Avicularin | CAS#572-30-5 | Inhibitor

MedKoo Cat#: 112075 | Name: Avicularin

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Description:

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

Avicularin is a flavonoid glycoside that inhibits fatty acid synthase (FASN) and aldose reductase and inhibits the proliferation, migration, and invasion of, as well as induces apoptosis and cell cycle arrest at the G0/G1 phase in, Huh7 hepatocellular carcinoma cells.

Chemical Structure

Avicularin

CAS#572-30-5

Theoretical Analysis

MedKoo Cat#: 112075

Name: Avicularin

CAS#: 572-30-5

Chemical Formula: C20H18O11

Exact Mass: 434.0849

Molecular Weight: 434.35

Elemental Analysis: C, 55.31; H, 4.18; O, 40.52

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks
25mg	USD 1,150.00	2 Weeks

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Related CAS #

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Synonym

Avicularin; Quercetin 3-O-α-L-arabinofuranoside

IUPAC/Chemical Name

3-(((2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

InChi Key

BDCDNTVZSILEOY-UXYNSRGZSA-N

InChi Code

InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1

SMILES Code

O=C1C(O[C@@H]2O[C@H]([C@@H]([C@H]2O)O)CO)=C(OC3=CC(O)=CC(O)=C13)C4=CC(O)=C(O)C=C4

Appearance

Solid powder

Purity

>98% (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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

	Solvent	mg/mL	mM
Solubility
	DMF	50.0	115.11
	DMSO	30.0	69.07
	Ethanol	5.0	11.51

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 434.35 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: Zou ZL, Sun MH, Yin WF, Yang L, Kong LY. Avicularin suppresses cartilage extracellular matrix degradation and inflammation via TRAF6/MAPK activation. Phytomedicine. 2021 Oct;91:153657. doi: 10.1016/j.phymed.2021.153657. Epub 2021 Jul 12. PMID: 34371251. 2: Samant NP, Gupta GL. Avicularin Attenuates Memory Impairment in Rats with Amyloid Beta-Induced Alzheimer's Disease. Neurotox Res. 2022 Feb;40(1):140-153. doi: 10.1007/s12640-021-00467-2. Epub 2022 Jan 18. PMID: 35043380. 3: Amadi JA, Amadi PU, Njoku UC, Onitchi CL. Lettuce-avicularin treatment reverses insulin resistance through stimulation of glycolytic kinases and insulin signaling molecules. Iran J Basic Med Sci. 2021 Feb;24(2):232-239. doi: 10.22038/ijbms.2020.49770.11368. PMID: 33953863; PMCID: PMC8061317. 4: Wang Z, Li F, Quan Y, Shen J. Avicularin ameliorates human hepatocellular carcinoma via the regulation of NF‑κB/COX‑2/PPAR‑γ activities. Mol Med Rep. 2019 Jun;19(6):5417-5423. doi: 10.3892/mmr.2019.10198. Epub 2019 Apr 25. PMID: 31059053; PMCID: PMC6522888. 5: Zhang Z, Lv G, Du L. Avicularin Reduces the Expression of Mediators of Inflammation and Oxidative Stress in Bradykinin-Treated MG-63 Human Osteoblastic Osteosarcoma Cells. Med Sci Monit. 2020 May 28;26:e921957. doi: 10.12659/MSM.921957. PMID: 32463805; PMCID: PMC7278328. 6: Qiu T, Shi JX, Cheng C, Jiang H, Ruan HN, Li J, Liu CM. Avicularin Attenuates Lead-Induced Impairment of Hepatic Glucose Metabolism by Inhibiting the ER Stress-Mediated Inflammatory Pathway. Nutrients. 2022 Nov 13;14(22):4806. doi: 10.3390/nu14224806. PMID: 36432494; PMCID: PMC9697143. 7: Vo VA, Lee JW, Chang JE, Kim JY, Kim NH, Lee HJ, Kim SS, Chun W, Kwon YS. Avicularin Inhibits Lipopolysaccharide-Induced Inflammatory Response by Suppressing ERK Phosphorylation in RAW 264.7 Macrophages. Biomol Ther (Seoul). 2012 Nov;20(6):532-7. doi: 10.4062/biomolther.2012.20.6.532. PMID: 24009846; PMCID: PMC3762284. 8: Fujimori K, Shibano M. Avicularin, a plant flavonoid, suppresses lipid accumulation through repression of C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells. J Agric Food Chem. 2013 May 29;61(21):5139-47. doi: 10.1021/jf401154c. Epub 2013 May 16. PMID: 23647459. 9: Wang Y, Liu M, Chen S, Wu Q. Avicularin inhibits cell proliferation and induces cell apoptosis in cutaneous squamous cell carcinoma. Exp Ther Med. 2020 Feb;19(2):1065-1071. doi: 10.3892/etm.2019.8303. Epub 2019 Dec 9. PMID: 32010270; PMCID: PMC6966122. 10: Wang W, Zheng H, Zheng M, Liu X, Yu J. Protective effect of avicularin on rheumatoid arthritis and its associated mechanisms. Exp Ther Med. 2018 Dec;16(6):5343-5349. doi: 10.3892/etm.2018.6872. Epub 2018 Oct 17. PMID: 30542493; PMCID: PMC6257287. 11: Buqui GA, Gouvea DR, Sy SK, Voelkner A, Singh RS, da Silva DB, Kimura E, Derendorf H, Lopes NP, Diniz A. Pharmacokinetic evaluation of avicularin using a model-based development approach. Planta Med. 2015 Mar;81(5):373-81. doi: 10.1055/s-0035-1545728. Epub 2015 Mar 17. PMID: 25782034. 12: Zhuang Q, Chen S, Zhang W, Gu M, Xiao L, Li Y, Yang Y, Feng C, Li H, Geng D, Wang Z. Avicularin Alleviates Osteoporosis in Ovariectomized Mice by Inhibiting Osteoclastogenesis through NF-κB Pathway Inhibition. J Agric Food Chem. 2023 Jan 11;71(1):411-420. doi: 10.1021/acs.jafc.2c05954. Epub 2022 Dec 20. PMID: 36540936; PMCID: PMC9838558. 13: Shen Z, Xu Y, Jiang X, Wang Z, Guo Y, Pan W, Hou J. Avicularin Relieves Depressive-Like Behaviors Induced by Chronic Unpredictable Mild Stress in Mice. Med Sci Monit. 2019 Apr 15;25:2777-2784. doi: 10.12659/MSM.912401. PMID: 30986204; PMCID: PMC6482862. 14: Guo XF, Liu JP, Ma SQ, Zhang P, Sun WD. Avicularin reversed multidrug- resistance in human gastric cancer through enhancing Bax and BOK expressions. Biomed Pharmacother. 2018 Jul;103:67-74. doi: 10.1016/j.biopha.2018.03.110. Epub 2018 Apr 7. PMID: 29635130. 15: Hossain U, Das AK, Ghosh S, Sil PC. An overview on the role of bioactive α-glucosidase inhibitors in ameliorating diabetic complications. Food Chem Toxicol. 2020 Nov;145:111738. doi: 10.1016/j.fct.2020.111738. Epub 2020 Sep 9. PMID: 32916220; PMCID: PMC7480666. 16: Yang Y, Sheng D, Shi J, Xiao L, Wang Z, Yin Z, Zhuang Q, Chen S, Li Y, Gu Y, Zhu J, Geng D, Wang Z. Avicularin alleviates osteoporosis-induced implant loosening by attenuating macrophage M1 polarization via its inhibitory effect on the activation of NF-κB. Biomed Pharmacother. 2023 Feb;158:114113. doi: 10.1016/j.biopha.2022.114113. Epub 2022 Dec 12. PMID: 36516692. 17: Kumar M, Tomar M, Amarowicz R, Saurabh V, Nair MS, Maheshwari C, Sasi M, Prajapati U, Hasan M, Singh S, Changan S, Prajapat RK, Berwal MK, Satankar V. Guava (Psidium guajava L.) Leaves: Nutritional Composition, Phytochemical Profile, and Health-Promoting Bioactivities. Foods. 2021 Apr 1;10(4):752. doi: 10.3390/foods10040752. PMID: 33916183; PMCID: PMC8066327. 18: Zhang WM, Li RF, Sun M, Hu DM, Qiu JF, Yan YH. UPLC-MS/MS method for determination of avicularin in rat plasma and its application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Aug 15;965:107-11. doi: 10.1016/j.jchromb.2014.06.015. Epub 2014 Jun 20. PMID: 25010713. 19: Morita T, Akiyoshi T, Tsuchitani T, Kataoka H, Araki N, Yajima K, Katayama K, Imaoka A, Ohtani H. Inhibitory Effects of Cranberry Juice and Its Components on Intestinal OATP1A2 and OATP2B1: Identification of Avicularin as a Novel Inhibitor. J Agric Food Chem. 2022 Mar 16;70(10):3310-3320. doi: 10.1021/acs.jafc.2c00065. Epub 2022 Mar 1. PMID: 35230114. 20: Zhu X, Qiu Z, Ouyang W, Miao J, Xiong P, Mao D, Feng K, Li M, Luo M, Xiao H, Cao Y. Hepatic transcriptome and proteome analyses provide new insights into the regulator mechanism of dietary avicularin in diabetic mice. Food Res Int. 2019 Nov;125:108570. doi: 10.1016/j.foodres.2019.108570. Epub 2019 Jul 19. PMID: 31554135.