CAS 7770-78-7|Arctigenin

Introduction：Basic information about CAS 7770-78-7|Arctigenin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Arctigenin BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Synonyms

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	/	Flash Point	198.8±22.2 °C

Names

Name	(-)-Arctigenin
Synonym	More Synonyms

Arctigenin BiologicalActivity

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 >>AutophagySignaling Pathways >>Metabolic Enzyme/Protease >>MMPResearch Areas >>CancerNatural 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.

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 >>AutophagySignaling Pathways >>Metabolic Enzyme/Protease >>MMPResearch Areas >>CancerNatural 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.

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
InChIKey	NQWVSMVXKMHKTF-JKSUJKDBSA-N
SMILES	COc1cc(CC2C(=O)OCC2Cc2ccc(OC)c(OC)c2)ccc1O
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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