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PubMedDate not supplied

Quantification of Aconitum alkaloids in aconite roots by a modified RP-HPLC method.

The three Aconitum alkaloids, aconitine (1), mesaconitine (2) and hypaconitine (3), are pharmacologically active but also highly toxic. A standardised method is needed for assessing the levels of these alkaloids in aconite roots in order to ensure the safe use of these plant materials as medicinal herbs. By optimising extraction, separation and measurement conditions, a reliable, reproducible and accurate method for the quantitative determination of all three Aconitum alkaloids in unprocessed and processed aconite roots has been developed. This method should be appropriate for use in the quality control of Aconitum products. The three Aconitum alkaloids were separated by a modified HPLC method employing a C18 column gradient eluted with acetonitrile and ammonium bicarbonate buffer. Quantification of Aconitum alkaloids, detected at 240 nm, in different batches of samples showed that the content of 1, 2 and 3 varied significantly. In general, the alkaloid content of unprocessed roots was higher than that of processed roots. These variations were considered to be the result of differences in species, processing methods and places of origin of the samples.

Aconitine↗

PubMed2005

Separation and identification of Aconitum alkaloids and their metabolites in human urine.

To study the safety of Aconitum medicinal herbs in clinic and identify Aconitum alkaloids poisoning in forensic medicine, Aconitum alkaloids and their metabolites were separated and identified in human urine by liquid chromatography-electrospray ionization-multi-stage mass spectrometry (LC-ESI-MS(n)) and chemical pathway of metabolism was investigated. The alkaloids and their metabolites in the urine sample were extracted with solid-phase cartridges and separated by HPLC with acetonitrile-water-formic acid (40:60:0.5) mobile phase. Structures of five metabolites and three parent Aconitum alkaloids were identified with multi-stage mass spectrometry data through comparison with authentic substances as aconitine (M(1)), mesaconitine (M(2)), hypaconitine (M(3)), benzoylaconine (M(4)), benzoylmesaconine (M(5)), benzoylhypaconine (M(6)), 16-O-demethylaconitine (M(7)) and 16-O-demethylhypaconitine (M(8)), respectively. Among them, M(8) was identified and reported for the first time. Metabolic pathways of Aconitum alkaloids in human body were proposed.

Aconitum↗

PubMed2006

Sensitive analysis of aconitine, hypaconitine, mesaconitine and jesaconitine in human body fluids and Aconitum tubers by LC/ESI-TOF-MS.

The Aconitum species (Ranunculaceae) are widely distributed in northern Asia and North America. Their roots are popularly used in herbal medicines in China and Japan. Many cases of accidental, suicidal and homicidal intoxication with this plant have been reported; some of these were fatal because the toxicity of Aconitum is very high. It is thus important to detect and quantify Aconitum alkaloids in body fluids, with high sensitivity. We have developed a simple and sensitive method for measuring four kinds of Aconitum alkaloids (aconitine, hypaconitine, jesaconitine and mesaconitine) by LC/electrospray (ESI)-time-of-flight (TOF)-MS. For all of them, only molecular ions were observed at an orifice voltage of 75 V; at 135 V, base peaks corresponding to [M - 60 + H]+ ions were observed. These four compounds and methyllycaconitine (internal standard) in human plasma samples were purified by solid-phase extraction. The four extracted compounds were completely separated in mass chromatograms; the calibration curves showed good linearity in the range 10-300 ng/ml, and the detection limits were estimated to be 0.2-0.5 ng/ml. Using our method, we also determined the amounts of these compounds in tuber samples. The present method is applicable in clinical and forensic toxicology.

Aconitine↗

PubMedDate not supplied

Quantitative analysis of Aconitum alkaloids in the urine and serum of a male attempting suicide by oral intake of aconite extract.

A method for the quantitation of diesterditerpene-type Aconitum alkaloids and their hydrolysis products by gas chromatography-selected ion monitoring was applied to a clinical case study. A 45-year-old male attempted suicide by oral intake of Aconitum alkaloids, which are highly intoxicant extracts of Aconitum tubers. It was estimated that he had ingested approximately 11 mg of diesterditerpene-type alkaloids but was saved by intensive gastric irrigation. Mesaconitine, aconitine, hypaconitine, and their hydrolysis products were detected in the serum on the first day only. On the other hand, some alkaloids were still detectable in the urine even six days after intoxication. Aconitum alkaloids are biotransformed, and their hydrolysis products are excreted time-dependently to the urine. The urine was a useful material to identify the toxicants in the case of aconite intoxication.

Aconitum↗

PubMedDate not supplied

Distribution of Aconitum alkaloids in body fluids and tissues in a suicidal case of aconite ingestion.

A case involving a suicidal ingestion of Aconitum tubers is presented. A 40-year-old woman in Hokkaido, Japan ingested ground aconite and died of aconite intoxication about 4 h after ingestion. The Aconitum alkaloids were quantitated using gas chromatography-selected ion monitoring from extracts of the body fluids and organs. The blood and urine concentrations of jesaconitine, the main alkaloid of the aconite in this case, were 69.1 ng/mL and 237.8 ng/mL, respectively. Higher values of the alkaloid were demonstrated in the kidneys, the liver, and in the bile rather than other organs or serum, suggesting the alkaloids were eliminated by the liver and kidneys. In the gastrointestinal tract, the highest value of jesaconitine (471.3 ng/g) was in the ileal contents. These findings show that Aconitum alkaloids were found in the liver and kidneys in much higher concentrations than in serum and suggest that they were eliminated not only via urine but also in feces. Feces may be useful to detect Aconitum alkaloid if other biological samples are not available.

Aconitum↗

PubMed2006

[Percutaneous absorption of aconitine and mesaconitine in extracts of Radix Aconitum kusnezoffii].

OBJECTIVE: This study was conducted to evaluate the percutaneous absorption of aconitine and mesaconitine in extracts of Radix Aconitum kusnezoffii. METHODS: The extracts of Radix Aconitum kusnezoffii were collected by using Franz diffusion cells after permeation through the skin of rats. Then rate constants of skin permeation of aconitine and mesaconitine were determined by high-performance liquid chromatography (HPLC). RESULTS: Under the condition that the concentrations of azone and propylene glycol were both 4%, the cumulative doses of skin permeation (Q) of mesaconitine and aconitine in the extracts of Radix Aconitum kusnezoffii (600 mg/ml) for 24 hours were 165.819 and 487.747 microg/cm(2) respectively, and their rate constants of skin permeation were 18.391 and 78.805 microg.cm(-2).h(-1) respectively. CONCLUSION: The aconitine and mesaconitine in the extracts of Radix Aconitum kusnezoffii can penetrate well through the skin of rats. Propylene glycol and azone can promote this penetration effects. The formula of skin permeation of mesaconitine and aconitine is in accordance with Higuchi equation and there is a linear relationship between Q and t(1/2).

Aconitine↗

PubMedDate not supplied

Method for the determination of Aconitum alkaloids in dietary supplements and raw materials by reversed-phase liquid chromatography with ultraviolet detection and confirmation by tandem mass spectrometry: single-laboratory validation.

A study of single-laboratory validation (SLV) of a reversed-phase liquid chromatography (RP-LC) method was conducted for the determination of diester-diterpene Aconitum alkaloids, viz., aconitine, mesaconitine, and hypaconitine, in a variety of dietary supplements, including single- and multiple-ingredient dry powder extracts, pills, capsules, and raw materials. The Aconitum alkaloids in the samples were extracted by diethyl ether in the presence of ammonia. After cleanup with solid-phase extraction to remove the matrix interferences, the alkaloids were determined by RP-LC with UV detection at 235 nm, and the results were confirmed by tandem mass spectrometry. The linear responses for aconitine, mesaconitine, and hypaconitine based on the present LC system ranged from 0.5 to 200 microg/mL. Relative standard deviations of 2.0 to 6.9% were obtained from duplicate analysis of 6 test materials of different matrixes for the 3 Aconitum alkaloids performed by 2 analysts on 5 different days. The recoveries determined for supplements and raw materials spiked with 3 Aconitum alkaloids at levels of 2.5-10 microg/g were in the range of 86-99%. In view of the attainment of satisfactory results for accuracy, precision, and recovery in the SLV study, it is recommended that the method validation process proceed to a collaborative study.

Aconitum↗

PubMed1981

Arrow poisons in China. Part II. Aconitum--botany, chemistry, and pharmacology.

The botany of Chinese Aconitum species is briefly reviewed. Five species have been identified as sources of arrow poison: A. carmichaelii, A. nagarum, A. ouvrardianum, A. stylosum, and A. episcopale. The most important one, A. carmichaelii, has long served, together with A. kusnezoffii, as the main source of the Chinese medicinal aconite drugs--ts'ao wu (wu t'ou), the parent tuber, and fu tzu (ch 'uan wu), the daughter tuber. Two other aconite drugs have now been accepted into the Chinese materia medica: hsüeh shang i chih hao, from A. brachypodum, A. pendulum, and A. nagarum, and kuan pai fu, from A. coreanum. The folk-medicinal use of Aconitum species throughout China is also discussed. The alkaloid content and composition of Aconitum species known to occur in China are surveyed; and the effects of "processing", practised in order to diminish the toxicity of aconite drugs, are noted. Also the pharmacology of the aconites and their alkaloids is examined, in order to determine to what extent there may be a basis for the numerous medicinal properties attributed to the plants. Current understanding of the effectiveness of the drugs is incomplete and further study is required.

Aconitum↗

PubMed2005

Simultaneous determination of six Aconitum alkaloids in proprietary Chinese medicines by high-performance liquid chromatography.

By optimizing the extraction, separation and analytical conditions, a reliable and accurate high-performance liquid chromatography (HPLC) method coupled with photodiode array detector (DAD) was developed for simultaneous quantitative determination of six Aconitum alkaloids, i.e., aconitine, mesaconitine, hypaconitine, benzoylaconine, benzoylmesaconine and benzoylhypaconine, in Chinese medicinal herbs, aconite roots, and 12 proprietary Chinese medicines containing processed aconite roots. The separation of these Aconitum alkaloids was achieved on an ODS column with gradient elution using solvents of acetonitrile and ammonium bicarbonate buffer (pH 10.0+/-0.2). Intra-assay and inter-assay precision of the analytes were less than 2.97%, and the average recovery rates obtained were in the range of 90-103% for all with RSDs below 3.28%. Good linear relationships were showed with correlation coefficients for the analytes exceeded 0.999. Quantitative analysis of the six Aconitum alkaloids in the unprocessed and processed aconite roots and in twelve proprietary Chinese medicines containing processed aconite roots showed that the contents of the alkaloids varied significantly. This method and quantitation results can provide a scientific and technical platform to the products manufacturers for setting up a quality control standard as well as to the public for quality and safety assurance of the proprietary Chinese medicines and other herbal preparations containing aconite roots.

Aconitum↗

PubMed2005

Quantitative determination of diterpenoid alkaloids in four species of Aconitum by HPLC.

A high performance liquid chromatography (HPLC) method has been developed for the determination of five principal alkaloids (benzoylmesaconine, mesaconitine, aconitine, hypaconitine and deoxyaconitine) found in four species of genus Aconitum. The five alkaloids were analyzed simultaneously with an XTerraRP18 column by gradient elution using 0.03 M ammonium hydrogen carbonate-acetonitrile as mobile phase. The recovery of the method was 94.6-101.9%, and all the alkaloids showed good linearity (gamma = 0.9999) in a relatively wide concentration range. The results indicated that contents of alkaloids in Aconitum varied significantly from species to species; hence quality control of Aconitum drugs is very necessary.

Aconitine↗

PubMed2005

Severe acute poisoning with homemade Aconitum napellus capsules: toxicokinetic and clinical data.

Aconitum napellus is an extremely dangerous plant that contains various toxic diterpenoid alkaloids, mainly aconitine primarily concentrated in the roots. We report a case of acute intoxication of a 21-year-old man admitted to our Emergency Department after the ingestion, in order to sleep, of three homemade Aconitum napellus capsules. Capsules were measured to contain 237 mg of root and 19 microg of aconitine. The patient experienced the first symptoms on wakening 5 hours later with generalized paresthesia, nausea, diarrhea, vertigo, thoracic pain dyspnea, and dyschromatopsia. At admission, 7 hours after intake electrocardiographic analysis showed a sinusal bradycardia with polymorphic and bigeminal ventricular extrasystolia. Cardiovascular and neurological symptoms disappeared, respectively within 11 and 13 hours of ingestion. The patient was discharged from the ICU on day 2. Plasmatic concentrations at H7, H9, H14 H19, and after ingestion were, respectively, of 1.75, 0.75, 0.35, and 0.02 ng/mL. The calculated half-life of aconitine was 3 hours. To our knowledge, this is the first reported case with an aconitine toxicokinetic-effect relationship. The authors stress that clinicians must be aware of possible occurrence of acute poisoning with Aconitum napellus in European countries and in the United States as herbal medicine is becoming increasingly popular.

Aconitum↗

PubMed2004

The local anesthetic activity of Aconitum alkaloids can be explained by their structural properties: a QSAR analysis.

Alkaloids isolated from Aconitum roots exhibit anesthetic effects at peripheral nerves. We performed the present quantitative structure-activity relationship (QSAR) analysis in order to understand the mechanism of action as local anesthetics of 11 Aconitum alkaloids. The alkaloids with the highest anesthetic activity had an aroyl/aroyloxy group at R14 position while the weaker anesthetic alkaloids had the aroyloxy group at R4. The stable compounds exhibited a higher local anesthetic activity than the unstable compounds. In relation to the reactivity indexes of atoms on the aromatic ring, C2' was more reactive while C3' and C5' were less reactive in the compounds with the highest anesthetic activity. Reactivity of N, C1', C4' and C6' was similar between the two groups of alkaloids. The pKa was approximately 7.3 in both groups. The local anesthetic ED50 of alkaloids was significantly inversely related to molecular weight, core-core repulsion energy, steric energy and RI-C2', and directly related to electronic energy, total energy, RI-C5' and to the heat of formation. In conclusion, we identified a set of structural parameters that are related to the local anesthetic activity of Aconitum alkaloids. Our findings are useful to understand the mechanism of action of these alkaloids and to provide a rational for chemical manipulation of the compounds in order to obtain potent derivates with minor toxicity.

Acetic Acid↗

PubMed2002

[The method for determination of aconitum alkaloids in Radix Aconiti Kusnezoffii].

The methods for the determination of Aconitum alkaloids in Radix Aconiti Kusnezoffii were established. Volumetric analysis with the indicator of methyl red-bromcresol green and colorimetric analysis with acid dye of bromecresol green under the wavelength of 416 nm were used for the assay of total alkaloids. Colorimetric analysis of hydroxamic acid-Fe was for the assay of total ester-diterpene type Aconitum alkaloids. Three kinds of diester-diterpene type Aconitum alkaloids (aconitine, hypaconitine and mesaconitine) were determined by HPLC method. The HPLC system consisted of C18 as the stationary phase and acetonitrile: buffer (acetic acid-triethylamine, pH 6.25) = 71:29 as the mobile phase. The wavelength was 235 nm.

Aconitine↗

PubMed2006

[Isolation and identification of hetisine-type alkaloids from Aconitum coreanum by high speed countercurrent chromatography].

AIM: To search for more bioactive compounds from the roots of Aconitum coreanum (Lèvl.) Rapaics. METHODS: High speed countercurrent chromatography was successfully applied to the separation of alkaloids from Aconitum coreanum. The structures were elucidated by their physicochemical properties and spectroscopic analysis. RESULTS: Two-phase solvent system composed of CHCl3-CH3OH-0.2 mol x L(-1) HCl (10:3:3, volume ratio) was used in this experiment, eight alkaloids were obtained from the roots of Aconitum coreanum, which were identified as: 2alpha-propionyl-11alpha,13beta-diacetyl-14-hydroxyhetisine (I), Guanfu base P (II), Guanfu base G (III), Guanfu base F (IV), Guanfu base Z (V), Guanfu base O (VI), Guanfu base A (VII), Guanfu base B (VIII). CONCLUSION: Compound I is a new alkaloid, named Guanfu base R.

Aconitum↗

PubMed1995

[Experimental comparison of the analgesic action of Aconitum and its processed products].

This paper deals with the effects of crude Aconitum and Aconitum processed by a new method of moistening and steaming, and by method of pharmacopoeial stipulation on the analgesic action with writhing test and hot plate test in mice. The result shows that the Aconitum processed by new method No 1, which applies moistening in water for 48h and then heating with high pressure steam (68.65kPa, 115 degrees C) for 2h has an advantage over that processed according to pharmacopoeial routine (P < 0.05).

Aconitum↗

PubMed2003

A column-switching LC/MS/ESI method for detecting tetrodotoxin and Aconitum alkaloids in serum.

A liquid chromatography-mass spectrometry-electrospray ionization (LC/MS/ESI) method coupled with a column-switching technique has been developed for the determination of tetrodotoxin (TTX) and Aconitum alkaloids and their metabolites, such as aconitine, mesaconitine, hypaconitine, jesaconitine, benzoylaconine, benzoylmesaconine, benzoylhypaconine and 14-anisoylaconine, in serum. An on-column column-switching technique was employed to analyze TTX and Aconitum alkaloids and their metabolites without pretreatment of the serum. Combination of a multimode column with reversed phases and cation exchange for TTX, and use of a multimode column with reversed phases and a hydrophobic polymer column for Aconitum alkaloids and their metabolites provided successful separation and MS determination in ESI positive mode. A 100 microl serum sample was directly injected into a precolumn. For TTX monitored at m/z 320.1 in the selected ion monitoring mode, the calibration curve was linear within the range 0.1-100 ng/ml and the limit of detection was 0.1 ng/ml. For aconitine, mesaconitine, hypaconitine and jesaconitine, linear calibration curves were obtained up to 500 ng/ml and the limit of detection ranged from 0.2 to 1 ng/ml. For benzoylaconine, benzoylmesaconine, benzoylhypaconine and 14-anisoylaconine, linear calibration curves were obtained up to 500 ng/ml and the limit of detection ranged from 2 to 50 ng/ml. Recoveries from serum samples were within the range 78-119% for all the compounds studied.

Aconitine↗

PubMed2001

Molecular markers reveal little genetic differentiation among Aconitum noveboracense and A. columbianum (Ranunculaceae) populations.

Aconitum noveboracense, a rare, herbaceous perennial, is restricted to recently unglaciated areas in Iowa, Wisconsin, Ohio, and New York, and federally classified as a threatened species. These populations may be disjuncts of the common congener, A. columbianum Nutt., which occurs in the mountains of the western United States. Morphological characters do not reliably separate these taxa. The identity of Black Hills populations, located between the ranges of the rare and common species, is also uncertain. We characterized genetic variation within and among the Aconitum populations in question using isozymes and randomly amplified polymorphic DNA (RAPDs). Isozymes indicate a high degree of similarity among all populations and a high level of genetic diversity in Black Hills populations. Of 97 scorable RAPD loci, 89.7% are polymorphic and clearly resolve most populations. Like isozymes, RAPDs indicate high levels of genetic diversity in the Black Hills and very strong similarity of these populations to A. columbianum from the Bighorn Mountains. Aconitum noveboracense populations show >80% similarity to A. columbianum populations. A population of A. uncinatum from Ohio shows the greatest differentiation from other populations. Therefore, both isozyme and RAPD data concur with the recent treatment of A. noveboracense and A. columbianum as a single species.

Journal Article↗

PubMed2003

Characterization of aconitine-type alkaloids in the flowers of Aconitum kusnezoffii by electrospray ionization tandem mass spectrometry.

The fragmentation mechanism of aconitine-type alkaloids in the flowers of Aconitum kusnezoffii (FAK) was investigated using electrospray ionization tandem mass spectrometry (ESI-MS(n)) firstly. The analysis of the collision-induced dissociation (CID) spectra of three purified aconitine standards and six previously reported aconitines indicated that the fragmentation of the protonated aconitines at low-energy CID follows a similar pathway. The elimination of a C(8)-substituent such as an acetic acid or a fatty acid is the dominant fragmentation mode in MS2. Successive losses of CH(3)COOH, CH(3)OH, H(2)O, BzOH, and CO are the main fragmentation pathways of aconitine-type alkaloids in MS(3) spectra. Based on these features, a rapid method for the direct detection and characterization of alkaloids from an ethanolic extract of FAK is described. All the known aconitum alkaloids are detected and a series of lipo-aconitines has been found for the first time in this plant.

Aconitine↗