Abstract
A series of methyl-pendanted resorcinarene derivatives have been synthesised and evaluated for radical scavenging potential by using a colorimetric DPPH• assay to reveal their utility as potent radical scavengers. An evaluation of the efficiencies in relation to the number of DPPH• molecules reduced by one molecule of antioxidant establishes that resorcinarene can reduce approximately eight DPPH• molecules at a fairly lower stoichiometric concentration. This behaviour is compared to that of well known radical scavengers (α-tocopherol, BHT and resorcinol) frequently used as reference compounds in scientific evaluations.
References
1.
Timmerman P.
,
Verboom W.
, and
Reinhoudt D.N.
, Tetrahedron , 1996 , 52 , 2663 .
2.
Rhlalou T.
,
Ferhat M.
,
Frouji M.A.
,
Langevin D.
,
Métayer M.
, and
Verchère J.F.
, J. Membr. Sci. , 2000 , 168 , 63 .
3.
Husaru L.
,
Schulze R.
,
Steiner G.
,
Wolff T.
,
Habicher W.D.
, and
Salzer R.
, Anal. Bioanal. Chem. , 2005 , 382 , 1882 .
4.
Nikolelis D.P.
,
Petropoulou S.S.E.
,
Pergel E.
, and
Toth K.
, Electroanalysis , 2002 , 14 , 783 .
5.
Demura M.
,
Yoshida T.
,
Hirokawa T.
,
Kumaki Y.
,
Aizawa T.
,
Nitta K.
,
Bitter I.
, and
Toth K.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 1367 .
6.
Hogg J.S.
,
Lohmann D.H.
, and
Russell K.E.
, Can. J. Chem. , 1961 , 39 , 1588 .
7.
Ayscough P.B.
, and
Russell K.E.
, Can. J. Chem. , 1965 , 43 , 3039 .
8.
Schenk G.H.
, and
Brown D.J.
, Talanta , 1967 , 14 , 257 .
9.
Shahidi F.
,
Janitha P.K.
, and
Wanasundara P.D.
, Crit. Rev. Food Sci. Nutr. , 1992 , 32 , 67 .
10.
Cuvelier M.E.
,
Richard H.
, and
Berset C.
, Biosci. Biotechnol. Biochem. , 1992 , 56 , 324 .
11.
Hotta H.
,
Nagano S.
,
Ueda M.
,
Tsujino Y.
,
Koyama J.
, and
Osakai T.
, Biochim. Biophys. Acta , 2002 , 1572 , 123 .
12.
Villano D.
,
Fernández-Pachón M.S.
,
Moyá M.L.
,
Troncoso A.M.
, and
Garcia-Parrilla M.C.
, Talanta , 2007 , 71 , 230 .
13.
Consoli G.M.L.
,
Galante E.
,
Daquino C.
,
Granata G.
,
Cunsolo F.
, and
Geraci C.
, Tetrahedron Lett. , 2006 , 47 , 6611 .
14.
Brand-Williams W.
,
Cuvelier M. E.
, and
Berset C.
, Lebensm.-Wiss. Technol. , 1995 , 28 , 25 .
15.
Bondet V.
,
Brand-Williams W.
, and
Berset C.
, Lebensm.-Wiss. Technol. , 1997 , 30 , 609 .
16.
Friaa O.
, and
Brault D.
, Org. Biomol. Chem. , 2006 , 4 , 2417 .
17.
Capozzi G.
,
Nativi C.
,
Sarri P.
,
Nostro P.L.
, and
Menichetti S.
, Chem. Commun. , 2001 , 2001 , 551 .
18.
Foti M.C.
, and
Daquino C.
, Chem. Commun. , 2006 , 3252 .
19.
Blois M.S.
, Nature , 1958 , 181 , 1199 .
20.
Hoegberg A.G.S.
, J. Org. Chem. , 1980 , 45 , 4498 .
21.
Matsushita Y.I.
, and
Matsui T.
, Tetrahedron Lett. , 1993 , 34 , 7433 .
22.
Beyeh N.K.
,
Aumanen J.
,
Åhman A.
,
Luostarinen M.
,
Mansikkamäki H.
,
Nissinen M.
,
Korppi-Tommola J.
, and
Rissanen K.
, New J. Chem. , 2007 , 31 , 370 .
23.
Fransen J.R.
, and
Dutton P.J.
, Can. J. Chem. , 1995 , 73 , 2217 .
24.
Capellos C.
, and
Bielski B.H.J.
, Kinetic systems , Wiley-Interscience , New York , 1972 .
25.
Gülçin
, Toxicology , 2006 , 217 , 213 .
26.
Demchenko A.M.
,
Yanchenko V.O.
,
Smolskly O.S.
,
Aheyev V.O.
, and
Lozynskly M.O.
, Farmatsevtichnii Zhurnal (Kiev ), 2004 , 1 , 68 .