Gossypetin

Last updated
Gossypetin
Gossypetin.svg
Gossypetin-3D-balls.png
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
PubChem CID
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 X mark.svgN
    Key: YRRAGUMVDQQZIY-UHFFFAOYSA-N X mark.svgN
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

See also

Related Research Articles

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<span class="mw-page-title-main">Tropomyosin receptor kinase B</span> Protein and coding gene in humans

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<span class="mw-page-title-main">Deoxygedunin</span> Chemical compound

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<span class="mw-page-title-main">R13 (drug)</span> Chemical compound

R13 is a small-molecule flavonoid and orally active, potent, and selective agonist of the tropomyosin receptor kinase B (TrkB) – the main signaling receptor for the neurotrophin brain-derived neurotrophic factor (BDNF) – which is under development for the potential treatment of Alzheimer's disease. It is a structural modification and prodrug of tropoflavin (7,8-DHF) with improved potency and pharmacokinetics, namely oral bioavailability and duration. The compound is a replacement for the earlier tropoflavin prodrug R7 and has similar properties to it. It was developed because while R7 displayed a good drug profile in animal studies, it showed almost no conversion into tropoflavin in human liver microsomes. In contrast to R7, R13 is readily hydrolyzed into tropoflavin in human liver microsomes.

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References

  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)