Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Int J Biol Macromol. 2024 Sep 20;280(Pt 2):135870. doi: 
10.1016/j.ijbiomac.2024.135870. Online ahead of print.

Confocal image of three oxoaporphine alkaloids in cancer cell lines and their 
interaction with DNA by multispectroscopic and molecular docking techniques.

Kong LT(1), Zhao CY(1), Xin HY(2), Gu WY(1), Su YX(1), Jia XH(3), Tang WZ(4).

Author information:
(1)School of Pharmacy & Institute of Materia Medica, Shandong First Medical 
University & Shandong Academy of Medical Sciences, NHC Key Laboratory of 
Biotechnology Drugs (Shandong Academy of Medical Sciences), Key Lab for Rare & 
Uncommon Diseases of Shandong Province, Jinan 250117, China.
(2)School of Clinical and Basic Medical Sciences, Shandong First Medical 
University and Shandong Academy of Medical Sciences, Jinan 250117, China.
(3)School of Pharmacy & Institute of Materia Medica, Shandong First Medical 
University & Shandong Academy of Medical Sciences, NHC Key Laboratory of 
Biotechnology Drugs (Shandong Academy of Medical Sciences), Key Lab for Rare & 
Uncommon Diseases of Shandong Province, Jinan 250117, China. Electronic address: 
imjxh@163.com.
(4)School of Pharmacy & Institute of Materia Medica, Shandong First Medical 
University & Shandong Academy of Medical Sciences, NHC Key Laboratory of 
Biotechnology Drugs (Shandong Academy of Medical Sciences), Key Lab for Rare & 
Uncommon Diseases of Shandong Province, Jinan 250117, China. Electronic address: 
tangwenzhao@sdfmu.edu.cn.

Dicentrinone (Di), liriodenine (Li) and lysicamine (Ly) are three natural 
oxoaporphine alkaloids (OAs), which revealed significant biological activity 
such as anticancer, anti-inflammatory and antimicrobial activities and were 
considered as potential lead compounds for the development of new clinical 
chemicals. In the present study, confocal laser scanning fluorescence microscopy 
observation demonstrated these three natural OAs could traverse inside of the 
nucleus and get an opportunity to interact with DNA. Their interaction 
properties with DNA were then investigated simultaneously by two spectral 
fluorescent probes of ethidium bromide (EB) and methyl green (MG), as well as 
UV-vis absorption and cyclic voltammetry measurements, and further verified by 
the molecular docking analysis. Results indicated Di and Li were distinctly 
classified as the intercalative molecules to DNA, however, Ly was confirmed with 
a mixed-mode binding of partial intercalation and groove affinity. Their binding 
ability was revealed as the follows: Di ≥ Li > Ly, which was correlated with 
their structural changes. Thermodynamic studies revealed the binding process of 
Li and Ly with ctDNA was all spontaneous, the hydrophobic interaction was the 
major binding force for Li-ctDNA complex, however, the interaction between Ly 
and ctDNA relied on both hydrophobic and hydrogen binding force. Molecular 
docking provided detailed computational interaction of Di, Li and Ly with DNA, 
which proved the intercalation binding of Li-DNA complex and Di-DNA complex 
stabilizing mainly by the π-π binding force, however, apart from a small 
quantity of π-π interaction, another binding force in the Ly-DNA complex mainly 
was supplied from the weaker Pi-Alkyl, hydrogen bond and Pi-Anion interactions.

Copyright © 2024. Published by Elsevier B.V.

DOI: 10.1016/j.ijbiomac.2024.135870
PMID: 39307493

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.


2. Nat Prod Res. 2024 Aug 2:1-8. doi: 10.1080/14786419.2024.2385023. Online ahead
 of print.

Anti-inflammatory and in silico docking studies of Litsea wightiana (Nees) 
Hook.f. (Lauraceae) leaf constituents.

Habeeba KU(1), Rasmi AR(2).

Author information:
(1)Department of Botany, MES Kalladi College, Mannarkkad, Kerala, India.
(2)PG & Research Department of Botany, Government Victoria College, University 
of Calicut, Palakkad, Kerala, India.

Current study aimed to disclose the anti-inflammatory potential of the 
methanolic leaf extracts of L. wightiana (LWME). The in vitro studies focused on 
enzyme inhibition assays targeting the key enzymes such as cyclooxygenase, 
lipoxygenase and nitric oxide synthase and revealed that LWME effectively 
inhibited the activity of these enzymes. Gene expression studies confirmed the 
anti-inflammatory effect, demonstrating down regulation of genes associated with 
inflammation and key proinflammatory factors such as COX-2, TNF-α, IL-6 and 
NFkB. In vivo anti-inflammatory experiments by carrageenan-induced paw edoema 
method in model animals and inflammation was found to be reduced by 10% 
concentration of extract and significant at P˂0.001 level. GCMS and LCMS 
analysis were conducted and the resulted compounds were docked against target 
proteins indicated that most of the bioactive compounds showed better binding 
affinity with enzymes in which the dicentrinone showed higher affinity and it 
may be useful in the treatment of several ailments.

DOI: 10.1080/14786419.2024.2385023
PMID: 39093996


3. Phytochem Anal. 2023 Dec;34(8):970-983. doi: 10.1002/pca.3265. Epub 2023 Jul
24.

Application of effect-directed analysis using TLC-bioautography for rapid 
isolation and identification of antidiabetic compounds from the leaves of Annona 
cherimola Mill.

Galarce-Bustos O(1), Obregón C(1), Vallejos-Almirall A(2), Folch C(3), Acevedo 
F(4)(5).

Author information:
(1)Laboratorio de Farmacognosia, Facultad de Farmacia, Universidad de 
Concepción, Concepción, Chile.
(2)Grupo Interdisciplinario de Biotecnología Marina (GIBMAR), Centro de 
Biotecnología, Universidad de Concepción, Concepción, Chile.
(3)Departamento de Agroindustrias, Facultad de Ingeniería Agrícola, Universidad 
de Concepción, Chillán, Chile.
(4)Department of Basic Sciences, Faculty of Medicine, Universidad de La 
Frontera, Temuco, Chile.
(5)Center of Excellence translational Medicine, Scientific and Technological 
Bioresource Nucleus, BIOREN, Universidad de La Frontera, Temuco, Chile.

INTRODUCTION: Type 2 diabetes mellitus is a globally prevalent chronic disease 
characterised by hyperglycaemia and oxidative stress. The search for new natural 
bioactive compounds that contribute to controlling this condition and the 
application of analytical methodologies that facilitate rapid detection and 
identification are important challenges for science. Annona cherimola Mill. is 
an important source of aporphine alkaloids with many bioactivities.
OBJECTIVE: The aim of this study is to isolate and identify antidiabetic 
compounds from alkaloid extracts with α-glucosidase and α-amylase inhibitory 
activity from A. cherimola Mill. leaves using an effect-directed analysis by 
thin-layer chromatography (TLC)-bioautography.
METHODOLOGY: Guided fractionation for α-glucosidase and α-amylase inhibitors in 
leaf extracts was done using TLC-bioassays. The micro-preparative TLC was used 
to isolate the active compounds, and the identification was performed by mass 
spectrometry associated with web-based molecular networks. Additionally, in 
vitro estimation of the inhibitory activity and antioxidant capacity was 
performed in the isolated compounds.
RESULTS: Five alkaloids (liriodenine, dicentrinone, N-methylnuciferine, 
anonaine, and moupinamide) and two non-alkaloid compounds 
(3-methoxybenzenepropanoic acid and methylferulate) with inhibitory activity 
were isolated and identified using a combination of simple methodologies. 
Anonaine, moupinamide, and methylferulate showed promising results with an 
outstanding inhibitory activity against both enzymes and antioxidant capacity 
that could contribute to controlling redox imbalance.
CONCLUSIONS: These high-throughput methodologies enabled a rapid isolation and 
identification of seven compounds with potential antidiabetic activity. To our 
knowledge, the estimated inhibitory activity of dicentrinone, 
N-methylnuciferine, and anonaine against α-glucosidase and α-amylase is reported 
here for the first time.

© 2023 John Wiley & Sons, Ltd.

DOI: 10.1002/pca.3265
PMID: 37488746 [Indexed for MEDLINE]


4. Bioorg Chem. 2020 Aug;101:103978. doi: 10.1016/j.bioorg.2020.103978. Epub 2020
 Jun 1.

Interaction of dicentrinone, an antitrypanosomal aporphine alkaloid isolated 
from Ocotea puberula (Lauraceae), in cell membrane models at the air-water 
interface.

Barbosa H(1), da Silva RLCG(2), Costa-Silva TA(1), Tempone AG(3), Antar GM(4), 
Lago JHG(5), Caseli L(6).

Author information:
(1)Center of Natural and Human Sciences, Federal University of ABC, Santo André, 
SP, Brazil.
(2)Department of Chemistry, Federal University of São Paulo, Diadema, SP, 
Brazil.
(3)Centre for Parasitology and Mycology, Instituto Adolfo Lutz, São Paulo, SP, 
Brazil.
(4)Institute of Biosciences, University of São Paulo, São Paulo, SP, Brazil.
(5)Center of Natural and Human Sciences, Federal University of ABC, Santo André, 
SP, Brazil. Electronic address: joao.lago@ufabc.edu.br.
(6)Department of Chemistry, Federal University of São Paulo, Diadema, SP, 
Brazil. Electronic address: lcaseli@unifesp.br.

In the present work, the oxoaporphine alkaloid dicentrinone was isolated, for 
the first time, from leaves of Ocotea puberula (Lauraceae). This alkaloid 
exhibited antiparasitic activity against trypomastigote forms of Trypanosoma 
cruzi (IC50 of 16.4 ± 1.7 μM), similar to the positive control benznidazole 
(IC50 of 18.7 ± 4.1 μM), reduced mammalian cytotoxicity (CC50 > 200 μM), and a 
selectivity index (SI) higher than 12. These results were correlated with the 
effects observed using cellular membrane models, represented by 
1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE), in Langmuir monolayers. 
Dicentrinone was incorporated in the films, submitted to lateral compression, 
and characterized by tensiometry. As observed in compression-decompression and 
time-stability curves, dicentrinone expanded the lipid monolayers, decreased the 
compressional modulus of the film, and reduced the stability of the monolayer. 
Brewster Angle Microscopy and interfacial Infrared Spectroscopy showed that 
dicentrinone causes the monolayers to be segregated in phases, and to increase 
the number of gauche/trans conformers ratio for the lipid acyl methylene groups, 
indicating configurational disorder. As a result, dicentrinone caused a 
disturbance in the cell membrane models, altering the physicochemical properties 
of the lipid surface such as thermodynamic, rheological, morphological, and 
structural aspects. These results can be useful to understand the interactions 
between dicentrinone and lipid biological surfaces at the molecular level.

Copyright © 2020 Elsevier Inc. All rights reserved.

DOI: 10.1016/j.bioorg.2020.103978
PMID: 32534347 [Indexed for MEDLINE]


5. RSC Adv. 2018 Aug 14;8(51):28997-29007. doi: 10.1039/c8ra05338c. eCollection 
2018 Aug 14.

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed 
tandem oxidation/aromatization of 1-Bn-DHIQs.

Zheng B(1), Qu HY(1), Meng TZ(1), Lu X(1), Zheng J(1), He YG(1), Fan QQ(1), Shi 
XX(1).

Author information:
(1)Shanghai Key Laboratory of Chemical Biology and Department of Pharmaceutical 
Engineering, School of Pharmacy, East China University of Science and Technology 
130 Mei-Long Road Shanghai 200237 P. R. China xxshi@ecust.edu.cn.

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, 
dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline 
were developed. The key step of these total syntheses is Cu-catalyzed conversion 
of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines 
(1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed 
conversion has been studied in detail, and was successfully used for 
constructing the 1-Bz-IQ core.

This journal is © The Royal Society of Chemistry.

DOI: 10.1039/c8ra05338c
PMCID: PMC9084380
PMID: 35548004

Conflict of interest statement: There are no conflicts to declare.