Napellonine

Names

[ CAS No. ]:
509-24-0

[ Name ]:
Napellonine

[Synonym ]:
(1S,7R,8R,9S,10S,13R,16S)-11-Ethyl-7,16-dihydroxy-13-methyl-6-methylene-11-azahexacyclo[7.7.2.1.0.0.0]nonadecan-4-one
Napellonine
Zongorine
Bullatine G

Biological Activity

[Description]:

Songorine is a diterpenoid alkaloid isolated from the genus Aconitum. Songorine is a GABAA receptor antagonist in rat brain and has anti cancer, antiarrhythmic and anti-inflammatory activities. Songorine has the potential for the treatment of Epithelial ovarian cancer (EOC)[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[Target]

IC50: GABAA receptor[1]

[In Vivo]

Songorine is investigated its efficacy and safety in SKOV3 tumorbearing BALB/c nude mice, songorine inhibits EOC cell survival, invasion and migration, promoted EOC cell apoptosis and suppressed mammalian EOC tumorigenic behavior. In addition, western blot and IHC results show that songorine consistently downregulates the expression of Ncadherin, vimentin, matrix metalloproteinase (MMP)2, MMP9, phosphorylated GSK3β, βcatenin and Bcl2, and upregulated the expression of Ecadherin, cleaved caspase3, cleaved caspase9 and Bax[1]. Songorine shows an Antiarrhythmic activity in aconitine-induced arrhythmia model in rats, exhibits LD50 and ED50 values of 142 mg and 7.3mg, respectively[2].

[References]

[1]. Zhang H, et al. Songorine suppresses cell growth and metastasis in epithelial ovarian cancer via the Bcl‑2/Bax and GSK3β/β‑catenin signaling pathways.Oncol Rep. 2019 May;41(5):3069-3079.

[2]. Khan H, et al. Therapeutic potential of songorine, a diterpenoid alkaloid of the genus Aconitum.Eur J Med Chem. 2018 Jun 10;153:29-33.

Chemical & Physical Properties

[ Density]:
1.29

[ Boiling Point ]:
535.8±50.0 °C at 760 mmHg

[ Melting Point ]:
201-203ºC

[ Molecular Formula ]:
C₂₂H₃₁NO₃

[ Molecular Weight ]:
357.486

[ Flash Point ]:
277.8±30.1 °C

[ Exact Mass ]:
357.230408

[ PSA ]:
60.77000

[ LogP ]:
0.71

[ Vapour Pressure ]:
0.0±3.2 mmHg at 25°C

[ Index of Refraction ]:
1.630

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WG0780000

CHEMICAL NAME :: Songorine

CAS REGISTRY NUMBER :: 509-24-0

BEILSTEIN REFERENCE NO. :: 0045107

LAST UPDATED :: 199709

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C22-H31-N-O3

MOLECULAR WEIGHT :: 357.54

WISWESSER LINE NOTATION :: T G5 D665 B6 B6/G-J/CL/LR A G- 5BBCCJ R CX FV HY JX MNTJ HU1 IQ M2 O1 RQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 408 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JOETD7 Journal of Ethnopharmacology. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1979- Volume(issue)/page/year: 4,247,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1575 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JOETD7 Journal of Ethnopharmacology. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1979- Volume(issue)/page/year: 4,247,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 485 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JOETD7 Journal of Ethnopharmacology. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1979- Volume(issue)/page/year: 4,247,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 630 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JOETD7 Journal of Ethnopharmacology. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1979- Volume(issue)/page/year: 4,247,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 15,5,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 142 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989 Volume(issue)/page/year: 11,1374,1989