Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. J Hazard Mater. 2024 Oct 17;480:136192. doi: 10.1016/j.jhazmat.2024.136192. 
Online ahead of print.

A comprehensive study on the digestion, absorption, and metabolization of 
tropane alkaloids in human cell models.

Marín-Sáez J(1), Lopez-Ruiz R(2), Faria MA(3), Ferreira IMPLVO(4), Garrido 
Frenich A(5).

Author information:
(1)Research Group "Analytical Chemistry of Contaminants", Department of 
Chemistry and Physics, Research Centre for Mediterranean Intensive Agrosystems 
and Agri-Food Biotechnology (CIAIMBITAL), University of Almeria, Agrifood Campus 
of International Excellence, ceiA3, E-04120 Almeria, Spain; LAQV/REQUIMTE, 
Departamento de Ciências Químicas, Laboratório de Bromatologia e Hidrologia, 
Faculdade de Farmácia, Universidade do Porto, Porto, Portugal. Electronic 
address: jms485@ual.es.
(2)Research Group "Analytical Chemistry of Contaminants", Department of 
Chemistry and Physics, Research Centre for Mediterranean Intensive Agrosystems 
and Agri-Food Biotechnology (CIAIMBITAL), University of Almeria, Agrifood Campus 
of International Excellence, ceiA3, E-04120 Almeria, Spain; LAQV/REQUIMTE, 
Departamento de Ciências Químicas, Laboratório de Bromatologia e Hidrologia, 
Faculdade de Farmácia, Universidade do Porto, Porto, Portugal. Electronic 
address: rlr468@ual.es.
(3)LAQV/REQUIMTE, Departamento de Ciências Químicas, Laboratório de Bromatologia 
e Hidrologia, Faculdade de Farmácia, Universidade do Porto, Porto, Portugal. 
Electronic address: mfaria@ff.up.pt.
(4)LAQV/REQUIMTE, Departamento de Ciências Químicas, Laboratório de Bromatologia 
e Hidrologia, Faculdade de Farmácia, Universidade do Porto, Porto, Portugal. 
Electronic address: isabel.ferreira@ff.up.pt.
(5)Research Group "Analytical Chemistry of Contaminants", Department of 
Chemistry and Physics, Research Centre for Mediterranean Intensive Agrosystems 
and Agri-Food Biotechnology (CIAIMBITAL), University of Almeria, Agrifood Campus 
of International Excellence, ceiA3, E-04120 Almeria, Spain. Electronic address: 
agarrido@ual.es.

Tropane alkaloids (TAs) are toxic compounds with potent anticholinergic effects. 
Herbal infusions are among the most contaminated food commodities; however, the 
fate of TAs after ingestion remains poorly understood. This study presents a 
comprehensive investigation into the absorption, and metabolism of five TAs 
(atropine, scopolamine, tropine, homatropine, and apoatropine) following the 
digestion of contaminated tea. In vitro human cell models were employed, 
including gastric (NCI-N87), intestinal (Caco-2:HT29-MTX), and hepatic (HEP-G2) 
cells. TAs were found to be highly absorbed in the intestinal epithelium, while 
gastric cells exhibited poor absorption. Metabolism was studied using a 
custom-made database, revealing that it occurs predominantly in intestinal 
cells, involving hydroxylation and methylation reactions. Cell metabolomics was 
conducted using annotation, fragment simulation, and statistical software 
platforms. Significant statistical differences were observed for 40 tentatively 
identified compounds. MetaboAnalyst 5.0 was employed to discern the most 
disturbed metabolic pathways, with amoniacids biosynthesis pathways and TCA 
cycles being the most affected. These pathways are involved in responses to 
cellular metabolic stress, neurotransmitter production, cellular energy 
generation, and the regulation of oxidative stress response. The findings of 
this study enhance our understanding of the fate of TAs after ingestion, their 
metabolization and their effects at the cellular level.

Copyright © 2024 Elsevier B.V. All rights reserved.

DOI: 10.1016/j.jhazmat.2024.136192
PMID: 39427354

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. J Nat Prod. 2024 Aug 23;87(8):1914-1920. doi: 10.1021/acs.jnatprod.4c00304.
Epub  2024 Jul 22.

Identification of Granatane Alkaloids from Duboisia myoporoides (Solanaceae) 
using Molecular Networking and Semisynthesis.

Dutertre Q(1)(2), Guy PA(1), Sutour S(3), Peitsch MC(1), Ivanov NV(1), Glauser 
G(3), von Reuss S(2)(3).

Author information:
(1)Philip Morris Product SA, Quai Jeanrenaud 3, Neuchâtel 2000, Switzerland.
(2)Laboratory of Bioanalytical Chemistry, University of Neuchâtel, Neuchâtel 
2000, Switzerland.
(3)Neuchâtel Platform of Analytical Chemistry (NPAC), University of Neuchâtel, 
Neuchâtel 2000, Switzerland.

The Solanaceae plant family contains at least 98 genera and over 2700 species. 
The Duboisia genus stands out for its ability to produce pyridine and tropane 
alkaloids, which are relatively poorly characterized at the phytochemical level. 
In this study, we analyzed dried leaves of Duboisia spp. using supercritical CO2 
extraction and ultra-high-pressure liquid chromatography coupled to 
high-resolution tandem mass spectrometry, followed by feature-based molecular 
networking. Thirty-one known tropane alkaloids were putatively annotated, and 
the identity of six (atropine, scopolamine, anisodamine, aposcopolamine, 
apoatropine, and noratropine) were identified using reference standards. Two new 
granatane alkaloids connected in the molecular network were highlighted from 
Duboisia myoporoides, and their α-granatane tropate and α-granatane isovalerate 
structures were unambiguously established by semisynthesis.

DOI: 10.1021/acs.jnatprod.4c00304
PMCID: PMC11348422
PMID: 39038492 [Indexed for MEDLINE]

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


3. Food Chem. 2021 Feb 1;337:127617. doi: 10.1016/j.foodchem.2020.127617. Epub
2020  Jul 29.

Indirect competitive enzyme-linked immunosorbent assay based on a broad-spectrum 
monoclonal antibody for tropane alkaloids detection in pig urine, pork and 
cereal flours.

Wang Z(1), Zheng P(1), Wang J(1), He S(1), Ren Z(1), Zhang Y(1), Xiong J(1), 
Jiang H(2).

Author information:
(1)Beijing Advanced Innovation Center for Food Nutrition and Human Health, 
Beijing Key Laboratory of Detection Technology for Animal-Derived Food Safety, 
Beijing Laboratory for Food Quality and Safety, College of Veterinary Medicine, 
China Agricultural University, Beijing 100193, People's Republic of China.
(2)Beijing Advanced Innovation Center for Food Nutrition and Human Health, 
Beijing Key Laboratory of Detection Technology for Animal-Derived Food Safety, 
Beijing Laboratory for Food Quality and Safety, College of Veterinary Medicine, 
China Agricultural University, Beijing 100193, People's Republic of China. 
Electronic address: haiyang@cau.edu.cn.

In this study, an indirect competitive enzyme-linked immunosorbent assay 
(ic-ELISA) based on a broad-spectrum monoclonal antibody for tropane alkaloids 
(TAs) was established for the rapid screening of atropine, scopolamine, 
homatropine, apoatropine, anisodamine, anisodine and L-hyoscyamine residues in 
pig urine, pork and cereal flour samples through a simple sample preparation 
procedure. The half inhibitory concentrations of atropine, homatropine, 
L-hyoscyamine, apoatropine, scopolamine, anisodamine and anisodine were 0.05, 
0.07, 0.14, 0.14, 0.24, 5.30 and 10.15 ng mL-1, respectivelyThe detection and 
quantitative limits of this method for TAs in samples were 0.18-73.18 and 
0.44-74.77 μg kg-1. The spiked recoveries ranged from 69.88% to 147.93%, and the 
coefficient of variations were less than 14%. Good correlation (R2 = 0.9929) 
between the results of the ic-ELISA and the high performance liquid 
chromatography-tandem mass spectrometry support the reliability of the developed 
ic-ELISA method.

Copyright © 2020 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.foodchem.2020.127617
PMID: 32799156 [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. Food Chem. 2019 Mar 1;275:746-753. doi: 10.1016/j.foodchem.2018.09.137. Epub 
2018 Sep 24.

Reliable determination of tropane alkaloids in cereal based baby foods coupling 
on-line spe to mass spectrometry avoiding chromatographic step.

Marín-Sáez J(1), Romero-González R(1), Garrido Frenich A(2).

Author information:
(1)Department of Chemistry and Physics, Analytical Chemistry Area, University of 
Almería, Research Centre for Agricultural and Food Biotechnology (BITAL), 
Agrifood Campus of International Excellence ceiA3, Carretera de Sacramento s/n, 
E-04120 Almería, Spain.
(2)Department of Chemistry and Physics, Analytical Chemistry Area, University of 
Almería, Research Centre for Agricultural and Food Biotechnology (BITAL), 
Agrifood Campus of International Excellence ceiA3, Carretera de Sacramento s/n, 
E-04120 Almería, Spain. Electronic address: agarrido@ual.es.

Cereal based foods are a major part of the infant diet and they can be 
contaminated with Solanaceae and other plants containing tropane alkaloids. This 
study was focused on the optimisation of an extraction procedure based on a 
solid-liquid method and an online SPE system, directly coupled to different mass 
spectrometry analysers as Orbitrap and triple quadrupole (QqQ), removing the 
chromatographic separation step. Total running analysis time was 15.8 min 
(17.3 min in the QqQ system). The developed method was validated obtaining 
recoveries ranging from 66 to 98% and 68-97% for the Orbitrap and QqQ 
respectively (RSD lower than 14.3%) and limits of quantification from 0.5 to 
5 µg kg-1 and 0.5-10 µg kg-1 for the QqQ and Orbitrap analyser respectively. The 
validated method was applied to several cereal based baby food samples, finding 
a positive sample containing atropine (11.5 µg kg-1), scopolamine (2.8 µg kg-1) 
and apoatropine (7.5 µg kg-1).

Copyright © 2018 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.foodchem.2018.09.137
PMID: 30724258 [Indexed for MEDLINE]


5. Drug Test Anal. 2018 Oct;10(10):1579-1589. doi: 10.1002/dta.2416. Epub 2018
Jun  29.

Screening of drugs and homeopathic products from Atropa belladonna seed 
extracts: Tropane alkaloids determination and untargeted analysis.

Marín-Sáez J(1), Romero-González R(1), Garrido Frenich A(1), Egea-González 
FJ(1).

Author information:
(1)Department of Chemistry and Physics, Analytical Chemistry Area, University of 
Almería, Research Centre for Agricultural and Food Biotechnology (BITAL), 
Agrifood Campus of International Excellence ceiA3, Almería, Spain.

Homeopathic products are still a controversial issue in modern medicine, 
understood as complementary or alternative medicine (CAM). In this particular 
case, homeopathic products prepared from Atropa belladonna extracts may present 
specific problems due to the effects derived from its components. This article 
applies a simple, rapid, reliable method to the analysis of different 
homeopathic products obtained from Atropa belladonna; drugs containing high 
concentration of plant extracts; and Atropa belladonna seeds. The method was 
based on a simple solid-phase preconcentration method followed by ultra-high 
pressure liquid chromatography (UHPLC) coupled to high resolution mass 
spectrometry using Exactive-Orbitrap as an analyser. An in-house database was 
set and atropine and scopolamine were the compounds detected at highest 
concentrations in homeopathic products from Atropa belladonna extracts (4.57 and 
2.56 μg/kg, respectively), in Belladonna ointment (4007 and 1139 μg/kg, 
respectively) and Belladonna seeds (338 and 32.1 mg/kg, respectively). Other 
tropane alkaloids such as tropine, apoatropine, aposcopolamine, tropinone, 
homatropine, and anisodamine were detected at lower concentrations 
(0.04-1.36 μg/kg). When untargeted analysis was performed, other tropane 
alkaloids were identified in the tested samples, such as ecgonine (0.003 μg/kg), 
benzoylecgonine (0.56 μg/kg), calystegines A (19.6 μg/kg), B (33.1 μg/kg), and C 
(1.01 μg/kg). Finally other compounds present in the homeopathic products, such 
as sugars (fructose, glucose, and lactose) or amino acids (valine, ornithine, 
leucine, and phenylalanine), were identified.

Copyright © 2018 John Wiley & Sons, Ltd.

DOI: 10.1002/dta.2416
PMID: 29808589 [Indexed for MEDLINE]