ANGELICIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H6O3
Molecular Weight	186.1635
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1OC2=C(C=CC3=C2C=CO3)C=C1

InChI

InChIKey=XDROKJSWHURZGO-UHFFFAOYSA-N

InChI=1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3473010 | https://www.ncbi.nlm.nih.gov/pubmed/561302 | https://www.ncbi.nlm.nih.gov/pubmed/19684342 | https://www.ncbi.nlm.nih.gov/pubmed/27748898 | https://www.ncbi.nlm.nih.gov/pubmed/25352883 | https://www.ncbi.nlm.nih.gov/pubmed/24803987 | https://www.ncbi.nlm.nih.gov/pubmed/11169165

Angelicin (isopsoralen), is a furocoumarin, occuring in a number of plants belonging to the Umbelliferae family. It acts as a photosensitizer by forming DNA monoadducts. Angelicin is able to inhibit monoamine oxidase (MAO) activities in rat brain mitochondria. Angelicin exerts antineoplastic and antidiabetic properties in animal models.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/399905 \| https://www.ncbi.nlm.nih.gov/pubmed/6445206 \| https://www.ncbi.nlm.nih.gov/pubmed/561302 \| https://www.ncbi.nlm.nih.gov/pubmed/19684342	Binding Agent 1064
Monoamine oxidase A 49 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11169165	Inhibitor 8297	9.0 µM [IC50]
Monoamine oxidase B 72 Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11169165	Inhibitor 8297	12.8 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27748898 https://www.ncbi.nlm.nih.gov/pubmed/25352883	Primary	Preclinical	Unknown Approved Use Unknown
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27581277	Primary	Preclinical	Unknown Approved Use Unknown
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24803987	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Reversed-phase high-performance liquid chromatography (RP-HPLC) determination of lipophilicity of furocoumarins: relationship with DNA interaction.	2001 Jun	11357176
In silico rationalization of the structural and physicochemical requirements for photobiological activity in angelicine derivatives and their heteroanalogues.	2003 Jan	12926855
Assignment of absolute configuration of a chiral phenyl-substituted dihydrofuroangelicin.	2003 Jan 7	12929409
1-Thioangelicin: crystal structure, computer-aided studies and photobiological activity.	2004 Feb	14871504
An efficient new method for extraction, separation and purification of psoralen and isopsoralen from Fructus Psoraleae by supercritical fluid extraction and high-speed counter-current chromatography.	2004 Nov 5	15560489
Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes.	2005 Feb 15	15670584
Protective effect of furocoumarins against 254-nm ultraviolet in Staphylococcus aureus.	2006 Jan	16320118
gamma-H2AX formation in response to interstrand crosslinks requires XPF in human cells.	2006 Jun 10	16678501
Helicoverpa zea CYP6B8 and CYP321A1: different molecular solutions to the problem of metabolizing plant toxins and insecticides.	2007 Dec	18065401
Psoralen and isopsoralen, two coumarins of Psoraleae Fructus, can alleviate scopolamine-induced amnesia in rats.	2007 Mar	17318785
Central role of mitochondria and p53 in PUVA-induced apoptosis in human keratinocytes cell line NCTC-2544.	2008 Feb 15	18048073
Pharmacological targeting of NF-kappaB potentiates the effect of the topoisomerase inhibitor CPT-11 on colon cancer cells.	2008 Jan 29	18182997
Real-time fluorescence-based detection of furanocoumarin photoadducts of DNA.	2008 Jul-Aug	18401857
Montelukast inhibits tumour necrosis factor-alpha-mediated interleukin-8 expression through inhibition of nuclear factor-kappaB p65-associated histone acetyltransferase activity.	2008 May	18325031
Phytophotodermatitis in Rijeka region, Croatia.	2008 Oct	19138025
Fetal globin induction in beta-thalassemia.	2009	20001626
Differentiation and apoptosis in UVA-irradiated cells treated with furocoumarin derivatives.	2009 Aug	19723073
Anti-collagenase, anti-elastase and anti-oxidant activities of extracts from 21 plants.	2009 Aug 4	19653897
Isolation and functional characterization of CYP71AJ4 encoding for the first P450 monooxygenase of angular furanocoumarin biosynthesis.	2009 Feb 20	19098286
Fetal Hemoglobin Inducers from the Natural World: A Novel Approach for Identification of Drugs for the Treatment of {beta}-Thalassemia and Sickle-Cell Anemia.	2009 Jun	18955291
Repair of laser-localized DNA interstrand cross-links in G1 phase mammalian cells.	2009 Oct 9	19684342
Simultaneous determination of psoralen and isopsoralen in plasma and Chinese medicine Xian Ling Gu Bao capsule by using HPLC-DAD coupled with alternating trilinear decomposition algorithm.	2009 Sep 21	19720187
Differentiation of four pairs of furocoumarin isomers by electrospray ionization tandem mass spectrometry.	2010	20212330
Naturally occurring food toxins.	2010 Sep	22069686

Patents

Sample Use Guides

In Vivo Use Guide

The purpose of this study was to determine the protective effects of angelicin on allergic asthma induced by ovalbumin (OVA) in mice. Mice were sensitized to OVA (on days 0 and 14) and challenged with OVA three times (on days 21 to 23). Angelicin (2.5, 5, 10 mg/kg) was given intraperitoneally 1 h before OVA treatment after the initial OVA sensitization.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Angelicin increased cellular cytotoxicity against human SH-SY5Y neuroblastoma cells in a dose- and time-dependent manner with IC(50) of 49.56 μM at 48 h of incubation.

Name

Type

Language

ANGELICIN

Common Name

English

2H-FURO(2,3-H)-1-BENZOPYRAN-2-ONE

Systematic Name

English

ISOPSORALEN

Common Name

English

ISOPSORALEN [HSDB]

Common Name

English

NSC-404563

Code

English

Code System Code Type Description

PUBCHEM

10658