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5′-O-Methyldioncophylline D, a 7,8′-coupled naphthylisoquinoline alkaloid from callus cultures of Triphyophyllum peltatum, and its biosynthesis from a late-stage tetrahydroisoquinoline precursor

Abstract:

The natural tetrahydroisoquinoline phylline (4) was synthesized in a specifically [1,1′-13C2]-labeled form, and fed to callus cultures of Triphyophyllum peltatum. Its incorporation into naphthylisoquinoline alkaloids, among them habropetaline A (8) (as evidenced by1H,13C NMR, and 2D INADEQUATE experiments), proved 4 to be the authentic coupling substrate for the enzyme-mediated phenol-oxidative coupling with a naphthalene portion. During the feeding experiments, a new alkaloid was discovered,...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1016/j.tet.2016.04.003

Authors


Bringmann, G More by this author
Rüdenauer, S More by this author
Mutanyatta-Comar, J More by this author
More by this author
Institution:
University of Oxford
Division:
MSD
Department:
NDM; Target Discovery Institute
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Publisher:
Elsevier Publisher's website
Journal:
Tetrahedron Journal website
Volume:
72
Issue:
22
Pages:
2906-2912
Publication date:
2016-04-07
Acceptance date:
2016-04-01
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Pubs id:
pubs:864004
URN:
uri:a2cd57f0-1096-426c-b9b1-574fc5612eb6
UUID:
uuid:a2cd57f0-1096-426c-b9b1-574fc5612eb6
Local pid:
pubs:864004

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