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(OC)=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=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 8504	16.0 µM [Ki]
adipose tissue development 2 Target ID: GO:0060612 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25489405	Inhibitor 8504
endothelial cell proliferation 8 Target ID: GO:0001935 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24163109	Activator 1447
Adiponectin receptor protein 1 6 Target ID: CHEMBL3392946 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23691032	Agonist 2752	1.2 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21733191	Inhibitor 8504
G1/S-specific cyclin D1 1 Target ID: CHEMBL3610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18288407	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Obesity 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25489405	Primary	Basic research	Unknown Approved Use Unknown
Inflammatory diseases 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21733191	Primary	Basic research	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18288407	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria.	2010-11	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.	2010-10-15	20810325
On-line coupling of counter-current chromatography and macroporous resin chromatography for continuous isolation of arctiin from the fruit of Arctium lappa L.	2010-08-13	20619844
Production of enterodiol from defatted flaxseeds through biotransformation by human intestinal bacteria.	2010-04-16	20398397
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.	2010-03-05	20137791
Metabolic profile of the bioactive compounds of burdock (Arctium lappa) seeds, roots and leaves.	2010-01-20	19375261
Lignans inhibit cell growth via regulation of Wnt/beta-catenin signaling.	2010-01-04	20510325
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
Bioassay-guided isolation and identification of active compounds from Fructus Arctii against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus).	2009-12	19859737
Ameliorative effects of arctiin from Arctium lappa on experimental glomerulonephritis in rats.	2009-11	19524415
Further studies on a human intestinal bacterium Ruminococcus sp. END-1 for transformation of plant lignans to mammalian lignans.	2009-08-26	19630415
Natural Arctium lappa fruit extract improves the clinical signs of aging skin.	2008-12	19146605
In vitro and in vivo anti-allergic effects of Arctium lappa L.	2008-11	18703753
Treatment with SI000413, a new herbal formula, ameliorates murine collagen-induced arthritis.	2008-07	18591771
Arctiin induces cell growth inhibition through the down-regulation of cyclin D1 expression.	2008-03	18288407
Microemulsion electrokinetic chromatography for the separation of arctiin and arctigenin in Fructus Arctii and its herbal preparations.	2007-12-01	17988959
The chemopreventive effects of Saussurea salicifolia through induction of apoptosis and phase II detoxification enzyme.	2007-12	18057725
Inhibitory effect of nordihydroguaiaretic acid, a plant lignan, on Helicobacter pylori-associated gastric carcinogenesis in Mongolian gerbils.	2007-11	17894552
Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone.	2007-05	17473433
A new lignan glycoside from the stem bark of Styrax japonica S. et Z.	2007-04	17489357
Antiviral activity of berberine and related compounds against human cytomegalovirus.	2007-03-15	17239594
[Relative adscriptions of components in the effective fractions of Yinqiao decoction and its composing individual herbs].	2007-02	17518050
In-vitro and in-vivo anti-inflammatory action of the ethanol extract of Trachelospermi caulis.	2007-01	17227629
Lack of a significant effect of arctiin on development of 7,12-dimethylbenz(a)anthracene-induced mammary tumors in ovariectomized Sprague-Dawley rats.	2007	17571954
Americanin, a bioactive dibenzylbutyrolactone lignan, from the seeds of Centaurea americana.	2006-11	16996096
[Study on condition for extraction of arctiin from fruits of Arctium lappa using supercritical fluid extraction].	2006-08	17048565
Determination of phillyrin in rat plasma by high-performance liquid chromatography and its application to pharmacokinetic studies.	2006-05-03	16413739
Arctigenin from Fructus Arctii is a novel suppressor of heat shock response in mammalian cells.	2006	16817321
A high performance liquid chromatography method for the simultaneous determination of arctiin, chlorogenic acid and glycyrrhizin in a Chinese proprietary medicine.	2005-09-15	15946817
[Dyuamical studies on metabolic chemistry of lignans from seeds of Arctium lappa].	2005-08	16245912
Lack of significant modifying effect of arctiin on prostate carcinogenesis in probasin/SV40 T antigen transgenic rats.	2005-05-26	15863263
Isolation and identification of arctiin and arctigenin in leaves of burdock (Arctium lappa L.) by polyamide column chromatography in combination with HPLC-ESI/MS.	2005-05-11	15881114
Application of preparative high-speed counter-current chromatography for separation and purification of arctiin from Fructus Arctii.	2005-01-21	15700478
The content of lignan glycosides in Forsythia flowers and leaves.	2004-12-04	15575593
Isolation and identification of biologically active compounds from Forsythia viridissima flowers.	2004-10-16	15481244
[Clinical observation on treatment of diabetic nephropathy with compound fructus arctii mixture].	2004-07	15307694
Modulation of anti-adhesion molecule MUC-1 is associated with arctiin-induced growth inhibition in PC-3 cells.	2004-05-15	15042601
Effects of forsythia fruit extracts and lignan on lipid metabolism.	2004	15630274
Lack of significant inhibitory effects of a plant lignan tracheloside on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-induced mammary carcinogenesis in female Sprague-Dawley rats.	2003-10-28	14568166
Simultaneous determination of chlorogenic acid, forsythin and arctiin in Chinese traditional medicines preparation by reversed phase-HPLC.	2003-04	12672997
Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria.	2003-04	12672988
[Isolation and elucidation of chemical constituents with antiviral action from yinqiaosan on influenza virus].	2003-01	15015266
Chemoprevention of heterocyclic amine-induced mammary carcinogenesis in rats.	2002	11921198
Neuroprotective dibenzylbutyrolactone lignans of Torreya nucifera.	2001-07	11488466
Effects of the lignan, arctiin, on 17-beta ethinyl estradiol promotion of preneoplastic liver cell foci development in rats.	1998-06-06	9615764
Differential in vitro anti-HIV activity of natural lignans.	1990-11-01	1965681

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 `Mon Mar 31 20:05:22 GMT 2025` Edited by `admin` on `Mon Mar 31 20:05:22 GMT 2025`
Record UNII	TM5RQ949K7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARCTIIN

Official Name

English

NSC-315527

Preferred Name

English

ARCTIGENIN-4-GLUCOSIDE

Common Name

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

Classification Tree Code System Code

NCI_THESAURUS

C1145