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MedKoo Cat#: 562382 | Name: Gossypetin
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Description:

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

Gossypetin is a flavonoid that has been found in H. sabdariffa and has diverse biological activities. It inhibits the MAP2K kinases MKK3 and MKK6 in a concentration-dependent manner, as well as induces apoptosis and cell cycle arrest at the G2 phase in KYSE-450 and KYSE-510 esophageal cancer cells when used at a concentration of 20 µM. Gossypetin scavenges DPPH radicals and inhibits copper-induced lipid peroxidation in cell-free assays. It reduces high-fat diet-induced increases in serum cholesterol, triglycerides, and LDL-cholesterol levels, as well as decreases aortic extracellular lipid and foam cell deposits in a rabbit model of atherosclerosis when administered at a dose of 10 mg/kg.

Chemical Structure

Gossypetin
Gossypetin
CAS#489-35-0

Theoretical Analysis

MedKoo Cat#: 562382

Name: Gossypetin

CAS#: 489-35-0

Chemical Formula: C15H10O8

Exact Mass: 318.0376

Molecular Weight: 318.24

Elemental Analysis: C, 56.61; H, 3.17; O, 40.22

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
25mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Gossypetin; Articulatidin; Equisporol; C.I. 75750; 8-hydroxy Quercetin; 8 hydroxy Quercetin; 8-hydroxyquercetin; 8-hydroxy-quercetin
IUPAC/Chemical Name
2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxychromen-4-one
InChi Key
YRRAGUMVDQQZIY-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)14-13(22)12(21)10-8(18)4-9(19)11(20)15(10)23-14/h1-4,16-20,22H
SMILES Code
O=C1C(O)=C(C2=CC=C(O)C(O)=C2)OC3=C1C(O)=CC(O)=C3O
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
>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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Gossypetin is a hexahydroxylated flavonoid and is a potent mitogen-activated protein kinase kinase (MKK)3 and MKK6 inhibitor with strongly attenuates the MKK3/6-p38 signaling pathway, has various pharmacological activities, including antioxidant, antibacterial and anticancer activities.
In vitro activity:
To verify if GTIN (gossypetin) induced the up-regulation of cdk inhibitors, contributing to inhibit cyclin/cdks activities, A7r5 cells were treated with GTIN at the indicated doses. As shown in Figure 2c, there was a significant reduction in expression of cyclin E/cdk-2 complex in the GTIN treatments, while no change in cyclin D1/cdk-4 complex. These results concluded that cyclin E/cdk-2 and Rb/E2F1 complexes participated in the GTIN-induced VSMCs cell-cycle arrest at G0/G1 stage. Reference: Antioxidants (Basel). 2021 Aug 26;10(9):1357. https://pubmed.ncbi.nlm.nih.gov/34572989/
In vivo activity:
Gossypetin caused G2 phase cell cycle arrest and induced intrinsic apoptosis by activating caspases 3 and 7 and increasing the expression of BAX and cytochrome c. Notably, gossypetin suppressed patient-derived esophageal xenograft tumor growth in an in vivo mouse model. Reference: Cancer Lett. 2019 Feb 1;442:126-136. https://pubmed.ncbi.nlm.nih.gov/30391783/

Preparing Stock Solutions

The following data is based on the product molecular weight 318.24 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
Formulation protocol:
1. Lin HH, Hsieh MC, Wang CP, Yu PR, Lee MS, Chen JH. Anti-Atherosclerotic Effect of Gossypetin on Abnormal Vascular Smooth Muscle Cell Proliferation and Migration. Antioxidants (Basel). 2021 Aug 26;10(9):1357. doi: 10.3390/antiox10091357. PMID: 34572989; PMCID: PMC8470489. 2. Gu K, Wang T, Peng L, Zhao Y. FIP-fve Stimulates Cell Proliferation and Enhances IL-2 Release by Activating MAP2K3/p38α (MAPK14) Signaling Pathway in Jurkat E6-1 Cells. Front Nutr. 2022 May 9;9:881924. doi: 10.3389/fnut.2022.881924. PMID: 35614983; PMCID: PMC9125247. 3. Xie X, Liu K, Liu F, Chen H, Wang X, Zu X, Ma X, Wang T, Wu Q, Zheng Y, Bode AM, Dong Z, Kim DJ. Gossypetin is a novel MKK3 and MKK6 inhibitor that suppresses esophageal cancer growth in vitro and in vivo. Cancer Lett. 2019 Feb 1;442:126-136. doi: 10.1016/j.canlet.2018.10.016. Epub 2018 Nov 2. PMID: 30391783.
In vitro protocol:
1. Lin HH, Hsieh MC, Wang CP, Yu PR, Lee MS, Chen JH. Anti-Atherosclerotic Effect of Gossypetin on Abnormal Vascular Smooth Muscle Cell Proliferation and Migration. Antioxidants (Basel). 2021 Aug 26;10(9):1357. doi: 10.3390/antiox10091357. PMID: 34572989; PMCID: PMC8470489. 2. Gu K, Wang T, Peng L, Zhao Y. FIP-fve Stimulates Cell Proliferation and Enhances IL-2 Release by Activating MAP2K3/p38α (MAPK14) Signaling Pathway in Jurkat E6-1 Cells. Front Nutr. 2022 May 9;9:881924. doi: 10.3389/fnut.2022.881924. PMID: 35614983; PMCID: PMC9125247.
In vivo protocol:
1. Xie X, Liu K, Liu F, Chen H, Wang X, Zu X, Ma X, Wang T, Wu Q, Zheng Y, Bode AM, Dong Z, Kim DJ. Gossypetin is a novel MKK3 and MKK6 inhibitor that suppresses esophageal cancer growth in vitro and in vivo. Cancer Lett. 2019 Feb 1;442:126-136. doi: 10.1016/j.canlet.2018.10.016. Epub 2018 Nov 2. PMID: 30391783.
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Development of Validated High-performance Thin-layer Chromatography Method for Simultaneous Determination of Quercetin and Kaempferol in Thespesia populnea. Pharmacognosy Res. 2017 Jul-Sep;9(3):277-281. doi: 10.4103/0974-8490.210326. PubMed PMID: 28827970; PubMed Central PMCID: PMC5541485. 5: Lee MS, Tsai CW, Wang CP, Chen JH, Lin HH. Anti-prostate cancer potential of gossypetin via inducing apoptotic and autophagic cell death. Mol Carcinog. 2017 Dec;56(12):2578-2592. doi: 10.1002/mc.22702. Epub 2017 Aug 3. PubMed PMID: 28671312. 6: Cai HD, Su SL, Qian DW, Guo S, Tao WW, Cong XD, Tang R, Duan JA. Renal protective effect and action mechanism of Huangkui capsule and its main five flavonoids. J Ethnopharmacol. 2017 Jul 12;206:152-159. doi: 10.1016/j.jep.2017.02.046. Epub 2017 Apr 10. PubMed PMID: 28408246. 7: Du LY, Tao JH, Jiang S, Qian DW, Guo JM, Duan JA. Metabolic profiles of the Flos Abelmoschus manihot extract by intestinal bacteria from the normal and CKD model rats based on UPLC-Q-TOF/MS. Biomed Chromatogr. 2017 Feb;31(2). doi: 10.1002/bmc.3795. Epub 2016 Aug 12. PubMed PMID: 27451133. 8: Dudek B, Warskulat AC, Schneider B. The Occurrence of Flavonoids and Related Compounds in Flower Sections of Papaver nudicaule. Plants (Basel). 2016 Jun 22;5(2). pii: E28. doi: 10.3390/plants5020028. PubMed PMID: 27338493; PubMed Central PMCID: PMC4931408. 9: Raj U, Varadwaj PK. Flavonoids as Multi-target Inhibitors for Proteins Associated with Ebola Virus: In Silico Discovery Using Virtual Screening and Molecular Docking Studies. Interdiscip Sci. 2016 Jun;8(2):132-41. doi: 10.1007/s12539-015-0109-8. Epub 2015 Aug 19. Erratum in: Interdiscip Sci. 2016 Jun;8(2):142. PubMed PMID: 26286008. 10: Clark BR, Pramanick S, Arancon N, Borris RP. Unusual Flavonoid Glycosides from the Hawaiian Tree Metrosideros polymorpha. Nat Prod Commun. 2015 Jun;10(6):925-8. PubMed PMID: 26197518. 11: Khan A, Manna K, Das DK, Kesh SB, Sinha M, Das U, Biswas S, Sengupta A, Sikder K, Datta S, Ghosh M, Chakrabarty A, Banerji A, Dey S. Gossypetin ameliorates ionizing radiation-induced oxidative stress in mice liver--a molecular approach. Free Radic Res. 2015 Oct;49(10):1173-86. doi: 10.3109/10715762.2015.1053878. Epub 2015 Aug 14. PubMed PMID: 25994373. 12: Shimokawa S, Iwashina T, Murakami N. Flower color changes in three Japanese hibiscus species: further quantitative variation of anthocyanin and flavonols. Nat Prod Commun. 2015 Mar;10(3):451-2. PubMed PMID: 25924527. 13: Gadotti VM, Caballero AG, Berger ND, Gladding CM, Chen L, Pfeifer TA, Zamponi GW. Small organic molecule disruptors of Cav3.2 - USP5 interactions reverse inflammatory and neuropathic pain. Mol Pain. 2015 Mar 14;11:12. doi: 10.1186/s12990-015-0011-8. PubMed PMID: 25889575; PubMed Central PMCID: PMC4364099. 14: Wang X, Wang Z, Sidhu PS, Desai UR, Zhou Q. 6-Hydroxyflavone and derivatives exhibit potent anti-inflammatory activity among mono-, di- and polyhydroxylated flavones in kidney mesangial cells. PLoS One. 2015 Mar 19;10(3):e0116409. doi: 10.1371/journal.pone.0116409. eCollection 2015. PubMed PMID: 25790236; PubMed Central PMCID: PMC4366162. 15: Gadotti VM, Caballero AG, Berger ND, Gladding CM, Chen L, Pfeifer TA, Zamponi GW. Small organic molecule disruptors of Cav3.2 - USP5 interactions reverse inflammatory and neuropathic pain. Mol Pain. 2015 Dec;11(1):11. doi: 10.1186/s12990-015-0011-8. Epub 2015 Mar 14. PubMed PMID: 25775966. 16: Liang JY, Du XY, Chen Y, Ma XM, Xie R, Zhang J. [Chemical constituents from leaf of Rhododendron przewalskii]. Zhong Yao Cai. 2014 Aug;37(8):1381-2. Chinese. PubMed PMID: 25726644. 17: Raj U, Varadwaj PK. Flavonoids as multi-target inhibitors for proteins associated with Ebola virus: in-silico discovery using virtual screening and molecular docking studies. Interdiscip Sci. 2015 Feb 6. [Epub ahead of print] PubMed PMID: 25663119. 18: Lin HH. In Vitro and in Vivo Atheroprotective Effects of Gossypetin against Endothelial Cell Injury by Induction of Autophagy. Chem Res Toxicol. 2015 Feb 16;28(2):202-15. PubMed PMID: 25622137. 19: Zhang H, Li N, Li K, Li P. Protective effect of Urtica dioica methanol extract against experimentally induced urinary calculi in rats. Mol Med Rep. 2014 Dec;10(6):3157-62. doi: 10.3892/mmr.2014.2610. Epub 2014 Oct 8. PubMed PMID: 25310585. 20: Amrutha K, Nanjan P, Shaji SK, Sunilkumar D, Subhalakshmi K, Rajakrishna L, Banerji A. Discovery of lesser known flavones as inhibitors of NF-κB signaling in MDA-MB-231 breast cancer cells--A SAR study. Bioorg Med Chem Lett. 2014 Oct 1;24(19):4735-4742. doi: 10.1016/j.bmcl.2014.07.093. Epub 2014 Aug 14. 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