ARCTIIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H34O11
Molecular Weight	534.5523
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC3=CC=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(OC)=C3)C=C1OC

InChI

InChIKey=XOJVHLIYNSOZOO-SWOBOCGESA-N

InChI=1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23691032
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18288407 https://www.ncbi.nlm.nih.gov/pubmed/15042601

Arctiin, isolated from Forsythia suspensa has been reported to have anti-inflammatory, anti-oxidant, antibacterial, and antiviral effects in vitro. It has been found to act as agonist of the adiponectin receptor 1. Has a potential role in the treatment of obesity. Arctiin has being shown to have anticancer effects in animal research.

Approval Year

Targets

Primary Target	Pharmacology	Potency
UDP-glucuronosyltransferase 2B15 1 Target ID: CHEMBL6161 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27145339	Inhibitor 8297	16.0 µM [Ki]
adipose tissue development 2 Target ID: GO:0060612 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25489405	Inhibitor 8297
endothelial cell proliferation 7 Target ID: GO:0001935 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24163109	Activator 1430
Adiponectin receptor protein 1 6 Target ID: CHEMBL3392946 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23691032	Agonist 2678	1.2 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21733191	Inhibitor 8297
G1/S-specific cyclin D1 1 Target ID: CHEMBL3610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18288407	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25489405	Primary	Basic research	Unknown Approved Use Unknown
Inflammatory diseases 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21733191	Primary	Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18288407	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Differential in vitro anti-HIV activity of natural lignans.	1990 Nov-Dec	1965681
Effects of the lignan, arctiin, on 17-beta ethinyl estradiol promotion of preneoplastic liver cell foci development in rats.	1998 Mar-Apr	9615764
Neuroprotective dibenzylbutyrolactone lignans of Torreya nucifera.	2001 Jul	11488466
Chemoprevention of heterocyclic amine-induced mammary carcinogenesis in rats.	2002	11921198
Simultaneous determination of chlorogenic acid, forsythin and arctiin in Chinese traditional medicines preparation by reversed phase-HPLC.	2003 Apr	12672997
Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria.	2003 Apr	12672988
Effects of forsythia fruit extracts and lignan on lipid metabolism.	2004	15630274
[Dyuamical studies on metabolic chemistry of lignans from seeds of Arctium lappa].	2005 Aug	16245912
Application of preparative high-speed counter-current chromatography for separation and purification of arctiin from Fructus Arctii.	2005 Jan 21	15700478
Isolation and identification of arctiin and arctigenin in leaves of burdock (Arctium lappa L.) by polyamide column chromatography in combination with HPLC-ESI/MS.	2005 Mar-Apr	15881114
Lack of significant modifying effect of arctiin on prostate carcinogenesis in probasin/SV40 T antigen transgenic rats.	2005 May 26	15863263
A high performance liquid chromatography method for the simultaneous determination of arctiin, chlorogenic acid and glycyrrhizin in a Chinese proprietary medicine.	2005 Sep 15	15946817
A new lignan glycoside from the stem bark of Styrax japonica S. et Z.	2007 Apr	17489357
The chemopreventive effects of Saussurea salicifolia through induction of apoptosis and phase II detoxification enzyme.	2007 Dec	18057725
Microemulsion electrokinetic chromatography for the separation of arctiin and arctigenin in Fructus Arctii and its herbal preparations.	2007 Dec 1	17988959
Antiviral activity of berberine and related compounds against human cytomegalovirus.	2007 Mar 15	17239594
Arctiin induces cell growth inhibition through the down-regulation of cyclin D1 expression.	2008 Mar	18288407
Bioassay-guided isolation and identification of active compounds from Fructus Arctii against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus).	2009 Dec	19859737
Ameliorative effects of arctiin from Arctium lappa on experimental glomerulonephritis in rats.	2009 Nov	19524415
Mass fragmentation study of the trimethylsilyl derivatives of arctiin, matairesinoside, arctigenin, phylligenin, matairesinol, pinoresinol and methylarctigenin: their gas and liquid chromatographic analysis in plant extracts.	2010 Mar 5	20137791

Patents

Sample Use Guides

In Vivo Use Guide

STZ-induced diabetic rats were treated with arctiin at the dosage of 60 or 40 mg/kg/day via intraperitoneal injection for 8 weeks.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Arctiin treatment of 3T3-L1 pre-adipocytes markedly decreased adipogenesis in a dose-dependent manner (12.5 to 100 uM).

Name

Type

Language

ARCTIIN

Official Name

English

ARCTIGENIN-4-GLUCOSIDE

Common Name

English

NSC-315527

Code

English

2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)-3-((4-(.BETA.-D-GLUCOPYRANOSYLOXY)-3-METHOXYPHENYL)METHYL)DIHYDRO-, (3R-TRANS)-

Common Name

English

2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)-3-((4-(.BETA.-D-GLUCOPYRANOSYLOXY)-3-METHOXYPHENYL)METHYL)DIHYDRO-, (3R,4R)-

Common Name

English

ARCTII

Common Name

English

ARCTIIN [INCI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1145