Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Toxicon. 2020 Dec;188:134-141. doi: 10.1016/j.toxicon.2020.10.019. Epub 2020
Oct  20.

Cytotoxic activity induced by the alkaloid extract from Ipomoea carnea on 
primary murine mixed glial cultures.

Cholich LA(1), Pistán ME(2), Torres AM(3), Ortega HH(4), Gardner DR(5), Bustillo 
S(6).

Author information:
(1)Faculty of Veterinary Science, National University of the Northeast, 
Corrientes, Argentina; The National Scientific and Technical Research Council 
(CONICET), Argentina. Electronic address: lucianaandreacholich@gmail.com.
(2)Faculty of Veterinary Science, National University of the Northeast, 
Corrientes, Argentina; The National Scientific and Technical Research Council 
(CONICET), Argentina.
(3)Natural Products Laboratory, IQUIBA-NEA CONICET, National University of the 
Northeast, Corrientes, Argentina.
(4)Institute of Veterinary Sciences of Litoral (ICIVET), National University of 
Litoral (UNL), Esperanza, Santa Fe, Argentina; The National Scientific and 
Technical Research Council (CONICET), Argentina.
(5)USDA-ARS Poisonous Plant Research Laboratory, Logan, UT, USA.
(6)Biological and Molecular Investigations Group (GIBYM), IQUIBA-NEA CONICET, 
National University of the Northeast, Corrientes, Argentina.

The prolonged consumption of Ipomoea carnea produces neurologic symptoms in 
animals and a typical histological lesion, cytoplasmic vacuolization, especially 
in neurons. The toxic principles of I. carnea are the alkaloids swainsonine and 
calystegines B1, B2, B3 and C1. In this study, primary brain cultures from 
newborn mouse containing mixed glial cells were utilized. These cells were 
exposed to Ipomoea extracts containing between 0 and 250 μM swainsonine for 
48 h. Morphological changes were investigated through Phase Contrast microscopy 
and Rosenfeld's staining. The extract induced cytoplasmic vacuolization in 
astrocytes and microglia in a dose dependent manner, being more evident when 
cultures were exposed to 250 μM of swainsonine. In addition, acridine orange 
staining evidenced an increase in the number of lysosomes in both microglia and 
astrocytes cells. Consistent with this, scanning electron microscopy also showed 
that both types of cells presented morphological characteristics of cell 
activation. Ultrastructurally, cells showed vacuoles filled with amorphous 
material and surrounded by a single membrane and also multilayer membranes. 
Taken together, these findings suggest that swainsonine along with calystegines, 
are probably responsible for the activation of glial cells due to a possible 
lysosomal dysfunction and therefore intracellular storage. Our results 
demonstrate that this in vitro glial cell model is a very good alternative to in 
vivo studies that require several weeks of animal intoxication to observe 
similar neurotoxic effects.

Copyright © 2020 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.toxicon.2020.10.019
PMID: 33091389 [Indexed for MEDLINE]


2. J Chromatogr A. 2018 Nov 16;1576:51-57. doi: 10.1016/j.chroma.2018.09.030.
Epub  2018 Sep 17.

Analysis of calystegines in tomato-based products by liquid 
chromatography-Orbitrap mass spectrometry.

Romera-Torres A(1), Romero-González R(1), Martínez Vidal JL(1), Garrido Frenich 
A(2).

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

Taking into account the high consumption of tomato and tomato-based products, a 
study of the occurrence of 7 nortropane alkaloids (calystegines A3, A5, B1, B2, 
B3, B4 and C1) in this type of matrix has been performed. For that purpose, a 
simple and fast solid-liquid extraction with methanol/water (50/50, v/v) has 
been developed, and then liquid chromatography, using a HILIC-A as stationary 
phase, coupled to high resolution mass spectrometry (LC-HRMS-Orbitrap) has been 
used for their determination. The developed method was validated and recoveries 
ranged from 96 to 121%, and relative standard deviations lower than or equal to 
16% were obtained. Limits of quantification (LOQ) were established at 0.1 (B4), 
0.25 (B3) and 0.5 (A3, A5, B1, B2 and C1) mg/kg. Twelve different samples were 
analyzed, comprising 4 crushed tomatoes, 4 fried tomatoes and 4 jam tomatoes. 
Calystegines A3 and B2 were identified in all the analyzed samples, while 
calystegine B3 was determined in all the fried tomatoes as well as in two 
crushed tomatoes and one jam tomato at concentrations ranging from 0.4 mg/kg 
(calystegine B2) to 19.0 mg/kg (calystegine A3). Although calystegine A5 was 
also detected in all the samples, only 3 of them gave concentrations higher than 
LOQ. Additionally, calystegine B1 was found in one jam tomato at 1.9 mg/kg.

Copyright © 2018 Elsevier B.V. All rights reserved.

DOI: 10.1016/j.chroma.2018.09.030
PMID: 30245074 [Indexed for MEDLINE]


3. Toxins (Basel). 2016 Mar 16;8(3):74. doi: 10.3390/toxins8030074.

Maternal Ingestion of Ipomoea carnea: Effects on Goat-Kid Bonding and Behavior.

Gotardo AT(1), Pfister JA(2), Raspantini PC(3), Górniak SL(4).

Author information:
(1)Research Center of Veterinary Toxicology (CEPTOX), Department of Pathology, 
School of Veterinary Medicine and Animal Science, University of São Paulo, 
Pirassununga 13635-900, Brazil. andregotardo@gmail.com.
(2)United States Department of Agriculture, Agricultural Research Service 
(USDA-ARS), Poisonous Plant Research Laboratory, 1150 E. 1400 N., Logan, UT 
84341, USA. jamesapfister@gmail.com.
(3)Research Center of Veterinary Toxicology (CEPTOX), Department of Pathology, 
School of Veterinary Medicine and Animal Science, University of São Paulo, 
Pirassununga 13635-900, Brazil. pcraspantini@gmail.com.
(4)Research Center of Veterinary Toxicology (CEPTOX), Department of Pathology, 
School of Veterinary Medicine and Animal Science, University of São Paulo, 
Pirassununga 13635-900, Brazil. gorniak@usp.br.

Ipomoea carnea is a toxic plant found in Brazil and other tropical and 
subtropical countries and often causes poisoning of livestock. The plant 
contains the alkaloids swainsonine and calystegines, which inhibit key cellular 
enzymes and cause systematic cell death. This study evaluated the behavioral 
effects of prenatal ingestion of this plant on dams and their kids. Twenty-four 
pregnant goats were randomly allocated into four treatment groups and received 
the following doses (g/kg BW) of fresh I. carnea: 0 (control group), 1.0 (IC1), 
3.0 (IC3), and 5.0 (IC5) from day 27 of gestation until parturition. Dam and kid 
bonding and behavior were evaluated by several tests, immediately after birth 
until six weeks of age. Dams from IC3 and IC5 groups spent less time paying 
attention to the newborn. There was a lack of maternal-infant bonding due to I. 
carnea intoxication. Kids from treated dams had difficulty in standing, 
suckling, and in recognizing their mother hours after birth. I. carnea can also 
compromise the kids' ability to learn and to retain spatial memory. We suggest 
that kids from pregnant goats given I. carnea during gestation have significant 
behavioral alterations and developmental delays that may compromise their 
survival.

DOI: 10.3390/toxins8030074
PMCID: PMC4810219
PMID: 26999204 [Indexed for MEDLINE]


4. Glycobiology. 1997 Dec;7(8):1085-8. doi: 10.1093/glycob/7.8.1085.

The effects of calystegines isolated from edible fruits and vegetables on 
mammalian liver glycosidases.

Asano N(1), Kato A, Matsui K, Watson AA, Nash RJ, Molyneux RJ, Hackett L, 
Topping J, Winchester B.

Author information:
(1)Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.

The polyhydroxylated nortropane alkaloids called calystegines occur in many 
plants of the Convolvulaceae, Solanaceae, and Moraceae families. Certain of 
these alkaloids exhibit potent inhibitory activities against glycosidases and 
the recently demonstrated occurrence of calystegines in the leaves, skins, and 
sprouts of potatoes (Solanum tuberosum), and in the leaves of the eggplant (S. 
melongena), has raised concerns regarding the safety of these vegetables in the 
human diet. We have surveyed the occurrence of calystegines in edible fruits and 
vegetables of the families Convolvulaceae, Solanaceae, and Moraceae by GC-MS. 
Calystegines A3, B1, B2, and C1 were detected in all the edible fruits and 
vegetables tested; sweet and chili peppers, potatoes, eggplants, tomatoes, 
Physalis fruits, sweet potatoes, and mulberries. Calystegines B1 and C1 were 
potent competitive inhibitors of the bovine, human, and rat beta-glucosidase 
activities, with Ki values of 150, 10, and 1.9 microM, respectively for B1 and 
15, 1.5, and 1 microM, respectively, for C1. Calystegine B2 was a strong 
competitive inhibitor of the alpha-galactosidase activity in all the livers. 
Human beta-xylosidase was inhibited by all four nortropanes, with calystegine C1 
having a Ki of 0.13 microM. Calystegines A3 and B2 selectively inhibited the rat 
liver beta-glucosidase activity. The potent inhibition of mammalian 
beta-glucosidase and alpha-galactosidase activities in vitro raises the 
possibility of toxicity in humans consuming large amounts of plants that contain 
these compounds.

DOI: 10.1093/glycob/7.8.1085
PMID: 9455909 [Indexed for MEDLINE]


5. Carbohydr Res. 1997 Nov 10;304(2):173-8. doi: 10.1016/s0008-6215(97)00227-9.

Enzymatic synthesis of the glycosides of calystegines B1 and B2 and their 
glycosidase inhibitory activities.

Asano N(1), Kato A, Kizu H, Matsui K, Griffiths RC, Jones MG, Watson AA, Nash 
RJ.

Author information:
(1)Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.

Several glycosides of calystegines B1 and B2 were synthesized by use of rice 
alpha-glucosidase and the whole cells of Rhodotorula lactosa, and their 
glycosidase inhibitory activities were investigated. Incubation of mixture of 
calystegine B1 and maltose with rice alpha-glucosidase gave 
3-O-alpha-D-glucopyranosylcalystegine B1 (2, 11.3%). An enzymatic 
beta-transglucosylation reaction of calystegines B1 or B2 with cellobiose using 
the whole cells of R. lactosa gave 3-O-beta-D-glucopyranosylcalystegine B1 (1) 
(0.9%) or 4-O-beta-D-glucopyranosylcalystegine B2 (3, 11.2%), respectively, 
while similar beta-transgalactosylation of calystegine B2 from lactose gave 
4-O-beta-D-galactopyranosylcalystegine B2 (4, 10.1%). The glycosylation of 
calystegines B1 and B2 markedly decreased or abolished their inhibition against 
beta-glucosidase, alpha- or beta-galactosidase. Compound 4 however retained more 
or less the potency of calystegine B2 against trehalase. Interestingly, compound 
1 was a noncompetitive inhibitor of rice alpha-glucosidase, with a Ki value of 
0.9 +/- 0.1 microM.

DOI: 10.1016/s0008-6215(97)00227-9
PMID: 9449768 [Indexed for MEDLINE]