Isolinderalactone

CAS# 957-66-4

Isolinderalactone

2D Structure

Catalog No. BCN1252----Order now to get a substantial discount!

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Quality Control of Isolinderalactone

3D structure

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Isolinderalactone

Number of papers citing our products

Chemical Properties of Isolinderalactone

Cas No. 957-66-4 SDF Download SDF
PubChem ID 5318587 Appearance Powder
Formula C15H16O3 M.Wt 244.29
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3aS,4R,8bR)-4-ethenyl-4,8-dimethyl-3-methylidene-5,8b-dihydro-3aH-furo[2,3-e][1]benzofuran-2-one
SMILES CC1=COC2=C1C3C(C(=C)C(=O)O3)C(C2)(C)C=C
Standard InChIKey VXZIFOKTSURLNL-YDHLFZDLSA-N
Standard InChI InChI=1S/C15H16O3/c1-5-15(4)6-10-11(8(2)7-17-10)13-12(15)9(3)14(16)18-13/h5,7,12-13H,1,3,6H2,2,4H3/t12-,13-,15-/m0/s1
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 Isolinderalactone

The roots of Lindera aggregata

Biological Activity of Isolinderalactone

DescriptionIsolinderalactone shows anti-inflammatory and anticancer capacity, it induces apoptosis in MDA-MB-231 cells and suppresses STAT3 signaling pathway through regulation of SOCS3 and miR-30c, may become a novel treatment for triple-negative breast cancer in the future; it exhibits moderate iNOS inhibitory activity, with the IC50 value of 0.30 uM.
Targetsp21 | NOS | Caspase | STAT | SOCS3 | miR-30c
In vitro

Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity.[Pubmed: 22148193]

J Nat Prod. 2011 Dec 27;74(12):2489-96.

Bioassay-guided fractionation of the roots of Neolitsea daibuensis afforded three new β-carboline alkaloids, daibucarbolines A-C (1-3), three new sesquiterpenoids, daibulactones A and B (4 and 5) and daibuoxide (6), and 20 known compounds.
METHODS AND RESULTS:
The structures of 1-6 were determined by spectroscopic analysis and single-crystal X-ray diffraction. Daibucarboline A (1), Isolinderalactone (7), 7-O-methylnaringenin (8), and prunetin (9) exhibited moderate iNOS inhibitory activity, with IC₅₀ values of 18.41, 0.30, 19.55, and 10.50 μM, respectively.

Isolinderalactone enhances the inhibition of SOCS3 on STAT3 activity by decreasing miR-30c in breast cancer.[Pubmed: 26707189]

Oncol Rep. 2016 Mar;35(3):1356-64.

Development of an efficient treatment for triple-negative breast cancer is an urgent issues. Compounds from plant extracts are a potential source of novel cancer treatment. Isolinderalactone, a kind of sesquiterpenoids compound, was purified from the root of Lindera strychnifolia and Neolitsea daibuensis and shows anti-inflammatory and anticancer capacity.
METHODS AND RESULTS:
In the present study, Isolinderalactone induced apoptosis in MDA-MB-231 cells which is a kind of triple-negative breast cancer cell line through induction of an intrinsic mitochondria-mediated and caspase-independent cell death. Treatment of Isolinderalactone increased the protein level of the suppressor of cytokine signaling 3 (SCOS3), decreased phosphorylation of the signal transducer and activator of transcription 3 (STAT3), and suppressed expression of the down-stream genes of the X-linked inhibitor of apoptosis protein in MDA-MB-231 cells. Our results further showed that the level of SOCS3 expression was induced by Isolinderalactone due to inhibiting the microRNA hsa-miR-30c-5p (miR-30c) expression. In addition, intraperitoneal injection of Isolinderalactone induced apoptosis in a xenograft breast tumor while it did not significantly affect the histology of liver, kidney and lung of the treated mice.
CONCLUSIONS:
In conclusion, Isolinderalactone induces apoptosis in MDA-MB‑231 cells and suppresses STAT3 signaling pathway through regulation of SOCS3 and miR-30c. It may become a novel treatment for triple-negative breast cancer in the future.

Protocol of Isolinderalactone

Kinase Assay

Isolinderalactone inhibits proliferation of A549 human non‑small cell lung cancer cells by arresting the cell cycle at the G0/G1 phase and inducing a Fas receptor and soluble Fas ligand-mediated apoptotic pathway.[Pubmed: 24604009]

Mol Med Rep. 2014 May;9(5):1653-9.

Lung cancer is currently the leading cause of cancer-related mortality worldwide. In Taiwan, lung cancer is also the type of malignancy that is the major cause of cancer-mortality. Investigating the mechanism of apoptosis of lung cancer cells is important in the treatment of lung cancer.
METHODS AND RESULTS:
In the present study, Isolinderalactone was demonstrated to exhibit anticancer effects in A549 human non-small cell lung cancer cells. The effect of Isolinderalactone on apoptosis, cell cycle distribution p21 levels and the Fas receptor and soluble Fas ligand (sFasL) were assayed in order to determine the mechanism underlying the anticancer effect of Isolinderalactone. It was demonstrated that Isolinderalactone may induce p21 expression and then cause the cell cycle arrest of A549 cells. The data of the present study also revealed that the Fas/sFasL apoptotic system is significant in the mechanism of Isolinderalactone‑induced apoptosis of A549 cells.
CONCLUSIONS:
These novel findings demonstrated that Isolinderalactone may cause the cell cycle arrest of A549 cells by induction of p21, and induce apoptosis of A549 human non-small-cell lung carcinoma cells through the Fas/sFasL apoptotic system.

Structure Identification
Chem Cent J. 2013 Jul 30;7(1):131.

Quantitative analysis of the major constituents in Chinese medicinal preparation SuoQuan formulae by ultra fast high performance liquid chromatography/quadrupole tandem mass spectrometry.[Pubmed: 23899222]

The SuoQuan formulae containing Fructus Alpiniae Oxyphyllae has been used to combat the urinary incontinence symptoms including frequency, urgency and nocturia for hundreds of years in China. However, the chemical information was not well characterized. The quality control marker constituent only focused on one single compound in the current Chinese Pharmacopeia. Hence it is prudent to identify and quantify the main constituents in this herbal product. This study aimed to analyze the main constituents using ultra-fast performance liquid chromatography coupled to tandem mass spectrometry (UFLC-MS/MS).
METHODS AND RESULTS:
Fourteen phytochemicals originated from five chemical classes constituents were identified by comparing the molecular mass, fragmentation pattern and retention time with those of the reference standards. A newly developed UFLC-MS/MS was validated demonstrating that the new assay was valid, reproducible and reliable. This method was successfully applied to simultaneously quantify the fourteen phytochemicals. Notably, the content of these constituents showed significant differences in three pharmaceutical preparations. The major constituent originated from each of chemical class was Isolinderalactone, norisoboldine, nootkatone, yakuchinone A and apigenin-4',7-dimethylther, respectively. The variation among these compounds was more than 1000 times. Furthermore, the significant content variation between the two different Suoquan pills was also observed.
CONCLUSIONS:
The proposed method is sensitive and reliable; hence it can be used to analyze a variety of SuoQuan formulae products produced by different pharmaceutical manufacturers.

Isolinderalactone Dilution Calculator

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Preparing Stock Solutions of Isolinderalactone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.0935 mL 20.4675 mL 40.935 mL 81.8699 mL 102.3374 mL
5 mM 0.8187 mL 4.0935 mL 8.187 mL 16.374 mL 20.4675 mL
10 mM 0.4093 mL 2.0467 mL 4.0935 mL 8.187 mL 10.2337 mL
50 mM 0.0819 mL 0.4093 mL 0.8187 mL 1.6374 mL 2.0467 mL
100 mM 0.0409 mL 0.2047 mL 0.4093 mL 0.8187 mL 1.0234 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 Isolinderalactone

Isolinderalactone inhibits proliferation of A549 human nonsmall cell lung cancer cells by arresting the cell cycle at the G0/G1 phase and inducing a Fas receptor and soluble Fas ligand-mediated apoptotic pathway.[Pubmed:24604009]

Mol Med Rep. 2014 May;9(5):1653-9.

Lung cancer is currently the leading cause of cancer-related mortality worldwide. In Taiwan, lung cancer is also the type of malignancy that is the major cause of cancer-mortality. Investigating the mechanism of apoptosis of lung cancer cells is important in the treatment of lung cancer. In the present study, Isolinderalactone was demonstrated to exhibit anticancer effects in A549 human non-small cell lung cancer cells. The effect of Isolinderalactone on apoptosis, cell cycle distribution p21 levels and the Fas receptor and soluble Fas ligand (sFasL) were assayed in order to determine the mechanism underlying the anticancer effect of Isolinderalactone. It was demonstrated that Isolinderalactone may induce p21 expression and then cause the cell cycle arrest of A549 cells. The data of the present study also revealed that the Fas/sFasL apoptotic system is significant in the mechanism of Isolinderalactoneinduced apoptosis of A549 cells. These novel findings demonstrated that Isolinderalactone may cause the cell cycle arrest of A549 cells by induction of p21, and induce apoptosis of A549 human non-small-cell lung carcinoma cells through the Fas/sFasL apoptotic system.

Quantitative analysis of the major constituents in Chinese medicinal preparation SuoQuan formulae by ultra fast high performance liquid chromatography/quadrupole tandem mass spectrometry.[Pubmed:23899222]

Chem Cent J. 2013 Jul 30;7(1):131.

BACKGROUND: The SuoQuan formulae containing Fructus Alpiniae Oxyphyllae has been used to combat the urinary incontinence symptoms including frequency, urgency and nocturia for hundreds of years in China. However, the chemical information was not well characterized. The quality control marker constituent only focused on one single compound in the current Chinese Pharmacopeia. Hence it is prudent to identify and quantify the main constituents in this herbal product. This study aimed to analyze the main constituents using ultra-fast performance liquid chromatography coupled to tandem mass spectrometry (UFLC-MS/MS). RESULTS: Fourteen phytochemicals originated from five chemical classes constituents were identified by comparing the molecular mass, fragmentation pattern and retention time with those of the reference standards. A newly developed UFLC-MS/MS was validated demonstrating that the new assay was valid, reproducible and reliable. This method was successfully applied to simultaneously quantify the fourteen phytochemicals. Notably, the content of these constituents showed significant differences in three pharmaceutical preparations. The major constituent originated from each of chemical class was Isolinderalactone, norisoboldine, nootkatone, yakuchinone A and apigenin-4',7-dimethylther, respectively. The variation among these compounds was more than 1000 times. Furthermore, the significant content variation between the two different Suoquan pills was also observed. CONCLUSION: The proposed method is sensitive and reliable; hence it can be used to analyze a variety of SuoQuan formulae products produced by different pharmaceutical manufacturers.

Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity.[Pubmed:22148193]

J Nat Prod. 2011 Dec 27;74(12):2489-96.

Bioassay-guided fractionation of the roots of Neolitsea daibuensis afforded three new beta-carboline alkaloids, daibucarbolines A-C (1-3), three new sesquiterpenoids, daibulactones A and B (4 and 5) and daibuoxide (6), and 20 known compounds. The structures of 1-6 were determined by spectroscopic analysis and single-crystal X-ray diffraction. Daibucarboline A (1), Isolinderalactone (7), 7-O-methylnaringenin (8), and prunetin (9) exhibited moderate iNOS inhibitory activity, with IC(5)(0) values of 18.41, 0.30, 19.55, and 10.50 muM, respectively.

Isolinderalactone enhances the inhibition of SOCS3 on STAT3 activity by decreasing miR-30c in breast cancer.[Pubmed:26707189]

Oncol Rep. 2016 Mar;35(3):1356-64.

Development of an efficient treatment for triple-negative breast cancer is an urgent issues. Compounds from plant extracts are a potential source of novel cancer treatment. Isolinderalactone, a kind of sesquiterpenoids compound, was purified from the root of Lindera strychnifolia and Neolitsea daibuensis and shows anti-inflammatory and anticancer capacity. In the present study, Isolinderalactone induced apoptosis in MDA-MB-231 cells which is a kind of triple-negative breast cancer cell line through induction of an intrinsic mitochondria-mediated and caspase-independent cell death. Treatment of Isolinderalactone increased the protein level of the suppressor of cytokine signaling 3 (SCOS3), decreased phosphorylation of the signal transducer and activator of transcription 3 (STAT3), and suppressed expression of the down-stream genes of the X-linked inhibitor of apoptosis protein in MDA-MB-231 cells. Our results further showed that the level of SOCS3 expression was induced by Isolinderalactone due to inhibiting the microRNA hsa-miR-30c-5p (miR-30c) expression. In addition, intraperitoneal injection of Isolinderalactone induced apoptosis in a xenograft breast tumor while it did not significantly affect the histology of liver, kidney and lung of the treated mice. In conclusion, Isolinderalactone induces apoptosis in MDA-MB231 cells and suppresses STAT3 signaling pathway through regulation of SOCS3 and miR-30c. It may become a novel treatment for triple-negative breast cancer in the future.

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