Identification of furan fatty acids in the lipids of common carp (Cyprinus carpio L.)
Introduction
Furan fatty acids (F-acids) are widespread naturally occurring heterocyclic compounds. They are characterized by a furan ring, which is substituted with an unbranched fatty acid chain (typically with 7, 9, 11 or 13 carbons) in the α-position whereas the α′-position usually carries a propyl or pentyl moiety (Fig. 1). The β-/β′-positions of the furan ring are either both occupied by methyl groups or methyl is found only in the β-position adjacent to the fatty acid chain.
F-acids are generated in plants, algae (Batna, Scheinkonig, & Spiteller, 1993) and marine bacteria (Shirasaka, Nishi, & Shimizu, 1997), while other organisms accumulate these specific fatty acids in tissues after a nutritional intake (Spiteller, 2007). F-acids have been reported as minor constituents in a variety of living organisms (Spiteller, 2005), including aquatic organisms. A number of food samples and products of both plant and animal origin have also been examined for the presence of F-acids (Boselli et al., 2000, Vetter et al., 2012). Compared with other foods, fish are a particularly rich source of F-acids (Vetter et al., 2012).
Positive effect of the consumption of fish and fish oils on human health is well known. Numerous studies confirmed the reduction of the incidence of many diseases including cardiovascular diseases, cancer, inflammatory and autoimmune diseases as well as psychiatric and mental illnesses (Kris-Etherton et al., 2002, Saravanan et al., 2010, Simopoulos, 2002). The health benefits are ascribed to the presence of polyunsaturated fatty acids (PUFA) of the n-3 family, such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Nevertheless, several studies have recognized a possible active role of F-acids (Okada et al., 1996, Pacetti et al., 2010, Spiteller, 2005, Spiteller, 2007, Teixeira et al., 2013, Wakimoto et al., 2011). It has been proposed (Okada et al., 1996) that F-acids with the electron-rich furan ring may be a part of the antioxidative protection mechanisms of highly unsaturated compounds, such as PUFA. F-acids may inhibit the progression of non-enzymatic lipid peroxidation reactions (Spiteller, 2007) that seem to be responsible for aging and age dependent diseases. More recently, Teixeira et al. (2013) showed that F-acids efficiently rescue the brain cells death which can be induced by the oxidative stress. Wakimoto et al. (2011) reported in vivo activity of F-acids, confirming that these minor components in the lipid extract of the New Zealand green-lipped mussel have exhibited more potent anti-inflammatory activity than EPA. Pacetti et al. (2010) demonstrated a positive correlation between total F-acids and EPA contents in the fillet of six fish species from the Adriatic Sea.
Freshwater fish can also serve as an important source of nutritionally valuable fatty acids (Ackman, 2002) but still only limited information on F-acids content in their tissues has been available. Common carp, Cyprinus carpio, has been one of the widely cultured freshwater species due to its fast growth rate and easy cultivation (Guler, Kiztanir, Aktumsek, Citil, & Ozparlak, 2008). Nevertheless, existing information (Glass et al., 1977, Gunstone et al., 1978, Ishii et al., 1988a) on F-acids level in this species has been fractional.
The aim of our study was to examine the fatty acid composition of different edible parts of common carp (muscle, male and female gonad tissues) with special attention to F-acids and their distribution within the lipid fractions.
Section snippets
Samples
Fresh fish (3 year old individuals with fully developed gonads and weight ranging from 2.5 to 3 kg) were purchased at a local market. The samples were taken during November and December from fish prepared for Christmas Holiday market when a considerable proportion of freshwater fish is consumed. Fish were brought to the laboratory and sampled on the same day. The muscle (white dorsal muscle tissue without skin), female and male gonad tissues were collected from 13, 18 and 19 individuals,
Lipid content
The contents of total lipids and lipid fractions determined in the carp tissues are presented in Table 2. The total lipid content in white dorsal muscle tissue without skin analyzed in this study was 5.51%. Common carp thus can be classified as a medium fat fish, since the value is within the range of 5–10% (Li, Sinclair, & Li, 2011). Similarly, Guler et al. (2008) and Li et al. (2011) reported values of 4.45% and 5.35%, respectively. On the other hand, the total lipid contents for carps from
Conclusion
Common carp fatty acids in four lipid fractions (PL, DAG, FFA and TAG) were analyzed. A particular attention was focused on furan fatty acids. Differences were found among the studied tissues in terms of lipid fraction proportions as well as FA categories within the fractions. Eight F-acids were identified in the studied tissues. The major content of F-acids was present in triacylglycerol fraction of male gonad tissue. In female gonad tissue, F-acids were detected in polar lipids and
Acknowledgment
We are grateful to Prof. Kalač for a careful reading of the final version of this manuscript.
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2018, Journal of Food Composition and AnalysisCitation Excerpt :Most commonly, the β-position is substituted with a methyl group and the β’-position with either hydrogen (monomethyl-substituted furan-FAs) or with another methyl group (dimethyl-substituted furan-FAs). The main furan-FAs in marine animals, oils and plants were found to be 12,15-epoxy-13,14-dimethyleicosa-12,14-dienoic acid (11D5), 12,15-epoxy-13,14-dimethyloctadeca-12,14-dienoic acid (11D3), 10,13-epoxy-11,12-dimethyloctadeca-10,12-dienoic acid (9D5), 12,15-epoxy-13-methyleicosa-12,14-dienoic acid (11M5), and 10,13-epoxy-11-methyloctadeca-10,12-dienoic acid (9M5) (Balzano et al., 2017; Boselli et al., 2000; Chvalová and Špička, 2016; Glass et al., 1974; Gunstone et al., 1978; Guth and Grosch, 1991; Hannemann et al., 1989; Masanetz et al., 1998; Masanetz and Grosch, 1998; Mawlong et al., 2016; Pacetti et al., 2013, 2010; Sigrist et al., 2001; Vetter et al., 2016; Wahl et al., 1994b, 1994a; Wendlinger and Vetter, 2014). Occasionally, unsaturated furan-FAs bearing a double bond in either the carboxyalkyl or the alkyl side chain have also been described (Boselli et al., 2000; Ishii et al., 1988; Pacetti et al., 2010; Wendlinger et al., 2016).
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2017, Progress in Lipid ResearchCitation Excerpt :Hevea brasiliensis latex was discovered as the second plant source containing furan fatty acids in 1978 [43]. Subsequently, furan fatty acids were detected in a growing number of marine and freshwater fish [19,20,44–56], plants [11,15,43,57–61], algae [16,62], crustaceans [63–68], mammals [69], amphibians and reptiles [64], human tissues [12,13,70], fungi [15,19], ascidian [71], food [19,21–23,37,72–77], bacteria [17,78–80], bivalvia [24,66] and echinoidea [81]. During this period of time, two different types of furan fatty acids including odd carbon atom-numbered furan fatty acids and olefinic furan fatty acids were identified with the improvements of separation and detection methods.
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