Gossypetin

{{Distinguish|Gossypol}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 400270518

| Name = Gossypetin

| ImageFile = Gossypetin.svg

| ImageSize = 250px

| ImageAlt = Skeletal formula of gossypetin

| ImageFile1 = Gossypetin-3D-balls.png

| ImageAlt1 = Ball-and-stick model of the gossypetin molecule

| IUPACName = 3,3′,4′,5,7,8-Hexahydroxyflavone

| SystematicName = 2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4H-1-benzopyran-4-one

| OtherNames = Articulatidin
Equisporol
3,5,7,8,3',4'-Hexahydroxyflavone

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 489-35-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = SET4M23ZTM

| PubChem = 5280647

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 253570

| SMILES = C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O)O

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4444247

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 16400

| 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

| InChIKey = YRRAGUMVDQQZIY-UHFFFAOYAI

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = YRRAGUMVDQQZIY-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula = C₁₅H₁₀O₈

| MolarMass = 318.23 g/mol

| Appearance =

| Density =

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|Section3={{Chembox Hazards

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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.{{Cite web |url=http://medind.nic.in/imvw/imvw289.html |title=Antibacterial activity of gossypetin isolated from hibiscus sabdariffa |access-date=2008-04-23 |archive-date=2007-12-05 |archive-url=https://web.archive.org/web/20071205051151/http://medind.nic.in/imvw/imvw289.html |url-status=dead }}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. The compound has also been found to act as an antagonist of TrkB.{{cite journal|last1=Obianyo|first1=Obiamaka|last2=Ye|first2=Keqiang|title=Novel small molecule activators of the Trk family of receptor tyrosine kinases|journal=Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics|volume=1834|issue=10|year=2013|pages=2213–2218|issn=1570-9639|doi=10.1016/j.bbapap.2012.08.021|pmc=3602283|pmid=22982231}} Gossypetin has radioprotective activity.{{Citation needed|date=November 2017}}

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|date=November 2016}}

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.{{cite journal | doi=10.1186/s13195-022-01096-3 | doi-access=free | title=Gossypetin ameliorates 5xFAD spatial learning and memory through enhanced phagocytosis against Aβ | date=2022 | last1=Jo | first1=Kyung Won | last2=Lee | first2=Dohyun | last3=Cha | first3=Dong Gon | last4=Oh | first4=Eunji | last5=Choi | first5=Yoon Ha | last6=Kim | first6=Somi | last7=Park | first7=Eun Seo | last8=Kim | first8=Jong Kyoung | last9=Kim | first9=Kyong-Tai | journal=Alzheimer's Research & Therapy | volume=14 | issue=1 | page=158 | pmid=36271414 | pmc=9585741 }}