Synthesis and radical scavenger properties of novel spirochromenes derived from steroid sapogenins

被引:15
作者
Ramos-Enriquez, Manuel A. [1 ]
Medina-Campos, Omar N. [1 ]
Pedraza-Chaverri, Jose [1 ]
Iglesias-Arteaga, Martin A. [1 ]
机构
[1] Univ Nacl Autonoma Mexico, Fac Quim, Mexico City 04510, DF, Mexico
关键词
Steroid sapogenins; Spirochromenes; Radical scavengers; Antioxidant activity; DPPH test; ANTIOXIDANT CAPACITY; OXIDATIVE STRESS; ALPHA-TOCOPHEROL; SIDE-CHAIN; BF3-CENTER-DOT-ET2O; ACID; CEPHALOSTATINS; PEROXIDATION; CHEMISTRY; PRODUCTS;
D O I
10.1016/j.steroids.2015.03.013
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Tandem aldol condensation between steroid sapogenins and hydroxylated benzaldehydes afforded steroidal spirochromenes. Compounds that bear a phenolic hydroxyl group at position C-6', obtained by a reaction with 2,5-dihydroxybenzaldehyde, showed approximately 80% of maximal radical scavenging activity in the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) assay at 288 nM. In contrast, the starting steroid sapogenins and the spirochromenes without a phenolic group in the side chain proved to be inactive. (C) 2015 Elsevier Inc. All rights reserved.
引用
收藏
页码:132 / 137
页数:6
相关论文
共 46 条
[1]   ANTIOXIDANT DETERMINATIONS BY THE USE OF A STABLE FREE RADICAL [J].
BLOIS, MS .
NATURE, 1958, 181 (4617) :1199-1200
[2]   The unexpected role of vitamin E (α-tocopherol) in the peroxidation of human low-density lipoprotein [J].
Bowry, VW ;
Ingold, KU .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (01) :27-34
[3]   Structural basis for antioxidant activity of trans-resveratrol:: Ab initio calculations and crystal and molecular structure [J].
Caruso, F ;
Tanski, J ;
Villegas-Estrada, A ;
Rossi, M .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (24) :7279-7285
[4]   Free radical scavenger and antioxidant capacity correlation of α-tocopherol and Trolox measured by three in vitro methodologies [J].
Castro, Inar A. ;
Rogero, Marcelo M. ;
Junqueira, Roberto M. ;
Carrapeiro, Mariana M. .
INTERNATIONAL JOURNAL OF FOOD SCIENCES AND NUTRITION, 2006, 57 (1-2) :75-82
[5]   High-throughput relative DPPH radical scavenging capacity assay [J].
Cheng, Zhihong ;
Moore, Jeffrey ;
Yu, Liangli .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (20) :7429-7436
[6]  
Cluter, 1991, BRASSINOSTEROIDS CHE
[7]  
Fieser L.F., 1959, STEROIDS
[8]   Mechanism of the OH Radical Scavenging Activity of Nordihydroguaiaretic Acid: A Combined Theoretical and Experimental Study [J].
Galano, Annia ;
Macias-Ruvalcaba, Norma A. ;
Medina Campos, Omar Noel ;
Pedraza-Chaverri, Jose .
JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (19) :6625-6635
[9]   Approaches towards the synthesis of cephalostatins, ritterazines and saponins from Ornithogalum saundersiae -: New natural products with cytostatic activity [J].
Gryszkiewicz-Wojtkielewicz, A ;
Jastrzebska, I ;
Morzycki, JW ;
Romanowska, DB .
CURRENT ORGANIC CHEMISTRY, 2003, 7 (12) :1257-1277
[10]  
Guzman-Beltran S, 2013, OXID MED CELL LONGEV