Synthesis and Antioxidant Activity of Phloretin Acetylferulic Acid Esters

doi:A

Abstract

Abstract: Three new compounds were firstly synthesized by ferulic acid and phloretin. The target compound was characterized by IR, 1H NMR, 13C NMR and HPLC-MS, respectively. Reducing power, DPPH and •OH radical scavenging assays were carried out to evaluate the antioxidant and free radical scavenging abilities of phloretin and its esters. The results showed that the antioxidant and free radical scavenging abilities of phloretin acetylferulic acid esters were stronger than that of phloretin.

Key words: phloretin, ferulic acid, esterification, antioxidant activity , synthesis

CLC Number:

O625.32

LI Cui-ping, YU Yan-ying, CAO Shu-wen. Synthesis and Antioxidant Activity of Phloretin Acetylferulic Acid Esters[J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2012, 23(3): 316-320.

References

1 Rezk BM,Haenen GR,vander Vijgh WJ,et al.The antioxidant activity of phloretin:the disclosure of a new antioxidant pharmacophore in flavonoids.Biochem Biophys Res Commun,2002,295:9-13.
2 Zhang K,Das NP.Inhibitory effects of natural plant polyphenols on rat liver glutathione S-transferases.Biochem Pharmacol,1994,47:2063-2068.
3 Lu XY(陆晓宇),Zeng YY(曾耀英),Ye YX(叶燕霞),et al.Anti-inflammatory and immunosuppressive effect of phloretin.Acta Pharm Sin(药学学报),2009,44(5):480-485.
4 Kim MS,Kwon JY,Kang NJ,et al.Phloretin induces apoptosis in H-Ras MCF10A human breast tumor cells through the activation of p53 via JNK and p38 mitogen-activated protein kinase signaling.Ann N Y Acad Sci,2009,1171:479-483.
5 Yang KC,Tsai CY,Wang YJ,et al.Apple polyphenol phloretin potentiates the anticancer actions of paclitaxel through induction of apoptosis in human hep G2 cells.Mol Carcinog,2009,48:420-431.
6 Kobori M,Iwashita K,Shinmoto H,et al.Phloretin-induced apoptosis in B16 melanoma 4A5 cells and HL60 human leukemia cells.Biosci Biotechnol Biochem,1999,63:719-725.
7 Yu YY(余燕影),Li XH(李先和),Cao SW(曹树稳).Synthesis of genistein acetylferulic acid esters.Nat Prod Res Dev(天然产物研究与开发),2009,21:194-198.
8 Miller JA,Neuzil EF,Dong TW(董庭威).translation Mod-ern Experimental Organic Chemistry(现代有机化学实验).Shanghai Trans Pub,1987.152-157.
9 Yanosuke I,Koichi T,Hiroyuki K.Acyl cinnamic acid derivatives.JP:12892,1965-07-24.
10 Hosoda A,Nomura E,Mizuno K,et al.Preparation of a(±)-1,6-di-O-feruloyl-myo-inositol drivative:an efficientmethod for introduction of ferulic acid to1,6-vicinalhydroxylgroups of myoinosito.J Org Chem,2001,66:7199-7201.
11 Li YH,Jiang B,Zhang T,et al.Antioxidant and free radical-scavenging activities of chickpea protein hydrolysate(CPH).Food Chem,2008,106:444-450.
12 ee YL,Yang JH,Mau JL.Antioxidant properties of water extracts from Monascus fermented soybeans.Food Chem,2008,106:1127-1137.
13 Yu YY(余燕影),Zhang LH(章丽华),Cao SW(曹树稳).Investigation on free radical scavenging activity of flavonoid extracts from Millettia nitida Benth var. hirsutissima Z.Wei.Nat Prod Res Dev(天然产物研究与开发),2007,19(5):741-744.

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