An alternative quantification approach called ERETIC (Electronic REference To access In vivo Concentrations) utilizing electronic reference-based proton nuclear magnetic resonance (¹H NMR) spectroscopy techniques has been successfully introduced in our present study to simultaneously determine the contents of five major active protoberberine alkaloids (berberine, coptisine, jatrorrhizine, palmatine and epiberberine) in Rhizoma Coptidis, one of the most commonly used traditional Chinese medicines (TCM). The NMR experimental conditions including deuterated solvent, relaxation delay time, and ERETIC transmitter power level were optimized, and the developed method was validated in terms of precision, reproducibility, stability, accuracy, recovery, and limit of quantification (LOQ). The recoveries of the five tested alkaloids ranged between 89.94 and 97.72% for berberine, 90.87 and 100.05% for coptisine, 98.35 and 107.57% for jatrorrhizine, 95.37 and 101.26% for palmatine, and 93.18 and 98.00% for epiberberine, respectively, and LOQ was 0.1 mM for berberine. The high universality, accuracy, reproducibility, and efficiency of the ERETIC method demonstrated in this work suggest that this method could serve as a highly potential quantification alternative for quality assessment of TCM.
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http://dx.doi.org/10.1016/j.jpba.2011.10.030 | DOI Listing |
Nat Commun
December 2024
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
The activation of C-C bond of benzocyclobutenones under mild reaction conditions remains a challenge. We herein report a photoinduced catalyst-free regio-specific C1-C8 bond cleavage of benzocyclobutenones, enabling the generation of versatile ortho-quinoid ketene methides for aza-[4 + 2]-cycloaddition with imines, which offers a facile route to isoquinolinone derivatives, including seven family members of protoberberine alkaloids, gusanlung A, B, D, 8-oxotetrahydroplamatine, tetrahydrothalifendine, tetrahydropalmatine, and xylopinine. Furthermore, the catalytic enantioselective version of this strategy is also realized by merging synergistic photocatalysis and chiral Lewis acid catalysis.
View Article and Find Full Text PDFBiochem Biophys Res Commun
January 2025
Joint National Laboratory for Antibody Drug Engineering, Henan University, Kaifeng, China; Kaifeng Key Lab for Cataract and Myopia, Institute of Eye Disease, Kaifeng Central Hospital, Kaifeng, China. Electronic address:
Coptisine (COP) is a natural protoberberine isoquinoline alkaloid that is isolated from Coptis chinensis and exhibits a variety of pharmacological activities, such as the inhibition of tumor growth, bacterial infection, inflammation and oxidative stress. In this study, COP penetrated and produced fluorescent signals in living tumor cell lines, primary MEF cells and polyformaldehyde-fixed cells. The fluorescent signal was detected at a wavelength of 488 nm.
View Article and Find Full Text PDFACS Synth Biol
December 2024
State Key Laboratory of Food Nutrition and Safety, Key Laboratory of Industrial Fermentation Microbiology of the Ministry of Education, Tianjin Key Laboratory of Industrial Microbiology, College of Biotechnology, Tianjin University of Science and Technology, No.29 the 13th Street TEDA, Tianjin 300457, PR China.
Benzylisoquinoline alkaloids (BIAs) are a class of natural compounds found in plants of the family, known for their diverse pharmacological activities. However, the extraction yields of BIAs from plants are limited, and the cost of chemical synthesis is prohibitively high. Recent advancements in systems metabolic engineering and genomics have made it feasible to use microbes as bioreactors for BIAs production.
View Article and Find Full Text PDFJ Phys Chem Lett
October 2024
ITODYS, Université Paris Cité and CNRS, 75006 Paris, France.
Palmatine is a protoberberine alkaloid, which may produce singlet oxygen under visible light irradiation and binds to DNA. The fact that singlet oxygen activation in palmatine may be triggered by environmental conditions, and in particular its interaction with nucleic acids, makes it a most suitable candidate for photodynamic therapy and DNA-targeted noninvasive anticancer strategies. Despite these remarkable properties, the actual binding mode between palmatine and DNA has not been resolved, yet.
View Article and Find Full Text PDFNat Prod Res
October 2024
College of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang, China.
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