Arctigenin | CAS#7770-78-7 | Anti-tumor agent

MedKoo Cat#: 600145 | Name: Arctigenin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Arctigenin is a lignan found in certain plants of the Asteraceae, including the greater burdock (Arctium lappa) and Saussurea heteromalla. It has shown antiviral and anticancer effects in vitro. It is the aglycone of arctiin. The use of arctigenin has been shown to be effective in a mouse model of Japanese encephalitis.

Chemical Structure

Arctigenin

CAS#7770-78-7 (parent)

Theoretical Analysis

MedKoo Cat#: 600145

Name: Arctigenin

CAS#: 7770-78-7 (parent)

Chemical Formula: C21H24O6

Exact Mass: 372.1573

Molecular Weight: 372.41

Elemental Analysis: C, 67.73; H, 6.50; O, 25.78

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 550.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Related CAS #

25488-59-9 (methyl ether) 26788-57-8 (mustard) 7770-78-7 (parent)

Synonym

Arctigenin; (−)-Arctigenin;

IUPAC/Chemical Name

(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3- [(4-hydroxy-3-methoxyphenyl)methyl]-2-tetrahydrofuranone

InChi Key

NQWVSMVXKMHKTF-JKSUJKDBSA-N

InChi Code

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

SMILES Code

O=C1OC[C@H](CC2=CC=C(OC)C(OC)=C2)[C@H]1CC3=CC=C(O)C(OC)=C3

Appearance

solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 372.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Xu X, Piao HN, Aosai F, Zeng XY, Cheng JH, Cui YX, Li J, Ma J, Piao HR, Jin X, Piao LX. Arctigenin protects against depression by inhibiting microglial activation and neuroinflammation via HMGB1/TLR4/NF-κB and TNF-α/TNFR1/NF-κB pathways. Br J Pharmacol. 2020 Nov;177(22):5224-5245. doi: 10.1111/bph.15261. Epub 2020 Oct 19. PMID: 32964428; PMCID: PMC7589024. 2: Zhong Y, Lee K, Deng Y, Ma Y, Chen Y, Li X, Wei C, Yang S, Wang T, Wong NJ, Muwonge AN, Azeloglu EU, Zhang W, Das B, He JC, Liu R. Arctigenin attenuates diabetic kidney disease through the activation of PP2A in podocytes. Nat Commun. 2019 Oct 4;10(1):4523. doi: 10.1038/s41467-019-12433-w. PMID: 31586053; PMCID: PMC6778111. 3: Shabgah AG, Suksatan W, Achmad MH, Bokov DO, Abdelbasset WK, Ezzatifar F, Hemmati S, Mohammadi H, Soleimani D, Jadidi-Niaragh F, Ahmadi M, Navashenaq JG. Arctigenin, an anti-tumor agent; a cutting-edge topic and up-to-the-minute approach in cancer treatment. Eur J Pharmacol. 2021 Oct 15;909:174419. doi: 10.1016/j.ejphar.2021.174419. Epub 2021 Aug 12. PMID: 34391770. 4: Qiao S, Lv C, Tao Y, Miao Y, Zhu Y, Zhang W, Sun D, Yun X, Xia Y, Wei Z, Dai Y. Arctigenin disrupts NLRP3 inflammasome assembly in colonic macrophages via downregulating fatty acid oxidation to prevent colitis-associated cancer. Cancer Lett. 2020 Oct 28;491:162-179. doi: 10.1016/j.canlet.2020.08.033. Epub 2020 Aug 27. PMID: 32861708. 5: Li H, Zhang X, Xiang C, Feng C, Fan C, Liu M, Lu H, Su H, Zhou Y, Qi Q, Xu Y, Tang W. Identification of phosphodiesterase-4 as the therapeutic target of arctigenin in alleviating psoriatic skin inflammation. J Adv Res. 2021 Mar 4;33:241-251. doi: 10.1016/j.jare.2021.02.006. PMID: 34603793; PMCID: PMC8463927. 6: Kang KR, Kim JS, Lim H, Seo JY, Park JH, Chun HS, Yu SK, Kim HJ, Kim CS, Kim DK. Arctigenin induces caspase-dependent apoptosis in FaDu human pharyngeal carcinoma cells. Korean J Physiol Pharmacol. 2022 Nov 1;26(6):447-456. doi: 10.4196/kjpp.2022.26.6.447. PMID: 36302620; PMCID: PMC9614403. 7: Gao Q, Yang M, Zuo Z. 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. doi: 10.1038/aps.2018.32. Epub 2018 Apr 26. PMID: 29698388; PMCID: PMC5943914. 8: Wu D, Jin L, Huang X, Deng H, Shen QK, Quan ZS, Zhang C, Guo HY. Arctigenin: pharmacology, total synthesis, and progress in structure modification. J Enzyme Inhib Med Chem. 2022 Dec;37(1):2452-2477. doi: 10.1080/14756366.2022.2115035. PMID: 36093586; PMCID: PMC9481144. 9: Liu X, Wang J, Dou P, Zhang X, Ran X, Liu L, Dou D. The Ameliorative Effects of Arctiin and Arctigenin on the Oxidative Injury of Lung Induced by Silica via TLR-4/NLRP3/TGF-β Signaling Pathway. Oxid Med Cell Longev. 2021 Jul 17;2021:5598980. doi: 10.1155/2021/5598980. PMID: 34336106; PMCID: PMC8313330. 10: He Y, Fan Q, Cai T, Huang W, Xie X, Wen Y, Shi Z. Molecular mechanisms of the action of Arctigenin in cancer. Biomed Pharmacother. 2018 Dec;108:403-407. doi: 10.1016/j.biopha.2018.08.158. Epub 2018 Sep 17. PMID: 30236849. 11: Li M, Jiang H, Wang Y, Xu Z, Xu H, Chen Y, Zhu J, Lin Z, Zhang M. Effect of arctigenin on neurological diseases: A review. J Ethnopharmacol. 2023 Oct 28;315:116642. doi: 10.1016/j.jep.2023.116642. Epub 2023 May 24. PMID: 37236381. 12: Guo S, Chen Y, Shi S, Wang X, Zhang H, Zhan Y, An H. Arctigenin, a novel TMEM16A inhibitor for lung adenocarcinoma therapy. Pharmacol Res. 2020 May;155:104721. doi: 10.1016/j.phrs.2020.104721. Epub 2020 Feb 22. PMID: 32097750. 13: Shi H, Zhao L, Guo X, Fang R, Zhang H, Dong G, Fu J, Yan F, Zhang J, Ning Z, Ma Q, Li Z, Li C, Dai J, Si C, Xiong H. Arctigenin Attenuates Breast Cancer Progression through Decreasing GM-CSF/TSLP/STAT3/β-Catenin Signaling. Int J Mol Sci. 2020 Sep 2;21(17):6357. doi: 10.3390/ijms21176357. Erratum in: Int J Mol Sci. 2020 Nov 23;21(22): PMID: 32887217; PMCID: PMC7503539. 14: Zhang X, Zou M, Liang Y, Yang Y, Jing L, Sun M, Dong Z, Zhang X, Xiong H, Dong G. Arctigenin inhibits abnormal germinal center reactions and attenuates murine lupus by inhibiting IFN-I pathway. Eur J Pharmacol. 2022 Mar 15;919:174808. doi: 10.1016/j.ejphar.2022.174808. Epub 2022 Feb 10. PMID: 35151645. 15: Zhao J, Chen Y, Dong L, Li X, Dong R, Zhou D, Wang C, Guo X, Zhang J, Xue Z, Xi Q, Zhang L, Yang G, Li Y, Zhang R. Arctigenin protects mice from thioglycollate-induced acute peritonitis. Pharmacol Res Perspect. 2020 Oct;8(5):e00660. doi: 10.1002/prp2.660. PMID: 32960513; PMCID: PMC7507838. 16: Li H, Yang C, Lan M, Liao X, Tang Z. Arctigenin promotes bone formation involving PI3K/Akt/PPARγ signaling pathway. Chem Biol Drug Des. 2020 Apr;95(4):451-459. doi: 10.1111/cbdd.13659. Epub 2020 Jan 14. PMID: 31883507. 17: Mottaghi S, Abbaszadeh H. A comprehensive mechanistic insight into the dietary and estrogenic lignans, arctigenin and sesamin as potential anticarcinogenic and anticancer agents. Current status, challenges, and future perspectives. Crit Rev Food Sci Nutr. 2022;62(26):7301-7318. doi: 10.1080/10408398.2021.1913568. Epub 2021 Apr 27. PMID: 33905270. 18: Liu C, Sun ZR, Wang MM, Yang ZZ, Zhang W, Ren Y, Han XQ, Liu R, Li Q, Nie SN. Arctigenin attenuates paraquat-induced human lung epithelial A549 cell injury by suppressing ROS/p38 mitogen-activated protein kinases-mediated apoptosis. World J Emerg Med. 2022;13(5):373-378. doi: 10.5847/wjem.j.1920-8642.2022.086. PMID: 36119774; PMCID: PMC9420658. 19: Tao Y, Qiao SM, Lv CJ, Yun XM, Yue MF, Fang YL, Wei ZF, Dai Y, Xia YF. Phytoestrogen arctigenin preserves the mucus barrier in inflammatory bowel diseases by inhibiting goblet cell apoptosis via the ERβ/TRIM21/PHB1 pathway. Phytother Res. 2022 Aug;36(8):3248-3264. doi: 10.1002/ptr.7495. Epub 2022 May 22. PMID: 35599350. 20: Avila-Carrasco L, Majano P, Sánchez-Toméro JA, Selgas R, López-Cabrera M, Aguilera A, González Mateo G. Natural Plants Compounds as Modulators of Epithelial-to-Mesenchymal Transition. Front Pharmacol. 2019 Jul 30;10:715. doi: 10.3389/fphar.2019.00715. PMID: 31417401; PMCID: PMC6682706.