CAS 20362-31-6|Arctiin

Introduction：Basic information about CAS 20362-31-6|Arctiin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Arctiin BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles29
6. Synonyms

Common Name	Arctiin
CAS Number	20362-31-6	Molecular Weight	534.552
Density	1.4±0.1 g/cm3	Boiling Point	756.4±60.0 °C at 760 mmHg
Molecular Formula	C₂₇H₃₄O₁₁	Melting Point	109 °C
MSDS	ChineseUSA	Flash Point	250.1±26.4 °C

Names

Name	Arctiin
Synonym	More Synonyms

Arctiin BiologicalActivity

Description	Arctiin(NSC 315527), a plant lignan that can be extracted from the Arctium lappa (burdock) seeds, is a possible environmental endocrine disruptor compounds and have been shown to influence sex hormone metabolism as well as protein synthesis, steroid biosynthesis. IC50 Value:Target: Othersin vitro: Treatment of PC-3 cells with arctiin decreased the cell number in a concentration- and time-dependent manner in serum-containing condition. Arctiin preferentially induced cell detachment, but did not have anti-proliferation or cytotoxic effects in PC-3 cells. The arctiin-induced effect was inhibited by cycloheximide, indicating that protein synthesis was required [1]. Although arctiin, the active component of AL that has been described in the literature, was not able to reduce degranulation in RBL-2H3 cells, a single high-performance liquid chromatography (HPLC) fraction from the AL extract inhibited beta-hexosaminidase release (IC(50) = 22.2 microg/ml) [2]. The growth inhibition caused by arctiin is associated with the down-regulation of cyclin D1 protein expression. Furthermore, thearctiin-induced suppression of cyclin D1 protein expression occurs in various types of human tumor cells, including osteosarcoma, lung, colorectal, cervical and breast cancer, melanoma, transformed renal cells and prostate cancer. Depletion of the cyclin D1 protein using small interfering RNA-rendered human breast cancer MCF-7 cells insensitive to the growth inhibitory effects of arctiin, implicates cyclin D1 as an important target of arctiin [6]. in vivo: Histopathological evaluation of prostate revealed that all the rats in any group developed adenocarcinoma in dorsolateral lobe of prostate, except two rats in 0.1% arctiin treated and one rat in 0.002% arctiin treated groups without prostate adenocarcinoma development [3]. After oral administration of arctiin (30, 60, 120 mg/kgd) for three weeks, the levels of serum creatinine (Scr) and blood urea nitrogen (BUN) and 24-h urine protein content markedly decreased, while endogenous creatinine clearance rate (ECcr) significantly increased [4]. STZ-induced diabetic rats were treated witharctiin at the dosage of 60 or 40 mg/kg/day via intraperitoneal injection for 8 weeks. Blood glucose and 24-h urinary albumin content were measured, and kidney histopathological changes were monitored [5].
Related Catalog	Signaling Pathways >>Others >>OthersNatural Products >>PhenylpropanoidsResearch Areas >>Cancer
References	[1]. Huang DM, et al. Modulation of anti-adhesion molecule MUC-1 is associated with arctiin-induced growth inhibition in PC-3 cells. Prostate. 2004 May 15;59(3):260-7. [2]. Knipping K, et al. In vitro and in vivo anti-allergic effects of Arctium lappa L. Exp Biol Med (Maywood). 2008 Nov;233(11):1469-77. [3]. Zeng Y, et al. Lack of significant modifying effect of arctiin on prostate carcinogenesis in probasin/SV40 T antigen transgenic rats. Cancer Lett. 2005 May 26;222(2):145-51. [4]. Wu JG, et al. Ameliorative effects of arctiin from Arctium lappa on experimental glomerulonephritis in rats. Phytomedicine. 2009 Nov;16(11):1033-41. [5]. Ma ST, et al. Effect of arctiin on glomerular filtration barrier damage in STZ-induced diabetic nephropathy rats. Phytother Res. 2013 Oct;27(10):1474-80. [6]. Matsuzaki Y, et al. Arctiin induces cell growth inhibition through the down-regulation of cyclin D1 expression. Oncol Rep. 2008 Mar;19(3):721-7.

Description

Arctiin(NSC 315527), a plant lignan that can be extracted from the Arctium lappa (burdock) seeds, is a possible environmental endocrine disruptor compounds and have been shown to influence sex hormone metabolism as well as protein synthesis, steroid biosynthesis. IC50 Value:Target: Othersin vitro: Treatment of PC-3 cells with arctiin decreased the cell number in a concentration- and time-dependent manner in serum-containing condition. Arctiin preferentially induced cell detachment, but did not have anti-proliferation or cytotoxic effects in PC-3 cells. The arctiin-induced effect was inhibited by cycloheximide, indicating that protein synthesis was required [1]. Although arctiin, the active component of AL that has been described in the literature, was not able to reduce degranulation in RBL-2H3 cells, a single high-performance liquid chromatography (HPLC) fraction from the AL extract inhibited beta-hexosaminidase release (IC(50) = 22.2 microg/ml) [2]. The growth inhibition caused by arctiin is associated with the down-regulation of cyclin D1 protein expression. Furthermore, thearctiin-induced suppression of cyclin D1 protein expression occurs in various types of human tumor cells, including osteosarcoma, lung, colorectal, cervical and breast cancer, melanoma, transformed renal cells and prostate cancer. Depletion of the cyclin D1 protein using small interfering RNA-rendered human breast cancer MCF-7 cells insensitive to the growth inhibitory effects of arctiin, implicates cyclin D1 as an important target of arctiin [6]. in vivo: Histopathological evaluation of prostate revealed that all the rats in any group developed adenocarcinoma in dorsolateral lobe of prostate, except two rats in 0.1% arctiin treated and one rat in 0.002% arctiin treated groups without prostate adenocarcinoma development [3]. After oral administration of arctiin (30, 60, 120 mg/kgd) for three weeks, the levels of serum creatinine (Scr) and blood urea nitrogen (BUN) and 24-h urine protein content markedly decreased, while endogenous creatinine clearance rate (ECcr) significantly increased [4]. STZ-induced diabetic rats were treated witharctiin at the dosage of 60 or 40 mg/kg/day via intraperitoneal injection for 8 weeks. Blood glucose and 24-h urinary albumin content were measured, and kidney histopathological changes were monitored [5].

Related Catalog

Signaling Pathways >>Others >>OthersNatural Products >>PhenylpropanoidsResearch Areas >>Cancer

References

[1]. Huang DM, et al. Modulation of anti-adhesion molecule MUC-1 is associated with arctiin-induced growth inhibition in PC-3 cells. Prostate. 2004 May 15;59(3):260-7.

[2]. Knipping K, et al. In vitro and in vivo anti-allergic effects of Arctium lappa L. Exp Biol Med (Maywood). 2008 Nov;233(11):1469-77.

[3]. Zeng Y, et al. Lack of significant modifying effect of arctiin on prostate carcinogenesis in probasin/SV40 T antigen transgenic rats. Cancer Lett. 2005 May 26;222(2):145-51.

[4]. Wu JG, et al. Ameliorative effects of arctiin from Arctium lappa on experimental glomerulonephritis in rats. Phytomedicine. 2009 Nov;16(11):1033-41.

[5]. Ma ST, et al. Effect of arctiin on glomerular filtration barrier damage in STZ-induced diabetic nephropathy rats. Phytother Res. 2013 Oct;27(10):1474-80.

[6]. Matsuzaki Y, et al. Arctiin induces cell growth inhibition through the down-regulation of cyclin D1 expression. Oncol Rep. 2008 Mar;19(3):721-7.

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Boiling Point	756.4±60.0 °C at 760 mmHg
Melting Point	109 °C
Molecular Formula	C₂₇H₃₄O₁₁
Molecular Weight	534.552
Flash Point	250.1±26.4 °C
Exact Mass	534.210083
PSA	153.37000
LogP	0.23
Vapour Pressure	0.0±2.7 mmHg at 25°C
Index of Refraction	1.601
InChIKey	XOJVHLIYNSOZOO-SWOBOCGESA-N
SMILES	COc1ccc(CC2COC(=O)C2Cc2ccc(OC3OC(CO)C(O)C(O)C3O)c(OC)c2)cc1OC
Storage condition	?20°C

Safety Information

RIDADR	NONH for all modes of transport

Articles29

Plasma pharmacokinetics and tissue distribution of arctiin and its main metabolite in rats by HPLC-UV and LC-MS.

Planta Med. 78(8) , 800-6, (2012)

The pharmacokinetic profile of arctiin, the major active lignan in fruits of Arctium lappa L., was investigated. Its main meta"bolite arctigenin was identified by an LC-MS method, and an HPLC-UV techn...

Simultaneous determination of arctiin and its metabolites in rat urine and feces by HPLC.

Fitoterapia 86 , 6-12, (2013)

Arctiin, an important lignan compound in Fructus Arctii, has been reported to possess various kinds of bioactivities. Previous studies on the pharmacokinetic of arctiin after oral administration showe...

Effects of arctiin on streptozotocin-induced diabetic retinopathy in Sprague-Dawley rats.

Planta Med. 78(12) , 1317-23, (2012)

Diabetic retinopathy is one of the most common and severe complications of diabetes mellitus. Arctiin, a bioactive compound isolated from the dry seeds of Arctium lappa L., has been reported to have a...

Synonyms

MFCD00870630

Arctiin (8CI)

4-{[(3R,4R)-4-(3,4-Dimethoxybenzyl)-2-oxotetrahydro-3-furanyl]methyl}-2-methoxyphenyl β-D-glucopyranoside

Arctigenin-4-glucoside

Arctin

Arctlin

2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]-3-[[4-(b-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-, (3R,4R)-

Arctiin

4-{[(3R,4R)-4-(3,4-Dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl]methyl}-2-methoxyphenyl β-D-glucopyranoside

2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]-3-[[4-(β-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-, (3R,4R)-

Great Burdock Root Extract

NSC 315527

Acrctiin

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