Gossypetin

Not to be confused with Gossypol.
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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
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).
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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] 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]

  1. ^ "Antibacterial activity of gossypetin isolated from hibiscus sabdariffa". Archived from the original on 2007-12-05. Retrieved 2008-04-23.
  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)