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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
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
C15 H10 O8
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).
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
^
Antibacterial activity of gossypetin isolated from hibiscus sabdariffa
^ 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)
Flavonols and their conjugates
Backbone
Flavonols
O -Methylated flavonols
Derivative flavonols
Pyranoflavonols
Furanoflavonols
Semisynthetic
Angiopoietin
CNTF
EGF (ErbB)
FGF
FGFR1
FGFR2
Agonists:
Ersofermin
FGF (
1 ,
2 (bFGF) ,
3 ,
4 ,
5 ,
6 ,
7 (
KGF ),
8 ,
9 ,
10 (KGF2) ,
17 ,
18 ,
22 )
Palifermin
Repifermin
Selpercatinib
Sprifermin
Trafermin
FGFR3
FGFR4 Unsorted
HGF (c-Met)
IGF
LNGF (p75NTR )
PDGF
RET (GFL)
SCF (c-Kit)
TGFβ
Trk
TrkA
Negative allosteric modulators:
VM-902A
TrkB
Agonists:
3,7-DHF
3,7,8,2'-THF
4'-DMA-7,8-DHF
7,3'-DHF
7,8-DHF
7,8,2'-THF
7,8,3'-THF
Amitriptyline
BDNF
BNN-20
Deoxygedunin
Deprenyl
Diosmetin
DMAQ-B1
HIOC
LM22A-4
N-Acetylserotonin
NT-3
NT-4
Norwogonin (5,7,8-THF)
R7
R13
TDP6
TrkC
VEGF Others
Additional growth factors:
Adrenomedullin
Colony-stimulating factors (see
here instead)
Connective tissue growth factor (CTGF)
Ephrins (
A1 ,
A2 ,
A3 ,
A4 ,
A5 ,
B1 ,
B2 ,
B3 )
Erythropoietin (see
here instead)
Glucose-6-phosphate isomerase (GPI; PGI, PHI, AMF)
Glia maturation factor (GMF)
Hepatoma-derived growth factor (HDGF)
Interleukins /
T-cell growth factors (see
here instead)
Leukemia inhibitory factor (LIF)
Macrophage-stimulating protein (MSP; HLP, HGFLP)
Midkine (NEGF2)
Migration-stimulating factor (MSF; PRG4)
Oncomodulin
Pituitary adenylate cyclase-activating peptide (PACAP)
Pleiotrophin
Renalase
Thrombopoietin (see
here instead)
Wnt signaling proteins
Additional growth factor receptor modulators:
Cerebrolysin (neurotrophin mixture)