| Identification | Back Directory | [Name]
ACONINE | [CAS]
509-20-6 | [Synonyms]
ACONINE
Jesaconine
ACONINE USP/EP/BP
Aconine (Jesaconine)
20-ethyl-1,6,16-trimethoxy-4-(methoxymethyl)aconitane-3,8,13...
20-Ethyl-1α,6α,16β-trimethoxy-4-(methoxymethyl)aconitane-3α,8,13,14α,15α-pentol
(15S,16S)-20-Ethyl-1α,6α,16-trimethoxy-4-(methoxymethyl)aconitane-3α,8β,13β,14α,15-pentol
Aconitane-3,8,13,14,15-pentol,20-ethyl-1,6,16-trimethoxy-4-(methoxymethyl)-, (1a,3a,6a,14a,15a,16b)-
Aconitane-3,8,13,14,15-pentol, 20-ethyl-1,6,16-trimethoxy-4-(methoxymethyl)-, (1α,3α,6α,14α,15α,16β)-
(1alpha,3alpha,6alpha,14alpha,15alpha,16beta)-20-Ethyl-1,6,16-trimethoxy-4-(methoxymethyl)aconitane-3,8,13,14,15-pentol | [Molecular Formula]
C25H41NO9 | [MDL Number]
MFCD01673464 | [MOL File]
509-20-6.mol | [Molecular Weight]
499.597 |
| Chemical Properties | Back Directory | [Melting point ]
129-131℃ | [alpha ]
D +23° | [Boiling point ]
590.79°C (rough estimate) | [density ]
1.42 | [refractive index ]
1.6000 (estimate) | [storage temp. ]
-20°C Freezer | [solubility ]
Chloroform (Slightly), DMSO (Slightly) | [form ]
Solid | [pka]
9.52(at 25℃) | [color ]
Off-White to Pale Yellow |
| Questions And Answer | Back Directory | [Toxicity]
In vivo, aconine is toxic to mice when administered intravenously at a dose of 120 mg/kg. It induces flaccid paralysis and toxicity in rats with toxic dose (TD50) and LD50 values of 1.5 and 1.7 μmol per animal, respectively.
| [Description]
Aconine is an alkaloid originally isolated from Aconitum species and active metabolite of aconitine. It inhibits osteoclast differentiation of RANKL-stimulated RAW 264.7 cells and bone resorption in a pit formation assay in a concentration-dependent manner. Aconine also inhibits RANKL-induced activation of NF-κB and NFATc1 in RAW 264.7 cells.
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| Hazard Information | Back Directory | [Uses]
Aconine is a derivative of Aconitine (A189875), a neurotoxin which activates tetrodotoxin-sensitive Na+ channels, inducing presynaptic depolarization, thus blocking the nerve action potential which, in turn, blocks the release of neurotransmitters and decreases the end plate potential at the neuromuscular junction. | [Definition]
ChEBI: Aconine is a diterpene alkaloid with formula C25H41NO9 that is isolated from several Aconitum species. It has a role as a plant metabolite, a human urinary metabolite, a NF-kappaB inhibitor and a xenobiotic. It is a bridged compound, a diterpene alkaloid, an organic heteropolycyclic compound, a polyether, a tertiary amino compound, a pentol, a secondary alcohol and a tertiary alcohol. It derives from a hydride of an aconitane. | [IC 50]
NF-κB | [References]
[1] KENTARO WADA Youkichi O Makoto Nihira. Effects of chronic administrations of aconitine on body weight and rectal temperature in mice[J]. Journal of ethnopharmacology, 2006, 105 1: Pages 89-94. DOI: 10.1016/j.jep.2005.10.007
[2] XIANG-ZHOU ZENG. Aconine inhibits RANKL-induced osteoclast differentiation in RAW264.7 cells by suppressing NF-κB and NFATc1 activation and DC-STAMP expression[J]. Acta Pharmacologica Sinica, 2015, 37 2: 255-263. DOI: 10.1038/aps.2015.85
[3] TENG-FEI LI Y W Nian Gong. Ester Hydrolysis Differentially Reduces Aconitine-Induced Anti-hypersensitivity and Acute Neurotoxicity: Involvement of Spinal Microglial Dynorphin Expression and Implications for Aconitum Processing[J]. Frontiers in Pharmacology, 2016, 7 1. DOI: 10.3389/fphar.2016.00367 |
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