CTA ester bonds in TG molecules were not attacked by pancreatic lipase and lipases produced by microbes such as Candida cylindracea, Chromobacterium viscosum, Geotricum candidium, Pseudomonas fluorescens, Rhizophus delemar, R. arrhizus and Mucor miehei. An aliquot of total TG of all the seed oils and each TG fraction of the oils collected from HPLC runs were deuterated prior to partial hydrolysis with Grignard reagent, because CTA molecule was destroyed with treatment of Grignard reagent. Deuterated TG (dTG) was hydrolyzed partially to a mixture of deuterated diacylglycerols (dDG), which were subsequently reacted with (S)-(+)-1-(1-naphthyl)ethyl isocyanate to derivatize into dDG-NEUs. Purified dDG-NEUs were resolved into 1, 3-, 1, 2- and 2, 3-dDG-NEU on silica columns in tandem of HPLC using a solvent of 0.4% propan-1-o1 (containing 2% water)-hexane. An aliquot of each dDG-NEU fraction was hydrolyzed and (fatty acid-PFB ester). These derivatives showed a diagnostic carboxylate ion, (M-1)-, as parent peak and a minor peak at m/z 196 (PFB-CH3)- on NICI mass spectra. In the mass spectra of the fatty acid-PFB esters of dTGs derived from the seed oils of T. kilirowii and M. charantia, peaks at m/z 285, 287, 289 and 317 were observed, which corresponded to (M-1)- of deuterized oleic acid (d2-C18:0), linoleic acid (d4-C18:0), punicic acid (d6-C18:0) and eicosamonoenoic acid (d2-C20:0), respectively. Fatty acid compositions of deuterized total TG of each oil measured by relative intensities of (M-1)- ion peaks were similar with those of intact TG of the oils by GLC. The composition of fatty acid-PFB esters of total dTG derived from the seed oils of T. kilirowii are as follows; C16:0, 4.6 mole % (4.8 mole %, intact TG by GLC), C18:0, 3.0 mole % (3.1 mole %), d2C18:0, 11.9 mole % (12.5 mole %, sum of C18:1Ω9 and C18:1Ω7), d4-C18:0, 39.3 mole % (38.9 mole %, sum of C18:2Ω6 and its isomer), d6-C18:0, 41.1 mole % (40.5 mole %, sum of C18:3 9c,11t,13c, C18:3 9c,11t,13r and C18:3 9t,11t,13c), d2-C20:0, 0.1 mole % (0.2 mole % of C20:1Ω9). In total dTG derived from the seed oils of M. charantia, the fatty acid components are C16:0, 1.5 mole % (1.8 mole %, intact TG by GLC), C18:0, 12.0 mole % (12.3 mole %), d2-C18:0, 16.9 mole % (17.4 mole %, sum of C18:1Ω9), d4-C18:0, 11.0 mole % (10.6 mole %, sum of C18:2Ω6), d6-C18:0, 58.6 mole % (57.5 mole %, sum of C18:3 9c,11t,13t and C18:3 9c,11t,13c). In the case of Aleurites fordii, C16:0; 2.2 mole % (2.4 mole %, intact TG by GLC), C18:0; 1.7 mole % (1.7 mole %), d2-C18:0; 5.5 mole % (5.4 mole %, sum of C18:1Ω9), d4-C18:0 ; 8.3 mole % (8.5 mole %, sum of C18:2Ω6), d6-C18:0; 82.0 mole % (81.2 mole %, sum of C18:3 9c,11t,13t and C18:3 9c,11t,13c). In the stereospecific analysis of fatty acid distribution in the TG species of the seed oils of T. kilirowii, C18:3 9c,11t,13r and C18:2Ω6 were mainly located at sn-2 and sn-3 position, while saturated acids were usually present at sn-1 position. And the major molecular species of (C18:2Ω6)(C18:3 9c,11t,13c)2 and (C18:1Ω9)(C18:2Ω6)(C18:3 9c,11t,13c) were predominantly composed of the stereoisomer of sn-1-C18:2Ω6, <..

Conjugate trienoic acids (CTA) occurred in triacylglycerols (TGs) of the seed oils of Trichosanthes kirilowii, Momordica charantia and Aleurites fordii, and they were easily converted to their methyl esters in a mixture of sodium methoxide-methanol without any structural destruction. The main fatty acids in triacylglycerol (TG) fraction of the seed oils of Trichosanthes kirilowii are C18:2Ω6 (32.2 mol %), C18:3 9c.11t,13c (38.0 mol %) and C18:1Ω9 (11.8 mol %), followed with C16:0 (4.8 mol %) and C18:0 (3.1 mol %). The TG fraction was resolved into 20 TG molecular species according to the partition number (PN) by reversed-phase (RP)-HPLC. The main TG species were DTc2, MDTc and D2Tc, of which amounts reached 63 mol % of total TG molecular species. The TG sample was fractionated into 11 fractions according to the number of double bond in the molecule by Ag+-HPLC and the species of DTc2, MDTc and D2Tc were also eluted as main components. The TG species containing CTA showed unusual behaviours in the order of elution by HPLC ; first, TG moleular species of DTc2 (D; dienoic acid, Tc; punicic acid, Tci; α-eleostearic acid, M ; monoenoic acid, St; stearic acid) was eluted earlier than Mtc2, although they have the same PN number of 40, and, secondly, the species of DTci2 with eight double bonds was eluted earlier than that of D2Tci with seven double bonds. Intact TG of the seed oils of Momordica charantia contained mainly fatty acids such as C18:3Ω9c,11t,13t (57.7 mol %), C18:1Ω9 (17.4 mol %), C18:0 (12.3 mol %) and C18:2Ω6 (10.6 mol %), and was classified into 13 fractions by RP-HPLC. The main TG species were as follows ; MTci2 [(C18:1Ω9)(C18:3 9c,11t,13t)2, 39.1 mol %] and StTci2 [(C18:0)(C18:3 9c,11t,13t)2, 33.9 mol %] comprising about 73 mol % of total TG species, accompanied by DTci2 [(C18:2Ω6)(C18:3 9c,11t,13t)2, 7.3 mol %], D2Tci [ (C18:2Ω6)2(C18:3 9c,11t,13t), 3.6 mol %] and MDTci [(C18:1Ω9)(C18:2Ω6)(C18:3 9c,11t,13t), 3.5 mol %]. Simple TG species of Tci3 [(C18:3 9c,11t,13t)3] was present in a small amount of 1.4 mol %, but other simple TG species were not detected. The TG was also resolved into 11 fractions according to the number of double bond by Ag+-HPLC, and the species were mainly occupied by MTci2 [(C18:1Ω9)(C18:3 9c,11t,13t)2, 39.4 mol %] and StT-ci2 [(C18:0)(C18:3 9c,11t,13t)2, 35.4 mol %] DTci2 species with eight double bonds was also developed faster than D2Tci one with seven double bonds as indicated in the analysis of TG of the seed oils of T. kirilowii, and MTci2 species with cis, trans, trans-configurated double bond was eluted earlier than MTc2 species with cis, trans, cis-configurated double bond. The main components of fatty acid in total TG fraction isolated from the seed oils of of Aleurites fordii were in the following order ; C18:3 9c,11t,13t (81.2 mol %)〉 C18:2Ω6 (8.5 mol %)〉 C18:1Ω9 (5.4 mol %). With resolution of the TG by RP-HPLC, eight fractions such as Tci3, Dtci2, D2Tci, MTci2, PTci2 (P; palmi..

In search for several fatty acid with unusual structure in vegetable oils, we have found that unknown peaks were shown on GLC in the analysis of fatty acids of the lipids from the pulp of ripened jujube (Zizypus jujuba var. inermis) fruits. These fatty acids were identified as a series of cis-monoenoic acids with Ω-5 double bond system such as C14:1Ω5, C16:1Ω5 and C18:1Ω5, including Ω-7 fatty acid as C16:1Ω7 and C18:1Ω7, by GLC, solid-phase extraction silver ion-column chromatographic, GLC-mass spectrometric and IR techniques. First of all, total fatty acid methyl esters were resolved into saturated and branched fatty acid, monoenoic acid, dienoic acid, and trienoic acid fraction, respectively, with 100% dichloromethane (DCM), DCM/acetone (9:1, v/v) 100% acetone, and acetone/ acetonitrile (97:3, v/v) solvent system. Unknown fatty acids were included in the monoenoic fraction and were confirmed to have cis-configuration by IR. Picolinyl esters of monoenoic fatty acids gave distinct molecular ion peak and dominant diagnostic peaks, for example, m/z 317, 220 and 260 fragment for cis-C14:1Ω5, m/z 345, m/z 248 and 288 fragment for cis-C16:1Ω5 and m/z 373, m/z 276 and 316 fragment for cis-C18:1Ω5. In this way the occurrence of cis-C16:1Ω7 and cis-C18:1Ω7 could be deduced from the appearance of prominent fragments as m/z 345, 220 and 260, and m/z 373, 248 and 280. Level of total Ω-5 fatty acids amounted to about 30% in the fatty acid composition with the predominance of C16:1Ω5 (18.7~25.0%), in the semi-ripened and/or ripened samples collected in September 14 (C16:1Ω5 ; 18.7%, C14:1Ω5 ; 3.6% and C18:1Ω5 ; 3.0%), September 22 (C16:1Ω5 ; 25.0%, C14:1Ω5 ; 1.4% and C18:1Ω5 ; 2.6%), and October 7 (C16:1Ω5 ; 24.7%, C14:1Ω5 ; 7.7% and C18:1Ω5 ; 2.5%). However, the lipids extracted from unripened jujube in July and August contain these unusual fatty acids as low as negligible. It could be observed that the level of Ω-5 fatty acids in the pulps increased sharply with an elapse of ripening time of jujube fruits. Other monoenoic fatty acids with Ω-7 series, C16:1Ω7 (palmitoleic acid) and C18:1Ω7 (cis-vaccenic acid) could be detected. And in the lipids of the kernel and leaf of jujube, none of Ω-5 fatty acids could be detected.

온실에서 재배 한 chervil (Anthricus cerefolium) 과coriander (Coriandrum sativum)의 잎, 줄기 및 종실로부터 SDE방법에 의해 향기성분을 분리한 다음 GC 및 GC-MS에 의해 향기성분을 분리·동정한 결과 49종의 성분을 확인하였다. Coriander의 경엽에서는 β-sesquiphellandrene (17.6%), germacrene B (7.7%), nerolidol (6.9%), selinene-4-ol (6.0%) 등이, Coriander의 종실로부터는 linalool, decanal (5.6%), γ-terpinene (3.8%), ρ-cymene 등이, chervil에서는 methyl chavicol. 1-allyl-2, 4-dimethoxy benzene 등이 주요 향기성분으로 나타나 주로 terpene류 들에 의해 향기성분이 발현됨을 알 수 있었다.

We checked the presence of phospholipase A2(PLA)2 which could split the ester bond at the position 2 in the glycerol backbone of glycerophospholipids, in the cells of hyperthermophiles of Pyrococcus horikoshii and Sulfolobus acidocaldarius. The results obtained are as follows; (1). Pyrococcus horikoshii cells were grown in obligate anaerobic conditions at 95℃ and they needed sulfur as energy source instead of oxygen, while Sulfolobus acidocaldarius species grew well in the aerobic medium (pH 2.5) containing yeast and sucrose at 75℃. (2). Pyrococcus horikoshii cells produced phospholipase A2 in the cell culture media although this species did not show lipase activity at least in the pH range of 1.5 ~ 3.5. Sulfolobus acidocaldarius cells produced lipase hydrolyzing triacylglycerols such as triolein, but did not split any kind of phospholipids used as substates. (3). The compound of 1-decanoyl-2-(p-nitrophenylglutaryl) phosphatidylcholine was not suitable for a substrate in this experiment, though frequently used as a subtrate for checking presence of phospholipase A2, for its decomposi-tion in this experiment. The L-α-phosphatidylcholine-β-[N-7-nitrobenz-2-oxa-1, 3-diazol]aminohexanoyl-γ-hexadecanoyl labelled with a fluorescent material, did not show any migration of acyl chains in the molecule during the reaction with phospholipase A2 under a hot condition. (4). Phospholipase A2 in the cells of Pyrococcus horikoshii, showed the optimum activity at pH6.7~7.2 and 95~105℃, respectively, and was activated by addition of calcium chloride solution. Andthe phospholipase A2 specifically hydrolyzed glycero-phospholipids such as phosphatidyl choline, phosphatidyl ethanolamine, phosphatidyl serine and phosphatidyl inositol, but could not split phospholipid containing ether bonds in the molecule such as DL -α-phosphatidylcholine-β-palmitoyl-γ-O-hexadecyl, DL-α-phosphati- dylcholine-β- oleoyl-γ-O-hexadecyl, DL-phosphatidylcholine-dihexadecyl.

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.

The lipids from the seeds of Pinus koraiensis mostly composed of triacylglycerols (TGs), in which linoleic acid (46.2 mol%) and oleic acid (25.6 mol%) are present as main components in the fatty acid composition. Surprisingly, they also have unusual fatty acids with δ5-double bond systems such as δ5.9.12-C18:3 (16.0 mol%), δ5.9-C18:2 (2.3 mol%) and δ5.11.14-C20:3 (0.8 mol%). Saturated fatty acids of palmitic, stearic and arachidic acid were present in less than 8.0 mol%. TG was resolved into 17 fractions by reverse-phase HPLC according to so-called partition number (PN) suggested by Plattner, in which TG molecules with δ5-NMDB acyl chains eluted later than did those with δ9-MDB acyl radicals. Ag+-HPLC separated the TG into 14 fractions more clearly than did those with δ9-MDB acyl radicals. Ag+-HPLC separated the TG into 14 fractions more clearly than did reverse-phase HPLC, and the complexity of δ5.9.12-C18:3 moiety with silver ion impregnated in the column bed was in the level between δ9.12.15-C18:3 (C18:3Ω3) and C18:2Ω6 (δ9.12-C18:2). In the Ag+-HPLC, it was found that the molecular species having a given-numbered double bonds widely spreaded in the acyl chains eluted earlier than those concentrated in one acyl chain. The main molecular species are (C18:2Ω6)2/δ5.9.12-C18:3 (14.8 mol%), C18:1Ω9/C18:2Ω6)2 (12.8 mol%) and C18:1Ω9/C18:2Ω6/δ5.9.12-C18:3 (10.9 mol%).

Triacylglycerols of the seeds of Ginkgo biloba have been resolved by high-performace liquid chromatography(HPLC in the silver-ion and reverse-phase modes. The fatty acids were identified by a combination of capillary gas chromatography and gas-chromatography /mass spectrometry as the methyl and /or picolinyl ester. The main components are C18:2Ω6(39.0mol%), C18:1Ω7(asclepic acid 21.5mol%), and C18:1Ω9(oleic acid, 13.8mol%). Considerable amounts of unusual acid such as C20:3δ5,11,14 (5.7mol%), C18:2δ5,9(2.8mol%), and C18:3δ5,9,12(1.6mol%), were checked. In addition, an anteiso-branched fatty acid, 14-methylhexadecanoic acid, was also present as a minor component(0.9 mol%). The triacylglycerols were separated into 17 fractions by reverse-phase HPLC, and the fractionation was achieved according to the partition numnber(PN) in which a δ5-non methylene interrupted double bond(5-NMDB) showed different behaviour from a methylene interrupted double bond in a molecule with a given cahinlength. Silver-ion HPLC exhibited excellent resolution in which fractions(23 fractions) were resolved on the basis of the number and configuration of double bonds. In this instance, the strength of interaction of a δ5-NMDB system with silver ions seemed to be weaker than a methylene interrupted double bond system. The principal triacylglycerol species are as follows ; (C18:2Ω6)2/C18:1Ω7, C18:1Ω9/C18:1Ω7/C18:2Ω6, (C18:1Ω7)2/C18:2Ω6, C16:1Ω7/C18:1Ω9/C20:3δ5,11,14, C16:1Ω7/C18:1Ω7/C20:3δ5,11,14, C18:1Ω9/C18:1Ω7/C18:2Ω6, C18:1Ω9/C18:2δ5,5/C20:3δ5,11,14, (C18:1Ω7)2/C18:2Ω6 and (C18:1Ω9)2/C18:2Ω6, while simple triacylglycerols without C18:2Ω6)3 were not present. Stereospecific analysis showed that fatty acids with δ5-NMDB system and saturated chains were predominantly located at the site of sn-3 carbon of glycerol backbones. It is evident that there is asymmetry in the distribution of fatty acids in the TG molecules of Ginkgo nut oils.

박과식물(科植物) 종실(種實)에는 총지질량(總脂質量)이 21.9~50.7%의 범위(範圍)로 비교적(比較的높았으며, 특(特)히 박, 하늘타리의 경우는 41.9%와 50.7%로 조사(調査)한 시료(試料)중에 제일 높았으며, 또 모든 시료(試料)가 약(約) 98% 이상(以上)의 중성지질(中性脂質)을 함유(含有)하고 있었다. 호박, 수세미오이, 수박, 참외, 오이 및 박종자(種子)의 총지질(總脂質)에는 리놀산(酸)의 함량(含量)이 제일(第一) 많아 56.8~84.0%이였으며, α-리놀레산(酸)의 함량(含量)은 0.0~0.6%로 매우 적었고, 올레산(酸)이 주성분(主成分)인 모노엔산(酸)과 팔미트산(酸)이 대부분(大部分)인 포화지방산(飽和脂肪酸)은 그 함량(含量)이 각각(各各) 5.7~22.2%와 9.9~20.6%로 시료(試料)에 따라 심한 차이(差異)를 보였다. 하늘타리 종자(種子)의 총지질(總脂質)에는 C18:2Ω6과 9c.11t.13c-C18:3(Punicic acid)이 40.5%와 34.9%로 주요(主要) 성분(成分)이였고, 그 다음으로 C18:1Ω9가 13.8% 함유(含有)되어 있었으며, 그러나 9c/11t.13t-C18:3(α-eleostearic acid)는 2.2%에 지나지 않았다. 한편 여주의 경우(境遇)에는 9c.11t.13c-C18:3이 66.9%로 제일(第一) 많았으며, 그 다음으로 C18:1Ω9와 C18:1Ω6이 17.7%, 10.4% 각각(各各) 함유(含有)되어 있었고, 하늘타리에 많이 함유(含有)되어 있는 9c.11t.13c-C18:3는 9t.11t.13c-C18:3(β-eleostearic acid)와 함께 1.1% 정도(程度)로 소량(少量) 포함(包含)되어 있었다. 9c.11t.13c-C18:3와 9c.11t.13t-C18:3와 같은 conugate trienoic acid는 여타시료(餘他試料)에서는 전연 검출(檢出)되지 않았다. 하늘타리와 여주의 종자유(種子油)의 극성지질(極性脂質)에는 이틀의 중성지질(中性脂質)에 다량(多量)으로 존재(存在)하는 conjugate trienoic acid가 극(極)히 소량(少量)밖에 존재(存在)하지 않는 것은 매우 특징적(特徵的)이며, 포화지방산(飽和脂肪酸)이 중성지질(中性脂質)(9.9~20.6%)에 비(比)하여 극성지질(極性脂質)(25.0~29.4%) 에 보다 많이 함유(含有)되어 있다는 사실(事實)을 나머지 시료(試料)에서 공통적(共通的)으로 찾아볼 수 있었다. 박과식물(科植物) 종자(種子)는 리놀산(酸)을 많이 함유(含有)하고 있는 군(群)과, 9c.11t.13c-C18:3 및 9c.11t.13t-C18:3와 같은 conjugate trienoic acid를 가진 군(群)으로 대별(大別)할 수 있었다.

This project has been worked out for isolation of EPA-producing bacteria from marine source of sea water, sea sediment and intestinal contents eviscerated from some red-muscle fish such as mackerel, horse-mackerel and spike fish. The samples were precultured on the media of PPES-II glucose broth and then pure-cultured on Nutrient agar and P-Y-M glucose. Lipids extracted from those bacterial mass collected by centrifugation were analysed in terms of lipid class and fatty acid composition. The results are resumed as follows : 1. 112 strains from sea water and 76 strains from sea sediment were tested for their EPA producing capability, but both strains of (SA-67 and SA-91) from the former and four strains(SS-35, 37, 51 and 71) from the latter have been proved to produce EPA above the level of 2% of total fatty acids. The strains such as GS-11, 29, 31, HM-9, 29, B-18, 33, 107, YL-129, 156, 203, 77, 104 and 256 which were isolated from fish intestinal contents, have also produced EPA at higher level than 2% of total fatty acids. 2. Contents of total lipids extracted from the cultures of these strains grown at 25℃, range from 2.8% to 6.9% (on dry weight %), and they are mainly composed of polar lipids(40.9~52.9%) such as phosphatidyl glycerol(+cardiolipin)(?) and phosphatidyl ethanolamine (33.8~40.0%), with smaller amount of free fatty acid (11.2~20.2%). 3. EPA was isolated from a mixture of fatty acid methyl esters obtained from the lipid of each strain by HPLC in silver-ion mode and was identified by GC-Mass spectrometry. 4. The strains of SW-91, GS-11, GS-29, HM-9, B-18 and YL-203 grown at 25℃ have a level of 5% EPA in their total fatty acids, and the GS-11 and HM-9 strains show a tendency of increase in the EPA level with an increase of growth temperature.

Conventional alkaline catalytic procedure, including sodium methoxide-methanol N, N, N', N'-tetramethyl guanidine-methanol, and acid-catalytic methods of BF3-methanol and HCI-methanol, have been applied for preparing methyl esters from the triacylglycerols of Trichosanthes kirilowiil seeds containing conjugated trienoic acids. The alkaline catalytic methods produce the methyl esters quantitatively without isomerization of the conjugated trienoic acids, but the acid-catalytic ones destroy almost the molecules of conjugated trienoic acids during transesterification of the triacylglycerols although the molar ratios of monoenoic and dienoic acids (non-conjugated) to saturated acids are in good agreement with those obtained from the alkaline methods.

Some seeds of the Rutaceae family, Zanthoxylum piperitum, Z. schinifolium officinalis, Poncirus trifoliata, Citrus unshin, were investigated to clarify their antioxidative components. Finely powdered samples were extracted by hexane, followed by dichioromethane and then 70% methanol in a hot bath. Its unsaponifiables containing X-and Y-tocopherol with trace amount of β-and δ-tocopherol. also showed comparatively weak activity, although the hexane fraction itself had no significant antioxidative effect on lard. Levels of total tocopherols in the samples averages 42. 24-154. 11 mg/lOOg total extractives. The dichloromethane-and 70% methanol extractives showed strong antioxidative activity, from which antioxidative substances were purified with benzene-acetone(6:5, V/V) on a silica gel column, and with a solvent mixture of acetonitrile-methanol-H2O(40:40:20, V/V/V) on a Sep-Pak C18 hydrolyzed by 5% KOH-ethanol. The recovered unsaponifiables were, then, separated on a column of high performance liquid chromatography. The unsaponifiables produced by hydrolysis of the isolates from dichloromethane extractives has epi-catechin(40.0-57.1%) and (+)-catechin〈l9.1~24.4% to total phenolic substances, on area base) as major component, accompanied by chlorogenic acid, gallic acid(?), trans-p-coumaric acid and tralls-p-ferulic acid including some unknown components, and those derived from 70% methanol extractives also comprise (+)-catechin(31.3~39.6% to total components, on area base), epi-catechin(2O.2~36.4%), trans-p-cournaric acid(8.4-15.3%) and trans-p-ferulic acid(7.7~14.1%) as predominant component with some minor coponents, but the fraction supposed to be gallic acid(?) is not present. The antioxidative activities of the phenolic components isolated in this work were in order of epi-catechin〉catechin〉chlorogenic acid〉trans-p-ferluic acid〉trans-p-coumaric acid.

Levels of sterols including δ7-dehydrogenase isolated from the tissues of marine animal products (20 species) were determined on 1.5% OV-17 columm of gas-liquid chromatography. The composition showed that the mussels and clams contained various sterols in their tissues : cholesterol, brassicasterol. 24-methylenecholesterol with some minor components such as 22-trans-norcholesta-5,22-dien-3β-ol, 22-cis-dehydrocholesterol, 22-trans-dehydrocholesterol, desmosterol, 7-dehydrocholesterol, campesterol, stigmasterol, β-sitosterol, isofucosterol, and 7-dehydrocholesterol which could be converted into vitamin D3 in the skin tissue of animal was present in the muscle of oyster, Crassostrea gigas. On the other hand, the others including gastropoda were predominantly composed of cholesterol. The minor sterols such as 24-methylenecholesterol, stigmasterol and β-sitosterol in the fish intestines are supposed to be derived from dietary plankton. Cholesterol δ7-dehydrogenase which could convert cholesterol into δ7-dehydrogenase was present in the pickles of Tricurus haumela intestine.

Contents of vitamin D3 and 25-OH-vitamin D3 in marine animal products(20 species) were determined by HPLC. The isomers of vitamin D, D2 and D3, were not clearly separated on a reversed phase, μ Bonda Pak, with 20% methanol-acetonitrile, and on a normal phase, Zorbax SIL. with 0.4% isopropanol-hexane, but 25-OH-vitamin D2 and-D3 were separated on either μ Bonda Pak with 10% methanol-acetonitrile, or on Zorbax SIL with 2.2% isopropanol-hexane, respectively. Although levels of vitamin D3 and 25-OH-vitamin D3 varied remarkably according to species, their average value(fish : l,l87sim36,007 I.U/sample 100g, mussel : 58~1,706 I.U/sample 100g, pickle: 1,208~79,358 I.U/sample 100g) was greatly higher than that of meat(80~100 I.U/sample 100g) and dairy products(400~800 I.U/sample 100g). Fatty tissues of fish and pickled fish intestines contained high level of vitamin D3 and 25-OH-vitamin D3, while the clam and mussel known to have various kinds of sterol including δ7-sterol showed very low levels of vitamin D3 and its derivative.

The fatty acid, all cis-δ5,11,14-C20:3, in the Gingko nuts oils, was isolated and, purified by urea-adduct method, silver ion silica gel chromatography and HPLC equipped with reversed phase μ-Bondapak C18 column. Its structural elucidation was conducted by IR and 1H-, 13C-NMR technique. The fatty acid composition of seed oils mainly consists of linoleic acid(37.73%), vaccenic acid(18.30%), oleic acid(15.18%), palmitic acid(3.37%), palmitoleic acid(3.37%) and δ5 NMDB fatty acids(8.50%) in which all cis-δ5,11,14-C20:2 predominates.

Levels of total lipids in the seeds of three species of the Pinaceae family were determined and their fatty acid compositions were also analyzed by a gas-chromatograph equipped with a capillary column coated with Carbowax 20M. The results are summarized as follows: Lipid contents of the seeds amounted to 56.9% in P. koraiensis, 29.9% in P. thunbergii, and 21.2% in P. rigida. In all lipids 19~20 fatty acid were detected and, surprisingly, fatty acids having δ5-non-methylene interrupted conjugate double bond such as δ5, 9-C18:2,δ5, 9, 12-C18:3 and δ5, 11, 14-C20:3 occurred in appreciable amounts. In the lipids of P. koraiensis, the main component was C18:2Ω6(45.0%), followed by C18:1Ω 9(26.9%) and δ5, 9, 12-C18:3(14.6%), and then δ5, 9-C18:2(2.2%) and δ5, 11, 14-C20:3 were also present. Levels of saturated fatty acid such as C16:0 and C18:0 were as low as 7.5%. The seed oil of P. thunbergii predominantly comprised C18:2Ω6(45.2%), and was then occupied by equal amounts δ5, 9, 12-C18:3(18.1%) and C18:1Ω9(18.1%). Its δ5, 11, 14-C20:3(5.8%) level was the highest in the samples tested. δ5, 9-C18:2(2.8%) was also detected with other minor components. In the oils from the seeds of P. rigida, C18:2Ω6 was present as a main component, accompanied by C18:1Ω9(21.6%) and δ5, 9, 12-C18:3(20.3%). The latter showed higher level than in any other samples. A minor component corresponding to δ5, 9, 12, 15-C18:4(not confirmed by GC-Mass) occurred in P. thunbergii and P. rigida.

This study was aimed to observe dose-response effects of squid liver oil enriched in n3 polyunsaturated fatty acids(n-3 PUFA) on the metabolism of streptozotocint(STZ)-induced diabetic rats. In this experiment, 24 STZ-induced diabetic male rats of Sprague Dawley strain were divided into 4 groups and fed for 4 weeks with basal diet(0%). 33%,67% and 100% squid liver oil(SLO) of total fat content, and 6 normal rats were fed with 0% SLO diet at the same time. The results obtained were as follows: 1. Rat group fed with 33% SLO diet showed the least body weight loss and changes in blood glucose, while ones of 100% SLO diet showed the highest level. 2. Serum total protein and ratio of albumin to globulin of all the groups were below the standard level, but did not show significantly different among diet groups. 3. Serum creatinine concentration of all the groups were stayed whthin normal range, but BUN were 3 to 4 times higher than normal rats. BUN concentration of rats fed with 0% and 33% SLO diet was significantly lower than those of others. 4. Total-cholesterol level of serum increased in all the groups except 33% SLO diet, but since HDL-chol, levels and TG concentration went up with an incerase of SLO in the diets, the ratio of HDL-chol. to total-chol, of rats fed with 67% and 100% SLO diet showed higher than those with 0%, and 33% SLO, and TG concentration of rats fed with 67% and 100% SLO diet decreased significantly.

Dried seeds of Camellia japonica and Thea sinensis were investigated to determine the nature of their antioxidative activity. Activity was measured by the induction period in the coupled oxidation of a substrate lard and extracts or isolates to be tested. 70% methanol and dichloromethane extracts were found to be antioxidative abilities. Their unsaponifiables revealed weak antioxidative activity, although hexane extracts did not show antioxidative effect on lard. Column chromatography for dlchloromethane extracts gave 4 fractions(only 2 fractions were potent). HPLC was used in isolating potent antioxidative components from the column fractions and the precolumn-passed methanol extracts. They were separated into 7 and 8 components, respectively. The column fractions obtained from both seeds comprised trans-p-coumaric acid. trans-p-ferulic acid and an unknown component with minor components such as chlorogenic acid and catechin. On the other hand, the most prominent components in the methanol extracts were an unidentified component. trans-pcoumaric acid, trans-p-ferulic acid, catechin and chlorogenic acid. The unknown compound isolated from the column fractions and methanol extracts was identified as epicatechin by 1H-and 13C-NMR. The antioxidative activities of these components were epicatechin 〉 catechin 〉 chlorogenic acid 〉 trans-p-ferulic acid 〉 trans-p-coumaric acid.

동백종실유(冬栢種實油)에서 컬럼크로마토그래피로 지질(脂質) 성분(成分)을 상호(相互) 분리(分離)하였다. 여기서 얻은 트리글리세리드의 일부(一部)를 취하여 알칼리로 가수분해(加水分解)하거나 또는 pancreatic lipase로 가수분해(加水分解) 하여, 트리글리세리드의 구성(構成) 지방산(脂肪酸) 또는 1, 3- 위치(位置)와 2-위치(位置)에 급합(給合) 한 지방산(脂肪酸) 조성(組成)을 조사(調査)하였다. 나머지 트리글리세리드는 16% AgNO3 TLC로 이중결합선(二重結合敾)별로 나누었으며, 이렇게 나누어진 분획(分劃)을 다시 HPLC로 PN별로 재분획(再分劃) 하였다. 여기서 얻어진 획분(劃分)들 중 PN이 같은 것은 모두 모아서 알칼리 가수분해(加水分解)로 PN의 총지방산(總脂肪酸) 조성(組成)을, pancreatic lipase로 1,3 위치(位置)에 결합선(結合敾)한 지방산(脂肪酸)의 조성(組成)을 조사(調査) 하였다. 여기서 얻어진 결과(結果)로 부터 구성(構成) 트리그리셀리드 분자종(分子種)을 산출(算出)하였더니 다음과 같은 결과(算出)를 얻었다. 1) 종실유(種實油)는 투명(透明)한 액체(液體)로 그 함량(含量)이 73.5%였으며, 그 중 트리글리세리드가 94.8%, 극성(極性) 지질(極性)이 2.0%, 탄화(炭化) 수소(水素)가 1.8%였다. 2) AgNO3-TLC로 트리글리세리드를 분획(分劃)하였더니 5개의 획분(劃分)을 얻었으며, 대부분(大部分)의 트리글리세리드가 이중(二重) 결합선(結合敾) 3~5개인 band 2와 band 3에 80% 이상 존재(存在)하였다. 3) AgNO3-TLC에서 얻은 각 획분(劃分)은 모두가 HPLC상에서 PN 46, 48 및 50으로 나누어졌으며 전체(全體) 분획(分劃)에서 PN 48이 78.13%로 제일 많았으며, 다음으로 PN 50이 12.04%였으며, PN 46이 9.83%였다. 4) 전체(全體) 트리글리세리드 분자종(分子種) 중에서 0.1mol% 이상을 차지하고 있는 분자종(分子種)이 43종(種)이었으며, OOO와 POO가 각각 39.8mol%와 25.8mol%로 제일 많았으며, 그 다음으로 OPO가 5.5 mol%, OOL가 4.8 mol%, POS가 3.9mol%, SOO가 3.5mol%. POL이 3.0mol%였다. 또 동백종실유(冬栢種實油)에 존재(存在)하는 트리글리세리드의 분자종(分子種)의 조성(組成)은 1,3-random, 2-random 분포설(分布說)에 따라 구성(分布說)되어 있었다.