Increased Serum Level of Cyclopropaneoctanoic Acid 2-Hexyl in Patients with Hypertriglyceridemia-Related Disorders

Adriana Mika, Piotr Stepnowski, Michal Chmielewski, Sylwia Malgorzewicz, Lukasz Kaska, Monika Proczko, Krzysztof Ratnicki-Sklucki, Maciej Sledzinski, Tomasz Sledzinski, Adriana Mika, Piotr Stepnowski, Michal Chmielewski, Sylwia Malgorzewicz, Lukasz Kaska, Monika Proczko, Krzysztof Ratnicki-Sklucki, Maciej Sledzinski, Tomasz Sledzinski

Abstract

We recently reported the presence of various cyclopropane fatty acids-among them, cyclopropaneoctanoic acid 2-hexyl-in the adipose tissue of obese women. The aim of this study was to verify whether the presence of cyclopropaneoctanoic acid 2-hexyl in human serum was associated with obesity or chronic kidney disease (both being related to dyslipidemia), and to find potential associations between the serum level of this compound and specific markers of the these conditions. The serum concentration of cyclopropaneoctanoic acid 2-hexyl was determined by gas chromatography-mass spectrometry (GC-MS) in non-obese controls, obese patients, obese patients after a 3-month low-calorie diet, and individuals with chronic kidney disease. Obese patients and those with chronic kidney disease presented with higher serum levels of cyclopropaneoctanoic acid 2-hexyl than controls. Switching obese individuals to a low-calorie (low-lipid) diet resulted in a reduction in this fatty acid concentration to the level observed in controls. Cyclopropaneoctanoic acid 2-hexyl was also found in foods derived from animal fat. Serum concentrations of triacylglycerols in the analyzed groups followed a pattern similar to that for serum cyclopropaneoctanoic acid 2-hexyl, and these variables were positively correlated with each other among the studied groups. Patients with hypertriglyceridemia-related conditions presented with elevated serum levels of cyclopropaneoctanoic acid 2-hexyl. Our findings suggest that its high serum level is related to high serum triacylglycerol concentrations rather than to body mass or BMI.

Keywords: Chronic kidney disease; Cyclopropaneoctanoic acid 2-hexyl; Hypertriglyceridemia; Obesity.

Figures

Fig. 1
Fig. 1
Serum concentrations of cyclopropaneoctanoic acid 2-hexyl in study subjects, including non-obese controls, obese patients, obese subjects after a 3-month low-calorie (low-lipid) diet and individuals with chronic kidney disease (CKD). Data are presented as mean ± SEM. *p < 0.05 compared to the controls

References

    1. Grogan DW, Cronan JE., Jr Cyclopropane ring formation in membrane lipids of bacteria. Microbiol Mol Biol Rev. 1997;61:429–441.
    1. Rahman MD, Ziering DL, Mannarelli SJ, Swartz KL, Huang DS, Pascal RA., Jr Effects of sulfur-containing analogues of stearic acid on growth and fatty acid biosynthesis in the protozoan Crithidia fasciculata. J Med Chem. 1988;31:1656–1659. doi: 10.1021/jm00403a029.
    1. Yu XH, Rawat R, Shanklin J. Characterization and analysis of the cotton cyclopropane fatty acid synthase family and their contribution to cyclopropane fatty acid synthesis. BMC Plant Biol. 2011;11:97. doi: 10.1186/1471-2229-11-97.
    1. Yu XH, Prakash RR, Sweet M, Shanklin J. Coexpressing Escherichia coli cyclopropane synthase with Sterculia foetida Lysophosphatidic acid acyltransferase enhances cyclopropane fatty acid accumulation. Plant Physiol. 2014;164:455–465. doi: 10.1104/pp.113.230953.
    1. Carballeira NM, Montano N, Vicente J, Rodriguez AD. Novel cyclopropane fatty acids from the phospholipids of the Caribbean sponge Pseudospongosorites suberitoides. Lipids. 2007;42:519–524. doi: 10.1007/s11745-007-3047-3.
    1. Rob T, Ogi T, Maarisit W, Taira J, Ueda K. Isolation of C(1)(1) compounds and a cyclopropane fatty acid from an Okinawan ascidian, Diplosoma sp. Molecules. 2011;16:9972–9982. doi: 10.3390/molecules16129972.
    1. Sakurada K, Iwase H, Takatori T, Nagao M, Nakajima M, Niijima H, Matsuda Y, Kobayashi M. Identification of cis-9,10-methylenehexadecanoic acid in submitochondrial particles of bovine heart. Biochim Biophys Acta. 1999;1437:214–222. doi: 10.1016/S1388-1981(99)00016-5.
    1. Sledzinski T, Mika A, Stepnowski P, Proczko-Markuszewska M, Kaska L, Stefaniak T, Swierczynski J. Identification of cyclopropaneoctanoic acid 2-hexyl in human adipose tissue and serum. Lipids. 2013;48:839–848. doi: 10.1007/s11745-013-3806-2.
    1. Dong L, Vecchio AJ, Sharma NP, Jurban BJ, Malkowski MG, Smith WL. Human cyclooxygenase-2 is a sequence homodimer that functions as a conformational heterodimer. J Biol Chem. 2011;286:19035–19046. doi: 10.1074/jbc.M111.231969.
    1. Sakurada K, Iwase H, Kobayashi M, Uemura H, Nakaya H, Ikegaya H, Yoshida K. cis-9,10-Methylenehexadecanoic acid inhibits contractility and actomyosin ATPase activity of guinea pig myocardium. Biochem Biophys Res Commun. 2000;274:533–536. doi: 10.1006/bbrc.2000.3181.
    1. Kanno T, Yamamoto H, Yaguchi T, Hi R, Mukasa T, Fujikawa H, Nagata T, Yamamoto S, Tanaka A, Nishizaki T. The linoleic acid derivative DCP-LA selectively activates PKC-epsilon, possibly binding to the phosphatidylserine binding site. J Lipid Res. 2006;47:1146–1156. doi: 10.1194/jlr.M500329-JLR200.
    1. Kadegowda AK, Burns TA, Pratt SL, Duckett SK. Inhibition of stearoyl-CoA desaturase 1 reduces lipogenesis in primary bovine adipocytes. Lipids. 2013;48:967–976. doi: 10.1007/s11745-013-3823-1.
    1. Huang JD, Amaral J, Lee JW, Larrayoz IM, Rodriguez IR. Sterculic acid antagonizes 7-ketocholesterol-mediated inflammation and inhibits choroidal neovascularization. Biochim Biophys Acta. 2012;1821:637–646. doi: 10.1016/j.bbalip.2012.01.013.
    1. Bao X, Katz S, Pollard M, Ohlrogge J. Carbocyclic fatty acids in plants: biochemical and molecular genetic characterization of cyclopropane fatty acid synthesis of Sterculiafoetida. Proc Natl Acad Sci USA. 2002;99:7172–7177. doi: 10.1073/pnas.092152999.
    1. Aro A. Fatty acid composition of serum lipids: is this marker of fat intake still relevant for identifying metabolic and cardiovascular disorders? Nutr Metab Cardiovasc Dis. 2003;13:253–255. doi: 10.1016/S0939-4753(03)80028-5.
    1. Trevisan R, Dodesini AR, Lepore G. Lipids and renal disease. J Am Soc Nephrol. 2006;17:S145–S147. doi: 10.1681/ASN.2005121320.
    1. Masi LN, Rodrigues AC, Curi R. Fatty acids regulation of inflammatory and metabolic genes. Curr Opin Clin Nutr Metab Care. 2013;16:418–424.
    1. Fei J, Cook C, Santanam N. Omega-6 lipids regulate PPAR turnover via reciprocal switch between PGC-1 alpha and ubiquitination. Atherosclerosis. 2012;222:395–401. doi: 10.1016/j.atherosclerosis.2012.02.040.
    1. Yang ZH, Miyahara H, Hatanaka A. Chronic administration of palmitoleic acid reduces insulin resistance and hepatic lipid accumulation in KK-Ay Mice with genetic type 2 diabetes. Lipids Health Dis. 2011;10:120. doi: 10.1186/1476-511X-10-120.
    1. Caligiani A, Marseglia A, Palla G. An overview on the presence of cyclopropane fatty acids in milk and dairy products. J Agric Food Chem. 2014;62:7828–7832. doi: 10.1021/jf4057204.
    1. Folch J, Lees M, Sloane Stanley GH. A simple method for the isolation and purification of total lipids from animal tissues. J Biol Chem. 1957;226:497–509.

Source: PubMed

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