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 73 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25442272	Inhibitor 8504	40.2 µM [IC50]
alpha-glucosidase activity 3 Target ID: GO:0090599 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23039079	Inhibitor 8504
alpha-amylase activity 1 Target ID: GO:0004556 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23039079	Inhibitor 8504
Arachidonate 15-lipoxygenase 6 Target ID: CHEMBL2903 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11087521	Inhibitor 8504	74.0 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL4321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22516932	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23039079	Primary		Basic research	Unknown Approved Use Unknown
Inflammation 105 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22516932	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro and in vivo structure and activity relationship analysis of polymethoxylated flavonoids: identifying sinensetin as a novel antiangiogenesis agent.	2012-06	22707269
Isolation and identification of polymethoxyflavones from the hybrid Citrus, hallabong.	2010-09-08	20698540
Suppression of bacterial cell-cell signalling, biofilm formation and type III secretion system by citrus flavonoids.	2010-08	20163489
HPLC and anti-inflammatory studies of the flavonoid rich chloroform extract fraction of Orthosiphon stamineus leaves.	2010-06-21	20657453
Polymethoxylated flavones, flavanone glycosides, carotenoids, and antioxidants in different cultivation types of tangerines ( Citrus reticulata Blanco cv. Sainampueng) from Northern Thailand.	2010-05-26	20420369
Induction of apoptosis in human cervical carcinoma HeLa cells by polymethoxylated flavone-rich Citrus grandis Osbeck (Dangyuja) leaf extract.	2010-03-20	20538032
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.	2010-03-02	20479987
Flavonoids from the stems of Croton caudatus Geisel. var. tomentosus Hook.	2010-02-26	20335965
Methylation of dietary flavones increases their metabolic stability and chemopreventive effects.	2009-11-18	20087474
CYP1-mediated antiproliferative activity of dietary flavonoids in MDA-MB-468 breast cancer cells.	2009-10-29	19666078
UPLC/Q-TOFMS/MS as a powerful technique for rapid identification of polymethoxylated flavones in Fructus aurantii.	2009-08-15	19428213
Evaluation of the anti-pyretic potential of Orthosiphon stamineus Benth standardized extract.	2009-02	19127348
Epigenetic mechanisms involved in differential MDR1 mRNA expression between gastric and colon cancer cell lines and rationales for clinical chemotherapy.	2008-08-01	18673531
Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts.	2008-01	18095294
Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones.	2007-11	17709371
Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques.	2007-05-09	17367982
Characterization of polymethoxylated flavones in Fructus aurantii by liquid chromatography with atmospheric pressure chemical ionization combined with tandem mass spectrometry.	2007-04-11	17291708
Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on P-glycoprotein-mediated transport of talinolol in Caco-2 cells.	2007-04-04	17348674
Determination of polymethoxylated flavones in peels of selected Jamaican and Mexican citrus (Citrus spp.) cultivars by high-performance liquid chromatography.	2007-01	17080505
Polymethoxylated flavones induce Ca(2+)-mediated apoptosis in breast cancer cells.	2006-12-23	17046027
Citrus flavonoids in fruit and traditional Chinese medicinal food ingredients in China.	2006-06	16816988
Liquid chromatography/mass spectrometry and liquid chromatography/nuclear magnetic resonance as complementary analytical techniques for unambiguous identification of polymethoxylated flavones in residues from molecular distillation of orange peel oils (Citrus sinensis).	2006-01-25	16417279
Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities.	2005-12-02	16253614
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal.	2005-10-04	16202168
Determination of flavonoids from Orthosiphon stamineus in plasma using a simple HPLC method with ultraviolet detection.	2005-02-25	15664346
Changes in the levels of polymethoxyflavones and flavanones as part of the defense mechanism of Citrus sinensis (cv. Valencia Late) fruits against Phytophthora citrophthora.	2004-04-07	15053528
Effect of extraction method on the concentrations of selected bioactive compounds in mandarin juice.	2003-12-03	14640582
Reversal of P-glycoprotein-mediated multidrug resistance by 5,6,7,3',4'-pentamethoxyflavone (Sinensetin).	2002-07-26	12127970
Increasing resistance against Phytophthora citrophthora in tangelo Nova fruits by modulating polymethoxyflavones levels.	2002-05-08	11982408
Genetic toxicity of a standardized mixture of citrus polymethoxylated flavones.	2002-05	11955667
Immunotoxicity of a standardized citrus polymethoxylated flavone extract.	2001-11	11527568

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 `Mon Mar 31 19:56:10 GMT 2025` Edited by `admin` on `Mon Mar 31 19:56:10 GMT 2025`
Record UNII	240LNZ51AT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PEDALITIN PERMETHYL ETHER

Preferred Name

English

SINENSETIN

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