Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney
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Arachidonic acid (5,8,11,14-eicosatetraenoic acid), the 20-carbon precursor for prostaglandin synthesis, is present in membrane lipids throughout the body and its metabolic enzyme is ubiquitously distributed.It was previously shown that adrenal glands, testis, brain, and kidney medulla contain both arachidonic acid and its chain-elongated product adrenic acid (7,10,13,16-docosatetraenoic acid).We prepared [1-14C]-adrenic acid and found that the renal medulla was the only rabbit tissue tested which readily metabolized the 22-carbon fatty acid.The major renal medullary cell type that contains adrenic acid is the renomedullary interstitial cell which we found active in converting this fatty acid into la,lbdihomo-prostaglandin Ez.Furthermore, the renomedullary cells possess recognition sites for the la,lbdihomo-prostaglandin Ez which results in an activation of adenylate cyclase when added to these cells.The renal medullary conversion of adrenic acid to dihomoprostaglandins was greatly facilitated in microsomes prepared from the ureter-obstructed (hydronephrotic) kidney.The eight major products generated by the hydronephrotic kidney were purifed by high performance liquid chromatography and upon analysis by gas chromatography-mass spectrometry were shown to be la,lb-dihomo-8-keto-prostaglandin F1, (the dihomoprostacyclin metabolite), la,lb-dihomo-thromboxane Bz, la,lb-dihomo-prostaglandin Fz,, la,lb-dihomoprostaglandin Ez, la,lb-dihomo-prostaglandin Dz, two 14-hydroxynonadecatrienoic acids (the other metabolite of thromboxane synthetase), and 13-hydroxydocosatetraenoic acid.The limited distribution of adrenic acid and the demonstrated ability of the rabbit renal medulla to metabolize this fatty acid create the possi- bility for a family of prostaglandin metabolites largely restricted to the kidney.The essential fatty acid linoleic acid (18:2) is sequentially desaturated and chain elongated to form arachidonic acid (204, 5,8,11,14-eicosatetraenoic acid), the precursor of prostaglandin (of the two series), thromboxane, and lipoxygenase products.Adrenal glands, brain, testis, and the renomedullary interstitial cells of the kidney medulla contain a significant amount of 7,10,13,16-docosatetraenoic acid (22:4) which is
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Adrenic acid increases in senescent cells.
“The 22-carbon lipid AdA, a product of AA elongation (Jump, 2009; Ohno et al., 2010) and precursor of dihomo prostaglandins (Sprecher et al., 1982), also increased in senescent cells (Figure 1B).”
From Oxylipin biosynthesis reinforces cellular senescence and allows detection of senolysis (2021) · cites this paper as Sprecher et al., 1982
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Oxylipin biosynthesis reinforces cellular senescence and allows detection of senolysis
Wiley, C. D., Sharma, R., Davis, S. S., Lopez-Dominguez, J. A., Mitchell, K. P., Wiley, S., Alimirah, F., Kim, D. E., Payne, T., Rosko, A., et al. (2021) · Cell Metabolism · doi:10.1016/j.cmet.2021.03.008 · Cited by 173 · see citing works
- Authors
- Sprecher, H., VanRollins, M., Sun, F., Wyche, A., & Needleman, P.
- Affiliations
- Washington University in St. Louis (US)
- ORCID
- Sun, F
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 1982-04
- Volume
- 257
- Issue
- 7
- Pages
- 3912-3918
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W95307264
- Cited by
- 76
- References
- 30
- Citations by year
- 2025: 1 · 2023: 1 · 2022: 1 · 2021: 4 · 2020: 1 · 2017: 2 · 2016: 1 · 2015: 2 · 2014: 2 · 2013: 1 · 2012: 3
- FWCI
- 2.72
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Eicosanoids and Hypertension Pharmacology
- Health Sciences › Medicine › Pharmacology › Inflammatory mediators and NSAID effects
- Health Sciences › Nursing › Nutrition and Dietetics › Fatty Acid Research and Health
- Keywords
- adrenic acid, renal medulla, renomedullary interstitial cells, prostaglandin synthesis, hydronephrosis, adenylate cyclase activation, prostacyclin metabolites, thromboxane synthase, linoleic acid desaturation, chain extension, prostaglandin E2
- MeSH terms
- Animals, Arachidonic Acids, Brain, Chromatography, High Pressure Liquid, Erucic Acids, Fatty Acids, Unsaturated, Kidney, Male, Microsomes, Organ Specificity, Prostaglandins E, Prostaglandins F, Seminal Vesicles, Sheep, Mass Spectrometry, Structure-Activity Relationship, Thromboxanes, Dinoprostone, Dinoprost, Arachidonic Acid
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