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Crassicauline A

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-C2016

  • Specification : 98%

  • CAS number : 79592-91-9

  • Formula : C35H49NO10

  • Molecular Weight : 643.76

  • PUBCHEM ID : 157539

  • Volume : 20mg

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Catalogue Number

BF-C2016

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

643.76

Appearance

White crystalline powder

Botanical Source

Aconitum carmichaelii,Aconitum bulleyanum,Aconitum sungpanense,Aconitum tatsienense

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

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

Synonyms

Aconitane-8,13,14-triol,20-ethyl-1,6,16-trimethoxy-4-(methoxymethyl)-,8-acetate 14-(4-methoxybenzoate),(1alpha,6alpha,14alpha,16beta)/8-Acetoxy-20-ethyl-13-hydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-yl 4-methoxybenzoate/Benzoic acid, 4-methoxy-, 8-(acetyloxy)-20-ethyl-13-hydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-yl ester/8-(acetyloxy)-20-ethyl-13-hydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-yl 4-methoxybenzoate/crassicauline-A

IUPAC Name

[8-acetyloxy-11-ethyl-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] 4-methoxybenzoate

Density

1.3±0.1 g/cm3

Solubility

Methanol; Ethanol; Acetone

Flash Point

370.0±31.5 °C

Boiling Point

688.2±55.0 °C at 760 mmHg

Melting Point

166-168ºC

InChl

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

InChl Key

GAZDXIGXYWVWQX-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:79592-91-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

32297141

Abstract

Both Aconitum hemsleyanum and Aconitum geniculatun have abundant contents of yunaconitine (1). Yunaconitine (1) has similar skeleton to crassicauline A (3); the only difference between them is that 1 contains a α-hydroxyl group at C-3. Our team attempts to convert 1 into 3 because 3 owns pharmacological activity. There are two steps to achieve the transformation above: firstly, use dehydration reaction to transform yunaconitine (1) into dehydroyunaconitine (2); secondly, use hydrogen reduction to acquire crassicauline A (3). Compared with other methods, this one below is more suitable for production application and more concise; moreover, the cost is lower with higher yield.

KEYWORDS

Crassicauline A; Diterpenoid alkaloids; Yunaconitine

Title

Partial Synthesis of Crassicauline A from Yunaconitine.

Author

Zhang RP1,2, Lin YJ2, Yu HF2, Chen SY3, Zhou J4.

Publish date

2020 Apr 15

PMID

28276004

Abstract

BACKGROUND AND OBJECTIVES:
Crassicauline A, a C19 diterpenoid alkaloid in Aconitum herbs, is an analgesic drug clinically used in China. The in vivo metabolism of crassicauline A is poorly understood, while potential bioactivation is anticipated via hydroxylation metabolism. This work, therefore, aimed to investigate the in vivo hydroxylation metabolism of crassicauline A in rats.

METHODS:
Using a de novo developed and validated UPLC-MS/MS method, excretion studies in rats were carried out to investigate the recoveries of crassicauline A and its hydroxylated metabolites in urine and feces. Mass fragmentation analysis was used to identify the detected hydroxylated metabolites. In vitro metabolism assay in liver S9 fraction was employed to preliminarily investigate the inter-species difference of hydroxylation metabolism between rats and human.

RESULTS:
At a toxic dose of 100 µg/kg, less than 10% and 5% of the administrated dose of crassicauline A were recovered in the urine and feces after single intravenous and oral administration, respectively. Trace of yunaconitine, a possible 3-hydroxylated metabolite of crassicauline A, was detected in urine samples, but not considered to be derived from the in vivo metabolism, because the recovered yunaconitine and crassicauline A was equivalent to their occurrences in the test article. Another hydroxylated metabolite was detected with much higher levels than yunaconitine. Based on chromatographic behaviors and fragmentation analysis, the hydroxylation site of this metabolite was tentatively identified at C-15 on the skeleton, which might have produced a toxic alkaloid known as deoxyjesaconitine. The in vivo observations were consistent with the preliminary in vitro results in liver S9 fraction, in which an inter-species difference was highlighted that rats demonstrated more hydroxylation than human did.

CONCLUSIONS:
This work disclosed that crassicauline A is elimilated in rats predominantly by metabolism under toxic dosage and the hydroxylation probably at C-15 might be a potential bioactivation pathway in both rats and human.

KEYWORDS

Intravenous Group; Lappaconitine; Quality Control Sample; Test Article; Unknown Metabolite

Title

Hydroxylation Metabolisms of Crassicauline A in Rats Under Toxic Dose.

Author

Fan X1,2, Yin SS1,3,2, Li XJ3, Yang K2, Xu L1, Lan K4,5,6.

Publish date

2017 Oct

PMID

22841113

Abstract

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 °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.

Copyright © 2012 Elsevier B.V. All rights reserved.

Title

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

Author

Ka-Wing Chung K1, Pak-Lam Chen S, Ng SW, Wing-Lai Mak T, Sze-Yin Leung K.

Publish date

2012 Aug 15


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[1][2].