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 language | English |
|---|---|
| Pages (from-to) | 38179-38184 |
| Number of pages | 6 |
| Journal | Journal of Biological Chemistry |
| Volume | 276 |
| Issue number | 41 |
| DOIs | |
| Publication status | Published - Oct 12 2001 |
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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 journal › Article
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TY - JOUR
T1 - Morphine metabolism in the opium poppy and its possible physiological function. Biochemical characterization of the morphine metabolite, bismorphine
AU - Morimoto, Satoshi
AU - Suemori, Kazunari
AU - Moriwaki, Jun
AU - Taura, Futoshi
AU - Tanaka, Hiroyuki
AU - Aso, Mariko
AU - Tanaka, Masakazu
AU - Suemune, Hiroshi
AU - Shimohigashi, Yasuyuki
AU - Shoyama, Yukihiro
PY - 2001/10/12
Y1 - 2001/10/12
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0035851170&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0035851170&partnerID=8YFLogxK
U2 - 10.1074/jbc.M107105200
DO - 10.1074/jbc.M107105200
M3 - Article
C2 - 11498543
AN - SCOPUS:0035851170
VL - 276
SP - 38179
EP - 38184
JO - Journal of Biological Chemistry
JF - Journal of Biological Chemistry
SN - 0021-9258
IS - 41
ER -