SINENSETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H20O7
Molecular Weight	372.3686
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1OC)C2=CC(=O)C3=C(O2)C=C(OC)C(OC)=C3OC

InChI

InChIKey=LKMNXYDUQXAUCZ-UHFFFAOYSA-N

InChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23039079 | https://www.ncbi.nlm.nih.gov/pubmed/22516932

Sinensetin is a methylated flavone found in certain citrus fruits. pocess potent antiangiogenesis and anti-inflammatory, sinensetin enhances adipogenesis and lipolysis. Sinensetin is a selective inhibitor of α-glucosidase with IC50 value of 0.66 mg/ml. Alpha-glucosidase and α-amylase inhibition could the mechanisms through which sinensetin exert its antidiabetic activity, indicating that it could have potential use in the management of non-insulin-dependent diabetes. Sinensetin inhibits inflammatory gene expression and STAT1 activation. It has meaningful anti-inflammatory properties which may be utilized in the development of novel anti-inflammatory treatments.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25442272	Inhibitor 8297	40.2 µM [IC50]
alpha-glucosidase activity 2 Target ID: GO:0090599 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23039079	Inhibitor 8297
alpha-amylase activity 1 Target ID: GO:0004556 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23039079	Inhibitor 8297
Arachidonate 15-lipoxygenase 6 Target ID: CHEMBL2903 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11087521	Inhibitor 8297	74.0 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL4321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22516932	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23039079	Primary		Basic research	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22516932	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Immunotoxicity of a standardized citrus polymethoxylated flavone extract.	2001 Nov	11527568
Genetic toxicity of a standardized mixture of citrus polymethoxylated flavones.	2002 May	11955667
Changes in the levels of polymethoxyflavones and flavanones as part of the defense mechanism of Citrus sinensis (cv. Valencia Late) fruits against Phytophthora citrophthora.	2004 Apr 7	15053528
Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities.	2005 Dec 2	16253614
Determination of flavonoids from Orthosiphon stamineus in plasma using a simple HPLC method with ultraviolet detection.	2005 Feb 25	15664346
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal.	2005 Oct 4	16202168
Characterization of polymethoxylated flavones in Fructus aurantii by liquid chromatography with atmospheric pressure chemical ionization combined with tandem mass spectrometry.	2007 Apr 11	17291708
Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques.	2007 May 9	17367982
Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones.	2007 Nov	17709371
Induction of apoptosis in human cervical carcinoma HeLa cells by polymethoxylated flavone-rich Citrus grandis Osbeck (Dangyuja) leaf extract.	2010 Aug-Sep	20538032
In vitro and in vivo structure and activity relationship analysis of polymethoxylated flavonoids: identifying sinensetin as a novel antiangiogenesis agent.	2012 Jun	22707269

Patents

Sample Use Guides

In Vivo Use Guide

Sinensetin (50 mg/kg i. p.) inhibited carrageenan-induced paw inflammation in mice.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Sinensetin inhibited proliferation of MDA-MB-468 and MCF-10A cells with IC50 values of 0.2 and 65 uM respectively.

Name

Type

Language

SINENSETIN

Common Name

English

PEDALITIN PERMETHYL ETHER

Common Name

English

3',4',5,6,7-PENTAMETHOXYFLAVONE

Systematic Name

English

4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIMETHOXYPHENYL)-5,6,7-TRIMETHOXY-

Systematic Name

English

FLAVONE, 3',4',5,6,7-PENTAMETHOXY-

Systematic Name

English

5,6,7,3',4'-PENTAMETHOXYFLAVONE

Systematic Name

English

Code System Code Type Description

FDA UNII

240LNZ51AT