| Identification | Back Directory | [Name]
kukoamine A | [CAS]
75288-96-9 | [Synonyms]
kukoamine A
1,14-Bis(dihydrocaffeoyl)spermidine
N1,N12-Bis(dihydrocaffeoyl) spermine
N,N'-[1,4-Butanediylbis(imino-3,1-propanediyl)]bis[3,4-dihydroxybenzenepropanamide]
N,N'-[Tetramethylenebis(iminotrimethylene)]bis[3-(3,4-dihydroxyphenyl)propionamide]
Benzenepropanamide,N,N'-[1,4-butanediylbis(imino-3,1-propanediyl)]bis[3,4-dihydroxy-
N,N'-((butane-1,4-diylbis(azanediyl))bis(propane-3,1-diyl))bis(3-(3,4-dihydroxyphenyl)propanamide) | [Molecular Formula]
C28H42N4O6 | [MDL Number]
MFCD29904538 | [MOL File]
75288-96-9.mol | [Molecular Weight]
530.66 |
| Chemical Properties | Back Directory | [Occurrence]
The root bark of Lychium chinense yields this alkaloid. Kukoamine A
possesses hypotensive activity inducing hypotension in rats at a dose of 5 mg/kg when
given intravenously. | [Boiling point ]
872.1±65.0 °C(Predicted) | [density ]
1.213±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 10 mg/ml | [form ]
A crystalline solid | [pka]
9.48±0.10(Predicted) | [color ]
Off-white to yellow | [InChIKey]
IOLDDENZPBFBHV-UHFFFAOYSA-N | [SMILES]
C(NCCCNC(=O)CCC1=CC=C(O)C(O)=C1)CCCNCCCNC(=O)CCC1=CC=C(O)C(O)=C1 | [CAS DataBase Reference]
75288-96-9 |
| Hazard Information | Back Directory | [Description]
Kukoamine A is a spermine alkaloid originally isolated from L. chinense that has diverse biological activities, including anticancer, neuroprotective, and anti-inflammatory properties.1 Kukoamine A (5-20 μg/ml) inhibits colony formation of U251 and WJ1 glioblastoma cells in a concentration-dependent manner.2 It halts the cell cycle at the G0/G1 phase and induces apoptosis when used at concentrations of 60 and 80 μg/ml. Kukoamine A (20 and 40 μM) induces autophagy and increases cell viability in an SH-SY5Y cell model of MPP-induced injury.3 It increases the number of dopamine neurons in the substantia nigra and striatum, decreases α-synuclein expression, and improves motor function in an MPTP mouse model of Parkinson’s disease when administered at a dose of 20 mg/kg per day. Kukoamine A (10 and 20 mg/kg) decreases IL-1β, TNF-α, and COX-2 protein levels in the hippocampus and increases hippocampal neurogenesis in a rat model of radiation injury.4 It also selectively inhibits trypanothione reductase (Ki = 1.8 μM), an enzyme that protects certain parasites from oxidative stress, over human glutathione reductase (Ki = >10 mM).5 | [Chemical Properties]
White crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from the bark of Lycium bark. | [Uses]
Kukoamine A is a neuroprotective agent which is used to prevent the loss of dopaminergic neurons in substantia nigra. | [Definition]
ChEBI: Kukoamine A is an amine. | [Synthesis]
(1) take the ground bone skin crushed 20-80 mesh, placed in the CO2 supercritical extraction tank extraction, through the liquid CO2, flow rate of 1-4 ml/min/g raw materials, while through the methanol to do the entrainment agent, flow rate of 1-4 ml/min/ | [IC 50]
Trypanosoma | [storage]
Store at -20°C | [References]
[1] SHINJI FUNAYAMA. Structure of kukoamine A, a hypotensive principle of Lycium chinense root barks1[J]. Tetrahedron Letters, 1980, 21 14: Pages 1355-1356. DOI: 10.1016/s0040-4039(00)74574-6
[2] QIAOPING WANG. Kukoamine A inhibits human glioblastoma cell growth and migration through apoptosis induction and epithelial-mesenchymal transition attenuation[J]. Scientific Reports, 2016, 6 1. DOI: 10.1038/srep36543
[3] XIAOLONG HU . Neuroprotective effects of Kukoamine A on neurotoxin-induced Parkinson’s model through apoptosis inhibition and autophagy enhancement[J]. Neuropharmacology, 2017, 117: Pages 352-363. DOI: 10.1016/j.neuropharm.2017.02.022
[4] YAQIONG ZHANG. Kukoamine A Prevents Radiation-Induced Neuroinflammation and Preserves Hippocampal Neurogenesis in Rats by Inhibiting Activation of NF-κB and AP-1[J]. Neurotoxicity Research, 2016, 31 1: 259-268. DOI: 10.1007/s12640-016-9679-4
[5] J A PONASIK. Kukoamine A and other hydrophobic acylpolyamines: potent and selective inhibitors of Crithidia fasciculata trypanothione reductase.[J]. Biochemical Journal, 1995, 311 ( Pt 2): 371-375. DOI: 10.1042/bj3110371 |
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