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SML0761

Sigma-Aldrich

Gossypin

≥90% (HPLC)

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Synonym(s):
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
Empirical Formula (Hill Notation):
C21H20O13
CAS Number:
652-78-8
Molecular Weight:
480.38
MDL number:
MFCD00017429
UNSPSC Code:
12352200
PubChem Substance ID:
329825593
NACRES:
NA.77

biological source

Hibiscus vitifolius

Assay

≥90% (HPLC)

form

powder

storage condition

desiccated

color

, light yellow to dark green-yellow

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@@H](Oc2c(O)cc(O)c3C(=O)C(O)=C(Oc23)c4ccc(O)c(O)c4)[C@H](O)[C@@H](O)[C@@H]1O

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

InChI key

SJRXVLUZMMDCNG-KKPQBLLMSA-N

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General description

Gossypin has anti-inflammatory properties. It inhibits galactose-induced cataract formation and reduces β-amyloid-induced toxicity. Gossypin provides protection against carbon tetrachloride-induced toxicity and bis(2-choloroethyl) sulfide-induced dermal toxicity. It also induces apoptosis in myeloma cells. Gossypin has an anticonvulsant property.

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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.
Molecular Cancer Therapeutics (2013)
Kuei-Chuan Chan et al.
Journal of the science of food and agriculture, 96(2), 381-391 (2015-01-24)
Previous studies have shown that mulberry polyphenolic compounds have an anti-atherosclerotic effect in rabbits. Apoptosis of vascular smooth muscle cells (VSMCs) is the key determinant of the number of VSMCs in remodeling. To examine the effect of mulberry polyphenol extracts
Anticonvulsant activity of bioflavonoid gossypin
Bangladesh Journal of Pharmacology, 4(1), 51-54 (2013)
Gema Núñez-López et al.
Enzyme and microbial technology, 122, 19-25 (2019-01-15)
Fructosylation can significantly improve the solubility, stability and bioactivity of phenolic compounds, increasing their health benefits. Levansucrase from Gluconacetobacter diazotrophicus (LsdA, EC 2.4.1.10) was found to transfer the fructosyl unit of sucrose to different classes of phenolic compounds. Among the
Saad Mustafa et al.
International journal of biological macromolecules, 143, 11-29 (2019-12-08)
Fucoidan, a macromolecule, a type of polysaccharide and contains high percentage of fucose and sulfate ester groups and other compounds in low percentage. In the last decades, a number of interesting biological activities have been studied so fucoidan has been
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