Lycodoline

CAS# 6900-92-1

Lycodoline

Catalog No. BCN2506----Order now to get a substantial discount!

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Quality Control of Lycodoline

Number of papers citing our products

Chemical structure

Lycodoline

3D structure

Chemical Properties of Lycodoline

Cas No. 6900-92-1 SDF Download SDF
PubChem ID 12312555 Appearance Cryst.
Formula C16H25NO2 M.Wt 263.38
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC1CC2CC(=O)C3CCCN4C3(C1)C2(CCC4)O
Standard InChIKey DBMXKPOCXQNWOQ-WALBABNVSA-N
Standard InChI InChI=1S/C16H25NO2/c1-11-8-12-9-14(18)13-4-2-6-17-7-3-5-16(12,19)15(13,17)10-11/h11-13,19H,2-10H2,1H3/t11-,12+,13-,15+,16+/m1/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 Lycodoline

The herbs of Lycopodium japonicum Thunb.

Biological Activity of Lycodoline

In vitro

Acetylcholinesterase inhibitory activity of lycopodane-type alkaloids from the Icelandic Lycopodium annotinum ssp. alpestre.[Pubmed: 19939421]

Phytochemistry. 2010 Feb;71(2-3):149-57.

The aim of this study was to investigate structures and acetylcholinesterase inhibitory activities of lycopodane-type alkaloids isolated from an Icelandic collection of Lycopodium annotinum ssp. alpestre. Ten alkaloids were isolated, including annotinine, annotine, Lycodoline, lycoposerramine M, anhydroLycodoline, gnidioidine, lycofoline, lannotinidine D, and acrifoline, as well as a previously unknown N-oxide of annotine.
METHODS AND RESULTS:
1H and 13C NMR data of several of the alkaloids were provided for the first time. Solvent-dependent equilibrium constants between ketone and hemiketal form of acrifoline were determined. Conformation of acrifoline was characterized using NOESY spectroscopy and molecular modelling. The isolated alkaloids were evaluated for their in vitro inhibitory activity against acetylcholinesterase and butyrylcholinesterase. Ligand docking studies based on mutated 3D structure of Torpedo californica acetylcholinesterase provided rationale for low inhibitory activity of the isolated alkaloids as compared to huperzine A or B, which are potent acetylcholinesterase inhibitors belonging to the lycodine class. Based on the modelling studies the lycopodane-type alkaloids seem to fit well into the active site gorge of the enzyme but the position of their functional groups is not compatible with establishing strong hydrogen bonding interactions with the amino acid residues that line the binding site.
CONCLUSIONS:
The docking studies indicate possibilities of additional functionalization of the lycopodane skeleton to render potentially more active analogues.

Protocol of Lycodoline

Structure Identification
Zhongguo Zhong Yao Za Zhi. 2012 Feb;37(4):475-7.

Study on chemical constituents of Lycopodium alkaloids[Pubmed: 22667147]

To study the alkaloid chemical constituents of Lycopodium japonicum.
METHODS AND RESULTS:
Compounds were isolated and purified by such methods as silica gel column chromatography, RP-C18 reversed phase column chromatography, Sephadex LH-20 column chromatography and Waters semi-preparative liquid chromatogram, and their structures were identified based on physicochemical property and spectrum data. Nine known alkaloid chemical constituents were isolated and identified, they were Lycodoline (1), lucidioline (2), alpha-obscurine (3), lycopodine (4), lycoposerramine-L (5), lycoposerramine-M (6), 11alpha-O-acetyl-lycopodine (7), des-N-methyl-a-obscurine (8), clavolonine (9).
CONCLUSIONS:
Compounds 4-9 were obtained from L. japonicum for the first time.

Lycodoline Dilution Calculator

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Lycodoline Molarity Calculator

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Preparing Stock Solutions of Lycodoline

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.7968 mL 18.984 mL 37.968 mL 75.9359 mL 94.9199 mL
5 mM 0.7594 mL 3.7968 mL 7.5936 mL 15.1872 mL 18.984 mL
10 mM 0.3797 mL 1.8984 mL 3.7968 mL 7.5936 mL 9.492 mL
50 mM 0.0759 mL 0.3797 mL 0.7594 mL 1.5187 mL 1.8984 mL
100 mM 0.038 mL 0.1898 mL 0.3797 mL 0.7594 mL 0.9492 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 Lycodoline

[Study on chemical constituents of Lycopodium alkaloids].[Pubmed:22667147]

Zhongguo Zhong Yao Za Zhi. 2012 Feb;37(4):475-7.

OBJECTIVE: To study the alkaloid chemical constituents of Lycopodium japonicum. METHOD: Compounds were isolated and purified by such methods as silica gel column chromatography, RP-C18 reversed phase column chromatography, Sephadex LH-20 column chromatography and Waters semi-preparative liquid chromatogram, and their structures were identified based on physicochemical property and spectrum data. RESULT: Nine known alkaloid chemical constituents were isolated and identified, they were Lycodoline (1), lucidioline (2), alpha-obscurine (3), lycopodine (4), lycoposerramine-L (5), lycoposerramine-M (6), 11alpha-O-acetyl-lycopodine (7), des-N-methyl-a-obscurine (8), clavolonine (9). CONCLUSION: Compounds 4-9 were obtained from L. japonicum for the first time.

Acetylcholinesterase inhibitory activity of lycopodane-type alkaloids from the Icelandic Lycopodium annotinum ssp. alpestre.[Pubmed:19939421]

Phytochemistry. 2010 Feb;71(2-3):149-57.

The aim of this study was to investigate structures and acetylcholinesterase inhibitory activities of lycopodane-type alkaloids isolated from an Icelandic collection of Lycopodium annotinum ssp. alpestre. Ten alkaloids were isolated, including annotinine, annotine, Lycodoline, lycoposerramine M, anhydroLycodoline, gnidioidine, lycofoline, lannotinidine D, and acrifoline, as well as a previously unknown N-oxide of annotine. 1H and 13C NMR data of several of the alkaloids were provided for the first time. Solvent-dependent equilibrium constants between ketone and hemiketal form of acrifoline were determined. Conformation of acrifoline was characterized using NOESY spectroscopy and molecular modelling. The isolated alkaloids were evaluated for their in vitro inhibitory activity against acetylcholinesterase and butyrylcholinesterase. Ligand docking studies based on mutated 3D structure of Torpedo californica acetylcholinesterase provided rationale for low inhibitory activity of the isolated alkaloids as compared to huperzine A or B, which are potent acetylcholinesterase inhibitors belonging to the lycodine class. Based on the modelling studies the lycopodane-type alkaloids seem to fit well into the active site gorge of the enzyme but the position of their functional groups is not compatible with establishing strong hydrogen bonding interactions with the amino acid residues that line the binding site. The docking studies indicate possibilities of additional functionalization of the lycopodane skeleton to render potentially more active analogues.

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