New dimeric morphine from opium poppy (Papaver somuniferum) and its physiological function.
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.
Morimoto
Satoshi
S
Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka, 812-8582, Japan. morimoto@phar.kyushu-u.ac.jp
Suemori
Kazunari
K
Taura
Futoshi
F
Shoyama
Yukihiro
Y
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D002240:Carbohydrate Sequence; D002384:Catalysis; D002473:Cell Wall / Q000378:metabolism; D003432:Cross-Linking Reagents; D006868:Hydrolysis; D007564:Japan; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009022:Morphine Derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D010207:Papaver / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D011096:Polygalacturonase / Q000378:metabolism*
D000470:Alkaloids; D003432:Cross-Linking Reagents; D009022:Morphine Derivatives; C438503:bismorphine A; C479861:bismorphine B; D011096:Polygalacturonase