Arctigenin

Names

[ Name ]:
Arctigenin

[Synonym ]:
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

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]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> MMP

Research Areas >> Cancer

Natural Products >> Phenylpropanoids

[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.

[Related Small Molecules]

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

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ WGK Germany ]:
3