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Santamarine

Names

[ CAS No. ]:
4290-13-5

[ Name ]:
Santamarine

[Synonym ]:
(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-b]furan-2(3H)-one
Naphtho(1,2-b)furan-2(3H)-one, 3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS,5aR,6R,9aS,9bS)-
Naphtho[1,2-b]furan-2(3H)-one, 3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS,5aR,6R,9aS,9bS)-
Santamarin
(3aS,5aR,6R,9aS,9bS)-6-Hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-b]furan-2(3H)-one
Balchanin
(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one

Biological Activity

[Description]:

Santamarine (Santamarin), a sesquiterpene lactone, increases HO-1 expression through Nrf2 translocation and suppresses NO, PGE2, TNF-α, and IL-1β production through inhibition of NF-κB translocation in LPS-induced macrophages. Santamarine shows anti-photoaging properties via inhibition of MAPK/AP-1 and stimulation of TGF-β/Smad signaling in UVA-irradiated human dermal fibroblasts (HDFs). Antioxidant activities[1][2].

[Related Catalog]:

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

[References]

[1]. Choi HG, et al. Santamarin, a sesquiterpene lactone isolated from Saussurea lappa, represses LPS-induced inflammatory responses via expression of heme oxygenase-1 in murine macrophage cells. Int Immunopharmacol. 2012;13(3):271-279.

[2]. Oh JH, et al. Santamarine Shows Anti-Photoaging Properties via Inhibition of MAPK/AP-1 and Stimulation of TGF-β/Smad Signaling in UVA-Irradiated HDFs. Molecules. 2021;26(12):3585. Published 2021 Jun 11.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
415.6±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C15H20O3

[ Molecular Weight ]:
248.318

[ Flash Point ]:
176.5±21.5 °C

[ Exact Mass ]:
248.141251

[ PSA ]:
46.53000

[ LogP ]:
1.94

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.555

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds