Linderane

CAS# 13476-25-0

Linderane

2D Structure

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Quality Control of Linderane

3D structure

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Linderane

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Chemical Properties of Linderane

Cas No. 13476-25-0 SDF Download SDF
PubChem ID 6915739 Appearance White powder
Formula C15H16O4 M.Wt 260.28
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in chloroform
SMILES CC1=CCCC23C(O2)C(C4=C(C1)OC=C4C)OC3=O
Standard InChIKey KBMSVODXFLAQNJ-DXGHHDSJSA-N
Standard InChI InChI=1S/C15H16O4/c1-8-4-3-5-15-13(19-15)12(18-14(15)16)11-9(2)7-17-10(11)6-8/h4,7,12-13H,3,5-6H2,1-2H3/b8-4+/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 Linderane

The roots of Lindera aggregata( Sims) Kosterm

Biological Activity of Linderane

DescriptionLinderane is a mechanism-based inactivator of CYP2C9.
TargetsP450 (e.g. CYP17) | NADPH-oxidase
In vitro

Mechanism-based inactivation of CYP2C9 by linderane.[Pubmed: 26068520]

Xenobiotica. 2015 Jun 11:1-10.

1. Linderane (LDR), a furan-containing sesquiterpenoid, is found in Lindera aggregata (Sims) Kosterm, a common traditional Chinese herbal medicine. We thoroughly studied the irreversible inhibitory effect of LDR on cytochrome P450 2C9 (CYP2C9).
METHODS AND RESULTS:
2. LDR caused a time- and concentration-dependent inactivation of CYP2C9. In addition, the inactivation of CYP2C9 by LDR was NADPH-dependent and irreversible. More than 50% of CYP2C9 activity was lost after its incubation with LDR at the concentration of 10 μM for 15 min at 30 °C. The maximal rate constant for inactivation (kinact) was found to be 0.0419 min(-1), and the concentration required for half-maximal inactivation (KI) was 1.26 μM, respectively. Glutathione (GSH), catalase, and superoxide dismutase (SOD) failed to protect CYP2C9 against inactivation by LDR. Diclofenac, a substrate of CYP2C9, prevented the enzyme from inactivation produced by LDR. The estimated partition ratio of the inactivation was approximately 227. 3. Two reactive intermediates, including furanoepoxide and γ-ketoenal, might be responsible for the observed enzyme inactivation. The formation of the intermediates was verified by chemical synthesis.
CONCLUSIONS:
Multiple P450 enzymes, including CYPs 1A2, 2B6, 2C9, 2C19, 2D6, 3A4, and 3A5, were found to be involved in the metabolic activation of LDR. In conclusion, LDR was characterized as a mechanism-based inactivator of CYP2C9.

Protocol of Linderane

Structure Identification
Zhongguo Zhong Yao Za Zhi. 2004 Jul;29(7):657-9.

Determination of linderane in root tuber of Lindera aggregata by HPLC[Pubmed: 15503773]

To provide scientific basis for quality control of Lindera aggregata.
METHODS AND RESULTS:
HPLC analytical method was established using a Lichrospher C18 column and acetonitrile-water (56:44) as the mobile phase, detected at 235 nm. The linear range of Linderane is between 0.0642 - 0.5774 microg, the average recovery was 98.4%, RSD1.7% (n = 9).
CONCLUSIONS:
Contents of Linderane in commercially available and collected samples were from 0.028% to 0.123% and from 0.056% to 0.222% respectively.

Linderane Dilution Calculator

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Linderane Molarity Calculator

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Preparing Stock Solutions of Linderane

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.842 mL 19.2101 mL 38.4202 mL 76.8403 mL 96.0504 mL
5 mM 0.7684 mL 3.842 mL 7.684 mL 15.3681 mL 19.2101 mL
10 mM 0.3842 mL 1.921 mL 3.842 mL 7.684 mL 9.605 mL
50 mM 0.0768 mL 0.3842 mL 0.7684 mL 1.5368 mL 1.921 mL
100 mM 0.0384 mL 0.1921 mL 0.3842 mL 0.7684 mL 0.9605 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 Linderane

[Determination of linderane in root tuber of Lindera aggregata by HPLC].[Pubmed:15503773]

Zhongguo Zhong Yao Za Zhi. 2004 Jul;29(7):657-9.

OBJECTIVE: To provide scientific basis for quality control of Lindera aggregata. METHOD: HPLC analytical method was established using a Lichrospher C18 column and acetonitrile-water (56:44) as the mobile phase, detected at 235 nm. RESULT: The linear range of Linderane is between 0.0642 - 0.5774 microg, the average recovery was 98.4%, RSD1.7% (n = 9). CONCLUSION: Contents of Linderane in commercially available and collected samples were from 0.028% to 0.123% and from 0.056% to 0.222% respectively.

Mechanism-based inactivation of CYP2C9 by linderane.[Pubmed:26068520]

Xenobiotica. 2015;45(12):1037-46.

1. Linderane (LDR), a furan-containing sesquiterpenoid, is found in Lindera aggregata (Sims) Kosterm, a common traditional Chinese herbal medicine. We thoroughly studied the irreversible inhibitory effect of LDR on cytochrome P450 2C9 (CYP2C9). 2. LDR caused a time- and concentration-dependent inactivation of CYP2C9. In addition, the inactivation of CYP2C9 by LDR was NADPH-dependent and irreversible. More than 50% of CYP2C9 activity was lost after its incubation with LDR at the concentration of 10 muM for 15 min at 30 degrees C. The maximal rate constant for inactivation (kinact) was found to be 0.0419 min(-1), and the concentration required for half-maximal inactivation (KI) was 1.26 muM, respectively. Glutathione (GSH), catalase, and superoxide dismutase (SOD) failed to protect CYP2C9 against inactivation by LDR. Diclofenac, a substrate of CYP2C9, prevented the enzyme from inactivation produced by LDR. The estimated partition ratio of the inactivation was approximately 227. 3. Two reactive intermediates, including furanoepoxide and gamma-ketoenal, might be responsible for the observed enzyme inactivation. The formation of the intermediates was verified by chemical synthesis. Multiple P450 enzymes, including CYPs 1A2, 2B6, 2C9, 2C19, 2D6, 3A4, and 3A5, were found to be involved in the metabolic activation of LDR. In conclusion, LDR was characterized as a mechanism-based inactivator of CYP2C9.

Description

Linderane, isolated from the root of Lindera strychnifolia, is an irreversible inhibitor cytochrome P450 2C9 (CYP2C9). Linderane has the potential to relieve pain and cramp.

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