Berberine and coptisine free bases

Dostál, Jiřı́; Man, Stanislav; Sečkářová, Pavlı́na; Hulová, Dagmar; Nečas, Marek; Potáček, Milan; Toušek, Jaromı́r; Dommisse, Roger; Dongen, Walter Van; Marek, Radek

doi:10.1016/j.molstruc.2003.09.018

Cited by 36 publications

(20 citation statements)

References 28 publications

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“…This observation is in accordance with the fragmentation patterns obtained for other 8-substituted 7,8-dihydroprotoberberines. [20,23] Due to the lability of the C8-N1 bond and the extraordinary stability of the quaternary form, quaternary ions and heterocyclic bases were formed spontaneously during the ionization process. The EI-MS data for individual compounds are summarized in the Experimental section.…”

Section: Resultsmentioning

confidence: 99%

Covalent bonding of azoles to quaternary protoberberine alkaloids

Grycová

Hulová

Maier

et al. 2008

Magnetic Reson in Chemistry

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Adducts of the quaternary protoberberine alkaloids (QPA) berberine, palmatine, and coptisine were prepared with nucleophiles derived from pyrrole, pyrazole, imidazole, and 1,2,4-triazole. The products, 8-substituted 7,8-dihydroprotoberberines, were identified by mass spectrometry and 1D and 2D NMR spectroscopy, including (1)H--(15)N shift correlations at natural abundance. In addition, two adducts of QPA with chloroform and methanethiolate were characterized by using NMR data. Single-crystal X-ray structures of 8-pyrrolyl-7,8-dihydroberberine, 8-pyrazolyl-7,8-dihydroberberine, and 8-imidazolyl-7,8-dihydroberberine are also presented.

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Section: Resultsmentioning

confidence: 99%

Covalent bonding of azoles to quaternary protoberberine alkaloids

Grycová

Hulová

Maier

et al. 2008

Magnetic Reson in Chemistry

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“…Among the isoquinoline alkaloids, berberine, a natural plant alkaloid is the target of increased chemical and biological interest, because it has been found to possess potent anticancer activity 1,2 in addition to exhibiting antimalarial properties 2 . Berberine is found in herbs such as goldenseal, Berberis Aristata (Indian Bayberry), Oregon grape, barberry, and goldthread (Coptis chinensis), aimed at curbing bacterial, viral, fungal, yeast, and parasitic infections 2,3 Berberis species were widely used in both Ayurveda and Traditional Chinese medicine as a preventive therapy as well as to treat diabetes, cardiovascular diseases, weight management, cancer, dementia and ageing 1,2 .…”

Section: Introduction Berberinementioning

confidence: 99%

“…Berberine is found in herbs such as goldenseal, Berberis Aristata (Indian Bayberry), Oregon grape, barberry, and goldthread (Coptis chinensis), aimed at curbing bacterial, viral, fungal, yeast, and parasitic infections 2,3 Berberis species were widely used in both Ayurveda and Traditional Chinese medicine as a preventive therapy as well as to treat diabetes, cardiovascular diseases, weight management, cancer, dementia and ageing 1,2 . Berberine is one of the best studied plant alkaloid against Type 2 diabetes and metabolic syndrome.…”

Section: Introduction Berberinementioning

confidence: 99%

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Microwave assisted Subcritical water extraction of Berberine hydrochloride from the roots of Berberis Aristata using Harmony search algorithm

Manikyam¹,

Ck²,

Poluri³

et al. 2017

JHMR

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Microwave assisted Subcritical water extraction of Berberine hydrochloride from the roots of Berberis Aristata using Harmony search algorithmThe aim of present study is to optimize the conditions of Berberine extraction from roots of Berberis Aristata by Microwave assisted subcritical water extraction (MASCW).MASCW method of extraction had shown reproducibility in respect to time, solvent usage, yield and extraction repeatability. Isoquinone Berberine, is one of the wide spread representatives belonging to family of protoberberine alkaloids abundantly present in roots and stem parts of Indian barberry. The subcritical factors like time, solvent/ meal ratio, extraction repeatability, size of particles and temperature were investigated and were in accordance with experimental data and predicted data. Harmony search Algorithm (HSA) was used to study the effect of five subcritical parameters on the yield of Berberine .The extraction of berberine from roots of Berberis aristata was carried at 110-1700C using MASCW method using different variations of five subcritical parameters. The results show that all five factors (Time, Temperature, size of particles, repeatability of extraction and sample/liquid Ratio) have statistically significant effects on the berberine concentration. The results had suggested that experimental data concentration, 223.82 µg/ ml and predicted data concentration, 214.854 µg/ml of berberine are in significant correlation at subcritical parameters like temperature 1700C, particle size of 0.65 mm, time of 70 mins, solvent/meal ratio of 12 and at maximum three repetitions. Thus the extracted berberine was precipitated as berberine hydrochloride by acid and further evaluated for NMR structural studies which confirms with standard berberine hydrochloride.

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“…2 Currently, they still have medical interest. 3 For example, berberine, palmatine, and coptisine have been probed to inhibit dopamine biosynthesis. 4,5 These yellow dyes are highly fluorescent, seriously limiting the use of Raman spectroscopy to identify them.…”

Section: Introductionmentioning

confidence: 99%

Surface‐enhanced Raman scattering of protoberberine alkaloids

Cañamares

Lombardi

Leona

2008

J Raman Spectroscopy

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Quaternary protoberberine alkaloids are a class of natural dyes characterized by bright colors ranging from yellow to orange. As they present a strong fluorescence emission, their analysis by Raman spectroscopy is limited to specific techniques such as Fourier transform (FT)-Raman and spectral shift Raman techniques such as shifted subtracted Raman difference spectroscopy (SSRDS) and shifted excitation Raman difference spectroscopy (SERDS). In a previous article, we successfully used surface-enhanced Raman scattering (SERS) in the analysis of the alkaloid dye berberine in an ancient textile. The examination of the Raman and SERS spectra of berberine in combination with density functional theory (DFT) calculations indicated a flat adsorption geometry of the molecule on the Ag surface. In this article we extend that work to the study of related protoberberine alkaloids, palmatine, jatrorrhizine, and coptisine. The same adsorption geometry as in berberine was deduced. We found that the four alkaloids, although minimally different in their chemical structures, could be differentiated by the position of marker bands. Those bands are the most enhanced ones in the SERS spectra, which appear in the 700-800 cm −1 region.

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Berberine and coptisine free bases

Cited by 36 publications

References 28 publications

Covalent bonding of azoles to quaternary protoberberine alkaloids

Covalent bonding of azoles to quaternary protoberberine alkaloids

Microwave assisted Subcritical water extraction of Berberine hydrochloride from the roots of Berberis Aristata using Harmony search algorithm

Surface‐enhanced Raman scattering of protoberberine alkaloids

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