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New dimeric morphine from opium poppy (Papaver somuniferum) and its physiological function
Satoshi Morimoto1, Kazunari Suemori, Futoshi Taura
1Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka, 812-8582, Japan. morimoto@phar.kyushu-u.ac.jp
Journal of Natural Products
|July 26, 2003
Summary
A new opium poppy alkaloid, bismorphine B, was discovered. This compound effectively cross-links pectin in plant cell walls, enhancing resistance to enzymatic degradation.
Area of Science:
- Phytochemistry
- Plant Biochemistry
- Molecular Biology
Background:
- Papaver somniferum, the opium poppy, produces a diverse array of alkaloids with significant pharmacological and biochemical roles.
- Previous research identified bismorphine A, a dimeric morphinan alkaloid, in wounded opium poppy capsules.
Purpose of the Study:
- To identify and characterize novel alkaloids from Papaver somniferum.
- To elucidate the physiological function of newly identified alkaloids, specifically bismorphine B, within the opium poppy.
- To investigate the role of bismorphine B in plant cell wall integrity and defense mechanisms.
Main Methods:
- Extraction and isolation of alkaloids from wounded Papaver somniferum capsules.
- Structure elucidation of new compounds using comprehensive spectral analyses (e.g., NMR, Mass Spectrometry).
- In vitro assays to assess the cross-linking activity of bismorphine B on plant cell wall polysaccharides (pectins).
- Enzymatic hydrolysis assays using pectinase to evaluate the effect of bismorphine B-mediated pectin cross-linking on degradation resistance.
Main Results:
- A novel morphinan alkaloid, bismorphine B (2), was identified alongside bismorphine A (1).
- Bismorphine B (2) features a unique structure where two morphine units are linked via a biphenyl ether bond.
- Bismorphine B demonstrated a superior ability to cross-link pectin polysaccharides compared to bismorphine A.
- The pectin cross-linking activity of bismorphine B conferred increased resistance to pectinase hydrolysis.
Conclusions:
- Bismorphine B is a novel morphinan alkaloid from Papaver somniferum with a unique biphenyl ether linkage.
- Bismorphine B plays a significant physiological role in opium poppy by reinforcing the cell wall through pectin cross-linking.
- This cross-linking mechanism enhances plant tissue resistance to enzymatic degradation, potentially contributing to defense against pathogens or mechanical stress.