(-)-Arctigenin
Product Code: AG-CN2-0530
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0530-M010 | 10 mg | £50.00 |
Quantity:
| AG-CN2-0530-M050 | 50 mg | £130.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
(3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(3H)-furanone
Appearance:
Colorless crystals.
CAS:
7770-78-7
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.Protect from light.
InChi:
InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6- 17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1
InChiKey:
NQWVSMVXKMHKTF-JKSUJKDBSA-N
Long Description:
Chemical. CAS: 7770-78-7. Formula: C21H24O6. MW: 372.4. Semi-Synthetic. 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 gamma (PPARgamma). Inhibits LPS-induced iNOS expression via inhibition of IkappaBalpha 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.
MDL:
MFCD00870597
Molecular Formula:
C21H24O6
Molecular Weight:
372.4
Package Type:
Vial
Product 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 gamma (PPARgamma). Inhibits LPS-induced iNOS expression via inhibition of IkappaBalpha 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.
Purity:
>99% (HPLC)
SMILES:
O=C1OC[C@H](CC2=CC(OC)=C(OC)C=C2)[C@H]1CC3=CC(OC)=C(O)C=C3
Solubility Chemicals:
Soluble in DMSO (20mg/ml) or DMF (20mg/ml). Slightly soluble in ethanol or methanol (both ~1mg/ml). Insoluble in water.
Source / Host:
Semi-synthetic.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase: E. Eich, et al.; J. Med. Chem. 39, 86 (1996) | 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) | 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) | 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) | 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) | Arctigenin preferentially induces tumor cell death under glucose deprivation by inhibiting cellular energy metabolism: Y. Gu, et al.; Biochem. Pharmacol. 84, 468 (2012) | 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) | Inhibition of angiogenesis: a novel antitumor mechanism of the herbal compound arctigenin: Y. Gu, et al.; Anticancer Drugs 24, 781 (2013) | Arctigenin effectively ameliorates memory impairment in Alzheimer's disease model mice targeting both beta-amyloid production and clearance: Z. Zhu, et al.; J. Neurosci. 33, 13138 (2013) | (-)-Arctigenin as a lead compound for anticancer agent: G.R. Chen, et al.; Nat. Prod. Res. 27, 2251 (2013) | 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) | Inhibition of UDP-Glucuronosyltransferase (UGT) Isoforms by Arctiin and Arctigenin: H. Zhang, et al.; Phytother. Res. 30, 1189 (2016) | Arctigenin functions as a selective agonist of estrogen receptor beta to restrict mTORC1 activation and consequent Th17 differentiation: X. Wu, et al.; Oncotarget 7, 83893 (2016) | Mechanistic insights into selective killing of OXPHOS-dependent cancer cells by arctigenin: K. Brecht, et al.; Toxicol. In Vitro 40, 55 (2017) | 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) | Arctigenin attenuates ischemic stroke via SIRT1-dependent inhibition of NLRP3 inflammasome: S. Zhang, et al.; BBRC 493, 821 (2017) | 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) | Molecular mechanisms of the action of Arctigenin in cancer: Y. He, et al.; Biomed. Pharmacother. 108, 403 (2018) (Review) | Arctigenin ameliorates renal impairment and inhibits endoplasmic reticulum stress in diabetic db/db mice: J. Zhang, et al.; Life Sci. 223, 194 (2019) | Arctigenin attenuates diabetic kidney disease through the activation of PP2A in podocytes: Y. Zhong, et al.; Nat. Commun. 10, 4523 (2019)