Arctiin

• CAT Number: I002570
• CAS Number: 20362-31-6
• Molecular Formula: C27H34O11
• Molecular Weight: 534.6
• Purity: ≥95%
• Target: Others
• Solubility: DMSO: ≥ 5.4 mg/mL
• Storage: -20°C
• 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
• SMILES: COC1=C(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)C=CC(C[C@H]([C@@H](CC3=CC(OC)=C(OC)C=C3)CO4)C4=O)=C1

Arctiin(NSC 315527), a plant lignan that can be extracted from the Arctium lappa (burdock) seeds, is a possible environmental endocrine disruptor compounds and have been shown to influence sex hormone metabolism as well as protein synthesis, steroid biosynthesis.IC50 Value:Target: Othersin vitro: Treatment of PC-3 cells with arctiin decreased the cell number in a concentration- and time-dependent manner in serum-containing condition. Arctiin preferentially induced cell detachment, but did not have anti-proliferation or cytotoxic effects in PC-3 cells. The arctiin-induced effect was inhibited by cycloheximide, indicating that protein synthesis was required [1]. Although arctiin, the active component of AL that has been described in the literature, was not able to reduce degranulation in RBL-2H3 cells, a single high-performance liquid chromatography (HPLC) fraction from the AL extract inhibited beta-hexosaminidase release (IC(50) = 22.2 microg/ml) [2]. The growth inhibition caused by arctiin is associated with the down-regulation of cyclin D1 protein expression. Furthermore, thearctiin-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 [6].in vivo: Histopathological evaluation of prostate revealed that all the rats in any group developed adenocarcinoma in dorsolateral lobe of prostate, except two rats in 0.1% arctiin treated and one rat in 0.002% arctiin treated groups without prostate adenocarcinoma development [3]. After oral administration of arctiin (30, 60, 120 mg/kgd) for three weeks, the levels of serum creatinine (Scr) and blood urea nitrogen (BUN) and 24-h urine protein content markedly decreased, while endogenous creatinine clearance rate (ECcr) significantly increased [4]. STZ-induced diabetic rats were treated witharctiin at the dosage of 60 or 40 mg/kg/day via intraperitoneal injection for 8 weeks. Blood glucose and 24-h urinary albumin content were measured, and kidney histopathological changes were monitored [5].

Reference

1:Room temperature ionic liquids-based salting-in strategy for counter-current chromatography in the separation of arctiin. Wang Y, Zhang L, Wang D, Guo X, Wu S.J Chromatogr A. 2016 Dec 23;1478:26-34. doi: 10.1016/j.chroma.2016.11.028. Epub 2016 Nov 30. PMID: 27932083 2:[Arctiin ameliorates advanced oxidation protein product-induced epithelial-to- mesenchymal transition in HK-2 cells by inhibiting endoplasmic reticulum stress]. Zhang J, Huang LL, Liang XJ, Wang Y, Duan N, Xiang XH, Shu SS, Guo TT, Yang L, Tang X.Nan Fang Yi Ke Da Xue Xue Bao. 2016 Jun;36(6):833-7. Chinese. PMID: 27320888 3:Inhibition of UDP-Glucuronosyltransferase (UGT) Isoforms by Arctiin and Arctigenin. Zhang H, Zhao Z, Wang T, Wang Y, Cui X, Zhang H, Fang ZZ.Phytother Res. 2016 Jul;30(7):1189-96. doi: 10.1002/ptr.5627. Epub 2016 May 4. PMID: 27145339 4:Microwave-Assisted Extraction and Purification of Arctiin and Arctigenin from Fructus Arctii by High-Speed Countercurrent Chromatography. Lü H, Sun Z, Shan H, Song J.J Chromatogr Sci. 2016 Mar;54(3):472-8. doi: 10.1093/chromsci/bmv168. Epub 2015 Nov 20. PMID: 26590235 5:Arctiin inhibits adipogenesis in 3T3-L1 cells and decreases adiposity and body weight in mice fed a high-fat diet. Min B, Lee H, Song JH, Han MJ, Chung J.Nutr Res Pract. 2014 Dec;8(6):655-61. doi: 10.4162/nrp.2014.8.6.655. Epub 2014 Oct 15. PMID: 25489405 Free PMC Article6:Arctiin blocks hydrogen peroxide-induced senescence and cell death though microRNA expression changes in human dermal papilla cells. Bae S, Lim KM, Cha HJ, An IS, Lee JP, Lee KS, Lee GT, Lee KK, Jung HJ, Ahn KJ, An S.Biol Res. 2014 Sep 30;47:50. doi: 10.1186/0717-6287-47-50. PMID: 25299961 Free PMC Article7: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. Wu X, Yang Y, Dou Y, Ye J, Bian D, Wei Z, Tong B, Kong L, Xia Y, Dai Y.Int Immunopharmacol. 2014 Dec;23(2):505-15. doi: 10.1016/j.intimp.2014.09.026. Epub 2014 Oct 3. PMID: 25284342 8:Photoprotective effect of arctiin against ultraviolet B-induced damage in HaCaT keratinocytes is mediated by microRNA expression changes. Cha HJ, Lee GT, Lee KS, Lee KK, Hong JT, Lee NK, Kim SY, Lee BM, An IS, Hahn HJ, Ahn KJ, Lee SJ, An S, Bae S.Mol Med Rep. 2014 Sep;10(3):1363-70. doi: 10.3892/mmr.2014.2326. Epub 2014 Jun 13. PMID: 24926940 9:Arctiin induces an UVB protective effect in human dermal fibroblast cells through microRNA expression changes. Lee GT, Cha HJ, Lee KS, Lee KK, Hong JT, Ahn KJ, An IS, An S, Bae S.Int J Mol Med. 2014 Mar;33(3):640-8. doi: 10.3892/ijmm.2014.1616. Epub 2014 Jan 7. PMID: 24398562 10:Optimization of extraction and purification of arctiin from Fructus arctii and its protection against glucose-induced rat aortic endothelial cell injury. Lu LC, Zhang R, Song MB, Zhou SW, Qian GS.Cell Biochem Biophys. 2014 May;69(1):93-101. doi: 10.1007/s12013-013-9775-5. PMID: 24163109