Antimicrobial, Anti-Inflammatory and Antioxidant Activities of Polyoxygenated Chalcones

被引:38
作者
Vasquez-Martinez, Yesseny A. [1 ]
Osorio, Mauricio E. [2 ]
San Martin, Diego A. [2 ]
Carvajal, Marcela A. [3 ]
Vergara, Alejandra P. [3 ]
Sanchez, Elizabeth [3 ]
Raimondi, Marcela [4 ]
Zacchino, Susana A. [4 ]
Mascayano, Carolina [5 ]
Torrent, Claudia [5 ]
Cabezas, Francisco [5 ]
Mejias, Sophia [6 ]
Montoya, Margarita [6 ]
Cortez-San Martin, Marcelo [6 ]
机构
[1] Univ Santiago Chile, Fac Ciencias Med, Programa Ctr Invest Biomed Aplicadas, Santiago 9170022, Chile
[2] Univ Tecn Federico Santa Maria, Dept Quim, Lab Prod Nat, Valparaiso 2390123, Chile
[3] Univ Tecn Federico Santa Maria, Ctr Biotecnol CB DAL, Valparaiso 2390136, Chile
[4] Univ Nacl Rosario, Farmacognosia, Fac Ciencias Bioquim & Farmaceut, Suipacha 531, RA-2000 Rosario, Santa Fe, Argentina
[5] Univ Santiago Chile, Fac Quim & Biol, Dept Ciencias Ambiente, Santiago 9170022, Chile
[6] Univ Santiago Chile, Dept Biol, Fac Quim & Biol, Santiago 9170022, Chile
关键词
antioxidant activity; polyoxygenated chalcones; human 5-lipoxygenase inhibitors; antibacterial; antifungal; GROWTH-INHIBITORY PROPERTIES; IN-VITRO; PHYTOPHTHORA-CINNAMOMI; ANTIBACTERIAL ACTIVITY; BIOLOGICAL-ACTIVITIES; SYNTHETIC CHALCONES; POTENT INHIBITORS; BOTRYTIS-CINEREA; EFFICIENT METHOD; SOLVENT-FREE;
D O I
10.21577/0103-5053.20180177
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
It was synthesized nine polyoxygenated chalcones with a potential and safe use as antioxidant, antimicrobial and anti-inflammatory therapies. Chalcones obtained by Claisen-Schmidt condensation were studied as antioxidant, inhibitors of human 5-lipoxygenase, antifungal, antibacterial and antibiotic resistance modifiers. Two chalcones with catecholic moieties were able to strongly decrease the minimum inhibitory concentration (MIC) of methicillin against methicillin-resistant Staphylococcus aureus, increase the antiradical activity and significantly inhibit the human 5-lipoxygenase. Only one of these chalcones was active synergistically with methicillin. Chalcones with methoxyl substituents at different positions displayed the best activities against Cryptococcus neoformans. Only one chalcone showed good activity against the plant pathogenic bacteria Pseudomonas syringae whose half maximal inhibitory concentration (IC50) value (2.5 mu g mL(-1)) was similar to that observed with the antibiotic streptomycin (2.9 mu g mL(-1)). These simple chalcones have safe potential uses in antioxidant, antimicrobial and anti-inflammatory therapies.
引用
收藏
页码:286 / 304
页数:19
相关论文
共 93 条
[51]   Novel Chalcone Derivatives as Potent Nrf2 Activators in Mice and Human Lung Epithelial Cells [J].
Kumar, Vineet ;
Kumar, Sarvesh ;
Hassan, Mohammad ;
Wu, Hailong ;
Thimmulappa, Rajesh K. ;
Kumar, Amit ;
Sharma, Sunil K. ;
Parmar, Virinder S. ;
Biswal, Shyam ;
Malhotra, Sanjay V. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (12) :4147-4159
[52]   Improved synthesis of chalcones under ultrasound irradiation [J].
Li, JT ;
Yang, WZ ;
Wang, SX ;
Li, SH ;
Li, TS .
ULTRASONICS SONOCHEMISTRY, 2002, 9 (05) :237-239
[53]   In vitro antifungal evaluation and structure-activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall [J].
López, SN ;
Castelli, MV ;
Zacchino, SA ;
Domínguez, JN ;
Lobo, G ;
Charris-Charris, J ;
Cortés, JCG ;
Ribas, JC ;
Devia, C ;
Rodríguez, AM ;
Enriz, RD .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (08) :1999-2013
[54]  
Lucera Annalisa, 2012, Front Microbiol, V3, P287, DOI 10.3389/fmicb.2012.00287
[55]   Chalcone scaffolds as anti-infective agents: Structural and molecular target perspectives [J].
Mahapatra, Debarshi Kar ;
Bharti, Sanjay Kumar ;
Asati, Vivek .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 101 :496-524
[56]   Enzymatic Studies of Isoflavonoids as Selective and Potent Inhibitors of Human Leukocyte 5-Lipo-Oxygenase [J].
Mascayano, Carolina ;
Espinosa, Victoria ;
Sepulveda-Boza, Silvia ;
Hoobler, Eric K. ;
Perry, Steve ;
Diaz, Giovanni ;
Holman, Theodore R. .
CHEMICAL BIOLOGY & DRUG DESIGN, 2015, 86 (01) :894-901
[57]   In Vitro Study of Isoflavones and Isoflavans as Potent Inhibitors of Human 12-and 15-Lipoxygenases [J].
Mascayano, Carolina ;
Espinosa, Victoria ;
Sepulveda-Boza, Silvia ;
Hoobler, Eric K. ;
Perry, Steve .
CHEMICAL BIOLOGY & DRUG DESIGN, 2013, 82 (03) :317-325
[58]   Antibiotic use in plant agriculture [J].
McManus, PS ;
Stockwell, VO ;
Sundin, GW ;
Jones, AL .
ANNUAL REVIEW OF PHYTOPATHOLOGY, 2002, 40 :443-+
[59]   Antifungal constituents of the essential oil fraction of Artemisia dracunculus L. var. dracunculus [J].
Meepagala, KM ;
Sturtz, G ;
Wedge, DE .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (24) :6989-6992
[60]  
Mishra P. K., 2007, Mycobiology, V35, P72, DOI 10.4489/MYCO.2007.35.2.072