Document Detail


Pandanus alkaloids in Stemonaceae: finding of a plausible biogenetic origin of Stemona alkaloids.
MedLine Citation:
PMID:  19725518     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The isolation of (Z,Z)-pandanamine (1) and its corresponding isomers (Z,E)-pandanamine (2) and (E,E)-pandanamine (3) from Stichoneuron calcicola of the family Stemonaceae is of outstanding chemosystematic importance. This alkaloid was previously only known from the family Pandanaceae, where it was accompanied by a series of pyrrolidines, collectively called Pandanus alkaloids. The pyrrolidines pandamarilactonines A (4), B (5), C (6), and D (7) were also detected in the present study, most likely representing artificial cyclization products of pandanamine (1-3) formed by acidic conditions during chromatographic separation on silica gel. Similar structures were found in various Stemona alkaloids, suggesting a close relationship between the two plant families. Structurally, pandanamine (1-3) can be regarded as a direct precursor of croomine (8), originally isolated from Croomia, a genus closely related to Stichoneuron, but later also found in various Stemona species. The co-occurrence of pandanamine (1-3), croomine (8), and stichoneurin (9) in the family Stemonaceae represents a sound argument for a new interpretation of the biogenetic origin of Stemona alkaloids and at the same time substantiates the removal of the family from the order Dioscoreales and its inclusion into Pandanales, as already suggested by DNA sequencing.
Authors:
Harald Greger; Johann Schinnerl; Srunya Vajrodaya; Lothar Brecker; Otmar Hofer
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of natural products     Volume:  72     ISSN:  1520-6025     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2009 Sep 
Date Detail:
Created Date:  2009-09-25     Completed Date:  2009-10-21     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1708-11     Citation Subset:  IM    
Affiliation:
Comparative and Ecological Phytochemistry, Faculty Center of Botany, University of Vienna, Vienna, Austria. harald.greger@univie.ac.at
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MeSH Terms
Descriptor/Qualifier:
Alkaloids / chemistry,  isolation & purification*
Furans / chemistry,  isolation & purification*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Leaves / chemistry
Plant Stems / chemistry
Pyrrolidines / chemistry
Spiro Compounds / chemistry
Stemonaceae / chemistry*
Stereoisomerism
Chemical
Reg. No./Substance:
0/Alkaloids; 0/Furans; 0/Pyrrolidines; 0/Spiro Compounds; 0/pandanamine; 71239-66-2/croomine

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


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