Crude peroxidase from onion solid waste as a tool for organic synthesis. Part III: synthesis of tetracyclic heterocycles (coumestans and benzofuroquinolinones)

被引：25

作者：

Angeleska, Simona ^{[1
]}

Kefalas, Panagiotis ^{[1
]}

Detsi, Anastasia ^{[2
]}

机构：

[1] Ctr Int Hautes Etud Agron Mediterraneennes, Mediterranean Agron Inst Chania, Dept Food Qual & Chem Nat Prod, Khania 73100, Crete, Greece

[2] Natl Tech Univ Athens, Sch Chem Engn, Dept Chem Sci, Lab Organ Chem,Heroon Polytech 9, Athens 15780, Greece

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 19期

关键词：

Crude onion peroxidase extract; Coumestans; Benzofuroquinolinones; PHENOLIC-COMPOUNDS; BIOCATALYTIC PROPERTIES; DERIVATIVES; IDENTIFICATION; OXIDATION; CELLS;

D O I：

10.1016/j.tetlet.2013.02.081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the present study the biocatalytic activity of a crude onion peroxidase extract on the reaction between catechol and heterocyclic 1,3-dicarbonyl compounds is investigated. The crude enzyme preparation promotes effectively the reaction between catechol and 4-hydroxycoumarin, 4-hydroxy-1-methyl-2-quinolinone and 2,4-quinolinediol to afford the corresponding coumestans and benzofuroquinolinones in satisfactory yields. The products of the reaction are fully characterized spectroscopically and are found to possess potent antioxidant activity as evaluated by 2,2-diphenyl-1-piciylhydrazyl (DPPH), ferric reducing antioxidant power (FRAP), and luminol-induced chemiluminescence assays. (C) 2013 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2325 / 2328

页数：4

相关论文

共 26 条

[1] Effect of principal polyphenolic components in relation to antioxidant characteristics of aged red wines [J].

Arnous, A ;

Makris, DP ;

Kefalas, P .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (12) :5736-5742

[2] Removal of olive mill waste water phenolics using a crude peroxidase extract from onion by-products [J].

Barakat, Nada ;

Makris, Dimitris P. ;

Kefalas, Panagiotis ;

Psillakis, Elefteria .

ENVIRONMENTAL CHEMISTRY LETTERS, 2010, 8 (03) :271-275

[3]

Benzie IFF, 1999, METHOD ENZYMOL, V299, P15

[4] Phenolic Compounds from Pueraria lobata Protect PC12 Cells against Aβ-induced Toxicity [J].

Choi, Yun-hyeok ;

Hong, Seong Su ;

Shin, Yu Su ;

Hwang, Bang Yeon ;

Park, So-Young ;

Lee, Dongho .

ARCHIVES OF PHARMACAL RESEARCH, 2010, 33 (10) :1651-1654

[5] Synthesis and preliminary pharmacological evaluation of coumestans with different patterns of oxygenation [J].

da Silva, AJM ;

Melo, PA ;

Silva, NMV ;

Brito, FV ;

Buarque, CD ;

de Souza, DV ;

Rodrigues, VP ;

Poças, ESC ;

Noël, F ;

Albuquerque, EX ;

Costa, PRR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (03) :283-286

[6] Peroxidase-Active Cell Free Extract from Onion Solid Wastes: Biocatalytic Properties and Putative Pathway of Ferulic Acid Oxidation [J].

El Agha, Ayman ;

Makris, Dimitris P. ;

Kefalas, Panagiotis .

JOURNAL OF BIOSCIENCE AND BIOENGINEERING, 2008, 106 (03) :279-285

[7] Mechanistic study of electrochemical oxidation of catechols in the presence of 4-hydroxy-1-methyl-2(1H)-quinolone -: Application to the electrochemical synthesis [J].

Fakhari, AR ;

Nematollahi, D ;

Moghaddam, AB .

ELECTROCHIMICA ACTA, 2005, 50 (27) :5322-5328

[8] Identification of phenolic compounds in isolated vacuoles of the medicinal plant Catharanthus roseus and their interaction with vacuolar class III peroxidase: an H2O2 affair? [J].

Ferreres, Federico ;

Figueiredo, Raquel ;

Bettencourt, Sara ;

Carqueijeiro, Ines ;

Oliveira, Juliana ;

Gil-Izquierdo, Angel ;

Pereira, David M. ;

Valentao, Patricia ;

Andrade, Paula B. ;

Duarte, Patricia ;

Ros Barcelo, Alfonso ;

Sottomayor, Mariana .

JOURNAL OF EXPERIMENTAL BOTANY, 2011, 62 (08) :2841-2854

[9] Identification of a class of small molecule inhibitors of the sirtuin family of NAD-dependent deacetylases by phenotypic screening [J].

Grozinger, CM ;

Chao, ED ;

Blackwell, HE ;

Moazed, D ;

Schreiber, SL .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (42) :38837-38843

[10] The Laccase-Catalyzed Domino Reaction between Catechols and Heterocyclic 1,3-Dicarbonyls and the Unambiguous Structure Elucidation of the Products by NMR Spectroscopy and X-ray Crystal Structure Analysis [J].

Hajdok, Szilvia ;

Conrad, Ruergen ;

Leutbecher, Heiko ;

Strobel, Sabine ;

Schleid, Thomas ;

Beifuss, Uwe .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7230-7237