The transformation of 12 radioactively labeled compounds into
2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF), glycosidically bound DMHF, and
2,5-dimethyl-4-methoxy-3(2H)-furanone (DMMF)
was investigated in detached ripening strawberry fruits (Fragaria
× ananassa) over a 3-day period.
Radiochemical analysis of the different fruit parts revealed that
major portions of the applied
radioactivity (up to 66%) remained in the stems and calyx.
Incorporation levels of [2-14C]dihydroxyacetone, d-[1-3H]glucose,
d-[U-14C]-glucose,
d-[U-14C]glucose 6-phosphate,
d-[U-14C]fructose,
and d-[U-14C]fructose 1,6-bisphosphate
into the total amount of furanone derivatives were 0.022,
0.032, 0.035, 0.147, 0.202, and 0.289% of the radioactivity entering
the fruits, respectively. Minor
amounts of radioactivity (<0.001%) were detected in the furanone
structures after the administration
of [1-14C]acetate and
[3-14C]pyruvate.
l-[1-14C]Fucose,
l-[6-3H]fucose,
l-[1-3H]rhamnose,
l-[U-14C]threonine, l-[U-14C]lactaldehyde, and
[2-14C]malonic acid were not transformed into DMHF
or a
derivative thereof.
Keywords: Biosynthesis; carbohydrate metabolism;
2,5-dimethyl-4-hydroxy-3(2H)-furanone; Fragaria × ananassa; Rosaceae
The transformation of
S-[methyl-14C]adenosyl-l-methionine
(14C-SAM) and [2-(or
5-)methyl-14C]-2,5-dimethyl-4-hydroxy-3(2H)-furanone
(14C-1) was investigated in detached ripening
strawberry
fruits over a three-day period. Radiochemical analysis of the
different fruit parts revealed that
46% and 51% of the applied 14C remained in the stems for
14C-SAM and 14C-1, respectively.
In
samples obtained by solid phase extraction, 1,
2,5-dimethyl-4-methoxy-3(2H)-furanone (2),
and
glycosidically bound 1 were analyzed by reversed-phase
high-performance liquid chromatography.
Incorporation of 14C-SAM and
14C-1 into 2 was observed with
transformation rates of 0.4% and
0.3% of the applied 14C, respectively. In addition,
0.7% of the applied 14C-1 was recovered
as
glycosidically bound 1. The data support the
conclusions that 14C-SAM is the source of the
methyl
group in the 4-methoxy compound 2 and that 1 is
the precursor of 2 and the glycosides studied.
Keywords: 2,5-Dimethyl-4-hydroxy-3(2H)-furanone;
2,5-dimethyl-4-methoxy-3(2H)-furanone; Furaneol; methoxyfuraneol; S-adenosyl-l-methionine; metabolism;
strawberry
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