Morphine metabolism in the opium poppy and its possible physiological function. Biochemical characterization of the morphine metabolite, bismorphine

Satoshi Morimoto, Kazunari Suemori, Jun Moriwaki, Futoshi Taura, Hiroyuki Tanaka, Mariko Aso, Masakazu Tanaka, Hiroshi Suemune, Yasuyuki Shimohigashi, Yukihiro Shoyama

Research output: Contribution to journalArticle

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Abstract

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.

Original languageEnglish
Pages (from-to)38179-38184
Number of pages6
JournalJournal of Biological Chemistry
Volume276
Issue number41
DOIs
Publication statusPublished - Oct 12 2001

Fingerprint

Papaver
Opium
Pectins
Metabolites
Metabolism
Morphine
Polysaccharides
Peroxidase
Capsules
Hydrolysis
Cell Wall
Cells
galacturonic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Cell Biology

Cite this

Morphine metabolism in the opium poppy and its possible physiological function. Biochemical characterization of the morphine metabolite, bismorphine. / Morimoto, Satoshi; Suemori, Kazunari; Moriwaki, Jun; Taura, Futoshi; Tanaka, Hiroyuki; Aso, Mariko; Tanaka, Masakazu; Suemune, Hiroshi; Shimohigashi, Yasuyuki; Shoyama, Yukihiro.

In: Journal of Biological Chemistry, Vol. 276, No. 41, 12.10.2001, p. 38179-38184.

Research output: Contribution to journalArticle

Morimoto, Satoshi ; Suemori, Kazunari ; Moriwaki, Jun ; Taura, Futoshi ; Tanaka, Hiroyuki ; Aso, Mariko ; Tanaka, Masakazu ; Suemune, Hiroshi ; Shimohigashi, Yasuyuki ; Shoyama, Yukihiro. / Morphine metabolism in the opium poppy and its possible physiological function. Biochemical characterization of the morphine metabolite, bismorphine. In: Journal of Biological Chemistry. 2001 ; Vol. 276, No. 41. pp. 38179-38184.
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