Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. J Agric Food Chem. 2024 Nov 6;72(44):24711-24723. doi:
10.1021/acs.jafc.4c06652.  Epub 2024 Oct 29.

Scent Knows Better: Utilizing Volatile Organic Compounds as a Robust Tool for 
Identifying Higher Cannabidiol- and Tetrahydrocannabinol-Containing Cannabis 
Cultivars in Field Conditions.

Cho JY(1), Ryu DH(1), Hamayun M(1)(2), Lee SH(3), Jung JH(4), Kim HY(1)(5).

Author information:
(1)Smart Farm Research Center, Korea Institute of Science and Technology (KIST), 
Gangneung, Gangwon 25451, Republic of Korea.
(2)Department of Botany, Garden Campus, Abdul Wali Khan University Mardan, 
Nowshera Mardan Rd, Mardan 23200, Pakistan.
(3)Department of southern area crop science, National institute of crop science, 
Rural development administration, Miryang, Gyeongnam 50424, Republic of Korea.
(4)Division of Biotechnology, College of Life Sciences & Biotechnology, Korea 
University, Seoul 02841, Republic of Korea.
(5)Natural Product Applied Science, KIST school, University of Science and 
Technology (UST), Gangneung, Gangwon 25451, Republic of Korea.

The primary cannabinoids cannabidiol (CBD) and tetrahydrocannabinol (THC), found 
in cannabis, are known to originate from genetic diversity, resulting in 
distinct characteristics. This study aimed to identify VOC markers to 
distinguish between higher CBD and THC cannabis cultivars under field 
conditions. Among the 58 VOCs, β-caryophyllene and α-humulene were primary VOCs 
across all cannabis cultivars. Intriguingly, certain terpene VOCs exhibited 
contrasting trends between higher CBD and higher THC cannabis cultivars. 
Eudesma-3,7(11)-diene and α-guaiol consistently appeared as highlighted 
compounds, suggesting their potential to distinguish between higher CBD and THC 
cannabis cultivars. ROC curve analysis revealed approximately 94% predictive 
accuracy for these putative markers. Given the current focus on VOCs as sensor 
markers for plant health, growth, and quality, the identified VOC 
markers─applicable across varieties and growth stages─could enable 
nondestructive, rapid, and accurate identification of CBD- and THC-rich cannabis 
species in field conditions.

DOI: 10.1021/acs.jafc.4c06652
PMID: 39468951 [Indexed for MEDLINE]


2. J Econ Entomol. 2024 Oct 22:toae232. doi: 10.1093/jee/toae232. Online ahead of
 print.

Behavioral responses of Araecerus fasciculatus (Coleoptera: Anthribidae) to 
volatiles of selected stored Chinese medicinal plant products.

Zeng G(1), Xie S(2), Jian L(2), Agrafioti P(3), Wu K(1), Athanassiou CG(3), Cao 
Y(2).

Author information:
(1)Department of Resources and Environment, Moutai Institute, Renhuai, Guizhou, 
People's Republic of China.
(2)Guizhou Provincial Key Laboratory for Rare Animal and Economic Insect of the 
Mountainous Region, Key Laboratory of Surveillance and Management for Alien 
Invasive Species in Guizhou Province, Department of Biology and Engineering of 
Environment, Guiyang University, Guiyang, People's Republic of China.
(3)Laboratory of Entomology and Agricultural Zoology, Department of Agriculture, 
Crop Production and Rural Environment, University of Thessaly, Volos, Greece.

The olfactory responses of Araecerus fasciculatus Degeer to the volatiles of 5 
traditional Chinese medicine plant products (CMPPs; i.e., Codonopsis pilosula 
Franch., Ophiopogon japonicus Linn. f., Astragalus membranaceus Fisch., 
Dendrobium nobile Lindl., and Angelica dahurica Fisch.) were studied using 
Y-tube, 4-arm, and 6-arm olfactometers. The volatile components of these CMPPs 
were analyzed using gas chromatography-mass spectrometry (GC-MS). A. 
fasciculatus significantly preferred the CMPPs volatiles in the order of O. 
japonicus > C. pilosula > A. membranaceus ≥ D. nobile = A. dahurica. In the 
volatile profiles of O. japonicus, C. pilosula, A. membranaceus, D. nobile, and 
A. dahurica, GC-MS identified 27, 61, 63, 52, and 71 components, respectively, 
and β-elemene (30.58%), hexanal (12.69%), selina-3,7(11)-diene (12.31%), 
d-limonene (18.59%), and α-curcumene (8.88%) were the most abundant volatile 
components. A. fasciculatus were attracted to β-elemene, α-selinene, and 
β-selinene (main components of the volatile profiles of the most preferred CMPPs 
of O. japonicus) at different concentrations, with 1, 50, and 25 µg/µl being the 
most attractive, respectively. The olfactory preferences of A. fasciculatus were 
β-elemene > α-selinene = β-selinene based on the 4-arm olfactometer bioassays 
for comparisons at their most attractive concentrations. Therefore, differences 
in the volatile profiles among CMPPs significantly influenced the olfactory 
responses of A. fasciculatus, offering insight into the mechanisms of host 
preferences in stored-product pests based on chemical ecology. β-elemene showed 
the greatest potential to be developed as an attractant for the monitoring and 
control of this pest.

© The Author(s) 2024. Published by Oxford University Press on behalf of 
Entomological Society of America. All rights reserved. For commercial re-use, 
please contact reprints@oup.com for reprints and translation rights for 
reprints. All other permissions can be obtained through our RightsLink service 
via the Permissions link on the article page on our site—for further information 
please contact journals.permissions@oup.com.

DOI: 10.1093/jee/toae232
PMID: 39436755


3. ACS Catal. 2024 Jul 9;14(14):11034-11043. doi: 10.1021/acscatal.4c02032. 
eCollection 2024 Jul 19.

Simulation-Guided Engineering Enables a Functional Switch in Selinadiene 
Synthase toward Hydroxylation.

Srivastava PL(1), Johns ST(2), Voice A(2), Morley K(2), Escorcia AM(2), Miller 
DJ(1), Allemann RK(1), van der Kamp MW(2).

Author information:
(1)School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff 
CF10 3AT, U.K.
(2)School of Biochemistry, University of Bristol, University Walk, Bristol BS8 
1TD, U.K.

Engineering sesquiterpene synthases to form predefined alternative products is a 
major challenge due to their diversity in cyclization mechanisms and our limited 
understanding of how amino acid changes affect the steering of these mechanisms. 
Here, we use a combination of atomistic simulation and site-directed mutagenesis 
to engineer a selina-4(15),7(11)-diene synthase (SdS) such that its final 
reactive carbocation is quenched by trapped active site water, resulting in the 
formation of a complex hydroxylated sesquiterpene (selin-7(11)-en-4-ol). 
Initially, the SdS G305E variant produced 20% selin-7(11)-en-4-ol. As suggested 
by modeling of the enzyme-carbocation complex, selin-7(11)-en-4-ol production 
could be further improved by varying the pH, resulting in selin-7(11)-en-4-ol 
becoming the major product (48%) at pH 6.0. We incorporated the SdS G305E 
variant along with genes from the mevalonate pathway into bacterial BL21(DE3) 
cells and demonstrated the production of selin-7(11)-en-4-ol at a scale of 10 
mg/L in batch fermentation. These results highlight opportunities for the 
simulation-guided engineering of terpene synthases to produce predefined complex 
hydroxylated sesquiterpenes.

© 2024 The Authors. Published by American Chemical Society.

DOI: 10.1021/acscatal.4c02032
PMCID: PMC11264211
PMID: 39050902

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


4. RETRACTED ARTICLE

Biomed Res Int. 2023 Apr 19;2023:9337763. doi: 10.1155/2023/9337763. eCollection 
2023.

Evaluation of the Anticancer Potential of Morus nigra and Ocimum basilicum 
Mixture against Different Cancer Cell Lines: An In Vitro Evaluation.

Almutairi BO(1), Alsayadi AI(1), Abutaha N(1), Al-Mekhlafi FA(1), Wadaan MA(1).

Author information:
(1)Department of Zoology, College of Science, King Saud University, P.O. Box 
2455 Riyadh 11451, Saudi Arabia.

Retraction in
    Biomed Res Int. 2024 Jan 9;2024:9847989. doi: 10.1155/2024/9847989.

Morus nigra (M) and Ocimum basilicum (O) mixture (MO2) extract was extracted 
using hexane (MO2H), chloroform (MO2C), ethyl acetate (MO2E), and methanol 
(MO2M) in a Soxhlet apparatus. The cytotoxicity was evaluated using MTT 
(3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide) assay. The IC50 
values of the MO2C-treated cancer cells were 11.31 μg/mL (MDA-MB-231), 
15.45 μg/mL (MCF-7), 18.9 μg/mL (HepG2), 26.33 μg/mL (Huh-7), 30.17 μg/mL 
(LoVo), and 36.76 μg/mL (HCT116). MO2C-treated cells showed cellular and nuclear 
morphological alterations like chromatin condensation and formation of apoptotic 
bodies as observed using light and fluorescent microscopy. The antioxidant and 
anti-inflammatory properties were investigated in vitro using 
2,2'-diphenyl-1-picrylhydrazyl (DPPH) and egg albumin denaturation assays. It 
was evident that the MO2M extract exhibited the highest antioxidant activity 
(18.13%), followed by the MO2E extract (12.25%), MO2C extract (9.380%), and MO2H 
extract (6.31%). The highest inhibition percentage of albumin denaturation was 
observed in MO2H (28.54%), followed by MO2M (4.32%) at 0.2 and 0.1 mg/mL 
concentrations, respectively. The compounds identified using gas 
chromatography-mass spectrometry (GC-MS) analysis for MO2C extract were 
α-trans-bergamotene, germacrene D, selin-4,7(11)-diene, 2 tridecen-1-ol, and 
2-decen-1-ol. The present study reveals that MO2C has promising anticancer 
activity and may serve as a potent polyherbal extract in cancer treatment.

Copyright © 2023 Bader O. Almutairi et al.

DOI: 10.1155/2023/9337763
PMCID: PMC10132895
PMID: 37124934 [Indexed for MEDLINE]

Conflict of interest statement: The authors have declared that they have no 
conflicts of interest.


5. Sci Rep. 2023 Apr 24;13(1):6644. doi: 10.1038/s41598-023-33390-x.

Mode of action, chemistry and defensive efficacy of the osmeterium in the 
caterpillar Battus polydamas archidamas.

Palma-Onetto V(1), Bergmann J(2), González-Teuber M(3)(4).

Author information:
(1)Departamento de Química Ambiental, Facultad de Ciencias, Universidad Católica 
de La Santísima Concepción, Concepción, Chile. vpalma@ucsc.cl.
(2)Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica 
de Valparaíso, Valparaíso, Chile.
(3)Departamento de Química Ambiental, Facultad de Ciencias, Universidad Católica 
de La Santísima Concepción, Concepción, Chile. mgonzalezt@bio.puc.cl.
(4)Departamento de Genética Molecular y Microbiología, Facultad de Ciencias 
Biológicas, Pontificia Universidad Católica de Chile, Santiago, Chile. 
mgonzalezt@bio.puc.cl.

Erratum in
    Sci Rep. 2024 Apr 16;14(1):8791. doi: 10.1038/s41598-024-59540-3.

Chemical secretions are one of the main defensive mechanisms in insects. The 
osmeterium is a unique organ in larvae of Papilionidae (Lepidoptera), which is 
everted upon disturbance, secreting odoriferous volatiles. Here, using larvae of 
the specialized butterfly Battus polydamas archidamas (Papilionidae: Troidini), 
we aimed to understand the mode of action of the osmeterium, the chemical 
composition and origin of the secretion, as well as its defensive efficiency 
against a natural predator. We described osmeterium's morphology, 
ultramorphology, structure, ultrastructure, and chemistry. Additionally, 
behavioral assays of the osmeterial secretion against a predator were developed. 
We showed that the osmeterium is composed of tubular arms (made up by epidermal 
cells) and of two ellipsoid glands, which possess a secretory function. The 
eversion and retraction of the osmeterium are dependent on the internal pressure 
generated by the hemolymph, and by longitudinal muscles that connect the abdomen 
with the apex of the osmeterium. Germacrene A was the main compound present in 
the secretion. Minor monoterpenes (sabinene and ß-pinene) and sesquiterpenes 
((E)-β-caryophyllene, selina-3,7(11)-diene, and other some unidentified 
compounds) were also detected. Only sesquiterpenes (with the exception of 
(E)-β-caryophyllene) are likely to be synthesized in the osmeterium-associated 
glands. Furthermore, the osmeterial secretion proved to deter predatory ants. 
Our results suggest that the osmeterium, besides serving as an aposematic 
warning for enemies, is an efficient chemical defense, with its own synthesis of 
irritant volatiles.

© 2023. The Author(s).

DOI: 10.1038/s41598-023-33390-x
PMCID: PMC10126055
PMID: 37095102 [Indexed for MEDLINE]

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