ERGOSTEROL ENDOPEROXIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H44O3
Molecular Weight	428.6472
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(CC[C@]2([H])[C@]1(C)CC[C@]3([H])[C@@]4(C)CC[C@H](O)C[C@@]45OO[C@@]23C=C5)[C@H](C)\C=C\[C@H](C)C(C)C

InChI

InChIKey=VXOZCESVZIRHCJ-KGHQQZOUSA-N

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

HIDE SMILES / InChI

Molecular Formula	C28H44O3
Molecular Weight	428.6472
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22083593 | https://www.ncbi.nlm.nih.gov/pubmed/28436318 | https://www.ncbi.nlm.nih.gov/pubmed/10630115

Ergosterol endoperoxide is a derivative of ergosterol. It has been isolated from a variety of fungi, yeast, lichens and sponges. Ergosterol endoperoxide has been shown to inhibit the growth of some cancer cells and to induce apoptosis of HL60 human leukemia cells. Ergosterol endoperoxide also decreases lipid peroxidation of rat liver microsomes and suppresses the proliferation of mouse and human lymphocytes stimulated with mitogens. It has been reported as having immunosuppressive, antiplasmodial, antimycobacterial, antiviral, anti-inflammatory and antitumoural properties. The interaction of Trypanosoma cruzi with ergosterol peroxide in vitro resulted in a strong lytic activity possibly due to the disruption of the parasite membrane.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-catenin pathway 1 Target ID: Beta-catenin pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/28761355 \| https://www.ncbi.nlm.nih.gov/pubmed/26210065	Inhibitor 8297
STAT3 signaling pathway 2 Target ID: STAT3 signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/28761355	Inhibitor 8297
JAK2 signaling pathway 1 Target ID: JAK2 signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/22260501	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Trypanosomiasis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22083593	Curative	Basic research	Unknown Approved Use Unknown
Ovarian cancer 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28761355	Primary	Basic research	Unknown Approved Use Unknown
Multiple myeloma 159 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22260501	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
ISOLATION OF ERGOSTEROL PEROXIDE FROM TRICHOPHYTON SCHOENLEINI.	1964 Jun 20	14217516
[Microbiological isomerization of ergosterol peroxide].	1969	5800491
[The antiviral action of ergosterol peroxide].	1989 Aug	2594833
Ergosterol peroxide, an active compound from Inonotus radiatus.	1989 Aug	2813575
Antimycobacterial ergosterol-5,8-endoperoxide from Ajuga remota.	1999 Dec	10630115
The antiplasmodial activity of isolates from Ajuga remota.	2002 May	12027771
Antitumor components from Naematoloma fasciculare.	2009 Oct	19884770
Inhibition of STAT3 signaling and induction of SHP1 mediate antiangiogenic and antitumor activities of ergosterol peroxide in U266 multiple myeloma cells.	2012 Jan 20	22260501
Trypanocidal activity of ergosterol peroxide from Pleurotus ostreatus.	2012 Jun	22083593
Ergosterol peroxide from Chaga mushroom (Inonotus obliquus) exhibits anti-cancer activity by down-regulation of the β-catenin pathway in colorectal cancer.	2015 Sep 15	26210065
Ergosterol peroxide activates Foxo3-mediated cell death signaling by inhibiting AKT and c-Myc in human hepatocellular carcinoma cells.	2016 Jun 7	27058618
Ergosterol peroxide inhibits ovarian cancer cell growth through multiple pathways.	2017	28761355
Ergosterol Peroxide: A Mushroom-Derived Compound with Promising Biological Activities-A Review.	2017	28436318

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 100 mg/Kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Ergosterol endoperoxide from Ajuga remota showed a minimum inhibitory concentration (MIC) of 1 ug/ml against Mycobacterium tuberculosis.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 20:13:17 GMT 2023` Edited by `admin` on `Sat Dec 16 20:13:17 GMT 2023`
Record UNII	UG9TN81TGH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ERGOSTEROL ENDOPEROXIDE

Official Name

English

ERGOSTEROL PEROXIDE

Brand Name

English

ERGOSTEROL ENDOPEROXIDE [INCI]

Common Name

English

(22E)-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIEN-3.BETA.-OL

Common Name

English

3.BETA.-HYDROXY-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIENE

Common Name

English

(24R)-ERGOST-5.ALPHA.,8.ALPHA.-EPIDIOXY-6,22-DIEN-3.BETA.-OL

Common Name

English

(22E,24R)-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIEN-3.BETA.-OL

Common Name

English

ERGOSTEROL 5,8-PEROXIDE

Common Name

English

5.ALPHA.,8.ALPHA.-ERGOSTA-6,22-DIEN-3.BETA.-OL, 5,8-EPIDIOXY-

Common Name

English

5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTEROL

Common Name

English

NSC-31324

Code

English

5.ALPHA.,8.ALPHA.-EPIDOXY-(22E,24R)-ERGOSTA-6,22-DIEN-3.BETA.-OL

Common Name

English

PEROXYERGOSTEROL

Common Name

English

ERGOSTERYL PEROXIDE

Common Name

English

ERGOSTA-6,22-DIEN-3-OL, 5,8-EPIDIOXY-, (3.BETA.,5.ALPHA.,8.ALPHA.,22E)-

Common Name

English

Code System Code Type Description

NSC

31324