AdipoGen Life Sciences

(-)-Arctigenin

CHF 50.00
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AG-CN2-0530-M01010 mgCHF 50.00
AG-CN2-0530-M05050 mgCHF 150.00
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Product Details
Synonyms (3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(3H)-furanone
Product Type Chemical
Properties
Formula

C21H24O6

MW 372.4
CAS 7770-78-7
RTECS LY9247000
Source/Host Chemicals Semi-synthetic.
Purity Chemicals ≥99% (HPLC)
Appearance Colorless crystals.
Solubility Soluble in DMSO (20mg/ml) or DMF (20mg/ml). Slightly soluble in ethanol or methanol (both ~1mg/ml). Insoluble in water.
Identity Determined by 1H-NMR and MS.
InChi Key NQWVSMVXKMHKTF-JKSUJKDBSA-N
Smiles O=C1OC[C@H](CC2=CC(OC)=C(OC)C=C2)[C@H]1CC3=CC(OC)=C(O)C=C3
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Aglycone metabolite of (-)-Arctiin (AG-CN2-0532), isolated from Arctium lappa.
  • Multifunctional natural compound with antioxidant, antibacterial, anti-inflammatory, antidiabetic, neuroprotective, antiproliferative and antiviral activities.
  • Natural agonist of the PP2A that has potent renoprotective effects in type 1 and type 2 diabetic animal models.
  • Inhibits adipogenesis through AMPK induction.
  • Modulator of peroxisome proliferator-activated receptor γ (PPARγ).
  • Inhibits LPS-induced iNOS expression via inhibition of IκBα phosphorylation and p65 nuclear translocation.
  • Inhibits NLRP3 in a SIRT1-dependent manner.
  • HIV-1 integrase/replication inhibitor in vitro.
  • Potently inhibits MKK1 (MEK1).
  • Blocks the activation of Akt induced by glucose starvation in pancreatic cancer PANC-1 cells. Also dissipates the mitochondrial membrane potential by inhibition of the mitochondrial complexes II and IV. Selectively kills only the OXPHOS-dependent PANC-1 cells. Possibly useful in immunometabolism research.
  • Shown to induce cell cycle arrest, autophagy and apoptosis in several cancer cell lines and having chemosensitizing properties.
Product References
  1. (-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase: E. Eich, et al.; J. Med. Chem. 39, 86 (1996)
  2. Identification of arctigenin as an antitumor agent having the ability to eliminate the tolerance of cancer cells to nutrient starvation: S. Awale, et al.; Cancer Res. 66, 1751 (2006)
  3. In vitro anti-inflammatory effects of arctigenin, a lignan from Arctium lappa L., through inhibition on iNOS pathway: F. Zhao, et al.; J. Ethnopharmacol. 122, 457 (2009)
  4. Arctigenin, a phenylpropanoid dibenzylbutyrolactone lignan, inhibits type I-IV allergic inflammation and pro-inflammatory enzymes: J.Y Lee & C.J. Kim; Arch. Pharm. Res. 33, 947 (2010)
  5. Arctigenin, a natural compound, activates AMP-activated protein kinase via inhibition of mitochondria complex I and ameliorates metabolic disorders in ob/ob mice: S.L. Huang, et al.; Diabetologia 55, 1469 (2012)
  6. Arctigenin preferentially induces tumor cell death under glucose deprivation by inhibiting cellular energy metabolism: Y. Gu, et al.; Biochem. Pharmacol. 84, 468 (2012)
  7. Arctigenin ameliorates inflammation in vitro and in vivo by inhibiting the PI3K/AKT pathway and polarizing M1 macrophages to M2-like macrophages: S.R. Hyam, et al.; Eur. J. Pharmacol. 708, 21 (2013)
  8. Inhibition of angiogenesis: a novel antitumor mechanism of the herbal compound arctigenin: Y. Gu, et al.; Anticancer Drugs 24, 781 (2013)
  9. Arctigenin effectively ameliorates memory impairment in Alzheimer's disease model mice targeting both β-amyloid production and clearance: Z. Zhu, et al.; J. Neurosci. 33, 13138 (2013)
  10. (-)-Arctigenin as a lead compound for anticancer agent: G.R. Chen, et al.; Nat. Prod. Res. 27, 2251 (2013)
  11. Arctigenin Inhibits Adipogenesis by Inducing AMPK Activation and Reduces Weight Gain in High-Fat Diet-Induced Obese Mice: Y.H. Han, et al.; J. Cell Biochem. 117, 2067 (2016)
  12. Inhibition of UDP-Glucuronosyltransferase (UGT) Isoforms by Arctiin and Arctigenin: H. Zhang, et al.; Phytother. Res. 30, 1189 (2016)
  13. Arctigenin functions as a selective agonist of estrogen receptor β to restrict mTORC1 activation and consequent Th17 differentiation: X. Wu, et al.; Oncotarget 7, 83893 (2016)
  14. Mechanistic insights into selective killing of OXPHOS-dependent cancer cells by arctigenin: K. Brecht, et al.; Toxicol. In Vitro 40, 55 (2017)
  15. Arctigenin, a natural lignan compound, induces G0/G1 cell cycle arrest and apoptosis in human glioma cells: A. Maimaitili, et al.; Oncol. Lett. 13, 1007 (2017)
  16. Arctigenin attenuates ischemic stroke via SIRT1-dependent inhibition of NLRP3 inflammasome: S. Zhang, et al.; BBRC 493, 821 (2017)
  17. Arctigenin inhibits the activation of the mTOR pathway, resulting in autophagic cell death and decreased ER expression in ER-positive human breast cancer cells: T. Maxwell, et al.; Int. J. Oncol. 52, 1339 (2018)
  18. Molecular mechanisms of the action of Arctigenin in cancer: Y. He, et al.; Biomed. Pharmacother. 108, 403 (2018) (Review)
  19. Arctigenin ameliorates renal impairment and inhibits endoplasmic reticulum stress in diabetic db/db mice: J. Zhang, et al.; Life Sci. 223, 194 (2019)
  20. Arctigenin attenuates diabetic kidney disease through the activation of PP2A in podocytes: Y. Zhong, et al.; Nat. Commun. 10, 4523 (2019)
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