TY - JOUR
T1 - Antioxidant properties of modified rutin esters by DPPH, reducing power, iron chelation and human low density lipoprotein assays
AU - Lue, Bena-Marie
AU - Nielsen, Nina Skall
AU - Jacobsen, Charlotte
AU - Hellgren, Lars
AU - Guo, Zheng
AU - Xu, Xuebing
PY - 2010
Y1 - 2010
N2 - Practical limitations exist regarding the effectiveness of flavonoids as antioxidants in many food systems, possibly due to their poor solubility and miscibility in lipidic environments. Current strategies to improve these properties include enzymatically acylating flavonoids with lipophilic moieties. Herein, two derivatives of rutin (possessing C12:0 or C16:0 acyl groups) were assessed for their antioxidant properties, and compared with their parent compound, rutin and with butylated hydroxytoluene (BHT). While all compounds exhibited relatively strong radical scavenging abilities, modified rutin compounds exhibited decreased reducing power and metal chelating abilities as compared to rutin. Conversely, investigations on the oxidation of human low density lipoprotein (LDL) revealed that rutin laurate was most effective in inhibiting oxidation by prolonging LDL lag time for an in vitro system. With regards to in vivo considerations, a pre-treatment step confirmed that the ester bond linking rutin and acyl moieties was most susceptible to hydrolysis by digestive enzymes, while rutin itself was not degraded. Thus, acylation of rutin with medium or long chain fatty acids may result in improved antioxidant abilities in more complex systems, including LDL-oxidation assays. Likely reasons may include improved lipophilic solubility and partitioning properties allowing for better accessibility to the actual site of oxidation. (C) 2010 Elsevier Ltd. All rights reserved.
AB - Practical limitations exist regarding the effectiveness of flavonoids as antioxidants in many food systems, possibly due to their poor solubility and miscibility in lipidic environments. Current strategies to improve these properties include enzymatically acylating flavonoids with lipophilic moieties. Herein, two derivatives of rutin (possessing C12:0 or C16:0 acyl groups) were assessed for their antioxidant properties, and compared with their parent compound, rutin and with butylated hydroxytoluene (BHT). While all compounds exhibited relatively strong radical scavenging abilities, modified rutin compounds exhibited decreased reducing power and metal chelating abilities as compared to rutin. Conversely, investigations on the oxidation of human low density lipoprotein (LDL) revealed that rutin laurate was most effective in inhibiting oxidation by prolonging LDL lag time for an in vitro system. With regards to in vivo considerations, a pre-treatment step confirmed that the ester bond linking rutin and acyl moieties was most susceptible to hydrolysis by digestive enzymes, while rutin itself was not degraded. Thus, acylation of rutin with medium or long chain fatty acids may result in improved antioxidant abilities in more complex systems, including LDL-oxidation assays. Likely reasons may include improved lipophilic solubility and partitioning properties allowing for better accessibility to the actual site of oxidation. (C) 2010 Elsevier Ltd. All rights reserved.
U2 - 10.1016/j.foodchem.2010.04.009
DO - 10.1016/j.foodchem.2010.04.009
M3 - Journal article
SN - 0308-8146
VL - 123
SP - 221
EP - 230
JO - Food Chemistry
JF - Food Chemistry
IS - 2
ER -