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Embelin

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-E2005

  • Specification : 98%

  • CAS number : 550-24-3

  • Formula : C17H26O4

  • Molecular Weight : 294.39

  • PUBCHEM ID : 3218

  • Volume : 20mg

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Catalogue Number

BF-E2005

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

294.39

Appearance

White crystalline powder

Botanical Source

Embelia laeta

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O

Synonyms

2,5-Dihydroxy-3-undecyl-1,4-benzoquinone/Embelin/2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione/2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-undecyl-

IUPAC Name

2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione

Density

1.131

Solubility

Methanol; Chloroform; DMSO

Flash Point

229.1±25.2 °C

Boiling Point

431.9±45.0 °C at 760 mmHg

Melting Point

145-146 ºC

InChl

InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3

InChl Key

IRSFLDGTOHBADP-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2914690000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:550-24-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31545222

Abstract

BACKGROUND/AIMS:
Embelin is an active component isolated from Embelia ribes Burm. In this study, we explored the protective effects of embelin on acute liver injury.

METHODS:
An animal model of acute liver injury was established via administration of a single injection of thioacetamide (TAA) (300 μg/g body weight) to adult mice. Embelin was administered by intragastric gavage at 50 μg/g body weight starting 2 days before TAA administration and continuing throughout the study. Survival of the mice was analyzed by the Kaplan-Meier method using the log-rank test. The acute liver injury protocol was repeated and the remaining mice were analyzed at indicated times. Hematoxylin and eosin staining and picrosirius red staining were used to examine necrosis/inflammation and liver healing, respectively. Liver function was assessed by serum alanine aminotransferase/alkaline phosphatase activity. Hepatic cleaved caspase-3 and F4/80 expression levels were examined via immunostaining. Statistical analysis was performed with GraphPad Software.

RESULTS:
The survival and liver function of the mice were markedly better in the group treated with embelin prior to TAA toxication than in the TAA toxication-only group. Embelin significantly reduced TAA-induced hepatic necrosis/apoptosis. Massive inflammatory cell infiltration, which is consistent with hepatic fibrogenesis (a healing process), occurred earlier in the embelin-treated recovery group than in the spontaneous recovery group. Moreover, macrophage activities increased more rapidly with embelin treatment.

CONCLUSIONS:
In summary, embelin can protect against acute liver injury. Its therapeutic value warrants further exploration.

Copyright © 2019 The Authors. Published by Elsevier Masson SAS.. All rights reserved.

KEYWORDS

Acute liver injury; Embelin; Healing reaction; Survival

Title

Embelin can protect mice from thioacetamide-induced acute liver injury.

Author

Wang H1, Zhang H2, Wang Y3, Yang L4, Wang D5.

Publish date

2019 Oct;

PMID

31115498

Abstract

Malignant rhabdoid tumour (MRT) is a rare, aggressive paediatric neoplasm, primarily diagnosed in those below the age of three. MRTs most commonly arise in the central nervous system and kidneys. A poor prognosis accompanies the MRT diagnosis, with a reported 2‑year survival rate of 30%. Thus, there is an urgent need for the development of new therapies for this malignancy. Members of the inhibitor of apoptosis protein (IAP) family have previously been reported to be overexpressed in various cancers. As such, small molecule inhibitors of these family members have entered clinical trials. However, the role of IAPs in MRT has not been examined yet. The present study is the first report of the expression of a range of IAPs, including X‑linked inhibitor of apoptosis (XIAP), cellular inhibitor of apoptosis protein 1 (cIAP1), cellular inhibitor of apoptosis protein 2 (cIAP2), livin and survivin in MRT cell lines. Furthermore, the results demonstrated the ability of the XIAP inhibitor, embelin, to sensitise MRT cell lines to TNF‑related apoptosis‑inducing ligand (TRAIL) treatment. The enhanced cell death detected upon cotreatment was dependent on caspase‑8 and co‑occurred with caspase‑8 and caspase‑3 cleavage, suggesting engagement of the extrinsic apoptotic pathway. Sensitisation to TRAIL was accompanied by livin cleavage, alongside downregulation of survivin and the caspase‑8 inhibitor FLIPL. In addition, knockdown of XIAP using siRNA enhanced TRAIL‑mediated cell death, suggesting that this process may in part mediate sensitisation. In conclusion, the present results suggested that IAP inhibition may present a novel avenue for the treatment of MRT.

Title

The XIAP inhibitor embelin sensitises malignant rhabdoid tumour cells to TRAIL treatment via enhanced activation of the extrinsic apoptotic pathway.

Author

Coyle R1, Slattery K2, Ennis L2, O'sullivan MJ3, Zisterer DM2.

Publish date

2019 Ju

PMID

31050027

Abstract

Beta-secreatse (BACE-1) and cholinesterases are clinically validated targets of Alzheimer’s disease (AD), for which natural products have provided immense contribution. The multifaceted nature of AD signifies the need of multitargeted agents to tackle this disease. In the search of new natural products as dual BACE-1/cholinesterase inhibitors, a library of pure natural products was screened for inhibition of acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and BACE-1. The screening efforts have identified 1,4-benzoquinone “embelin,” a natural product derived from Embelia ribes displaying inhibition of all three enzymes, with IC50 values of 2.5, 5.4, and 2.1 μM, respectively. This screen has also identified isoquinoline alkaloids papaverine and L-tetrahydropalmatine as AChE inhibitors. Kinetic study has shown that embelin inhibits EeAChE and EqBChE with ki values of 4.59 and 0.57 μM, in an uncompetitive and noncompetitive manner, respectively. The interactions of embelin with allosteric peripheral anionic site of cholinesterases, has further supported the results of kinetic study. Embelin has also enhanced the activity of P-gp in LS-180 cells, the efflux pump which is involved in the clearance of amyloid-β from AD brain. Further, the cell viability study in neuronal cell line has indicated the excellent therapeutic window of embelin. These results are indicative of the fact that embelin is a multitargeted agent playing role in stopping the formation of amyloid-β oligomers (via inhibition of BACE-1), improves cholinergic-transmission (via inhibition of AChE/BChE) and increases amyloid-β clearance (via P-gp induction).

© 2019 Wiley Periodicals, Inc.

KEYWORDS

Alzheimer's disease; BACE-1; L-tetrahydropalmatine; acetylcholinesterase; butyrylcholinesterase; embelin; papaverine

Title

Identification of embelin, a 3-undecyl-1,4-benzoquinone from Embelia ribes as a multitargeted anti-Alzheimer agent.

Author

Nuthakki VK1, Sharma A2, Kumar A2, Bharate SB1.

Publish date

2019 Aug


Description :

Embelin is a cell-permeable benzoquinone compound that exhibits antitumor properties. Specifically antagonizes XIAP-mediated inhibition of caspase-9 activation by directly targeting the Smac and caspase-9 binding domain BIR3 (IC50 = 4.1 uM in a competitive binding assay with Smac peptide).IC50 value: 4.1 uM [1]Target: XIAPin vitro: Embelin induced activation of caspase-9 and embelin-induced apoptosis was prevented by caspase inhibitors [2]. Treatment with subtoxic doses of Embelin broadly sensitized malignant glioma cells to TRAIL-mediated apoptosis. Notably, human astrocytes were not significantly affected by the combined treatment consisting of Embelin and TRAIL. Combined treatment with Embelin and TRAIL augmented the activation of initiator caspases-8/-9 and effector caspases-3/-7, respectively [3]. in vivo: Embelin inhibited topical edema in the mouse ear, leading to substantial reductions in skin thickness and tissue weight, inflammatory cytokine production, neutrophil-mediated myeloperoxidase activity, and various histopathological indicators. Furthermore, embelin was effective at reducing inflammatory damage induced by chronic TPA exposure [4]. Embelin (10, 30 or 50mg/kg body weight) was administrated daily per oral route for 7days. Embelin significantly attenuated DSS-induced DAI scores and tissue MPO accumulation, which implied that it suppressed weight loss, diarrhea, gross bleeding, and the infiltrations of immune cells. Embelin administration also effectively and dose-dependently prevented shortening of colon length and enlargement of spleen size [5].