Document Detail

Stress-related polyketide metabolism of Dioncophyllaceae and Ancistrocladaceae.
MedLine Citation:
PMID:  11559737     Owner:  NLM     Status:  MEDLINE    
The discovery of a novel biosynthetic pathway to isoquinoline alkaloids is described. The naphthylisoquinoline alkaloid dioncophylline A, one of the most prominent representatives of a new class of structurally and pharmacologically intriguing secondary metabolites, is shown to originate from acetate units, both molecular halves, the isoquinoline part and the naphthalene portion, being formed from identical polyketide precursors. All other tetrahydroisoquinoline alkaloids previously investigated, ultimately originate from aromatic amino acids. The novel pathway to isoquinoline alkaloids (hence acetogenic) was proved by feeding experiments with (13)C-labelled precursors administered to callus cultures of Triphyophyllum peltatum (Dioncophyllaceae), followed by NMR investigations using the potent cryoprobe methodology. The new pathway is largely stress-sensitive: upon exposure to chemical, biotic or physical stress, T. peltatum stops producing the isoquinoline part, so that the naphthalene moiety accumulates in the chemical form of naphthoquinones like plumbagin and droserone and the chiral tetralone isoshinanolone.
G Bringmann; D Feineis
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Review    
Journal Detail:
Title:  Journal of experimental botany     Volume:  52     ISSN:  0022-0957     ISO Abbreviation:  J. Exp. Bot.     Publication Date:  2001 Oct 
Date Detail:
Created Date:  2001-09-17     Completed Date:  2001-12-07     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9882906     Medline TA:  J Exp Bot     Country:  England    
Other Details:
Languages:  eng     Pagination:  2015-22     Citation Subset:  IM    
Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany.
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MeSH Terms
Adaptation, Physiological
Alkaloids / chemistry,  metabolism*
Angiosperms / classification,  metabolism*
Culture Techniques
Isoquinolines / chemistry,  metabolism*
Models, Molecular
Morphine / chemistry,  metabolism
Spectrum Analysis
Reg. No./Substance:
0/Alkaloids; 0/Isoquinolines; 57-27-2/Morphine; 60142-17-8/dioncophylline A

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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