Karakoline - CAS 39089-30-0

Karakoline - CAS 39089-30-0 Catalog number: BADC-00279

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Alkaloid , from plants of the Ranunculaceae family. Ganglioblocker; nicotinic receptor antagonist; hypotensive; presents micromolar affinity at brain a Bungarotoxin-sensitive nAChR. (See attached sheet.)

Category
ADCs Cytotoxin
Product Name
Karakoline
CAS
39089-30-0
Catalog Number
BADC-00279
Molecular Formula
C22H35O4N
Molecular Weight
377.52
Karakoline

Ordering Information

Catalog Number Size Price Quantity
BADC-00279 20mg $698
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Description
Alkaloid , from plants of the Ranunculaceae family. Ganglioblocker; nicotinic receptor antagonist; hypotensive; presents micromolar affinity at brain a Bungarotoxin-sensitive nAChR. (See attached sheet.)
Synonyms
(16S)-20-Ethyl-16-methoxy-4-methylaconitane-1α,8,14α-triol
IUPAC Name
(1S,2R,3R,4S,5S,6S,8S,9S,13R,16S,17R)-11-ethyl-6-methoxy-13-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8,16-triol
Canonical SMILES
CCN1CC2(CCC(C34C2CC(C31)C5(CC(C6CC4C5C6O)OC)O)O)C
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
InChIKey
HKQZUYOVMYOFIT-VHNBHZRZSA-N
Solubility
Chloroform, moderately in acetone, not well in water
Melting Point
185-186 °C
Application
ADCs Cytotoxin
Appearance
Solid Powder
Purity
97% (TLC)
Quantity
Milligrams-Grams
Quality Standard
Enterprise Standard
Shipping
Room temperature, or blue ice upon request.
Storage
Store at +4 °C, in dark place.
1.[Effects of steaming and baking on content of alkaloids in Aconite Lateralis Radix (Fuzi)].
Yang CL;Huang ZF;Zhang YH;Liu YH;Liu YH;Chen Y;Yi JH 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.
2.Feeding deterrents from Aconitum episcopale roots against the red flour beetle, Tribolium castaneum.
Liu ZL;Cao J;Zhang HM;Lin LL;Liu HJ;Du SS;Zhou L;Deng ZW J Agric Food Chem. 2011 Apr 27;59(8):3701-6. doi: 10.1021/jf104879h. Epub 2011 Mar 18.
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 . 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.
3.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.
Hardick DJ;Blagbrough IS;Cooper G;Potter BV;Critchley T;Wonnacott S J Med Chem. 1996 Nov 22;39(24):4860-6.
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. 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).

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This equation is commonly abbreviated as: C1V1 = C2V2

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