Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Roman, Maciej; Chruszcz‐Lipska, Katarzyna; Barańska, Małgorzata

doi:10.1002/jrs.4724

Cited by 9 publications

(11 citation statements)

References 56 publications

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“…ROA allowed unequivocal identification of the pseudoenantiomers based on the sign of the characteristic bands from a single measurement. The experiments were supported by theoretical calculations including conformational analysis followed by wavenumber calculations and Potential Energy Distribution (PED) analysis …”

Section: Vibrational Studies In Chemistrymentioning

confidence: 67%

Recent advances in linear and non‐linear Raman spectroscopy. Part X

Nafie

2016

J Raman Spectroscopy

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This review, published annually, provides an overview of advances in the field of Raman spectroscopy as found in papers published in the preceding calendar year in the Journal of Raman Spectroscopy (JRS), as well as in trends over the past decade across journals that have published papers important to the field of Raman spectroscopy. This information is obtained from statistical data on article counts obtained from Thomson Reuters ISI Web of Science Core Collection by year and by subfield of Raman spectroscopy. Additional information is gleaned from presentations at the XXV International Conference on Raman Spectroscopy (ICORS 2016) in Forteleza, Brazil in August 2016 and those featuring Raman scattering at SCIX 2016 organized by the Federation of Analytical Chemistry and Spectroscopy Societies (FACSS) in Minneapolis, Minnesota, USA in September 2016. Coverage is also provided for topics from the conference ECONOS 2016 held in April in Göteborg, Sweden and GeoRaman 2016 in June in Novosibirsk, Russia. Finally, papers published in JRS in 2015 are highlighted and arragned by topics at the frontier of Raman spectroscopy. From these various perspectives, it is clear that Raman spectroscopy continues to be a rapidly expanding field that provides sensitive photonic information of matter at the molecular level in an ever‐widening arena of novel applications. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Vibrational Studies In Chemistrymentioning

confidence: 67%

Recent advances in linear and non‐linear Raman spectroscopy. Part X

Nafie

2016

J Raman Spectroscopy

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“…Overall, our assignments are in good agreement with previous reports that discuss the topic in greater detail. 28,53,54…”

Section: Resultsmentioning

confidence: 99%

New Insights into Quinine–DNA Binding Using Raman Spectroscopy and Molecular Dynamics Simulations

et al. 2018

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Quinine’s ability to bind DNA and potentially inhibit transcription and translation has been examined as a mode of action for its antimalarial activity. UV absorption and fluorescence-based studies have lacked the chemical specificity to develop an unambiguous molecular-level picture of the binding interaction. To address this, we use Raman spectroscopy and molecular dynamics (MD) to investigate quinine—DNA interactions. We demonstrate that quinine’s strongest Raman band in the fingerprint region, which derives from a symmetric stretching mode of the quinoline ring, is highly sensitive to the local chemical environment and pH. The frequency shifts observed for this mode in solvents of varying polarity can be explained in terms of the Stark effect using a simple Onsager solvation model, indicating that the vibration reports on the local electrostatic environment. However, specific chemical interactions between the quinoline ring and its environment, such as hydrogen bonding and π-stacking, perturb the frequency of this mode in a more complicated but predictable manner. We use this vibration as a spectroscopic probe to investigate the binding interaction between quinine and DNA. We find that, when the quinoline ring is protonated, quinine weakly intercalates into DNA by forming π-stacking interactions with the base pairs. The Raman spectra indicate that quinine can intercalate into DNA with a ratio reaching up to roughly one molecule per 25 base pairs. Our results are confirmed by MD simulations, which also show that the quinoline ring adopts a t-shaped π-stacking geometry with the DNA base pairs, whereas the quinuclidine head group weakly interacts with the phosphate backbone in the minor groove. We expect that the spectral correlations determined here will enable future studies to probe quinine’s antimalarial activities, such as disrupting hemozoin biocrystallization, which is hypothesized to be, among other things, one of its primary modes of action against Plasmodium parasites.

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“…is based on a photometric determination of quinine (348 nm) and cinchonine-type (316 nm) alkaloids. Research papers mainly emphasized on the separation of the dominant representatives utilizing TLC [7], isotachophoresis [8], aqueous [9] and non-aqueous CE [10], vibrational spectroscopy [11], NMR [12] and HPLC [3,6,13–16]. For example, Hoffmann et al utilized a chiral strong cation exchange material to excellently resolve eight Cinchona alkaloids in 15 min, yet an application to plant material is missing [16].…”

Section: Introductionmentioning

confidence: 99%

Quantitative determination of major alkaloids in Cinchona bark by Supercritical Fluid Chromatography

Murauer

Ganzera

2018

Journal of Chromatography A

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Chinoline alkaloids found in Cinchona bark still play an important role in medicine, for example as anti-malarial and antiarrhythmic drugs. For the first time Supercritical Fluid Chromatography has been utilized for their separation. Six respective derivatives (dihydroquinidine, dihydroquinine, quinidine, quinine, cinchonine and cinchonidine) could be resolved in less than 7 min, and three of them quantified in crude plant extracts. The optimum stationary phase showed to be an Acquity UPC2 Torus DEA 1.7 µm column, the mobile phase comprised of CO2, acetonitrile, methanol and diethylamine. Method validation confirmed that the procedure is selective, accurate (recovery rates from 97.2% to 103.7%), precise (intra-day ≤2.2%, inter-day ≤3.0%) and linear (R2 ≥ 0.999); at 275 nm the observed detection limits were always below 2.5 µg/ml. In all of the samples analyzed cinchonine dominated (1.87%–2.30%), followed by quinine and cinchonidine. Their total content ranged from 4.75% to 5.20%. These values are in good agreement with published data, so that due to unmatched speed and environmental friendly character SFC is definitely an excellent alternative for the analysis of these important natural products.

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Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Cited by 9 publications

References 56 publications

Recent advances in linear and non‐linear Raman spectroscopy. Part X

Recent advances in linear and non‐linear Raman spectroscopy. Part X

New Insights into Quinine–DNA Binding Using Raman Spectroscopy and Molecular Dynamics Simulations

Quantitative determination of major alkaloids in Cinchona bark by Supercritical Fluid Chromatography

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