Analysis of the Cinchona alkaloids by high-performance liquid chromatography and other separation techniques

McCalley, David V.

doi:10.1016/s0021-9673(01)01557-6

Cited by 81 publications

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“…Trifluoroacetic acid (0.1 mL) was mixed with 1.0 mL of methanold 4 to give an approximate concentration of 1.1 M with respect to TFA. The mixture was transferred to a 5-mm tube, and two 13 C NMR spectra were acquired with 24 hours in between measurements using a 400 MHz Bruker Avance DRX spectrometer (Bruker Biospin) at 300 K. The spectra were acquired with a pulse length corresponding to a 30°pulse, a spectral width of 24 kHz, collecting 1024 scans into 64 k data points with a relaxation delay of 4.0 sec.…”

Section: Test Of Esterificationmentioning

confidence: 99%

“…1) [1][2][3]. The most abundant alkaloid is quinine that accounts for 70-90 % of the total alkaloid content which can be as high as 25 % of the dry weight [4]. Even though there are effective artemisinin-based combination therapies against malaria, there is still an interest in using the bark of Cinchona species (Rubiaceae) for reasons of availability and evolved malaria drug resistance [5,6].…”

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“…Hence, a titration experiment was performed to find out a suitable amount of perchloric acid to add. A fixed amount of quinine (2 mg) was dissolved in a 1 : 1 mixture of chloroform-d 1 and methanol-d 4 . Perchloric acid was added in steps of 10 µL, and 1 H NMR spectra were acquired with the spectrometer locked on the deuterium signal from the methyl group of methanol-d 4 .…”

mentioning

confidence: 99%

“…A fixed amount of quinine (2 mg) was dissolved in a 1 : 1 mixture of chloroform-d 1 and methanol-d 4 . Perchloric acid was added in steps of 10 µL, and 1 H NMR spectra were acquired with the spectrometer locked on the deuterium signal from the methyl group of methanol-d 4 . It was found that after an addition of 70 µL of aqueous perchloric acid (70%), the position of the aromatic resonances of quinine was constant (with further changes smaller than the line widths) (l " Fig.…”

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Extraction of Alkaloids for NMR-Based Profiling: Exploratory Analysis of an Archaic Cinchona Bark Collection

2012

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Introduction !The crude drug cinchona (Cinchonae cortex) used against malaria is known since the colonization of South America in the beginning of the 17th century. The antimalarial effect is mainly due to the content of quinine (1), which interferes with the development of the Plasmodium parasites in the red blood cells [1]. Cinchona also contains the likewise active analogue alkaloids quinidine (2), cinchonine (3), and cinchonidine (4) (l " Fig. 1) [1][2][3]. The most abundant alkaloid is quinine that accounts for 70-90 % of the total alkaloid content which can be as high as 25 % of the dry weight [4]. Even though there are effective artemisinin-based combination therapies against malaria, there is still an interest in using the bark of Cinchona species (Rubiaceae) for reasons of availability and evolved malaria drug resistance [5,6]. As a result of the economical values of cinchona during the 19th century, plantations were spread to different tropical regions such as Indonesia and India. Different species and hybrids were tested for production of the drug in order to maximize the yield of quinine. During this period, samples of Cinchonae cortex were collected from different parts of the world and eventually ended up in a collection hosted by the Museum of Natural Medicine at the University of Copenhagen. A profiling study of this archaic collection, focused on alkaloids, could possibly indicate species that were not selected due to the quinine content but to other types of antimalarial alkaloids. Since the samples are collected over a long time period, from many different sites, and for many different reasons, we expect a large variation of types and amounts of alkaloids. Profiling of extracted alkaloids might indicate odd samples that contain other types of alkaloids than the expected and so allows finding out about the possible variations and combinations of the known and major alkaloids. NMR is a rational choice of analytical platform for this study. It is rapid, robust and gives reproducible results [7,8]. NMR also gives different spectra of diastereomers, and this makes it possible to differentiate between the main alkaloids. However, the traditional liquid-liquid extraction to separate alkaloids based on their basic properties is not practical for a profiling study in terms of sample throughput and potential problems with robustness. In this study, we present the use of a direct Abstract ! A museum collection of Cinchonae cortex samples (n = 117), from the period 1850-1950, was extracted with a mixture of chloroform-d 1 , methanol-d 4 , water-d 2 , and perchloric acid in the ratios 5 : 5 : 1 : 1. The extracts were directly analyzed using 1 H NMR spectroscopy (600 MHz) and the spectra evaluated using principal component analysis (PCA) and total statistical correlation spectroscopy (STOCSY). A new method called STOCSY-CA, where CA stands for component analysis, is described, and an analysis using this method is presented. It was found that the samples had a rather homogenous content of the well-known cinc...

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Section: Test Of Esterificationmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Extraction of Alkaloids for NMR-Based Profiling: Exploratory Analysis of an Archaic Cinchona Bark Collection

2012

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“…al., 2006;Mariath et al, 2009). A droga contém de 7-12% de alcalóides totais dos quais a quinina (1) representa 70-90% e quinidina (2) até 1% (McCalley, 2002, Barbosa-Filho et al, 2005. Diferentes parâmetros de extração são aplicados na otimização de métodos utilizados no controle de qualidade de fitoterápicos (Helou, 1987(Helou, -1989Luz et al, 1997Luz et al, -1998Aragão et al, 2000;Costa, 2002;Brandão et al, 2006Brandão et al, , 2008Veiga-Junior & Mello, 2008;Bueno & Bastos, 2009).…”

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Avaliação de parâmetros de extração da Cinchona Vahl por métodos farmacopéicos e não farmacopéicos

Silva¹,

Aragão²

2009

Rev. bras. farmacogn.

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RESUMO:O presente estudo teve como objetivo a otimização de parâmetros cinéticos de extração da Cinchona pubescens Vahl por ultra-som, usando métodos farmacopéicos e não farmacopéicos. Na extração por ultrasom variaram-se o tempo, a massa, a faixa granulométrica, o volume de solvente e o tipo de solvente. Na decocção, as extrações foram feitas no tempo e temperatura descrita na Farmacopéia Brasileira IV, variando-se o sistema solvente. Na extração por maceração variaram-se o tempo e o sistema solvente. O teor de alcalóides quinolínicos foi monitorado por espectrofotometria no UV a 325 nm. O método decocção foi o que apresentou o maior rendimento na extração dos alcalóides, dados equivalentes foram conseguidos com o método ultra-som, no tempo de 5 min e solvente acidificado pH 4, com um rendimento maior ao da maceração. Pela aplicação do planejamento fatorial para o método do ultra-som foi visto que há uma interação entre as variáveis, necessitando de um melhor ajuste entre elas a fim de melhorar a eficiência extrativa do método do ultra-som.Unitermos: Cinchona pubescens, Rubiaceae, farmacopéia, ultra-som, decocção, maceração.ABSTRACT: "Extraction parameters from Cinchona pubescens Vahl using pharmacopeia and no pharmacopeia methods". The present study for ultrasound had as objective the optimization of kinetic parameters of extraction of the Cinchona pubescens Vahl, using pharmacopeia and no pharmacopeia methods. In the extraction for ultrasound they had varied the time, the solvent type, the mass, the volume of solvent and grain size of the sample. In the decoction, the extractions had been made according to the time and temperature described in Brazilian Pharmacopeia IV, varying the solvent system. In the extraction for maceration the time and the solvent system had varied. The alkali of the Cinchona pubescens Vahl, was monitored by spectrophotometry in UV 325 nm. The method decoction was the one that presented the biggest income in the alkaloids extraction, given equivalent data had been obtained with the method ultrasound, in the solvent acidified pH 4 and time of 5 min, with a bigger income than the one of the maceration.

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Alkaloids, Pharmaceutical Analysis of

Gilpin

2000

Encyclopedia of Analytical Chemistry

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As a major class of compounds, alkaloids are naturally occurring bases with a wide range of structures, chemical, and physical properties, and pharmacological activities. The use of alkaloids as medical agents in the form of crude plant powders and extracts predates the modern pharmaceutical industry by almost four millennia and in some instances prior to modern science. Mass poisonings have resulted from their inadvertent usage and was prevalent in Europe during the Middle Ages as the result of the general populace eating bread contaminated with Claviceps purpurea . The C. purpurea fungus produces an ergot alkaloid that first affects the central nervous system causing hallucinogenic effects and later death if enough is ingested. Ergot poisoning in the Middles Ages is perhaps best known for its effect on the painters “of‐the‐day” and their impressionistic styles and use of vivid colors.

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Analysis of the Cinchona alkaloids by high-performance liquid chromatography and other separation techniques

Cited by 81 publications

References 45 publications

Extraction of Alkaloids for NMR-Based Profiling: Exploratory Analysis of an Archaic Cinchona Bark Collection

Extraction of Alkaloids for NMR-Based Profiling: Exploratory Analysis of an Archaic Cinchona Bark Collection

Avaliação de parâmetros de extração da Cinchona Vahl por métodos farmacopéicos e não farmacopéicos

Alkaloids, Pharmaceutical Analysis of

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