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Licarin B

Names

[ CAS No. ]:
51020-87-2

[ Name ]:
Licarin B

[Synonym ]:
5-{(2R,3R)-7-methoxy-3-methyl-5-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran-2-yl}-1,3-benzodioxole
Eupomatenoid-8
1,3-Benzodioxole, 5-[(2R,3R)-2,3-dihydro-7-methoxy-3-methyl-5-[(1E)-1-propen-1-yl]-2-benzofuranyl]-
(-)-Licarin B
5-{(2R,3R)-7-Methoxy-3-methyl-5-[(1E)-1-propen-1-yl]-2,3-dihydro-1-benzofuran-2-yl}-1,3-benzodioxole

Biological Activity

[Description]:

Licarin B, a nitric oxide production inhibitor extracted from the component of the seeds of Myristica fragrans, improves insulin sensitivity via PPARγ and activation of GLUT4 in the IRS-1/PI3K/AKT pathway[1][2][3].

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR
Research Areas >> Metabolic Disease

[In Vitro]

Licarin B (5 μM, 10 μM, 15 μM. 8 days) moderately increases TG accumulation during adipogenic differentiation and showed partial PPARg agonist activity in 3T3-L1 preadipocytes[2]. Cell Viability Assay[1] Cell Line: 3T3-L1 cell. Concentration: 1-500 μM. Incubation Time: 48 h. Result: Did not cause significant cell death up to 500 μM concentration. Cell Viability Assay[1] Cell Line: 3T3-L1 cell. Concentration: 5 μM, 10 μM, 15 μM. Incubation Time: 8 days (replaced every 2 days). Result: LB at 15 μM concentration significantly promoted adipocyte differentiation and caused intracellular TG accumulation.

[References]

[1]. Kim YB, et al. The crystal structure of licarin-B, (C20H20O4), a component of the seeds of Myristica fragrans. Arch Pharm Res. 1991 Mar;14(1):1-6.

[2]. G. L. Shyni, et al. Licarin B from Myristica fragrans improves insulin sensitivity via PPARγ and activation of GLUT4 in the IRS-1/PI3K/AKT pathway in 3T3-L1 adipocytes. RSC Adv. 2016.

[3]. Cao GY, et al. New inhibitors of nitric oxide production from the seeds of Myristica fragrans. Food Chem Toxicol. 2013 Dec;62:167-71.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
428.5±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C20H20O4

[ Molecular Weight ]:
324.370

[ Flash Point ]:
131.4±35.6 °C

[ Exact Mass ]:
324.136169

[ PSA ]:
36.92000

[ LogP ]:
5.08

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.608

[ Storage condition ]:
2-8C

Related Compounds