XANTHOXYLETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H14O4
Molecular Weight	258.2693
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C2C=CC(C)(C)OC2=CC3=C1C=CC(=O)O3

InChI

InChIKey=JSJIIHRNDMLJGK-UHFFFAOYSA-N

InChI=1S/C15H14O4/c1-15(2)7-6-10-12(19-15)8-11-9(14(10)17-3)4-5-13(16)18-11/h4-8H,1-3H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21875271 | https://www.ncbi.nlm.nih.gov/pubmed/20433072

Xanthoxyletin is a coumarin isolated from Erythrina variegata. It has been reported that Xanthoxyletin possesses antibacterial, fungicidal, and algicidal properties. Xanthoxyletin induces S phase arrest and apoptosis in human gastric adenocarcinoma SGC-7901 cells. Xanthoxyletin may be promising anticancer agent and has worth for further mechanistic and therapeutic studies against gastric cancer.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21875271	Activator 1447
Cyclooxygenase-2 201 Target ID: CHEMBL4321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18636311	Inhibitor 8504
thromboxane A2 signaling pathway 5 Target ID: GO:0038193 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1523611	Inhibitor 8504
Carbonic anhydrase IX 36 Target ID: CHEMBL3594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22892213	Inhibitor 8504	0.74 µM [Ki]
Carbonic anhydrase XII 30 Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22892213	Inhibitor 8504	0.96 µM [Ki]
Carbonic anhydrase XIII 10 Target ID: CHEMBL3912 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22892213	Inhibitor 8504	3.15 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gastric cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21875271	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antimicrobial coumarins from the stem bark of Afraegle paniculata.	2010-04	20433072
Anti-HBV and cytotoxic activities of pyranocoumarin derivatives.	2009-08-15	19635670
Isolation of xanthyletin, an inhibitor of ants' symbiotic fungus, by high-speed counter-current chromatography.	2009-05-08	19296958
Inhibitory effect of oxycoumarins isolated from the Thai medicinal plant Clausena guillauminii on the inflammation mediators, iNOS, TNF-alpha, and COX-2 expression in mouse macrophage RAW 264.7.	2009-01	18636311
Chemical characterization of Citrus sinensis grafted on C. limonia and the effect of some isolated compounds on the growth of Xylella fastidiosa.	2008-09-10	18683948
Separation and determination of coumarins in the root bark of three citrus plants by micellar electrokinetic capillary chromatography.	2003-05	12802740
Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a net C-H insertion.	2003-04-16	12683822
[Studies on the coumarins in the root of Zanthoxylum dimorphophyllum].	2003-04	15139146
Coumarins and carbazoles from Clausena excavata exhibited antimycobacterial and antifungal activities.	2003-02	12624822
Cytotoxic naphthoquinones and plumbagic acid glucosides from Plumbago zeylanica.	2003-02	12560036
Cytotoxic coumarins and lignans from extracts of the northern prickly ash (Zanthoxylum americanum).	2001-08	11507740

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

After treating the SGC-7901 cells with 200 and 400 uM of Xanthoxyletin for 48 h, ROS production was detected and the ratios of DCF-positive cells were 18.66% and 32.86% respectively as compared to 8.27% in the control group. Xanthoxyletin induced apoptosis in SGC-7901 cells and percentage of apoptotic cells was 41.47% after the exposure of 400 uM of Xanthoxyletin for 48 h as compared to 2.6% in the control group.

Name

Type

Language

NSC-35542

Preferred Name

English

XANTHOXYLETIN

Common Name

English

7-HYDROXY-5-METHOXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-ACRYLIC ACID .DELTA.-LACTONE

Common Name

English

XANTHOXYLIN N

Common Name

English

XANTHOXYLETIN [MI]

Common Name

English

XANTHOXYLOIN

Common Name

English

Code System Code Type Description

CAS

84-99-1