This study estimates the classification criteria which distinguishes the types of omega-3 health functional foods, fish oils and fish oil usages through 13C-NMR spectra and fatty acids contents analysis. The major fatty acids of omega-3, eicosapentaenoic acid (EPA, C20:5) and docosahexaenoic acid (DHA, C22:6) are being analyzed. 10 ethyl ester (EE) forms and 10 triglyceride (TG) forms are the most common types of fish oils for 20 omega-3 products. Gas chromatography (GC) analysis generally shows the matching EPA and DHA contents of the products listed on the notation. But EE form contents of EPA and DHA are higher and are more varied than the TG form. Most of the samples of EPA/DHA ratio show different content ratios of indicated on the products when comparing with standards. The 13C-NMR analysis of EPA and DHA on sn-1,3 and sn-2 carbonyl peak position with fish oil triglycerides display whether the reconstituted triglycerides (rTG) are being confirmed or not. As a result of the 9 TG form, the 10 TG products showed similar values: EPA sn-1, 3; 13.46~15.66, sn-2; 3.00~4.52, DHA sn-1, 3; 2.43~4.40, sn-2; 3.84~6.36. But one product showed lower contents (EPA: sn-1, 3; 5.88, sn-2; 2.86, DHA sn-1, 3; 2.29, sn-2; 5.95) of EPA, thus it can be considered a different type of oil and only matched six products according to the label. This study is intended to provide basic materials which identify the status for the types and quality of omega-3 fish oil products according to fatty acids profiles and the 13C-NMR spectrum confirmed the location specificity of EPA and DHA.

Fatty acid compositions of the seed oils of P. schinseng, A. continentalis and A. sessiliflorus, were analyzed by gas chromatography (GC) equipped with a capillary column. A large unusual peak was observed just before the peak corresponding to oleic acid (cis-9-C18:1). This unknown fatty acid was isolated by silver ion chromatography and then derivatized into the picolinyl ester. The mass spectrum of the picolinyl ester showed molecular ion at m/z=373 with other diagnostic ions such as m/z=178, 218, 232, 246, 274, 288, 302 and 344. Characteristic absorption peaks at 720 cm-1, 1640 cm-1 and 3010 cm-1 in IR spectrum indicated the presence of cis-configurational double bond in the molecule. The 1H-NMR spectrum of this acid gave two quintets centered at δ1.638 (2H, C-3) and δ1.377 (2H, C-4), and two multiplets centered at δ2.022~2.047 (2H, C-5) and δ2.000~2.022 (2H, C-8), and multiplet signals of olefinic protons centered at δ5.3015~5.3426 (C-6, J=9.5 Hz) and δ 5.3465~5.3877 (C-7, J=9.5 Hz). The 13C-NMR spectrum showed 18 carbon resonance signals including an overlapped signal at δ29.7002 for C-12 and δ29.6520 for C-13 (or they can be reversed), and other highly resolved signals at δ33.950, δ24.558, δ26.773 and δ27.205 due to C-2, C-3, C-5 and C-8 of a δ6-octadecenoic acid, respectively. From analysis results this unknown fatty acid could be identified as cis-6-octadecenoic acid. The seed oils of P. schinseng and A. sessiliflorus contained petroselinic acid (59.7%, 56.0%), oleic acid (18.3%, 6.1%) and linoleic acid (16.2%, 30.4%) with small amount of palmitic acid (3.0%, 3.1%) while the seed oil of A. continentalis comprised mainly oleic acid (30.2%), petroselinic acid (29.0%), linoleic acid (24.1%) and palmitic acid (13.1%).

All the triacylglycerols including the molecular species having δ5-unsaturated fatty acids from the seeds of Pinus Koraiensis, were split into a mixture of diacylglycerols by a Grignard reagent prepared with allyl bromide without arousing acyl chains of a glycerol moiety to migration, and were also easily partially hydrolyzed to diacylglycerols by pancreatic lipase. (S)-(+)-(1-naphthyl)ethyl urethane(NEU) derivatives of the diacylglycerol mixture derived from the triacylglycerols were fractionated into sn-1, 3-, sn-1, 2- and sn-2, 3-DG-NEU by silica-HPLC and the fatty acid composition of these fractions was analysed. C18:1Ω9 is distributed evenly in the three positions of TG with C18:2Ω6 mainly located in sn-2 position, while δ5-unsaturated fatty acids such as δ5.9-C18:2, δ5.9.12-C18:3 and δ5.11.14-C20:3 are exclusively present in the sn-3 position. These results could be confirmed by 13C-NMR spectroscopy : the signals at δ173.231 ppm and δ172.811 ppm of the carbonyl carbon of acyl moieties indicate the presence of saturated acids and/or C18:1Ω9 (oleic acid) in the α(α')- or β- positions, and C18:2Ω6 including C18:1Ω9 in the β-position, respectively. In addition, the resonance at δ173.044 ppm suggested a location of δ5-unsaturated fatty acid moiety in the α(α')-position.