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Details

Stereochemistry ACHIRAL
Molecular Formula C15H16O3
Molecular Weight 244.2857
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OSTHOL

SMILES

COC1=CC=C2C=CC(=O)OC2=C1CC=C(C)C

InChI

InChIKey=MBRLOUHOWLUMFF-UHFFFAOYSA-N
InChI=1S/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C15H16O3
Molecular Weight 244.2857
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Osthol is an O-methylated coumarin found in plants such as Cnidium monnieri, Angelica archangelica and Angelica pubescens which are often used in traditional eastern medicine. It is known to be a calcium channel blocker and is reported to have neuroprotective, osteogenic, immunomodulatory, anticancer, hepatoprotective, cardiovascular protective, and antimicrobial activities.

CNS Activity

Curator's Comment: referenced study was conducted in mice

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P0A0J7
Gene ID: NA
Gene Symbol: norA
Target Organism: Staphylococcus aureus
34.0 µM [IC50]
Target ID: P04637|||Q16810|||Q3LRW5|||Q9NZD0
Gene ID: 7157.0
Gene Symbol: TP53
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Neuroprotective effect of osthole against acute ischemic stroke on middle cerebral ischemia occlusion in rats.
2010-12-02
Osthole regulates inflammatory mediator expression through modulating NF-κB, mitogen-activated protein kinases, protein kinase C, and reactive oxygen species.
2010-10-13
Neuroprotective effect of osthole on MPP+-induced cytotoxicity in PC12 cells via inhibition of mitochondrial dysfunction and ROS production.
2010-10
In vivo imaging of zebrafish retinal cells using fluorescent coumarin derivatives.
2010-09-15
Antifungal activity of the osthol derivative JS-B against Phytophthora capsici.
2010-08
Osthol regulates hepatic PPAR alpha-mediated lipogenic gene expression in alcoholic fatty liver murine.
2010-07
Osthole improves chronic cerebral hypoperfusion induced cognitive deficits and neuronal damage in hippocampus.
2010-06-25
Prenylcoumarin with Rev-export inhibitory activity from Cnidii Monnieris Fructus.
2010-06-15
Osthole stimulates osteoblast differentiation and bone formation by activation of beta-catenin-BMP signaling.
2010-06
On-line concentration by field-enhanced sample injection with reverse migrating micelles in micellar electrokinetic capillary chromatography for the analysis of coumarins from traditional Chinese medicine and human serum.
2010-06
[Optimization of extraction process for compund kaliziran gel with orthogonal design].
2010-05
Osthole or imperatorin-mediated facilitation of glutamate release is associated with a synaptic vesicle mobilization in rat hippocampal glutamatergic nerve endings.
2010-05
Osthole suppresses fatty acid synthase expression in HER2-overexpressing breast cancer cells through modulating Akt/mTOR pathway.
2010-04-28
Synthesis of N-hydroxycinnamides capped with a naturally occurring moiety as inhibitors of histone deacetylase.
2010-04-06
Fast separation and determination of coumarins in Fructus cnidii extracts by CEC using poly(butyl methacrylate-co-ethylene dimethacrylate-co-[2-(methacryloyloxy)ethyl] trimethylammonium chloride) monolithic columns.
2010-04
Attenuation of experimental autoimmune encephalomyelitis in C57 BL/6 mice by osthole, a natural coumarin.
2010-03-10
The effect of the major components of Fructus Cnidii on osteoblasts in vitro.
2010-03
Osthol is a use-dependent blocker of voltage-gated Na+ channels in mouse neuroblastoma N2A cells.
2010-01
Effects of osthole on migration and invasion in breast cancer cells.
2010
Separation and determination of coumarins in Fructus cnidii extracts by pressurized capillary electrochromatography using a packed column with a monolithic outlet frit.
2009-12-05
Osthole, a potential antidiabetic agent, alleviates hyperglycemia in db/db mice.
2009-10-30
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.
2009-10-16
[Metabolism of osthol in isolated hepatocytes of rat].
2009-10
Efficacy of osthol, a potent coumarin compound, in controlling powdery mildew caused by Sphaerotheca fuliginea.
2009-09
Immunomodulatory and anti-inflammatory activity of selected osthole derivatives.
2009-08-15
Anti-collagenase, anti-elastase and anti-oxidant activities of extracts from 21 plants.
2009-08-04
Anticonvulsant and acute neurotoxic effects of imperatorin, osthole and valproate in the maximal electroshock seizure and chimney tests in mice: a comparative study.
2009-08
Determination of osthol and its metabolites in a phase I reaction system and the Caco-2 cell model by HPLC-UV and LC-MS/MS.
2009-07-12
Effects of osthole on apoptosis and TGF-beta1 of hypertrophic scar fibroblasts.
2009-07
Osthole suppresses seizures in the mouse maximal electroshock seizure model.
2009-04-01
Anti-inflammatory and antinociceptive activity of coumarins from Seseli gummiferum subsp. corymbosum (Apiaceae).
2009-03-28
Osthole: a promising lead compound for drug discovery from a traditional Chinese medicine (TCM).
2009-02
Inhibitory effect of osthole on alcohol-induced fatty liver in mice.
2009-02
Identification and quantification of the volatile constituents in Cnidium monnieri using supercritical fluid extraction followed by GC-MS.
2009-01
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
Osthole and imperatorin, the active constituents of Cnidium monnieri (L.) Cusson, facilitate glutamate release from rat hippocampal nerve terminals.
2008-12
Osthol and isopimpinellin from Fructus cnidii for the control of Dactylogyrus intermedius in Carassius auratus.
2008-11-25
[Purification technology of Rhizoma et Radix Notopterygii and Radix Angelicae Pubescentis in Fufang Xuelian dropping pills by macroporous resin].
2008-11
Osthole regulates enzyme protein expression of CYP7A1 and DGAT2 via activation of PPARalpha/gamma in fat milk-induced fatty liver rats.
2008-08-13
Effect of the Chinese herb extract osthol on IL-4-induced eotaxin expression in BEAS-2B cells.
2008-08
Attempts to bridge the gap between scientific mechanism-based medicine and Chinese herbal extract treatment for asthma.
2008-08
Identification of natural coumarin compounds that rescue defective DeltaF508-CFTR chloride channel gating.
2008-08
Micelle-mediated extraction and cloud-point preconcentration of osthole and imperatorin from Cnidium monnieri with analysis by high performance liquid chromatography.
2008-07-25
Isolation and identification of insecticidal components from Citrus aurantium fruit peel extract.
2008-07-23
Petroleum ether extract of Cnidium monnieri ameliorated scopolamine-induced amnesia through adrenal gland-mediated mechanism in male rats.
2008-05-22
[Absorption and transport of 6 coumarins isolated from the roots of Angelica pubescens f. biserrata in human Caco-2 cell monolayer model].
2008-04
Determination and pharmacokinetic study of indirubin in rat plasma by high-performance liquid chromatography.
2008-04
Fusarium graminearum growth inhibition due to glucose starvation caused by osthol.
2008-03
Chemical and antibacterial constituents of Skimmia anquetelia.
2008-02
[In situ rats single pass perfusion intestinal absorption of the effectivein components in Radix Angelicae Pubescentis].
2008-01
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: the referenced study was conducted on mice
The antitumor effects of osthol were evaluated using the murine P-388 D1 leukemia in vivo model. P-388 D1 cells were transplanted intraperitoneally into 5-week-old CDF1 female mice on day zero. Osthol was dissolved in 10% soybean oil and administered orally once per day on days 0 - 8 at a dose of 30 mg/kg. The life-span of tumor-bearing mice receiving osthol was increased by more than 37.5% compared to solvent control mice.
Route of Administration: Oral
Human cervical carcinoma (HeLa) were maintained in DMEM supplemented with 10% FBS, 100 mg/L streptomycin, and 100 IU/mL penicillin and incubated at 37 deg-C in a 5% CO2 atmosphere. Cell cultures were prepared in a 96 well plate and incubated for 24 and 48 hours with a range of Osthol concentrations. The surviving cells were counted using the tetrazolium assay. Osthol inhibited the growth of HeLa cells in a time and concentration-dependent manner, with IC50 values of 77.96 and 64.94 microM for 24 and 48 hours respectively.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:01:02 GMT 2025
Edited
by admin
on Mon Mar 31 19:01:02 GMT 2025
Record UNII
XH1TI1759C
Record Status Validated (UNII)
Record Version
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Name Type Language
OSTHOL
Common Name English
OSTHOLE
INCI   MI  
INCI  
Preferred Name English
OSTHOLE [MI]
Common Name English
7-METHOXY-8-(3-METHYLBUT-2-EN-1-YL)-2H-CHROMEN-2-ONE
Systematic Name English
NSC-31868
Code English
7-METHOXY-8-(3-METHYL-2-BUTENYL)-2H-1-BENZOPYRAN-2-ONE
Systematic Name English
7-METHOXY-8-(3-METHYLBUT-2-ENYL)-2-CHROMENONE
Systematic Name English
Code System Code Type Description
PUBCHEM
10228
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY
CAS
484-12-8
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY
FDA UNII
XH1TI1759C
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY
DAILYMED
XH1TI1759C
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY
RXCUI
1547630
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY RxNorm
MESH
C046627
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY
ALANWOOD
osthol
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY
NSC
31868
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID20197507
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY
MERCK INDEX
m8263
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
OSTHOL
Created by admin on Mon Mar 31 19:01:02 GMT 2025 , Edited by admin on Mon Mar 31 19:01:02 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT