Home Other Building Blocks 7770-78-7
7770-78-7,MFCD00870597
Catalog No.:AA005GGK

7770-78-7 | Arctigenin

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1mg
98%
in stock  
$7.00   $5.00
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10mg
98%
in stock  
$12.00   $8.00
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50mg
98%
in stock  
$17.00   $12.00
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100mg
98%
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$33.00   $23.00
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250mg
98%
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$50.00   $35.00
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1g
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$121.00   $85.00
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5g
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$405.00   $284.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA005GGK
Chemical Name:
Arctigenin
CAS Number:
7770-78-7
Molecular Formula:
C21H24O6
Molecular Weight:
372.4117
MDL Number:
MFCD00870597
SMILES:
COc1cc(ccc1OC)C[C@H]1COC(=O)[C@@H]1Cc1ccc(c(c1)OC)O
Properties
Properties
 
Form:
Solid  
MP:
98.0 to 102.0 °C  
Solubility:
DMSO: 34 mg/mL with heating and sonicating, soluble  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
483  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
7  
XLogP3:
3.6  

Downstream Synthesis Route

[1]JournaloftheChemicalSocietyofPakistan,2014,vol.36,p.870-874

[2]Patent:US2015/93345,2015,A1.Locationinpatent:Paragraph0097-0101

[3]Phytochemistry,1990,vol.29,p.1971-1980

[4]Chemicalandpharmaceuticalbulletin,1980,vol.28,p.850-860

[5]ChemicalandPharmaceuticalBulletin,1993,vol.41,p.1774-1779

[6]ChemicalandPharmaceuticalBulletin,1996,vol.44,p.2300-2304

[1]Nishi,Kosuke;Nishimoto,Asuka;Nishiwaki,Hisashi;Sugahara,Takuya;Yamauchi,Satoshi[Bioorganicandmedicinalchemistryletters,2020,vol.30,#13]

[2]Brown,Eric;Daugan,Alain[Tetrahedron,1989,vol.45,#1,p.141-154]

[3]Butts,CraigP.;Collingridge,GrahamL.;Jane,DavidE.;Mallah,Shahida;Molnár,Elek;Rečnik,Lisa-Maria;Thatcher,RobertJ.;Willis,ChristineL.[OrganicandBiomolecularChemistry,2021,vol.19,#42,p.9154-9162]

[1]Shen,Sida;Zhuang,Jingjing;Chen,Yijia;Lei,Min;Chen,Jing;Shen,Xu;Hu,Lihong[BioorganicandMedicinalChemistry,2013,vol.21,#13,p.3882-3893]

[2]Umehara;Sugawa;Kuroyanagi;Ueno;Taki[ChemicalandPharmaceuticalBulletin,1993,vol.41,#10,p.1774-1779]

[3]Eich,Eckart;Pertz,Heinz;Kaloga,Macki;Schulz,Jutta;Fesen,MarkR.;Mazumder,Abhijit;Pommier,Yves[JournalofMedicinalChemistry,1996,vol.39,#1,p.86-95]

[4]Butts,CraigP.;Collingridge,GrahamL.;Jane,DavidE.;Mallah,Shahida;Molnár,Elek;Rečnik,Lisa-Maria;Thatcher,RobertJ.;Willis,ChristineL.[OrganicandBiomolecularChemistry,2021,vol.19,#42,p.9154-9162]

[1]Kudou,Naoki;Taniguchi,Akira;Sugimoto,Kenji;Matsuya,Yuji;Kawasaki,Masashi;Toyooka,Naoki;Miyoshi,Chika;Awale,Suresh;Dibwe,DyaFita;Esumi,Hiroyasu;Kadota,Shigetoshi;Tezuka,Yasuhiro[EuropeanJournalofMedicinalChemistry,2013,vol.60,p.76-88]

[2]Chen,Gui-Rong;Li,Hong-Fu;Dou,De-Qiang;Xu,Yu-Bin;Jiang,Hong-Shuai;Li,Fu-Rui;Kang,Ting-Guo[NaturalProductResearch,2013,vol.27,#23,p.2251-2255]

[3]Eich,Eckart;Pertz,Heinz;Kaloga,Macki;Schulz,Jutta;Fesen,MarkR.;Mazumder,Abhijit;Pommier,Yves[JournalofMedicinalChemistry,1996,vol.39,#1,p.86-95]

403-43-0    26687-82-1   
4-Fluoro-benzoicacid4-(3R,4R)-4-(3,4-dimethoxy-benzyl)-2-oxo-tetrahydro-furan-3-ylmethyl-2-methoxy-phenylester 

[1]BioorganicandMedicinalChemistry,2013,vol.21,p.3882-3893

[2]ChemicalandPharmaceuticalBulletin,1996,vol.44,p.2300-2304

Literature

Title: Arctigenin in combination with quercetin synergistically enhances the antiproliferative effect in prostate cancer cells.

Journal: Molecular nutrition & food research 20150201

Title: Tumor specific cytotoxicity of arctigenin isolated from herbal plant Arctium lappa L.

Journal: Journal of natural medicines 20121001

Title: Arctigenin promotes degradation of inducible nitric oxide synthase through CHIP-associated proteasome pathway and suppresses its enzyme activity.

Journal: International immunopharmacology 20121001

Title: Phytochemical profile and apoptotic activity of Onopordum cynarocephalum.

Journal: Planta medica 20121001

Title: Arctigenin preferentially induces tumor cell death under glucose deprivation by inhibiting cellular energy metabolism.

Journal: Biochemical pharmacology 20120815

Title: Arctigenin anti-tumor activity in bladder cancer T24 cell line through induction of cell-cycle arrest and apoptosis.

Journal: Anatomical record (Hoboken, N.J. : 2007) 20120801

Title: Arctigenin alleviates ER stress via activating AMPK.

Journal: Acta pharmacologica Sinica 20120701

Title: Antiausterity agents from Uvaria dac and their preferential cytotoxic activity against human pancreatic cancer cell lines in a nutrient-deprived condition.

Journal: Journal of natural products 20120622

Title: Arctigenin suppresses receptor activator of nuclear factor κB ligand (RANKL)-mediated osteoclast differentiation in bone marrow-derived macrophages.

Journal: European journal of pharmacology 20120505

Title: Arctigenin, a natural compound, activates AMP-activated protein kinase via inhibition of mitochondria complex I and ameliorates metabolic disorders in ob/ob mice.

Journal: Diabetologia 20120501

Title: New expectations from the well-known medicinal properties of Arctium lappa.

Journal: Diabetologia 20120501

Title: [Research on the preparative method of Arctigenin].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20120301

Title: Synthesis of (-)-arctigenin derivatives and their anticancer activity.

Journal: Natural product research 20120101

Title: Optimum yields of dibenzylbutyrolactone-type lignans from Cynareae fruits, during their ripening, germination and enzymatic hydrolysis processes, determined by on-line chromatographic methods.

Journal: Phytochemical analysis : PCA 20120101

Title: pH and temperature dual-sensitive liposome gel based on novel cleavable mPEG-Hz-CHEMS polymeric vaginal delivery system.

Journal: International journal of nanomedicine 20120101

Title: Arctigenin protects focal cerebral ischemia-reperfusion rats through inhibiting neuroinflammation.

Journal: Biological & pharmaceutical bulletin 20120101

Title: Arctigenin enhances chemosensitivity of cancer cells to cisplatin through inhibition of the STAT3 signaling pathway.

Journal: Journal of cellular biochemistry 20111001

Title: Arctigenin induces cell cycle arrest by blocking the phosphorylation of Rb via the modulation of cell cycle regulatory proteins in human gastric cancer cells.

Journal: International immunopharmacology 20111001

Title: Arctigenin isolated from the seeds of Arctium lappa ameliorates memory deficits in mice.

Journal: Planta medica 20110901

Title: Arctigenin inhibits lipopolysaccharide-induced iNOS expression in RAW264.7 cells through suppressing JAK-STAT signal pathway.

Journal: International immunopharmacology 20110801

Title: Cell and nuclear enlargement of SW480 cells induced by a plant lignan, arctigenin: evaluation of cellular DNA content using fluorescence microscopy and flow cytometry.

Journal: DNA and cell biology 20110801

Title: Arctigenin suppresses unfolded protein response and sensitizes glucose deprivation-mediated cytotoxicity of cancer cells.

Journal: Planta medica 20110101

Title: Arctigenin efficiently enhanced sedentary mice treadmill endurance.

Journal: PloS one 20110101

Title: Determination of the major constituents in fruit of Arctium lappa L. by matrix solid-phase dispersion extraction coupled with HPLC separation and fluorescence detection.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20101015

Title: Arctigenin blocks the unfolded protein response and shows therapeutic antitumor activity.

Journal: Journal of cellular physiology 20100701

Title: Arctigenin, a phenylpropanoid dibenzylbutyrolactone lignan, inhibits type I-IV allergic inflammation and pro-inflammatory enzymes.

Journal: Archives of pharmacal research 20100601

Title: Lignans inhibit cell growth via regulation of Wnt/beta-catenin signaling.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100101

Title: Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza A virus.

Journal: Biological & pharmaceutical bulletin 20100101

Title: Bioassay-guided isolation and identification of active compounds from Fructus Arctii against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus).

Journal: Parasitology research 20091201

Title: In vitro anti-inflammatory effects of arctigenin, a lignan from Arctium lappa L., through inhibition on iNOS pathway.

Journal: Journal of ethnopharmacology 20090421

Title: Cytotoxic activity of Ipomoea cairica.

Journal: Natural product research 20080615

Title: [Induction of apoptosis of the human leukemia cells by arctigenin and its mechanism of action].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20080501

Title: Anti-inflammatory activity of arctigenin from Forsythiae Fructus.

Journal: Journal of ethnopharmacology 20080305

Title: Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan.

Journal: The Journal of antimicrobial chemotherapy 20080301

Title: Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition.

Journal: Bioorganic & medicinal chemistry 20080101

Title: A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20071218

Title: Microemulsion electrokinetic chromatography for the separation of arctiin and arctigenin in Fructus Arctii and its herbal preparations.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20071201

Title: The chemopreventive effects of Saussurea salicifolia through induction of apoptosis and phase II detoxification enzyme.

Journal: Biological & pharmaceutical bulletin 20071201

Title: Inhibitory effect of nordihydroguaiaretic acid, a plant lignan, on Helicobacter pylori-associated gastric carcinogenesis in Mongolian gerbils.

Journal: Cancer science 20071101

Title: Lignan profile in seeds of modern and old Italian soft wheat (Triticum aestivum L.) cultivars as revealed by CE-MS analyses.

Journal: Electrophoresis 20071101

Title: [A comparative research on quality of Vitmin C Yinqiao tablets from different manufacturers].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20071101

Title: Bioactive secondary metabolites from Boesenbergia pandurata of Myanmar and their preferential cytotoxicity against human pancreatic cancer PANC-1 cell line in nutrient-deprived medium.

Journal: Journal of natural products 20071001

Title: Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone.

Journal: Biological & pharmaceutical bulletin 20070501

Title: Antiviral activity of berberine and related compounds against human cytomegalovirus.

Journal: Bioorganic & medicinal chemistry letters 20070315

Title: Arctigenin from Fructus Arctii is a novel suppressor of heat shock response in mammalian cells.

Journal: Cell stress & chaperones 20060601

Title: A preparative isolation and purification of arctigenin and matairesinol from Forsythia koreana by centrifugal partition chromatography.

Journal: Journal of separation science 20060301

Title: Identification of arctigenin as an antitumor agent having the ability to eliminate the tolerance of cancer cells to nutrient starvation.

Journal: Cancer research 20060201

Title: [Effect of anti-influenza virus of Arctigenin in vivo].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20051101

Title: [Dyuamical studies on metabolic chemistry of lignans from seeds of Arctium lappa].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050801

Title: Isolation and identification of arctiin and arctigenin in leaves of burdock (Arctium lappa L.) by polyamide column chromatography in combination with HPLC-ESI/MS.

Journal: Phytochemical analysis : PCA 20050101

Title: Arctigenin, a phenylpropanoid dibenzylbutyrolactone lignan, inhibits MAP kinases and AP-1 activation via potent MKK inhibition: the role in TNF-alpha inhibition.

Journal: International immunopharmacology 20041001

Title: Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products.

Journal: Organic letters 20040429

Title: Arctigenin protects cultured cortical neurons from glutamate-induced neurodegeneration by binding to kainate receptor.

Journal: Journal of neuroscience research 20020415

Title: Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid.

Journal: The Journal of organic chemistry 20020322

Title: Application of gradient-enhanced nuclear Overhauser effect spectroscopy GOESY) in the structure elucidation of plant secondary metabolites.

Journal: Phytochemical analysis : PCA 20010101

Title: (-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase.

Journal: Journal of medicinal chemistry 19960105

Title: Differential in vitro anti-HIV activity of natural lignans.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 19900101

Title: Awale S, et, al. Identification of arctigenin as an antitumor agent having the ability to eliminate the tolerance of cancer cells to nutrient starvation. Cancer Res. 2006 Feb 1;66(3):1751-7.

Title: Gao Q, et, al. Overview of the anti-inflammatory effects, pharmacokinetic properties and clinical efficacies of arctigenin and arctiin from Arctium lappa L. Acta Pharmacol Sin. 2018 May;39(5):787-801.

Title: Hayashi K, et, al. Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza A virus. Biol Pharm Bull. 2010;33(7):1199-205.

Title: Wei L, et, al. Arctigenin Exerts Neuroprotective Effect by Ameliorating Cortical Activities in Experimental Autoimmune Encephalomyelitis In Vivo. Front Immunol. 2021 Jul 19;12:691590.

Title: Maxwell T, et, al. Arctigenin inhibits the activation of the mTOR pathway, resulting in autophagic cell death and decreased ER expression in ER-positive human breast cancer cells. Int J Oncol. 2018 Apr;52(4):1339-1349.

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