Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Anal Bioanal Chem. 2024 Nov 5. doi: 10.1007/s00216-024-05619-9. Online ahead
of  print.

Hydrophobic deep eutectic solvent-ferrofluid microextraction followed by liquid 
chromatography-mass spectrometry for the enantioselective determination of 
chiral agrochemicals in natural waters.

Lucci E(1), Falcinelli G(1), Antonelli L(1), Dal Bosco C(1), Felli N(1), De 
Cesaris MG(1), Gentili A(2).

Author information:
(1)Department of Chemistry, Sapienza University, P.Le Aldo Moro 5, 00185, Rome, 
Italy.
(2)Department of Chemistry, Sapienza University, P.Le Aldo Moro 5, 00185, Rome, 
Italy. alessandra.gentili@uniroma1.it.

The increasing use of chiral agrochemicals sold as racemic formulations raises 
concern for the negative impacts that inactive enantiomers can have on aquatic 
life and human health. The present work just focuses on the determination of ten 
chiral pesticides in river water samples by applying a ferrofluid-based 
microextraction followed by their stereoselective liquid chromatography 
analysis. To develop the ferrofluid, magnetite nanoparticles were prepared and 
coated with oleic acid and then dispersed in a hydrophobic natural deep eutectic 
solvent (NaDES), composed of L-menthol and thymol (1:1). The stable colloidal 
dispersion was characterised by scanning electron microscopy, thermogravimetric 
analysis, energy-dispersive X-ray spectroscopy and attenuated total reflection 
Fourier transform infrared spectroscopy. The analyte microextraction from 5 ml 
river samples was performed using 50 µl of ferrofluid, while acidified 
acetonitrile (150 µl) was used to break down the ferrofluid and solubilise the 
NaDES containing the analytes. All the extracts were analysed by 
high-performance liquid chromatography-tandem mass spectrometry. For each 
analyte, the baseline separation of isomers was achieved on a Lux i-Amylose-3 
column (amylose tris(3-chloro-5-methylphenylcarbamate) working in reversed-phase 
mode; the combination with mass spectrometry detection allows the overall 
separation of 24 isomers (ten chiral analytes among which eight containing a 
single (one) chiral centre, one with two chiral centres and the last one 
existing in four stereoisomeric forms, due to the presence of two regioisomers 
with a chiral carbon) within 37 min. The method showed very good figures of 
merit in terms of recoveries (77.7-97.5%), intra-day and inter-day precision 
(2.7-7.7% and 6.9-14.9%, respectively), limit of detection (0.01-0.35 µg/L), 
limit of quantitation (0.03-1.20 µg/L), linear dynamic range, and intra-day and 
inter-day accuracy (1.2-14.8% and 1.8-15.0%, respectively). The presented method 
was able to detect 14 out of 24 isomers at the preventive limit established by 
the Italian legislation for single pesticide (that for a chiral pesticide is the 
sum of all its isomers) in surface waters, set at 0.1 µg/l. Finally, the method 
was evaluated using AGREEprep and ComplexGAPI metrics, compared with other 
ferrofluid-based methods, and applied to the analysis of water samples from two 
Italian rivers (the Nera River and the Tiber River), providing to be sustainable 
and reliable for the application to real river matrices.

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

DOI: 10.1007/s00216-024-05619-9
PMID: 39499279


2. ACS Omega. 2024 Oct 16;9(43):43927-43939. doi: 10.1021/acsomega.4c07565. 
eCollection 2024 Oct 29.

Bactericidal and Synergistic Effects of Lippia origanoides Essential Oil and Its 
Main Constituents against Multidrug-Resistant Strains of Acinetobacter 
baumannii.

da Silva AT(1), Cândido AECM(1), Júnior EDCM(1), do É GN(1), Moura MPS(2), Souza 
RFS(1), Guimarães ML(3), Peixoto RM(1), de Oliveira HP(3), da Costa MM(1).

Author information:
(1)Animal Microbiology and Immunology Laboratory, Universidade Federal do Vale 
do São Francisco (UNIVASF), Campus Agricultural Sciences, Petrolina, Pernambuco 
56300-000, Brazil.
(2)College of Pharmaceutical Sciences (CFARM), Universidade Federal do Vale do 
São Francisco (UNIVASF), Av. José de Sá Maniçoba, Centro, Petrolina, Pernambuco 
56304-205, Brazil.
(3)Laboratory of Impedance Spectroscopy and Organic Materials, Institute of 
Materials Science, Universidade Federal do Vale do São Francisco (UNIVASF), 
Juazeiro, Bahia 48902-300, Brazil.

Bacterial resistance in Acinetobacter baumannii is a significant public health 
challenge, as these bacteria can evade multiple antibiotics, leading to 
difficult-to-treat infections with high mortality rates. As part of the search 
for alternatives, essential oils from medicinal plants have shown promising 
antibacterial potential due to their diverse chemical constituents. This study 
evaluated the antibacterial, antibiofilm, and synergistic activities of the 
essential oil of Lippia origanoides (EOLo) and its main constituents against 
multidrug-resistant clinical isolates of A. baumannii. Additionally, the 
antibacterial and antibiofilm potential of a nanoemulsion containing carvacrol 
(NE-CAR) was assessed. EOLo was extracted through hydrodistillation, and its 
components were identified via gas chromatography coupled with mass 
spectrometry. The A. baumannii isolates (n = 9) were identified and tested for 
antimicrobial susceptibility using standard disk diffusion methods. 
Antibacterial activity was determined by broth microdilution, while antibiofilm 
activity was measured using colorimetric methods with crystal violet and 
scanning electron microscopy. Synergism tests with antibiotics (meropenem, 
ciprofloxacin, gentamicin, and ampicillin+sulbactam) were performed using the 
checkerboard method. The primary constituents of EOLo included carvacrol 
(48.44%), p-cymene (14.58%), and thymol (10.16%). EOLo, carvacrol, and thymol 
demonstrated significant antibacterial activity, with carvacrol showing the 
strongest effect. They were also effective in reducing biofilm formation, as was 
NE-CAR. The combinations with antibiotics revealed significant synergistic 
effects, lowering the minimum inhibitory concentration of the tested 
antibiotics. Therefore, this study confirms the notable antibacterial activity 
of the essential oil of L. origanoides and its constituents, especially 
carvacrol, suggesting its potential as a therapeutic alternative for A. 
baumannii infections.

© 2024 The Authors. Published by American Chemical Society.

DOI: 10.1021/acsomega.4c07565
PMCID: PMC11525495
PMID: 39493982

Conflict of interest statement: The authors declare no competing financial 
interest.


3. RSC Med Chem. 2024 Oct 9. doi: 10.1039/d4md00511b. Online ahead of print.

Azo derivatives of monoterpenes as anti-Helicobacter pylori agents: from 
synthesis to structure-based target investigation.

Melfi F(1), Fantacuzzi M(1), Carradori S(1), D'Agostino I(2), Ammazzalorso A(1), 
Mencarelli N(1), Gallorini M(1), Spano M(3), Guglielmi P(3), Agamennone M(1), 
Haji Ali S(4)(5), Al-Samydai A(6), Sisto F(7).

Author information:
(1)Department of Pharmacy, "G. d'Annunzio" University of Chieti-Pescara via dei 
Vestini 31 66100 Chieti Italy simone.carradori@unich.it.
(2)Department of Pharmacy, Univerity of Pisa Via Bonanno 6 56126 Pisa Italy.
(3)Department of Drug Chemistry and Technology, "Sapienza" University of Rome 
P.le Aldo Moro 5 00185 Rome Italy.
(4)Department of Pharmaceutical Chemistry, College of Pharmacy, Hawler Medical 
University Erbil 44000 Iraq.
(5)Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu 
University Eskişehir 26470 Turkey.
(6)Pharmacological and Diagnostic Research Centre (PDRC), Faculty of Pharmacy, 
Al-Ahliyya Amman University Amman-Jordan- Al Salt Road Amman 19328 Jordan.
(7)Department of Biomedical, Surgical and Dental Sciences, University of Milan 
Via Pascal 36 20133 Milan Italy.

Helicobacter pylori (Hp) infection affects nearly half of the global population. 
Current therapeutic options include the administration of a combination of 
antibiotics and proton pump inhibitors, although antimicrobial resistance rise 
remains a big concern. Phenolic monoterpenes, e.g., eugenol, vanillin, 
carvacrol, and thymol, have always attracted researchers for their multifaced 
biological activities and the possibility to be easily derivatized. Thereby, 
herein we present the functionalization of such compounds through the 
conventional aryl diazotization reaction, generating a series of mono- and 
bis-azo derivatives (1-28). Also, to continue previous studies, we investigated 
the role of the free phenolic moiety of thymol with eight compounds (29-36). The 
compounds were tested against four Hp strains including three clinical isolates, 
finding some potent and selective inhibitors of bacterial growth. Thus, the 
representative compounds underwent in vitro cytotoxicity evaluation on two 
normal cell lines and putative target investigation by performing a 
structure-based approach based on docking calculations on some of the most 
studied pharmacological targets for Hp, e.g., urease, β-hydroxyacyl-acyl carrier 
protein dehydratase, glucose 6-phosphate dehydrogenase, and inosine 
5'-monophosphate dehydrogenase.

This journal is © The Royal Society of Chemistry.

DOI: 10.1039/d4md00511b
PMCID: PMC11526209
PMID: 39493229

Conflict of interest statement: The authors declare no conflict of interest.


4. Chemosphere. 2024 Nov 2:143666. doi: 10.1016/j.chemosphere.2024.143666. Online
 ahead of print.

Comparative Ecotoxicity Assessment of highly bioactive Isomeric monoterpenes 
carvacrol and thymol on aquatic and edaphic indicators and communities.

Gan C(1), Langa E(2), Ballestero D(3), Pino-Otín MR(4).

Author information:
(1)Universidad San Jorge. Villanueva de Gállego, 50830 Zaragoza, Spain. 
Electronic address: cgan@usj.es.
(2)Universidad San Jorge. Villanueva de Gállego, 50830 Zaragoza, Spain. 
Electronic address: elanga@usj.es.
(3)Universidad San Jorge. Villanueva de Gállego, 50830 Zaragoza, Spain. 
Electronic address: dballestero@usj.es.
(4)Universidad San Jorge. Villanueva de Gállego, 50830 Zaragoza, Spain. 
Electronic address: rpino@usj.es.

The growing demand for sustainable natural products to replace harmful synthetic 
ones requires comprehensive ecotoxicity assessments to ensure their eco-friendly 
nature. This study explored for the first time the changes in microbial 
community growth and metabolic profiles from river and natural soil samples 
exposed to the two structural isomers, thymol (THY) and carvacrol (CARV), 
utilizing Biolog EcoPlate™ assays and 16S rRNA gene sequencing for taxonomic 
analysis. In addition, we addressed existing ecotoxicity data gaps for these two 
compounds by using aquatic (Daphnia magna and Vibrio fischeri) and soil (Eisenia 
fetida and Allium cepa) indicators. Results show acute toxicity of both CARV and 
THY on all indicators. V. fischeri (LC50=0.59 mg/L) >D. magna (4.75 mg/L) >A. 
cepa (6.47 mg/L) for CARV, and V. fischeri (LC50=1.71 mg/L) >A. cepa (4.05 mg/L) 
>D. magna (8.13 mg/L) for THY. E. fetida showed LC50 = 7.68 mg/Kg for THY and 
1.04 for CARV. River and soil microbial communities showed resilience, likely 
because they contain taxa capable of biodegrading these products. No significant 
growth inhibition effects were observed up to 100 mg/L, though substrate 
utilization decreased at higher concentrations, particularly for polymers and 
amines in soil microorganisms and polymers in aquatic communities. Soil 
microorganisms were more affected than aquatic ones, with CARV being more toxic 
than THY (EC50120h = THY 94.13 and CARV 29.79 mg/L in soil microorganisms). 
These findings suggest that an increase in the consumption of these products and 
their subsequent ecotoxicity effects from environmental discharge should still 
be monitored before being ruled out. However, long-term effects are unlikely due 
to microbial degradation of these natural products, potentially reducing risks 
to other target species and opening the way for their use as substitutes for 
commercial antibiotics.

Copyright © 2024. Published by Elsevier Ltd.

DOI: 10.1016/j.chemosphere.2024.143666
PMID: 39491687

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.


5. Sci Rep. 2024 Nov 3;14(1):26487. doi: 10.1038/s41598-024-77524-1.

Identification, characterization, and sensitivity to phytochemicals of a novel 
Curvularia species associated with leaf spot disease on Curcuma kwangsiensis.

Wang H(#)(1)(2), Wei R(#)(3), Wei Y(1), Su J(1), Xu J(1), Yao M(1), Tian D(1), 
Zhou H(4).

Author information:
(1)Guangxi Key Laboratory for Polysaccharide Materials and Modifications, 
Guangxi Minzu University, Nanning, 530006, China.
(2)Linnaeus Labs Technology Company Limited, Wuyuan, 333200, China.
(3)Cash Crops Research Institute, Guangxi Academy of Agricultural Sciences, 
Nanning, 530007, China.
(4)Guangxi Key Laboratory for Polysaccharide Materials and Modifications, 
Guangxi Minzu University, Nanning, 530006, China. zhouhao@gxmzu.edu.cn.
(#)Contributed equally

A leaf spot disease affecting Curcuma kwangsiensis (Zingiberaceae) has been 
observed in Qinzhou City, Guangxi Province. Infected leaves exhibit yellow-brown 
spots that progressively expand and eventually lead to leaf death. Curvularia 
isolates were obtained from the diseased leaves with tissue isolation and single 
spore purification methods. To accurately identify these isolates, we analyzed 
their morphological characteristics and phylogenetic relationships using 
combinations of ITS, GAPDH, and EF-1α gene sequences. Phylogenetic analysis 
showed that the investigated strains formed a distinct clade separate from other 
recognized Curvularia species. Furthermore, the strains exhibited differences in 
conidiophore size and conidia shape/size. Based on phylogenetic studies, 
morphology, and pathogenicity tests, the pathogen was identified as a new 
species named Curvularia qinzhouensis. Optimal conditions for mycelial growth 
were observed at 30 °C and pH 8. The sensitivity of the pathogen to various 
phytochemicals was also examined. Honokiol, thymol, and citral demonstrated 
effective antifungal effects, with EC50 values of 6.72 ± 1.75, 25.74 ± 4.30, and 
54.24 ± 4.69 µg/ml, respectively. The present investigation provides the first 
report of leaf spot disease on C. kwangsiensis caused by C. qinzhouensis, and 
valuable insights for the prevention and control of this disease.

© 2024. The Author(s).

DOI: 10.1038/s41598-024-77524-1
PMCID: PMC11532394
PMID: 39489803 [Indexed for MEDLINE]

Conflict of interest statement: The authors declare no competing interests.