Page last updated: 2024-11-10

gossypin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

gossypin: do not confuse with gossypin(e) which is synonym for choline [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

gossypin : A glycosyloxyflavone that is gossypetin attached to a beta-D-glucopyranosyl residue at position 8 via a glycosidic linkage. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5281621
CHEMBL ID402915
CHEBI ID5525
SCHEMBL ID1156121
MeSH IDM0079659

Synonyms (39)

Synonym
brn 0071526
2-(3,4-dihydroxyphenyl)-8-(beta-d-glucopyranosyloxy)-3,5,7-trihydroxy-4h-1-benzopyran-4-one
nsc 656276
4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-(beta-d-glucopyranosyloxy)-3,5,7-trihydroxy-
gossypetin-8-glucoside
652-78-8
C10051
gossypin
gossypetin 8-o-glucoside
4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-(.beta.-d-glucopyranosyloxy)-3,5,7-trihydroxy-
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
CHEMBL402915
chebi:5525 ,
gossypetin 8-glucoside
ST057186 ,
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
unii-a3q367xwx9
3,5,7,8,3',4'-hexahydroxyflavone-8-glucoside
a3q367xwx9 ,
4-18-00-03589 (beilstein handbook reference)
3,3',4',5,7,8-hexahydroxyflavone 8-glucoside
BRD-K05485208-001-01-1
gossypin (4)
bdbm153264
SCHEMBL1156121
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxo-4h-1-benzopyran-8-yl beta-d-glucopyranoside
AKOS024282592
2-(3,4-dihydroxy-phenyl)-3,5,7-trihydroxy-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromen-4-one
A1-00786
SJRXVLUZMMDCNG-KKPQBLLMSA-N
3,3',4',5,7,8-hexahydroxyflavone-8-glucoside
mfcd00017429
DTXSID60215512
HY-125911
CS-0102990
gossypin, >=90% (hplc)
Q27106791
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one
MS-28931

Research Excerpts

Overview

Gossypin is a flavone extracted from Hibiscus vitifolius. It has been reported to exhibit anti-inflammatory, antioxidant, and anticancer activities. GossypIn is a promising agent for the treatment of LPS induced lung inflammation via altering Nrf2/HO-1 and NF-κB.

ExcerptReferenceRelevance
"Gossypin is a promising agent for the treatment of LPS induced lung inflammation via altering Nrf2/HO-1 and NF-κB."( Gossypin exert lipopolysaccharide induced lung inflammation via alteration of Nrf2/HO-1 and NF-κB signaling pathway.
Fan, Y; Gangireddygari, VSR; Huang, H; Hussain, SA; Wang, J, 2023
)
3.07
"Gossypin is a flavone extracted from Hibiscus vitifolius, which has been reported to exhibit anti-inflammatory, antioxidant, and anticancer activities. "( Gossypin inhibits gastric cancer growth by direct targeting of AURKA and RSK2.
Bode, AM; Chen, H; Dong, Z; Kim, DJ; Liu, K; Ma, F; Wang, L; Wang, X; Zu, X, 2019
)
3.4
"Gossypin is a flavone that was originally isolated from Hibiscus vitifolius and has traditionally been used for the treatment of diabetes, jaundice, and inflammation. "( Gossypin induces G2/M arrest in human malignant glioma U251 cells by the activation of Chk1/Cdc25C pathway.
Chen, J; Fu, Z; Liu, JN; Liu, N; Qian, CF; Shi, L; Sun, G; Wang, YY; Yan, W; You, YP; Zeng, Y; Zhang, JX, 2012
)
3.26

Actions

ExcerptReferenceRelevance
"Gossypin was found to inhibit the oxidative neuronal damage induced by xanthine/xanthine oxidase or by a glutathione depleting agent, D,L-buthionine (S,R)-sulfoximine."( Gossypin protects primary cultured rat cortical cells from oxidative stress- and beta-amyloid-induced toxicity.
Cho, J; Lee, KH; Yoon, I, 2004
)
2.49

Treatment

Gossypin treatment significantly (p < .001) reduced the W/D ratio of lung tissue and lung index. The drug attenuated the acute tolerance development to morphine induce antinociceptive response.

ExcerptReferenceRelevance
"Gossypin treatment significantly (p < .001) reduced the W/D ratio of lung tissue and lung index."( Gossypin exert lipopolysaccharide induced lung inflammation via alteration of Nrf2/HO-1 and NF-κB signaling pathway.
Fan, Y; Gangireddygari, VSR; Huang, H; Hussain, SA; Wang, J, 2023
)
3.07
"Gossypin pre-treatment significantly attenuated the acute tolerance development to morphine induce antinociceptive response."( Influence of gossypin on the development of acute tolerance to morphine induced antinociception.
Ramaswamy, S; Viswanathan, S, 1997
)
1.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
neuroprotective agentAny compound that can be used for the treatment of neurodegenerative disorders.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
7-hydroxyflavonolAny flavonol carrying a 7-hydroxy substituent.
pentahydroxyflavoneA hydroxyflavone substituted by five hydroxy groups.
glycosyloxyflavoneA member of the class of flavones having one or more glycosyl residues attached at unspecified positions.
monosaccharide derivativeA carbohydrate derivative that is formally obtained from a monosaccharide.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aurora kinase BHomo sapiens (human)IC50 (µMol)11.07000.00030.96349.8000AID1801097
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IIAurora kinase BHomo sapiens (human)
mitotic cell cycleAurora kinase BHomo sapiens (human)
mitotic cytokinesisAurora kinase BHomo sapiens (human)
negative regulation of B cell apoptotic processAurora kinase BHomo sapiens (human)
protein phosphorylationAurora kinase BHomo sapiens (human)
spindle organizationAurora kinase BHomo sapiens (human)
attachment of spindle microtubules to kinetochoreAurora kinase BHomo sapiens (human)
abscissionAurora kinase BHomo sapiens (human)
negative regulation of protein bindingAurora kinase BHomo sapiens (human)
positive regulation of telomere maintenance via telomeraseAurora kinase BHomo sapiens (human)
negative regulation of cytokinesisAurora kinase BHomo sapiens (human)
positive regulation of cytokinesisAurora kinase BHomo sapiens (human)
protein localization to kinetochoreAurora kinase BHomo sapiens (human)
cellular response to UVAurora kinase BHomo sapiens (human)
cleavage furrow formationAurora kinase BHomo sapiens (human)
post-translational protein modificationAurora kinase BHomo sapiens (human)
cell cycle G2/M phase transitionAurora kinase BHomo sapiens (human)
mitotic cytokinesis checkpoint signalingAurora kinase BHomo sapiens (human)
negative regulation of innate immune responseAurora kinase BHomo sapiens (human)
protein autophosphorylationAurora kinase BHomo sapiens (human)
mitotic spindle midzone assemblyAurora kinase BHomo sapiens (human)
positive regulation of telomerase activityAurora kinase BHomo sapiens (human)
regulation of chromosome segregationAurora kinase BHomo sapiens (human)
positive regulation of mitotic sister chromatid segregationAurora kinase BHomo sapiens (human)
positive regulation of mitotic cell cycle spindle assembly checkpointAurora kinase BHomo sapiens (human)
mitotic spindle assemblyAurora kinase BHomo sapiens (human)
negative regulation of cGAS/STING signaling pathwayAurora kinase BHomo sapiens (human)
regulation of signal transduction by p53 class mediatorAurora kinase BHomo sapiens (human)
positive regulation of mitotic sister chromatid separationAurora kinase BHomo sapiens (human)
positive regulation of attachment of mitotic spindle microtubules to kinetochoreAurora kinase BHomo sapiens (human)
positive regulation of mitotic cytokinesisAurora kinase BHomo sapiens (human)
positive regulation of telomere cappingAurora kinase BHomo sapiens (human)
positive regulation of lateral attachment of mitotic spindle microtubules to kinetochoreAurora kinase BHomo sapiens (human)
mitotic spindle organizationAurora kinase BHomo sapiens (human)
regulation of cytokinesisAurora kinase BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
protein serine/threonine kinase activityAurora kinase BHomo sapiens (human)
protein serine/threonine kinase activityAurora kinase BHomo sapiens (human)
protein serine/threonine/tyrosine kinase activityAurora kinase BHomo sapiens (human)
protein bindingAurora kinase BHomo sapiens (human)
ATP bindingAurora kinase BHomo sapiens (human)
kinase bindingAurora kinase BHomo sapiens (human)
protein serine kinase activityAurora kinase BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
kinetochoreAurora kinase BHomo sapiens (human)
condensed chromosome, centromeric regionAurora kinase BHomo sapiens (human)
nucleusAurora kinase BHomo sapiens (human)
nucleoplasmAurora kinase BHomo sapiens (human)
spindleAurora kinase BHomo sapiens (human)
cytosolAurora kinase BHomo sapiens (human)
chromocenterAurora kinase BHomo sapiens (human)
microtubule cytoskeletonAurora kinase BHomo sapiens (human)
midbodyAurora kinase BHomo sapiens (human)
chromosome passenger complexAurora kinase BHomo sapiens (human)
mitotic spindle poleAurora kinase BHomo sapiens (human)
mitotic spindle midzoneAurora kinase BHomo sapiens (human)
kinetochoreAurora kinase BHomo sapiens (human)
spindle pole centrosomeAurora kinase BHomo sapiens (human)
spindle microtubuleAurora kinase BHomo sapiens (human)
spindle midzoneAurora kinase BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1801097Aurora B Kinase Assay from Article 10.1111/cbdd.12445: \\Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships.\\2015Chemical biology & drug design, May, Volume: 85, Issue:5
Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships.
AID616482Antioxidant activity assessed as DPPH free radical scavenging activity2011Bioorganic & medicinal chemistry letters, Sep-15, Volume: 21, Issue:18
Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs.
AID313793Binding affinity to human CDK22008Bioorganic & medicinal chemistry letters, Jan-15, Volume: 18, Issue:2
A flavonoid gossypin binds to cyclin-dependent kinase 2.
AID622584Inhibition of NF-kappaB activation expressed in HCT116 cells assessed as inhibition of TNF-alpha-induced transcriptional activation at 10 uM after 12 hrs by luciferase reporter gene assay relative to control2011Bioorganic & medicinal chemistry letters, Oct-15, Volume: 21, Issue:20
Relationship between the structures of flavonoids and their NF-κB-dependent transcriptional activities.
AID1668637Inhibition of human liver FBP1 at 200 uM incubated for 5 mins by fluorescence method relative to control2020Journal of natural products, 05-22, Volume: 83, Issue:5
Structural Specificity of Flavonoids in the Inhibition of Human Fructose 1,6-Bisphosphatase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (37)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (18.92)18.7374
1990's4 (10.81)18.2507
2000's8 (21.62)29.6817
2010's13 (35.14)24.3611
2020's5 (13.51)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 45.74

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index45.74 (24.57)
Research Supply Index3.66 (2.92)
Research Growth Index4.81 (4.65)
Search Engine Demand Index69.20 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (45.74)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.63%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other37 (97.37%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]