Document Detail

Biosynthesis of mono- and sesquiterpenes in strawberry fruits and foliage: 2H labeling studies.
MedLine Citation:
PMID:  16478276     Owner:  NLM     Status:  MEDLINE    
The biosynthesis of the monoterpene (S)-linalool and the sesquiterpene trans-(S)-nerolidol in fruits of Fragaria x ananassa Duch. cv. Eros and Florence and of the monoterpene (-)-alpha-pinene in Fragaria vesca was investigated by in vivo feeding experiments with [5,5-2H2]mevalonic acid lactone (d2-MVL) and [5,5-2H2]-1-deoxy-d-xylulose (d2-DOX). The feeding experiments indicate that (S)-linalool and trans-(S)-nerolidol in Fragaria x ananassa Duch. and (-)-alpha-pinene in F. vesca are exclusively synthesized via the cytosolic mevalonic acid pathway without any contribution from the plastidial 1-deoxy-D-xylulose/2-C-methyl-D-erythritol 4-phosphate (DOXP/MEP) route. Inhibition experiments revealed that even the presence of mevastatin, an export of plastid-derived isopentyl diphosphate/dimethylallyl diphosphate, cannot be induced. However, the enantioselective analysis shows that in Fragaria x ananassa Duch. cv. Eros and Florence both linalool enantiomers are present and that only (S)-linalool is labeled after administration of d2-MVL. Therefore, the origin of (R)-linalool in these fruits remains unknown. Contrarily, in Fragaria x ananassa Duch. foliage (R)-linalool is the dominant enantiomer. Feeding experiments revealed an incorporation of d2-MVL and d2-DOX at equal rates exclusively into (S)-linalool. Only in F. vesca foliage, where (R)-linalool is present at high enantiomeric purity (ee > 90%), is a de novo biosynthesis of the (R)-enantiomer via the DOXP/MEP pathway detectable. These results demonstrate a complex intraplant variation of (R)- and (S)-linalool biosynthesis via the cytosolic and plastidial route.
Daniela Hampel; Armin Mosandl; Matthias Wüst
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  54     ISSN:  0021-8561     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2006 Feb 
Date Detail:
Created Date:  2006-02-15     Completed Date:  2006-04-06     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1473-8     Citation Subset:  IM    
Institut für Lebensmittelchemie, Johann Wolfgang Goethe-Universität, Marie-Curie-Strasse 9, D-60439 Frankfurt/Main, Germany.
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MeSH Terms
Fragaria / metabolism*
Fruit / metabolism*
Gas Chromatography-Mass Spectrometry
Mevalonic Acid / analogs & derivatives,  metabolism
Monoterpenes / metabolism*
Plant Leaves / metabolism*
Sesquiterpenes / metabolism*
Xylulose / analogs & derivatives,  metabolism
Reg. No./Substance:
0/Monoterpenes; 0/Sesquiterpenes; 150-97-0/Mevalonic Acid; 503-48-0/mevalonolactone; 5962-29-8/Xylulose; 60299-43-6/1-deoxy-2-pentulose; 7212-44-4/nerolidol; 7782-39-0/Deuterium; 78-70-6/linalool

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

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