Comparative studies on the interaction of caffeic acid, chlorogenic acid and ferulic acid with bovine serum albumin.
The substitution of the hydrogen on aromatic and esterification of carboxyl group of the phenol compounds plays an important role in their bio-activities. In this paper, caffeic acid (CaA), chlorogenic acid (ChA) and ferulic acid (FA) were selected to investigate the binding to bovine serum albumin (BSA) using UV absorption spectroscopy, fluorescence spectroscopy and synchronous fluorescence spectroscopy. It was found that the methoxyl group substituting for the 3-hydroxyl group of CaA decreased the affinity for BSA and the esterification of carboxyl group of CaA with quinic acid increased the affinities. The affinities of ChA and FA with BSA were more sensitive to the temperature than that of CaA with BSA. Synchronous fluorescence spectroscopy and time-resolved fluorescence indicated that the Stern-Volmer plots largely deviated from linearity at high concentrations and were caused by complete quenching of the tyrosine fluorescence of BSA.
Li
Shuang
S
Central South University, Changsha, Hunan 410083, People's Republic China. lishuang 5058@yahoo.com.cn
Huang
Kelong
K
Zhong
Ming
M
Guo
Jun
J
Wang
Wei-zheng
WZ
Zhu
Ronghua
R
D000818:Animals; D002109:Caffeic Acids / Q000737:chemistry / Q000494:pharmacology*; D002417:Cattle; D002726:Chlorogenic Acid / Q000737:chemistry / Q000494:pharmacology*; D003373:Coumaric Acids / Q000737:chemistry / Q000494:pharmacology*; D011485:Protein Binding; D012710:Serum Albumin, Bovine / Q000737:chemistry / Q000187:drug effects*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D013696:Temperature; D014443:Tyrosine / Q000737:chemistry
D002109:Caffeic Acids; D003373:Coumaric Acids; D012710:Serum Albumin, Bovine; D002726:Chlorogenic Acid; D014443:Tyrosine; C004999:ferulic acid; C040048:caffeic acid