Aconine

CAS# 509-20-6

Aconine

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Quality Control of Aconine

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Chemical structure

Aconine

3D structure

Chemical Properties of Aconine

Cas No. 509-20-6 SDF Download SDF
PubChem ID 10511 Appearance White-pale yellow powder
Formula C25H41NO9 M.Wt 499.60
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Jesaconine
Solubility DMSO : ≥ 125 mg/mL (250.21 mM)
*"≥" means soluble, but saturation unknown.
SMILES CCN1CC2(C(CC(C34C2C(C(C31)C5(C6C4CC(C6O)(C(C5O)OC)O)O)OC)OC)O)COC
Standard InChIKey SQMGCPHFHQGPIF-RCXDTZIBSA-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 Aconine

The roots of Aconitum kusnezoffii Reichb.

Biological Activity of Aconine

DescriptionAconine can inhibit RANKL-induced osteoclast differentiation in RAW264.7 cells by suppressing NF-κB and NFATc1 activation and DC-STAMP expression. Aconine can attenuate hepatic fat degeneration of rats with fatty liver induced by high-fat diet through decreasing TG,TC deposit in liver.
TargetsNF-kB | NOS | MMP(e.g.TIMP)
In vitro

[Effects of steaming and baking on content of alkaloids in Aconite Lateralis Radix (Fuzi)].[Pubmed: 25898581]

Zhongguo Zhong Yao Za Zhi. 2014 Dec;39(24):4798-803.

To study the effect of steaming and baking process on contents of alkaloids in Aconite Lateralis Radix (Fuzi),
METHODS AND RESULTS:
13 alkaloids were analyzed by UPLC-MS/MS equipped with ESI ion source in MRM mode. In steaming process, the contents of diester-diterpenoid alkaloids decreased rapidly, the contents of monoester-diterpenoid alkaloids firstly increased, reached the peak at 40 min, and then deceased gradually. The contents of Aconine alkaloids (mesAconine, Aconine and hypAconine) increased all the time during processing, while the contents of fuziline, songorine, karacoline, salsolionl were stable or slightly decreased. In baking process, dynamic variations of alkaloids were different from that in the steaming process. Diester-diterpenoid alkaloids were degraded slightly slower than in steaming process. Monoester-diterpenoid alkaloids, Aconine alkaloids and the total alkaloids had been destroyed at different degrees, their contents were significantly lower than the ones in steaming Fuzi at the same processing time. This experiment revealed the dynamic variations of alkaloids in the course of steaming and baking.
CONCLUSIONS:
Two processing methods which can both effectively remove the toxic ingredients and retain the active ingredients are simple and controllable, and are valuable for popularization and application.

Aconine inhibits RANKL-induced osteoclast differentiation in RAW264.7 cells by suppressing NF-κB and NFATc1 activation and DC-STAMP expression.[Pubmed: 26592521]

Acta Pharmacol Sin. 2016 Feb; 37(2): 255–263.

Aconiti Lateralis Radix Preparata is a traditional Chinese medicine used to treat chronic arthritis and is highly effective against rheumatoid arthritis. However, the effects of Aconine, a derivative of aconitum alkaloids, on osteoclasts, which can absorb bone, remain unknown. Here, we investigated the effects of Aconine on osteoclast differentiation and bone resorption in vitro.
METHODS AND RESULTS:
The viability of mouse leukemic monocyte/macrophage cell line RAW264.7 was measured using CCK-8 assays. Osteoclast differentiation was induced by incubation of RAW264.7 cells in the presence of RANKL, and assessed with TRAP staining assay. Bone resorption was examined with bone resorption pits assay. The expression of relevant genes and proteins was analyzed using RT-PCR and Western blots. The activation of NF-κB and nuclear factor of activated T-cells (NFAT) was examined using stable NF-κB and NFATc1 luciferase reporter gene systems, RT-PCR and Western blot analysis. Aconine (0.125, 0.25 μmol/L) did not affect the viability of RAW264.7 cells, but dose-dependently inhibited RANKL-induced osteoclast formation and bone resorptive activity. Furthermore, Aconine dose-dependently inhibited the RANKL-induced activation of NF-κB and NFATc1 in RAW264.7 cells, and subsequently reduced the expression of osteoclast-specific genes (c-Src, β3-Integrin, cathepsin K and MMP-9) and the expression of dendritic cell-specific transmembrane protein (DC-STAMP), which played an important role in cell-cell fusion.
CONCLUSIONS:
These findings suggest that Aconine inhibits RANKL-induced osteoclast differentiation in RAW264.7 cells by suppressing the activation of NF-κB and NFATc1 and the expression of the cell-cell fusion molecule DC-STAMP.

Protocol of Aconine

Structure Identification
Nat Prod Commun. 2014 Jun;9(6):785-6.

Ring A conformation of aconine and pseudaconine in CDCl3.[Pubmed: 25115078]


METHODS AND RESULTS:
On the basis of intensive interpretation of the 1H NMR spectroscopic data, the ring A conformation of Aconine (1) was speculated as twist boat in CDCl3, and as chair or twist boat in acetone-d6 and pyridine-d5. The ring A of pseudAconine (2) adopts the chair conformation in CDCl3, acetone-d6, and pyridine-ds. Accordingly, the boat conformation of ring A in these two diterpenoid alkaloids in CDCl3 reported in the literature [1] should be revised.
CONCLUSIONS:
The difference in 13C NMR data for the same compound (1 or 2) in two different solvents (CDCl3, pyridine-d5) can be attributed to solvent effects.

Aconine Dilution Calculator

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Aconine Molarity Calculator

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Preparing Stock Solutions of Aconine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0016 mL 10.008 mL 20.016 mL 40.032 mL 50.04 mL
5 mM 0.4003 mL 2.0016 mL 4.0032 mL 8.0064 mL 10.008 mL
10 mM 0.2002 mL 1.0008 mL 2.0016 mL 4.0032 mL 5.004 mL
50 mM 0.04 mL 0.2002 mL 0.4003 mL 0.8006 mL 1.0008 mL
100 mM 0.02 mL 0.1001 mL 0.2002 mL 0.4003 mL 0.5004 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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Background on Aconine

Aconine inhibits receptor activator of nuclear factor (NF)-κB ligand (RANKL)-induced NF-κB activation.

In Vitro:Treatment with Aconine significantly inhibits the RANKL-induced transcriptional activity of NF-κB in a dose-dependent manner. Aconine inhibits RANKL-induced osteoclast differentiation in RAW264.7 cells by suppressing the activation of NF-κB and NFATc1 and the expression of the cell-cell fusion molecule DC-STAMP. Aconine (0.125, 0.25 μM) does not affect the viability of RAW264.7 cells, but dose-dependently inhibits RANKL-induced osteoclast formation and bone resorptive activity. Aconine dose-dependently inhibits the RANKL-induced activation of NF-κB and NFATc1 in RAW264.7 cells, and subsequently reduces the expression of osteoclast-specific genes (c-Src, β3-Integrin, cathepsin K and MMP-9) and the expression of dendritic cell-specific transmembrane protein (DC-STAMP), which plays an important role in cell-cell fusion[1].

References:
[1]. Zeng XZ, et al. Aconine inhibits RANKL-induced osteoclast differentiation in RAW264.7 cells by suppressing NF-κB and NFATc1 activation and DC-STAMP expression. Acta Pharmacol Sin. 2016 Feb;37(2):255-63.

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References on Aconine

Selective estimation of aconitine in presence of aconine and benzoylaconine.[Pubmed:903876]

J Pharm Sci. 1977 Sep;66(9):1331-2.

A selective and simple colorimetric method is presented for the estimation of aconitine in drugs in the presence of Aconine and benzoylAconine. The method is based on the formation of an iron hydroxamate complex through the acetate ester group to which the biological activity is due. The color is measured at 530 nm (5--250 microgram/ml). Under the experimental conditions, neither the benzoyl group of benzoylAconine nor Aconine is involved in the process of hydroxylaminolysis.

Ring A conformation of aconine and pseudaconine in CDCl3.[Pubmed:25115078]

Nat Prod Commun. 2014 Jun;9(6):785-6.

On the basis of intensive interpretation of the 1H NMR spectroscopic data, the ring A conformation of Aconine (1) was speculated as twist boat in CDCl3, and as chair or twist boat in acetone-d6 and pyridine-d5. The ring A of pseudAconine (2) adopts the chair conformation in CDCl3, acetone-d6, and pyridine-ds. Accordingly, the boat conformation of ring A in these two diterpenoid alkaloids in CDCl3 reported in the literature [1] should be revised. The difference in 13C NMR data for the same compound (1 or 2) in two different solvents (CDCl3, pyridine-d5) can be attributed to solvent effects.

[Effects of steaming and baking on content of alkaloids in Aconite Lateralis Radix (Fuzi)].[Pubmed:25898581]

Zhongguo Zhong Yao Za Zhi. 2014 Dec;39(24):4798-803.

To study the effect of steaming and baking process on contents of alkaloids in Aconite Lateralis Radix (Fuzi), 13 alkaloids were analyzed by UPLC-MS/MS equipped with ESI ion source in MRM mode. In steaming process, the contents of diester-diterpenoid alkaloids decreased rapidly, the contents of monoester-diterpenoid alkaloids firstly increased, reached the peak at 40 min, and then deceased gradually. The contents of Aconine alkaloids (mesAconine, Aconine and hypAconine) increased all the time during processing, while the contents of fuziline, songorine, karacoline, salsolionl were stable or slightly decreased. In baking process, dynamic variations of alkaloids were different from that in the steaming process. Diester-diterpenoid alkaloids were degraded slightly slower than in steaming process. Monoester-diterpenoid alkaloids, Aconine alkaloids and the total alkaloids had been destroyed at different degrees, their contents were significantly lower than the ones in steaming Fuzi at the same processing time. This experiment revealed the dynamic variations of alkaloids in the course of steaming and baking. Two processing methods which can both effectively remove the toxic ingredients and retain the active ingredients are simple and controllable, and are valuable for popularization and application.

Aconine inhibits RANKL-induced osteoclast differentiation in RAW264.7 cells by suppressing NF-kappaB and NFATc1 activation and DC-STAMP expression.[Pubmed:26592521]

Acta Pharmacol Sin. 2016 Feb;37(2):255-63.

AIM: Aconiti Lateralis Radix Preparata is a traditional Chinese medicine used to treat chronic arthritis and is highly effective against rheumatoid arthritis. However, the effects of Aconine, a derivative of aconitum alkaloids, on osteoclasts, which can absorb bone, remain unknown. Here, we investigated the effects of Aconine on osteoclast differentiation and bone resorption in vitro. METHODS: The viability of mouse leukemic monocyte/macrophage cell line RAW264.7 was measured using CCK-8 assays. Osteoclast differentiation was induced by incubation of RAW264.7 cells in the presence of RANKL, and assessed with TRAP staining assay. Bone resorption was examined with bone resorption pits assay. The expression of relevant genes and proteins was analyzed using RT-PCR and Western blots. The activation of NF-kappaB and nuclear factor of activated T-cells (NFAT) was examined using stable NF-kappaB and NFATc1 luciferase reporter gene systems, RT-PCR and Western blot analysis. RESULTS: Aconine (0.125, 0.25 mumol/L) did not affect the viability of RAW264.7 cells, but dose-dependently inhibited RANKL-induced osteoclast formation and bone resorptive activity. Furthermore, Aconine dose-dependently inhibited the RANKL-induced activation of NF-kappaB and NFATc1 in RAW264.7 cells, and subsequently reduced the expression of osteoclast-specific genes (c-Src, beta3-Integrin, cathepsin K and MMP-9) and the expression of dendritic cell-specific transmembrane protein (DC-STAMP), which played an important role in cell-cell fusion. CONCLUSION: These findings suggest that Aconine inhibits RANKL-induced osteoclast differentiation in RAW264.7 cells by suppressing the activation of NF-kappaB and NFATc1 and the expression of the cell-cell fusion molecule DC-STAMP.

Description

Aconine inhibits receptor activator of nuclear factor (NF)-κB ligand (RANKL)-induced NF-κB activation.

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