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=C(CC=C(C)C)C2=C(C=CC(=O)O2)C=C1
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.
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) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release. | 2000 Mar |
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| Antiproliferative effect of isopentenylated coumarins on several cancer cell lines. | 2001 May-Jun |
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| Inhibitory effect of the plant-extract osthole on L-type calcium current in NG108-15 neuronal cells. | 2002 Jan 15 |
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| Anti-allergic effects of cnidii monnieri fructus (dried fruits of Cnidium monnieri) and its major component, osthol. | 2002 Jun |
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| [Effect of osthol on memory impairment of mice in AlCl3-induced acute senile model]. | 2002 Mar |
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| Cytotoxic activity of coumarins from the fruits of Cnidium monnieri on leukemia cell lines. | 2003 Dec |
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| [Advances in the study of chemical constituents and pharmacological actions of Cnidium monnieri (L.) Cusson]. | 2003 Feb |
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| Platelet anti-aggregatory effects of coumarins from the roots of Angelica genuflexa and A. gigas. | 2003 Sep |
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| Effect of enhancers on percutaneous absorption of osthol across the excised full thickness rat skin. | 2003 Sep |
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| Preparative isolation of osthol and xanthotoxol from Common Cnidium Fruit (Chinese traditional herb) using stepwise elution by high-speed counter-current chromatography. | 2004 Apr 16 |
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| Genetic variation in primary metabolites of Pastinaca sativa; can herbivores act as selective agents? | 2004 Oct |
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| Toxic epidermal necrolysis associated with high intake of sildenafil and its response to infliximab. | 2005 |
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| Antiproliferative effects of isopentenylated coumarins isolated from Phellolophium madagascariense Baker. | 2006 Aug |
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| Experimental study of osthole on treatment of hyperlipidemic and alcoholic fatty liver in animals. | 2006 Jul 21 |
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| Constituents, biological activities and quality control parameters of the crude extract and essential oil from Arracacia tolucensis var. multifida. | 2007 Aug 15 |
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| Antibacterial and anticoagulant activities of coumarins isolated from the flowers of Magydaris tomentosa. | 2007 Feb |
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| Coumarins from Cnidium monnieri and their antiosteoporotic activity. | 2007 Jan |
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| Effects of osthol on blood pressure and lipid metabolism in stroke-prone spontaneously hypertensive rats. | 2007 May 30 |
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| Effect of the Chinese herb extract osthol on IL-4-induced eotaxin expression in BEAS-2B cells. | 2008 Aug |
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| Identification of natural coumarin compounds that rescue defective DeltaF508-CFTR chloride channel gating. | 2008 Aug |
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| Osthole and imperatorin, the active constituents of Cnidium monnieri (L.) Cusson, facilitate glutamate release from rat hippocampal nerve terminals. | 2008 Dec |
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| Determination of osthole in rat plasma by high-performance liquid chromatograph using cloud-point extraction. | 2008 Feb 11 |
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| [Purification technology of Rhizoma et Radix Notopterygii and Radix Angelicae Pubescentis in Fufang Xuelian dropping pills by macroporous resin]. | 2008 Nov |
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| Anti-collagenase, anti-elastase and anti-oxidant activities of extracts from 21 plants. | 2009 Aug 4 |
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| 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 |
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| Osthole: a promising lead compound for drug discovery from a traditional Chinese medicine (TCM). | 2009 Feb |
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| Inhibitory effect of osthole on alcohol-induced fatty liver in mice. | 2009 Feb |
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| Identification and quantification of the volatile constituents in Cnidium monnieri using supercritical fluid extraction followed by GC-MS. | 2009 Jan |
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| 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 Jan |
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| Anti-inflammatory and antinociceptive activity of coumarins from Seseli gummiferum subsp. corymbosum (Apiaceae). | 2009 Jan-Feb |
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| Effects of osthole on apoptosis and TGF-beta1 of hypertrophic scar fibroblasts. | 2009 Jul |
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| Immunomodulatory and anti-inflammatory activity of selected osthole derivatives. | 2009 May-Jun |
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| 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 Apr |
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| Synthesis of N-hydroxycinnamides capped with a naturally occurring moiety as inhibitors of histone deacetylase. | 2010 Apr 6 |
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| Neuroprotective effect of osthole against acute ischemic stroke on middle cerebral ischemia occlusion in rats. | 2010 Dec 2 |
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| Osthole stimulates osteoblast differentiation and bone formation by activation of beta-catenin-BMP signaling. | 2010 Jun |
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| 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 Jun |
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| Osthole improves chronic cerebral hypoperfusion induced cognitive deficits and neuronal damage in hippocampus. | 2010 Jun 25 |
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| Attenuation of experimental autoimmune encephalomyelitis in C57 BL/6 mice by osthole, a natural coumarin. | 2010 Mar 10 |
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| Osthole or imperatorin-mediated facilitation of glutamate release is associated with a synaptic vesicle mobilization in rat hippocampal glutamatergic nerve endings. | 2010 May |
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| Neuroprotective effect of osthole on MPP+-induced cytotoxicity in PC12 cells via inhibition of mitochondrial dysfunction and ROS production. | 2010 Oct |
Sample Use Guides
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.
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10228
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484-12-8
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XH1TI1759C
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XH1TI1759C
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1547630
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C046627
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osthol
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31868
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DTXSID20197507
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m8263
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OSTHOL
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SUBSTANCE RECORD
