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

Molecular Formula	C27H34O11
Molecular Weight	534.5523
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Chemoprevention of heterocyclic amine-induced mammary carcinogenesis in rats.	2002	11921198
[Clinical observation on treatment of diabetic nephropathy with compound fructus arctii mixture].	2004 Jul	15307694
The content of lignan glycosides in Forsythia flowers and leaves.	2004 Jul-Aug	15575593
Modulation of anti-adhesion molecule MUC-1 is associated with arctiin-induced growth inhibition in PC-3 cells.	2004 May 15	15042601
[Dyuamical studies on metabolic chemistry of lignans from seeds of Arctium lappa].	2005 Aug	16245912
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
[Study on condition for extraction of arctiin from fruits of Arctium lappa using supercritical fluid extraction].	2006 Aug	17048565
Americanin, a bioactive dibenzylbutyrolactone lignan, from the seeds of Centaurea americana.	2006 Nov	16996096
A new lignan glycoside from the stem bark of Styrax japonica S. et Z.	2007 Apr	17489357
[Relative adscriptions of components in the effective fractions of Yinqiao decoction and its composing individual herbs].	2007 Feb	17518050
Antiviral activity of berberine and related compounds against human cytomegalovirus.	2007 Mar 15	17239594
Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone.	2007 May	17473433
Arctiin induces cell growth inhibition through the down-regulation of cyclin D1 expression.	2008 Mar	18288407
In vitro and in vivo anti-allergic effects of Arctium lappa L.	2008 Nov	18703753
Bioassay-guided isolation and identification of active compounds from Fructus Arctii against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus).	2009 Dec	19859737
Dibenzylbutyrolactone lignans from Forsythia koreana fruits attenuate lipopolysaccharide-induced inducible nitric oxide synthetase and cyclooxygenase-2 expressions through activation of nuclear factor-κb and mitogen-activated protein kinase in RAW264.7 cells.	2010	21048310
Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza A virus.	2010	20606313
Production of enterodiol from defatted flaxseeds through biotransformation by human intestinal bacteria.	2010 Apr 16	20398397
On-line coupling of counter-current chromatography and macroporous resin chromatography for continuous isolation of arctiin from the fruit of Arctium lappa L.	2010 Aug 13	20619844
Lignans inhibit cell growth via regulation of Wnt/beta-catenin signaling.	2010 Aug-Sep	20510325
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
Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria.	2010 Nov	21031625
Determination of the major constituents in fruit of Arctium lappa L. by matrix solid-phase dispersion extraction coupled with HPLC separation and fluorescence detection.	2010 Oct 15	20810325

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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:15:09 GMT 2023` Edited by `admin` on `Fri Dec 15 20:15:09 GMT 2023`
Record UNII	TM5RQ949K7
Record Status	`Validated (UNII)`
Record Version

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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