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Crassicauline A

CAS# 79592-91-9

Crassicauline A

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Quality Control of Crassicauline A

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Chemical structure

Crassicauline A

3D structure

Chemical Properties of Crassicauline A

Cas No. 79592-91-9 SDF Download SDF
PubChem ID 157539 Appearance Cryst.
Formula C35H49NO10 M.Wt 643.77
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CCN1CC2(CCC(C34C2C(C(C31)C5(CC(C6(CC4C5C6OC(=O)C7=CC=C(C=C7)OC)O)OC)OC(=O)C)OC)OC)COC
Standard InChIKey GAZDXIGXYWVWQX-UHFFFAOYSA-N
Standard InChI InChI=1S/C35H49NO10/c1-8-36-17-32(18-40-3)14-13-23(42-5)35-22-15-33(39)24(43-6)16-34(46-19(2)37,26(29(35)36)27(44-7)28(32)35)25(22)30(33)45-31(38)20-9-11-21(41-4)12-10-20/h9-12,22-30,39H,8,13-18H2,1-7H3
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 Crassicauline A

The roots of Aconitum transsectum Diels

Biological Activity of Crassicauline A

DescriptionCrassicauline A, a diterpenoid alkaloid in Aconitum herbs, is an analgesic drug clinically used in China. Crassicauline A possesses feeding deterrent activity against T. castaneum adults, with the EC(50) value of 1134.5 ppm.
In vitro

Measurement of yunaconitine and crassicauline A in small-volume blood serum samples by LC-MS/MS: tracing of aconite poisoning in clinical diagnosis.[Pubmed: 22841113]

Talanta. 2012 Aug 15;97:491-8.

Aconite poisoning is one of the most serious types of herb-related medical emergencies. In Hong Kong, many if not most of these poisoning cases are due to confusion in herbal species; that is, the wrong herbs are used in prescriptions. Such human errors, while inevitable perhaps, can be serious, and sometimes fatal. The chemical components responsible for aconite poisoning are yunaconitine and Crassicauline A.
METHODS AND RESULTS:
In the present study, a rapid and sensitive method for the screening and quantification of yunaconitine and Crassicauline A in human serum, using LC-MS/MS, was developed and validated. Methyllycaconitine was chosen as the internal standard. The limit of detection (LOD) of yunaconitine and Crassicauline A were found to be 0.022 and 0.021 ng/mL, respectively. The limit of quantification (LOQ) was 0.1 ng/mL for both yunaconitine and Crassicauline A. The recovery of yunaconitine and Crassicauline A ranged from 78.6% to 84.9% and 78.3% to 87.2%, respectively. The matrix effect of yunaconitine and Crassicauline A ranged from 110.0% to 130.4% and 121.2 to 130.0%, respectively. Both yunaconitine and Crassicauline A were stable in serum for at least 3 months at -20 °C, and the extracts were stable for at least 7 days. For clinical applications, serum samples of two patients confirmed to have had aconite herbs poisoning in 2008 were quantified using the developed method.
CONCLUSIONS:
The result showed that this method can be utilized in clinical routine applications. This screening method expedites the diagnosis in cases of suspected aconite poisoning, thus enabling doctors to treat the condition more quickly and effectively.

In vivo

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.
CONCLUSIONS:
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 Crassicauline A

Structure Identification
Chem Pharm Bull (Tokyo). 2009 Aug;57(8):801-7.

Structure-analgesic activity relationship studies on the C(18)- and C(19)-diterpenoid alkaloids.[Pubmed: 19652403]

For evaluation of C(18)- and C(19)-diterpenoid alkaloids as analgesics, three C(19)-diterpenoid alkaloids were isolated from the roots of Aconitum hemsleyanum var. circinatum and A. transsecutum; and twenty-five semisynthetic C(18)- or C(19)-diterpenoid alkaloids were prepared from lappaconitine, Crassicauline A or yunaconitine.
METHODS AND RESULTS:
In a mice acetic acid-induced abdominal constriction assay, four Crassicauline A analogs and three yunaconitine analogs exhibited good analgesic activities with 77.8-94.1% inhibition range in 0.1-10 mg/kg subcutaneous (s.c.) dose range at the point of 20 min after drug administration. Among them, 8-O-deacetyl-8-O-ethylCrassicauline A (ED(50)=0.0972 mg/kg) and 8-O-ethylyunaconitine (ED(50)=0.0591 mg/kg) were the most potent analgesics relative to the reference drugs lappaconitine (ED(50)=3.50 mg/kg) and Crassicauline A (ED(50)=0.0480 mg/kg).
CONCLUSIONS:
Analgesic activity data of these C(18)- and C(19)-diterpenoid alkaloids indicate that a tertiary amine in ring A, an acetoxyl or an ethoxyl group at C-8, an aromatic ester at C-14, and the saturation state of the ring D are important structural features necessary to the analgesic activity of the C(19)-diterpenoid alkaloids.

Crassicauline A Dilution Calculator

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Crassicauline A Molarity Calculator

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Preparing Stock Solutions of Crassicauline A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.5533 mL 7.7667 mL 15.5335 mL 31.067 mL 38.8337 mL
5 mM 0.3107 mL 1.5533 mL 3.1067 mL 6.2134 mL 7.7667 mL
10 mM 0.1553 mL 0.7767 mL 1.5533 mL 3.1067 mL 3.8834 mL
50 mM 0.0311 mL 0.1553 mL 0.3107 mL 0.6213 mL 0.7767 mL
100 mM 0.0155 mL 0.0777 mL 0.1553 mL 0.3107 mL 0.3883 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 Crassicauline A

Measurement of yunaconitine and crassicauline A in small-volume blood serum samples by LC-MS/MS: tracing of aconite poisoning in clinical diagnosis.[Pubmed:22841113]

Talanta. 2012 Aug 15;97:491-8.

Aconite poisoning is one of the most serious types of herb-related medical emergencies. In Hong Kong, many if not most of these poisoning cases are due to confusion in herbal species; that is, the wrong herbs are used in prescriptions. Such human errors, while inevitable perhaps, can be serious, and sometimes fatal. The chemical components responsible for aconite poisoning are yunaconitine and Crassicauline A. In the present study, a rapid and sensitive method for the screening and quantification of yunaconitine and Crassicauline A in human serum, using LC-MS/MS, was developed and validated. Methyllycaconitine was chosen as the internal standard. The limit of detection (LOD) of yunaconitine and Crassicauline A were found to be 0.022 and 0.021 ng/mL, respectively. The limit of quantification (LOQ) was 0.1 ng/mL for both yunaconitine and Crassicauline A. The recovery of yunaconitine and Crassicauline A ranged from 78.6% to 84.9% and 78.3% to 87.2%, respectively. The matrix effect of yunaconitine and Crassicauline A ranged from 110.0% to 130.4% and 121.2 to 130.0%, respectively. Both yunaconitine and Crassicauline A were stable in serum for at least 3 months at -20 degrees C, and the extracts were stable for at least 7 days. For clinical applications, serum samples of two patients confirmed to have had aconite herbs poisoning in 2008 were quantified using the developed method. The result showed that this method can be utilized in clinical routine applications. This screening method expedites the diagnosis in cases of suspected aconite poisoning, thus enabling doctors to treat the condition more quickly and effectively.

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 . 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.

Structure-analgesic activity relationship studies on the C(18)- and C(19)-diterpenoid alkaloids.[Pubmed:19652403]

Chem Pharm Bull (Tokyo). 2009 Aug;57(8):801-7.

For evaluation of C(18)- and C(19)-diterpenoid alkaloids as analgesics, three C(19)-diterpenoid alkaloids were isolated from the roots of Aconitum hemsleyanum var. circinatum and A. transsecutum; and twenty-five semisynthetic C(18)- or C(19)-diterpenoid alkaloids were prepared from lappaconitine, Crassicauline A or yunaconitine. In a mice acetic acid-induced abdominal constriction assay, four Crassicauline A analogs and three yunaconitine analogs exhibited good analgesic activities with 77.8-94.1% inhibition range in 0.1-10 mg/kg subcutaneous (s.c.) dose range at the point of 20 min after drug administration. Among them, 8-O-deacetyl-8-O-ethylCrassicauline A (ED(50)=0.0972 mg/kg) and 8-O-ethylyunaconitine (ED(50)=0.0591 mg/kg) were the most potent analgesics relative to the reference drugs lappaconitine (ED(50)=3.50 mg/kg) and Crassicauline A (ED(50)=0.0480 mg/kg). Analgesic activity data of these C(18)- and C(19)-diterpenoid alkaloids indicate that a tertiary amine in ring A, an acetoxyl or an ethoxyl group at C-8, an aromatic ester at C-14, and the saturation state of the ring D are important structural features necessary to the analgesic activity of the C(19)-diterpenoid alkaloids.

Description

Crassicauline A (Crassicaulin A) is a bioactive alkaloid found in roots of Aconitum carmichaeli. Crassicauline A (Crassicaulin A) possesses feeding deterrent activity against T. castaneum adults with an EC50 of 1134.5 ppm.

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