Isolation and structure elucidation of the alkaloids of Delphinium glaucescens Rybd

Pelletier, S. William; Dailey, Oliver D.; Mody, Naresh V.; Olsen, John D.

doi:10.1021/jo00329a028

Cited by 60 publications

(46 citation statements)

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“…The MLA used in this study was extracted from Delphinium barbeyi following previously published methods (Pelletier et al, 1981(Pelletier et al, , 1989Manners et al, 1991); MLA is identical in low larkspur. The purified alkaloids and alkaloid extracts were suspended in PBS solution.…”

Section: Alkaloid Preparationmentioning

confidence: 99%

The acute toxicity of the death camas (Zigadenus species) alkaloid zygacine in mice, including the effect of methyllycaconitine coadministration on zygacine toxicity1

Welch

Panter

Gardner

et al. 2011

Journal of Animal Science

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Death camas (Zigadenus spp.) is a common poisonous plant on foothill rangelands in western North America. The steroidal alkaloid zygacine is believed to be the primary toxic component in death camas. Poisonings on rangelands generally occur in the spring when death camas is abundant, whereas other more desirable forage species are limited in availability.In most cases where livestock are poisoned by plants in a range setting, there is more than one potential poisonous plant in that area. One common poisonous plant that is often found growing simultaneously in the same area as death camas is low larkspur (Delphinium nuttallianum). Consequently, the objectives of this study were to conduct acute toxicity studies in mice and to determine if coadministration of low larkspur will exacerbate the toxicity of death camas. We first characterized the acute toxicity of zygacine in mice. The LD 50 of zygacine administered intravenously (i.v.) and orally was 2.0 ± 0.2 and 132 ± 21 mg/kg, respectively. The rate of elimination of zygacine from whole blood was determined to be 0.06 ± 0.01/min, which corresponds to an elimination half-life of 13.0 ± 2.7 min. The i.v. LD 50 of total alkaloid extracts from a Utah and a Nevada collection were 2.8 ± 0.8 and 2.2 ± 0.3 mg/kg, respectively. The i.v. LD 50 of methyllycaconitine (MLA), a major toxic alkaloid in low larkspur, was 4.6 ± 0.5 mg/kg, whereas the i.v. LD 50 of a 1:1 mixture of MLA and zygacine was 2.9 ± 0.7 mg/kg. The clinical signs in mice treated with this mixture were very similar to those of mice treated with zygacine alone, including the time of onset and death. These results suggest that there is an additive effect of coadministering these 2 alkaloids i.v. in mice.The results from this study increase knowledge and understanding regarding the acute toxicity of death camas. As combined intoxications are most likely common, this information will be useful in further developing management recommendations for ranchers and in designing additional experiments to study the toxicity of death camas to livestock.

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Section: Alkaloid Preparationmentioning

confidence: 99%

The acute toxicity of the death camas (Zigadenus species) alkaloid zygacine in mice, including the effect of methyllycaconitine coadministration on zygacine toxicity1

Welch

Panter

Gardner

et al. 2011

Journal of Animal Science

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“…Earlier methods typically measured what was termed Total Alkaloid Concentration (TAC). This was measured initially by chemical titration methods [30,31], then gravimetrically [32][33][34], and then through calibrated Near Infrared Spectroscopy (NIRS) [35] and Infrared (IR) spectroscopy [36]. Methods for TAC are attractive in that they are typically less costly and can provide a relative rapid preliminary indicator of toxicity, especially if the individual alkaloid components of the larkspur being tested are previously known.…”

Section: Analytical Techniquesmentioning

confidence: 99%

Adverse Effects of Larkspur (Delphinium spp.) on Cattle

et al. 2015

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Abstract:There are numerous species of larkspur (Delphinium spp.) in North America. Larkspurs are a major cause of cattle losses on western ranges in the USA, especially on foothill and mountain rangelands. The toxicity of larkspur species is due to various norditerpenoid alkaloids. In this article, we review the current knowledge regarding larkspur ecology and distribution, analytical technologies to study and quantify the toxins in larkspur, the toxicology of the larkspur plants and their individual toxins, known genetic variations in larkspur susceptibility, and current management recommendations to mitigate losses from larkspur poisoning.

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“…The HR-ESI-MS of 2 exhibited a protonated molecular ion peak at m/z 500.2647 [MϩH] ϩ (Calcd 500.2643) corresponding to the pseudo-molecular formula of C 28 H 37 NO 7 . The 1 H-and 13 C-NMR spectra of 2 exhibited characteristic features of an atisine-type alkaloid.…”

mentioning

confidence: 99%

“…5 ) also confirmed the a-configuration of the 15-(2-methylbutyryl) ester group. In addition, the stereochemistry of this group may be assigned as "S" based on references, which reported some other natural products bearing the same moiety, [6][7][8][9] and the absolute configuration of C-2Ј was in agreement with the L-isoleucine pathway in the biosynthesis of the secondary metabolites. 10 Table 2).…”

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confidence: 99%

Three New Diterpenoid Alkaloids from Roots of Aconitum ouvrardianum HAND.-MAZZ.

Hou

Chen

Jian

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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The plant Aconitum ouvrardianum HAND.-MAZZ. grows in Diqing country of Yunnan province in China at an elevation of 3000 m. Biological activity studies performed on diterpenoid alkaloids of "CaoWu" species have shown analgesia, anti-imflammatory and antiarrhythmic action. 1,2) To our knowledge, no phytochemical study of this plant has previously been undertaken. These reasons and our interest in the species prompted us to work with the A. ouvrardianum. In the course of our studies on the alkaloids of this plant, a new C 19 -diterpenoid alkaloid, ouvrardiantine (1) and two new C 20 -diterpenoid alkaloids, ouvrardiandines A (2) and B (3) have been isolated from the root of A. ouvrardianum. This paper describes the separation and structural elucidation of these new alkaloids. Results and DiscussionOuvrardiantine (1) The configuration of 2-OH was a-orientation, based on the downfield shift of C-19 (d C 51.8 t) in the 13 C-NMR spectra of compound 1. In this case, there was a hydrogen bond formed between N atom and 2a-OH group (Fig. 2). 4) Finally, all the evidence given above led to assignment of the structure of ouvrardiantine as 1.Ouvrardiandine A (2) was isolated as a white amorphous powder, A new C 19 -diterpenoid alkaloid, ouvrardiantine (1) and two new C 20 -diterpenoid alkaloids, ouvrardiandines A (2) and B (3) were isolated from the root of Aconitum ouvrardianum HAND.-MAZZ. The structure of the new alkaloids was established on the basis of spectral data (1D-and 2D-NMR, HR-MS).

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Isolation and structure elucidation of the alkaloids of Delphinium glaucescens Rybd

Cited by 60 publications

References 1 publication

The acute toxicity of the death camas (Zigadenus species) alkaloid zygacine in mice, including the effect of methyllycaconitine coadministration on zygacine toxicity1

The acute toxicity of the death camas (Zigadenus species) alkaloid zygacine in mice, including the effect of methyllycaconitine coadministration on zygacine toxicity1

Adverse Effects of Larkspur (Delphinium spp.) on Cattle

Three New Diterpenoid Alkaloids from Roots of Aconitum ouvrardianum HAND.-MAZZ.

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