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1-O-Acetyl britannilactone

CAS# 681457-46-5

1-O-Acetyl britannilactone

Catalog No. BCN2365----Order now to get a substantial discount!

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Quality Control of 1-O-Acetyl britannilactone

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Chemical structure

1-O-Acetyl britannilactone

3D structure

Chemical Properties of 1-O-Acetyl britannilactone

Cas No. 681457-46-5 SDF Download SDF
PubChem ID 102004923 Appearance Cryst.
Formula C17H24O5 M.Wt 308.4
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 4-[(3aS,4R,7aR)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,7,7a-tetrahydro-1-benzofuran-5-yl]pentyl acetate
SMILES CC1=C(C(C2C(C1)OC(=O)C2=C)O)C(C)CCCOC(=O)C
Standard InChIKey QKUFZFLZBUSEHN-MCJOIMHTSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 1-O-Acetyl britannilactone

The herbs of Inula japonica Thunb.

Biological Activity of 1-O-Acetyl britannilactone

Description1-O-Acetyl britannilactone shows antifungal, and anti-cancer activities, it suppresses angiogenesis and lung cancer cell growth possibly via regulating the VEGFR-Src-FAK signaling. 1-O-Acetyl britannilactone may be one anti-inflammatory drug which inhibits the expression of COX-2 gene by blocking NF-κB activation and thus suppresses the inflammatory response to LPS in vascular smooth muscle cells.
Targetsp65 | NF-kB | COX | IkB | VEGFR | Src | FAK | IKK
In vitro

Separation and analysis of 1-O-acetylbritannilactone from Inula japonica and determination of antifungal activity[Reference: WebLink]

Acta Phytophylacica Sinica, 2008 , 35 (6) :551-6.

In order to clarify the main antifungal compound of Inula japonica,the chloroform extraction of crude extract from I.japonica flowers was separated and compound 1-O-Acetyl britannilactone (ABL) was obtained.
METHODS AND RESULTS:
The content of the compound ABL in flowers crude extract was tested with high performance liquid chromatography.The inhibitory effects of compound ABL against Sphaerotheca fuliginea,Pseudoperonospora cubensis,Botrytis cinerea,Alternaria solani and Phytophthora infestans were tested.The chemical structure of ABL reference substance was elucidated by using ultraviolet spectrometry(UV),infrared spectroscopy(IR),nuclear magnetic resonance(NMR).The purity of ABL reference substance was 99.5%,which satisfies the need of reference substances of traditional Chinese medicines.A method of high performance liquid chromatography was used for the determination of the content of ABL in crude extract from I.japonica flowers(it's 2.45%),then the content of ABL in I.japonica was calculated(it's about 0.25%).
CONCLUSIONS:
Inhibitory activities of compound ABL against the five phytopathogenic fungi were different,which against the cystospore germination of P.infestans was significant,the inhibition rate was 100% at the concentration 0.1 mg/mL.

1-o-acetylbritannilactone Inhibits Inflammatory Response by Suppressing NF-κB Activation[Reference: WebLink]

Chinese Journal of Cell Biology, 2007 , 29 (2) :267-71.

Immunocytochemistry and Western blot analysis were adopted to measure the nuclear translo-cation of NF-κB p65 and the expression of IκB-α, cyclo-oxygenase-2 (COX-2).
METHODS AND RESULTS:
Electrophoretic mobility shift assay (EMSA) was performed to detect DNA-binding activity of NF-κB in vascular smooth muscle cells (VSMC) pre-treated with ABL. Western blot and immunocytochemistry analysis showed that lipopolysaccharide (LPS) treatment resulted in increasing nuclear translocation of NF-κB p65, and declining levels of IκB-α in VSMC. However, 1-O-Acetyl britannilactone (ABL) pretreatment inhibited the nuclear translocation of p65 and degradation of IκB-α in-duced by LPS, and the inhibitory effect of ABL was concentration-dependent. LPS increased the binding of nuclear extracts from VSMC induced by LPS to double strands oligonucleotide probe containing NF-κB binding site using EMSA. The shift bands were abolished when a 100-fold excess of unlabeled NF-κB oligonucleotide probe was included. Pretreatment with ABL significantly reduced the nuclear level of NF-κB and declined the binding activity of nuclear extracts with DNA probe induced by LPS. Furthermore, ABL consequentially inhibited the expression of NF-κB-dependent COX-2 gene induced by LPS.
CONCLUSIONS:
These results suggest that ABL may be one anti-inflammatory drug which inhibits the expression of COX-2 gene by blocking NF-κB activation and thus suppresses the inflammatory response to LPS in VSMC.

Protocol of 1-O-Acetyl britannilactone

Kinase Assay

1-o-acetylbritannilactone (ABL) inhibits angiogenesis and lung cancer cell growth through regulating VEGF-Src-FAK signaling.[Pubmed: 26102035]

Biochem Biophys Res Commun. 2015 Aug 21;464(2):422-7.

The search for safe, effective and affordable therapeutics against non-small cell lung cancer (NSCLC) and other lung cancers is important.
METHODS AND RESULTS:
Here we explored the potential effect of1-O-Acetyl britannilactone(ABL), a novel extract from Inula britannica-F, on angiogenesis and lung cancer cell growth. We demonstrated that ABL dose-dependently inhibited vascular endothelial growth factor (VEGF)-induced proliferation, migration, and capillary structure formation of cultured human umbilical vascular endothelial cells (HUVECs). In vivo, ABL administration suppressed VEGF-induced new vasculature formation in Matrigel plugs. For the mechanism investigations, we found that ABL largely inhibited VEGF-mediated activation of Src kinase and focal adhesion kinase (FAK) in HUVECs. Furthermore, treatment of A549 NSCLC cells with ABL resulted in cell growth inhibition and Src-FAK in-activation. Significantly, administration of a single dose of ABL (12 mg/kg/day) remarkably suppressed growth of A549 xenografts in nude mice. In vivo microvessels formation and Src activation were also significantly inhibited in ABL-treated xenograft tumors.
CONCLUSIONS:
Taken together, our findings suggest that ABL suppresses angiogenesis and lung cancer cell growth possibly via regulating the VEGFR-Src-FAK signaling.

Structure Identification
Se Pu. 2005 Nov;23(6):573-6.

Preparation and determination of 1-O-acetylbritannilactone in Inula Britannica L.[Pubmed: 16498983]

To prepare reference substance for quality control of Inula Britannica L., 1-O-Acetyl britannilactone was extracted and separated from chloroform extraction of Inula Britannica L.
METHODS AND RESULTS:
Chemical structure of the 1-O-acetylbritannilactone product was elucidated by ultraviolet spectrometry (UV), infrared spectroscopy (IR), nuclear magnetic resonance (NMR) and mass spectrometry (MS), and the results were in agreement with the reference. The purity of the 1-O-Acetyl britannilactone product was 99.5%, which satisfies the need of reference substances of traditional Chinese medicines. A method of high performance liquid chromatography-evaporative light scattering detection (HPLC-ELSD) is described for the determination of 1-O-Acetyl britannilactone in Inula Britannica L. The chromatographic conditions include Hypersil ODS-2 column, a mixture of methanol-water (52: 48, v/v) with the flow rate of 1.0 mL/min used as mobile phase. The temperature of drift tube of the ELSD was 90 degrees C. Flow rate of carrier gas was 2.5 L/min. Linear range of 1-O-Acetyl britannilactone was 1.37 - 8.21 microLg (r = 0.999 8). The average recovery of 1-O-acetylbritannilactone was 100.2% with the relative standard deviation (RSD) of 1.3% (n = 6).
CONCLUSIONS:
The method is simple, accurate, time saving and reproducible.

1-O-Acetyl britannilactone Dilution Calculator

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1-O-Acetyl britannilactone Molarity Calculator

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Preparing Stock Solutions of 1-O-Acetyl britannilactone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.2425 mL 16.2127 mL 32.4254 mL 64.8508 mL 81.0636 mL
5 mM 0.6485 mL 3.2425 mL 6.4851 mL 12.9702 mL 16.2127 mL
10 mM 0.3243 mL 1.6213 mL 3.2425 mL 6.4851 mL 8.1064 mL
50 mM 0.0649 mL 0.3243 mL 0.6485 mL 1.297 mL 1.6213 mL
100 mM 0.0324 mL 0.1621 mL 0.3243 mL 0.6485 mL 0.8106 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 1-O-Acetyl britannilactone

[Preparation and determination of 1-O-acetylbritannilactone in Inula Britannica L].[Pubmed:16498983]

Se Pu. 2005 Nov;23(6):573-6.

To prepare reference substance for quality control of Inula Britannica L., 1-O-acetylbritannilactone was extracted and separated from chloroform extraction of Inula Britannica L. Chemical structure of the 1-O-acetylbritannilactone product was elucidated by ultraviolet spectrometry (UV), infrared spectroscopy (IR), nuclear magnetic resonance (NMR) and mass spectrometry (MS), and the results were in agreement with the reference. The purity of the 1-O-acetylbritannilactone product was 99.5%, which satisfies the need of reference substances of traditional Chinese medicines. A method of high performance liquid chromatography-evaporative light scattering detection (HPLC-ELSD) is described for the determination of 1-O-acetylbritannilactone in Inula Britannica L. The chromatographic conditions include Hypersil ODS-2 column, a mixture of methanol-water (52: 48, v/v) with the flow rate of 1.0 mL/min used as mobile phase. The temperature of drift tube of the ELSD was 90 degrees C. Flow rate of carrier gas was 2.5 L/min. Linear range of 1-O-acetylbritannilactone was 1.37 - 8.21 microLg (r = 0.999 8). The average recovery of 1-O-acetylbritannilactone was 100.2% with the relative standard deviation (RSD) of 1.3% (n = 6). The method is simple, accurate, time saving and reproducible.

1-o-acetylbritannilactone (ABL) inhibits angiogenesis and lung cancer cell growth through regulating VEGF-Src-FAK signaling.[Pubmed:26102035]

Biochem Biophys Res Commun. 2015 Aug 21;464(2):422-7.

The search for safe, effective and affordable therapeutics against non-small cell lung cancer (NSCLC) and other lung cancers is important. Here we explored the potential effect of 1-o-acetylbritannilactone (ABL), a novel extract from Inula britannica-F, on angiogenesis and lung cancer cell growth. We demonstrated that ABL dose-dependently inhibited vascular endothelial growth factor (VEGF)-induced proliferation, migration, and capillary structure formation of cultured human umbilical vascular endothelial cells (HUVECs). In vivo, ABL administration suppressed VEGF-induced new vasculature formation in Matrigel plugs. For the mechanism investigations, we found that ABL largely inhibited VEGF-mediated activation of Src kinase and focal adhesion kinase (FAK) in HUVECs. Furthermore, treatment of A549 NSCLC cells with ABL resulted in cell growth inhibition and Src-FAK in-activation. Significantly, administration of a single dose of ABL (12 mg/kg/day) remarkably suppressed growth of A549 xenografts in nude mice. In vivo microvessels formation and Src activation were also significantly inhibited in ABL-treated xenograft tumors. Taken together, our findings suggest that ABL suppresses angiogenesis and lung cancer cell growth possibly via regulating the VEGFR-Src-FAK signaling.

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