arctiin
arctigenin-4-glucoside
 
Notes:
from fruits of arctium lappa l.
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(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one (Click)
CAS Number: 20362-31-6Picture of molecule
FDA UNII: TM5RQ949K7
Nikkaji Web: J82.956K
MDL: MFCD00870630
XlogP3-AA: 1.80 (est)
Molecular Weight: 534.55918000
Formula: C27 H34 O11
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidants
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 756.43 °C. @ 760.00 mm Hg (est)
Flash Point: 482.00 °F. TCC ( 250.10 °C. ) (est)
logP (o/w): -0.564 (est)
Soluble in:
 water, 190 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
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Suppliers:
Carbosynth
For experimental / research use only.
Arctiin
Changsha Organic Herb
Burdock Seed Extract Power 40% Arctiin
Coompo
For experimental / research use only.
Arctiin from Plants ≥95%
Odor: characteristic
Use: Arctiin and arctigenin have shown anticancer effects. Arctiin induces growth inhibition and dephosphorylates the tumor-suppressor retinoblastoma protein in human immortalized keratinocyte HaCaT cells. We also show that the growth inhibition caused by arctiin is associated with the down-regulation of cyclin D1 protein expression. Furthermore, the arctiin-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. Taken together, these results suggest that arctiin down-regulates cyclin D1 protein expression and that this at least partially contributes to the anti-proliferative effect of arctiin. Arctiin dose dependently decreased the production of NO and proinflammatory cytokines such as IL-1beta, IL-6, TNF-alpha, and PGE2, and it reduced the gene and protein levels as determined by RT-PCR and western blot analysis, respectively. The expression of co-stimulatory molecules such as B7-1 and B7-2 were also inhibited by arctiin. Furthermore, the activation of the nuclear transcription factor, NF-kappaB in macrophages was inhibited by arctiin. Taken together these results provide evidence of the bioactivity of arctiin in inflammatory diseases and suggest that arctiin may exert anti-inflammatory effect by inhibiting the pro-inflammatory mediators through the inactivation of NF-kappaB.
Santa Cruz Biotechnology
For experimental / research use only.
(-)-Arctiin
Sigma-Aldrich: Sigma
For experimental / research use only.
Arctiin ≥95% (LC/MS-ELSD)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antioxidants
Recommendation for arctiin usage levels up to:
 not for fragrance use.
 
Recommendation for arctiin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 100528
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
Chemidplus: 0020362316
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References:
 (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 100528
Pubchem (sid): 135058292
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C16915
HMDB (The Human Metabolome Database): Search
FooDB: FDB001444
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
EFSA Update of results on the monitoring of furan levels in food: Read Report
EFSA Previous report: Results on the monitoring of furan levels in food: Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food: Read Report
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 burdock fruit
Search Trop  Picture
 burdock plant
Search Trop  Picture
 burdock seed
Search Trop  Picture
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Synonyms:
 arctigenin-4-glucoside
(-)-arctiin
(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
2(3H)-furanone, 4-((3,4-dimethoxyphenyl)methyl)-3-((4-(β-D-glucopyranosyloxy)-3-methoxyphenyl)methyl)dihydro-, (3R-trans)-
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Articles:
PubMed: Arctiin inhibits adipogenesis in 3T3-L1 cells and decreases adiposity and body weight in mice fed a high-fat diet.
PubMed: Arctiin blocks hydrogen peroxide-induced senescence and cell death though microRNA expression changes in human dermal papilla cells.
PubMed: Photoprotective effect of arctiin against ultraviolet B-induced damage in HaCaT keratinocytes is mediated by microRNA expression changes.
PubMed: Optimization of extraction and purification of arctiin from Fructus arctii and its protection against glucose-induced rat aortic endothelial cell injury.
PubMed: Effect of arctiin on glomerular filtration barrier damage in STZ-induced diabetic nephropathy rats.
PubMed: Arctigenin but not arctiin acts as the major effective constituent of Arctium lappa L. fruit for attenuating colonic inflammatory response induced by dextran sulfate sodium in mice.
PubMed: Simultaneous determination of arctiin and its metabolites in rat urine and feces by HPLC.
PubMed: Arctiin induces an UVB protective effect in human dermal fibroblast cells through microRNA expression changes.
PubMed: [Determination of plasma protein binding rate of arctiin and arctigenin with ultrafiltration].
PubMed: Effects of arctiin on streptozotocin-induced diabetic retinopathy in Sprague-Dawley rats.
PubMed: Plasma pharmacokinetics and tissue distribution of arctiin and its main metabolite in rats by HPLC-UV and LC-MS.
PubMed: [Effect of arctiin on mouse podocyte epithelial-mesenchymal transition induced by advanced oxidation protein products].
PubMed: Anti-inflammatory function of arctiin by inhibiting COX-2 expression via NF-κB pathways.
PubMed: On-line coupling of counter-current chromatography and macroporous resin chromatography for continuous isolation of arctiin from the fruit of Arctium lappa L.
PubMed: Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza A virus.
PubMed: Ameliorative effects of arctiin from Arctium lappa on experimental glomerulonephritis in rats.
PubMed: Modulation of anti-adhesion molecule MUC-1 is associated with arctiin-induced growth inhibition in PC-3 cells.
PubMed: Effects of arctiin on PhIP-induced mammary, colon and pancreatic carcinogenesis in female Sprague-Dawley rats and MeIQx-induced hepatocarcinogenesis in male F344 rats.
PubMed: Arctiin induces cell growth inhibition through the down-regulation of cyclin D1 expression.
PubMed: Effects of the lignan, arctiin, on 17-beta ethinyl estradiol promotion of preneoplastic liver cell foci development in rats.
PubMed: 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.
PubMed: Lack of significant modifying effect of arctiin on prostate carcinogenesis in probasin/SV40 T antigen transgenic rats.
PubMed: Microemulsion electrokinetic chromatography for the separation of arctiin and arctigenin in Fructus Arctii and its herbal preparations.
PubMed: Application of preparative high-speed counter-current chromatography for separation and purification of arctiin from Fructus Arctii.
PubMed: Lack of a significant effect of arctiin on development of 7,12-dimethylbenz(a)anthracene-induced mammary tumors in ovariectomized Sprague-Dawley rats.
PubMed: Natural lignans from Arctium lappa modulate P-glycoprotein efflux function in multidrug resistant cancer cells.
PubMed: Determination of arctiin and arctigenin in Fructus Arctii by reverse-phase HPLC.
PubMed: [Study on condition for extraction of arctiin from fruits of Arctium lappa using supercritical fluid extraction].
PubMed: Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria.
PubMed: [Study on High-yield Cultivation Measures for Arctii Fructus].
PubMed: Isolation and identification of arctiin and arctigenin in leaves of burdock (Arctium lappa L.) by polyamide column chromatography in combination with HPLC-ESI/MS.
PubMed: Simultaneous determination of chlorogenic acid, forsythin and arctiin in Chinese traditional medicines preparation by reversed phase-HPLC.
PubMed: Chemical analysis of raw and processed Fructus arctii by high-performance liquid chromatography/diode array detection-electrospray ionization-mass spectrometry.
PubMed: Arctiin and onopordopicrin from Carduus micropterus ssp. perspinosus.
PubMed: A high performance liquid chromatography method for the simultaneous determination of arctiin, chlorogenic acid and glycyrrhizin in a Chinese proprietary medicine.
PubMed: Study on human intestinal bacterium Blautia sp. AUH-JLD56 for the conversion of arctigenin to (-)-3'-desmethylarctigenin.
PubMed: Optimum yields of dibenzylbutyrolactone-type lignans from Cynareae fruits, during their ripening, germination and enzymatic hydrolysis processes, determined by on-line chromatographic methods.
PubMed: [THE LIGNANE GLYCOSIDE ARCTIIN AS A CHEMOTAXONOMIC CHARACTERISTIC IN THE COMPOSITAE FAMILY].
PubMed: Alkyl and phenolic glycosides from Saussurea stella.
PubMed: [On the presence of lignan-glycosides in the Forsythia family. 1. Isolation of phillyrin and arctiin].
PubMed: Standardization of solvent extracts from Onopordum acanthium fruits by GC-MS, HPLC-UV/DAD, HPLC-TQMS and 1H-NMR and evaluation of their inhibitory effects on the expression of IL-8 and E-selectin in immortalized endothelial cells (HUVECtert).
PubMed: 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.
PubMed: Natural lignans from Arctium lappa as antiaging agents in Caenorhabditis elegans.
PubMed: Arctigenin isolated from the seeds of Arctium lappa ameliorates memory deficits in mice.
PubMed: [Study on correlation between ITS sequence of Arctium lappa and quality of Fructus Arctii].
PubMed: Optimization of the processing technology of Fructus Arctii by response surface methodology.
PubMed: Arctigenin from Fructus Arctii (Seed of Burdock) Reinforces Intestinal Barrier Function in Caco-2 Cell Monolayers.
PubMed: Determination of the major constituents in fruit of Arctium lappa L. by matrix solid-phase dispersion extraction coupled with HPLC separation and fluorescence detection.
PubMed: Searching for synergistic bronchodilators and novel therapeutic regimens for chronic lung diseases from a traditional Chinese medicine, Qingfei Xiaoyan Wan.
PubMed: Lignans inhibit cell growth via regulation of Wnt/beta-catenin signaling.
PubMed: Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay.
PubMed: Structural transformation of lignan compounds in rat gastrointestinal tract; II. Serum concentration of lignans and their metabolites.
PubMed: Anti-austeric activity of phenolic constituents of seeds of Arctium lappa.
PubMed: Arctigenin ameliorates inflammation in vitro and in vivo by inhibiting the PI3K/AKT pathway and polarizing M1 macrophages to M2-like macrophages.
PubMed: Complementary fragmentation pattern analysis by gas chromatography-mass spectrometry and liquid chromatography tandem mass spectrometry confirmed the precious lignan content of Cirsium weeds.
PubMed: Induction of caspase-8 and death receptors by a new dammarane skeleton from the dried fruits of Forsythia koreana.
PubMed: Metabolic profile of the bioactive compounds of burdock (Arctium lappa) seeds, roots and leaves.
PubMed: Ligand binding affinities of arctigenin and its demethylated metabolites to estrogen receptor alpha.
PubMed: Antiasthmatic action of dibenzylbutyrolactone lignans from fruits of Forsythia viridissima on asthmatic responses to ovalbumin challenge in conscious guinea-pigs.
PubMed: [Trace chemical constituents contained in Trachelospermum jasminoides and structure identification].
PubMed: Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria.
PubMed: Further studies on a human intestinal bacterium Ruminococcus sp. END-1 for transformation of plant lignans to mammalian lignans.
PubMed: Metabolism of ginsenoside Rb1 by human intestinal microflora and cloning of its metabolizing β-D-glucosidase from Bifidobacterium longum H-1.
PubMed: Bioassay-guided isolation and identification of active compounds from Fructus Arctii against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus).
PubMed: Effects of forsythia fruit extracts and lignan on lipid metabolism.
PubMed: The content of lignan glycosides in Forsythia flowers and leaves.
PubMed: Biological activities of Fructus arctii fermented with the basidiomycete Grifola frondosa.
PubMed: Structural transformation of lignan compounds in rat gastrointestinal tract.
PubMed: Cytotoxic components of bardanae fructus (goboshi).
PubMed: [Relative adscriptions of components in the effective fractions of Yinqiao decoction and its composing individual herbs].
PubMed: [Isolation and elucidation of chemical constituents with antiviral action from yinqiaosan on influenza virus].
PubMed: Natural Arctium lappa fruit extract improves the clinical signs of aging skin.
PubMed: Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone.
PubMed: Chemoprevention of heterocyclic amine-induced mammary carcinogenesis in rats.
PubMed: Americanin, a bioactive dibenzylbutyrolactone lignan, from the seeds of Centaurea americana.
PubMed: 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.
PubMed: The chemopreventive effects of Saussurea salicifolia through induction of apoptosis and phase II detoxification enzyme.
PubMed: Inhibitory effect of nordihydroguaiaretic acid, a plant lignan, on Helicobacter pylori-associated gastric carcinogenesis in Mongolian gerbils.
PubMed: A new lignan glycoside from the stem bark of Styrax japonica S. et Z.
PubMed: [Dyuamical studies on metabolic chemistry of lignans from seeds of Arctium lappa].
PubMed: Neuroprotective dibenzylbutyrolactone lignans of Torreya nucifera.
PubMed: Anti-tumor-promoting activity of lignans from the aerial part of Saussurea medusa.
PubMed: [Studies on the chemical constituents of Arctium lappa L].
PubMed: In vitro and in vivo anti-allergic effects of Arctium lappa L.
PubMed: Treatment with SI000413, a new herbal formula, ameliorates murine collagen-induced arthritis.
PubMed: In-vitro and in-vivo anti-inflammatory action of the ethanol extract of Trachelospermi caulis.
PubMed: Arctigenin from Fructus Arctii is a novel suppressor of heat shock response in mammalian cells.
PubMed: Determination of phillyrin in rat plasma by high-performance liquid chromatography and its application to pharmacokinetic studies.
PubMed: Isolation and identification of biologically active compounds from Forsythia viridissima flowers.
PubMed: [Clinical observation on treatment of diabetic nephropathy with compound fructus arctii mixture].
PubMed: Lignans and Other Constituents of Centaurea sphaerocephala ssp. polyacantha.
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