Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Nat Prod Res. 2024 Sep 25:1-8. doi: 10.1080/14786419.2024.2408409. Online
ahead  of print.

Profiling 32 alkaloid compounds from Macleaya cordata by UPLC-DAD-QTOF-MS/ms.

Zhou X(1), Peng Y(1), Zhou H(2), Wang W(1), Yi G(1), Xia Q(2), Guo Y(1), Xie 
L(1)(2).

Author information:
(1)College of Chemistry and Chemical Engineering, Central South University of 
Forestry and Technology, Changsha, P. R. China.
(2)College of Material Science and Technology, Central South University of 
Forestry and Technology, Changsha, P. R. China.

Macleaya cordata is a traditional herb medicine with alkaloids as the main 
bioactive substance. To identify alkaloid compounds from M. cordata, its crude 
extract was obtained with 0.2 mol/L hydrochloric acid, and alkaloid compounds in 
the demineralised extract by organic solvents from crude extract were 
qualitatively and quantitatively analysed by UPLC-DAD-QTOF-MS/MS. Through 
systematic analysis of retention times, mass spectrometry data, and diagnostic 
fragmentation pathways and rules, 32 alkaloids were rapidly unambiguously 
identified or tentatively deduced by comparison with standard MS spectra or 
literature data. Among them, 16 minor -alkaloid compounds including nandazurine, 
hydroxychelidonine, capauridine, (-)-dicentrine, leptopine, adlumidine, 
takatonine, (2, 3)-trans-N-(p-hydroxyphenethyl)ferulamide, 
9-ethoxyaristololactam, thalicminine, cassythidine, acetylisocorynoline, 
oxynitidine, crinasiatine, zanthoxyline, and 
7,9-dimethoxy-2,3-methylendioxybenzophenanthridine were found in M. cordata for 
the first time. The abundant alkaloids might be responsible for the bioactivity 
of M. cordata, which laid a foundation for the study of quality control, 
livestock, and clinical applications of M. cordata.

DOI: 10.1080/14786419.2024.2408409
PMID: 39319415


2. Chem Biodivers. 2024 Sep;21(9):e202401247. doi: 10.1002/cbdv.202401247. Epub 
2024 Aug 11.

Selective Activity Against Amastigote Forms of Trypanosoma cruzi and Leishmania 
infantum of Diastereomeric Dicentrine N-oxides.

Tristão DC(1), Barbosa H(1), de Castro Levatti EV(2), Andrade BA(2), Romanelli 
MM(2), Antar GM(3), Tempone AG(2), Lago JHG(1).

Author information:
(1)Center for Natural and Human Sciences, Federal University of ABC, 09210-580, 
Santo Andre, SP, Brazil.
(2)Butantan Institute, 1500, 05503-900, São Paulo, SP, Brazil.
(3)Department of Agricultural and Biological Sciences, Federal University of 
Espirito Santo, 29932-540, São Matheus, ES, Brazil.

As part of our continuous research for the discovery of bioactive compounds 
against Trypanosoma cruzi and Leishmania infantum, the alkaloid (6aS)-dicentrine 
(1) was oxidized to afford (6aS,6S)- (2) and (6aS,6R)- (3) dicentrine-N-oxides. 
Evaluation of the cytotoxicity against NCTC cells indicated that 2 and 3 are 
non-toxic (CC50>200 μM) whereas 1 demonstrated CC50 of 52.0 μM. Concerning T. 
cruzi activity against amastigotes, derivatives 2 and 3 exhibited EC50 values of 
9.9 μM (SI>20.2) and 27.5 μM (SI>7.3), respectively, but 1 is inactive 
(EC50>100 μM). Otherwise, when tested against L. infantum amastigotes, 1 and 3 
exhibited EC50 values of 10.3 μM (SI=5.0) and 12.7 μM (SI>15.7), respectively, 
being 2 inactive (EC50>100 μM). Comparing the effects of positive controls 
benznidazol (EC50=6.5 μM and SI>30.7) and miltefosine (EC50=10.2 μM and 
SI=15.2), it was observed a selective antiparasitic activity to diastereomers 2 
and 3 against T. cruzi and L. infantum. Considering stereochemical aspects, it 
was suggested that the configuration of the new stereocenter formed after 
oxidation of 1 played an important role in the bioactivity against amastigotes 
of both tested parasites.

© 2024 Wiley-VHCA AG, Zurich, Switzerland.

DOI: 10.1002/cbdv.202401247
PMID: 38896778 [Indexed for MEDLINE]


3. Bioorg Chem. 2024 Jun;147:107408. doi: 10.1016/j.bioorg.2024.107408. Epub 2024
 Apr 27.

Exploring the antileishmanial activity of dicentrine from Ocotea puberula 
(Lauraceae) using biomembrane models.

Rosa ME(1), Tristão DC(2), Barbosa H(2), Mendes VM(3), Tempone AG(3), Lago 
JHG(2), Caseli L(4).

Author information:
(1)Institute of Environmental, Chemical and Pharmaceutical Sciences, Federal 
University of São Paulo, 09913-030 Diadema, SP, Brazil.
(2)Center for Natural Sciences and Humanities, Federal University of ABC, Santo 
André, 09210-580, SP, Brazil.
(3)Laboratory of Pathophysiology, Butantan Institute, São Paulo 05508-040, SP, 
Brazil.
(4)Institute of Environmental, Chemical and Pharmaceutical Sciences, Federal 
University of São Paulo, 09913-030 Diadema, SP, Brazil. Electronic address: 
lcaseli@unifesp.br.

This study aimed to assess the antiprotozoal efficacy of dicentrine, an 
aporphine alkaloid isolated from Ocotea puberula, against amastigote forms of 
Leishmania (L.) infantum. Our findings reveal that dicentrine demonstrated a 
notable EC50 value of 10.3 μM, comparable to the positive control miltefosine 
(EC50 of 10.4 μM), while maintaining moderate toxicity to macrophages (CC50 of 
51.9 μM). Utilizing an in silico methodology, dicentrine exhibited commendable 
adherence to various parameters, encompassing lipophilicity, water solubility, 
molecule size, polarity, and flexibility. Subsequently, we conducted additional 
investigations to unravel the mechanism of action, employing Langmuir monolayers 
as models for protozoan cell membranes. Tensiometry analyses unveiled that 
dicentrine disrupts the thermodynamic and mechanical properties of the monolayer 
by expanding it to higher areas and increasing the fluidity of the film. The 
molecular disorder was further corroborated through dilatational rheology and 
infrared spectroscopy. These results contribute insights into the role of 
dicentrine as a potential antiprotozoal drug in its interactions with cellular 
membranes. Beyond elucidating the mechanism of action at the plasma membrane's 
external surface, our study sheds light on drug-lipid interface interactions, 
offering implications for drug delivery and other pharmaceutical applications.

Copyright © 2024 Elsevier Inc. All rights reserved.

DOI: 10.1016/j.bioorg.2024.107408
PMID: 38678776 [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.


4. Int J Mol Sci. 2023 Feb 17;24(4):4070. doi: 10.3390/ijms24044070.

Selective Targeting of Cancer-Related G-Quadruplex Structures by the Natural 
Compound Dicentrine.

Platella C(1), Ghirga F(2), Musumeci D(1), Quaglio D(2), Zizza P(3), Iachettini 
S(3), D'Angelo C(3), Biroccio A(3), Botta B(2), Mori M(4), Montesarchio D(1).

Author information:
(1)Department of Chemical Sciences, University of Naples Federico II, Complesso 
Universitario di Monte S. Angelo, Via Cintia, 21, 80126 Napoli, Italy.
(2)Department of Chemistry and Technology of Drugs, Sapienza University of Rome, 
Piazzale Aldo Moro 5, 00185 Rome, Italy.
(3)Translational Oncology Research Unit, IRCCS-Regina Elena National Cancer 
Institute, Via Elio Chianesi 53, 00144 Rome, Italy.
(4)Department of Biotechnology, Chemistry and Pharmacy, University of Siena, Via 
Aldo Moro 2, 53100 Siena, Italy.

Aiming to identify highly effective and selective G-quadruplex ligands as 
anticancer candidates, five natural compounds were investigated here, i.e., the 
alkaloids Canadine, D-Glaucine and Dicentrine, as well as the flavonoids 
Deguelin and Millettone, selected as analogs of compounds previously identified 
as promising G-quadruplex-targeting ligands. A preliminary screening with the 
G-quadruplex on the Controlled Pore Glass assay proved that, among the 
investigated compounds, Dicentrine is the most effective ligand of telomeric and 
oncogenic G-quadruplexes, also showing good G-quadruplex vs. duplex selectivity. 
In-depth studies in solution demonstrated the ability of Dicentrine to thermally 
stabilize telomeric and oncogenic G-quadruplexes without affecting the control 
duplex. Interestingly, it showed higher affinity for the investigated 
G-quadruplex structures over the control duplex (Kb~106 vs. 105 M-1), with some 
preference for the telomeric over the oncogenic G-quadruplex model. Molecular 
dynamics simulations indicated that Dicentrine preferentially binds the 
G-quadruplex groove or the outer G-tetrad for the telomeric and oncogenic 
G-quadruplexes, respectively. Finally, biological assays proved that Dicentrine 
is highly effective in promoting potent and selective anticancer activity by 
inducing cell cycle arrest through apoptosis, preferentially targeting 
G-quadruplex structures localized at telomeres. Taken together, these data 
validate Dicentrine as a putative anticancer candidate drug selectively 
targeting cancer-related G-quadruplex structures.

DOI: 10.3390/ijms24044070
PMCID: PMC9959918
PMID: 36835480 [Indexed for MEDLINE]

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


5. Molecules. 2021 Oct 10;26(20):6117. doi: 10.3390/molecules26206117.

Natural Aporphine Alkaloids with Potential to Impact Metabolic Syndrome.

Wang FX(1), Zhu N(1), Zhou F(1)(2), Lin DX(1).

Author information:
(1)Nanjing Institute of Product Quality Inspection, Nanjing 210019, China.
(2)School of Biological Sciences & Medical Engineering, Southeast University, 
Nanjing 210096, China.

The incidence and prevalence of metabolic syndrome has steadily increased 
worldwide. As a major risk factor for various diseases, metabolic syndrome has 
come into focus in recent years. Some natural aporphine alkaloids are very 
promising agents in the prevention and treatment of metabolic syndrome and its 
components because of their wide variety of biological activities. These natural 
aporphine alkaloids have protective effects on the different risk factors 
characterizing metabolic syndrome. In this review, we highlight the activities 
of bioactive aporphine alkaloids: thaliporphine, boldine, nuciferine, 
pronuciferine, roemerine, dicentrine, magnoflorine, anonaine, apomorphine, 
glaucine, predicentrine, isolaureline, xylopine, methylbulbocapnine, and 
crebanine. We particularly focused on their impact on metabolic syndrome and its 
components, including insulin resistance and type 2 diabetes mellitus, 
endothelial dysfunction, hypertension and cardiovascular disease, hyperlipidemia 
and obesity, non-alcoholic fatty liver disease, hyperuricemia and kidney damage, 
erectile dysfunction, central nervous system-related disorder, and intestinal 
microbiota dysbiosis. We also discussed the potential mechanisms of actions by 
aporphine alkaloids in metabolic syndrome.

DOI: 10.3390/molecules26206117
PMCID: PMC8540223
PMID: 34684698 [Indexed for MEDLINE]

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