Synthesis of a novel ester of hydroxytyrosol and α-lipoic acid exhibiting an antiproliferative effect on human colon cancer HT-29 cells

被引:66
作者
Bernini, Roberta [1 ]
Crisante, Fernanda [1 ]
Merendino, Nicolo [2 ]
Molinari, Romina [2 ]
Soldatelli, Maria Chiara [1 ]
Velotti, Francesca [2 ]
机构
[1] Univ Tuscia, Dipartimento Agrobiol & Agrochim, I-01100 Viterbo, Italy
[2] Univ Tuscia, Dipartimento Ecol & Sviluppo Econ Sostenibile, I-01100 Viterbo, Italy
关键词
Hydroxytyrosol; alpha-Lipoic acid; Antiproliferative activity; Human colon cancer HT-29 cell line; 2-Iodoxybenzoic acid (IBX); VIRGIN OLIVE OIL; LOW-DENSITY-LIPOPROTEIN; CONVENIENT SYNTHESIS; PHENOLIC-COMPOUNDS; ANTIOXIDANT; OXIDATION; PROLIFERATION; DERIVATIVES; INHIBITION; CHEMISTRY;
D O I
10.1016/j.ejmech.2010.10.028
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A novel ester of hydroxytyrosol and alpha-lipoic acid was synthesized in satisfactory yield by original and simple procedures and evaluated about its antiproliferative activity on the human colorectal adenocarcinoma HT-29 cell line. The compound exhibited a cell growth inhibitory activity significantly more potent than the corresponding parent natural compounds, very likely due to the induction of cell cycle arrest in the G2/M phase. These data suggest that the novel ester might exert a more effective antitumour activity than hydroxytyrosol and alpha-lipoic acid. (C) 2010 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:439 / 446
页数:8
相关论文
共 60 条
[1]   Toward a high yield recovery of antioxidants and purified hydroxytyrosol from olive mill wastewaters [J].
Allouche, N ;
Fki, I ;
Sayadi, S .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (02) :267-273
[2]   GC-RIS EVALUATION OF PHENOLIC-COMPOUNDS IN VIRGIN OLIVE OIL [J].
ANGEROSA, F ;
DALESSANDRO, N ;
KONSTANTINOU, P ;
DIGIACINTO, L .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1995, 43 (07) :1802-1807
[3]  
[Anonymous], ITAL J FOOD SCI
[4]   Effect of hydroxytyrosol found in extra virgin olive oil on oxidative DNA damage and oil low-density lipoprotein oxidation [J].
Aruoma, OI ;
Deiana, M ;
Jenner, A ;
Halliwell, B ;
Kaur, H ;
Banni, S ;
Corongiu, FP ;
Dessí, MA ;
Aeschbach, R .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1998, 46 (12) :5181-5187
[5]   Cytochrome P450s in flavonoid metabolism [J].
Ayabe S.-I. ;
Akashi T. .
Phytochemistry Reviews, 2006, 5 (2-3) :271-282
[6]   Phenolic compounds in plants and agri-industrial by-products: Antioxidant activity, occurrence, and potential uses [J].
Balasundram, Nagendran ;
Sundram, Kalyana ;
Samman, Samir .
FOOD CHEMISTRY, 2006, 99 (01) :191-203
[7]   COMPARATIVE OXIDATION OF PHENOLS WITH BENZENESELENINIC ANHYDRIDE AND WITH BENZENESELENINIC ACID [J].
BARTON, DHR ;
FINET, JP ;
THOMAS, M .
TETRAHEDRON, 1988, 44 (20) :6397-6406
[8]  
Bemini R., 2007, It. Pat., Patent No. [MI2007A001110, 2007001110]
[9]  
Bernini R., 2008, Patent No. [2008110908, WO 2008110908 A1]
[10]   2-arylhydroxytyrosol derivatives via Suzuki-Miyaura cross-coupling [J].
Bernini, Roberta ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Filisti, Eleonora .
ORGANIC LETTERS, 2008, 10 (16) :3457-3460