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The National Agricultural Library is one of four national libraries of the United States, with locations in Beltsville, Maryland and Washington, D.C. It houses one of the world's largest and most accessible agricultural information collections and serves as the nexus for a national network of state land-grant and U.S. Department of Agriculture field libraries. In fiscal year 2011 (Oct 2010 through Sept 2011) NAL delivered more than 100 million direct customer service transactions.

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Journal Article

Journal Article

Isotopologue Profiling of Triterpene Formation under Physiological Conditions. Biosynthesis of Lupeol-3-(3′-R-hydroxy)-stearate in Pentalinon andrieuxii  [2014]

Peña-Rodríguez, Luis M.; Yam-Puc, Alejandro; Knispel, Nihat; Schramek, Nicholas; et al.

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The biosynthesis of lupeol-3-(3′R-hydroxy)-stearate (procrim b, 1) was investigated in the Mexican medicinal plant Pentalinon andrieuxii by ¹³CO₂ pulse-chase experiments. NMR analyses revealed positional enrichments of ¹³C₂-isotopologues in both the triterpenoid and the hydroxystearate moieties of 1. Five of the six isoprene units reflected a pattern with [1,2-¹³C₂]- and [3,5-¹³C₂]-isotopologues from the respective C₅-precursors, IPP and DMAPP, whereas one isoprene unit in the ring E of 1 showed only the [3,5-¹³C₂]-connectivity of the original C₅-precursor, due to rearrangement of the dammarenyl cation intermediate during the cyclization process. The presence of ¹³C₂-isotopologues was indicative of [¹³C₂]acetyl-CoA being the precursor units in the formation of the fatty acid moiety and of the triterpene via the mevalonate route. The observed labeling pattern was in agreement with a chair-chair-chair-boat conformation of the (S)-2,3-oxidosqualene precursor during the cyclization process, suggesting that the lupeol synthase from P. andrieuxii is of the same type as that from Olea europea and Taraxacum officinale, but different from that of Arabidopsis thaliana. The study shows that ¹³CO₂ pulse-chase experiments are powerful in elucidating, under in vivo conditions and in a single experiment, the biosynthesis of complex plant products including higher terpenes.
From the journal
Journal of organic chemistry
ISSN : 1520-6904

Bibliographic information

Language:
English
Type:
Journal Article
In AGRIS since:
2018
Volume:
79
Issue:
7
Extent:
2864-2873
Publisher:
American Chemical Society
All titles:
"Isotopologue Profiling of Triterpene Formation under Physiological Conditions. Biosynthesis of Lupeol-3-(3′-R-hydroxy)-stearate in Pentalinon andrieuxii"@eng
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Bibliographic information

Language:
English
Type:
Journal Article
In AGRIS since:
2018
Volume:
79
Issue:
7
Extent:
2864-2873
Publisher:
American Chemical Society
All titles:
"Isotopologue Profiling of Triterpene Formation under Physiological Conditions. Biosynthesis of Lupeol-3-(3′-R-hydroxy)-stearate in Pentalinon andrieuxii"@eng