Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Molecules. 2022 Mar 28;27(7):2200. doi: 10.3390/molecules27072200.

Isolation and Structural Elucidation of Compounds from Pleiocarpa bicarpellata 
and Their In Vitro Antiprotozoal Activity.

Sevik Kilicaslan O(1)(2), Cretton S(1)(2), Quirós-Guerrero L(1)(2), Bella MA(3), 
Kaiser M(4)(5), Mäser P(4)(5), Ndongo JT(3), Cuendet M(1)(2).

Author information:
(1)School of Pharmaceutical Sciences, University of Geneva, 1211 Geneva, 
Switzerland.
(2)Institute of Pharmaceutical Sciences of Western Switzerland, University of 
Geneva, 1211 Geneva, Switzerland.
(3)Department of Chemistry, Higher Teacher Training College, University of 
Yaoundé 1, Yaoundé P.O. Box 47, Cameroon.
(4)Swiss Tropical and Public Health Institute, 4002 Basel, Switzerland.
(5)University of Basel, 4003 Basel, Switzerland.

Species of the genus Pleiocarpa are used in traditional medicine against fever 
and malaria. The present study focuses on the isolation and identification of 
bioactive compounds from P. bicarpellata extracts, and the evaluation of their 
antiprotozoal activity. Fractionation and isolation combined to LC-HRMS/MS-based 
dereplication provided 16 compounds: seven indole alkaloids, four indoline 
alkaloids, two secoiridoid glycosides, two iridoid glycosides, and one phenolic 
glucoside. One of the quaternary indole alkaloids (7) and one indoline alkaloid 
(15) have never been reported before. Their structures were elucidated by 
analysis of spectroscopic data, including 1D and 2D NMR experiments, UV, IR, and 
HRESIMS data. The absolute configurations were determined by comparison of the 
experimental and calculated ECD data. The extracts and isolated compounds were 
evaluated for their antiprotozoal activity towards Trypanosoma brucei 
rhodesiense, Trypanosoma cruzi, Leishmania donovani, and Plasmodium falciparum, 
as well as for their cytotoxicity against rat skeletal myoblast L6 cells. The 
dichloromethane/methanol (1:1) root extract showed strong activity against P. 
falciparum (IC50 value of 3.5 µg/mL). Among the compounds isolated, tubotaiwine 
(13) displayed the most significant antiplasmodial activity with an IC50 value 
of 8.5 µM and a selectivity index of 23.4. Therefore, P. bicarpallata extract 
can be considered as a source of indole alkaloids with antiplasmodial activity.

DOI: 10.3390/molecules27072200
PMCID: PMC9000413
PMID: 35408605 [Indexed for MEDLINE]

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


2. Dokl Biochem Biophys. 2021 Sep;500(1):368-375. doi: 10.1134/S1607672921050136.
 Epub 2021 Oct 25.

Protective Effect of Tubotaiwine on Cadmium-Induced Hypertension in Rats through 
Reduction in Arterial Stiffness and Vascular Remodeling.

Gao L(1), Li X(2).

Author information:
(1)Department of Cardiovascular Medicine, Danyang People's Hospital of Jiangsu 
Province, 212300, Danyang, Jiangsu, China.
(2)Department of Radiology, the First People's Hospital of Jingmen City, 448000, 
Jingmen City, Hubei Province, China. xiaolinli.edu@gmail.com.

Humans are adversely affected by exposure to cadmium (Cd) as it induces 
oxidative stress which damages kidneys, bones pulmonary tissues, liver, 
cardiovascular, immune, reproductive systems and influences endocrine 
secretions. In the present study tubotaiwine treatment regulated systolic, 
diastolic and mean arterial blood pressure of the Cd exposed rats. Tubotaiwine 
significantly promoted vascular responsiveness to Phe, ACh and SNP and reversed 
Cd mediated decrease in eNOS and increase in iNOS expression. Treatment of the 
Cd exposed rats with tubotaiwine reduced number of smooth muscle cells, 
decreased collagen content and promoted content of elastin in aortic artery 
walls. Tubotaiwine treatment significantly suppressed Cd-induced increase in 
MMP-2 and MMP-9 in rat aortic artery tissues. Increase in O2-, urinary 
nitrate/nitrite, MDA, carbonyl level and decrease in GSH production in rat blood 
and thoracic aorta tissues were effectively reversed by tubotaiwine treatment. 
Tubotaiwine treatment of the rats significantly reduced Cd-induced increase in 
blood, liver, heart and kidney tissue Cd content in dose dependent manner. Thus, 
tubotaiwine suppresses Cd induced hypertension in rats by reducing arterial 
stiffness, inhibition of oxidative stress and increasing vascular remodeling. 
Therefore, tubotaiwine has beneficial effect on Cd induced hypertension in rats 
and may be developed as a potential candidate for treatment of hypertension.

© 2021. Pleiades Publishing, Ltd.

DOI: 10.1134/S1607672921050136
PMID: 34697745 [Indexed for MEDLINE]


3. Plants (Basel). 2020 Aug 3;9(8):983. doi: 10.3390/plants9080983.

Three Alkaloids from an Apocynaceae Species, Aspidosperma spruceanum as 
Antileishmaniasis Agents by In Silico Demo-case Studies.

Morales-Jadán D(1)(2), Blanco-Salas J(1), Ruiz-Téllez T(1), Centeno F(2).

Author information:
(1)Ecology and Earth Science, Department of Vegetal Biology, Faculty of 
Sciences, University of Extremadura, 06006 Badajoz, Spain.
(2)Molecular Biology and Genetics, Department of Biochemistry, Faculty of 
Sciences, University of Extremadura, 06006 Badajoz, Spain.

This paper is focused on demonstrating with a real case that Ethnobotany added 
to Bioinformatics is a promising tool for new drugs search. It encourages the in 
silico investigation of "challua kaspi", a medicinal kichwa Amazonian plant 
(Aspidosperma spruceanum) against a Neglected Tropical Disease, leishmaniasis. 
The illness affects over 150 million people especially in subtropical regions, 
there is no vaccination and conventional treatments are unsatisfactory. In 
attempts to find potent and safe inhibitors of its etiological agent, 
Leishmania, we recovered the published traditional knowledge on kichwa 
antimalarials and selected three A. spruceanum alkaloids, (aspidoalbine, 
aspidocarpine and tubotaiwine), to evaluate by molecular docking their activity 
upon five Leishmania targets: DHFR-TS, PTR1, PK, HGPRT and SQS enzymes. Our 
simulation results suggest that aspidoalbine interacts competitively with the 
five targets, with a greater affinity for the active site of PTR1 than some 
physiological ligands. Our virtual data also point to the demonstration of few 
side effects. The predicted binding free energy has a greater affinity to 
Leishmania proteins than to their homologous in humans (TS, DHR, PKLR, HGPRT and 
SQS), and there is no match with binding pockets of physiological importance. 
Keys for the in silico protocols applied are included in order to offer a 
standardized method replicable in other cases. Apocynaceae having ethnobotanical 
use can be virtually tested as molecular antileishmaniasis new drugs.

DOI: 10.3390/plants9080983
PMCID: PMC7465237
PMID: 32756456

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


4. Plants (Basel). 2019 Nov 22;8(12):534. doi: 10.3390/plants8120534.

Methyljasmonate Elicitation Increases Terpenoid Indole Alkaloid Accumulation in 
Rhazya stricta Hairy Root Cultures.

Akhgari A(1)(2), Laakso I(3), Maaheimo H(1), Choi YH(4), Seppänen-Laakso T(1), 
Oksman-Caldentey KM(1), Rischer H(1).

Author information:
(1)VTT Technical Research Centre of Finland Ltd., P.O. Box 1000, VTT, Espoo 
02044, Finland.
(2)Department of Biochemistry, University of Turku, Turku 20014, Finland.
(3)Division of Pharmaceutical Biosciences, Faculty of Pharmacy, P.O. Box 56, 
University of Helsinki, Helsinki, 00014, Finland.
(4)Natural Products Laboratory, Institute of Biology, Leiden University, 
Sylviusweg BE, Leiden 72, 2333, The Netherlands.

Methyl jasmonate is capable of initiating or improving the biosynthesis of 
secondary metabolites in plants and therefore has opened up a concept for the 
biosynthesis of valuable constituents. In this study, the effect of different 
doses of methyl jasmonate (MeJA) elicitation on the accumulation of terpenoid 
indole alkaloids (TIAs) in the hairy root cultures of the medicinal plant, 
Rhazya stricta throughout a time course (one-seven days) was investigated. Gas 
chromatography-mass spectrometry (GC-MS) analyses were carried out for targeted 
ten major non-polar alkaloids. Furthermore, overall alterations in metabolite 
contents in elicited and control cultures were investigated applying proton 
nuclear magnetic resonance (1H NMR) spectroscopy. Methyl jasmonate caused 
dosage- and time course-dependent significant rise in the accumulation of TIAs 
as determined by GC-MS. The contents of seven alkaloids including eburenine, 
quebrachamine, fluorocarpamine, pleiocarpamine, tubotaiwine, 
tetrahydroalstonine, and ajmalicine increased compared to non-elicited cultures. 
However, MeJA-elicitation did not induce the accumulation of vincanine, 
yohimbine (isomer II), and vallesiachotamine. Furthermore, principal component 
analysis (PCA) of 1H NMR metabolic profiles revealed a discrimination between 
elicited hairy roots and control cultures with significant increase in total 
vindoline-type alkaloid content and elevated levels of organic and amino acids. 
In addition, elicited and control samples had different sugar and fatty acid 
profiles, suggesting that MeJA also influences the primary metabolism of R. 
stricta hairy roots. It is evident that methyl jasmonate is applicable for 
elevating alkaloid accumulation in "hairy root" organ cultures of R. strica.

DOI: 10.3390/plants8120534
PMCID: PMC6963348
PMID: 31766620

Conflict of interest statement: The authors declare that they have no conflict 
of interests.


5. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jul 15;1026:43-55. doi: 
10.1016/j.jchromb.2015.07.044. Epub 2015 Jul 29.

Characterization of chemical constituents and rats metabolites of an alkaloidal 
extract of Alstonia scholaris leaves by liquid chromatography coupled with mass 
spectrometry.

Cao J(1), Shen HM(2), Wang Q(1), Qian Y(1), Guo HC(1), Li K(1), Qiao X(1), Guo 
DA(1), Luo XD(3), Ye M(4).

Author information:
(1)State Key Laboratory of Natural and Biomimetic Drugs, School of 
Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, 
China.
(2)The Third Affiliated Hospital of Kunming Medical University, Kunming 650106, 
Yunnan Province, China.
(3)State Key Laboratory of Phytochemistry and Plant Resources in West China, 
Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, Yunnan 
Province, China. Electronic address: xdluo@kib.ac.cn.
(4)State Key Laboratory of Natural and Biomimetic Drugs, School of 
Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, 
China. Electronic address: yemin@bjmu.edu.cn.

Alstonia scholaris has been used in "Dai" ethnic medicine to treat chronic 
respiratory diseases for a long history, and the major bioactive constituents 
are alkaloids. An alkaloidal extract of A. scholaris leaves (AAS) has been 
developed into an investigational new drug, and has been approved for phase I/II 
clinical trials by China Food and Drug Administration. However, little is known 
on the chemical composition and in vivo metabolism of AAS, thus far. In this 
study, an ultra-high performance liquid chromatography coupled with quadrupole 
time-of-flight mass spectrometry (UHPLC/qTOF-MS) method was established to 
characterize the chemical constituents of AAS. Samples were separated on an 
ACQUITY UPLC CSH column (2.1×100mm, 1.7μm) with acetonitrile and water 
containing 0.3% formic acid as the mobile phase. On the basis of high-accuracy 
mass spectral analysis, a total of 35 alkaloids were characterized from AAS, 
including 11 scholaricine-type, 9 vallesamine-type, 12 picrinine-type, and 3 
tubotaiwine-type alkaloids. Furthermore, the metabolic pathways of 4 
representative alkaloids in rats were studied. They mainly undertook 
hydroxylation and glucuronidation reactions. Based on the above metabolic 
pathways, the metabolism of AAS (10mg/kg) in rats after oral administration was 
studied by LC/MS. A total of 33 compounds in plasma, 40 compounds in urine, and 
38 compounds in feces were characterized. The results indicated that 
scholaricine-type alkaloids could get into circulation more readily than the 
other types. This is the first systematic study on chemical profiling and 
metabolites identification of AAS.

Copyright © 2015 Elsevier B.V. All rights reserved.

DOI: 10.1016/j.jchromb.2015.07.044
PMID: 26275898 [Indexed for MEDLINE]