PENTOSALEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H14O4
Molecular Weight	270.28
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=CCOC1=C2OC(=O)C=CC2=CC3=C1OC=C3

InChI

InChIKey=OLOOJGVNMBJLLR-UHFFFAOYSA-N

InChI=1S/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C16H14O4
Molecular Weight	270.28
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/29082785
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22222157 | https://www.ncbi.nlm.nih.gov/pubmed/29332340 | https://www.ncbi.nlm.nih.gov/pubmed/28990061 | https://www.ncbi.nlm.nih.gov/pubmed/29128276

Pentosalen (Imperatorin) is a bioactive furanocoumarin and a phytochemical that has been isolated from Urena lobata L. (Malvaceae), Angelica archangelica, etc. Pentosalen has a wide range of potent pharmacological activities, including antibacterial, antitumor, anticonvulsant, acute neurotoxic effects and abirritation. Pentosalen possesses notable anti-inflammatory activity by inhibiting the production of nitric oxide (NO) and prostaglandin E2 (PGE2), and decreasing the expression of inducible nitric oxide synthase (iNOS), cyclooxygenase (COX) 2 and microsomal prostaglandin E synthase. Pentosalen selectively targets gastric cancer cells without causing much damage to normal cells. Pentosalen was identified from a Bioactive Molecules library in a high throughput screening experiment for inhibitors of the phosphodiesterase PDE4. It displays a significant preference for PDE4Bover PDE4A.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-secretase 1 21 Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22222157	Inhibitor 8297		30.5 µM [IC50]
Phosphodiesterase 4A 13 Target ID: CHEMBL254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18227226	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29332340	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Identification and determination of active components in Angelica dahurica Benth and its medicinal preparation by capillary electrophoresis.	2001 May 30	18968298
[Progress in study of chemical constituents and anti-tumor activities of Cnidium monnieri].	2005 Sep	16323535
Serotonergic activity-guided phytochemical investigation of the roots of Angelica sinensis.	2006 Apr	16643021
Remarkable substrate-specificity of CYP6AB3 in Depressaria pastinacella, a highly specialized caterpillar.	2006 Apr	16640727
[Studies on chemical constituents from roots of Peucedanum praeruptorum II].	2006 Aug	17061553
[Studies on chemical constituents in roots of Heracleum rapula].	2006 Feb	16706022
New cosmetic agents for skin whitening from Angelica dahurica.	2006 Jan-Feb	16676120
Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland.	2006 Jun	16387742
Cytochrome P450-mediated metabolism of xanthotoxin by Papilio multicaudatus.	2006 Mar	16572296
Preparative isolation of imperatorin, oxypeucedanin and isoimperatorin from traditional Chinese herb "bai zhi"Angelica dahurica (Fisch. ex Hoffm) Benth. et Hook using multidimensional high-speed counter-current chromatography.	2006 May 19	16542667
Determination of liquiritin, naringin, hesperidin, thymol, imperatorin, honokiol, isoimperatorin, and magnolol in the traditional Chinese medicinal preparation Huoxiang-zhengqi liquid using high-performance liquid chromatography.	2006 Nov	17077620
[Analysis of coumarins in Fructus Cnidii by HPLC-ESI-MS].	2006 Oct	17326403
Ethyl acetate extract from Angelica Dahuricae Radix inhibits lipopolysaccharide-induced production of nitric oxide, prostaglandin E2 and tumor necrosis factor-alphavia mitogen-activated protein kinases and nuclear factor-kappaB in macrophages.	2007 Apr	17229575
Allelic variation in the Depressaria pastinacella CYP6AB3 protein enhances metabolism of plant allelochemicals by altering a proximal surface residue and potential interactions with cytochrome P450 reductase.	2007 Apr 6	17244619
Antibacterial and anticoagulant activities of coumarins isolated from the flowers of Magydaris tomentosa.	2007 Feb	17128388
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.	2007 Feb 26	17324258
Coumarins from Cnidium monnieri and their antiosteoporotic activity.	2007 Jan	17315308
Effect of chrysin and natural coumarins on UGT1A1 and 1A6 activities in rat and human hepatocytes in primary culture.	2007 Jul	17599282
[Studies on chemical constituents in fruit of Gardenia jasminoides].	2007 Jun	17672338
Antitumor effects of Osthol from Cnidium monnieri: an in vitro and in vivo study.	2007 Mar	17154232
Antiproliferative effect of furanocoumarins from the root of Angelica dahurica on cultured human tumor cell lines.	2007 Mar	17143927
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
Imperatorin induces vasodilatation possibly via inhibiting voltage dependent calcium channel and receptor-mediated Ca2+ influx and release.	2007 Nov 14	17662269
Imperatorin enhances the protective activity of conventional antiepileptic drugs against maximal electroshock-induced seizures in mice.	2007 Nov 28	17651727
[Simultaneous determination of 5 active components in Fructus Cnidii by HPLC].	2007 Sep	18051896
Time-course and dose-response relationships of imperatorin in the mouse maximal electroshock seizure threshold model.	2007 Sep	17602770
Inhibition of acetylcholinesterase by extracts and constituents from Angelica archangelica and Geranium sylvaticum.	2007 Sep-Oct	18069242
Identification of natural coumarin compounds that rescue defective DeltaF508-CFTR chloride channel gating.	2008 Aug	18430055
Osthole and imperatorin, the active constituents of Cnidium monnieri (L.) Cusson, facilitate glutamate release from rat hippocampal nerve terminals.	2008 Dec	18951936
Enhancement of bone morphogenetic protein-2 expression and bone formation by coumarin derivatives via p38 and ERK-dependent pathway in osteoblasts.	2008 Jan 28	17980360
Micelle-mediated extraction and cloud-point preconcentration of osthole and imperatorin from Cnidium monnieri with analysis by high performance liquid chromatography.	2008 Jul 25	18579151
Influence of imperatorin on the anticonvulsant activity and acute adverse-effect profile of lamotrigine in maximal electroshock-induced seizures and chimney test in mice.	2008 Jul-Aug	18799827
Real-time fluorescence-based detection of furanocoumarin photoadducts of DNA.	2008 Jul-Aug	18401857
Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite.	2008 Jun	18510976
Simultaneous determination of 10 active components in traditional Chinese medicine "YIGONG" capsule by RP-HPLC-DAD.	2008 Jun 9	18314288
Nematicidal coumarins from Heracleum candicans Wall.	2008 May 20	18569707
Supercritical fluid extraction for identification and determination of volatile metabolites from Angelica dahurica by GC-MS.	2008 Oct	18705001
Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice.	2008 Oct 15	18692084
Lead compounds for anti-inflammatory drugs isolated from the plants of the traditional oriental medicine in Korea.	2008 Sep	18782027
Anticonvulsant and acute neurotoxic effects of imperatorin, osthole and valproate in the maximal electroshock seizure and chimney tests in mice: a comparative study.	2009 Aug	19406619
Separation and determination of coumarins in Fructus cnidii extracts by pressurized capillary electrochromatography using a packed column with a monolithic outlet frit.	2009 Dec 5	19608371
Pharmacological properties of the extract and some isolated compounds of Clausena lansium stem bark: anti-trichomonal, antidiabetic, anti-inflammatory, hepatoprotective and antioxidant effects.	2009 Feb 25	19095054
Identification and quantification of the volatile constituents in Cnidium monnieri using supercritical fluid extraction followed by GC-MS.	2009 Jan	19072900
Development and validation of a gas chromatography-mass spectrometry method for the determination of imperatorin in rat plasma and tissue: application to study its pharmacokinetics.	2009 Jul	19609025
Coumarins from Angelica lucida L.--antibacterial activities.	2009 Jul 27	19701119
Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats.	2009 Jul 29	19640308
[Effect of Chuanxiong Fangfeng Baizhi prescription on isolated rabbit basilar artery].	2009 Jun	19771875
Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice.	2009 Mar 28	19150646
Simultaneous determination of five coumarins in Angelicae dahuricae Radix by HPLC/UV and LC-ESI-MS/MS.	2009 Oct	19402180
A vascular smooth muscle/cell membrane chromatography-offline-gas chromatography/mass spectrometry method for recognition, separation and identification of active components from traditional Chinese medicines.	2009 Oct 16	19744660

Patents

Sample Use Guides

In Vivo Use Guide

330mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

The effect of imperatorin on cell viability was evaluated by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide (MTT) assay. In brief, SGC-7901 gastric cancer cells and 3T3 normal cells were seeded in a 96-well plate at a density of 2x106 cells/well. The cells were incubated for 48 hrs and then treated with various concentrations (0, 10, 50, 75, 100, 125 and 175 μM) of imperatorin and incubated for 24, 48 and 72 hrs. In the control group, the cells were treated with the solvent only (DMSO) and not the drug. Following incu¬bation, the cells were washed with PBS three times and a 200 μl solution of MTT dye was added and the whole cell sample was again incubated for 40 min. After this, the absorbance was measured at 490 nm using ELISA plate reader (ELX 800; Bio-Τek Instruments, USA).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:10:33 GMT 2023` Edited by `admin` on `Fri Dec 15 16:10:33 GMT 2023`
Record UNII	K713N25C78
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENTOSALEN

Common Name

English

Pentosalen [WHO-DD]

Common Name

English

AMMIDIN

Common Name

English

NSC-402949

Code

English

MARMELOSIN

Common Name

English

9-(3-METHYLBUT-2-ENYLOXY)FURO(3,2-G)CHROMEN-7-ONE

Systematic Name

English

8-ISOAMYLENOXYPSORALEN

Common Name

English

IMPERATORIN

Common Name

English

PENTOSALEN [HSDB]

Common Name

English

6-HYDROXY-7-(3-METHYL-2-BUTENYLOXY)-5-BENZOFURANACRYLIC ACID .GAMMA.-LACTONE

Common Name

English

IMPERATORIN [MI]

Common Name

English

9-((3-METHYL-2-BUTENYL)OXY)-7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE

Systematic Name

English

MARMELOSIN [USP-RS]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45597