Novel bromotyrosine alkaloids: Inhibitors of mycothiol S-conjugate amidase

被引:70
作者
Nicholas, GM
Newton, GL
Fahey, RC
Bewley, CA [1 ]
机构
[1] NIDDK, Bioorgan Chem Lab, NIH, Bethesda, MD 20892 USA
[2] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
关键词
D O I
10.1021/ol015845+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The novel alkaloids 1 and 4 were isolated from an Australian non-verongid sponge, Oceanapia sp, Compound 1 contains an unprecedented imidazolyl-quinolinone substructure attached to a bromotyrosine-derived spiro isoxazoline. Three other known alkaloids were isolated in addition to 1 and 4 and together represent the first examples of inhibitors of a new mycobacterial enzyme mycothiol S-conjugate amidase (MCA).
引用
收藏
页码:1543 / 1545
页数:3
相关论文
共 13 条
[1]   Bromotyrosine alkaloids from the sponge Pseudoceratina verrucosa [J].
Benharref, A ;
Pais, M ;
Debitus, C .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (02) :177-180
[2]   Aciculitins A-C: Cytotoxic and antifungal cyclic peptides from the lithistid sponge Aciculites orientalis [J].
Bewley, CA ;
He, HY ;
Williams, DH ;
Faulkner, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4314-4321
[3]   THE ZOOCHROME OF THE SPONGE VERONGIA-AEROPHOBA (URANIDINE) [J].
CIMINO, G ;
DEROSA, S ;
DESTEFANO, S ;
SPINELLA, A ;
SODANO, G .
TETRAHEDRON LETTERS, 1984, 25 (27) :2925-2928
[4]  
KOBAYASHI J, 1995, CHEM PHARM BULL, V43, P403
[5]   IANTHELLINE, A NEW DERIVATIVE OF 3,5-DIBROMO-TYROSINE ISOLATED FROM THE SPONGE IANTHELLA-ARDIS FROM THE BAHAMAS [J].
LITAUDON, M ;
GUYOT, M .
TETRAHEDRON LETTERS, 1986, 27 (37) :4455-4456
[6]  
NEWTON GL, 1995, EUR J BIOCHEM, V230, P821
[7]   Distribution of thiols in microorganisms: Mycothiol is a major thiol in most actinomycetes [J].
Newton, GL ;
Arnold, K ;
Price, MS ;
Sherrill, C ;
Delcardayre, SB ;
Aharonowitz, Y ;
Cohen, G ;
Davies, J ;
Fahey, RC ;
Davis, C .
JOURNAL OF BACTERIOLOGY, 1996, 178 (07) :1990-1995
[8]   N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-α-D-glucopyranoside deacetylase (MshB) is a key enzyme in mycothiol biosynthesis [J].
Newton, GL ;
Av-Gay, Y ;
Fahey, RC .
JOURNAL OF BACTERIOLOGY, 2000, 182 (24) :6958-6963
[9]   Characterization of Mycobacterium smegmatis mutants defective in 1-D-myo-inosityl-2-amino-2-deoxy-α-D-glucopyranoside and mycothiol biosynthesis [J].
Newton, GL ;
Unson, MD ;
Anderberg, SJ ;
Aguilera, JA ;
Oh, NN ;
delCardayre, SB ;
Av-Gay, Y ;
Fahey, RC .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1999, 255 (02) :239-244
[10]   A novel mycothiol-dependent detoxification pathway in mycobacteria involving mycothiol S-conjugate amidase [J].
Newton, GL ;
Av-Gay, Y ;
Fahey, RC .
BIOCHEMISTRY, 2000, 39 (35) :10739-10746