Gossypetin

Gossypetin
Names


IUPAC name 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxychromen-4-one
Other names Articulatidin Equisporol 3,3',4',5,7,8-Hexahydroxyflavone 3,5,7,8,3',4'-Hexahydroxyflavone
Identifiers
CAS Number	489-35-0^Y
ChEBI	CHEBI:16400^N
ChEMBL	ChEMBL253570^N
ChemSpider	4444247^N
Jmol interactive 3D	Image
PubChem	5280647
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 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]

Gosspetin has been found to act as an antagonist of TrkB.^[3]

Metabolism

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. Recently it was shown that gossypetin has radioprotective activity.

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.

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates	Quercetin 3-O-sulfate Quercetin 3,3'-bissulfate Quercetin 3,4'-bissulfate

Glycosides	Avicularin (quercetin-3-O-α-L-arabinofuranoside) CTN-986 Guaijaverin (quercetin 3-O-arabinoside) Heliosin (quercetin 3-digalactoside) Hyperoside (quercetin 3-O-galactoside) Isoquercetin (quercetin 3-O-glucoside) Miquelianin (quercetin 3-O-glucuronide) Quercetin 3,4'-diglucoside Quercetin-3-sophorodide Quercitrin (quercetin 3-O-rhamnoside) Rutin (quercetin rutinoside) Reinutrin (quercetin-3-D-xyloside) Spiraeoside (quercetin 4'-O-glucoside) Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside

other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)

Derivative flavonols

Aglycones	Noricaritin Dihydronoricaritin

Glycosides	Amurensin Icariin Phelloside Dihydrophelloside Rutin S

Pyranoflavonols

Aglycones	Karanjachromene

Furanoflavonols

Aglycones	Karanjin

Glycosides	Pongamoside A, B and C

Semisynthetic

Glycosides	Hydroxyethylrutosides Monoxerutin Troxerutin

Neurotrophinergics

CNTF

Agonists: Axokine
CNTF

LNGF

Agonists: BDNF
NGF
NT-3
NT-4

Antagonists: SAR127963

RET

GFRα1	Agonists: GDNF

GFRα2	Agonists: Neurturin (NRTN)

GFRα3	Agonists: Artemin (ARTN)

GFRα4	Agonists: Persephin (PSPN)

Trk

TrkA	Agonists: Amitriptyline Gambogic amide NGF Tavilermide Antagonists: FX007

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 Deoxygedunin Diosmetin HIOC LM22A-4 N-Acetylserotonin NT-3 NT-4 Norwogonin (5,7,8-THF) R7 TDP6 Antagonists: ANA-12 Cyclotraxin B Gossypetin (3,5,7,8,3',4'-HHF) Inhibitors: K252a

TrkC	Agonists: NT-3

Others

Antibodies: Tanezumab (against NGF)

Others: Cerebrolysin (neurotrophin mixture)

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Gossypetin

Metabolism

See also

References