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

Molecular Formula	C11H6O3
Molecular Weight	186.1635
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/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
Comparison of the global genomic and transcription-coupled repair rates of different lesions in human cells.	2004 May-Jun	18998417
Genome-wide requirements for resistance to functionally distinct DNA-damaging agents.	2005 Aug	16121259
[Studies on chemical constituents in rhizome of Elaeagnus bockii I].	2006 Jun	17048645
gamma-H2AX formation in response to interstrand crosslinks requires XPF in human cells.	2006 Jun 10	16678501
A deficit of detoxification enzymes: pesticide sensitivity and environmental response in the honeybee.	2006 Oct	17069637
Chemical fingerprint and quantitative analysis of fructus psoraleae by high-performance liquid chromatography.	2007 Apr	17536725
Fluorescent DNA probes: study of mechanisms of changes in spectral properties and features of practical application.	2007 Aug	17922647
Helicoverpa zea CYP6B8 and CYP321A1: different molecular solutions to the problem of metabolizing plant toxins and insecticides.	2007 Dec	18065401
Molecular cloning and functional characterization of psoralen synthase, the first committed monooxygenase of furanocoumarin biosynthesis.	2007 Jan 5	17068340
[Study on micro-wave processed of Psoralea corylifolia with uniform and regression analysis].	2007 Jun	17802878
Psoralen and isopsoralen, two coumarins of Psoraleae Fructus, can alleviate scopolamine-induced amnesia in rats.	2007 Mar	17318785
Induction of apoptosis in Jurkat cells by photoexcited psoralen derivatives: Implication of mitochondrial dysfunctions and caspases activation.	2007 Mar	17084583
High-performance liquid chromatographic method for the determination and pharmacokinetic study of oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma.	2007 May 9	17344014
Separation and determination of psoralen and isopsoralen by microemulsion electrokinetic chromatography.	2007 Oct	17582232
3-Methyladenine DNA glycosylase is important for cellular resistance to psoralen interstrand cross-links.	2008 Aug 2	18571479
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
Furocoumarins photolysis products induce differentiation of human erythroid cells.	2008 Jul 24	18485726
Real-time fluorescence-based detection of furanocoumarin photoadducts of DNA.	2008 Jul-Aug	18401857
An HPLC method for determination of oridonin in rabbits using isopsoralen as an internal standard and its application to pharmacokinetic studies for oridonin-loaded nanoparticles.	2008 Jun 15	18514594
Montelukast inhibits tumour necrosis factor-alpha-mediated interleukin-8 expression through inhibition of nuclear factor-kappaB p65-associated histone acetyltransferase activity.	2008 May	18325031
Thiopyrano[2,3-e]indol-2-ones: angelicin heteroanalogues with potent photoantiproliferative activity.	2008 Nov 15	18951030
Phytophotodermatitis in Rijeka region, Croatia.	2008 Oct	19138025
Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice.	2008 Oct 15	18692084
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
[Studies on chemical constituents from roots of Polygonum amplexicaule].	2009 Jan	19385182
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
Pyrano[2,3-e]isoindol-2-ones, new angelicin heteroanalogues.	2009 Mar 15	19230658
The human oxidative DNA glycosylase NEIL1 excises psoralen-induced interstrand DNA cross-links in a three-stranded DNA structure.	2009 May 1	19258314
Increase in gamma-globin mRNA content in human erythroid cells treated with angelicin analogs.	2009 Oct	19777196
Simultaneous quantification of psoralen and isopsoralen in rat plasma by ultra-performance liquid chromatography/tandem mass spectrometry and its application to a pharmacokinetic study after oral administration of Haigou Pill.	2009 Oct 1	19671498
Repair of laser-localized DNA interstrand cross-links in G1 phase mammalian cells.	2009 Oct 9	19684342
Simultaneous determination of seven components in Qibaomeiran pill by HPLC-DAD.	2009 Sep	19772753
Relative photomutagenicity of furocoumarins and limettin in the hypoxanthine phosphoribosyl transferase assay in V79 cells.	2009 Sep	19725558
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
Two new coumarins from the chloroform extract of Angelica urumiensis from Iran.	2010 Apr	20410639
Pharmacokinetics, tissue distribution and excretion of coumarin components from Psoralea corylifolia L. in rats.	2010 Feb	20195822
Phytoestrogens from Psoralea corylifolia reveal estrogen receptor-subtype selectivity.	2010 Feb	19577453
Anti-influenza drug discovery: structure-activity relationship and mechanistic insight into novel angelicin derivatives.	2010 Feb 25	20092255
Psoralea corylifolia Linn.-"Kushtanashini".	2010 Jan	22228944
A pterocarpan from the seeds of Bituminaria morisiana.	2010 Jul	20238177
Synthesis of pyrrolo[3,2-h]quinolinones with good photochemotherapeutic activity and no DNA damage.	2010 Jul 1	20627596
Naturally occurring food toxins.	2010 Sep	22069686
Furocoumarins affect hepatic cytochrome P450 and renal organic ion transporters in mice.	2012 Feb 25	22173200
The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins.	2013 May 2	23501157
Brd4 is essential for IL-1β-induced inflammation in human airway epithelial cells.	2014	24759736

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:19:43 GMT 2023` Edited by `admin` on `Fri Dec 15 17:19:43 GMT 2023`
Record UNII	CZZ080D7BD
Record Status	`Validated (UNII)`
Record Version

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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