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Karakoline

CAS# 39089-30-0

Karakoline

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Quality Control of Karakoline

Number of papers citing our products

Chemical structure

Karakoline

3D structure

Chemical Properties of Karakoline

Cas No. 39089-30-0 SDF Download SDF
PubChem ID 441742 Appearance Powder
Formula C22H35NO4 M.Wt 377.5
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CCN1CC2(CCC(C34C2CC(C31)C5(CC(C6CC4C5C6O)OC)O)O)C
Standard InChIKey HKQZUYOVMYOFIT-VHNBHZRZSA-N
Standard InChI InChI=1S/C22H35NO4/c1-4-23-10-20(2)6-5-16(24)22-12-7-11-14(27-3)9-21(26,17(12)18(11)25)13(19(22)23)8-15(20)22/h11-19,24-26H,4-10H2,1-3H3/t11-,12-,13+,14+,15-,16+,17-,18+,19?,20+,21+,22-/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 Karakoline

The roots of Aconitum kusnezoffii Reichb.

Biological Activity of Karakoline

In vitro

Feeding deterrents from Aconitum episcopale roots against the red flour beetle, Tribolium castaneum.[Pubmed: 21417277]

J Agric Food Chem. 2011 Apr 27;59(8):3701-6.

The screening for insecticidal principles from several Chinese medicinal herbs showed that the ethanol extract of Aconitum episcopale roots possessed significant feeding deterrence against the red flour beetle, Tribolium castaneum.
METHODS AND RESULTS:
From the ethanol extract, six feeding deterrents were isolated by bioassay-guided fractionation. The compounds were identified as chasmanine, crassicauline A, Karacoline, sachaconitine, talatisamine, and yunaconitine from their spectroscopic data. Chasmanine, talatisamine, Karacoline, and sachaconitine exhibited feeding deterrent activity against T. castaneum adults, with EC(50) values of 297.0, 342.8, 395.3, and 427.8 ppm, respectively. Yunaconitine and crassicauline A also possessed feeding deterrent activity against T. castaneum adults, with EC(50) values of 653.4 and 1134.5 ppm, respectively.

Protocol of Karakoline

Structure Identification
J Med Chem. 1996 Nov 22;39(24):4860-6.

Nudicauline and elatine as potent norditerpenoid ligands at rat neuronal alpha-bungarotoxin binding sites: importance of the 2-(methylsuccinimido)benzoyl moiety for neuronal nicotinic acetylcholine receptor binding.[Pubmed: 8941400 ]

Methyllycaconitine (MLA, 1) is a novel, potent probe for mammalian and insect nicotinic acetylcholine receptors (nAChR) and displays remarkable selectivity toward neuronal [125I]-alpha-bungarotoxin (alpha BgTX) binding sites that correspond to alpha 7-type nAChR in mammalian brain.
METHODS AND RESULTS:
We have shown that, among a number of selected norditerpenoid alkaloids, elatine (2) and nudicauline (3) are equipotent with, or better than, MLA (1) in binding to brain [125I]-alpha BgTX binding sites, with IC50 values of 6.1, 1.7, and 7.6 nM, respectively. The 2-((S)-methylsuccinimido)benzoyl moiety of these ligands is crucial for high-affinity binding, whereas structural modifications to the norditerpenoid core of the ligand can be tolerated without loss of activity or selectivity. In addition to MLA (1), elatine (2), and nudicauline (3), we have examined lycoctonine (4), inuline (6), lappaconitine (7), N-desacetyllappaconitine (8), delsoline (10), delcorine (11), deltaline (12), condelphine (13), and Karacoline (14).
CONCLUSIONS:
This study therefore extends the range of norditerpenoids, other than MLA, which can be used to probe this important class of nAChR. All 12 alkaloids were assessed for activity at [3H]nicotine binding sites which are considered to represent alpha 4 beta 2 nAChR. Furthermore, the 1H and 13C NMR spectroscopic data of MLA and elatine have been critically compared.

Karakoline Dilution Calculator

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Preparing Stock Solutions of Karakoline

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.649 mL 13.245 mL 26.4901 mL 52.9801 mL 66.2252 mL
5 mM 0.5298 mL 2.649 mL 5.298 mL 10.596 mL 13.245 mL
10 mM 0.2649 mL 1.3245 mL 2.649 mL 5.298 mL 6.6225 mL
50 mM 0.053 mL 0.2649 mL 0.5298 mL 1.0596 mL 1.3245 mL
100 mM 0.0265 mL 0.1325 mL 0.2649 mL 0.5298 mL 0.6623 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 Karakoline

[ALKALOIDS OF UNDERGROUND PARTS OF GEORGIAN FLORA'S ACONITUM ORIENTALE MILL. AND ACONITUM NASUTUM FISCH. EX REICHEMB AND THEIR BIOLOGICAL ACTIVITY].[Pubmed:29461247]

Georgian Med News. 2018 Jan;(274):164-167.

The aim of research was to study underground parts of Aconitum orientale Mill and Aconitum nasutum Fisch exReichemb for the composition of biological active diterpenic alkaloids. The research object was underground parts of Aconitum species. Alkaloids sum was received from raw-material which was alkalined beforehand with chloroform extraction. From the results of research we established, that both species of Georgian flora's Aconitum contains alkaloids: lappaconitine, aconitine, Karakoline. Underground parts of Aconitum orientale and Aconitum nasutum differ from eath other with composition of alkaloids spectrum. Underground parts of Aconitum orientale contains bases: ranaconitine, gigactonine, licoctonine, but underground parts of Aconitum nasutum contains: talitizamine, kamakonine, aconosine. Alkaloids' summary substances, which were received from underground parts of Aconitum species spread in Georgia, showed selective cytotoxic activity towards A-549 (lung carcinoma), DLD-1 (intestine adenocarcinoma), WS-1 (human normal fibroblasts).

[Chemical constituents of lateral roots of Aconitum carmichaelii Debx].[Pubmed:25322557]

Yao Xue Xue Bao. 2014 Aug;49(8):1150-4.

In order to find the cardiotonic constituents of lateral roots of Aconitum carmichaelii Debx., the investigation was carried out. Silica gel column chromatography, Sephadex LH-20, medium-pressure MCI and reverse phase ODS column chromatography were used to separate the 90% EtOH extract of the lateral roots of Aconitum carmichaelii Debx. The structures of the isolated compounds have been identified by chemical properties and spectroscopic analyses. Ten compounds were isolated and their structures were elucidated as benzoic acid-5-hydroxy-2-benzoyl-amino methyl ester (1), honokiol (2), pinoresinol (3), salicylic acid (4), p-hydroxy-cinnamic acid (5), songorine (6), Karakoline (7), mesaconitine (8), hypaconitine (9) and 14-benzoylhypaconitine (10), separetely. Compound 1 is a new compound and its structure has been established by NMR, HR-ESI-MS, UV, IR and X-Ray. Compound 2-5 are isolated from the lateral roots of Aconitum carmichaelii Debx. for the first time.

Identification of diterpene alkaloids from Aconitum napellus subsp. firmum and GIRK channel activities of some Aconitum alkaloids.[Pubmed:23876370]

Fitoterapia. 2013 Oct;90:85-93.

Diterpene alkaloids neoline (1), napelline (2), isotalatizidine (3), Karakoline (4), senbusine A (5), senbusine C (6), aconitine (7) and taurenine (8) were identified from Aconitum napellus L. subsp. firmum, four (2-4, 6) of which are reported for the first time from this plant. The structures were determined by means of LC-MS, 1D and 2D NMR spectroscopy, including (1)H-(1)H COSY, NOESY, HSQC and HMBC experiments. Electrophysiological effects of the isolated compounds, together with nine diterpene alkaloids previously obtained from Aconitum toxicum and Consolida orientalis were investigated on stable transfected HEK-hERG (Kv11.1) and HEK-GIRK1/4 (Kir3.1 and Kir3.4) cell lines using automated patch clamp equipment. Significant blocking activity on GIRK channel was exerted by aconitine (7) (45% at 10 muM), but no blocking activities of the other investigated compounds were detected. The tested compounds were inactive on hERG channel in the tested concentration. The comparison of the previously reported metabolites of A. napellus subsp. firmum and compounds identified in our experiment reveals substantial variability of the alkaloid profile of this taxon.

Norditerpene and diterpene alkaloids from Aconitum variegatum.[Pubmed:15797610]

Phytochemistry. 2005 Apr;66(7):837-46.

Aerial parts of Aconitum variegatum L. from the Pyrenees furnished four norditerpene alkaloids, 16 beta-hydroxycardiopetaline, 8-ethoxysachaconitine, 14-acetylgenicunine B, N-deethyl-N-19-didehydrosachaconitine, five diterpene alkaloids 15-veratroyldictizine, 15-veratroyl-17-acetyldictizine, 15-veratroyl-17-acetyl-19-oxodictizine, N-ethyl-1 alpha-hydroxy-17-veratroyldictizine, variegatine and the known alkaloids sachaconitine, 14-O-acetylsachaconitine, Karakoline, talatizamine, 10-hydroxytalatizamine, 14-acetyltalatizamine, 14-acetyl-10-hydroxytalatizamine, N-methylarmepavine, pengshenin B, delsoline, dihydrodelsoline, delcosine and genicunin B. Structures of the alkaloids were established by MS, 1D- and 2D-NMR techniques.

Structural diversity and defensive properties of norditerpenoid alkaloids.[Pubmed:15503527]

J Chem Ecol. 2004 Jul;30(7):1393-408.

We have tested the insect antifeedant and toxic activity of 43 norditerpenoid alkaloids on Spodoptera littoralis and Leptinotarsa decemlineata including eserine (physostigmine), anabasine, and atropine. Antifeedant effects of the test compounds were structure- and species-dependent. The most active antifeedants to L. decemlineata were 1,14-diacetylcardiopetaline (9) and 18-hydroxy- 14-O-methylgadesine (33), followed by 8-O-methylconsolarine (12), 14-O-acetyldelectinine (27), Karakoline (7), cardiopetaline (8), 18-O-demethylpubescenine (13), 14-O-acetyldeltatsine (18), takaosamine (21), ajadine (24), and 8-O-methylcolumbianine (6) (EC50 < 1 microg/cm2). This insect showed a moderate response to atropine. S. littoralis had the strongest antifeedant response to 24, 18, 14-O-acetyldelcosine (19), and delphatine (29) (EC50 < 3 microg/cm2). None of the model substances affected the feeding behavior of this insect. The most toxic compound to L. decemlineata was aconitine (1), followed by cardiopetalidine (10) (% mortality > 60), 14-deacetylpubescenine (14), 18-O-benzoyl-18-O-demethyl-14-O-deacetylpubescenine (17), 14-O-acetyldelcosine (19), 14-deacetylajadine (25) and methyllycaconitine (30) (% mortality > 45). Orally injected S. littoralis larvae were negatively affected by 1, cardiopetaline (8), 10, 1,14-O-acetylcardiopetalidina (11), 12, 14, 1,18-O-diacetyl-19-oxo-gigactonine (41), olivimine (43), and eserine in varying degrees. Their antifeedant or insecticidal potencies did not parallel their reported nAChR binding activity, but did correlate with the agonist/antagonist insecticidal/antifeedant model proposed for nicotininc insecticides. A few compounds [14, tuguaconitine (38), 14-demethyldelboxine (40), 19, dehydrodelsoline (36), 18-O-demethylpubescenine (13), 41, 9, and delcosine (23)] had selective cytotoxic effects to ward insect-derived Sf9 cells. None were cytotoxic to mammalian CHO cells and none increased Trypanosoma cruzi mortality. The selective cytotoxic effects of some structures indicate that they can act on biological targets other than neuroreceptors.

Alkaloids from Delphinium pentagynum.[Pubmed:15279983]

Phytochemistry. 2004 Jul;65(14):2123-7.

Aerial parts of a collection of Delphinium pentagynum Lam. from Niebla, Southern Spain, furnished one diterpene alkaloid, 2-dehydrodeacetylheterophylloidine, two norditerpene alkaloids, 14-demethyl-14-isobutyrylanhweidelphinine and 14-demethyl-14-acetylanhweidelphinine, the known alkaloids 14-deacetylnudicauline, methyllycaconitine, 14-deacetyl-14-isobutyrylnudicauline, 14-acetylbrowniine, browniine, delcosine, lycoctonine, 18-methoxygadesine, neoline, Karakoline and the aporphine alkaloid magnoflorine. Structures of the alkaloids were established by MS, 1D and 2-D NMR techniques.

New norditerpenoid alkaloids from Aconitum falconeri.[Pubmed:11076560]

J Nat Prod. 2000 Oct;63(10):1393-5.

The roots of Aconitum falconeri have yielded two new norditerpenoid alkaloids, faleoconitine (1) and 3'-methoxyacoforestinine (2) along with the known compounds, Karakoline, 3-hydroxy-2-methyl-4H-pyran-4-one, and 3,4-dimethoxymethylbenzoate, which have been isolated for the first time from this plant. The previously reported pseudaconitine (3) was also isolated. Compounds 1 and 3 were found to be moderate inhibitors of the enzyme acetylcholinesterase.

Mode of antinociceptive and toxic action of alkaloids of Aconitum spec..[Pubmed:9459571]

Naunyn Schmiedebergs Arch Pharmacol. 1998 Jan;357(1):39-48.

Extracts of the plant Aconitum spec. are used in traditional Chinese medicine predominantly as anti-inflammatory and analgesic agents, the latter allegedly equally potent as morphine but without any habit-forming potential. As the only pharmacologically active compounds, the C19 diterpenoid alkaloid aconitine, and some of its derivatives, have been proven to be antinociceptive in different analgesic assays, but the mode of action is unknown. To elucidate the mode of action, ten aconitine-like derivatives were investigated with respect to their affinity for voltage-dependent Na+ channels, the action on synaptosomal Na+ and Ca2+ homoeostasis and their antinociceptive, arrhythmogenic and acute toxic properties. Since aconitine is known to bind to site II of Na+ channels, we determined the affinity of the aconitine-like derivatives in vitro to synaptosomal membranes by the [3H]-batrachotoxinin-binding assay and their properties on intrasynaptosomal concentrations of free Na+ and Ca2+ ([Na+]i and [Ca2+]i), both the latter determined fluorometrically with SBFI and Fura-2 respectively. Furthermore, the alkaloids' arrhythmogenic potential was investigated in guinea-pig isolated atria and the antinociceptive action on formalin-induced hyperalgesia and the acute toxic action estimated in mice. The results show that the alkaloids could be divided into at least three groups. The first is characterized by a high affinity to the site II of Na+ channels (Ki about 1.2 microM), the ability to enhance [Na+]i and [Ca2+]i (EC50 about 3 microM), a strong arrhythmogenic action that starts at about 30 nM, an antinociceptive effect (ED50 about 0.06 mg/kg) and high acute toxicity (LD50 values about 0.15 mg/kg). To this group belong aconitine, 3-acetylaconitine and hypaconitine. The second group, with lappaconitine as the only member, has an affinity to Na+ channels an order of magnitude lower (Ki = 11.5 microM), less acute toxicity (LD50 about 5 mg/kg), and a two orders of magnitude lower antinociceptive action (ED50 about 2.8 mg/kg) and lower cardiotoxicity (bradycardia observed at 3 microM). Additionally, lappaconitine suppresses the increase in [Ca2+]i of aconitine-stimulated synaptosomes and increases the excitation threshold of left atria, indicating an inhibition of Na+ channels. The other derivatives, i.e. delcorine, desoxydelcorine, Karakoline, lappaconidine, lappaconine and lycoctonine, belong to the third group, which has hardly any effects. They have a low affinity to Na+ channels with Ki values in the millimolar range, show no effect on synaptosomal [Na+]i and [Ca2+]i, no arrhythmogenic potential up to 100 microM, no antinociceptive activity and low toxicity with LD50 values greater than 50 mg/kg. For the investigated alkaloids we suggest two different antinociceptive-like modes of action. Aconitine, hypaconitine and 3-acetylaconitine may induce a block of neuronal conduction by a permanent cell depolarisation, whereas lappaconitine might act like local anaesthetics. However, because of the low LD50/ED30 quotients of 2-6, the antinociceptive-like action of the Aconitum alkaloids seems to reflect severe intoxication rather than a specific antinociceptive action. The structure/activity relationship shows that alkaloids that activate or block Na+ channels have a benzoyl ester side chain in the C-14 or C-4 positions respectively, whereas the other compounds lack this group.

Diterpenoid alkaloids from Delphinium davisii.[Pubmed:8699181]

J Nat Prod. 1996 Apr;59(4):360-6.

Three new hetisane-type diterpenoid alkaloids, davisinol (6), 18-benzoyldavisinol (7), and Davisin (9) have been isolated from Delphinium davisii Munz. and their structures established by detailed spectroscopic studies. Accurate 1H- and 13C-NMR assignments have been made for kobusine (8), a related hetisane-type alkaloid, and Karakoline (5), a norditerpenoid alkaloid. The known norditerpenoid alkaloids 14-acetylperegrine (4), 6-deacetylperegrine (3), and Karakoline (5) and the diterpenoid alkaloids hetisine and hetisinone were also isolated.

[Studies on the alkaloid constituents of Jiangyou fu-zi Aconitum carmichaeli from Sichuan].[Pubmed:1293938]

Yao Xue Xue Bao. 1992;27(9):670-3.

Six compounds were isolated from the aqueous extract of Aconitum carmichaeli Debx (cultivated in Jiang-you region of Sichuan province). Five of them have been identified as uracil (I), songorine HCl(II), Karakoline(III), neoline(IV), and fuzitine(VI). Compound V is a new C19-diterpenoid alkaloid determined as C33H47NO9 and named neojiangyouaconitine.

Description

Karacoline, a diterpene alkaloid found in the plant Aconitum kusnezoffii, reduces degradation of the extracellular matrix (ECM) in intervertebral disc degeneration (IDD) via the NF-κB signaling pathway.

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