ESCULETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H6O4
Molecular Weight	178.1415
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=C(C=CC(=O)O2)C=C1O

InChI

InChIKey=ILEDWLMCKZNDJK-UHFFFAOYSA-N

InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3780217 | https://www.ncbi.nlm.nih.gov/pubmed/25517918 | https://www.ncbi.nlm.nih.gov/pubmed/26388407 | https://www.ncbi.nlm.nih.gov/pubmed/28643798

Esculetin (aka Aesculetin) is a derivative of coumarin. It is a naturally occurring lactone which is present in chicory and in many toxic medicinal plants; often found in a glycosidic form or conjugated to caffeic acids. It is used as an ingredient in some sunscreens, but there is evidence that it acts as a photosensitizer for DNA damage. Esculetin has been investigated in a number of cellular and animal cancer models, and for other conditions such as dry eyes.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Caspase-3 21 Target ID: P42574 Gene ID: 836.0 Gene Symbol: CASP3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25517918	Activator 1430
Caspase-9 5 Target ID: P55211\|\|\|Q9UEQ3 Gene ID: 842.0 Gene Symbol: CASP9 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25517918	Activator 1430
Arachidonate 5-lipoxygenase 49 Target ID: P12527 Gene ID: 25290.0 Gene Symbol: Alox5 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25425056	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25517918 https://www.ncbi.nlm.nih.gov/pubmed/26388407	Primary	Basic research	Unknown Approved Use Unknown
Dry eye syndrome 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28643798	Primary	Basic research	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25425056	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Dietary polyunsaturated fatty acid and antioxidant modulation of vascular dysfunction in the spontaneously hypertensive rat.	2001 Aug	11545625
Studies on the hepatocyte protective activity and the structure-activity relationships of quinic acid and caffeic acid derivatives from the flower buds of Lonicera bournei.	2001 Jun	11458447
Eicosanoids participate in the regulation of cardiac glucose transport by contribution to a rearrangement of actin cytoskeletal elements.	2001 Oct 1	11563968
Role of mitochondrial complexes I and II, reactive oxygen species and arachidonic acid metabolism in deoxycholate-induced apoptosis.	2002 Mar 28	11825660
New coumarins from Cedrelopsis grevei.	2003 Dec	14630167
P53 hot-spot mutants are resistant to ubiquitin-independent degradation by increased binding to NAD(P)H:quinone oxidoreductase 1.	2003 Dec 9	14634213
Protection of coumarins against linoleic acid hydroperoxide-induced cytotoxicity.	2003 Jan 6	12453663
Prostaglandins, not lipoxygenase products, mediate insect microaggregation reactions to bacterial challenge in isolated hemocyte preparations.	2003 Oct	14511759
Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities.	2004	15579073
[Lipoxygenase inhibition and protection of cardiovascular system].	2004 Jan	14737852
Evidence for colorectal cancer cell specificity of aspirin effects on NF kappa B signalling and apoptosis.	2004 Jul 19	15188000
Analysis of ADAMTS4 and MT4-MMP indicates that both are involved in aggrecanolysis in interleukin-1-treated bovine cartilage.	2005 Apr	15780640
Isolation and purification of coumarin compounds from Cortex fraxinus by high-speed counter-current chromatography.	2005 Apr 29	15887488
Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin.	2005 Aug	15824923
Protective effect of epigallocatechin gallate and esculetin on oxidative DNA damage induced by psoralen plus ultraviolet-A therapy.	2005 Mar	15784992
Eicosanoids mediate the laminarin-induced nodulation response in larvae of the flesh fly, Neobellieria bullata.	2005 May	15822095
Non-aqueous capillary electrophoresis for separation and simultaneous determination of fraxin, esculin and esculetin in Cortex fraxini and its medicinal preparations.	2005 Nov	15828063
Characterization of an O-methyltransferase from soybean.	2006 Apr	16777424
Biosynthesis and functions of eicosanoids generated by the coelomocytes of the starfish, Asterias rubens.	2007 Aug	17499535
A rapid TLC autographic method for the detection of glucosidase inhibitors.	2007 May-Jun	17500363

Patents

Sample Use Guides

In Vivo Use Guide

In a study of acute non-inflammatory pain and acute inflammatory pain. Rats were given 1.25 - 20 mg/kg esculetin by intraperitoneal injection. Esculetin was found to dose-dependently alleviate hyperalgesia and exhibit antinociceptive effects in both experimental models.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Human hepatocellular carcinoma cells SMMC-7721 were maintained in DMEM supplemented with 10% heat-inactivated fetal bovine serum at 37 deg-C in a 5% CO2 atmosphere. Cells were seeded onto 96 well plates ata density of 1x10^4 cells/mL in 0.1 mL medium an cultured for 24 hours. Cells were treated with various concentrations of esculetin (0 - 5 mM) for 24, 48 and 72 hours. Cell proliferation was assessed using the MTT assay method. Esculetin significantly inhibited the viability of hepatocellular carcinoma cells in a dose- and time-dependent manner. The IC50 values of esculetin against SMMC-7721 cells at 72 h was 2.24 mM.

Name

Type

Language

ESCULETIN

Official Name

English

ESCULETIN [MI]

Common Name

English

6,7-DIHYDROXYCOUMARIN

Systematic Name

English

CICHORIGENIN

Common Name

English

ESCULETIN [INCI]

Common Name

English

6,7-DIHYDROXY-2H-1-BENZOPYRAN-2-ONE

Systematic Name

English

NSC-26428

Code

English

Code System Code Type Description

ECHA (EC/EINECS)

206-161-5