Gossypetin

Gossypetin
Skeletal formula of gossypetin
Ball-and-stick model of the gossypetin molecule
Names
IUPAC name
3,3′,4′,5,7,8-Hexahydroxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4H-1-benzopyran-4-one
Other names
Articulatidin
Equisporol
3,5,7,8,3',4'-Hexahydroxyflavone
Identifiers
CAS Number
  • 489-35-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16400 ☒N
ChEMBL
  • ChEMBL253570 ☒N
ChemSpider
  • 4444247 ☒N
PubChem CID
  • 5280647
UNII
  • SET4M23ZTM checkY
CompTox Dashboard (EPA)
  • DTXSID50197631 Edit this at Wikidata
InChI
  • 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 ☒N
    Key: YRRAGUMVDQQZIY-UHFFFAOYSA-N ☒N
  • InChI=1/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
    Key: YRRAGUMVDQQZIY-UHFFFAOYAI
  • C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O)O
Properties
Chemical formula
C15H10O8
Molar mass 318.23 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

Gossypetin, also known as 3,5,7,8,3',4'-hexahydroxyflavone, is a flavonol, a type of flavonoid. It has been isolated from the flowers and the calyx of Hibiscus sabdariffa (roselle) and exhibits a strong antibacterial activity.[1][2] The compound has also been found to act as an antagonist of TrkB.[3] Recently it was shown that gossypetin has radioprotective activity.[citation needed]

The enzyme 8-hydroxyquercetin 8-O-methyltransferase uses S-adenosyl methionine and gossypetin to produce S-adenosylhomocysteine and 3,5,7,3',4'-pentahydroxy-8-methoxyflavone.[citation needed]

In 2022, a study in an animal model using intragastric administration suggested that the flavonoid gossypetin facilitated the clearance of beta-amyloid in the brain and is a promising target for the study of treatments for Alzheimer's Disease by enhancing microglial phagocytic activity against Aβ.[4]

See also

References

  1. ^ Antibacterial activity of gossypetin isolated from hibiscus sabdariffa
  2. ^ Amitava Khan, Krishnendu Manna, Chinchubose, Mahuya Sinha, Dipesh Kr Das, Swaraj Bandhu Kesh, Anindita Chakrabarty, Asoke Banerji & Sanjit Dey: Gossypetin, a naturally occurring hexahydroxy flavones ameliorates gamma radiation mediated DNA damage International Journal of Radiation Biology (2013):89(11): 965-975.
  3. ^ Obianyo, Obiamaka; Ye, Keqiang (2013). "Novel small molecule activators of the Trk family of receptor tyrosine kinases". Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics. 1834 (10): 2213–2218. doi:10.1016/j.bbapap.2012.08.021. ISSN 1570-9639. PMC 3602283. PMID 22982231.
  4. ^ Jo, K.W., Lee, D., Cha, D.G. et al., Gossypetin ameliorates 5xFAD spatial learning and memory through enhanced phagocytosis against Aβ, Alzheimer's Research & Therapy, October 21, 2022 - Alz Res Therapy 14, 158 (2022)
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Flavonols and their conjugates
Backbone
Aglycones
Flavonols
Aglycones
Conjugates
Glycosides of herbacetin
Glycosides of kaempferol
  • Afzelin (Kaempferol 3-rhamnoside)
  • Astragalin (kaempferol 3-O-glucoside)
  • Kaempferitrin (kaempferol 3,7-dirhamnoside)
  • Juglanin (Kaempferol 3-O-arabinoside)
  • Kaempferol 3-alpha-L-arabinopyranoside
  • Kaempferol 3-alpha-D-arabinopyranoside
  • Kaempferol 7-alpha-L-arabinoside
  • Kaempferol 7-O-glucoside
  • Kaempferol 3-lathyroside
  • Kaempferol 4'-rhamnoside
  • Kaempferol 5-rhamnoside
  • Kaempferol 7-rhamnoside
  • Kaempferol 7-O-alpha-L-rhamnofuranoside
  • Kaempferol 3-xyloside
  • Kaempferol 7-xyloside
  • Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
  • Kaempferol 3-O-rutinoside
  • Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
  • Trifolin (Kaempferol 3-O-beta-D-galactoside)
Glycosides of myricetin
Conjugates of quercetin
Sulfates
Glycosides
O-Methylated flavonols
Aglycones
Glycosides
of isorhamnetin
  • Narcissin (Isorhamnetin 3-O-rutinoside)
  • Isorhamnetin 3-O-glucoside
  • Tamarixetin 7-rutinoside
other
  • Azalein (Azaleatin 3-O-α-L-rhamnoside)
  • Centaurein (Centaureidin 7-O-glucoside)
  • Eupalin (Eupalitin 3-0-rhamnoside)
  • Eupatolin (Eupatolitin 3-O-rhamnoside)
  • Jacein (Jaceidin 7-O-glucoside)
  • Patulitrin (Patuletin 7-O-glucoside
  • Xanthorhamnin (Rhamnetin glycoside)
Derivative flavonols
Aglycones
  • Noricaritin
  • Dihydronoricaritin
Glycosides
  • Amurensin
  • Icariin
  • Phelloside
  • Dihydrophelloside
  • Rutin S
Pyranoflavonols
Aglycones
Furanoflavonols
Aglycones
Glycosides
  • Pongamoside A, B and C
Semisynthetic
Glycosides
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Angiopoietin
  • Kinase inhibitors: Altiratinib
  • CE-245677
  • Rebastinib
CNTF
EGF (ErbB)
EGF
(ErbB1/HER1)
ErbB2/HER2
  • Agonists: Unknown/none
ErbB3/HER3
ErbB4/HER4
FGF
FGFR1
FGFR2
  • Antibodies: Aprutumab
  • Aprutumab ixadotin
FGFR3
FGFR4
Unsorted
HGF (c-Met)
IGF
IGF-1
  • Kinase inhibitors: BMS-754807
  • Linsitinib
  • NVP-ADW742
  • NVP-AEW541
  • OSl-906
IGF-2
  • Antibodies: Dusigitumab
  • Xentuzumab (against IGF-1 and IGF-2)
Others
  • Cleavage products/derivatives with unknown target: Glypromate (GPE, (1-3)IGF-1)
  • Trofinetide
LNGF (p75NTR)
  • Aptamers: Against NGF: RBM-004
  • Decoy receptors: LEVI-04 (p75NTR-Fc)
PDGF
RET (GFL)
GFRα1
GFRα2
GFRα3
GFRα4
Unsorted
  • Kinase inhibitors: Agerafenib
SCF (c-Kit)
TGFβ
  • See here instead.
Trk
TrkA
  • Negative allosteric modulators: VM-902A
  • Aptamers: Against NGF: RBM-004
  • Decoy receptors: ReN-1820 (TrkAd5)
TrkB
TrkC
VEGF
Others


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