114297-65-3
Chemical Structure
6-O-(E)-p-Hydroxy-cinnamoyl-glucose
- CAS No.: 114297-65-3
- Formula:C15H18O8
- Molecular Weight:326.30
IUPAC Name: (2R,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexyl (E)-3-(4-hydroxyphenyl)acrylate
InChIKey: NKAUYEOJVXZPIW-ZZPZHBAMSA-N
SMILES: C(=C/C(OC[C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)O)=O)\C1=CC=C(O)C=C1
Biological Activity: 6-O-(E)-p-Hydroxy-cinnamoyl-glucose is a phenylpropanoid glycoside isolated from Aristolochia manshuriensis Kom., acting as a free radical scavenger. 6-O-(E)-p-Hydroxy-cinnamoyl-glucose scavenges hydrated electrons, sulfate radical anions, and hydroxyl radicals by forming phenoxyl radicals at its conjugated carbonyl/keto group. 6-O-(E)-p-Hydroxy-cinnamoyl-glucose repairs oxidative DNA damage, DNA radical cations and anions, as well as deoxynucleotide radical cations (dAMP, dGMP, dCMP) and anions through electron transfer. 6-O-(E)-p-Hydroxy-cinnamoyl-glucose is useful for research on DNA damage-related diseases[1][2][3][4][5][6][7].
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6-O-(E)-p-Hydroxy-cinnamoyl-glucose | 6-O-(E)-p-Hydroxy-cinnamoyl-glucose is a phenylpropanoid glycoside isolated from Aristolochia manshuriensis Kom., acting as a free radical scavenger. 6-O-(E)-p-Hydroxy-cinnamoyl-glucose scavenges hydrated electrons, sulfate radical anions, and hydroxyl radicals by forming phenoxyl radicals at its conjugated carbonyl/keto group. 6-O-(E)-p-Hydroxy-cinnamoyl-glucose repairs oxidative DNA damage, DNA radical cations and anions, as well as deoxynucleotide radical cations (dAMP, dGMP, dCMP) and anions through electron transfer. 6-O-(E)-p-Hydroxy-cinnamoyl-glucose is useful for research on DNA damage-related diseases. | |||||||||||||||||||||
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References
- [1]. Shi Y, et al. Fast repair of TMP radical anions by phenylpropanoid glycosides (PPGs) and their analogs. Radiation Physics and Chemistry. 2000 Apr;58(2):131‑138.
- [2]. Shi Y, et al. Fast repair of oxidative DNA damage by phenylpropanoid glycosides and their analogues. Mutagenesis. 2008 Jan;23(1):19-26.
- [3]. Shi Y, et al. Fast repair of deoxynucleotide radical cations by phenylpropanoid glycosides (PPGs) and their analogs. Biochimica et biophysica acta. 1999 Oct 18;1472(1-2):279-89.
- [4]. Shi Y, et al. Reaction of hydroxyl radical with phenylpropanoid glycoside and its derivatives by pulse radiolysis. Science in China. Series C, Life sciences. 1999 Aug;42(4):420-6.
- [5]. Sperandio O, et al. Theoretical study of fast repair of DNA damage by cistanoside C and analogs: mechanism and docking. SAR QSAR Environ Res. 2002 Mar;13(2):243-60. [Content Brief]
- [6]. Shi Y, et al. Dietary phytophenols act as scavengers of reducing radicals. Food Chemistry. 2011 Feb 15;124(4):1322‑1327.
- [7]. Shi Y, et al. Fast repair of dAMP radical anions by phenylpropanoid glycosides and their analogs. Biochimica et biophysica acta. 2000 May 01;1474(3):383-9.
