Identification of a major iodolipid from the horse thyroid gland as 2-iodohexadecanal.
Abstract: The incorporation of iodide into proteins (PBI) and lipids (LBI) of horse thyroid slices was measured in various conditions. Their dependency on the concentration of extracellular iodide was strikingly different. For PBI the relationship was biphasic with a decrease above 10 microM, likely to correspond to the Wolff-Chaikoff effect. On the contrary, LBI increased as a function of iodide concentration up to 100 microM. Methimazole (MMI) inhibited the incorporation of iodide into both LBI and PBI, but higher concentrations of MMI were required to depress LBI as compared to PBI. The inhibition of active iodide transport by NaCIO4 reduced both PBI and LBI. Chromatography on silica gel resolved almost equal amounts of low and high polarity iodolipids. The main unpolar iodolipid was identified as 2-iodohexadecanal (2-IHDA), on the basis of proton nuclear magnetic resonance spectroscopy, mass spectrometry, and co-elution with authentic 2-IHDA obtained by chemical synthesis in reversed-phase high performance liquid chromatography and gas chromatography. The presence of 2-IHDA was also detected in dog thyroid slices, following incubation with KI (50 microM) and in the rat thyroid, 4 hours after intraperitoneal injection of KI (650 micrograms). An incubation of bovine brain plasmalogens with lactoperoxidase, iodide, and H2O2 generated 2-IHDA. In conclusion, we have identified a major thyroid iodolipid as 2-iodohexadecanal. The biosynthesis of this compound is likely to involve the addition of iodine to the vinyl ether group of plasmalogens.
Publication Date: 1990-10-05 PubMed ID: 2211608
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- Journal Article
- Research Support
- Non-U.S. Gov't
Summary
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Researchers have identified a major iodolipid in the horse thyroid gland as 2-iodohexadecanal, and examined how various conditions impact the incorporation of iodide into proteins and lipids. Experimentation revealed that for proteins, too much iodide led to a decrease, mirroring the Wolff-Chaikoff effect. However, lipids showed an increase corresponding to iodide concentrations. Manipulations using Methimazole and NaCIO4 were also employed to further understand iodide behavior.
Iodide Incorporation into Proteins and Lipids
- The study investigated how iodide incorporation into proteins (PBI) and lipids (LBI) of horse thyroid slices varied under different conditions.
- The researchers observed a distinct difference in how PBI and LBI behaved in response to iodide concentrations. With the concentration of iodide increasing above 10 microM, there was a resultant decrease in PBI. This is thought to reflect the Wolff-Chaikoff effect, a phenomenon where high levels of iodine can temporarily inhibit thyroid hormone synthesis. On the other hand, LBI levels increased as a function of iodide concentration up to 100 microM.
Influence of Methimazole and NaCIO4
- The experiment also entailed looking at how Methimazole (MMI), a medication used to treat hyperthyroidism, affected iodide incorporation. MMI was found to inhibit both LBI and PBI, although a higher concentration of MMI was required to affect LBI as compared to PBI.
- Active iodide transport was also inhibited as part of the study, specifically through the use of NaCIO4. This resulted in both PBI and LBI reducing.
Identification of Iodolipid 2-Iodohexadecanal
- Chromatography was used in the study to identify the iodolipids present. Here they found almost equal amounts of low and high polarity iodolipids, with the main unpolar iodolipid being identified as 2-iodohexadecanal (2-IHDA).
- The identification of 2-IHDA was validated using proton nuclear magnetic resonance spectroscopy, mass spectrometry, and comparative methods with authentic synthetic 2-IHDA as a baseline.
- Further experimentation found the presence of 2-IHDA in dog thyroid slices, following incubation with a potassium iodide solution, and in rat thyroid, after the rats were administered an injection of KI.
In conclusion, the major thyroid iodolipid was identified as 2-iodohexadecanal, and its biosynthesis is thought to involve the addition of iodine to the vinyl ether group of a class of lipids known as plasmalogens.
Cite This Article
APA
Pereira A, Braekman JC, Dumont JE, Boeynaems JM.
(1990).
Identification of a major iodolipid from the horse thyroid gland as 2-iodohexadecanal.
J Biol Chem, 265(28), 17018-17025.
Publication
Researcher Affiliations
- Institute of Interdisciplinary Research, School of Medicine, Free University of Brussels, Belgium.
MeSH Terms
- Aldehydes / isolation & purification
- Animals
- Chromatography, High Pressure Liquid
- Dogs
- Horses
- In Vitro Techniques
- Iodides / metabolism
- Iodine Radioisotopes
- Kinetics
- Lipids / biosynthesis
- Lipids / isolation & purification
- Magnetic Resonance Spectroscopy
- Male
- Mass Spectrometry
- Rats
- Rats, Inbred Strains
- Species Specificity
- Thyroid Gland / chemistry
- Thyroid Gland / metabolism
Citations
This article has been cited 10 times.- Kurashige T, Shimamura M, Nagayama Y. Reevaluation of the Effect of Iodine on Thyroid Cell Survival and Function Using PCCL3 and Nthy-ori 3-1 Cells.. J Endocr Soc 2020 Nov 1;4(11):bvaa146.
- Ebenezer DL, Fu P, Ramchandran R, Ha AW, Putherickal V, Sudhadevi T, Harijith A, Schumacher F, Kleuser B, Natarajan V. S1P and plasmalogen derived fatty aldehydes in cellular signaling and functions.. Biochim Biophys Acta Mol Cell Biol Lipids 2020 Jul;1865(7):158681.
- Ziros PG, Habeos IG, Chartoumpekis DV, Ntalampyra E, Somm E, Renaud CO, Bongiovanni M, Trougakos IP, Yamamoto M, Kensler TW, Santisteban P, Carrasco N, Ris-Stalpers C, Amendola E, Liao XH, Rossich L, Thomasz L, Juvenal GJ, Refetoff S, Sykiotis GP. NFE2-Related Transcription Factor 2 Coordinates Antioxidant Defense with Thyroglobulin Production and Iodination in the Thyroid Gland.. Thyroid 2018 Jun;28(6):780-798.
- Palladino END, Hartman CL, Albert CJ, Ford DA. The chlorinated lipidome originating from myeloperoxidase-derived HOCl targeting plasmalogens: Metabolism, clearance, and biological properties.. Arch Biochem Biophys 2018 Mar 1;641:31-38.
- Duan Q, Wang T, Zhang N, Perera V, Liang X, Abeysekera IR, Yao X. Propylthiouracil, Perchlorate, and Thyroid-Stimulating Hormone Modulate High Concentrations of Iodide Instigated Mitochondrial Superoxide Production in the Thyroids of Metallothionein I/II Knockout Mice.. Endocrinol Metab (Seoul) 2016 Mar;31(1):174-84.
- Portulano C, Paroder-Belenitsky M, Carrasco N. The Na+/I- symporter (NIS): mechanism and medical impact.. Endocr Rev 2014 Feb;35(1):106-49.
- Penglase S, Harboe T, Sæle O, Helland S, Nordgreen A, Hamre K. Iodine nutrition and toxicity in Atlantic cod (Gadus morhua) larvae.. PeerJ 2013;1:e20.
- Ullen A, Fauler G, Bernhart E, Nusshold C, Reicher H, Leis HJ, Malle E, Sattler W. Phloretin ameliorates 2-chlorohexadecanal-mediated brain microvascular endothelial cell dysfunction in vitro.. Free Radic Biol Med 2012 Nov 1;53(9):1770-81.
- Hard GC. Recent developments in the investigation of thyroid regulation and thyroid carcinogenesis.. Environ Health Perspect 1998 Aug;106(8):427-36.
- Golstein J, Dumont JE. Cytotoxic effects of iodide on thyroid cells: difference between rat thyroid FRTL-5 cell and primary dog thyrocyte responsiveness.. J Endocrinol Invest 1996 Feb;19(2):119-26.
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