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Bakkenolide B

Names

[ CAS No. ]:
18455-98-6

[ Name ]:
Bakkenolide B

[Synonym ]:
(3R,3'R,3a'R,4'S,7'S,7a'R)-3'-Acetoxy-7',7a'-dimethyl-4-methylene-2-oxodecahydrospiro[furan-3,2'-inden]-4'-yl (2Z)-2-methyl-2-butenoate
2-Butenoic acid, 2-methyl-, (3R,3'R,3a'R,4'S,7'S,7a'R)-3'-(acetyloxy)decahydro-7',7'a-dimethyl-4-methylene-2-oxospiro[furan-3(2H),2'-[2H]inden]-4'-yl ester, (2Z)-

Biological Activity

[Description]:

Bakkenolide B is isolated from petasites japonicas leaves and has anti-allergic and anti-inflammatory effects. Bakkenolide B can be used for the study of asthma[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Inflammation/Immunology

[In Vitro]

Bakkenolide B (0-100 μg/ml; pretreatment 30 mins) inhibits antigen-induced β-hexosamidase release from RBL2H3 mast cells in a concentration-dependent manner[1]. Bakkenolide B (0-10 μg/ml; 1 h later stimulated with LPS) strongly inhibits the gene inductions of inducible nitric oxide synthase and cyclooxygenase-2 in a concentration-dependent manner in mouse peritoneal macrophages[1]. Western Blot Analysis[1] Cell Line: Mouse peritoneal macrophages Concentration: 0 μg/ml; 1 μg/ml; 3 μg/ml; 5 μg/ml; 10 μg/ml Incubation Time: 1 h later stimulated with LPS Result: Decreased iNOS and cox-2 protein expression.

[In Vivo]

Bakkenolide B (intraperitoneal injection; 1 mg/ml; 1 h before ovalbumin nebulization on days 28, 29, and 30) strongly inhibits the accumulation of eosinophils, macrophages, and lymphocytes to bronchoalveolar lavage fluid (BALF) in ovalbumin-induced asthma mice[1]. Animal Model: Ovalbumin-induced asthma mice[1] Dosage: 1 mg/ml Administration: Intraperitoneal injection; 1 h before ovalbumin nebulization on days 28, 29, and 30 Result: Exhibited anti-allergic effects in mice.

[References]

[1]. Lee KP, et al. Anti-allergic and anti-inflammatory effects of bakkenolide B isolated from Petasites japonicus leaves.J Ethnopharmacol. 2013 Jul 30;148(3):890-4.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
503.0±50.0 °C at 760 mmHg

[ Melting Point ]:
101-102 °C

[ Molecular Formula ]:
C22H30O6

[ Molecular Weight ]:
390.470

[ Flash Point ]:
217.1±30.2 °C

[ Exact Mass ]:
390.204254

[ LogP ]:
4.07

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.526

Related Compounds