Formation of thomasidioic acid from dehydrosinapinic acid dilactone under neutral conditions, and a remaining inhibitory activity against peroxynitrite-mediated protein nitration

被引:12
作者
Niwa, T
Doi, U
Osawa, T
机构
[1] San Ei Sucrochem Co Ltd, Dept Res & Dev, Aichi 4788503, Japan
[2] Nagoya Univ, Grad Sch Bioagr Sci, Lab Food & Biodynam, Nagoya, Aichi 4648601, Japan
关键词
D O I
10.1016/S0960-894X(02)00059-8
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Dehydrosinapinic acid dilactone (1) was converted to thomasidioic acid (3) and (E,E)-2,3-bis(3,5-dimethoxy-4-hydroxybenzylidene)succinic acid (4) via an a,p-unsaturated gamma-lactone type dimer (2) in phosphate buffer (pH 7.4). A study of the reaction mechanism was accomplished by observing the reaction of methyl ester of 2. The lignans (3, 4) were also prevented the peroxynitrite-mediated protein nitration. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:963 / 965
页数:3
相关论文
共 27 条
[1]  
AHMED R, 1976, TETRAHEDRON, V32, P1339, DOI 10.1016/0040-4020(76)85006-5
[2]  
ANJANEYULU ASR, 1994, INDIAN J CHEM B, V33, P839
[3]   NEW SYNTHETIC ROUTE TO BUTANOLIDE LIGNANS BY A RUTHENIUM COMPLEX CATALYZED HYDROGENATION OF THE CORRESPONDING STOBBES FULGENIC ACIDS [J].
BAMBAGIOTTIALBERTI, M ;
CORAN, SA ;
VINCIERI, FF ;
MULINACCI, N ;
PIERACCINI, GML .
HETEROCYCLES, 1988, 27 (09) :2185-2196
[4]   GADAIN, A LIGNAN FROM JATROPHA-GOSSYPIFOLIA [J].
BANERJI, J ;
DAS, B ;
CHATTERJEE, A ;
SHOOLERY, JN .
PHYTOCHEMISTRY, 1984, 23 (10) :2323-2327
[5]   INHIBITION OF RAT-LIVER MEVALONATE PYROPHOSPHATE DECARBOXYLASE AND MEVALONATE PHOSPHATE KINASE BY PHENYL AND PHENOLIC-COMPOUNDS [J].
BHAT, CS ;
RAMASARMA, T .
BIOCHEMICAL JOURNAL, 1979, 181 (01) :143-151
[6]   SOME STEREOCHEMICAL STUDIES OF LIGNANS [J].
BIRCH, AJ ;
MILLIGAN, B ;
SMITH, E ;
SPEAKE, RN .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (DEC) :4471-4476
[7]   THE CONSTITUENTS OF NATURAL PHENOLIC RESINS .23. A SYNTHESIS OF GALGRAVIN [J].
BLEARS, JG ;
HAWORTH, RD .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (MAY) :1985-1987
[8]   CONSTITUENTS OF PHEBALIUM-NUDUM .3. STRUCTURES OF PHEBALIN AND PHEBALARIN [J].
BROWN, KL ;
BURFITT, AIR ;
CAMBIE, RC ;
HALL, D ;
MATHAI, KP .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (06) :1327-1337
[9]   The constititents of natural phenolic resins. Part XIX. The oxidation of ferulic acid. [J].
Cartwright, NJ ;
Haworth, RD .
JOURNAL OF THE CHEMICAL SOCIETY, 1944, :535-537
[10]   Studies on phytochemicals part 29 -: Gossypidien, a lignan from stems of Jatropha gossypifollia [J].
Das, B ;
Anjani, G .
PHYTOCHEMISTRY, 1999, 51 (01) :115-117