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G1036 Sigma

Gossypin

≥90% (TLC), from Hibiscus vitifolius

Synonym: 2-(3,4-Dihydroxyphenyl)-8-(β-D-glucopyranosyloxy)-3,5,7-trihydroxy- 4H-1-benzopyran-4-one, 3,3′,4′,5,7,8-Hexahydroxyflavone 8-glucoside, Gossypetin 8-glucoside

  • CAS Number 652-78-8

  • Empirical Formula (Hill Notation) C21H20O13

  • Molecular Weight 480.38

  •  MDL number MFCD00017429

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Properties

biological source   from Hibiscus vitifolius
assay   ≥90% (TLC)

Description

Biochem/physiol Actions

Gossypin is an anti-inflammatory pentahydroxyflavone glucoside isolated from Hibiscus vitifolius that is used as an herbal remedy for diabetes, jaundice, and inflammation. Gossypin potently inhibits human cancer cell proliferation, including melanoma and glioma cells. Gossypin directly binds and inhibits BRAFV600E and CDK4 kinases, and also regulates Chk1 and Cdc25C in U251 glioma cells.

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Gossypin
SML0761Gossypin

≥90% (HPLC)

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
WGK Germany 
3
RTECS 
DJ3009900

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.1 During the oxi...
BioFiles 2007, 2.2, 2.
Keywords: Adhesion, Anti-inflammatory agents, Applications, Cancer, Cardiovascular, Catalysis, Diabetes, Diseases, Gene expression, Metabolism, Neurodegenerative Diseases, Peroxidations, Phosphorylations, Prebiotics, Probiotics, Reductions, Transcription, Transduction, Vitamins

Peer-Reviewed Papers

References

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Neuroprotective activity of gossypin from Hibiscus vitifolius against global cerebral ischemia model in rats. Chandrashekhar VM, Ganapaty S, Ramkishan A, et al. Indian J. Pharmacol. 45(6), 575-80, (2013)

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Gossypin as a Novel Selective Dual Inhibitor of v-raf Murine Sarcoma Viral Oncogene Homolog B1 and Cyclin-Dependent Kinase 4 for Melanoma. Bhaskaran, S., et al. Mol. Cancer Ther. 12(4), 361-72, (2013)

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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. Kunnumakkara AB, Nair AS, Ahn KS, et al. Blood 109(12), 5112-21, (2007)

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Gossypin induces G2/M arrest in human malignant glioma U251 cells by the activation of Chk1/Cdc25C pathway. Shi L, Chen J, Wang YY, et al. Cell. Mol. Neurobiol. 32(2), 289-96, (2012)

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Influence of gossypin on the development of acute tolerance to morphine induced antinociception. Ramaswamy S and Viswanathan S Indian J. Exp. Biol. 35(4), 413-4, (1997)

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Anti-inflammatory and anti-allergic properties of flavonoids. Gábor M Prog. Clin. Biol. Res. 213, 471-80, (1986)

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Loss of plasmid linked antibiotic resistance in Escherichia coli on treatment with some phenolic compounds. Lakshmi VV, Sridhar P, and Polasa H FEMS Microbiol. Lett. 48(3), 275-8, (1989)

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[Effect of seven kinds of flavonoids on recombinant human protein tyrosine phosphatase]. He TP, Liang NC, Lin XC, et al. Zhong Yao Cai 33(5), 771-4, (2010)

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Anti-inflammatory activity and inhibition of arachidonic acid metabolism by flavonoids. Ferrándiz ML and Alcaraz MJ Agents Actions 32(3-4), 283-8, (1991)

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The flavonoid glycosides, myricitrin, gossypin and naringin exert anxiolytic action in mice. Fernandez SP, Nguyen M, Yow TT, et al. Neurochem. Res. 34(10), 1867-75, (2009)

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Gossypin up-regulates LDL receptor through activation of ERK pathway: a signaling mechanism for the hypocholesterolemic effect. Lu N, Li Y, Qin H, et al. J. Agric. Food Chem. 56(23), 11526-32, (2008)

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Flavonoid-induced delay in the small intestinal transit: possible mechanism of action. Viswanathan S, Thirugnana Sambantham P, Bapna JS, et al. Arch. Int. Pharmacodyn. Ther. 270(1), 151-7, (1984)

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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. Kunnumakkara AB, Nair AS, Ahn KS, et al. Blood 109(12), 5112-21, (2007)

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Oral supplementation of gossypin during lead exposure protects alteration in heme synthesis pathway and brain oxidative stress in rats. Gautam P and Flora SJ Nutrition 26(5), 563-70, (2010)

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Gossypin-induced analgesia in mice. Viswanathan S, Sambantham PT, Reddy K, et al. Eur. J. Pharmacol. 98(2), 289-91, (1984)

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Prophylactic effect of gossypin against percutaneously administered sulfur mustard. Gautam A and Vijayaraghavan R Biomed. Environ. Sci. 20(3), 250-9, (2007)

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Free radical scavenging, antitumor and anticarcinogenic activity of gossypin. Babu BH, Jayram HN, Nair MG, et al. J. Exp. Clin. Cancer Res 22(4), 581-9, (2003)

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Antiinflammatory and antinociceptive activities of gossypin and procumbentin--cyclooxygenase-2 (COX-2) inhibition studies. Mada SR, Metukuri MR, Burugula L, et al. Phytother Res. 23(6), 878-84, (2009)

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Gossypin protects primary cultured rat cortical cells from oxidative stress- and beta-amyloid-induced toxicity. Yoon I, Lee KH, and Cho J Arch. Pharm. Res. 27(4), 454-9, (2004)

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A flavonoid gossypin binds to cyclin-dependent kinase 2. Kim H, Lee E, Kim J, et al. Bioorg. Med. Chem. Lett. 18(2), 661-4, (2008)

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A study on the role of cholinergic and gamma amino butyric acid systems in the anti-nociceptive effect of gossypin. Viswanathan S, Thirugnanasambantham P, Ramaswamy S, et al. Clin. Exp. Pharmacol. Physiol. 20(3), 193-6, (1993)

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Antidiabetic activity of gossypin, a pentahydroxyflavone glucoside, in streptozotocin-induced experimental diabetes in rats. Venkatesan T and Sorimuthu Pillai S J. Diabetes 4(1), 41-6, (2012)

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Studies on possible tolerance and mechanism of gossypin analgesia. Viswanathan S, Sambandam PT, Ramaswamy S, et al. Indian J. Exp. Biol. 23(9), 525-6, (1985)

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Possible development of dependence on gossypin: role of gossypin on morphine dependence. Viswanathan S, Ramaswamy S, Thirugnasambantham P, et al. Indian J. Exp. Biol. 28(12), 1193-4, (1990)

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Evaluation of anti-allergic activity of gossypin and suramin in mast cell-mediated allergy model. Ganapaty S, Chandrashekhar VM, and Narsu ML Indian J. Biochem. Biophys. 47(2), 90-5, (2010)

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Gossypin induces G2/M arrest in human malignant glioma U251 cells by the activation of Chk1/Cdc25C pathway. Shi L, Chen J, Wang YY, et al. Cell. Mol. Neurobiol. 32(2), 289-96, (2012)

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