Kaempferol 7-O-glucoside

Last updated
Kaempferol 7-O-glucoside
Kaempferol 7-O-glucoside.svg
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
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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
  • 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
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).

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

  1. ↑ 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.
  2. ↑ 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. Bibcode:1973BioSE...1...51H. doi:10.1016/0305-1978(73)90035-5.
  3. ↑ 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): 1118–1121. doi: 10.1248/cpb.53.1118 . PMID   16141579.
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