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1. Integerrimine
2. Intergerrimine
3. Senecionine Citrate (1:1)
4. Senecionine Citratre
5. Senecionine, (15e)-isomer
6. Squalidine
1. Aureine
2. 130-01-8
3. Senecionin
4. 12-hydroxysenecionan-11,16-dione
5. Chebi:9107
6. Senecionan-11,16-dione, 12-hydroxy-
7. Bo6n1u5yg6
8. [1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3z,5r,6r,14ar,14br)-
9. Nsc89935
10. Nsc-89935
11. (1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3z,5r,6r,14ar,14br)-
12. Senecionine, Analytical Standard
13. [1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione,3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-,(3z,5r,6r,14ar,14br)-
14. Ccris 4340
15. Hsdb 3535
16. Nsc 89935
17. Unii-bo6n1u5yg6
18. Brn 0934445
19. Ai3-51771
20. Senecionine [mi]
21. (-)-senecionine
22. Schembl896098
23. Senecionan-11, 12-hydroxy-
24. Chembl362153
25. Dtxsid40871615
26. Senecionine, >=95.0% (gc)
27. Hy-n2560
28. Bdbm50480301
29. Mfcd00221720
30. Zinc95851257
31. Akos037514834
32. Ccg-208634
33. Ncgc00163621-01
34. (z)-ethylidene-hydroxy-dimethyl-[?]dione
35. Ac-34604
36. As-79841
37. Cs-0022892
38. C06176
39. A905119
40. J-005736
41. Q2083871
42. Wln: T55-12-1a Q En Iovy Ovo Butj Ku2 M Nq N
43. Wln: T55-12- 1a Q En Iovy Ovo Butj Ku2 M1 Nq N1
44. (1r,4z,6r,7r,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
45. (5r,6r,9a1r,14ar,z)-3-ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
| Molecular Weight | 335.4 g/mol |
|---|---|
| Molecular Formula | C18H25NO5 |
| XLogP3 | 1.1 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 0 |
| Exact Mass | 335.17327290 g/mol |
| Monoisotopic Mass | 335.17327290 g/mol |
| Topological Polar Surface Area | 76.1 Ų |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Complexity | 611 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Senecio herb is used /as a folk remedy/ for diabetes mellitus, hemorrhage, high blood pressure, for spasms, and as a uterine stimulant.
Blumenthal M, ed; The Complete German Commission E Monographs: Therapeutic Guide to Herbal Medicines p. 376 (1998)
Senecio herb contains varying amounts of toxic pyrrolizidine alkaloids (PA) which are known to have organotoxic, in particular hepatotoxic,effects
Blumenthal M, ed; The Complete German Commission E Monographs: Therapeutic Guide to Herbal Medicines p. 376 (1998)
The therapeutic administration of senecio herb is not justifiable because of its insufficient or undocumented effectiveness and the presence of toxic pyrrolizidine alkaloids.
Blumenthal M, ed; The Complete German Commission E Monographs: Therapeutic Guide to Herbal Medicines p. 376 (1998)
Antineoplastic Agents, Phytogenic
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)
In animal studies highest concentrations were found in the liver, lungs, kidneys and spleen. /pyrrolizidine alkaloids/
IPCS; Poisons Information Monograph (484) on Senecio Vulgaris L. (September 1989). Available from, as of September 15, 2003: https://www.inchem.org/documents/pims/plant/senecio.htm
Blood levels of senecionine in rats given 0.1 LD50 ip were determined. The levels were 0.38, 0.32, and 0.14 mg/litre at 0.5, 1, and 2 h after injection, respectively.
WHO; Environ Health Criteria 80: Pyrrolizidine Alkaloids (1988). Available from, as of September 25, 2003: https://www.inchem.org/pages/ehc.html
...Senecionine... /was/ studied regarding the distribution, excretion, transfer into milk, and covalent binding to hepatic macromolecules in BALB/c mice. After injection, radioactivity was rapidly excreted in the urine and feces (84% or greater) within 16 hr. The liver contained over 1.5% of the dose at 16 hr. A small amount, 0.04%, of the dose was transferred into the milk in 16 hr; the majority of radioactivity was found in the skim-milk fraction, suggesting that the PA's were transferred to the milk as water-soluble metabolites. ...The binding to calf thymus DNA and microsomal macromolecules was measured in vitro. The binding was diminished in the absence of O2 or a NADPH-generating system or by boiling the microsomes.
PMID:6179729 Eastman DF et al; Drug Metab Dispos 10 (3):236-40 (1982)
...Following intravenous administration of [14C]SEN (60 mg/kg, 10 microCi/kg), bile, urine and blood were collected over a 7-hr period. Of the total administered radioactivity, 44% and 43% were excreted in the bile and urine, respectively. Using mass spectroscopy, senecionine N-oxide (SENNOX) was identified as the major metabolite in bile (52% of 44%) and urine (30% of 43%). For the total 7 hr, <5% in bile and 18% in urine was excreted as parent alkaloid.
Estep JE et al; Toxicology 61 (2): 179-89 (1990)
Using microsomes from livers of phenobarbitone-pretreated male rats, pyrrolizidine alkaloids tested were metabolized to n-oxides and pyrroles.
MATTOCKS A, ET AL; PYRROLIC AND N-OXIDE METABOLITES FORMED PYRROLIZIDINE ALKALOIDS BY HEPATIC MICROSOMES IN VITRO: RELEVANCE TO IN VIVO HEPATOTOXICITY; CHEM-BIOL INTERACT 43 (2): 209-22 (1983)
The in vitro mouse hepatic microsomal metabolism of the macrocyclic pyrrolizidine alkaloid senecionine was studied. Senecic acid, senecionine n-oxide and 19-hydroxysenecionine, a new metabolite, were isolated from the microsomal enzyme system of balb/c mice.
EASTMAN DF, SEGALL HJ; A NEW PYRROLIZIDINE ALKALOID METABOLITE, 19-HYDROXYSENECIONINE ISOLATED FROM MOUSE HEPATIC MICROSOMES IN VITRO; DRUG METAB DISPOS 10 (6): 696-99 (1982)
The toxic pyrrolizidine alkaloids, such as senecionine, are cyclic arylamines that are dehydrogenated by cytochrome P450 (CYP3A4) to the corresponding pyrroles. Pyrroles themselves are nucleophiles, but electrophiles are generated through the loss of substituents on the pyrrolizidine nucleus... .
Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 190
In animals, the major metabolic routes of pyrrolizidine alkaloids are: (a) hydrolysis of the ester groups; (b) N-oxidation; and (c) dehydrogenation of the pyrrolizidine nucleus to pyrrolic derivatives. Routes (a) and (b) are believed to be detoxification mechanisms. Route (c) leads to toxic metabolites. Route (a) occurs in liver and blood; routes (b) and (c) are brought about in the liver by the microsomal mixed function oxidase system. /pyrrolizidine alkaloids/
IPCS; Poisons Information Monograph (484) on Senecio Vulgaris L. (September 1989). Available from, as of September 15, 2003: https://www.inchem.org/documents/pims/plant/senecio.htm
For more Metabolism/Metabolites (Complete) data for SENECIONINE (7 total), please visit the HSDB record page.
Within a few hours, only a relatively small proportion of the administered dose remains in the body. Much of this is in the form of metabolites bound to tissue contents. A pyrrolizidine N-oxide disappeared from the serum after IV administration in animals, with initial half-lives of 3 to 20 minutes. /pyrrolizidine alkaloids/
IPCS; Poisons Information Monograph (484) on Senecio Vulgaris L. (September 1989). Available from, as of September 15, 2003: https://www.inchem.org/documents/pims/plant/senecio.htm
On the isolated guinea pig ileum preparation, platyphylline, supinine, heleurine, and cynaustraline were more potent in antagonizing responses to acetylcholine (ii). Their anticholinergic activity appeared to involve a competitive mechanism. The pyrrolizidine alkaloids had no appreciable activity as antagonists of (ii) in the isolated toad rectus abdominis preparation.
POMEROY AR, RAPER C; PYRROLIZIDINE ALKALOIDS: ACTIONS ON MUSCARINIC RECEPTORS IN THE GUINEA PIG ILEUM; BRIT J PHARMACOL 41 (4): 680-90 (1971)
The activation of the alkaloids by mixed-function oxidases leads to pyrrolic dehydro-alkaloids which are reactive alkylating agents. The liver necrosis results from binding of the metabolites with the liver cell. Some metabolites are released into the circulation and are believed to pass beyond the liver to the lung causing vascular lesions. The pyrrolic metabolites are cytotoxic and act on the hepatocytes and on the endothelium of blood vessels of the liver and lung. /pyrrolizidine alkaloids/
IPCS; Poisons Information Monograph (484) on Senecio Vulgaris L. (September 1989). Available from, as of September 15, 2003: https://www.inchem.org/documents/pims/plant/senecio.htm
Senecionine admin showed spasmolytic activity, primarily on intestinal smooth muscles.
LITVINCHUK MD ET AL; SPASMOLYTIC PROPERTIES OF PYRROLIZIDINE ALKALOIDS; FARMAKOL TOKSIKOL (MOSCOW) 42 (5): 509-11 (1979)
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