integerrimine
senecionan-11,16-dione, 12-hydroxy-, (15E)- (9CI)
Identification
| Name | integerrimine |
| CAS Number | 480-79-5 |
| FDA UNII | 3179A6U4PN |
| Molecular Formula | C18 H25 N O5 |
| Molecular Weight | 335.40025000 |
| Nikkaji Number | J107.103C |
| Beilstein | 0934445 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 563.74 °C. @ 760.00 mm Hg (est) |
| Flash Point | 563.00 °F. TCC ( 294.70 °C. ) (est) |
| logP (o/w) | -1.504 (est) |
| Soluble in | water, 1.653e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 75 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 integerrimine usage levels up to | not for fragrance use. |
| Recommendation for integerrimine flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(15E)-12-
hydroxysenecionan-11,16-dione
inegerrimine
intergerrimine
senecionan-11,16-dione, 12-hydroxy-, (15E)- (9CI)
senecionin, (15E)-isomer
senecionine, (15E)-isomer
squalidin
squalidine
PubMed:
UPLC-MS/MS method for determination of selected pyrrolizidine alkaloids in feed.
PubMed:
Three new monoterpene glucosides from Senecio solidagineus.
PubMed:
Correction to Metabolomic and Genomic Evidence for Compromised Bile Acid Homeostasis by Senecionine, a Hepatotoxic Pyrrolizidine Alkaloid.
PubMed:
Toxicity of pyrrolizidine alkaloids to Spodoptera exigua using insect cell lines and injection bioassays.
PubMed:
Prenatal exposure to integerrimine N-oxide impaired the maternal care and the physical and behavioral development of offspring rats.
PubMed:
Mass-spectrometry-directed analysis and purification of pyrrolizidine alkaloid cis/trans isomers in Gynura japonica.
PubMed:
Metabolomic and genomic evidence for compromised bile acid homeostasis by senecionine, a hepatotoxic pyrrolizidine alkaloid.
PubMed:
[Determination of five pyrrolizidine alkaloids in honey by liquid chromatography-tandem mass spectrometry].
PubMed:
Tusanqi and hepatic sinusoidal obstruction syndrome.
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:
Assessment of pyrrolizidine alkaloid-induced toxicity in an in vitro screening model.
PubMed:
Analysis of pyrrolizidine alkaloids and evaluation of some biological activities of Algerian Senecio delphinifolius (Asteraceae).
PubMed:
The relationship between structurally different pyrrolizidine alkaloids and western flower thrips resistance in F(2) hybrids of Jacobaea vulgaris and Jacobaea aquatica.
PubMed:
Haematological and immunological effects of repeated dose exposure of rats to integerrimine N-oxide from Senecio brasiliensis.
PubMed:
[Simultaneous quantitation of adonifoline and senecionine in Senecio herbs by UPLC-MS].
PubMed:
Authentication of Senecio scandens and S. vulgaris based on the comprehensive secondary metabolic patterns gained by UPLC-DAD/ESI-MS.
PubMed:
The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS.
PubMed:
Hepatic sinusoidal obstruction syndrome associated with consumption of Gynura segetum.
PubMed:
The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury.
PubMed:
Chemical composition and antimicrobial activity of the essential oils from Cleome spinosa.
PubMed:
[Ethyl acetate-soluble chemical constituents from whole plants of Senecio chrysanthemoides].
PubMed:
Flavin-dependent monooxygenases as a detoxification mechanism in insects: new insights from the arctiids (lepidoptera).
PubMed:
Glucuronidation, a new metabolic pathway for pyrrolizidine alkaloids.
PubMed:
Identification of the UDP-glucuronosyltransferase isozyme involved in senecionine glucuronidation in human liver microsomes.
PubMed:
Pyrrolizidine alkaloids in pollen and pollen products.
PubMed:
Intracellular glutathione plays important roles in pyrrolizidine alkaloids-induced growth inhibition on hepatocytes.
PubMed:
Feeding deterrence and detrimental effects of pyrrolizidine alkaloids fed to honey bees (Apis mellifera).
PubMed:
Simultaneous determination of senecionine, adonifoline and their metabolites in rat serum by UPLC-ESIMS and its application in pharmacokinetic studies.
PubMed:
Determination of senkirkine and senecionine in Tussilago farfara using microwave-assisted extraction and pressurized hot water extraction with liquid chromatography tandem mass spectrometry.
PubMed:
Antitrypanosomal and cytotoxic activities of pyrrolizidine alkaloid-producing plants of Ethiopia.
PubMed:
Simultaneous characterization of pyrrolizidine alkaloids and N-oxides in Gynura segetum by liquid chromatography/ion trap mass spectrometry.
PubMed:
Safety assessment of food and herbal products containing hepatotoxic pyrrolizidine alkaloids: interlaboratory consistency and the importance of N-oxide determination.
PubMed:
Involvement of Bcl-xL degradation and mitochondrial-mediated apoptotic pathway in pyrrolizidine alkaloids-induced apoptosis in hepatocytes.
PubMed:
The toxicity of Senecio inaequidens DC.
PubMed:
Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang).
PubMed:
Identification and quantification of hepatotoxic pyrrolizidine alkaloids in the Ethiopian medicinal plant Solanecio gigas (Asteraceae).
PubMed:
Pyrrolizidine alkaloids of the endemic Mexican genus Pittocaulon and assignment of stereoisomeric 1,2-saturated necine bases.
PubMed:
Determination of pyrrolizidine alkaloids in senecio species by liquid chromatography/thermospray-mass spectrometry and liquid chromatography/nuclear magnetic resonance spectroscopy.
PubMed:
Pyrrolizidine alkaloid level in Senecio bicolor (Wilid.) Tod, ssp. cineraria (DC.) from middle Europe.
PubMed:
Dynamic pH junction-sweeping capillary electrophoresis for online preconcentration of toxic pyrrolizidine alkaloids in Chinese herbal medicine.
PubMed:
Do naïve ruminants degrade alkaloids in the rumen?
PubMed:
Acquisition, transformation and maintenance of plant pyrrolizidine alkaloids by the polyphagous arctiid Grammia geneura.
PubMed:
Separation and determination of toxic pyrrolizidine alkaloids in traditional Chinese herbal medicines by micellar electrokinetic chromatography with organic modifier.
PubMed:
Modeling K(m) values using electrotopological state: substrates for cytochrome P450 3A4-mediated metabolism.
PubMed:
Frequent gain and loss of pyrrolizidine alkaloids in the evolution of Senecio section Jacobaea (Asteraceae).
PubMed:
Specific recognition, detoxification and metabolism of pyrrolizidine alkaloids by the polyphagous arctiid Estigmene acrea.
PubMed:
Direct evidence for membrane transport of host-plant-derived pyrrolizidine alkaloid N-oxides in two leaf beetle genera.
PubMed:
Comparison of hepatic in vitro metabolism of the pyrrolizidine alkaloid senecionine in sheep and cattle.
PubMed:
Preventive activity of pyrrolizidine alkaloids from Seneciobrasiliensis (Asteraceae) on gastric and duodenal induced ulcer on mice and rats.
PubMed:
Modulation of gastrin and epidermal growth factor by pyrrolizidine alkaloids obtained from Senecio brasiliensis in acute and chronic induced gastric ulcers.
PubMed:
Differential metabolism of the pyrrolizidine alkaloid, senecionine, in Fischer 344 and Sprague-Dawley rats.
PubMed:
Acquired and partially de novo synthesized pyrrolizidine alkaloids in two polyphagous arctiids and the alkaloid profiles of their larval food-plants.
PubMed:
Variation in pyrrolizidine alkaloid patterns of Senecio jacobaea.
PubMed:
Evaporative light scattering detection of pyrrolizidine alkaloids.
PubMed:
Taste receptors for pyrrolizidine alkaloids in a monophagous caterpillar.
PubMed:
Pyrrolizidine alkaloids as oviposition stimulants for the cinnabar moth, Tyria jacobaeae.
PubMed:
Uptake and metabolism of pyrrolizidine alkaloids in Longitarsus flea beetles (Coleoptera: Chrysomelidae) adapted and non-adapted to alkaloid-containing host plants.
PubMed:
Biochemical strategy of sequestration of pyrrolizidine alkaloids by adults and larvae of chrysomelid leaf beetles.
PubMed:
Toxicity of Senecio vernalis to laying hens and evaluation of residues in eggs.
PubMed:
Toxic pyrrolyzidine alkaloids from three mongolian plants. a possible risk for cattle poisoning.
PubMed:
Pyrrolizidine alkaloid profiles of some Senecio species from Egypt.
PubMed:
Structure-activity relationships of pyrrolizidine alkaloids in insect chemical defense against the orb-weaving spider Nephila clavipes.
PubMed:
Simultaneous determination of N-oxides and free bases of pyrrolizidine alkaloids by cation-exchange solid-phase extraction and ion-pair high-performance liquid chromatography.
PubMed:
Alkaloids from Senecio aquaticus.
PubMed:
Evolutionary recruitment of a flavin-dependent monooxygenase for the detoxification of host plant-acquired pyrrolizidine alkaloids in the alkaloid-defended arctiid moth Tyria jacobaeae.
PubMed:
Induction of micronuclei by alkaloids extracted from Senecio brasiliensis and stored for 23 years.
PubMed:
Interplant alkaloid variation and Senecio vernalis toxicity in cattle.
PubMed:
Defensive chemistry of Senecio miser.
PubMed:
Variability in chemical constituents in Petasites hybridus from Austria.
PubMed:
SOS induction of selected naturally occurring substances in Escherichia coli (SOS chromotest).
PubMed:
Hepatotoxicity associated with pyrrolizidine alkaloid (Crotalaria spp) ingestion in a horse on Easter Island.
PubMed:
Species differences in the hepatic microsomal enzyme metabolism of the pyrrolizidine alkaloids.
PubMed:
[Veno-occlusive disease after prolonged treatment with senecionine (Hemoluol)].
PubMed:
The roles of CYP3A and CYP2B isoforms in hepatic bioactivation and detoxification of the pyrrolizidine alkaloid senecionine in sheep and hamsters.
PubMed:
Generation and characterization of monoclonal antibodies against the pyrrolizidine alkaloid retrorsine.
PubMed:
Determination of pyrrolizidine alkaloids in honey from selected sites by solid phase extraction and HPLC-MS.
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:
Recombinagenic activity of integerrimine, a pyrrolizidine alkaloid from Senecio brasiliensis, in somatic cells of Drosophila melanogaster.
PubMed:
Pyrrolizidine alkaloids from Gynura divaricata.
PubMed:
A competitive enzyme immunoassay for the pyrrolizidine alkaloids of the senecionine type.
PubMed:
Preparative separation of pyrrolizidine alkaloids by high-speed counter-current chromatography.
PubMed:
Enzyme-linked immunosorbent assay detection of pyrrolizidine alkaloids: immunogens based on quaternary pyrrolizidinium salts.
PubMed:
Pyrrolizidine alkaloids of three species of senecio in British Columbia.
PubMed:
A cytochrome P4502B form is the major bioactivation enzyme for the pyrrolizidine alkaloid senecionine in guinea pig.
PubMed:
Analysis of pyrrolizidine alkaloids: a competitive enzyme-linked immunoassay (ELISA) for the quantitative determination of some toxic pyrrolizidine alkaloids.
PubMed:
The effect of spironolactone treatment on the cytochrome P450-mediated metabolism of the pyrrolizidine alkaloid senecionine by hepatic microsomes from rats and guinea pigs.
PubMed:
Hepatotoxic pyrrolizidine alkaloids in the Mexican medicinal plant Packera candidissima (Asteraceae: Senecioneae).
PubMed:
Differing embryotoxic effects of senecionine and senecionine-N-oxide on the chick embryo.
PubMed:
Structural influences on pyrrolizidine alkaloid-induced cytopathology.
PubMed:
Pyrrolizidine alkaloids from Senecio leucanthemifolius and Senecio rodriguezii.
PubMed:
Microsomal formation of a pyrrolic alcohol glutathione conjugate of the pyrrolizidine alkaloid senecionine.
PubMed:
Hydrolysis of pyrrolizidine alkaloids by guinea pig hepatic carboxylesterases.
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:
Pyrrolizidine alkaloids from Werneria nubigena.
PubMed:
Pyrrolizidine alkaloids from Melampyrum pratense.
PubMed:
Sequestration of ingested [(14)C]senecionineN-oxide in the exocrine defensive secretions of chrysomelid beetles.
PubMed:
DNA cross-linking in mammalian cells by pyrrolizidine alkaloids: structure-activity relationships.
PubMed:
Flavin-containing monooxygenase: a major detoxifying enzyme for the pyrrolizidine alkaloid senecionine in guinea pig tissues.
PubMed:
Role of cytochrome P450IIIA4 in the metabolism of the pyrrolizidine alkaloid senecionine in human liver.
PubMed:
Mechanisms for pyrrolizidine alkaloid activation and detoxification.
PubMed:
Excretion and blood radioactivity levels following [14C]senecionine administration in the rat.
PubMed:
N-acetylcysteine-conjugated pyrrole identified in rat urine following administration of two pyrrolizidine alkaloids, monocrotaline and senecionine.
PubMed:
The effect of the pyrrolizidine alkaloid integerrimine on the chromosomes of mouse bone marrow cells.
PubMed:
Honeydew analysis for detecting phloem transport of plant natural products : Implications for host-plant resistance to sap-sucking insects.
PubMed:
[Studies on the alkaloids of Gynura segetum (Lour.) Merr].
PubMed:
Pyrrolizidine alkaloids in Senecio vulgaris L. growing in Iceland.
PubMed:
Bioactivation and detoxication of the pyrrolizidine alkaloid senecionine by cytochrome P-450 enzymes in rat liver.
PubMed:
The role of flavin-containing monooxygenase in the N-oxidation of the pyrrolizidine alkaloid senecionine.
PubMed:
Human embryotoxicity of pyrrolizidine-containing drugs.
PubMed:
Effects of the pyrrolizidine alkaloid senecionine and the alkenals trans-4-OH-hexenal and trans-2-hexenal on intracellular calcium compartmentation in isolated hepatocytes.
PubMed:
Sites of synthesis, translocation and accumulation of pyrrolizidine alkaloid N-oxides in Senecio vulgaris L.
PubMed:
Alkaloid N-oxides as transport and vacuolar storage compounds of pyrrolizidine alkaloids in Senecio vulgaris L.
PubMed:
Metabolic links between the biosynthesis of pyrrolizidine alkaloids and polyamines in root cultures of Senecio vulgaris.
PubMed:
Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography.
PubMed:
Identification of senecionine and senecionine N-oxide as antifertility constituents in Senecio vulgaris.
PubMed:
Determination of pyrrolizidine alkaloid metabolites from mouse liver microsomes using tandem mass spectrometry and gas chromatography/mass spectrometry.
PubMed:
Hepatic veno-occlusive disease in newborn infant of a woman drinking herbal tea.
PubMed:
Livestock poisoning in South America by species of the Senecio plant.
PubMed:
Species differences in the hepatic microsomal metabolism of the pyrrolizidine alkaloid senecionine.
PubMed:
Alkaloid patterns and biosynthetic capacity of root cultures from some pyrrolizidine alkaloid producing Senecio species.
PubMed:
Lipid peroxidation and cellular damage caused by the pyrrolizidine alkaloid senecionine, the alkenal trans-4-hydroxy-2-hexenal, and related alkenals.
PubMed:
Toxic actions of senaetnine, a new pyrrolizidine-type alkaloid, in rats.
PubMed:
Microsomal metabolism of pyrrolizidine alkaloids: N-oxidation of seneciphylline and senecionine.
PubMed:
[Solvent extraction and isolation of alkaloids A and B from Senecio fuberi].
PubMed:
Metabolism and toxicity of anacrotine, a pyrrolizidine alkaloid, in rats.
PubMed:
Role of cellular calcium homeostasis in toxic liver injury induced by the pyrrolizidine alkaloid senecionine and the alkenal trans-4-OH-2-hexenal.
PubMed:
Microsomal metabolism of pyrrolizidine alkaloids from Senecio jacobaea. Isolation and quantification of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine and N-oxides by high performance liquid chromatography.
PubMed:
Genotoxicity and cytotoxicity of selected pyrrolizidine alkaloids, a possible alkenal metabolite of the alkaloids, and related alkenals.
PubMed:
Formation of cyclic adducts of deoxyguanosine with the aldehydes trans-4-hydroxy-2-hexenal and trans-4-hydroxy-2-nonenal in vitro.
PubMed:
Selective uptake of pyrrolizidine N-oxides by cell suspension cultures from pyrrolizidine alkaloid producing plants.
PubMed:
The formation of 6,7-dihydro-7-hydroxy-1-hydroxy-methyl-5H-pyrrolizine, a metabolite of pyrrolizidine alkaloids.
PubMed:
Method for determination of pyrrolizidine alkaloids and their metabolites by high-performance liquid chromatography.
PubMed:
Determination of pyrrolizidine alkaloids in Senecio inaequidens D.C. by capillary gas chromatography.
PubMed:
In vivo covalent binding of trans-4-hydroxy-2-hexenal to rat liver macromolecules.
PubMed:
Comparative cytopathology of primary rat hepatocyte cultures exposed to aflatoxin B1, acetaminophen, and other hepatotoxins.
PubMed:
trans-4-Hydroxy-2-hexenal: a reactive metabolite from the macrocyclic pyrrolizidine alkaloid senecionine.
PubMed:
Initiation and selection of resistant hepatocyte nodules in rats given the pyrrolizidine alkaloids lasiocarpine and senecionine.
PubMed:
Genotoxicity of a variety of pyrrolizidine alkaloids in the hepatocyte primary culture-DNA repair test using rat, mouse, and hamster hepatocytes.
PubMed:
In vivo covalent binding of retronecine-labelled [3H]seneciphylline and [3H]senecionine to DNA of rat liver, lung and kidney.
PubMed:
Effect of seneciphylline and senecionine on hepatic drug metabolizing enzymes in rats.
PubMed:
Senecionine from Gynura segetum.
PubMed:
New guaianolides from Centaurea kandavanensis.
PubMed:
Influences of various xenobiotic inducers on cytocidal toxicity of lasiocarpine and senecionine in primary cultures of rat hepatocytes.
PubMed:
Two dihydropyrrolizine alkaloid metabolites isolated from mouse hepatic microsomes in vitro.
PubMed:
Transfer of [3H]pyrrolizidine alkaloids from Senecio vulgaris L. and metabolites into rat milk and tissues.
PubMed:
Comparison of the toxicities of Senecio jacobaea, Senecio vulgaris and Senecio glabellus in rats.
PubMed:
A new pyrrolizidine alkaloid metabolite, 19-hydroxysenecionine isolated from mouse hepatic microsomes in vitro.
PubMed:
Covalent binding of two pyrrolizidine alkaloids, senecionine and seneciphylline, to hepatic macromolecules and their distribution, excretion, and transfer into milk of lactating mice.
PubMed:
Carcinogenic and mutagenic activity of an alkaloidal extract of Senecio nemorensis ssp. fuchsii.
PubMed:
Alkaloids from Senecio aegyptius and S. desfontainei.
PubMed:
Metabolism, cytotoxicity, and genotoxicity of the pyrrolizidine alkaloid senecionine in primary cultures of rat hepatocytes.
PubMed:
Effects of the pyrrolizidine alkaloids senecionine, retrorsine and seneciphylline on aminopyrine N-demethylase activity on the rat liver S-10 fraction.
PubMed:
[On the gas-chromatographical determination of the pyrrolizidine alkaloids of some Senecio-species].
PubMed:
[Spasmolytic properties of pyrrolizidine alkaloids].
PubMed:
Pyrrolizidine alkaloids: their occurrence in honey from tansy ragwort (Senecio jacobaea L.)
PubMed:
Hepato- and pneumotoxicity of pyrrolizidine alkaloids and derivatives in relation to molecular structure.
PubMed:
Senecionine, Seneciphylline, Jacobine and Otosenine from Senecio cineraria.
PubMed:
Pyrrolizidine alkaloid biosynthesis. Relative rates of incorporation of the isomers of isoleucine into the necic acid component of senecionine.
PubMed:
[Various biochemical changes in the rat liver following acute senecionine poisoning. I. Changes in content of reduced glutathione, plasma proteins and bilirubin].
PubMed:
Pyrrolizidine alkaloids: actions on muscarinic receptors in the guinea-pig ileum.
PubMed:
Pharmacological properties of integerrimine, an alkaloid isolated from Crotalaria brevifolia.
PubMed:
Tumor inhibitors. XXII. Senecionine and senecionine N-oxide, the active principles of Senecio triangularis.
PubMed:
The action of alloxan, senecionine, sulfadiazine, and thiouracil in the hamster.
PubMed:
The effects of senecionine on the monkey.
PubMed:
Effects of senecionine on the hamster and monkey.