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Biosynthesis of R ‐(+)‐octane‐1’3‐diol. Crucial role of β‐oxidation in the enantioselective generation of 1’3‐diols in stored apples
Author(s) -
Beuerle Till,
Schwab Wilfried
Publication year - 1999
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-999-0406-4
Subject(s) - enantioselective synthesis , diol , chemistry , octane , organic chemistry , biosynthesis , lipidology , stereochemistry , clinical chemistry , catalysis , biochemistry , enzyme
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‐ 3 H]linoleic acid’ [9’10’12’13’15’16‐ 3 H]linolenic acid’ [1‐ 14 C]linoleic acid’ [U‐ 14 C]oleic acid’ lipoxygenase‐derived metabolites of [9’10’12’13‐ 3 H]linoleic acid’ 13 C 18 ‐labeled linoleic acid hydroperoxides’ and 2 H‐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.