Integerrimine N-oxideCAS# 85955-28-8 |
- Senecionine N-oxide
Catalog No.:BCN2130
CAS No.:13268-67-2
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 85955-28-8 | SDF | Download SDF |
PubChem ID | 6437374 | Appearance | White-yellowish powder |
Formula | C18H25NO6 | M.Wt | 351.4 |
Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
Synonyms | Squalidine N-oxide | ||
Solubility | Soluble in chloroform and ethan | ||
Chemical Name | (1R,4E,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione | ||
SMILES | CC=C1CC(C(C(=O)OCC2=CC[N+]3(C2C(CC3)OC1=O)[O-])(C)O)C | ||
Standard InChIKey | PLGBHVNNYDZWGZ-NRTYDQPPSA-N | ||
Standard InChI | InChI=1S/C18H25NO6/c1-4-12-9-11(2)18(3,22)17(21)24-10-13-5-7-19(23)8-6-14(15(13)19)25-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4+/t11-,14-,15-,18-,19?/m1/s1 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Integerrimine N-oxide Dilution Calculator
Integerrimine N-oxide Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 2.8458 mL | 14.2288 mL | 28.4576 mL | 56.9152 mL | 71.144 mL |
5 mM | 0.5692 mL | 2.8458 mL | 5.6915 mL | 11.383 mL | 14.2288 mL |
10 mM | 0.2846 mL | 1.4229 mL | 2.8458 mL | 5.6915 mL | 7.1144 mL |
50 mM | 0.0569 mL | 0.2846 mL | 0.5692 mL | 1.1383 mL | 1.4229 mL |
100 mM | 0.0285 mL | 0.1423 mL | 0.2846 mL | 0.5692 mL | 0.7114 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- Heliotridine
Catalog No.:BCN8929
CAS No.:520-63-8
- Erucifolin N-oxide
Catalog No.:BCN8928
CAS No.:123864-94-8
- 19-O-beta-D-carboxyglucopyranosyl-12-O-beta-D-glucopyranosyl-11,16-dihydroxyabieta-8,11,13-triene
Catalog No.:BCN8926
CAS No.:1011714-20-7
- Nardoaristolone B
Catalog No.:BCN8925
CAS No.:1422517-82-5
- (3R,5S,E)-1,7-Diphenylhept-1-ene-3,5-diol
Catalog No.:BCN8924
CAS No.:232261-31-3
- (3S,5S,E)-1,7-Diphenylhept-1-ene-3,5-diol
Catalog No.:BCN8923
CAS No.:87095-75-8
- 5-Hydroxy-7,8-dimethoxy (2R)-flavanone-5-O-beta-D-glucopyranoside
Catalog No.:BCN8922
CAS No.:942626-74-6
- (1E)-3-methoxy-8,12-epoxygermacra-1,7,10,11-tetraen-6-one
Catalog No.:BCN8921
CAS No.:1393342-06-7
- Ginsenoside MC
Catalog No.:BCN8920
CAS No.:175484-06-7
- 3-Hydroxy-4',5-dimethoxystilbene
Catalog No.:BCN8919
CAS No.:58436-29-6
- Isoeuphorbetin
Catalog No.:BCN8918
CAS No.:50677-55-9
- Licoflavanone
Catalog No.:BCN8917
CAS No.:119240-82-3
- Intermedine N-oxide
Catalog No.:BCN8931
CAS No.:95462-14-9
- Jacobine N-oxide
Catalog No.:BCN8932
CAS No.:38710-25-7
- Merenskine
Catalog No.:BCN8933
CAS No.:96657-94-2
- Merenskine N-oxide
Catalog No.:BCN8934
CAS No.:96657-95-3
- 7-O-Acetyllycopsamine N-oxide
Catalog No.:BCN8935
CAS No.:685132-58-5
- Riddelline N-oxide
Catalog No.:BCN8936
CAS No.:75056-11-0
- Senecivernine N-oxide
Catalog No.:BCN8937
CAS No.:101687-28-9
- Sceleratine N-oxide
Catalog No.:BCN8938
CAS No.:103184-92-5
- Glucohesperin
Catalog No.:BCN8939
CAS No.:33049-17-1
- 6-Hydroxytropinone
Catalog No.:BCN8940
CAS No.:5932-53-6
- Glucoraphenin
Catalog No.:BCN8942
CAS No.:108844-81-1
- Heliosupine N-oxide
Catalog No.:BCN8943
CAS No.:31701-88-9
Pyrrolizidine alkaloid variation in Senecio vulgaris populations from native and invasive ranges.[Pubmed:28828276]
PeerJ. 2017 Aug 14;5:e3686.
Biological invasion is regarded as one of the greatest environmental problems facilitated by globalization. Some hypotheses about the invasive mechanisms of alien invasive plants consider the plant-herbivore interaction and the role of plant defense in this interaction. For example, the "Shift Defense Hypothesis" (SDH) argues that introduced plants evolve higher levels of qualitative defense chemicals and decreased levels of quantitative defense, as they are released of the selective pressures from specialist herbivores but still face attack from generalists. Common groundsel (Senecio vulgaris), originating from Europe, is a cosmopolitan invasive plant in temperate regions. As in other Senecio species, S. vulgaris contains pyrrolizidine alkaloids (PAs) as characteristic qualitative defense compounds. In this study, S. vulgaris plants originating from native and invasive ranges (Europe and China, respectively) were grown under identical conditions and harvested upon flowering. PA composition and concentration in shoot and root samples were determined using Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS). We investigated the differences between native and invasive S. vulgaris populations with regard to quantitative and qualitative variation of PAs. We identified 20 PAs, among which senecionine, senecionine N-oxide, Integerrimine N-oxide and seneciphylline N-oxide were dominant in the roots. In the shoots, in addition to the 4 PAs dominant in roots, retrorsine N-oxide, spartioidine N-oxide and 2 non-identified PAs were also prevalent. The roots possessed a lower PA diversity but a higher total PA concentration than the shoots. Most individual PAs as well as the total PA concentration were strongly positively correlated between the roots and shoots. Both native and invasive S. vulgaris populations shared the pattern described above. However, there was a slight trend indicating lower PA diversity and lower total PA concentration in invasive S. vulgaris populations than native populations, which is not consistent with the prediction of SDH.
Prenatal exposure to integerrimine N-oxide enriched butanolic residue from Senecio brasiliensis affects behavior and striatal neurotransmitter levels of rats in adulthood.[Pubmed:26416213]
Int J Dev Neurosci. 2015 Dec;47(Pt B):157-64.
Pyrrolizidine alkaloids (PAs) are toxins that are exclusively biosynthesized by plants and are commonly present in foods and herbs. PAs are usually associated with poisoning events in livestock and human beings. The aim of the present study was to evaluate the behavioral and neurochemical effects of prenatal exposure to PA Integerrimine N-oxide of rats in adulthood. Pregnant Wistar rats received Integerrimine N-oxide from the butanolic residue of Senecio brasiliensis by gavage on gestational days 6-20 at doses of 3, 6 and 9 mg/kg. During adulthood of the offspring, the following behavioral tests were performed: open-field, plus-maze, forced swimming, catalepsy and stereotypy. Histological analyses and monoamine levels were measured. Male offspring from dams that were exposed to 9 mg/kg showed an increase in locomotion in the open-field test, an increased frequency of entries and time spent in open arms in elevated plus-maze test, as well as decreased swimming time. In the female offspring from dams that were exposed to 9 mg/kg, there was an increased time of climbing in forced swimming and intensity of stereotyped behavior. The histological study indicates an increase in the number of multinucleated cells in the liver (6 and 9 mg/kg). In neurotransmitter analysis, specifically in the striatum, we observed change in dopamine and serotonin levels in the middle dose. Thus, our results indicate that prenatal exposure to Integerrimine N-oxide changed behavior in adulthood and neurotransmitter levels in the striatum. Our results agree with previous studies, which showed that Integerrimine N-oxide impaired physical and neurobehavioral development in childhood that can persist until adulthood.
Prenatal exposure to integerrimine N-oxide impaired the maternal care and the physical and behavioral development of offspring rats.[Pubmed:24881561]
Int J Dev Neurosci. 2014 Aug;36:53-63.
Plants that contain pyrrolizidine alkaloids (PAs) have been reported as contaminants of pastures and food, as well as being used in herbal medicine. PAs are responsible for poisoning events in livestock and human beings. The aim of this present study was to evaluate effects of prenatal exposure to Integerrimine N-oxide, the main PA found in the butanolic residue (BR) of Senecio brasiliensis, on both physical and behavioral parameters of Wistar rat offspring. The toxicity and maternal behavior were also evaluated. For this, pregnant Wistar rats received Integerrimine N-oxide from the BR of Senecio brasiliensis, by gavage, on gestational days 6-20 (during organogenesis and fetal development period) at doses of 3, 6 and 9 mg/kg. During treatment, maternal body weight gain, and food and water intake were evaluated. After parturition, maternal behavior and aggressive maternal behavior were analyzed. In addition, physical development and behavioral assessments were observed in both male and female pups. Results showed that prenatal exposure to Integerrimine N-oxide of S. brasiliensis induced maternal toxicity, impairment in maternal behavior and aggressive maternal behavior, mainly in the highest dose group. Between sexes comparison of pups showed loss of body weight, delayed physical development such as pinna detachment, hair growth, eruption of incisor teeth, eye and vaginal openings. These pups also showed a delay of palmar grasp, surface righting reflex, negative geotaxis and auditory startle reflexes. Thus, prenatal exposure to Integerrimine N-oxide induces maternal toxicity, impairment of maternal care and delayed in physical and behavioral development of the offspring.