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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26337552
Curator's Comment: referenced study was conducted in mice
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25013761 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17154232
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17154232
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.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 |
SUBSTANCE RECORD