Gossypin
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MedKoo CAT#: 464836

CAS#: 652-78-8

Description: Gossypin is a flavonoid glycoside originally isolated from H. vitifolius that has diverse biological activities. It inhibits RANKL-induced osteoclastogenesis in RAW 264.7 cells when used at a concentration of 5 µM. Gossypin inhibits Aurora B kinase (IC50 = 11.07 µM in a cell-free assay using the human enzyme), as well as Aurora A kinase and p90 ribosomal S6 kinase 2 (RSK2) at 20 µM. It induces cell cycle arrest at the G2/M phase and apoptosis in HGC-27 gastric cancer cells. Gossypin decreases lactate dehydrogenase (LDH) release induced by the glutathione-depleting agent D,L-buthionine (S,R)-sulfoximine in primary rat cortical cells (IC50 = 7.4 µg/ml). It reduces acetic acid-induced writhing in mice, an effect that can be reversed by the opioid antagonist naloxone, in a dose-dependent manner.

Chemical Structure

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Gossypin
CAS# 652-78-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464836
Name: Gossypin
CAS#: 652-78-8
Chemical Formula: C21H20O13
Exact Mass: 480.09
Molecular Weight: 480.378
Elemental Analysis: C, 52.51; H, 4.20; O, 43.30

Price and Availability

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50mg USD 350 2 Weeks
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Synonym: Gossypin; Gossypetin-8-O-glucoside;

IUPAC/Chemical Name: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key: SJRXVLUZMMDCNG-KKPQBLLMSA-N

InChi Code: InChI=1S/C21H20O13/c22-5-11-13(27)15(29)17(31)21(32-11)34-19-10(26)4-9(25)12-14(28)16(30)18(33-20(12)19)6-1-2-7(23)8(24)3-6/h1-4,11,13,15,17,21-27,29-31H,5H2/t11-,13-,15+,17-,21+/m1/s1

SMILES Code: O=C(C1=C(O)C=C2O)C(O)=C(OC1=C2O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C4=CC(O)=C(O)C=C4

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: 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

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Product Data:
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Biological target: Gossypin inhibits NF-κB and NF-κB-regulated gene expression. Gossypin inhibits RANKL-induced osteoclastogenesis both in mouse primary bone marrow cells and RAW 264.7 cells in vitro.
In vitro activity: Results showed that growth of gastric cancer cells was significantly inhibited by gossypin treatment in a dose dependent manner (Fig. 1B, C). Additionally, this study investigated the effect of gossypin on cell migration and data indicated that gossypin significantly suppressed migration (Fig. 1D). Reference: Phytother Res. 2019 Mar;33(3):640-650. https://pubmed.ncbi.nlm.nih.gov/30536456/
In vivo activity: ISO-induced I/R group rats exhibited the increased level of TNF-α, IL-1β, IL-6 in the serum and heart tissue. Gossypin significantly (P < 0.001) suppressed the level of inflammatory cytokines in the serum and heart tissue (Figure 10). Reference: J Inflamm Res. 2022 Mar 5;15:1637-1651. https://pubmed.ncbi.nlm.nih.gov/35282267/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 62.45
DMF:PBS (pH 7.2) (1:2) 0.3 0.62
DMSO 25.0 52.04

Preparing Stock Solutions

The following data is based on the product molecular weight 480.38 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
Formulation protocol: 1. Wang L, Wang X, Chen H, Zu X, Ma F, Liu K, Bode AM, Dong Z, Kim DJ. Gossypin inhibits gastric cancer growth by direct targeting of AURKA and RSK2. Phytother Res. 2019 Mar;33(3):640-650. doi: 10.1002/ptr.6253. Epub 2018 Dec 10. PMID: 30536456; PMCID: PMC6416069. 2. Kunnumakkara AB, Nair AS, Ahn KS, Pandey MK, Yi Z, Liu M, Aggarwal BB. Gossypin, a pentahydroxy glucosyl flavone, inhibits the transforming growth factor beta-activated kinase-1-mediated NF-kappaB activation pathway, leading to potentiation of apoptosis, suppression of invasion, and abrogation of osteoclastogenesis. Blood. 2007 Jun 15;109(12):5112-21. doi: 10.1182/blood-2007-01-067256. Epub 2007 Mar 1. Erratum in: Blood. 2013 Aug 15;122(7):1327-8. PMID: 17332240; PMCID: PMC1890830. 3. Cheng G, Zhang J, Jia S, Feng P, Chang F, Yan L, Gupta P, Wu H. Cardioprotective Effect of Gossypin Against Myocardial Ischemic/Reperfusion in Rats via Alteration of Oxidative Stress, Inflammation and Gut Microbiota. J Inflamm Res. 2022 Mar 5;15:1637-1651. doi: 10.2147/JIR.S348883. PMID: 35282267; PMCID: PMC8906873. 4. Mohamed M, El Sheikh AK, Mohammed HH. Modulation of Liver P-Glycoprotien Expression May Contribute to Gossypin Protection against Methotrexate-Induced Hepatotoxicity. Indian J Pharmacol. 2021 Jan-Feb;53(1):25-30. doi: 10.4103/ijp.IJP_824_19. PMID: 33975996; PMCID: PMC8216128.
In vitro protocol: 1. Wang L, Wang X, Chen H, Zu X, Ma F, Liu K, Bode AM, Dong Z, Kim DJ. Gossypin inhibits gastric cancer growth by direct targeting of AURKA and RSK2. Phytother Res. 2019 Mar;33(3):640-650. doi: 10.1002/ptr.6253. Epub 2018 Dec 10. PMID: 30536456; PMCID: PMC6416069. 2. Kunnumakkara AB, Nair AS, Ahn KS, Pandey MK, Yi Z, Liu M, Aggarwal BB. Gossypin, a pentahydroxy glucosyl flavone, inhibits the transforming growth factor beta-activated kinase-1-mediated NF-kappaB activation pathway, leading to potentiation of apoptosis, suppression of invasion, and abrogation of osteoclastogenesis. Blood. 2007 Jun 15;109(12):5112-21. doi: 10.1182/blood-2007-01-067256. Epub 2007 Mar 1. Erratum in: Blood. 2013 Aug 15;122(7):1327-8. PMID: 17332240; PMCID: PMC1890830.
In vivo protocol: 1. Cheng G, Zhang J, Jia S, Feng P, Chang F, Yan L, Gupta P, Wu H. Cardioprotective Effect of Gossypin Against Myocardial Ischemic/Reperfusion in Rats via Alteration of Oxidative Stress, Inflammation and Gut Microbiota. J Inflamm Res. 2022 Mar 5;15:1637-1651. doi: 10.2147/JIR.S348883. PMID: 35282267; PMCID: PMC8906873. 2. Mohamed M, El Sheikh AK, Mohammed HH. Modulation of Liver P-Glycoprotien Expression May Contribute to Gossypin Protection against Methotrexate-Induced Hepatotoxicity. Indian J Pharmacol. 2021 Jan-Feb;53(1):25-30. doi: 10.4103/ijp.IJP_824_19. PMID: 33975996; PMCID: PMC8216128.

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1: Mohamed M, El Sheikh AK, Mohammed HH. Modulation of Liver P-Glycoprotien Expression May Contribute to Gossypin Protection against Methotrexate-Induced Hepatotoxicity. Indian J Pharmacol. 2021 Jan-Feb;53(1):25-30. doi: 10.4103/ijp.IJP_824_19. PMID: 33975996.

2: Vidhya R, Anbumani VI, Dinakara Rao A, Anuradha CV. Identification of novel human neutrophil elastase inhibitors from dietary phytochemicals using in silico and in vitro studies. J Biomol Struct Dyn. 2020 Nov 23:1-11. doi: 10.1080/07391102.2020.1847685. Epub ahead of print. PMID: 33222615.

3: Bottoni M, Milani F, Colombo L, Nallio K, Colombo PS, Giuliani C, Bruschi P, Fico G. Using Medicinal Plants in Valmalenco (Italian Alps): From Tradition to Scientific Approaches. Molecules. 2020 Sep 10;25(18):4144. doi: 10.3390/molecules25184144. PMID: 32927742; PMCID: PMC7570945.

4: Cinar I. Apoptosis-Inducing Activity and Antiproliferative Effect of Gossypin on PC-3 Prostate Cancer Cells. Anticancer Agents Med Chem. 2021;21(4):445-450. doi: 10.2174/1871520620666200721103422. PMID: 32698736.

5: Khan MS, Gao J, Chen X, Zhang M, Yang F, Du Y, Moe TS, Munir I, Xue J, Zhang X. Isolation and Characterization of Plant Growth-Promoting Endophytic Bacteria Paenibacillus polymyxa SK1 from Lilium lancifolium. Biomed Res Int. 2020 Feb 27;2020:8650957. doi: 10.1155/2020/8650957. PMID: 32190683; PMCID: PMC7064867.

6: Ontiveros M, Rinaldi D, Marder M, Espelt MV, Mangialavori I, Vigil M, Rossi JP, Ferreira-Gomes M. Natural flavonoids inhibit the plasma membrane Ca2+-ATPase. Biochem Pharmacol. 2019 Aug;166:1-11. doi: 10.1016/j.bcp.2019.05.004. Epub 2019 May 6. PMID: 31071329.

7: Lakshminarayanashastry Viswanatha G, Venkatanarasappa Venkataranganna M, Lingeswara Prasad NB. Methanolic leaf extract of Punica granatum attenuates ischemia-reperfusion brain injury in Wistar rats: Potential antioxidant and anti-inflammatory mechanisms. Iran J Basic Med Sci. 2019 Feb;22(2):187-196. doi: 10.22038/ijbms.2018.30660.7389. PMID: 30834085; PMCID: PMC6396989.

8: Cinar I, Sirin B, Aydin P, Toktay E, Cadirci E, Halici I, Halici Z. Ameliorative effect of gossypin against acute lung injury in experimental sepsis model of rats. Life Sci. 2019 Mar 15;221:327-334. doi: 10.1016/j.lfs.2019.02.039. Epub 2019 Feb 20. PMID: 30797018.

9: Wang L, Wang X, Chen H, Zu X, Ma F, Liu K, Bode AM, Dong Z, Kim DJ. Gossypin inhibits gastric cancer growth by direct targeting of AURKA and RSK2. Phytother Res. 2019 Mar;33(3):640-650. doi: 10.1002/ptr.6253. Epub 2018 Dec 10. PMID: 30536456; PMCID: PMC6416069.

10: Sreeja PS, Arunachalam K, Martins DTO, Lima JCDS, Balogun SO, Pavan E, Saikumar S, Dhivya S, Kasipandi M, Parimelazhagan T. Sphenodesme involucrata var. paniculata (C.B. Clarke) Munir.: Chemical characterization, anti- nociceptive and anti-inflammatory activities of methanol extract of leaves. J Ethnopharmacol. 2018 Oct 28;225:71-80. doi: 10.1016/j.jep.2018.06.035. Epub 2018 Jun 28. PMID: 29960023.

11: Viswanatha GL, Venkataranganna MV, Prasad NBL, Hanumanthappa S. Chemical characterization and cerebroprotective effect of methanolic root extract of Colebrookea oppositifolia in rats. J Ethnopharmacol. 2018 Sep 15;223:63-75. doi: 10.1016/j.jep.2018.05.009. Epub 2018 May 16. Erratum in: J Ethnopharmacol. 2019 Jan 30;229:343. PMID: 29777902.

12: Rajagopal C, Lankadasari MB, Aranjani JM, Harikumar KB. Targeting oncogenic transcription factors by polyphenols: A novel approach for cancer therapy. Pharmacol Res. 2018 Apr;130:273-291. doi: 10.1016/j.phrs.2017.12.034. Epub 2018 Jan 4. PMID: 29305909.

13: Pradiba D, Aarthy M, Shunmugapriya V, Singh SK, Vasanthi M. Structural insights into the binding mode of flavonols with the active site of matrix metalloproteinase-9 through molecular docking and molecular dynamic simulations studies. J Biomol Struct Dyn. 2018 Nov;36(14):3718-3739. doi: 10.1080/07391102.2017.1397058. Epub 2017 Nov 6. PMID: 29068268.

14: Katary M, Salahuddin A. Ameliorative effect of gossypin against gentamicin- induced nephrotoxicity in rats. Life Sci. 2017 May 1;176:75-81. doi: 10.1016/j.lfs.2017.03.009. Epub 2017 Mar 14. PMID: 28302561.

15: Sjöstedt N, Holvikari K, Tammela P, Kidron H. Inhibition of Breast Cancer Resistance Protein and Multidrug Resistance Associated Protein 2 by Natural Compounds and Their Derivatives. Mol Pharm. 2017 Jan 3;14(1):135-146. doi: 10.1021/acs.molpharmaceut.6b00754. Epub 2016 Nov 28. PMID: 28043125.

16: Urarte E, Asensio AC, Tellechea E, Pires L, Moran JF. Evaluation of the anti-nitrative effect of plant antioxidants using a cowpea Fe-superoxide dismutase as a target. Plant Physiol Biochem. 2014 Oct;83:356-64. doi: 10.1016/j.plaphy.2014.08.019. Epub 2014 Sep 2. PMID: 25221924.

17: Chandrashekhar VM, Ganapaty S, Ramkishan A, Narsu ML. Neuroprotective activity of gossypin from Hibiscus vitifolius against global cerebral ischemia model in rats. Indian J Pharmacol. 2013 Nov-Dec;45(6):575-80. doi: 10.4103/0253-7613.121367. PMID: 24347764; PMCID: PMC3847246.

18: Ramasamy D, Saraswathy A. Isolation of methyl 27-caffeoyloxyoleanolate--a new oleanane Triterpenoid from the roots of Hibiscus vitifolius. Nat Prod Commun. 2013 Apr;8(4):433-4. PMID: 23738444.

19: Bhaskaran S, Dileep KV, Deepa SS, Sadasivan C, Klausner M, Krishnegowda NK, Tekmal RR, VandeBerg JL, Nair HB. Gossypin as a novel selective dual inhibitor of V-RAF murine sarcoma viral oncogene homolog B1 and cyclin-dependent kinase 4 for melanoma. Mol Cancer Ther. 2013 Apr;12(4):361-72. doi: 10.1158/1535-7163.MCT-12-0965. Epub 2013 Mar 29. PMID: 23543365.

20: Shi L, Chen J, Wang YY, Sun G, Liu JN, Zhang JX, Yan W, Qian CF, Liu N, Fu Z, You YP, Zeng Y. Gossypin induces G2/M arrest in human malignant glioma U251 cells by the activation of Chk1/Cdc25C pathway. Cell Mol Neurobiol. 2012 Mar;32(2):289-96. doi: 10.1007/s10571-011-9760-8. Epub 2011 Oct 9. PMID: 21984341.