Document Detail

Morphine metabolism in the opium poppy and its possible physiological function. Biochemical characterization of the morphine metabolite, bismorphine.
MedLine Citation:
PMID:  11498543     Owner:  NLM     Status:  MEDLINE    
We identified a novel metabolic system of morphine in the opium poppy (Papaver somniferum L.). In response to stress, morphine is quickly metabolized to bismorphine consisting of two morphine units, followed by accumulation in the cell wall. This bismorphine binds predominantly to pectins, which possess high galacturonic acid residue contents, through ionical bonds. Our newly developed method using artificial polysaccharides demonstrated that bismorphine bridges are formed between the two amino groups of bismorphine and the carboxyl groups of galacturonic acid residues, resulting in cross-linking of galacturonic acid-containing polysaccharides to each other. The ability of bismorphine to cross-link pectins is much higher than that of Ca2+, which also acts as a cross-linker of these polysaccharides. Furthermore, we confirmed that cross-linking of pectins through bismorphine bridges leads to resistance against hydrolysis by pectinases. These results indicated that production of bismorphine is a defense response of the opium poppy. Bismorphine formation is catalyzed by anionic peroxidase that pre-exists in the capsules and leaves of opium poppies. The constitutive presence of morphine, together with bismorphine-forming peroxidase, enables the opium poppy to rapidly induce the defense system.
S Morimoto; K Suemori; J Moriwaki; F Taura; H Tanaka; M Aso; M Tanaka; H Suemune; Y Shimohigashi; Y Shoyama
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Publication Detail:
Type:  Journal Article     Date:  2001-08-09
Journal Detail:
Title:  The Journal of biological chemistry     Volume:  276     ISSN:  0021-9258     ISO Abbreviation:  J. Biol. Chem.     Publication Date:  2001 Oct 
Date Detail:
Created Date:  2001-10-08     Completed Date:  2001-12-04     Revised Date:  2004-11-17    
Medline Journal Info:
Nlm Unique ID:  2985121R     Medline TA:  J Biol Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  38179-84     Citation Subset:  IM    
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, 812-8582, Japan.
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MeSH Terms
Carbohydrate Sequence
Magnetic Resonance Spectroscopy
Molecular Sequence Data
Morphine / chemistry,  metabolism*
Morphine Derivatives
Papaver / metabolism*
Plants, Medicinal*
Polysaccharides / chemistry
Reg. No./Substance:
0/Morphine Derivatives; 0/Polysaccharides; 0/bismorphine A; 57-27-2/Morphine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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