Oxidation of porphyrinogens by horseradish peroxidase and formation of a green pyrrole pigment

被引:14
作者
Jacobs, JM
Jacobs, NJ
Kuhn, CB
Gorman, N
Dayan, FE
Duke, SO
Sinclair, JF
机构
[1] DARTMOUTH COLL SCH MED,DEPT MICROBIOL,HANOVER,NH 03755
[2] DARTMOUTH COLL SCH MED,DEPT BIOCHEM & PHARMACOL TOXICOL,HANOVER,NH 03755
[3] VET ADM MED CTR,WHITE RIVER JCT,VT 05009
[4] USDA ARS,SO WEED SCI LAB,STONEVILLE,MS 38776
关键词
D O I
10.1006/bbrc.1996.1488
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
When humans or plants are exposed to certain chemicals which interfere with heme biosynthetic enzymes, porphyrinogen intermediates accumulate and are oxidized to cytotoxic porphyrins. Here rye have investigated the role of peroxidases in porphyrinogen oxidation. Horseradish peroxidase (HRP) rapidly oxidizes uroporphyrinogen to uroporphyrin and this is inhibited by ascorbic acid. HRP also oxidizes deuteroporphyrinogen (a synthetic porphyrin similar to protoporphyrinogen), but the yield of porphyrin is lower than with uroporphyrinogen as substrate. This low yield is in part due to a rapid, HRP-dependent conversion of deuteroporphyrin (but not uroporphyrin) to a green compound with spectral characteristics of a chlorin with a large peak at 638 nm. This reaction requires addition of a sulfhydryl reductant such as glutathione and is inhibited by ascorbic acid. These findings suggest that cellular peroxidases and ascorbic acid levels may play a role in modifying the phototoxic tetrapyrroles which accumulate in plants and humans after certain environmental exposures. (C) 1996 Academic Press, Inc.
引用
收藏
页码:195 / 199
页数:5
相关论文
共 14 条
[1]   MESO-REACTIVITY OF PORPHYRINS AND RELATED COMPOUNDS .4. INTRODUCTION OF OXYGEN FUNCTIONS [J].
BONNETT, R ;
DIMSDALE, MJ ;
STEPHENSON, GF .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04) :564-+
[2]  
DEMATTEIS F, 1988, BIOCHEM J, V250, P191
[3]  
JACOBS JM, 1994, ACS SYM SER, V559, P105
[4]   PORPHYRIN STABILITY IN PLANT SUPERNATANT FRACTIONS - IMPLICATIONS FOR THE ACTION OF PORPHYRINOGENIC HERBICIDES [J].
JACOBS, JM ;
WEHNER, JM ;
JACOBS, NJ .
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 1994, 50 (01) :23-30
[5]   OXIDATION OF UROPORPHYRINOGEN BY METHYLCHOLANTHRENE-INDUCED CYTOCHROME-P-450 - ESSENTIAL ROLE OF CYTOCHROME-P-450D [J].
JACOBS, JM ;
SINCLAIR, PR ;
BEMENT, WJ ;
LAMBRECHT, RW ;
SINCLAIR, JF ;
GOLDSTEIN, JA .
BIOCHEMICAL JOURNAL, 1989, 258 (01) :247-253
[6]   ASSAY FOR ENZYMATIC PROTOPORPHYRINOGEN OXIDATION, A LATE STEP IN HEME-SYNTHESIS [J].
JACOBS, NJ ;
JACOBS, JM .
ENZYME, 1982, 28 (2-3) :206-217
[7]   OXYGENATED TETRAPYRROLES PRODUCED FROM PORPHYRINOGENS [J].
LIN, W ;
TIMKOVICH, R .
BIOORGANIC CHEMISTRY, 1994, 22 (01) :72-94
[8]   DISCOVERY AND SYNTHESIS OF LESS COMMON NATURAL HYDROPORPHYRINS [J].
MONTFORTS, FP ;
GERLACH, B ;
HOPER, F .
CHEMICAL REVIEWS, 1994, 94 (02) :327-347
[9]  
Scheer H., 1978, PORPHYRINS, V2, P45, DOI DOI 10.1016/B978-0-12-220102-8.50009-9
[10]   EVIDENCE FOR CYTOCHROME-P450-MEDIATED OXIDATION OF UROPORPHYRINOGEN BY CELL-FREE LIVER EXTRACTS FROM CHICK-EMBRYOS TREATED WITH 3-METHYLCHOLANTHRENE [J].
SINCLAIR, P ;
LAMBRECHT, R ;
SINCLAIR, J .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 146 (03) :1324-1329