Arctigenin

Modify Date: 2024-01-02 18:50:16

Arctigenin Structure
Arctigenin structure
 Common Name Arctigenin
CAS Number 7770-78-7 Molecular Weight 372.412
Density 1.2±0.1 g/cm3 Boiling Point 567.0±45.0 °C at 760 mmHg
Molecular Formula C21H24O6 Melting Point 100 °C
MSDS N/A Flash Point 198.8±22.2 °C

 Use of Arctigenin


Arctigenin is a lignan found in certain plants of the Asteraceae; it has shown antiviral and anticancer effects in glass; it is the aglycone of arctiin.IC50 value: Target: anticancer agentArctiin and its aglucone, arctigenin from the fruits of Arctium lappa L. showed potent in vitro antiviral activities against influenza A virus (A/NWS/33, H1N1) (IFV). Based on the data from time-of-addition experiments and on release tests of progeny viruses, arctigenin was assumed to interfere with early event(s) of viral replication after viral penetration into cells, and to suppress the release of progeny viruses from the host cells [1]. arctigenin treatment reduced viability of bladder cancer T24 cells in a dose- and time-dependent manner after treatment with arctigenin (10, 20, 40, 80, and 100 μmol/L) for 24 hr and 48 hr. Arctigenin treatment clearly arrested tumor cells in the G1 phase of the cell cycle. At the molecular level, arctigenin treatment decreased cyclin D1 expression, whereas CDK4 and CDK6 expression levels were unaffected. Moreover, arctigenin selectively altered the phosphorylation of members of the MAPK superfamily, decreasing phosphorylation of ERK1/2 and activated phosphorylation of p38 significantly in a dose-dependent manner [2]. The use of arctigenin has been shown to be effective in a mouse model of Japanese encephalitis [3].

 Names

Name (-)-Arctigenin
Synonym More Synonyms

 Arctigenin Biological Activity

Description Arctigenin is a lignan found in certain plants of the Asteraceae; it has shown antiviral and anticancer effects in glass; it is the aglycone of arctiin.IC50 value: Target: anticancer agentArctiin and its aglucone, arctigenin from the fruits of Arctium lappa L. showed potent in vitro antiviral activities against influenza A virus (A/NWS/33, H1N1) (IFV). Based on the data from time-of-addition experiments and on release tests of progeny viruses, arctigenin was assumed to interfere with early event(s) of viral replication after viral penetration into cells, and to suppress the release of progeny viruses from the host cells [1]. arctigenin treatment reduced viability of bladder cancer T24 cells in a dose- and time-dependent manner after treatment with arctigenin (10, 20, 40, 80, and 100 μmol/L) for 24 hr and 48 hr. Arctigenin treatment clearly arrested tumor cells in the G1 phase of the cell cycle. At the molecular level, arctigenin treatment decreased cyclin D1 expression, whereas CDK4 and CDK6 expression levels were unaffected. Moreover, arctigenin selectively altered the phosphorylation of members of the MAPK superfamily, decreasing phosphorylation of ERK1/2 and activated phosphorylation of p38 significantly in a dose-dependent manner [2]. The use of arctigenin has been shown to be effective in a mouse model of Japanese encephalitis [3].
Related Catalog
References

[1]. Hayashi K, et al. Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza A virus. Biol Pharm Bull. 2010;33(7):1199-205.

[2]. Yang S, et al. Arctigenin anti-tumor activity in bladder cancer T24 cell line through induction of cell-cycle arrest and apoptosis. Anat Rec (Hoboken). 2012 Aug;295(8):1260-6.

[3]. Swarup V, et al. Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan. J Antimicrob Chemother. 2008 Mar;61(3):679-88.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 567.0±45.0 °C at 760 mmHg
Melting Point 100 °C
Molecular Formula C21H24O6
Molecular Weight 372.412
Flash Point 198.8±22.2 °C
Exact Mass 372.157288
PSA 74.22000
LogP 2.47
Appearance of Characters solid
Vapour Pressure 0.0±1.6 mmHg at 25°C
Index of Refraction 1.576
Storage condition −20°C
Water Solubility DMSO: 34 mg/mL with heating and sonicating, soluble

 Safety Information

Hazard Codes Xi
Safety Phrases S22-S24/25
WGK Germany 3

 Synonyms

Arctigenin
UNII:2FD8L150E7
(2S)-2-[(2S,12bS)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]but-3-en-1-ol
2-(1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-but-3-en-1-ol
MFCD00870597
(-)-Arctigenin
(-)-arctigenine
2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)-
(3R,4R)-4-(3,4-Dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
l-Arctigenin
(3R,4R)-4-(3,4-Dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydro-2(3H)-furanone
(-)-antirhine
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