxic to immunosuppressive and other activities. This review covers biological investigations of EP, its activities, and possible mechanisms of action. EP is a promising candidate for drug development and contributes to the health-promoting effects of medicinal mushrooms.

Title

Ergosterol Peroxide: A Mushroom-Derived Compound With Promising Biological Activities-A Review

Author

Simon Merdivan 1, Ulrike Lindequist 2

Publish date

2017;


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