alpha-Chaconine

Names

[ CAS No. ]:
20562-03-2

[ Name ]:
alpha-Chaconine

[Synonym ]:
chaconine
chaconine,a
a-chaconine with tlc
a-chaconine
a-chaconine from potato sprouts
alpa-chaconine

Biological Activity

[Description]:

α-Chaconine, isolated from a Solanum tuberosum L. cv Jayoung, inhibits the expressions of COX-2, IL-1β, IL-6, and TNF-α at the transcriptional level. α-Chaconine inhibits the LPS-induced expressions of iNOS and COX-2 at the protein and mRNA levels and their promoter activities in RAW 264.7 macrophages. Anti-inflammatory effects[1].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

[Target]

COX-2

[In Vitro]

α-Chaconine attenuates the transcriptional activity of activator protein-1 (AP-1) by reducing the translocation and phosphorylation of c-Jun.α-Chaconine suppresses lipopolysaccharide-induced pro-inflammatory mediators via AP-1 inactivation in RAW 264.7 macrophages and protects mice from endotoxin shock.α-Chaconine also suppresses the phosphorylation of TGF-β-activated kinase-1 (TAK1), which lies upstream of MKK7/JNK signaling[1].

[References]

[1]. Lee KG, et al. α-Chaconine isolated from a Solanum tuberosum L. cv Jayoung suppresses lipopolysaccharide-induced pro-inflammatory mediators via AP-1 inactivation in RAW 264.7 macrophages and protects mice from endotoxin shock. Chem Biol Interact. 2015 Jun 25;235:85-94.

Chemical & Physical Properties

[ Density]:
1.37 g/cm3

[ Melting Point ]:
228-236ºC

[ Molecular Formula ]:
C₄₅H₇₃NO₁₄

[ Molecular Weight ]:
852.05900

[ Exact Mass ]:
851.50300

[ PSA ]:
220.46000

[ LogP ]:
1.12070

[ Index of Refraction ]:
1.621

[ Water Solubility ]:
pyridine: 10 mg/mL, clear, very faintly yellow

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FL6700000

CHEMICAL NAME :: alpha-Chaconine

CAS REGISTRY NUMBER :: 20562-03-2

BEILSTEIN REFERENCE NO. :: 0077396

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C45-H73-N-O14

MOLECULAR WEIGHT :: 852.19

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 :: 84 mg/kg

TOXIC EFFECTS :: Blood - hemorrhage

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 19 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - cyanosis

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 50 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 160 mg/kg/8D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 80 mg/kg/2D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 40 mg/kg

SEX/DURATION :: female 5-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 20 mg/kg

SEX/DURATION :: female 5-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 165 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 90 mg/kg/3D (Continuous)

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 33,191,1995 *** REVIEWS *** TOXICOLOGY REVIEW FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 17,61,1979

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R63

[ Safety Phrases ]:
22-36/37

[ RIDADR ]:
UN 1544

[ WGK Germany ]:
3

[ RTECS ]:
FL6700000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)