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Grossamide

Names

[ CAS No. ]:
80510-06-1

[ Name ]:
Grossamide

[Synonym ]:
2-(4-Hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[(1E)-3-{[2-(4-hydroxyphenyl)ethyl]amino}-3-oxo-1-propen-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide
trans-divinyl ethylene oxide
3-Benzofurancarboxamide, 2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[(1E)-3-[[2-(4-hydroxyphenyl)ethyl]amino]-3-oxo-1-propen-1-yl]-7-methoxy-
trans-2,3-Divinyloxirane
trans-grossamide

Biological Activity

[Description]:

Grossamide is a natural product that can be isolated from fructus cannabis, the dried fruit of Cannabis sativa L.. Grossamide has anti-neuroinflammatory effects[1].

[Related Catalog]:

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

[In Vitro]

Grossamide downregulates LPS-mediated production of inflammatory molecules[1]. Grossamide (0-20 μM, 1 h) inhibits the mRNA levels of TNF-α and IL-6 in a dose-dependent manner, inhibits LPS-induced NF-κB activation, and inhibits LPS-induced TLR4 and MyD88 expression without cytotoxicity[1]. RT-PCR[1] Cell Line: BV-2 microglia cell Concentration: 0, 10, 15, and 20 μM Incubation Time: 1 h and co-cultured with LPS (100 ng/mL) for another 6 h Result: Inhibited the mRNA levels of TNF-α and IL-6 in a dose-dependent manner. Western Blot Analysis[1] Cell Line: BV-2 microglia cell Concentration: 0, 10, 15, and 20 μM Incubation Time: 1 h followed by LPS (100 ng/mL) stimulation for 1 h or 24 h Result: Inhibited LPS-induced phosphorylation of IκBα and significantly reduced phosphorylation of NF-κB p65 levels. Dose-dependently decreased the expression of TLR4 and MyD88. Cell Viability Assay[1] Cell Line: BV-2 microglia cell Concentration: 0, 10, 15, and 20 μM Incubation Time: 1 h and co-cultured in the absence or presence of 100 ng/ mL LPS for 24 h Result: Had no cytotoxicity.

[References]

[1]. Luo Q, et al. Anti-neuroinflammatory effects of grossamide from hemp seed via suppression of TLR-4-mediated NF-κB signaling pathways in lipopolysaccharide-stimulated BV2 microglia cells. Mol Cell Biochem. 2017 Apr;428(1-2):129-137.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
934.8±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C36H36N2O8

[ Molecular Weight ]:
624.68

[ Flash Point ]:
519.2±34.3 °C

[ Exact Mass ]:
624.247192

[ PSA ]:
146.58000

[ LogP ]:
2.98

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.654

Safety Information

[ Hazard Codes ]:
Xi

Synthetic Route

Precursor & DownStream


Related Compounds

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