New dimeric morphine from opium poppy (Papaver somuniferum) and its physiological function

Satoshi Morimoto; Kazunari Suemori; Futoshi Taura; Yukihiro Shoyama

doi:10.1021/np020583l

New dimeric morphine from opium poppy (Papaver somuniferum) and its physiological function

J Nat Prod. 2003 Jul;66(7):987-9. doi: 10.1021/np020583l.

Authors

Satoshi Morimoto¹, Kazunari Suemori, Futoshi Taura, Yukihiro Shoyama

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka, 812-8582, Japan. morimoto@phar.kyushu-u.ac.jp

PMID: 12880320
DOI: 10.1021/np020583l

Abstract

Together with bismorphine A (1), a new compound bismorphine B (2) was identified in the wounded capsules of Papaver somniferum. On the basis of analyses of the various spectral data, bismorphine B (2) was determined as a novel morphinan alkaloid, in which two morphine units are coupled through a biphenyl ether bond. When the physiological function of bismorphine B (2) in opium poppy was investigated, it was evident that this alkaloid more effectively cross-links cell wall polysaccharide pectins than bismorphine A (1) and that such cross-linking reaction leads to resistance against hydrolysis by pectinase.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids* / chemistry
Alkaloids* / isolation & purification
Alkaloids* / metabolism
Alkaloids* / pharmacology
Carbohydrate Sequence
Catalysis
Cell Wall / metabolism
Cross-Linking Reagents
Hydrolysis
Japan
Models, Molecular
Molecular Sequence Data
Molecular Structure
Morphine Derivatives* / chemistry
Morphine Derivatives* / isolation & purification
Morphine Derivatives* / metabolism
Morphine Derivatives* / pharmacology
Nuclear Magnetic Resonance, Biomolecular
Papaver / chemistry*
Plants, Medicinal / chemistry*
Polygalacturonase / metabolism*

Substances

Alkaloids
Cross-Linking Reagents
Morphine Derivatives
bismorphine A
bismorphine B
Polygalacturonase