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Yunaconitine

$336

  • Brand : BIOFRON

  • Catalogue Number : BD-D1214

  • Specification : 98%(HPLC)

  • CAS number : 70578-24-4

  • Formula : C35H49NO11

  • Molecular Weight : 659.76

  • PUBCHEM ID : 155569

  • Volume : 20MG

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Catalogue Number

BD-D1214

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

659.76

Appearance

White crystalline powder

Botanical Source

Aconitum carmichaeli Debx./Alkaloid from Aconitum delavayi, Aconitum vilmorrianum, Aconitum crassicaule, Aconitum forrestii, Aconitum hemsleyanum, Aconitum teipeicum, Aconitum pseudogeniculatum and Aconitum dolichorhynchum var. subglabratum (Ranunculaceae)

Structure Type

Tropanes

Category

Standards;Natural Pytochemical;API

SMILES

CCN1CC2(C(CC(C34C2C(C(C31)C5(CC(C6(CC4C5C6OC(=O)C7=CC=C(C=C7)OC)O)OC)OC(=O)C)OC)OC)O)COC

Synonyms

Benzoic acid, 4-methoxy-, (1α,3α,6α,14α,16β)-8-(acetyloxy)-20-ethyl-3,13-dihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-yl ester/yunnaconitine/(1α,3α,6α,14α,16β)-8-(acetyloxy)-20-ethyl-3,13-dihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-yl 4-methoxybenzoate/yunacotinine/Yunaconitine/(1α,3α,6α,14α,16β)-8-Acetoxy-20-ethyl-3,13-dihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-yl 4-methoxybenzoate

IUPAC Name

[8-acetyloxy-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] 4-methoxybenzoate

Applications

Yunaconitine(Guayewuanine B) is a highly toxic aconitum alkaloid.

Density

1.3±0.1 g/cm3

Solubility

Methanol; Chloroform

Flash Point

390.9±32.9 °C

Boiling Point

722.8±60.0 °C at 760 mmHg

Melting Point

142-144ºC

InChl

InChI=1S/C35H49NO11/c1-8-36-16-32(17-41-3)22(38)13-23(43-5)35-21-14-33(40)24(44-6)15-34(47-18(2)37,26(29(35)36)27(45-7)28(32)35)25(21)30(33)46-31(39)19-9-11-20(42-4)12-10-19/h9-12,21-30,38,40H,8,13-17H2,1-7H3

InChl Key

LLEMSCWAKNQHHA-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:70578-24-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

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

26767293

Abstract

OBJECTIVE:
To investigate the chemical constituents of the processed products of Aconitum Vilmorinian Radix.

METHODS:
The constituents were isolated by repeated column chromatography over silica gel, alumina and RP-C18 as well as recrystallization. The structures were elucidated on the basis of spectral analysis and physicochemical properties.

RESULTS:
Ten compounds were obtained from the methanol extract, and they were identified as yunaconitine (1), 8-deacetyl-yunaconitine (2), geniculatine C (3), vilmorrianine B (4), vilmorrianine C(5), vilmorrianine D (6), talatisamine (7), β-sitosterol (8), β-daucosterol (9) and β-sitosterol acetate (10).

CONCLUSION:
All compounds are obtained from the processed products of Aconitum Vilmoriniani Radix for the first time.

Title

[Chemical Constituents from Processed Products of Aconitum Vilmoriniani Radix].

Author

Guo ZJ, Yang ZY, Tan WH, Zhou ZH, Ma XX.

Publish date

2015 May

PMID

26481590

Abstract

Aconitum alkaloid poisoning can occur after drinking decoction and soup made from non-toxic herbs contaminated by aconite roots. In the present review, the main objective is to describe the clinical features, investigations and possible sources of contamination. A combination of neurological, gastrointestinal and cardiovascular signs and symptoms was seen. Ventricular tachyarrhythmias could occur in 18% of subjects. Yunaconitine and crassicauline A, mainly found in certain aconite roots from Southwest China, are most commonly involved. Herbal residues and unused herbs should first be inspected for gross contamination. On-site inspection at the retailer should exclude accidental mix-up or cross-contamination when handling aconite roots. Samples of prescribed herbs are examined for gross contamination and analysed for the presence of Aconitum alkaloids. Samples of the implicated herb are also collected from the wholesaler for investigation. If post-import contamination is unlikely, the regulatory authorities of the exporting countries should be notified for follow-up actions. It is a challenging task to work out how non-toxic herbs become contaminated by aconite roots. The source control with good agricultural and collection practices and quality assurance must be enhanced.

Copyright © 2015 John Wiley & Sons, Ltd.

KEYWORDS

Aconitum alkaloids; aconite poisoning; aconite roots

Title

Aconitum Alkaloid Poisoning Because of Contamination of Herbs by Aconite Roots.

Author

Chan TY1,2.

Publish date

2016 Jan 15