Kaempferol 7-O-glucoside

Kaempferol 7-O-glucoside
Names

IUPAC name 7-(β-D-Glucopyranosyloxy)-3,4′,5-trihydroxyflavone
Systematic IUPAC name 3,5-Dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names Kaempferol-7-O-beta-D-glucoside
Identifiers
CAS Number	16290-07-6^Y
3D model (JSmol)	Interactive image
ChemSpider	8270716
PubChem CID	10095180
UNII	RZF1QN1Z8R^Y
InChI InChI=1S/C21H20O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17,19,21-25,27-29H,7H2/t13-,15-,17+,19-,21-/m1/s1 Key: YPWHZCPMOQGCDQ-HMGRVEAOSA-N InChI=1/C21H20O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17,19,21-25,27-29H,7H2/t13-,15-,17+,19-,21-/m1/s1 Key: YPWHZCPMOQGCDQ-HMGRVEAOBK
SMILES C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
Properties
Chemical formula	C₂₁H₂₀O₁₁
Molar mass	448.380 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Kaempferol 7-O-glucoside is a flavonol glucoside. It can be found in Smilax china,^[1] and in the fern Asplenium rhizophyllum, and its hybrid descendants, as part of a complex with caffeic acid.^[2]

Derivatives

Amurensin is the tert-amyl alcohol derivative of kaempferol 7-O-glucoside. 6'''-O-acetyl amurensin is found in the leaves of Phellodendron japonicum.^[3]

References

^ Xu, W.; Liu, J.; Li, C.; Wu, H. Z.; Liu, Y. W. (2008). "Kaempferol-7-O-β-d-glucoside (KG) isolated from Smilax china L. rhizome induces G2/M phase arrest and apoptosis on HeLa cells in a p53-independent manner". Cancer Letters. 264 (2): 229–240. doi:10.1016/j.canlet.2008.01.044. PMID 18343026.
^ Harborne, Jeffrey B.; Williams, Christine A.; Smith, Dale M. (1973). "Species-specific kaempferol derivatives in ferns of the Appalachian Asplenium complex". Biochemical Systematics and Ecology. 1 (1): 51–54. doi:10.1016/0305-1978(73)90035-5.
^ Chiu, C. Y.; Li, C. Y.; Chiu, C. C.; Niwa, M.; Kitanaka, S.; Damu, A. G.; Lee, E. J.; Wu, T. S. (2005). "Constituents of Leaves of Phellodendron japonicum MAXIM. And Their Antioxidant Activity". Chemical & Pharmaceutical Bulletin. 53 (9): 1118. doi:10.1248/cpb.53.1118.

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Fisetin
Galangin
Gossypetin
Herbacetin
Kaempferol
Morin
Myricetin
Quercetagetin
Quercetin
Robinetin

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)