Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. 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.


2. Inorg Chem. 2024 Oct 29. doi: 10.1021/acs.inorgchem.4c03521. Online ahead of 
print.

Selective Oxidation of p-Cymene over Mesoporous LaCoO(3) by Introducing Oxygen 
Vacancies.

Zhang Q(1), Peng D(1)(2), Su ZA(1), Li A(1), Sun C(1), Wang L(1), Cui S(1), Yang 
S(1), Zheng X(1), Mo L(2), Zhang N(3), Gu F(4), Liu Y(1).

Author information:
(1)Department of Chemical Engineering, School of Petrochemical Engineering & 
Environment, Zhejiang Ocean University, Zhoushan 316022, China.
(2)National Engineering Research Center for Marine Aquaculture, Zhejiang Ocean 
University, Zhoushan 316022, PR China.
(3)Instrumental Analysis Center, Shanghai Jiao Tong University, 800 Dongchuan 
Road, Shanghai 200240, PR China.
(4)Jilin Province Product Quality Supervision and Inspection Institute, 2699 
Yiju Street, Changchun 130103, China.

The liquid-phase catalytic oxidation of p-cymene to 4-methylacetophenone is an 
industrially significant reaction. However, the targeted oxidation of a specific 
C-H bond of p-cymene is extremely difficult due to there being many branched 
chains in p-cymene. In here, we designed a simple method to synthesize 
mesoporous LaCoO3 catalysts with rich oxygen vacancy (Oov) sites. The 
as-prepared mesoporous LaCoO3 after 550 °C calcination (mLaCoO3) exhibits 
remarkable catalytic activity for solvent-free oxidation of the p-cymene 
reaction, with a selectivity of over 80.1% selectivity for 4-methylacetophenone 
and a conversion of 50.2% for p-cymene (120 °C, 3 MPa). Besides, recycling 
studies have demonstrated that the mLaCoO3 catalysts can be reused ten times in 
the aerobic oxidation of the p-cymene reaction without significant catalytic 
activity reduce. The experimental and characterization results indicated that 
the mesoporous structure of the catalyst is conducive to the generation of 
surface Oov, which can properly facilitate ion spread during the catalytic 
process and afford enough O2 for intermediate species, thus is beneficial for 
the generation of 4-methylacetophenone. This work demonstrates that the 
selectivity oxide p-cymene with an O2 employing mLaCoO3 catalyst is highly 
promising for chemical industrial applications.

DOI: 10.1021/acs.inorgchem.4c03521
PMID: 39472106


3. Asian Pac J Cancer Prev. 2024 Oct 1;25(10):3515-3524. doi: 
10.31557/APJCP.2024.25.10.3515.

Assessment of in vitro and in silico Antiproliferative Effects of p-Cymene and 
Its Naturally Occurring 7-Oxygenated Derivatives on Human Cancer Cell Lines.

Souza NP(1), Fontão APGA(2), Silva GWSE(2), Sampaio ALF(2), Mazzei JL(1)(3).

Author information:
(1)Post-Graduate Program of Translational Research on Drugs and Medicines, 
Institute of Drug Technology, Oswaldo Cruz Foundation, Brazil.
(2)Laboratory of Molecular Pharmacology, Department of Pharmacology, Institute 
of Drug Technology, Oswaldo Cruz Foundation, Brazil.
(3)Laboratory of Technology for Biodiversity in Health, Department of Natural 
Products, Institute of Drug Technology, Oswaldo Cruz Foundation, Brazil.

OBJECTIVE: To evaluate the in vitro and silico antiproliferation of p-cymene, 
cumin aldehyde, cuminic acid, and cuminol against human cancer cell lines 
(HCCLs). The sodium salt of the organic acid was included after synthesis.
METHODS: The quality of the compounds was verified using analytical methods. A 
primary screening of the compounds at 100 µM was conducted (n=6) on nine HCCLs 
(SK-MEL-28, K562, Lucena, Jurkat, Caco-2, MDA-MB-231, THP-1, U87-MG, and Calu-3) 
and HEK-293 through the MTT method after 48h-incubation. The viability curve and 
apoptotic and necrotic cell populations of cumin aldehyde-treated Calu-3 cells 
were determined. The statistical significance relative to the vehicle was 
evaluated using ANOVA and Dunnett. The possibility of being active (Pa) on HCCLs 
and biological targets was assessed in silico using CLC-Pred. Moreover, the 
ADMET properties were predicted using three servers.
RESULTS: Only cumin aldehyde induced a low and significant (31±5%, p<0.001) in 
vitro antiproliferation, and even then, only on the Calu-3 line (IC50 650 µM). 
Only necrosis was significant (p<0.01) with 300 µM after 24h. The absence 
(p>0.05) of in vitro activity on the other HCCLs corroborated the low in silico 
probability of being active (Pa≤0.33), except for cumin aldehyde on the 
MDA-MB-231 line (Pa=0.47). P-cymene was proven to be the most toxic compound to 
human health.
CONCLUSION: Excepting cumin aldehyde, the lack of the antiproliferation 
potential of these p-cymene derivatives was extensively demonstrated for the 
first time. Cuminaldehyde induced toxicity in a lung adenocarcinoma line, 
corroborating the literature. Six selective and three specific cell lines were 
proposed to evaluate the anticancer activity of the compounds in addressed 
studies, mainly involving those with Pa≥0.50. The inhibition of five targets 
seems to play a role in inducing HCCL antiproliferation. The ADMET estimated 
that cumin aldehyde, cuminol, and sodium cuminate are the safest compounds for 
human use.

DOI: 10.31557/APJCP.2024.25.10.3515
PMID: 39471017 [Indexed for MEDLINE]


4. Inorg Chem. 2024 Oct 28. doi: 10.1021/acs.inorgchem.4c03339. Online ahead of 
print.

Solvent- and Concentration-Induced Topological Transformation of a 
Ruthenium(II)-Based Trigonal Prism to a Triply Interlocked [2] Catenane.

Ali S(1), Rinshad VA(1), Mukherjee PS(1).

Author information:
(1)Department of Inorganic and Physical Chemistry, Indian Institute of Science, 
Bangalore 560012, India.

Synthesis of interlocked supramolecular cages has been a growing field of 
interest due to their structural diversity. Herein, we report the template-free 
synthesis of a Ru(II) triply interlocked [2] catenane using coordination-driven 
self-assembly. The self-assembly of a triazine-based tripyridyl donor L 
(2,4,6-tris(5-(pyridin-4-yl)thiophen-3-yl)-1,3,5-triazine) with a dinuclear 
Ru(II) acceptor M (Ru2(dhnq)(η6-p-cymene)2)(CF3SO3)2) yielded two distinct 
structures depending on the solvent and concentration. In methanol, a triply 
interlocked metalla [2] catenane (MC2) was formed, whereas in nitromethane, a 
non-interlocked cage (MC1) was obtained. The non-interlocked cage MC1 was 
gradually converted to MC2 in nitromethane by the increase in the concentration 
of cage MC1 from 0.5 to 9 mM. The interlocked cage (MC2) was stable after 
formation and was unaffected by the change in concentration. Notably, the free 
cage (MC1) exhibited host-guest interactions with polycyclic aromatic aldehydes, 
stabilizing the non-interlocked structure even at higher concentrations. In 
contrast, the triply interlocked [2] catenane (MC2) remains stable due to 
self-penetration and does not encapsulate guest molecules. This work showcases 
the stimuli-induced irreversible structural transformation of a triangular 
prismatic cage to its triply interlocked [2] catenane by employing metal-ligand 
coordination chemistry.

DOI: 10.1021/acs.inorgchem.4c03339
PMID: 39463351


5. Food Chem. 2024 Oct 16;464(Pt 2):141660. doi: 10.1016/j.foodchem.2024.141660. 
Online ahead of print.

Tea tree essential oil and its impact on blue mold, volatile compounds, and 
postharvest quality of 'Fuji' apples: A study of laboratory-extracted and 
commercial essential oils.

da Silva JC(1), Steffens CA(2), Alves JAV(2), Moreira MA(2), do Amarante CVT(2), 
Casa RT(3), Espíndola BP(4), Bortoluzzi AL(4).

Author information:
(1)Santa Catarina State University (UDESC), College of Agricultural and 
Veterinary Sciences (CAV), Department of Agronomy, Postharvest Physiology and 
Technology Laboratory, Lages, (SC), Brazil. Electronic address: 
janaiana2@hotmail.com.
(2)Santa Catarina State University (UDESC), College of Agricultural and 
Veterinary Sciences (CAV), Department of Agronomy, Postharvest Physiology and 
Technology Laboratory, Lages, (SC), Brazil.
(3)Santa Catarina State University (UDESC), College of Agricultural and 
Veterinary Sciences (CAV), Department of Agronomy, Phytopathology Laboratory, 
Lages, (SC), Brazil.
(4)Federal Institute of Santa Catarina (IFC), Department of Agronomy, Santa Rosa 
do Sul, (SC), Brazil.

This study evaluated the effects of tea tree essential oil (TTO) on blue mold 
severity, volatile compound profiles, and postharvest quality of 'Fuji' apples 
during cold storage. Two experiments were conducted using laboratory-extracted 
TTO from Brazil and commercial TTO from Australia, applied by vaporization at 
various concentrations. Both types of TTO affected major volatile compounds, 
including terpinen-4-ol, γ-terpinene, and α-terpinene. The laboratory-extracted 
TTO had higher of 1,8-cineole, while commercial TTO had more p-cymene. TTO 
reduced blue mold severity up to 115 μL L-1 (laboratory) and 99 μL L-1 
(commercial). Ethylene production decreased with laboratory-extracted TTO up to 
64 μL L-1, while commercial TTO decreased ethylene production. Laboratory TTO 
increased the respiratory up to 41 μL L-1 before declining, whereas commercial 
TTO continuously decreased the respiratory. Higher concentrations of laboratory 
TTO decreased flesh firmness and lightness.TTO types altered the apples' 
volatile profiles, reducing 'Fuji' apple aromas.

Copyright © 2024 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.foodchem.2024.141660
PMID: 39461311

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.