Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Nat Commun. 2023 Mar 15;14(1):1446. doi: 10.1038/s41467-023-37133-4.

Revealing evolution of tropane alkaloid biosynthesis by analyzing two genomes in 
the Solanaceae family.

Zhang F(1)(2), Qiu F(1)(2), Zeng J(1)(2), Xu Z(3), Tang Y(1)(2), Zhao T(1)(2), 
Gou Y(1)(2), Su F(1)(2), Wang S(1)(2), Sun X(1)(2), Xue Z(3), Wang W(4), Yang 
C(1)(2), Zeng L(1)(2), Lan X(5), Chen M(6), Zhou J(7), Liao Z(8)(9).

Author information:
(1)State Key Laboratory of Silkworm Genome Biology, School of Life Sciences, 
Southwest University, Chongqing, 400715, China.
(2)Integrative Science Center of Germplasm Creation in Western China (Chongqing) 
Science City & Southwest University, SWU-TAAHC Medicinal Plant Joint R&D Centre, 
Southwest University, Chongqing, 400715, China.
(3)Heilongjiang Key Laboratory of Plant Bioactive Substance Biosynthesis and 
Utilization, Northeast Forestry University, Harbin, Heilongjiang, 150040, China.
(4)College of Horticulture and Landscape Architecture, Southwest University, 
Chongqing, 400715, China.
(5)TAAHC-SWU Medicinal Plant Joint R&D Centre, Tibetan Collaborative Innovation 
Centre of Agricultural and Animal Husbandry Resources, Xizang Agricultural and 
Animal Husbandry College, Nyingchi, Tibet, 860000, China.
(6)College of Pharmaceutical Sciences, Key Laboratory of Luminescent and 
Real-Time Analytical Chemistry (Ministry of Education), Southwest University, 
Chongqing, 400715, China.
(7)State Key Laboratory of Dao-di Herbs, National Resource Center for Chinese 
Materia Medica, China Academy of Chinese Medical Sciences, Beijing, 100700, 
China.
(8)State Key Laboratory of Silkworm Genome Biology, School of Life Sciences, 
Southwest University, Chongqing, 400715, China. zhliao@swu.edu.cn.
(9)Integrative Science Center of Germplasm Creation in Western China (Chongqing) 
Science City & Southwest University, SWU-TAAHC Medicinal Plant Joint R&D Centre, 
Southwest University, Chongqing, 400715, China. zhliao@swu.edu.cn.

Tropane alkaloids (TAs) are widely distributed in the Solanaceae, while some 
important medicinal tropane alkaloids (mTAs), such as hyoscyamine and 
scopolamine, are restricted to certain species/tribes in this family. Little is 
known about the genomic basis and evolution of TAs biosynthesis and 
specialization in the Solanaceae. Here, we present chromosome-level genomes of 
two representative mTAs-producing species: Atropa belladonna and Datura 
stramonium. Our results reveal that the two species employ a conserved 
biosynthetic pathway to produce mTAs despite being distantly related within the 
nightshade family. A conserved gene cluster combined with gene duplication 
underlies the wide distribution of TAs in this family. We also provide evidence 
that branching genes leading to mTAs likely have evolved in early ancestral 
Solanaceae species but have been lost in most of the lineages, with A. 
belladonna and D. stramonium being exceptions. Furthermore, we identify a 
cytochrome P450 that modifies hyoscyamine into norhyoscyamine. Our results 
provide a genomic basis for evolutionary insights into the biosynthesis of TAs 
in the Solanaceae and will be useful for biotechnological production of mTAs via 
synthetic biology approaches.

© 2023. The Author(s).

DOI: 10.1038/s41467-023-37133-4
PMCID: PMC10017790
PMID: 36922496 [Indexed for MEDLINE]

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


2. Phytochemistry. 2012 Feb;74:105-14. doi: 10.1016/j.phytochem.2011.10.010. Epub
 2011 Nov 13.

Norlittorine and norhyoscyamine identified as products of littorine and 
hyoscyamine metabolism by (13)C-labeling in Datura innoxia hairy roots.

Al Balkhi MH(1), Schiltz S, Lesur D, Lanoue A, Wadouachi A, Boitel-Conti M.

Author information:
(1)Unité de Biologie des Plantes et Insectes ravageurs, Université de Picardie 
Jules Verne, 33 rue Saint Leu, F-80039 Amiens Cedex, France.

The presence of two compounds, norlittorine and norhyoscyamine, has been 
reported in leaves and roots of Datura innoxia; however their metabolic origin 
in the tropane alkaloid pathway has remained unknown. Precise knowledge of this 
pathway is a necessary pre-requisite to optimize the production of hyoscyamine 
and scopolamine in D. innoxia hairy root cultures. The exact structure of 
norlittorine and norhyoscyamine was confirmed by LC-MS/MS and NMR analyses. 
Isotopic labeling experiments, using [1-(13)C]-phenylalanine, 
[1'-(13)C]-littorine and [1'-(13)C]-hyoscyamine, combined with elicitor 
treatments, using methyl jasmonate, coronalon and 
1-aminocyclopropane-1-carboxylic acid, were used to investigate the metabolic 
origin of the N-demethylated tropane alkaloids. The results suggest that 
norlittorine and norhyoscyamine are induced under stress conditions by 
conversion of littorine and hyoscyamine. We propose the N-demethylation of 
tropane alkaloids as a mechanism to detoxify cells in overproducing conditions.

Copyright © 2011 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.phytochem.2011.10.010
PMID: 22083085 [Indexed for MEDLINE]


3. Electrophoresis. 2008 May;29(10):2112-6. doi: 10.1002/elps.200700468.

Characterization of Atropa belladonna L. compounds by capillary 
electrophoresis-electrospray ionization-time of flight-mass spectrometry and 
capillary electrophoresis-electrospray ionization-ion trap-mass spectrometry.

Arráez-Román D(1), Zurek G, Bässmann C, Segura-Carretero A, Fernández-Gutiérrez 
A.

Author information:
(1)Department of Analytical Chemistry, Faculty of Sciences, University of 
Granada, Granada, Spain.

This short communication describes the characterization of seven tropane 
alkaloid compounds in Atropa belladonna L. Thus a rapid and easy CE-electrospray 
interface (ESI)-TOF-MS procedure is developed to analyze these compounds in a 
pharmaceutical preparations of A. belladonna L. leaf extract. Optimum 
electrophoretic separation is obtained using an alkaline solution of 60 mM 
ammonium acetate at pH 8.5 containing 5% isopropanol. Under the optimum 
CE-ESI-TOF-MS conditions several important compounds such as tropine, 
belladonnine, norhyoscyamine, apoatropine, hyoscyamine, 
6beta-hydroxyhyoscyamine, and scopolamine have been simultaneously identified 
from A. belladonna L. CE-ESI-IT-MS has been used to discriminate the putative 
presence of littorine. The sensitivity, together with mass accuracy and true 
isotopic pattern of the TOF-MS, allowed the identification of a broad series of 
tropane alkaloid compounds present in pharmaceutical preparations of A. 
belladonna L. leaf extract.

DOI: 10.1002/elps.200700468
PMID: 18425749 [Indexed for MEDLINE]


4. Planta Med. 1986 Oct;(5):390-5. doi: 10.1055/s-2007-969194.

Reinvestigation of the Alkaloid Composition of Atropa belladonna Plants, Root 
Cultures, and Cell Suspension Cultures.

Hartmann T(1), Witte L, Oprach F, Toppel G.

Author information:
(1)Institut für Pharmazeutische Biologie der Technischen Universität, 
Mendelssohnstr. 1, D-3300 Braunschweig, Federal Republic of Germany.

The alkaloid composition of ATROPA BELLADONNA was analyzed by high resolution 
GLC and GLC-MS. A total of 13 alkaloids, most new for ATROPA, were identified 
from roots. The aboveground parts of the plant revealed 7 alkaloids; the 
hygrines were completely absent. The alkaloid pattern of root cultures was 
almost identical with the pattern of roots from intact plants. The patterns 
differed only quantitatively. Scopolamine which in A. BELLADONNA seems to be 
synthesized in the roots only, was preferably excreted into the culture medium. 
Norhyoscyamine was found frequently in plant shoots. The occurrence of 
hyoscyamine N-oxide in various plant organs could be confirmed. Cell suspension 
cultures produced trace amounts of hyoscyamine, 3alpha-acetoxytropane and 
3alpha-tigloyloxytropane. The last two ester alkaloids were not detectable in 
intact plants.

DOI: 10.1055/s-2007-969194
PMID: 17345349