NDLI: How human neuroblastoma cells make morphine

Content Provider	PubMed Central
Author	Boettcher, Chotima Monika, Fellermeier Boettcher, Christian Dräger, Birgit Zenk, Meinhart H.
Copyright Year	2005
Abstract	Recently, our laboratory demonstrated that human neuroblastoma cells (SH-SY5Y) are capable of synthesizing morphine, the major active metabolite of opium poppy. Now our experiments are further substantiated by extending the biochemical studies to the entire morphine pathway in this human cell line. l-[1,2,3-13C3]- and [ring-2′,5′,6′-2H3]dopa showed high isotopic enrichment and incorporation in both the isoquinoline and the benzyl moiety of the endogenous morphine. [2,2-2H2]Dopamine, however, was exclusively incorporated only into the isoquinoline moiety. Neither the trioxygenated (R,S)-[1,3-13C2]norcoclaurine, the precursor of morphine in the poppy plant, nor (R)-[1,3,4-2H3]norlaudanosoline showed incorporation into endogenous morphine. However, (S)-[1,3,4-2H3]norlaudanosoline furnished a good isotopic enrichment and the loss of a single deuterium atom at the C-9 position of the morphine molecule, indicating that the change of configuration from (S)- to (R)-reticuline occurs via the intermediacy of 1,2-dehydroreticuline. Additional feeding experiments with potential morphinan precursors demonstrated substantial incorporation of [7-2H]salutaridinol, but not 7-[7-2H]episalutaridinol, and [7-2H,N-C2H3]oripavine, and [6-2H]codeine into morphine. Human morphine biosynthesis involves at least 19 chemical steps. For the most part, it is a reflection of the biosynthesis in opium poppy; however, there is a fundamental difference in the formation of the key intermediate (S)-reticuline: it proceeds via the tetraoxygenated initial isoquinoline alkaloid (S)-norlaudanosoline, whereas the plant morphine biosynthesis proceeds via the trioxygenated (S)-norcoclaurine. Following the plant biosynthetic pathway, (S)-reticuline undergoes a change of configuration at C-1 during its transformation to salutaridinol and thebaine. From thebaine, there is a bifurcate pathway leading to morphine proceeding via codeine or oripavine, in both plants and mammals.
Related Links	http://dx.doi.org/10.1073/pnas.0503244102
Ending Page	8500
Page Count	6
Starting Page	8495
File Format	PDF
ISSN	00278424
e-ISSN	10916490
Journal	Proceedings of the National Academy of Sciences of the United States of America
Issue Number	24
Volume Number	102
Language	English
Publisher	National Academy of Sciences
Publisher Date	2005-06-14
Access Restriction	Open
Rights Holder	National Academy of Sciences
Subject Keyword	General Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Multidisciplinary

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