Gossypetin

Gossypetin
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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16400 ;
ChEMBL	ChEMBL253570 ;
ChemSpider	4444247 ;
PubChem CID	5280647;
UNII	SET4M23ZTM ;
CompTox Dashboard (EPA)	DTXSID50197631 ;
	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 Key: YRRAGUMVDQQZIY-UHFFFAOYSA-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;
	SMILES 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). verify (what is ?) Infobox references

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]

References

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

[ObianyoYe2013-3] 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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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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16400^N
ChEMBL	ChEMBL253570^N
ChemSpider	4444247^N
PubChem CID	5280647
UNII	SET4M23ZTM^Y
CompTox Dashboard (EPA)	DTXSID50197631
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
SMILES 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 ^YN ?) Infobox references

Gossypetin

See also

References

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