Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Sci Rep. 2024 Nov 5;14(1):26757. doi: 10.1038/s41598-024-78415-1.

Possibilities and limitations of computer assisted chiral HPLC method 
development for ozanimod on polysaccharide based chiral stationary phases.

Ferencz E(#)(1), Szabó ZI(#)(1)(2), Zöldhegyi A(3), Dombi G(4)(5), Molnár 
G(4)(5), Dobó M(4)(5), Varga E(1), Molnár I(3), Tóth G(6)(7).

Author information:
(1)George Emil Palade University of Medicine, Pharmacy, Science, and Technology 
of Targu Mures, Târgu Mureş, Romania.
(2)Sz-imfidum Ltd, Lunga, 525401, Romania.
(3)Molnár-Institute for Applied Chromatography, Berlin, Germany.
(4)Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes E. u. 
9, Budapest, 1092, Hungary.
(5)Center for Pharmacology and Drug Research & Development, Semmelweis 
University, Budapest, Hungary.
(6)Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes E. u. 
9, Budapest, 1092, Hungary. toth.gergo@semmelweis.hu.
(7)Center for Pharmacology and Drug Research & Development, Semmelweis 
University, Budapest, Hungary. toth.gergo@semmelweis.hu.
(#)Contributed equally

In this study, a direct HPLC method was developed to determine the enantiomeric 
purity of the immunomodulatory drug, ozanimod. A systematic method development 
process was followed, incorporating risk assessment, identification of critical 
analytical procedure parameters, initial screening of stationary phases, and 
software-assisted optimization of method parameters. Eight different 
polysaccharide-based chiral columns were selected to assess chiral separation of 
enantiomers under polar organic elution mode. The most promising results were 
obtained using a methanol:2-propanol mixture on the amylose-based Chiralpak AD 
column. Following this, systematic modeling was conducted using DryLab software 
to optimize method conditions, including isocratic eluent composition, 
temperature, and flow rate. Baseline separation was achieved within fifteen 
minutes using the optimized parameters: Chiralpak AD column thermostated at 
10 °C, and a mobile phase of methanol:2-propanol: diethylamine, 70:30:0.1 (v/v/v 
%), delivered at a flow rate of 0.8 mL/min. The developed method was validated 
according to current guidelines and in silico robustness testing was conducted 
to determine tolerance limits for critical separation parameters and their 
impact on enantioresolution. Our findings demonstrate the utility of DryLab, 
typically employed for reversed-phase achiral separations, in optimizing chiral 
methods even in polar organic mode. Limitations of the selected approach the 
development of chiral separation methods are also highlighted.

© 2024. The Author(s).

DOI: 10.1038/s41598-024-78415-1
PMCID: PMC11538454
PMID: 39500751 [Indexed for MEDLINE]

Conflict of interest statement: Imre Molnár is the founder, while Arnold 
Zöldhegyi is employed by Molnár-Institute for Applied Chromatography, the 
developer of the DryLab software. All other authors declare no competing 
financial interests or personal relationships that could have appeared to 
influence the work reported in this paper.


2. Pestic Biochem Physiol. 2024 Nov;205:106159. doi:
10.1016/j.pestbp.2024.106159.  Epub 2024 Sep 30.

Enantioselective effects of chiral profenofos on the conformation for human 
serum albumin.

Li W(1), Sun L(1), Yang X(1), Peng C(1), Hua R(2), Zhu M(3).

Author information:
(1)School of Chemical and Environmental Engineering, Anhui Polytechnic 
University, Wuhu, Anhui 241000, China.
(2)Key Laboratory of Agri-Food Safety of Anhui Province, School of Resources and 
Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 
230036, China.
(3)School of Chemical and Environmental Engineering, Anhui Polytechnic 
University, Wuhu, Anhui 241000, China. Electronic address: 
meiqingzhu@ahpu.edu.cn.

Profenofos, as a typical chiral organophosphorus pesticide, can cause various 
environmental problems and even endanger human health when used in excess. The 
toxicity of chiral profenofos was investigated through multispectral analysis, 
molecular docking, and density functional theory (DFT), employing human serum 
albumin (HSA) as the model protein. Fluorescence titration and lifetime 
measurements demonstrated that the interaction between chiral profenofos and HSA 
involves static quenching. Chiral profenofos forms a 1:1 complex with HSA at 
site II (subdomain IIIA), primarily driven by hydrophobic interactions and 
hydrogen bonds. Notably, the binding efficacy diminishes as temperature 
increases. Spectroscopic analyses confirm that chiral profenofos alters the 
microenvironment and structure of HSA, with the R-enantiomer exerting a greater 
impact than the S-enantiomer. Consequently, the toxicological implications of 
the R-profenofos is significantly more pronounced. Investigating the 
molecular-level toxic effects of chiral pesticides enhances the thoroughness of 
pesticide assessments, aids in understanding their distribution, metabolism, and 
associated risks, and facilitates the development of mitigation strategies.

Copyright © 2024 Elsevier Inc. All rights reserved.

DOI: 10.1016/j.pestbp.2024.106159
PMID: 39477612 [Indexed for MEDLINE]

Conflict of interest statement: Declaration of competing interest The authors 
declare that they have no known competing financial interests or personal 
relationships that could have appeared to influence the work reported in this 
paper.


3. Chem Res Toxicol. 2024 Oct 29. doi: 10.1021/acs.chemrestox.4c00344. Online
ahead  of print.

Deploying Validated Mass Spectrometry for Frontline Detection and Treatment of 
Human Poisoning by Long-Acting Anticoagulant Rodenticides.

van Breemen RB(1), Flores B(1), Rubinstein I(2), Feinstein DL(3).

Author information:
(1)Department of Pharmaceutical Sciences, Linus Pauling Institute and College of 
Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.
(2)Jesse Brown VA Medical Center and Department of Medicine, University of 
Illinois College of Medicine in Chicago, Chicago, Illinois 60612, United States.
(3)Jesse Brown VA Medical Center and Department of Anesthesiology, University of 
Illinois College of Medicine in Chicago, Chicago, Illinois 60612, United States.

Derived from the same natural anticoagulant as warfarin (dicoumarol), 
long-acting anticoagulant rodenticides (LAARs) or superwarfarins have much 
longer half-lives in human blood than warfarin (weeks instead of hours) and are 
more potent inhibitors of the same enzyme, vitamin K epoxide reductase component 
1. While used effectively worldwide as rodenticides, LAARs can elicit severe, 
protracted, life-threatening coagulopathy in humans at blood concentrations >10 
ng/mL leading to numerous accidental and intentional poisonings annually. To 
facilitate timely identification and quantitative analysis of LAARs in patients 
presenting unexplained severe, protracted, life-threatening coagulopathy, 
several analytical methods have been developed, all of which are based on 
electrospray liquid chromatography-mass spectrometry (LC-MS). In this 
perspective, we evaluated and compared these LC-MS methods in terms of 
validation, simultaneous detection of multiple LAARs, measurement of individual 
stereoisomers, and clinical applications.

DOI: 10.1021/acs.chemrestox.4c00344
PMID: 39471166


4. Mikrochim Acta. 2024 Oct 28;191(11):704. doi: 10.1007/s00604-024-06788-1.

Preparation of D-NCCDs and its application in fluorescent/colorimetric dual-mode 
discrimination of glutamine enantiomers.

Liao X(#)(1), Lu C(#)(1), Duan Y(1), Ren C(2), Chen H(1).

Author information:
(1)State Key Laboratory of Applied Organic Chemistry, College of Chemistry and 
Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of 
China.
(2)State Key Laboratory of Applied Organic Chemistry, College of Chemistry and 
Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of 
China. rencl@lzu.edu.cn.
(#)Contributed equally

A new type of carbon dots (D-NCCDs) was synthesized by 3, 5-diaminobenzoic acid, 
N,N-dimethyl-o-phenylenediamine, and D-cysteine. The morphology and structure of 
D-NCCDs were investigated by transmission electron microscopy (TEM), X-ray 
photoelectron spectroscopy (XPS), and FT-IR spectra, and the chirality was 
characterized by circular dichroism. In the presence of hydrogen peroxide, the 
fluorescence of D-NCCDs at 487 nm (λex = 410 nm) showed great discrimination 
ability towards glutamine enantiomers. The ratio of fluorescence intensity 
(F/F0) to the concentration of D-Gln showed good linearity in the range 
0.5-10 mM, with a detection limits of 0.11 mM. Meanwhile, the color of the 
solution gradually changed from light yellow to yellow-brown. The UV-Vis 
absorption ratio (A/A0) at 410 nm showed good linearity with the concentration 
of D-Gln in the range 0.5 to 20 mM; the detection limit is 7.7 μM. But the 
fluorescence and absorbance of D-NCCDs showed no significant change after the 
addition of L-glutamine. Thus, fluorescence and colorimetry dual-mode 
discrimination of glutamine enantiomers was achieved. The fluorescence 
enantioselectivity of Gln (FL-Gln/FD-Gln) is 1.62, and the colorimetric 
enantioselectivity of Gln (AD-Gln/AL-Gln) is 2.14. The chiral discrimination 
mechanism of D-NCCDs to Gln enantiomers was also investigated systematically. 
This work not only can discriminate glutamine enantiomers with high sensitivity 
and convenience, but also offers a new strategy for preparing new dual mode 
chiral nanoprobes.

© 2024. The Author(s), under exclusive licence to Springer-Verlag GmbH Austria, 
part of Springer Nature.

DOI: 10.1007/s00604-024-06788-1
PMID: 39467880 [Indexed for MEDLINE]


5. J Agric Food Chem. 2024 Nov 6;72(44):24191-24197. doi:
10.1021/acs.jafc.4c07615.  Epub 2024 Oct 28.

Streamlined Synthesis of Ellagitannins: Site-Selective Functionalization of the 
Glucose Core and Stereodivergent Construction of the Hexahydroxydiphenoic 
Groups.

Ueda Y(1), Kawabata T(2).

Author information:
(1)Interdisciplinary Research Center for Catalytic Chemistry, National Institute 
of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 
Higashi, Tsukuba, Ibaraki 305-8565, Japan.
(2)Department of Pharmaceutical Sciences, International University of Health and 
Welfare, 137-1 Enokizu, Okawa, Fukuoka 831-8501, Japan.

Ellagitannins are a class of plant polyphenols with a structural diversity of 
around 1000. Because those with attractive biological activities have been 
reported, synthetic studies have been performed. The purpose of this perspective 
is to provide an outlook toward future developments on ellagitannin chemistry 
and medicinal applications by overviewing synthetic studies. In particular, we 
summarize recent synthetic efforts of ellagitannins via functionalization of the 
glucose core and stereodivergent construction of the characteristic 
hydroxydiphenoic groups. The development of chemical probes utilizing natural 
ellagitannins is also introduced.

DOI: 10.1021/acs.jafc.4c07615
PMID: 39465500 [Indexed for MEDLINE]