(-)-Arctiin

AdipoGen Life Sciences
Product Code: AG-CN2-0532
CodeSizePrice
AG-CN2-0532-M01010 mg£30.00
Quantity:
AG-CN2-0532-M05050 mg£85.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
Arctigenin-4-glucoside; NSC 315527
Appearance:
Colorless crystals.
CAS:
20362-31-6
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.Protect from light.
InChi:
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
InChiKey:
XOJVHLIYNSOZOO-SWOBOCGESA-N
Long Description:
Chemical. CAS: 20362-31-6. Formula: C27H34O11. MW: 534.6. Isolated from Arctium lappa. Metabolizes into (-)-Arctigenin (AG-CN2-0530). Multifunctional natural compound with photoprotective, anti-inflammatory, antidiabetic, antiproliferative and antiviral activities. Decreasing the production of nitric oxide and pro-inflammatory cytokines, such as IL-1beta, IL-6, TNF-alpha and PGE2 through the inhibition of PI3K/AKT/NF-kappaB signaling pathway. Suppresses cyclin D1 protein expression in multiple types of human tumor cells. Inhibitor of HIV-I integrase. Inhibits adipogenesis in 3T3-L1 adipocytes through the inhibition of PPARgamma and C/EBPalpha and the activation of AMPK signaling pathways. Photoprotective agent showing UVB protection in keratinocytes, which is mediated by miRNA responses and the suppression of UVB-induced cell death. Inhibitor of STAT3 phosphorylation at tyrosine 705 residue.
MDL:
MFCD00870630
Molecular Formula:
C27H34O11
Molecular Weight:
534.6
Package Type:
Vial
Product Description:
Metabolizes into (-)-Arctigenin (AG-CN2-0530). Multifunctional natural compound with photoprotective, anti-inflammatory, antidiabetic, antiproliferative and antiviral activities. Decreasing the production of nitric oxide and pro-inflammatory cytokines, such as IL-1beta, IL-6, TNF-alpha and PGE2 through the inhibition of PI3K/AKT/NF-kappaB signaling pathway. Suppresses cyclin D1 protein expression in multiple types of human tumor cells. Inhibitor of HIV-I integrase. Inhibits adipogenesis in 3T3-L1 adipocytes through the inhibition of PPARgamma and C/EBPalpha and the activation of AMPK signaling pathways. Photoprotective agent showing UVB protection in keratinocytes, which is mediated by miRNA responses and the suppression of UVB-induced cell death. Inhibitor of STAT3 phosphorylation at tyrosine 705 residue.
Purity:
>99% (HPLC)
SMILES:
O=C1OC[C@H](CC2=CC(OC)=C(OC)C=C2)[C@H]1CC3=CC(OC)=C(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4)C=C3
Solubility Chemicals:
Soluble in DMSO (20mg/ml), DMF (20mg/ml) or ethanol (1mg/ml). Insoluble in water.
Source / Host:
Isolated from Arctium lappa.
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

Anti-tumor-promoting activity of lignans from the aerial part of Saussurea medusa: M. Takasaki, et al.; Cancer Lett. 29, 158 (2000) | Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria: L.H. Xie, et al.; Chem. Pharm. Bull. 51, 378 (2003) | Arctiin induces cell growth inhibition through the down-regulation of cyclin D1 expression: Y. Matsuzaki, et al.; Oncol. Rep. 19, 721 (2008) | Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza A virus: K. Hayashi, et al.; Biol. Pharm. Bull. 33, 1199 (2010) | Anti-inflammatory function of arctiin by inhibiting COX-2 expression via NF-kappaB pathways: S. Lee, et al.; J. Inflamm. 8, 16 (2011) | Arctiin inhibits adipogenesis in 3T3-L1 cells and decreases adiposity and body weight in mice fed a high-fat diet: B. Min, et al.; Nutr. Res. Pract. 8, 655 (2014) | Photoprotective effect of arctiin against ultraviolet B-induced damage in HaCaT keratinocytes is mediated by microRNA expression changes: H.J. Cha, et al.; Mol. Med. Rep. 10, 1363 (2014) | Arctiin protects against cardiac hypertrophy through inhibiting MAPKs and AKT signaling pathways: J. Li, et al.; J. Pharmacol. Sci. 135, 97 (2017) | Overview of the anti-inflammatory effects, pharmacokinetic properties and clinical efficacies of arctigenin and arctiin from Arctium lappa L: Q. Gao, et al.; Acta Pharmacol. Sin. 39, 787 (2018) | Arctiin Prevents LPS-Induced Acute Lung Injury via Inhibition of PI3K/AKT Signaling Pathway in Mice: B. Zhou, et al.; Inflammation 41, 2129 (2018) | Arctiin is a pharmacological inhibitor of STAT3 phosphorylation at tyrosine 705 residue and potentiates bortezomib-induced apoptotic and anti-angiogenic effects in human multiple myeloma cells: J.H. Lee, et al.; Phytomedicine 55, 282 (2019)