Determination of cross-contamination of the diastereomers ephedrine and pseudoephedrine by high-performance liquid chromatography, thin-layer chromatography and carbon-13 nuclear magnetic resonance spectroscopy

Barkan, Susan; Weber, John D.; Smith, Edward C.

doi:10.1016/s0021-9673(00)80576-2

Cited by 17 publications

(7 citation statements)

References 8 publications

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“…Adapted from Barkan et al (1981). HPLC was carried out on a Spectra-Physics Model 8000 HPLC equipped with an SP 8000 integrator and Spectra Physics Model 770 UV-visible detector set at 21Onm.…”

Section: Methodsmentioning

confidence: 99%

“…Analytical techniques such as HPLC, which accurately determine and quantify these compounds, are quite recent developments (Barkan et al 1981;Sagara et al 1983;Jian et al 1988;Liang et al 1990Liang et al , 1991. It is now feasible to survey the distribution of phenylalkylamines throughout the Ephedra genus and to construct chemical profiles within and between species.…”

Section: Distribution Of the Ephedrinesmentioning

confidence: 99%

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X Ephedra Species: In Vitro Culture, Micropropagation, and the Production of Ephedrine and Other Alkaloids

O'Dowd

McCauley

Wilson

et al. 1998

Biotechnology in Agriculture and Forestry

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Section: Methodsmentioning

confidence: 99%

Section: Distribution Of the Ephedrinesmentioning

confidence: 99%

X Ephedra Species: In Vitro Culture, Micropropagation, and the Production of Ephedrine and Other Alkaloids

O'Dowd

McCauley

Wilson

et al. 1998

Biotechnology in Agriculture and Forestry

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“…Ephedrine and pseudoephedrine levels in the aqueous eluent were determined by HPLC using a method based on that described by Barkan, Weber, and Smith (1981). Ephedrine and pseudoephedrine levels in the aqueous eluent were determined by HPLC using a method based on that described by Barkan, Weber, and Smith (1981).…”

Section: Isolation and Identification Of Ephedrine And Pseudoephedrinmentioning

confidence: 99%

“…substances including 6-hydroxykynurenic acid were removed by application of aliquots of plant extracts (generally prepared by steeping 0.5 g fresh tissue in 2.5 mL ethanol) to Accell Plus QMA Sep-Pak cartridges (Waters) after dilution with an equal volume of water. Ephedrine and pseudoephedrine levels in the aqueous eluent were determined by HPLC using a method based on that described by Barkan, Weber, and Smith (1981). Samples were chromatographed on a Bondapak C 18 column (3.9 ϫ 300 mm) using 1% acetonitrile in 0.05 mol/L monobasic sodium phosphate at 1 mL/min.…”

Section: Isolation and Identification Of Ephedrine And Pseudoephedrinmentioning

confidence: 99%

New observations on the secondary chemistry of world Ephedra (Ephedraceae)

Caveney

Charlet

Freitag

et al. 2001

American J of Botany

118

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For several millennia, stem extracts of Ephedra (Ephedraceae, Gnetales) have been used as folk medicines in both the Old and New World. Some species were used in treatments of questionable efficacy for venereal disease in North America during the last century. Many Eurasian species produce phenylethylamine alkaloids, mostly ephedrine and pseudoephedrine, that interact with adrenergic receptors in the mammalian sympathetic nervous system. Asian Ephedra have been used recently in the clandestine manufacture of a street drug, methamphetamine. Although ephedrine alkaloids are not detectable in New World species of Ephedra, together with Asian species they contain other nitrogen-containing secondary metabolites with known neuropharmacological activity. Many mesic and particularly xeric species worldwide accumulate substantial amounts of quinoline-2-carboxylic acids, or kynurenates, in their aerial parts. Many species of Ephedra accumulate cyclopropyl amino acid analogues of glutamate and proline in their stems and roots, and particularly in the seed endosperm. Mesic species synthesize substantial amounts of three L-2-(carboxycyclopropyl)glycine stereomers rarely seen in nature. A cyclopropyl analogue of proline with known antimicrobial activity, cis-3,4-methanoproline, is found in large amounts in the stems and seeds of many Ephedra species. The ability to synthesize cyclopropyl amino acids may be an ancestral feature in the taxon. The natural function in the taxon of these three groups of secondary compounds remains to be established.

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“…where: x 0 = culture fwt at time zero x t = culture fwt at time t t = unit time (days) t d = doubling time Methanol extracts of parent plant, callus and suspension culture tissues were analysed for alkaloids (Eph and Peph) on a Spectra Physics Model 8000 high performance liquid chromatograph (HPLC) and integrator with SP 770 UVvisible detector set at 210 nm, using the protocol of Barkan et al (1981). Normal phase thin layer chromatography (TLC) was also employed using 0.2mm thick Silica Gel Gr0F254 aluminium backed plates (Merck); solvent system, butan-1-01: glacial acetic acid: water (4:1:1); localisation agent = ninhydrin.…”

Section: E Andina Poepp and Endl Cell Suspensionsmentioning

confidence: 99%

Callus production, suspension culture and in vitro alkaloid yields of Ephedra

O'Dowd

McCauley

Richardson

et al. 1993

Plant Cell Tiss Organ Cult

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The effects of a range of plant growth regulators on callus production in various Ephedra species were examined. Species examined were E. andina, E. distachya, E. equisitina, E. fragilis var, camplyopoda, E. gerardiana, E. intermedia, E. major ssp procera, E. minima and E. saxatilis. All species produced callus on modified MS medium supplemented with 0.25 p~M kinetin and 5.0 p,M 2,4-dichlorophenoxyacetic acid or 1-naphthaleneacetic acid. Neither indole-3-acetic acid nor 3-indolebutyric acid induced significant callus formation but the latter maintained growth of established callus cultures in several species. Suspension cultures of several species were established in MS medium supplemented with 0.25 ~M kinetin and 5.0 ~M 2,4-dichlorophenoxyacetic acid or 1-naphthaleneacetic acid. Sustained fresh weight doubling times of 70 ---7 h were recorded for cell suspension cultures of E. andina grown in a semi-continuous air-lift bubble bioreactor and a minimum doubling time of 56 h was recorded for E. andina in batch culture. It also proved possible to immobilise E. andina batch cultures in sodium alginate beads. Neither parent plants or in vitro cultures of E. distachya, E. fragilis or E. saxatilis produced alkaloids. Trace quantities of 1-ephedrine and trace-0.14% dwt d-pseudoephedrine were produced by in vitro cultures of other species. The ability to produce alkaloid diminished to zero with successive subcultures.Abbreviations: Eph-1-ephedrine, Peph-d-pseudoephedrine, RGR-relative growth rate, KINkinetin, 2,4-D -2,4-dichlorophenoxyacetic acid, NAA -1-naphthaleneacetic acid, IBA -3-indolebutyric acid, IAA-indole-3-acetic acid

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Determination of cross-contamination of the diastereomers ephedrine and pseudoephedrine by high-performance liquid chromatography, thin-layer chromatography and carbon-13 nuclear magnetic resonance spectroscopy

Cited by 17 publications

References 8 publications

X Ephedra Species: In Vitro Culture, Micropropagation, and the Production of Ephedrine and Other Alkaloids

X Ephedra Species: In Vitro Culture, Micropropagation, and the Production of Ephedrine and Other Alkaloids

New observations on the secondary chemistry of world Ephedra (Ephedraceae)

Callus production, suspension culture and in vitro alkaloid yields of Ephedra

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