Tussilagone

Names

[ Name ]:
Tussilagone

[Synonym ]:
(1S,3aS,5R,7S,7aS)-1-[(1R)-1-Acetoxyethyl]-7-isopropyl-4-methylene-2-oxooctahydro-1H-inden-5-yl (2E)-3-methyl-2-pentenoate
Tussilagone
2-Pentenoic acid, 3-methyl-, (1S,3aS,5R,7S,7aS)-1-[(1R)-1-(acetyloxy)ethyl]octahydro-4-methylene-7-(1-methylethyl)-2-oxo-1H-inden-5-yl ester, (2E)-

Biological Activity

[Description]:

Tussilagone, a major active component in Tussilago farfara, has anti-inflammatory effect. Tussilagone ameliorates inflammatory responses in dextran sulphate sodium-induced murine colitis. Tussilagone inhibits the inflammatory response and improves survival in cecal ligation and puncture (CLP)-induced septic mice[1][2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[In Vitro]

Tussilagone suppressed the expression of the inflammatory mediators, nitric oxide and prostaglandin E2, and the inflammatory cytokines, tumor necrosis factor-alpha (TNF-α) and high-mobility group box 1 (HMGB1), in lipopolysaccharide-stimulated RAW 264.7 cells and peritoneal macrophages. Tussilagone also reduced the activation of the mitogen-activated protein kinases and nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) involved in the activation of various inflammatory mediators in activated macrophages[1].

[In Vivo]

Tussilagone administration (1 mg/kg and 10 mg/kg) produced decreased mortality and lung injury in CLP-activated septic mice. Augmented expression of cyclooxygenase (COX)-2 and TNF-α in pulmonary alveolar macrophages of septic mice were attenuated by tussilagone administration[2].

[References]

[1]. Cheon HJ, et al. Tussilagone, a major active component in Tussilago farfara, ameliorates inflammatory responses in dextran sulphate sodium-induced murine colitis. Chem Biol Interact. 2018 Oct 1;294:74-80.

[2]. Kim YK, et al. Tussilagone Inhibits the Inflammatory Response and Improves Survival in CLP-Induced SepticMice. Int J Mol Sci. 2017 Dec 18;18(12). pii: E2744.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
471.3±35.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₃H₃₄O₅

[ Molecular Weight ]:
390.513

[ Flash Point ]:
200.7±26.0 °C

[ Exact Mass ]:
390.240631

[ PSA ]:
69.67000

[ LogP ]:
5.03

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.502

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SB3100000

CHEMICAL NAME :: 2-Pentenoic acid, 3-methyl-, 1-(1-(acetyloxy)ethyl)octahydro-4-methylene-7-(1-meth ylethyl)-2- oxo-1H-inden-5-yl ester, (1S-(1-alpha(S*),3a-beta,5-beta(E),7-alpha,7a-alpha)) -

CAS REGISTRY NUMBER :: 104012-37-5

LAST UPDATED :: 198909

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C23-H34-O5

MOLECULAR WEIGHT :: 390.57

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 28900 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - respiratory stimulation Lungs, Thorax, or Respiration - other changes

REFERENCE :: GEPHDP General Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.6- 1975- Volume(issue)/page/year: 19,261,1988

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
24/25

[ HS Code ]:
29389090

Related Compounds

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