TY - JOUR
T1 - Biosynthesis of R-(+)-octane-1,3-diol. Crucial role of β-oxidation in the enantioselective generation of 1,3-diols in stored apples
AU - Beuerle, Till
AU - Schwab, Wilfried
N1 - Funding Information:
We thank Dr. Pascal Brunerie for providing the apples and Thorsten König, Katja Hör, and Christiane Ruff for the GC–IRMS analyses. We extend appreciation to Prof. Gerhard Bringmann (Institute of Organic Chemistry) for the use of the radiochemical laboratory, and the assistance of Rene Roscher is gratefully acknowledged. The authors wish to thank the Deutsche Forschungsgemeinschaft (SCHW 634/1-2) and Fonds der Chemischen Industrie for funding.
PY - 1999
Y1 - 1999
N2 - The biosynthesis of R-octane-1,3-diol and R-5(Z)-octene-1,3-diol, two natural antimicrobial agents in apples and pears, was investigated in stored apples after application of [9,10,12,13-3H]linoleic acid, [9,10,12,13,15,16- 3H]linolenic acid, [1-14C]linoleic acid, [U-14C]oleic acid, lipoxygenase-derived metabolites of [9,10,12,13-3H]linoleic acid, 13C18- labeled linoleic acid hydroperoxides, and 2H-labeled octanol derivatives. Analysis of the products and quantification of incorporation and labeling pattern were achieved by high-performance liquid chromatography- radiodetection, capillary gas chromatography (GC)-isotope ratio mass spectrometry, and GC-mass spectrometry analysis. Almost all the applied precursors were partly transformed into R-octane-1,3-diol. Linoleic acid derivatives, still containing the 12,13 cis double bond, and octanol derivatives oxy-functionalized at carbon 3 were the most efficient precursors of the 1,3-diol. The data imply that R-octane-1,3-diol is generated in stored apples in the course of the β-oxidation from R-3-hydroxy-octanoyl-SCoA originating from 2-cis-octenoyl-SCoA by enoyl-CoA hydratase. In an analogous fashion, R-5(Z)-octene-1,3-diol is formed from the unsaturated intermediate.
AB - The biosynthesis of R-octane-1,3-diol and R-5(Z)-octene-1,3-diol, two natural antimicrobial agents in apples and pears, was investigated in stored apples after application of [9,10,12,13-3H]linoleic acid, [9,10,12,13,15,16- 3H]linolenic acid, [1-14C]linoleic acid, [U-14C]oleic acid, lipoxygenase-derived metabolites of [9,10,12,13-3H]linoleic acid, 13C18- labeled linoleic acid hydroperoxides, and 2H-labeled octanol derivatives. Analysis of the products and quantification of incorporation and labeling pattern were achieved by high-performance liquid chromatography- radiodetection, capillary gas chromatography (GC)-isotope ratio mass spectrometry, and GC-mass spectrometry analysis. Almost all the applied precursors were partly transformed into R-octane-1,3-diol. Linoleic acid derivatives, still containing the 12,13 cis double bond, and octanol derivatives oxy-functionalized at carbon 3 were the most efficient precursors of the 1,3-diol. The data imply that R-octane-1,3-diol is generated in stored apples in the course of the β-oxidation from R-3-hydroxy-octanoyl-SCoA originating from 2-cis-octenoyl-SCoA by enoyl-CoA hydratase. In an analogous fashion, R-5(Z)-octene-1,3-diol is formed from the unsaturated intermediate.
UR - http://www.scopus.com/inward/record.url?scp=0033016811&partnerID=8YFLogxK
U2 - 10.1007/s11745-999-0406-4
DO - 10.1007/s11745-999-0406-4
M3 - Article
C2 - 10405976
AN - SCOPUS:0033016811
SN - 0024-4201
VL - 34
SP - 617
EP - 625
JO - Lipids
JF - Lipids
IS - 6
ER -