Seneciphylline

Modify Date: 2024-01-02 23:23:13

Seneciphylline Structure
Seneciphylline structure
 Common Name Seneciphylline
CAS Number 480-81-9 Molecular Weight 333.379
Density 1.3±0.1 g/cm3 Boiling Point 577.7±50.0 °C at 760 mmHg
Molecular Formula C18H23NO5 Melting Point 217ºC
MSDS Chinese USA Flash Point 303.2±30.1 °C
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Seneciphylline


Seneciphylline is a toxic pyrrolizidine alkaloid in Senecio plants[1]. Seneciphylline significantly increases the activities of epoxide hydrase and glutathione-S-transferase but causes reduction of cytochrome P-450 and related monooxygenase activities[2].

 Names

Name Seneciphylline
Synonym More Synonyms

 Seneciphylline Biological Activity

Description Seneciphylline is a toxic pyrrolizidine alkaloid in Senecio plants[1]. Seneciphylline significantly increases the activities of epoxide hydrase and glutathione-S-transferase but causes reduction of cytochrome P-450 and related monooxygenase activities[2].
Related Catalog
References

[1]. Bandyopadhyay S, et al. Cytotoxicity of Senecio in macrophages is mediated via its induction of oxidative stress. Res Vet Sci. 2009 Aug;87(1):85-90.

[2]. Kakrani HK, et al. Effect of seneciphylline and senecionine on hepatic drug metabolizing enzymes in rats. J Ethnopharmacol. 1984 Dec;12(3):271-8.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 577.7±50.0 °C at 760 mmHg
Melting Point 217ºC
Molecular Formula C18H23NO5
Molecular Weight 333.379
Flash Point 303.2±30.1 °C
Exact Mass 333.157623
PSA 76.07000
LogP 0.81
Vapour Pressure 0.0±3.6 mmHg at 25°C
Index of Refraction 1.581
Storage condition 2-8℃

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VT5977000
CHEMICAL NAME :
Seneciphylline
CAS REGISTRY NUMBER :
480-81-9
LAST UPDATED :
199612
DATA ITEMS CITED :
15
MOLECULAR FORMULA :
C18-H23-N-O5
MOLECULAR WEIGHT :
333.42

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
77 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
77 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - acute pulmonary edema Liver - hepatitis (hepatocellular necrosis), diffuse Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
90 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - acute pulmonary edema Liver - hepatitis (hepatocellular necrosis), diffuse Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
322 mg/kg/2W-I
TOXIC EFFECTS :
Brain and Coverings - other degenerative changes Vascular - other changes Liver - other changes
TYPE OF TEST :
Sex chromosome loss and nondisjunction

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
600 ug/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 142,209,1985 *** REVIEWS *** IARC Cancer Review:Animal No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,319,1976 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,319,1976 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements Missing Phrase - N15.00950417
Hazard Codes T
Risk Phrases R23/24/25
Safety Phrases 1-20-24/25-45
RIDADR UN 1544
Packaging Group III
Hazard Class 6.1(b)

 Articles18

More Articles
Interplant alkaloid variation and Senecio vernalis toxicity in cattle.

Vet. Hum. Toxicol. 43(3) , 147-51, (2001)

Senecio vernalis and other plants containing pyrrolizidine alkaloids (PA) are implicated in the poisoning of cattle. The liver is a known target organ. In this study the content of the alkaloids senec...

Pyrrolizidine alkaloids in pollen and pollen products.

Mol. Nutr. Food. Res. 54(2) , 292-300, (2010)

Recently, 1,2-dehydropyrrolizidine alkaloid (PA) ester alkaloids, found predominantly as their N-oxides (PANOs, pyrrolizidine N-oxides), have been reported in both honey and in pollen obtained directl...

Mutagenic activity of the pyrrolizidine alkaloids seneciphylline and senkirkine in Drosophila and their transfer into rat milk.

Food Chem. Toxicol. 22(3) , 223-5, (1984)

Seneciphylline and senkirkine, two pyrrolizidine alkaloids that occur in animal feeds and medicinal herbs, respectively, have been tested for their ability to produce sex-linked recessive lethals in m...

 Synonyms

(3Z,6R,14aR,14bR)-3-Ethylidene-6-hydroxy-6-methyl-5-methylene-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
Jacodine
[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-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)-
a-Longilobine
α-Longilobine
(15Z)-12-Hydroxy-13,19-didehydrosenecionan-11,16-dione
seneciphylline
(3Z,6R,14aR,14bR)-3-Ethyliden-6-hydroxy-6-methyl-5-methylen-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizin-2,7-dion
(3Z,6R,14aR,14bR)-3-éthylidène-6-hydroxy-6-méthyl-5-méthylène-3,4,5,6,9,11,13,14,14a,14b-décahydro[1,6]dioxacyclododécino[2,3,4-gh]pyrrolizine-2,7-dione
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