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dehydrocurdione

Names

[ CAS No. ]:
38230-32-9

[ Name ]:
dehydrocurdione

[Synonym ]:
MFCD03792779

Biological Activity

[Description]:

Dehydrocurdione, a zedoary-derived sesquiterpene, induces heme oxygenase (HO)-1, an antioxidative enzyme, in RAW 264.7 macrophages. Dehydrocurdione interacts with Keap1, resulting in Nrf2 translocation followed by activation of the HO-1 E2 enhancer. Dehydrocurdione suppresses lipopolysaccharide-induced NO release, a marker of inflammation. Anti-inflammatory activity[1][2].

[Related Catalog]:

Signaling Pathways >> NF-κB >> Keap1-Nrf2
Research Areas >> Inflammation/Immunology

[In Vitro]

Dehydrocurdione (RAW 264.7 cells) concentration-dependently increases the HO-1 mRNA level for 3 hr and the protein level for 6 hr, and both effects reached significance at a concentration of 100 μM[1]. Dehydrocurdione interacts with Keap, resulting in Nrf2 translocation followed by activation ofthe HO-1 E2 enhancer[1]. Western Blot Analysis[1] Cell Line: RAW 264.7 cells Concentration: 100 μM Incubation Time: 24 hours Result: Transiently increased the HO-1 protein level, and its effect peaked at 3-6 hr.

[In Vivo]

Dehydrocurdione (P.o ;120 mg/kg, daily for 12 days) significantly reduces chronic adjuvant arthritis[2]. Dehydrocurdione (200 mg/kg; p.o.; Sprague-Dawley rats) dose-dependently inhibits carrageenan-induced paw edema[2]. Animal Model: Wistar rats[2] Dosage: 120 mg/kg Administration: P.o ; daily for 12 days Result: Significantly reduces chronic adjuvant arthritis.

[References]

[1]. Ohnishi M, et al. Curcuma sp.-derived dehydrocurdione induces heme oxygenase-1 through a Michael reaction between its α, β-unsaturated carbonyl and Keap1. Phytother Res. 2018;32(5):892-897.

[2]. Yoshioka T, et al. Antiinflammatory potency of dehydrocurdione, a zedoary-derived sesquiterpene. Inflamm Res. 1998;47(12):476-481.

Chemical & Physical Properties

[ Density]:
0.962g/cm3

[ Boiling Point ]:
362.9ºC at 760 mmHg

[ Molecular Formula ]:
C15H22O2

[ Molecular Weight ]:
234.33400

[ Flash Point ]:
136.2ºC

[ Exact Mass ]:
234.16200

[ PSA ]:
34.14000

[ LogP ]:
3.61740

[ Index of Refraction ]:
1.477