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J. Biol. Chem., Vol. 263, Issue 32, 16619-16625, 11, 1988
Y Hirata, H Hayashi, S Ito, Y Kikawa, M Ishibashi, M Sudo, H Miyazaki, M Fukushima, S Narumiya and O Hayaishi
We have developed a highly sensitive and specific solid-phase enzyme
immunoassay for 9-deoxy-delta 9,delta 12-dihydroprostaglandin D2 (delta
12-PGJ2) and studied the occurrence of this novel PGD2 metabolite in human
urine. The assay detected delta 12-PGJ2 over the range of 2-200 pg, and the
antiserum showed 2% cross-reaction with PGJ2 and less than 0.2% with other
PGs. We used this assay and purified the delta 12-PGJ2- like immunoreactive
substance from human urine. Purification consisted of chromatographies on a
Sep-Pak C18 cartridge, a silicic acid column, reversed-phase
high-performance liquid chromatography, and finally an affinity column of
anti-delta 12-PGJ2 antibody. As a result, about 850 ng of delta
12-PGJ2-like immunoreactive substance were recovered from 60 liters of
human urine. The purified material was identified as delta 12-PGJ2 by gas
chromatography/high resolution-selected ion monitoring using the molecular
ion m/z 448[M]+. and ions [M - 15]+, [M - 43]+, [M - 100]+., and [M -
143]+. The amounts of delta 12-PGJ2 in the urine from normal, volunteer men
and women were 151.5 +/- 20.0 and 65.6 +/- 5.4 ng/24 h (mean +/- S.E., n =
5), respectively. The delta 12-PGJ2 amount in urine did not alter
significantly during storage for at least 24 h or by the addition of
authentic PGD2 to urine samples, suggesting that the delta 12-PGJ2 we
determined was not derived from the decomposition of PGD2 in the urine
during storage or purification. Moreover, when a single dose of PGD2 (1
mg/kg) was injected intravenously into cynomolgus monkeys, the urinary
level of delta 12-PGJ2 increased 20- to 180-fold over the normal levels,
whereas the delta 12-PGJ2 level decreased by 40-50% of the normal levels,
following the administration of indomethacin at a dose of 1 mg/kg. These
results indicate that delta 12-PGJ2 is formed naturally in the body and
excreted as a urinary PGD2 metabolite.
Occurrence of 9-deoxy-delta 9,delta 12-13,14-dihydroprostaglandin D2 in human urine
Hayaishi Bioinformation Transfer Project, Research Development Corporation of Japan, Kyoto.
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