Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Plants (Basel). 2023 Sep 12;12(18):3244. doi: 10.3390/plants12183244.

Isolation of Volatile Compounds by Microwave-Assisted Extraction from Six 
Veronica Species and Testing of Their Antiproliferative and Apoptotic 
Activities.

Vrca I(1), Čikeš Čulić V(2), Lozić M(2), Dunkić N(3), Kremer D(4), Ruščić M(1), 
Nazlić M(1), Dunkić V(1).

Author information:
(1)Faculty of Science, University of Split, Ruđera Boškovića 33, 21000 Split, 
Croatia.
(2)School of Medicine, University of Split, Šoltanska 2, 21000 Split, Croatia.
(3)Practice of General Medicine, Antuna Gustava Matoša 2, 21000 Split, Croatia.
(4)Faculty of Pharmacy and Biochemistry, University of Zagreb, Ante Kovačića 1, 
10000 Zagreb, Croatia.

This study was conducted to determine the differences in the chemical 
composition of the essential oils and hydrosols of six different Veronica 
species (V. agrestis, V. anagalloides, V. austriaca ssp. jacquinii, V. 
beccabunga, Veronica cymbalaria, and V. officinalis) and to test their 
antiproliferative and apoptotic activities, according to the authors' knowledge, 
because of insufficient research and lack of information. Also, the goal was to 
determine which obtained samples were better in achieving antiproliferative and 
apoptotic activities and due to which volatile components. Therefore, essential 
oils (EOs) and hydrosols (HYs) were isolated from the above-mentioned Veronica 
species by microwave-assisted extraction (MAE). Phytochemical identification of 
the free volatile compounds was performed using a GC equipped with a flame 
ionization detector and a mass spectrometer. Their antiproliferative and 
apoptotic activities against two human cancer cell lines, breast cancer cell 
line MDA-MB-231 and bladder cancer cell line T24, were determined. The main 
compounds identified in the studied Veronica EOs and HYs were terpinen-4-ol 
(0.34-6.49%), linalool (0.34-6.61%), (E)-caryophyllene (0.97-7.55%), 
allo-aromadendrene (0.18-2.21%), caryophyllene oxide (1.42-23.83%), benzene 
acetaldehyde (0.26-13.34%), and β-ionone (1.08-16.53%). In general, HYs of the 
tested Veronica species showed higher antiproliferative activity (IC50 
13.41-42.05%) compared to EOs (IC50 158.1-970.4 µg/mL) on MDA-MB-231 and T24 
cancer cell lines after 48 and 72 h. V. agrestis EO showed the best apoptotic 
effect among the EOs on the MDA-MB-231 cancer cell line (10.47 ± 0.53% and 9.06 
± 0.74% of early/late apoptosis, compared with control 3.61 ± 0.62% and 0.80 ± 
0.17% of early/late apoptosis, respectively) and among the HYs V. cymbalaria 
showed 9.95 ± 1.05% and 3.06 ± 0.28% of early/late apoptosis and V. anagalloides 
8.29 ± 1.09% and 1.95 ± 0.36% of early/late apoptosis compared with control (for 
EO was 7.45 ± 1.01% and 0.54 ± 0.25%, and for HY was 4.91 ± 1.97% and 0.70 ± 
0.09% of early/late apoptosis, respectively) on the T24 cancer cell line. Future 
research will include other Croatian species of the genus Veronica to gain a 
more complete insight into the biological activity of the volatile products of 
this genus for potential discovery of drugs based on natural plant extracts.

DOI: 10.3390/plants12183244
PMCID: PMC10535125
PMID: 37765408

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


2. PLoS One. 2023 Aug 24;18(8):e0289991. doi: 10.1371/journal.pone.0289991. 
eCollection 2023.

Exploring the chemical composition, in vitro and in silico study of the 
anticandidal properties of annonaceae species essential oils from the Amazon.

Cascaes MM(1), Marques da Silva SH(2), de Oliveira MS(3)(4), Cruz JN(5), de 
Moraes ÂAB(5), do Nascimento LD(3), Ferreira OO(3), Guilhon GMSP(1), Andrade 
EHA(1)(3).

Author information:
(1)Programa de Pós-Graduação em Química, Universidade Federal do Pará, Belém, 
PA, Brazil.
(2)Seção de Bacteriologia e Micologia LabMicol-SABMI Laboratório de Micologia, 
Instituto Evandro Chagas-IEC/SVS/MS, Ananindeua, Brazil.
(3)Laboratório Adolpho Ducke, Coordenação de Botânica, Museu Paraense Emílio 
Goeldi, Belém, Brazil.
(4)Programa de Pós-Graduação em Ciências Biológicas-Botânica Tropical, 
Universidade Federal Rural da Amazônia and Museu Paraense Emílio Goeldi, Belém, 
PA, Brazil.
(5)Laboratory of Functional and Structural Biology, Institute of Biological 
Sciences, Universidade Federal do Pará, Belém, PA, Brazil.

Chemical composition of the essential oils (EOs) from the leaves of five 
Annonaceae species found in the amazon region was analyzed by Gas chromatography 
coupled to mass spectrometry. The antifungal activity of theses EOs was tested 
against Candida albicans, Candida auris, Candida famata, Candida krusei and 
Candida tropicalis. In addition, an in silico study of the molecular 
interactions was performed using molecular modeling approaches. Spathulenol 
(29.88%), α-pinene (15.73%), germacra-4(15),5,10(14)-trien-1-α-ol (6.65%), and 
caryophylene oxide (6.28%) where the major constitents from the EO of Anaxagorea 
dolichocarpa. The EO of Duguetia echinophora was characterized by 
β-phellanderene (24.55%), cryptone (12.43%), spathulenol (12.30%), and sabinene 
(7.54%). The major compounds of the EO of Guatteria scandens where β-pinene 
(46.71%), α-pinene (9.14%), bicyclogermacrene (9.33%), and E-caryophyllene 
(8.98%). The EO of Xylopia frutescens was characterized by α-pinene (40.12%) and 
β-pinene (36.46%). Spathulenol (13.8%), allo-aromadendrene epoxide (8.99%), 
thujopsan-2-α-ol (7.74%), and muurola-4,10(14)-dien-1-β-ol (7.14%) were the main 
chemical constituents reported in Xylopia emarginata EO. All EOs were active 
against the strains tested and the lowest inhibitory concentrations were 
observed for the EOs of D. echinophora, X. emarginata, and X. frutescens against 
C. famata the Minimum Inhibitory Concentration values of 0.07, 0.019 and 0.62 
μL.mL-1, respectively. The fungicidal action was based on results of minimum 
fungicidal concentration and showed that the EOs showed fungicide activity 
against C. tropicalis (2.5 μL.mL-1), C. krusei (2.5 μL.mL-1) and C. auris (5 
μL.mL-1), respectively. The computer simulation results indicated that the major 
compounds of the EOs can interact with molecular targets of Candida spp.

Copyright: © 2023 Cascaes 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.0289991
PMCID: PMC10449155
PMID: 37616214 [Indexed for MEDLINE]

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


3. Nat Prod Res. 2023 Nov-Dec;37(23):4042-4048. doi:
10.1080/14786419.2022.2164578.  Epub 2023 Jan 17.

Chemical composition and antioxidant activity of the essential oil of Renealmia 
alpinia (Rottb.) Maas.

de Souza ECA(1), Flach A(1), da Costa LAMA(1).

Author information:
(1)Department of Chemistry, Biotechnology Laboratory and Fine Chemicals, Federal 
University of Roraima, Aeroporto, RR, Brazil.

Renealmia alpinia (Rottb.) Maas was collected in Serra do Tepequém, municipality 
of Amajari, state of Roraima, Brazil. The essential oil was obtained from the 
fresh leaves by hydrodistillation using a Clevenger apparatus and analysed using 
GC-FID and GC-MS. The oil provided a yield of 0.6% (w/w), which, in the analysis 
of its contents, presented a higher concentration of sesquiterpenes, with 
α-phellandrene (23.10%), 16-oxo-8(17),12(E)-labdadien-15-oic acid (17.05%), 
β-caryophyllene (10.28%), valencene (5.27%) and allo-aromadendrene (3.52%) being 
the most abundant. The antioxidant activity of the essential oil was determined 
using two methods, and indicated significant activity by both. Using the DPPH 
method, the essential oil presented an IC50 of 1.470 ± 0.0264 mg.L1 and an 
inhibition of the β-carotene/linoleic acid oxidation system of 76.43 ± 0.80%.

DOI: 10.1080/14786419.2022.2164578
PMID: 36650708 [Indexed for MEDLINE]


4. Phytochemistry. 2023 Jan;205:113508. doi: 10.1016/j.phytochem.2022.113508.
Epub  2022 Nov 10.

Multivariate analysis of chemical and genetic diversity of wild Humulus lupulus 
L. (hop) collected in situ in northern France.

Paguet AS(1), Siah A(1), Lefèvre G(1), Moureu S(1), Cadalen T(1), Samaillie 
J(1), Michels F(1), Deracinois B(1), Flahaut C(1), Alves Dos Santos H(1), 
Etienne-Debaecker A(1), Rambaud C(1), Chollet S(1), Molinié R(1), Fontaine 
JX(1), Waterlot C(2), Fauconnier ML(1), Sahpaz S(1), Rivière C(3).

Author information:
(1)Joint Research Unit 1158 BioEcoAgro, Univ. Lille, JUNIA, UPJV, Univ. Liège, 
INRAE, Univ. Artois, Univ. Littoral Côte D'Opale, ICV-Institut Charles 
Viollette, F-59650 Villeneuve D'Ascq, France.
(2)Univ. Lille, Institut Mines-Télécom, Univ. Artois, JUNIA, ULR 4515 - LGCgE, 
Laboratoire de Génie Civil et Géo-Environnement, F-59000 Lille, France.
(3)Joint Research Unit 1158 BioEcoAgro, Univ. Lille, JUNIA, UPJV, Univ. Liège, 
INRAE, Univ. Artois, Univ. Littoral Côte D'Opale, ICV-Institut Charles 
Viollette, F-59650 Villeneuve D'Ascq, France. Electronic address: 
celine.riviere@univ-lille.fr.

The hop plant (Humulus lupulus L.) has been exploited for a long time for both 
its brewing and medicinal uses, due in particular to its specific chemical 
composition. These last years, hop cultivation that was in decline has been 
experiencing a renewal for several reasons, such as a craze for strongly hopped 
aromatic beers. In this context, the present work aims at investigating the 
genetic and chemical diversity of fifty wild hops collected from different 
locations in Northern France. These wild hops were compared to ten commercial 
varieties and three heirloom varieties cultivated in the same sampled 
geographical area. Genetic analysis relying on genome fingerprinting using 11 
microsatellite markers showed a high level of diversity. A total of 56 alleles 
were determined with an average of 10.9 alleles per locus and assessed a 
significant population structure (mean pairwise FST = 0.29). Phytochemical 
characterization of hops was based on volatile compound analysis by HS-SPME 
GC-MS, quantification of the main prenylated phenolic compounds by UHPLC-UV as 
well as untargeted metabolomics by UHPLC-HRMS and revealed a high level of 
chemical diversity among the assessed wild accessions. In particular, analysis 
of volatile compounds revealed the presence of some minor but original 
compounds, such as aromadendrene, allo-aromadendrene, isoledene, β-guaiene, 
α-ylangene and β-pinene in some wild accessions; while analysis of phenolic 
compounds showed high content of β-acids in these wild accessions, up to 2.37% 
of colupulone. Genetic diversity of wild hops previously observed was hence 
supported by their chemical diversity. Sample soil analysis was also performed 
to get a pedological classification of these different collection sites. Results 
of the multivariate statistical analysis suggest that wild hops constitute a 
huge pool of chemical and genetic diversity of this species.

Copyright © 2022 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.phytochem.2022.113508
PMID: 36370882 [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.


5. Antioxidants (Basel). 2022 Aug 30;11(9):1709. doi: 10.3390/antiox11091709.

Phytochemical Profile, Antioxidant Potential and Toxicity Evaluation of the 
Essential Oils from Duguetia and Xylopia Species (Annonaceae) from the Brazilian 
Amazon.

Cascaes MM(1), De Moraes ÂAB(2), Cruz JN(3), Franco CJP(2), E Silva RC(1), 
Nascimento LDD(2), Ferreira OO(4), Anjos TOD(5), de Oliveira MS(2), Guilhon 
GMSP(1), Andrade EHA(1)(2)(4).

Author information:
(1)Programa de Pós-Graduação em Química, Universidade Federal do Pará, Rua 
Augusto Corrêa S/N, Guamá, Belém 66075-900, PA, Brazil.
(2)Laboratório Adolpho Ducke-Coordenação de Botânica, Museu Paraense Emílio 
Goeldi, Av. Perimetral, 1901, Terra Firme, Belém 66077-830, PA, Brazil.
(3)Laboratory of Functional and Structural Biology, Institute of Biological 
Sciences, Universidade Federal do Pará, Rua Augusto Corrêa S/N, Guamá, Belém 
66075-900, PA, Brazil.
(4)Programa de Pós-Graduação em Biodiversidade e Biotecnologia-Rede Bionorte, 
Universidade Federal do Pará, Rua Augusto Corrêa S/N, Guamá, Belém 66075-900, 
PA, Brazil.
(5)Programa de Pós-Graduação em Ciências Biológicas-Botânica Tropical, Museu 
Paraense Emilio Goeldi/Universidade Federal Rural da Amazônia, Av. Perimetral, 
1901, Terra Firme, Belém 66077-830, PA, Brazil.

The essential oils (EOs) of Duguetia echinophora, D. riparia, Xylopia emarginata 
and X. frutescens (Annonaceae) were obtained by hydrodistillation and the 
chemical composition was analyzed by GC-MS. An antioxidant assay using the ABTS 
and DPPH radicals scavenging method and cytotoxic assays against Artemia salina 
were also performed. We evaluated the interaction of the major compounds of the 
most toxic EO (X. emarginata) with the binding pocket of the enzyme 
Acetylcholinesterase, a molecular target related to toxicity in models of 
Artemia salina. The chemical composition of the EO of D. echinophora was 
characterized by β-phellandrene (39.12%), sabinene (17.08%) and terpinolene 
(11.17%). Spathulenol (22.22%), caryophyllene oxide (12.21%), humulene epoxide 
II (11.86%) and allo-aromadendrene epoxide (10.20%) were the major constituents 
of the EO from D. riparia. Spathulenol (5.65%) and caryophyllene oxide (5.63%) 
were the major compounds of the EO from X. emarginata. The EO of X. frutescens 
was characterized by α-pinene (20.84%) and byciclogermacrene (7.85%). The 
results of the radical scavenger DPPH assays ranged from 15.87 to 69.38% and the 
highest percentage of inhibition was observed for the EO of X. emarginata, while 
for ABTS radical scavenging, the antioxidant capacity of EOs varied from 14.61 
to 63.67%, and the highest percentage of inhibition was observed for the EO of 
X. frutescens. The EOs obtained from D. echinophora, X. emarginata and X. 
frutescens showed high toxicity, while the EO of D. riparia was non-toxic. 
Because the EO of X. emarginata is the most toxic, we evaluated how its major 
constituents were able to interact with the Acetylcholinesterase enzyme. The 
docking results show that the compounds are able to bind to the binding pocket 
through non-covalent interactions with the residues of the binding pocket. The 
species X. emarginata and X. frutescens are the most promising sources of 
antioxidant compounds; in addition, the results obtained for preliminary 
cytotoxicity of the EOs of these species may also indicate a potential 
biological activity.

DOI: 10.3390/antiox11091709
PMCID: PMC9495368
PMID: 36139777

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