Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. PLoS One. 2024 Feb 8;19(2):e0294126. doi: 10.1371/journal.pone.0294126. 
eCollection 2024.

Chemical profile of Juniperus excelsa M. Bieb. essential oil within and between 
populations and its weed seed suppression effect.

Semerdjieva I(1)(2), Zheljazkov VD(3), Dincheva I(4), Radoukova T(5), Astatkie 
T(6), Maneva V(7), Atanasova D(7), Fidan H(8), Stankov S(8), Stoyanova A(9).

Author information:
(1)Department of Botany and Agrometeorology, Agricultural University, Mendeleev, 
Plovdiv, Bulgaria.
(2)Department of Plant and Fungal Diversity and Resources, Institute of 
Biodiversity and Ecosystem Research, Bulgarian Academy of Sciences, Sofia, 
Bulgaria.
(3)Department of Crop and Soil Science, Oregon State University, Corvallis, 
Oregon, United States of America.
(4)Plant Genetic Research Group, AgroBioInstitute, Agricultural Academy, Sofia, 
Bulgaria.
(5)Department of Botany and Biological Education, University of Plovdiv Paisii 
Hilendarski, Plovdiv, Bulgaria.
(6)Faculty of Agriculture, Dalhousie University, Truro, Canada.
(7)Plant Protection and Technology Department, Institute of Agriculture, 
Karnobat, Agricultural Academy, Karnobat, Bulgaria.
(8)Department of Tourism and Culinary Management, Faculty of Economics, 
University of Food Technologies, Plovdiv, Bulgaria.
(9)Department of Technology of Tobacco, Sugar, Vegetable and Essential Oils, 
University of Food Technologies, Maritza, Plovdiv, Bulgaria.

The aims of this study were to (1) establish the intrapopulation and seasonal 
variation of Juniperus excelsа essential oil (EO); (2) compare the J. excelsa 
concrete and resinoid composition with its EO composition; and (3) investigate 
the potential herbicidal activity of J. excelsa EO against seeds of Papaver 
rhoeas L., Consolida orientalis (J.Gay) Schrödinger, Anthemis arvensis L., Avena 
fatua L., and Agrostemma githago L. Four independent studies were performed to 
meet these objectives. Twenty-eight individual trees were analyzed from two 
populations to establish intrapopulation and interpopulation variability of EOs 
yield and composition. In the seasonal dynamic study of leaf EO, samples from 
the same three trees and in the same population were collected in January, 
March, May, July, October, and December and their EO yield and composition 
determined. The EOs (intrapopulation and seasonal) were extracted by 
hydrodistillation, while the EO for the herbicidal test was obtained by steam 
distillation in a semi-commercial (SCom) apparatus. Overall, the EO yield varied 
significantly from 0.93% to 2.57%. α-Pinene (8.85-35.94%), limonene 
(11.81-50.08%), and cedrol (3.41-34.29%) were the predominant EO compounds in 
all samples (intrapopulation variability); however, trans-2,4-decadienol and 
β-caryophyllene were predominant in some individual trees. Four chemical groups 
were identified in the samples collected from two natural populations 
(intrapopulation). This is the first report on the compositions of J. excelsa 
concrete and resinoid. Cedrol (15.39%), 7-hydroxy-4-methyl-coumarin (17.63%), 
1-octacosanol (36.85%), tritriacontane (16.08%), and tiacontanoic acid were the 
main compounds in the concrete and resinoid. Juniperus excelsa EO suppressed 
seed germination and seedling growth of P. rhoeas, C. orientalis, A. arvensis, 
A. fatua, and A. githago, demonstrating its potential to be used for the 
development of new biopesticides. The highest EO yield with high content of 
limonene and cedrol was obtained from samples harvested during the winter months 
(December, January, and March).

Copyright: © 2024 Semerdjieva et al. This is an open access article distributed 
under the terms of the Creative Commons Attribution License, which permits 
unrestricted use, distribution, and reproduction in any medium, provided the 
original author and source are credited.

DOI: 10.1371/journal.pone.0294126
PMCID: PMC10852245
PMID: 38330006 [Indexed for MEDLINE]

Conflict of interest statement: The authors have declared that no competing 
interests exist.


2. Molecules. 2023 Feb 8;28(4):1628. doi: 10.3390/molecules28041628.

GC/MS Analysis, Cytotoxicity, and Antiviral Activities of Annona glabra Hexane 
Extract Supported by In Silico Study.

Soleman DM(1), Eldahshan OA(2)(3), Ibrahim MH(4), Ogaly HA(5)(6), Galal 
HM(7)(8), Batiha GE(9), Elkousy RH(10).

Author information:
(1)Department of Pharmacognosy, Faculty of Pharmacy, Misr International 
University, Cairo P.O. Box 41611, Egypt.
(2)Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, Cairo 
11566, Egypt.
(3)Center for Drug Discovery Research and Development, Faculty of Pharmacy, Ain 
Shams University, Cairo 11566, Egypt.
(4)Department of Pharmaceutical Medicinal Chemistry and Drug Design, Faculty of 
Pharmacy (for Girls), Al-Azhar University, Nasr City, Cairo 11651, Egypt.
(5)Chemistry Department, College of Science, King Khalid University, Abha 61421, 
Saudi Arabia.
(6)Biochemistry and Molecular Biology Department, Faculty of Veterinary 
Medicine, Cairo University, Giza 12211, Egypt.
(7)Department of Medical Physiology, College of Medicine, Jouf University, 
Sakaka 72388, Saudi Arabia.
(8)Department of Medical Physiology, Faculty of Medicine, Assiut University, 
Assiut 71515, Egypt.
(9)Department of Pharmacology and Therapeutics, Faculty of Veterinary Medicine, 
Damanhour University, Damanhour 22511, Egypt.
(10)Department of Pharmacognosy, Faculty of Pharmacy (for Girls), Al-Azhar 
University, Nasr City, Cairo 11651, Egypt.

Annona glabra Linn is employed in conventional medicine to treat a number of 
human disorders, including cancer and viruses. In the present investigation, the 
significant phytochemical components of Annona glabra hexane extract were 
identified using gas chromatography-mass spectrometry (GC-MS) analysis. Three 
major compounds were identified in the hexane extract: tritriacontane (30.23%), 
13, 17-dimethyl-tritriacontane (22.44%), and limonene (18.97%). MTT assay was 
used to assess the cytotoxicity of the extract on six human cancer cell lines 
including liver (HepG-2), pancreas (PANC-1), lung (A-549), breast (MCF-7, 
HTB-22), prostate (PC-3), and colon (CACO-2, ATB-37). The extract exhibited 
significant cytotoxic activity against both CACO-2 and A-549 cancer cell lines 
(IC50 = 47 ± 0.74 μg/mL and 56.82 ± 0.92 μg/mL) in comparison with doxorubicin 
(IC50 = 31.91 ± 0.81 μg/mL and 23.39 ± 0.43 μg/mL) and of SI of 3.8 and 3.1, 
respectively. It also induced moderate-to-weak activities against the other 
cancerous cell lines: PC-3, PANC-1, MCF-7, and HepG-2 (IC50 = 81.86 ± 3.26, 
57.34 ± 0.77, 80.31 ± 4.13, and 57.01 ± 0.85 μg/mL) in comparison to doxorubicin 
(IC50 = 32.9 ± 1.74, 19.07 ± 0.2, 15.48 ± 0.84 and 5.4 ± 0.22 μg/mL, 
respectively) and SI of 2.2, 3.1, 2.2, and 3.1, respectively. In vitro anti-HSV1 
(Herpes simplex 1 virus) and HAV (Hepatitis A virus) activity was evaluated 
using MTT colorimetric assay with three different protocols to test protective, 
anti-replicative, and anti-infective antiviral activities, and three separate 
replications of each experiment were conducted. The plant extract showed 
promising protective and virucidal activity against HSV1 with no significant 
difference with acyclovir (79.55 ± 1.67 vs. 68.44 ± 7.62 and 70.91 ± 7.02 vs. 
83.76 ± 5.67), while it showed mild protective antiviral activity against HAV 
(48.08 ±3.46) with no significant difference vs. acyclovir (36.89 ± 6.61). The 
selected main compounds were examined for their bioactivity through in silico 
molecular docking, which exhibited that limonene could possess the strongest 
antiviral properties. These findings support Annona glabra's conventional use, 
which is an effective source of antiviral and anticancer substances that could 
be used in pharmaceuticals.

DOI: 10.3390/molecules28041628
PMCID: PMC9966597
PMID: 36838616 [Indexed for MEDLINE]

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


3. Foods. 2021 Feb 1;10(2):290. doi: 10.3390/foods10020290.

n-Alkanes and n-Alkenes in Virgin Olive Oil from Calabria (South Italy): The 
Effects of Cultivar and Harvest Date.

Giuffrè AM(1).

Author information:
(1)Dipartimento di Agricoltura, Università degli Studi Mediterranea di Reggio 
Calabria, Contrada Melissari, 89124 Reggio Calabria, Italy.

n-Alkanes and n-alkenes are components of the unsaponifiable fraction of an 
olive oil. These were analysed by GC on-column analysis and are here proposed as 
an additional tool to certify the origin, authenticity, traceability and 
chemical quality of olive oil produced in the Reggio Calabria province (South 
Italy). Nine cultivars were studied: Cassanese, Coratina, Itrana, Leccino, 
Nociara, Ottobratica, Pendolino, Picholine and Sinopolese grown in the region of 
Calabria (South Italy). n-Alkanes in the range from 21 to 35 chain carbon atoms 
and alkenes in the range from 23:1 to 25:1 chain carbon atoms were found with 
the following elution order: heneicosane (C21), docosane (C22), tricosene 
(C23:1), tricosane (C23), tetracosene (C24:1), tetracosane (C24), pentacosene 
(C25:1), pentacosane (C25), hexacosane (C26), eptacosane (C27), octacosane 
(C28), nonacosane (C29), triacontane (C30), entriacontane (C31), dotriacontane 
(C32), tritriacontane (C33), tetratriacontane (C34), pentatriacontane (C35). The 
oil of all cultivars showed a decreasing trend in total n-alkane and n-alkene 
content, with the oil of Sinopolese showing the highest content, varying from 
328.50 to 214.00 mg/kg. Odd-chain alkanes predominated over even-chain 
n-alkanes, and tricosane, tetracosane and pentacosane were the most represented 
alkanes. Cultivar and harvest date significantly influenced the n-alkane and 
n-alkene content. These findings can be useful to distinguish different olive 
cultivars and to decide the fruit harvest date for the oil of the Reggio 
Calabria province (South Italy). A daily quantity of 30 g of olive oil of the 
Sinoplese cv (the one with the highest n-alkane and n-alkene content) was found 
to be in accordance with the suggestions of the European Agency for the 
evaluation of medicinal products Committee for veterinary medicinal products and 
biogenic hydrocarbons intake for the human diet.

DOI: 10.3390/foods10020290
PMCID: PMC7912712
PMID: 33535538

Conflict of interest statement: The author declares no conflict of interest.


4. PLoS One. 2020 Nov 4;15(11):e0241666. doi: 10.1371/journal.pone.0241666. 
eCollection 2020.

Sub-lethal effects of the consumption of Eupatorium buniifolium essential oil in 
honeybees.

Rossini C(1), Rodrigo F(1), Davyt B(1)(2), Umpiérrez ML(1)(2), González A(1), 
Garrido PM(2), Cuniolo A(2), Porrini LP(2), Eguaras MJ(2), Porrini MP(1)(2).

Author information:
(1)Laboratorio de Ecología Química, Facultad de Química, Universidad de la 
República de Uruguay, Montevideo, Uruguay.
(2)Centro de Investigación en Abejas Sociales (CIAS), Instituto de 
Investigaciones en Producción Sanidad y Ambiente (IIPROSAM), Facultad de 
Ciencias Exactas y Naturales, Universidad Nacional de Mar del Plata, Mar del 
Plata, Buenos Aires, Argentina.

When developing new products to be used in honeybee colonies, further than acute 
toxicity, it is imperative to perform an assessment of risks, including various 
sublethal effects. The long-term sublethal effects of xenobiotics on honeybees, 
more specifically of acaricides used in honeybee hives, have been scarcely 
studied, particularly so in the case of essential oils and their components. In 
this work, chronic effects of the ingestion of Eupatorium buniifolium 
(Asteraceae) essential oil were studied on nurse honeybees using laboratory 
assays. Survival, food consumption, and the effect on the composition of 
cuticular hydrocarbons (CHC) were assessed. CHC were chosen due to their key 
role as pheromones involved in honeybee social recognition. While food 
consumption and survival were not affected by the consumption of the essential 
oil, CHC amounts and profiles showed dose-dependent changes. All groups of CHC 
(linear and branched alkanes, alkenes and alkadienes) were altered when 
honeybees were fed with the highest essential oil dose tested (6000 ppm). The 
compounds that significantly varied include n-docosane, n-tricosane, 
n-tetracosane, n-triacontane, n-tritriacontane, 9-tricosene, 7-pentacosene, 
9-pentacosene, 9-heptacosene, tritriacontene, pentacosadiene, hentriacontadiene, 
tritriacontadiene and all methyl alkanes. All of them but pentacosadiene were 
up-regulated. On the other hand, CHC profiles were similar in healthy and 
Nosema-infected honeybees when diets included the essential oil at 300 and 3000 
ppm. Our results show that the ingestion of an essential oil can impact CHC and 
that the effect is dose-dependent. Changes in CHC could affect the signaling 
process mediated by these pheromonal compounds. To our knowledge this is the 
first report of changes in honeybee cuticular hydrocarbons as a result of 
essential oil ingestion.

DOI: 10.1371/journal.pone.0241666
PMCID: PMC7641371
PMID: 33147299 [Indexed for MEDLINE]

Conflict of interest statement: The authors have declared that no competing 
interests exist.


5. J Forensic Sci. 2021 Jan;66(1):236-244. doi: 10.1111/1556-4029.14572. Epub
2020  Sep 23.

Cuticular hydrocarbons as a tool for determining the age of Chrysomya rufifacies 
(Diptera: Calliphoridae) larvae.

Sharma A(1), Drijfhout FP(2), Tomberlin JK(3), Bala M(1).

Author information:
(1)Department of Zoology and Environmental Sciences, Punjabi University, 
Patiala, India.
(2)Department of Chemistry, Keele University, Keele, UK.
(3)Department of Entomology, Texas A&M University, College Station, TX, USA.

Calliphoridae are one of the most important insect groups encountered as 
evidence collected from a crime scene. Age determination of the immature stages 
of these necrophagous flies is an important step toward estimating the time of 
colonization and inferring a minimum postmortem interval (PMImin ) in most 
instances. To determine if the cuticular hydrocarbons could be used to establish 
whether the development stages yield characteristics profiles, allowing for age 
estimation, hydrocarbons were extracted from 1st and 2nd, as well as feeding and 
post-feeding 3rd instar Chrysomya rufifacies, the hairy maggot blow fly. 
Extracted hydrocarbons were analyzed using gas chromatography coupled to mass 
spectrometry with the aim to investigate the changes in chemical profiles of 
each larval stage. A total of 23 compounds were identified with most of them 
being alkanes (65%) with carbon chain lengths of 9-33 carbons, alkenes (18%), 
and methyl-branched alkanes (17%). All the hydrocarbons except pentadecane 
(C15), hexadecane (C16), and nonacosane (C29) showed significant differences in 
their expression throughout larval development. For 1st instars, nonane was the 
most abundant (17% of the total hydrocarbons content) compound. Accounting for 
11% and 10% of the cuticular hydrocarbons, tricosane and pentacosane, 
respectively, were the notable hydrocarbons in 2nd instars. For post-feeding 3rd 
instars, hentriacontane and tritriacontane were present with relative abundances 
18% and 15%, respectively. On average, there was a shift from low to high 
molecular weight hydrocarbons as the larvae aged. These results indicate the 
change in hydrocarbons makeup as larvae age and could potentially be used to 
determine the age of immature C. rufifacies and hence aid in PMImin estimations. 
However, future research is needed to validate these results under natural 
conditions in the field.

© 2020 American Academy of Forensic Sciences.

DOI: 10.1111/1556-4029.14572
PMID: 32966626 [Indexed for MEDLINE]