Synthesis and radical scavenging of novel magnolol derivatives.
We have investigated the developdment of potential antioxidants based on magnolol, a naturally occurring biphenolic obtained from the bark of Magnolia officinalis. A series of aminomethylated derivatives of magnolol were synthesized under the aromatic Mannich reaction. In-vitro testing for diphenyl-p-picrylhydrazyl (DPPH) scavenging and chemiluminescence assays in whole cell models revealed that the pyrrolidyl-containing magnolols (2b (5,5'-diallyl-3-(pyrrolidin-1-ylmethyl)-biphenyl-2,2'-diol), 3a (5,5'-diallyl-3,3'-bis-(pyrrolidin-1-ylmethyl)-biphenyl-2,2'-diol) and 4c (5,5'-diallyl-3-(morphorin-4-ylmethyl)-3'-(pyrrolidin-1-ylmethyl)-biphenyl-2,2'-diol)) displayed promising free radical scavenging effects as compared with magnolol. The results from compound 4c indicated that the naturally occurring component was suitable to be a lead compound toward promising antioxidants.
Wang
Yvonne
Y
School of Pharmacy, National Defense Medical Center, 161 Minchuan East Road, Section 6, Taipei 114, Taiwan, Republic of China.
Li
Chi-Yuan
CY
Lin
I-Hshin
IH
Lee
An-Rong
AR
Hu
Ming-Kuan
MK
D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry; D006834:Hydrazines / Q000737:chemistry*; D017705:Lignans; D008163:Luminescent Measurements; D031566:Magnolia / Q000737:chemistry; D010851:Picrates; D024301:Plant Bark / Q000737:chemistry; D010938:Plant Oils / Q000737:chemistry
D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D006834:Hydrazines; D017705:Lignans; D010851:Picrates; D010938:Plant Oils; C005498:magnolol; C004931:1,1-diphenyl-2-picrylhydrazyl