heliotrine
butanoic acid, 2-hydroxy-3-methoxy-2-(1-methylethyl)-, [(1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3R)-
Identification
| Name | heliotrine |
| CAS Number | 303-33-3 |
| FDA UNII | ZYB88Y4FUZ |
| Molecular Formula | C16 H27 N O5 |
| Molecular Weight | 313.39419000 |
| MDL Number | MFCD00213991 |
| Nikkaji Number | J4.476H |
| Beilstein | 0292841 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 4.635e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mammal (species unspecified) LDLo 250 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for heliotrine usage levels up to | not for fragrance use. |
| Recommendation for heliotrine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
butanoic acid, 2-hydroxy-3-methoxy-2-(1-methylethyl)-, [(1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3R)-
[(7S,8R)-7-
hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
PubMed:
Pyrrolizidine alkaloids in food and feed on the Belgian market.
PubMed:
Utility of an appropriate reporter assay: Heliotrine interferes with GAL4/upstream activation sequence-driven reporter gene systems.
PubMed:
Disturbance of gene expression in primary human hepatocytes by hepatotoxic pyrrolizidine alkaloids: A whole genome transcriptome analysis.
PubMed:
Characterization and screening of pyrrolizidine alkaloids and N-oxides from botanicals and dietary supplements using UHPLC-high resolution mass spectrometry.
PubMed:
An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides.
PubMed:
Heliotropium europaeum poisoning in cattle and analysis of its pyrrolizidine alkaloid profile.
PubMed:
Reaction of dehydropyrrolizidine alkaloids with valine and hemoglobin.
PubMed:
Structure-activity relationship in the passage of different pyrrolizidine alkaloids through the gastrointestinal barrier: ABCB1 excretes heliotrine and echimidine.
PubMed:
Development and validation of a rapid multiplex ELISA for pyrrolizidine alkaloids and their N-oxides in honey and feed.
PubMed:
Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity.
PubMed:
Pyrrolizidine alkaloids: their occurrence in Spanish honey collected from purple viper's bugloss (Echium spp.).
PubMed:
Comparison of metabolism-mediated effects of pyrrolizidine alkaloids in a HepG2/C3A cell-S9 co-incubation system and quantification of their glutathione conjugates.
PubMed:
[Morphologic characteristic of chronic toxic hepatitis for treatment with Neoselen].
PubMed:
Pyrrolizidine alkaloids in honey: risk analysis by gas chromatography-mass spectrometry.
PubMed:
Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine.
PubMed:
Major components in the hairpencil secretion of a butterfly, Euploea mulciber (Lepidoptera, Danaidae): their origins and male behavioral responses to pyrrolizidine alkaloids.
PubMed:
Final report of the safety assessment of niacinamide and niacin.
PubMed:
Differential utilization of pyrrolizidine alkaloids by males of a danaid butterfly, Parantica sita, for the production of danaidone in the alar scent organ.
PubMed:
[Effect of maternal toxic hepatitis on the functional characteristics of the lactation process].
PubMed:
[Experimental and clinical evaluation of the efficacy of ecdysten in the treatment of hepatitis].
PubMed:
Evaporative light scattering detection of pyrrolizidine alkaloids.
PubMed:
[Morphological characteristics of chronic toxic hepatitis treated with neoselen].
PubMed:
Taste receptors for pyrrolizidine alkaloids in a monophagous caterpillar.
PubMed:
Pyrrolizidine alkaloids as oviposition stimulants for the cinnabar moth, Tyria jacobaeae.
PubMed:
Toxicity of dietary Heliotropium circinatum to rats.
PubMed:
Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi.
PubMed:
Metabolism of pyrrolizidine alkaloids by Peptostreptococcus heliotrinreducens and a mixed culture derived from ovine ruminal fluid.
PubMed:
[Effects of maternal toxic hepatitis on the postnatal development of duodenal morphology of their offspring].
PubMed:
[Correction of the lipid composition of the liver plasma membranes during heliotrine intoxication].
PubMed:
[Some aspects of the formation of the immune system organs in newborn rats born to females with chronic hepatitis].
PubMed:
Toxicity of dietary Heliotropium dolosum seed to mice.
PubMed:
[The effect of perftoran on the biochemical detoxication parameters in rats with an acute toxic lesion of the liver].
PubMed:
[Thymus changes in chronic heliotrine-induced hepatitis].
PubMed:
The two facies of pyrrolizidine alkaloids: the role of the tertiary amine and its N-oxide in chemical defense of insects with acquired plant alkaloids.
PubMed:
[Enzymatic activity of the pancreas and small intestinal mucosa in modelling of toxic hepatitis by administration of heliotrine].
PubMed:
Sequestration of pyrrolizidine alkaloids in several arctiid moths (Lepidoptera: Arctiidae).
PubMed:
Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae).
PubMed:
[Mechanism of the damaging effect of heliotrine on the functional and metabolic parameters of hepatocytes].
PubMed:
Micronuclei in adult and foetal mice exposed in vivo to heliotrine, urethane, monocrotaline and benzidine.
PubMed:
Detection of sulphur-conjugated pyrrolic metabolites in blood and fresh or fixed liver tissue from rats given a variety of toxic pyrrolizidine alkaloids.
PubMed:
A potential kairomone stimulates pheromone-responsive receptor neurons inUtetheisa ornatrix (Lepidoptera: Arctiidae).
PubMed:
Chemistry of sulphur-bound pyrrolic metabolites in the blood of rats given different types of pyrrolizidine alkaloid.
PubMed:
[Change in lipid peroxidation processes and level of individual gangliosides and phospholipids in the liver of rats with toxic experimental hepatitis].
PubMed:
Identity of a biliary metabolite formed from monocrotaline in isolated, perfused rat liver.
PubMed:
Disturbances in oxidative phosphorylation in the liver of rats with heliotrine-induced hepatitis and restoration by phosphatidylcholine and ATP.
PubMed:
[Reparation of the hepatocyte plasma membrane using phosphatidylcholine liposomes].
PubMed:
Model systems for detecting the hepatic toxicity of pyrrolizidine alkaloids and pyrrolizidine alkaloid N-oxides.
PubMed:
Pyrrolizidine alkaloids from Heliotropium rotundifolium.
PubMed:
The fetal blood erythrocyte micronucleus assay: classification of RNA-positive erythrocytes into two age populations by RNA aggregation state.
PubMed:
[Features of protein secretion by the rat liver in various stages of carbon tetrachloride or heliotrine poisoning].
PubMed:
Somatic mutation induced by heliotrine in Drosophila.
PubMed:
[Phosphatidylcholine-induced repair of damaged hepatocyte membranes in heliotrine poisoning].
PubMed:
[Phospholipid composition and oxidative phosphorylation in liver mitochondria in hepatitis].
PubMed:
[Action of phytoecdysteroids on the bile-secretory function of the normal liver and in experimental hepatitis].
PubMed:
[Causes of hyperinsulinemia and decreased sensitivity to insulin in liver damage].
PubMed:
Pheromones of two arctiid moths (Creatonotos transiens andC. gangis) : Chiral components from both sexes and achiral female components.
PubMed:
[Functional state of the hepatocyte cytoplasmic network in heliotrine injury of the rat liver].
PubMed:
Induction of SCEs by some pyrrolizidine alkaloids in V79 Chinese hamster cells co-cultured with chick embryo hepatocytes.
PubMed:
Poisonous plants contaminating edible ones and toxic substances in plant foods. Part 3. Pyrrolizidine alkaloids from Heliotropium digynum Forssk. (= H. luteum, Poir.).
PubMed:
Stereochemical course of pheromone biosynthesis in the arctiid moth, Creatonotos transiens.
PubMed:
A Note on "Isolation and Pharmacological Action of Heliotrine, the Major Alkaloid of Heliotropium indicum Seeds".
PubMed:
[State of oxidizing processes in rat liver in chronic heliotrine hepatitis].
PubMed:
[Influence of heliotrin on the rat liver microsomal oxidation system].
PubMed:
Isolation and pharmacological action of heliotrine, the major alkaloid of Heliotropium indicum seeds.
PubMed:
Somatic and teratogenic effects induced by heliotrine in Drosophila.
PubMed:
[Characteristics of the course of viral hepatitis B in patients with concomitant diseases treated with glucocorticosteroids].
PubMed:
Heliotrine poisoning of broiler chickens: an experimental clinicopathologic study of low dose intoxication.
PubMed:
[Electrolyte effect on heliotrine and lasiocarpine extraction with organic solvents].
PubMed:
[On the gas-chromatographical determination of the pyrrolizidine alkaloids of some Senecio-species].
PubMed:
Anticancer drug testing in vitro: use of an activating system with the human tumor stem cell assay.
PubMed:
Comparison of the toxic effects of dehydroheliotridine and heliotrine in pregnant rats and their embryos.
PubMed:
Chromosomal aberrations and mutation in cultured mammalian cells induced by pyrrolizidine alkaloids.
PubMed:
Direct quantitative analysis of indicine-N-oxide in cancer patient samples by gas chromatography using the internal standard heliotrine-N-oxide including a mass spectral comparison of their trimethylsilyl derivatives.
PubMed:
Mutagenicity of pyrrolizidine alkaloids in the Salmonella/mammalian-microsome test.
PubMed:
Poisoning of chickens and ducks by pyrrolizidine alkaloids of Heliotropium europaeum.
PubMed:
Relationship of the reductive metabolism of indicine N-oxide to its antitumor activity.
PubMed:
The gas chromatographic mass spectrometric analysis of the new antitumor drug indicine-N-oxide utilizing a novel reaction accompanying trimethylsilylation.
PubMed:
An epidemic of veno-occlusive disease of the liver in Afghanistan. Pathologic features.
PubMed:
Herbal medicines and veno-occlusive disease in India.
PubMed:
The role of nicotinamide and of certain other modifying factors in diethylnitrosamine carcinogenesis: fusaria mycotoxins and "spontaneous" tumors in animals and man.
PubMed:
[Interrelationship between the structure, microcirculation and tissue-vascular permeability of the liver after experimental toxic damage].
PubMed:
The effects of the pyrrolizidine alkaloid, heliotrine, and nicotinamide on the concentration of plasma insulin and blood glucose in the rat.
PubMed:
Pancreatic islet-cell and other tumors in rats given heliotrine, a monoester pyrrolizidine alkaloid, and nicotinamide.
PubMed:
Use of repair-deficient strains of Escherichia coli and liver microsomes to detect and characterise DNA damage caused by pyrrolizidine alkaloids heliotrine and monocrotaline.
PubMed:
Decreased synthesis of hepatic satellite DNA in pyrrolizidine alkaloidosis of the sheep.
PubMed:
Proceedings: Pancreatic islet cell and other tumours induced in rats by heliotrine- a mono-ester pyrrolizidine alkaloid; the effects of additional treatment with nicotinamide.
PubMed:
An analysis of chromosomal sensitivity of HPK1 cells from the marsupial Potorous tridactylus to x-rays and to heliotrine.
PubMed:
Pyrrolizidine alkaloids: actions on muscarinic receptors in the guinea-pig ileum.
PubMed:
[Study of the action of oxido-reductive enzymes in the liver of rats with chronic heliotrine poisoning].
PubMed:
Comparison of the effects of LSD, heliotrine and x-irradiation on chromosome breakage, and the effects of LSD on the rate of cell division.
PubMed:
The effect of heliotrine, a pyrrolizidine alkaloid, on human liver cells in culture.
PubMed:
The mutagenic activity of the pyrrolizidine alkaloid heliotrine in Drosophila melanogaster. II. Chromosome rearrangements.
PubMed:
Excretion of the pyrrolizidine alkaloid heliotrine in the urine and bile of sheep.
PubMed:
An electron microscopic study of giant cytosegresomes in acute liver injury due to heliotrine.
PubMed:
[Hematopoiesis in chronic heliotrine poisoning in Wistar albino rats].
PubMed:
An electron-microscope study of liver cell necrosis due to heliotrine.
PubMed:
[Morphologic signs of the participation of immunologic mechanisms in the pathogenesis of heliotrine liver cirrhosis (experimental-morphologic study)].
PubMed:
[Morphologic and histochemical changes in the rat liver after administration of heliotrine].
PubMed:
Reduction of heliotrine by a rumen microorganism.
PubMed:
[Phagocytosis of erythroblasts by bone marrow reticular cells in rats with chronic heliotrine poisoning].
PubMed:
Effects of the pyrrolizidine alkaloid heliotrine on cell division and chromosome breakage in cultures of leucocytes from the marsupial Potorous tridactylus.
PubMed:
Lysosome changes in acute liver injury due to heliotrine.
PubMed:
The mutagenic activity of heliotrine in Drosophila. I. Complete and mosaic sex-linked lethals.
PubMed:
THE EFFECT OF CYANIDE AND AZIDE ON THE MUTAGENIC ACTIVITY OF THE PYRROLIZIDINE ALKALOID HELIOTRINE IN DROSOPHILA MELANOGASTER.
PubMed:
Acute toxic liver injury. nicotinamide-adenine dinucleotide-pyrophosphorylase activity of nuclei isolated from rat liver in heliotrine and in dimethylnitrosamine poisoning.
PubMed:
Liver damage in acute heliotrine poisoning. 1. The intracellular distribution of pyridine nucleotides.
PubMed:
Liver damage in acute heliotrine poisioning. 2. The effect of nicotinamide on pyridine nucleotide concentrations.
PubMed:
Malformations in foetal rats induced by the pyrrolizidine alkaloid, heliotrine.
PubMed:
Pyridine nucleotide metabolism in heliotrine poisoning.
PubMed:
The chronic pathological effects on the liver of the rat of the pyrrolizidine alkaloids heliotrine, lasiocarpine, and their N-oxides.
PubMed:
Mutagenic activity of the alkaloid heliotrine in Drosophila.
PubMed:
The acute toxic effects of heliotrine and lasiocarpine, and their N-oxides, on the rat.
PubMed:
Hepatotoxic and pharmacologic properties of heliotrine.