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MedKoo Cat#: 573209 | Name: Apigetrin
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Description:

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

Apigetrin is a flavanoid derivved from dandelions which may inhibit neuroinflammation in BV-2 microglia and have a neuroprotective effect in HT22 hippocampal cells. This molecule may also hinder cancer progression by inhibiting various pathways such as STAT3/JAK2.

Chemical Structure

Apigetrin
Apigetrin
CAS#578-74-5

Theoretical Analysis

MedKoo Cat#: 573209

Name: Apigetrin

CAS#: 578-74-5

Chemical Formula: C21H20O10

Exact Mass: 432.1056

Molecular Weight: 432.38

Elemental Analysis: C, 58.34; H, 4.66; O, 37.00

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
25mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Apigetrin; Cosmosiin; Apigenin 7-glucoside; 4′,5,7-Trihydroxyflavone 7-glucoside
IUPAC/Chemical Name
7-(beta-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
InChi Key
KMOUJOKENFFTPU-MKJMBMEGSA-N
InChi Code
InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21?/m1/s1
SMILES Code
O=C1C=C(C2=CC=C(O)C=C2)OC3=C1C(O)=CC(OC4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)=C3
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
Soluble in DMSO
Shelf Life
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 432.38 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.

Recalculate based on batch purity %
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: Bhosale PB, Abusaliya A, Kim HH, Ha SE, Park MY, Jeong SH, Vetrivel P, Heo JD, Kim JA, Won CK, Kim HW, Kim GS. Apigetrin Promotes TNFα-Induced Apoptosis, Necroptosis, G2/M Phase Cell Cycle Arrest, and ROS Generation through Inhibition of NF-κB Pathway in Hep3B Liver Cancer Cells. Cells. 2022 Sep 1;11(17):2734. doi: 10.3390/cells11172734. PMID: 36078142; PMCID: PMC9454891. 2: Ha SE, Bhagwan Bhosale P, Kim HH, Park MY, Abusaliya A, Kim GS, Kim JA. Apigetrin Abrogates Lipopolysaccharide-Induced Inflammation in L6 Skeletal Muscle Cells through NF-κB/MAPK Signaling Pathways. Curr Issues Mol Biol. 2022 Jun 8;44(6):2635-2645. doi: 10.3390/cimb44060180. PMID: 35735621; PMCID: PMC9221909. 3: Zhang R, Shi J, Wang T, Qiu X, Liu R, Li Y, Gao Q, Wang N. Apigetrin ameliorates streptozotocin-induced pancreatic β-cell damages via attenuating endoplasmic reticulum stress. In Vitro Cell Dev Biol Anim. 2020 Sep;56(8):622-634. doi: 10.1007/s11626-020-00478-x. Epub 2020 Sep 8. PMID: 32901429. 4: Kim SM, Vetrivel P, Ha SE, Kim HH, Kim JA, Kim GS. Apigetrin induces extrinsic apoptosis, autophagy and G2/M phase cell cycle arrest through PI3K/AKT/mTOR pathway in AGS human gastric cancer cell. J Nutr Biochem. 2020 Sep;83:108427. doi: 10.1016/j.jnutbio.2020.108427. Epub 2020 May 21. PMID: 32559585. 5: Hadrich F, Sayadi S. Apigetrin inhibits adipogenesis in 3T3-L1 cells by downregulating PPARγ and CEBP-α. Lipids Health Dis. 2018 Apr 25;17(1):95. doi: 10.1186/s12944-018-0738-0. PMID: 29695233; PMCID: PMC5922308. 6: Lim HS, Kim OS, Kim BY, Jeong SJ. Apigetrin from Scutellaria baicalensis Georgi Inhibits Neuroinflammation in BV-2 Microglia and Exerts Neuroprotective Effect in HT22 Hippocampal Cells. J Med Food. 2016 Nov;19(11):1032-1040. doi: 10.1089/jmf.2016.0074. PMID: 27845861. 7: Lee YK, Kim JE, Xu Y, Han H, Lee JH, Lee HJ. AKT, a Key Transmitter of HIF-1α and AR Signaling Pathways, Has a Critical Role in the Apigetrin-Mediated Anti- Cancer Effects in Prostate Cancer Cells. Biomedicines. 2022 Jun 9;10(6):1370. doi: 10.3390/biomedicines10061370. PMID: 35740392; PMCID: PMC9220772. 8: Guo H, Li M, Xu LJ. Apigetrin treatment attenuates LPS-induced acute otitis media though suppressing inflammation and oxidative stress. Biomed Pharmacother. 2019 Jan;109:1978-1987. doi: 10.1016/j.biopha.2018.07.022. Epub 2018 Nov 26. PMID: 30551453. 9: Tsolmon S, Nakazaki E, Han J, Isoda H. Apigetrin induces erythroid differentiation of human leukemia cells K562: proteomics approach. Mol Nutr Food Res. 2011 May;55 Suppl 1:S93-S102. doi: 10.1002/mnfr.201000650. Epub 2011 Apr 11. PMID: 21480518. 10: Abdulrasheed-Adeleke T, Lawal B, Agwupuye EI, Kuo Y, Eni AM, Ekoh OF, Lukman HY, Onikanni AS, Olawale F, Saidu S, Ibrahim YO, Al Ghamdi MAS, Aggad SS, Alsayegh AA, Aljarba NH, Batiha GE, Wu ATH, Huang HS. Apigetrin-enriched Pulmeria alba extract prevents assault of STZ on pancreatic β-cells and neuronal oxidative stress with concomitant attenuation of tissue damage and suppression of inflammation in the brain of diabetic rats. Biomed Pharmacother. 2023 Jun;162:114582. doi: 10.1016/j.biopha.2023.114582. Epub 2023 Mar 28. PMID: 36989727. 11: Lin XH, Pan JB, Zhang XJ. WITHDRAWN: Anti-inflammatory and anti-oxidant effects of apigetrin on LPS-induced acute lung injury by regulating Nrf2 and AMPK pathways. Biochem Biophys Res Commun. 2017 Jul 13:S0006-291X(17)31413-4. doi: 10.1016/j.bbrc.2017.07.071. Epub ahead of print. PMID: 28712867. 12: Sun Q, Lu NN, Feng L. Apigetrin inhibits gastric cancer progression through inducing apoptosis and regulating ROS-modulated STAT3/JAK2 pathway. Biochem Biophys Res Commun. 2018 Mar 25;498(1):164-170. doi: 10.1016/j.bbrc.2018.02.009. Epub 2018 Mar 5. PMID: 29408335. 13: Thuan NH, Chaudhary AK, Van Cuong D, Cuong NX. Engineering co-culture system for production of apigetrin in Escherichia coli. J Ind Microbiol Biotechnol. 2018 Mar;45(3):175-185. doi: 10.1007/s10295-018-2012-x. Epub 2018 Jan 24. PMID: 29362971. 14: Ivanov M, Kannan A, Stojković DS, Glamočlija J, Calhelha RC, Ferreira ICFR, Sanglard D, Soković M. Flavones, Flavonols, and Glycosylated Derivatives-Impact on Candida albicans Growth and Virulence, Expression of CDR1 and ERG11, Cytotoxicity. Pharmaceuticals (Basel). 2020 Dec 30;14(1):27. doi: 10.3390/ph14010027. PMID: 33396973; PMCID: PMC7824033. 15: Hazra S, Ray AS, Rahaman CH. Natural Phytocompounds from Common Indian Spices for Identification of Three Potential Inhibitors of Breast Cancer: A Molecular Modelling Approach. Molecules. 2022 Oct 5;27(19):6590. doi: 10.3390/molecules27196590. PMID: 36235128; PMCID: PMC9573590. 16: Isoda H, Motojima H, Onaga S, Samet I, Villareal MO, Han J. Analysis of the erythroid differentiation effect of flavonoid apigenin on K562 human chronic leukemia cells. Chem Biol Interact. 2014 Sep 5;220:269-77. doi: 10.1016/j.cbi.2014.07.006. Epub 2014 Jul 21. PMID: 25058688. 17: Che DN, Cho BO, Shin JY, Kang HJ, Kim JS, Choi J, Jang SI. Anti-atopic dermatitis effects of hydrolyzed celery extract in mice. J Food Biochem. 2020 Jun;44(6):e13198. doi: 10.1111/jfbc.13198. Epub 2020 Mar 23. PMID: 32202321. 18: Umran NSS, Mohamed S, Lau SF, Mohd Ishak NI. Citrus hystrix leaf extract attenuated diabetic-cataract in STZ-rats. J Food Biochem. 2020 Aug;44(8):e13258. doi: 10.1111/jfbc.13258. Epub 2020 Jun 15. PMID: 32539198. 19: Luo C, Wang A, Wang X, Li J, Liu H, Wang M, Wang L, Lai D, Zhou L. A new proline-containing flavonol glycoside from Caragana leucophloea Pojark. Nat Prod Res. 2015;29(19):1811-9. doi: 10.1080/14786419.2015.1007974. Epub 2015 Feb 12. PMID: 25675255. 20: Stepanova AY, Solov'eva AI, Malunova MV, Salamaikina SA, Panov YM, Lelishentsev AA. Hairy Roots of Scutellaria spp. (Lamiaceae) as Promising Producers of Antiviral Flavones. Molecules. 2021 Jun 27;26(13):3927. doi: 10.3390/molecules26133927. PMID: 34199058; PMCID: PMC8271535.