ON THE BROMINATION OF HYPERICIN - THE GYMNOCHROME CHROMOPHORES

被引:29
作者
FALK, H
SCHMITZBERGER, W
机构
[1] Institut für Chemie, Johannes Kepler Universität Linz, Linz
来源
MONATSHEFTE FUR CHEMIE | 1993年 / 124卷 / 01期
关键词
BROMO-HYPERICINES; GYMNOCHROMES; H-1-NMR; C-13-NMR; UV-VIS; PK(A) VALUES; FLUORESCENCE;
D O I
10.1007/BF00808512
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Stepwise electrophilic bromination of hypericin in pyridine as the solvent yields regioselectively 2,5-dibromohypericin, 2,5,9-tribromohypericin, and 2,5,9,12-tetrabromohypericin. The compounds were characterized by means of NMR-, UV-Vis-, and fluorescence-spectra, and pK(a) and pK(a)* measurements. These properties were compared with those of hypericin on the one hand and of the recently isolated gymnochromes on the other hand.
引用
收藏
页码:77 / 81
页数:5
相关论文
共 11 条
[1]  
BARLTROP JA, 1975, EXCITED STATES ORGAN, P82
[2]   THE GYMNOCHROMES - NOVEL MARINE BROMINATED PHENANTHROPERYLENEQUINONE PIGMENTS FROM THE STALKED CRINOID GYMNOCRINUS-RICHERI [J].
DERICCARDIS, F ;
IORIZZI, M ;
MINALE, L ;
RICCIO, R ;
DEFORGES, BR ;
DEBITUS, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6781-6787
[3]   DEPROTONATION AND PROTONATION OF HYDROXYPHENANTHROPERYLENES [J].
FALK, H ;
MEYER, J ;
OBERREITER, M .
MONATSHEFTE FUR CHEMIE, 1992, 123 (03) :277-284
[4]   ON THE NATURE OF SOLUBLE HYPERICIN IN HYPERICUM SPECIES [J].
FALK, H ;
SCHMITZBERGER, W .
MONATSHEFTE FUR CHEMIE, 1992, 123 (8-9) :731-739
[5]   A SYNTHESIS OF EMODIN ANTHRONE [J].
FALK, H ;
SCHOPPEL, G .
MONATSHEFTE FUR CHEMIE, 1991, 122 (8-9) :739-744
[6]  
Falk H, UNPUB
[7]  
FALK H, 1992, IN PRESS MONATSH CHE
[8]  
MAZUR Y, 1992, Patent No. 2029993
[9]   MOLECULAR GENETIC-ANALYSIS REVEALS A PUTATIVE BIFUNCTIONAL POLYKETIDE CYCLASE DEHYDRASE GENE FROM STREPTOMYCES-COELICOLOR AND STREPTOMYCES-VIOLACEORUBER, AND A CYCLASE O-METHYLTRANSFERASE FROM STREPTOMYCES-GLAUCESCENS [J].
SHERMAN, DH ;
BIBB, MJ ;
SIMPSON, TJ ;
JOHNSON, D ;
MALPARTIDA, F ;
FERNANDEZMORENO, M ;
MARTINEZ, E ;
HUTCHINSON, CR ;
HOPWOOD, DA .
TETRAHEDRON, 1991, 47 (31) :6029-6043
[10]  
Thomson R.H., 1987, NATURALLY OCCURRING