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

Molecular Formula	C20H20O7
Molecular Weight	372.3686
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Determination of flavonoids from Orthosiphon stamineus in plasma using a simple HPLC method with ultraviolet detection.	2005 Feb 25	15664346
Determination of polymethoxylated flavones in peels of selected Jamaican and Mexican citrus (Citrus spp.) cultivars by high-performance liquid chromatography.	2007 Jan	17080505
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
HPLC and anti-inflammatory studies of the flavonoid rich chloroform extract fraction of Orthosiphon stamineus leaves.	2010 Jun 21	20657453
Isolation and identification of polymethoxyflavones from the hybrid Citrus, hallabong.	2010 Sep 8	20698540
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:45:43 GMT 2023` Edited by `admin` on `Fri Dec 15 19:45:43 GMT 2023`
Record UNII	240LNZ51AT
Record Status	`Validated (UNII)`
Record Version

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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