JP4877597B2 - Oil and fat composition and method for producing the same - Google Patents
Oil and fat composition and method for producing the same Download PDFInfo
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Description
本発明は、アケビ油の1,2-ジアシルグリセロ-3-アセテートを主成分とする液状汎用型油脂組成物及びその製造方法に関する。 The present invention relates to a liquid general-purpose oil-and-fat composition mainly composed of 1,2-diacylglycero-3-acetate of akebi oil and a method for producing the same.
近年、日本人の食事は、欧米化に伴って脂質の過剰摂取が問題となっている。また、必須脂肪酸の中でもリノール酸（18:2n-6）を過剰摂取している状態であり、これが、種々の生活習慣病の原因となっていることを多くの研究者が指摘している。
日本で現在使用されている主要な食用油は、大豆油と菜種油の混合油であり、主成分はトリアシルグリセロールである。これらの油脂のトリアシルグリセロール中のリノール酸（18:2n-6）含量は約５０％を占めている。
これらの油脂中を酵素分解し、ジアシルグリセロールを主成分とする油脂組成物が開発され、食後の血中中性脂肪が上昇しにくく、体脂肪が付きにくい食用油として利用されている。また、中鎖脂肪酸が優先的にエネルギーとして利用されやすい性質を利用して、これを含有するトリアシルグリセロールを酵素を用いたエステル交換反応によって製造し、体脂肪が付きにくい性質を有する食用油が開発されている。
一方、アケビ油（アケビ科の植物であるアケビの種子から抽出した油）は、トリアシルグリセロールやジアシルグリセロール以外の物質を主成分とし、その脂肪酸組成は、一価不飽和脂肪酸であるオレイン酸（18:1）を４２．４２％含有しており、必須脂肪酸であるリノール酸（18:2n-6）は３０．５４％である。
アケビ油は、他の植物油と比較してリノール酸（18:2n-6）含量が比較的少ないので、通常の食事の脂肪酸バランスを改善できる健康に適した食用油である。
一方で、アケビ油は、もう一つの必須脂肪酸であるα-リノレン酸についても低含量である。従って、アケビ油は、α-リノレン酸含量の高いシソ油・エゴマ油など他の植物油との併用が脂肪酸組成の点で見ればより効果的である。
さらに、アケビ油は、他の植物油と比較して、飽和脂肪酸のパルミチン酸（16:0）が比較的高いという特徴を持っている。
全体として、アケビ油は、通常の食用油と比較して多価不飽和脂肪酸の割合が比較的小さく、酸化による劣化に強い食用油であることがわかった。このような性質は、繰り返し加熱させるような揚げ物の調理に用いる場合には非常に適している。
In recent years, excessive intake of lipids has become a problem in Japanese diets with the progress of Westernization. Many researchers have pointed out that linoleic acid (18: 2n-6) is excessively consumed among essential fatty acids, which causes various lifestyle-related diseases.
The main cooking oil currently used in Japan is a mixed oil of soybean oil and rapeseed oil, and the main component is triacylglycerol. The linoleic acid (18: 2n-6) content in the triacylglycerol of these fats and oils accounts for about 50%.
These fats and oils are enzymatically decomposed, and fat and oil compositions containing diacylglycerol as a main component have been developed, and are used as edible oils that are unlikely to increase blood neutral fat after meals and body fat. Further, by utilizing the property that medium-chain fatty acids are preferentially used as energy, a triacylglycerol containing this is produced by an ester exchange reaction using an enzyme, and edible oil having a property that body fat is difficult to adhere. Has been developed.
On the other hand, akebi oil (oil extracted from the seeds of the akebi family) is composed of substances other than triacylglycerol and diacylglycerol, and its fatty acid composition is oleic acid, which is a monounsaturated fatty acid ( 18: 1) is 42.42%, and the essential fatty acid linoleic acid (18: 2n-6) is 30.54%.
Akebi oil has a relatively low linoleic acid (18: 2n-6) content compared to other vegetable oils, and is therefore an edible oil suitable for health that can improve the fatty acid balance of a normal diet.
On the other hand, akebi oil has a low content of α-linolenic acid, which is another essential fatty acid. Therefore, akebi oil is more effective when used in combination with other vegetable oils such as perilla oil and sesame oil having a high α-linolenic acid content in terms of fatty acid composition.
In addition, akebi oil is characterized by a relatively high saturated fatty acid palmitic acid (16: 0) compared to other vegetable oils.
Overall, akebi oil was found to be an edible oil that has a relatively small proportion of polyunsaturated fatty acids compared to normal edible oils and is resistant to deterioration due to oxidation. Such a property is very suitable when used for cooking fried food that is repeatedly heated.
本発明は、脂質消化酵素であるリパーゼによる加水分解反応の基質となりにくく、摂取後の血中トリアシルグリセロール（中性脂肪）の増加が抑制され、体への蓄積性が少ない、かつ保存安定性及び風味が良好である、アケビ油の1,2-ジアシルグリセロ-3-アセテートを主成分とする食用油脂組成物を提供することを目的とする。 The present invention is difficult to serve as a substrate for hydrolysis reaction by lipase, a lipid digestion enzyme, suppresses an increase in blood triacylglycerol (neutral fat) after ingestion, has little accumulation in the body, and has storage stability Another object of the present invention is to provide an edible oil / fat composition having a good flavor and 1,2-diacylglycero-3-acetate of akebi oil as a main component.
本発明は、油脂中に1,2-ジアシルグリセロ-3-アセテートを５０〜１００未満％重量有する液状汎用型油脂組成物である。 The present invention is a liquid general-purpose oil / fat composition having 1,2-diacylglycero-3-acetate in an amount of 50 to less than 100% by weight.
本発明は、アケビ科植物の種子を乾燥させ、搾油もしくは溶媒抽出で、粗原油を調整し、粗原油に対し３〜２０%の水を加水し５０〜１２０℃で５〜３０分間攪拌した後、一晩静置させてビリ分及びリン脂質を主とするガム質を除去し、上清の油脂を濾過し、液状汎用型油脂組成物を製造する1,2-ジアシルグリセロ-3-アセテートを主成分とする液状汎用型油脂組成物の製造方法である。
前記製造方法により製造された液状汎用型油脂組成物をドレッシング、マヨネーズ、サプリメント、化粧品に利用したものである。
In the present invention, after drying seeds of the aceae family, adjusting crude crude oil by oil extraction or solvent extraction, adding 3-20% water to the crude crude oil, and stirring at 50-120 ° C. for 5-30
The liquid general-purpose oil / fat composition produced by the production method is used for dressing, mayonnaise, supplements, and cosmetics.
本発明は、油脂中に1,2-ジアシルグリセロ-3-アセテートを５０〜９０％重量有する液状汎用型油脂組成物であり、食後の血中中性脂肪が上昇しにくく、体脂肪が付きにくいなど肥満症の予防に有効であり、肥満症が原因となる生活習慣病の予防にも有効である。 The present invention is a liquid general-purpose oil / fat composition having 50 to 90% by weight of 1,2-diacylglycero-3-acetate in fats and oils. It is effective in preventing obesity and the like, and is also effective in preventing lifestyle-related diseases caused by obesity.
全ての天然由来の食用油は、図１に示すように、主成分（９０%以上）がトリアシルグリセロールである。また、天然由来のトリアシルグリセロールを酵素分解して生成したジアシルグリセロールを主成分とする食用油が開発されている。その他、微量成分として、食用油中にはモノアシルグリセロールや遊離脂肪酸が存在する。
図２の分析結果に示すように、アケビ油の主成分（９０%以上）はこれらとは異なった新規なもの（Unknown）であった。
なお、ほとんどの食用油は、大豆油と同様のパターンを示す。
アケビ油の脂肪酸部分は、メチルエステル誘導体化後、ガスクロマトグラフィーで分析した。
アケビ油は主に１０種類の脂肪酸で構成され、表１に示したような組成であった。
また、その他の植物油、米糠油、パーム油、オリーブ油の脂肪酸組成についても表１の右欄に示す。
As shown in FIG. 1, all natural edible oils are mainly composed of triacylglycerol (90% or more). In addition, edible oils based on diacylglycerol produced by enzymatic degradation of naturally derived triacylglycerol have been developed. In addition, monoacylglycerol and free fatty acids are present in edible oil as trace components.
As shown in the analysis result of FIG. 2, the main component (90% or more) of akebi oil was a novel (Unknown) different from these.
Most edible oils show the same pattern as soybean oil.
The fatty acid portion of akebi oil was analyzed by gas chromatography after derivatization with methyl ester.
The akebi oil was mainly composed of 10 types of fatty acids and had a composition as shown in Table 1.
The fatty acid compositions of other vegetable oils, rice bran oil, palm oil, and olive oil are also shown in the right column of Table 1.
本発明のアケビ油の有効性について、以下に説明する。
尚、例中の％は特記しない限り重量基準である。
アケビ油が食用油としての有効性の検討を行う、動物実験を行った。
４週齢のＩＣＲマウスに実験用油脂を重量比１０％添加した表２、表３、表４に示す無脂肪精製の実験飼料を与えて、１２週齢まで８週間飼育した。
実験用油脂には、上記表１に示すように、アケビ油の対照群として脂肪酸組成がアケビ油と同等になるように調製した混合油（主成分トリアシルグリセロール）を用いた。
混合油は、米糠油８１%、パーム油１５%、オリーブ油４%を混合したものである。
The effectiveness of the akebi oil of the present invention will be described below.
In the examples, “%” is based on weight unless otherwise specified.
An animal experiment was conducted to examine the effectiveness of akebi oil as an edible oil.
4 weeks old ICR mice were fed the experimental fat-free purified diets shown in Tables 2, 3 and 4 to which 10% by weight of experimental fats and oils were added, and reared for 8 weeks until 12 weeks of age.
As shown in Table 1 above, a mixed oil (main component triacylglycerol) prepared to have a fatty acid composition equivalent to that of akebi oil was used as the experimental fat / oil as shown in Table 1 above.
The mixed oil is a mixture of 81% rice bran oil, 15% palm oil, and 4% olive oil.
図３に示すグラフにマウスの体重の変化を示す。
８週間の飼育期間を通して、アケビ油マウス群の体重は混合油マウス群と比較して顕著に低かった。
１２週齢時のアケビ油マウス群の体重は４０．９０±０．９０ g、混合油マウス群は４７．４０±１．８４ gであり、アケビ油マウス群の体重が約１４％低い値であった。
図４に示すグラフに１２週齢時のマウスの肝臓と精巣上体脂肪の重量を示す。
肝臓の重量には、両マウス群間で大きな差は見られなかった。
一般に、毒性の高い脂溶性物質を摂取すると、それを処理するために肝臓が肥大することが知られている。
アケビ油マウス群の肝臓重量は対照群と差は見られなかったことから、特に肝臓毒性はないと考えられる。
一方で、精巣上体脂肪の重量は、アケビ油マウス群で０．８５±０．０９ g、混合油マウス群で２．０８±０．２０ ｇであり、アケビ油マウス群は混合油マウス群の半分以下であった。
アケビ油は混合油と比較して脂肪組織の重量が低くなることが示された。
このように、アケビ油は同じ脂肪酸組成をもつトリアシルグリセロールを摂取した場合と比較して、体脂肪がつきにくく、体重が軽くなることが分かった。
以上に結果から、アケビ油は、肥満症の予防に有効であり、肥満症が原因となる生活習慣病の予防にも有効であると考えられる。
The graph shown in FIG. 3 shows changes in the body weight of the mouse.
Throughout the 8-week breeding period, the body weight of the akebi oil mouse group was significantly lower than that of the mixed oil mouse group.
The body weight of the akebi oil mouse group at the age of 12 weeks is 40.90 ± 0.90 g, the mixed oil mouse group is 47.40 ± 1.84 g, and the weight of the akebi oil mouse group is about 14% lower. there were.
The graph shown in FIG. 4 shows the weight of mouse liver and epididymal fat at the age of 12 weeks.
There was no significant difference in liver weight between the two groups of mice.
Generally, it is known that when a highly toxic fat-soluble substance is ingested, the liver is enlarged to process it.
Since the liver weight of the akebi oil mouse group was not different from the control group, it is considered that there is no liver toxicity.
On the other hand, the weight of epididymal fat was 0.85 ± 0.09 g in the akebi oil mouse group and 2.08 ± 0.20 g in the mixed oil mouse group, and the akebi oil mouse group was the mixed oil mouse group. Less than half.
It has been shown that akebi oil has a lower weight of adipose tissue compared to mixed oil.
Thus, it was found that akebi oil is less likely to have body fat and lighter than the case of ingesting triacylglycerol having the same fatty acid composition.
From the above results, it is considered that akebi oil is effective in preventing obesity and is also effective in preventing lifestyle-related diseases caused by obesity.
次に、ラットを用いて、アケビ油の消化・吸収に関する動物実験を行った。
試料はアケビ油、アケビ油と同等な脂肪酸組成に調製した混合油（米糠油：パーム油：オリーブ油＝８１：１５：４）とし、各群９匹ずつとした。
前日の夕方から絶食状態にしたラットにアケビ油と混合油を５ g/kg（５．６ ml/kg）ゾンデで経口投与し、０（投与前）、１、２、４、６、９、１２、１５時間後に尾静脈採血を行った。
採った血液は室温で１０分放置後、卓上遠心機３５００ rpmで２０分遠心し、血清を採取した。
採取した血清を用いて、酵素法によるＴＧ（トリアシルグリセロール）の測定を行った。
試薬はトリグリセライド Eテスト ワコー（和光純薬）を用い、マイクロプレートリーダー用にスケールを変えて行った。
９６ wellプレートにスタンダードと１０倍希釈のサンプルを各１５ μlずつ入れ、発色試薬２００ μlを入れ、一分撹拌後、インキュベーターに入れ、３７℃で保温し、２０分後に５９５ nmの吸光度をマイクロプレートリーダーで測定した。
混合油とアケビ油を投与した後のラットの血中中性脂肪の濃度変化を測定した。
図５に示すように、混合油マウス群の血清中性脂肪濃度は投与してからおよそ９時間後がピークとなった。
アケビ油マウス群の血清中性脂肪濃度は投与してからおよそ４時間後がピークとなった。
それぞれのピーク時の値を比較すると、混合油マウス群はアケビ油マウス群の上昇の約１．５倍上昇しており、アケビ油の方が混合油より血清中性脂肪が上昇しにくいという結果になった。
Next, animal experiments on the digestion and absorption of akebi oil were conducted using rats.
The sample was akebi oil, and a mixed oil (rice bran oil: palm oil: olive oil = 81: 15: 4) prepared to have a fatty acid composition equivalent to that of akebi oil, and each group had 9 animals.
Rats fasted from the evening of the previous day were orally administered with 5 g / kg (5.6 ml / kg) sonde of akebi oil and mixed oil, 0 (before administration), 1, 2, 4, 6, 9, Tail vein blood was collected after 12 and 15 hours.
The collected blood was allowed to stand at room temperature for 10 minutes and then centrifuged at 3500 rpm on a tabletop centrifuge for 20 minutes to collect serum.
Using the collected serum, TG (triacylglycerol) was measured by an enzymatic method.
The reagent was triglyceride E test Wako (Wako Pure Chemical Industries), and the scale was changed for a microplate reader.
Place 15 μl of each standard and 10-fold diluted sample in 96-well plate, add 200 μl of coloring reagent, stir for 1 minute, place in incubator, keep at 37 ° C., and after 20 minutes, absorb absorbance at 595 nm in microplate Measured with a reader.
Changes in blood triglyceride concentration in rats after administration of mixed oil and akebi oil were measured.
As shown in FIG. 5, the serum triglyceride concentration of the mixed oil mouse group peaked about 9 hours after administration.
The serum triglyceride concentration in the akebi oil mouse group peaked at about 4 hours after administration.
Comparing the values at each peak, the mixed oil mouse group increased by about 1.5 times the increase of the akebi oil mouse group, and the result was that akebi oil was less likely to increase serum neutral fat than the mixed oil Became.
次に、混合油とアケビ油を投与した後のラットの血中遊離脂肪酸の濃度変化を測定した。
図６に示すように、混合油マウス群の血清遊離脂肪酸濃度は投与してからおよそ９時間にピークとなった。
アケビ油マウス群の血清遊離脂肪酸濃度は投与してからおよそ４時間後がピークとなった。
アケビ油の方が混合油より投与後６時間以降の血清遊離脂肪酸濃度が低かった。
Next, the change in the concentration of free fatty acid in blood after administration of the mixed oil and akebi oil was measured.
As shown in FIG. 6, the serum free fatty acid concentration of the mixed oil mouse group peaked at about 9 hours after administration.
The serum free fatty acid concentration in the akebi oil mouse group peaked at about 4 hours after administration.
The serum free fatty acid concentration of akebi oil after 6 hours after administration was lower than that of the mixed oil.
血清の薄層クロマトグラフィー分析をしたところ、投与したアケビ油の主成分である1,2-ジアシルグリセロ-3-アセテートは、アケビ油を投与したラットの血清からは検出されなかった。
また、ガスクロマトグラフィーによる分析もあわせて行ったところ、1,2-ジアシルグリセロ-3-アセテートは検出限界以下であった。
薄層クロマトグラフィーによる分析でも中性脂肪は混合油マウス群で高いことが確認されたが、その他の脂質には大きな差は見られなかった。
As a result of thin layer chromatography analysis of the serum, 1,2-diacylglycero-3-acetate, which is the main component of the administered akebi oil, was not detected from the serum of the rat administered with the akebi oil.
Further, when analysis by gas chromatography was also performed, 1,2-diacylglycero-3-acetate was below the detection limit.
Analysis by thin-layer chromatography also confirmed that neutral fat was high in the mixed oil mice group, but other lipids showed no significant difference.
脂質消化酵素であるリパーゼによる分解実験を行い、1,2-ジアシルグリセロ-3-アセテートとトリアシルグリセロールの加水分解を測定した。
基質は、アケビ油より精製した1,2-ジアシルグリセロ-3-アセテートまたは混合油より調整したトリアシルグリセロールを用い、基質50 mgに5％アラビアゴムを3.75 ml加え、撹拌後、10分音波処理をして基質液とした。
酵素は、リパーゼ（豚膵臓由来、30％ protein、277 U/mg protein using olive oil） を用い、100 mM N,N-Bis(2-hydroxyethyl)-2-amino-ethanesulfonic acid（BES）緩衝液で1 mg/mlに調製し、酵素液とした。
100 mＭ BES緩衝液（pH6.8、3.0％ウシ血清アルブミン、200 mＭ NaClを含む）を135 μl、蒸留水32 μl、酵素液15 μlを試験管に調製し、37℃の水浴で100rpmの振とう速度で、3分間インキュベートした後、基質液を18 μl加えた後、37℃で0、5、10、20、40分間インキュベートした。
抽出液であるクロロホルム：ヘプタン：メタノール（49:49:2）を2 ml加えて反応を停止し、10分撹拌後、2000 rpmで10分遠心分離し、上層の水相をアスピレーターで除去し、銅試薬（トリエタノールアミン1.49 g、Cu(NO3)2・3H2O 1.21 g、NaOH 0.24 gを100 ml蒸留水に溶かし、33 g NaClを加えたもの）を1 ml加えた。
さらに10分撹拌後、2000 rpmで20分遠心分離した。
上層500 μlに、発色試薬（バソクプロイン0.1 g、ブチルヒドロキシアニソール0.05 gを100 mlクロロホルムに溶かしたもの）500 μlを加え、480 nmで吸光度を測定した。
結果を定量化するために、オレイン酸を用いて、検量線の作成を行った。
オレイン酸0.0598 gに5％アラビアゴム3.5 mlを加え、撹拌後、10分音波処理して均一化し、1.0 μmolを調製後、アラビアゴムで希釈し、0 μmol、0.05 μmol、0.1 μmol、0.2 μmol、0.35 μmol、0.5 μmolを調製して基質液とした。
試験管に100 mM BES緩衝液を150 μl、蒸留水32 μlを調製し、18 μl基質液を入れた。
酵素液添加とインキュベートは行わず、以下アケビ油、混合油と同様の作業を行い、吸光度を測定した。
図７に示すように、４０分のリパーゼによる分解で、混合油はアケビ油の約１．６倍の値を示した。
このように、混合油と比較してアケビ油の方が酵素により分解されにくいことが明らかになった。
A degradation experiment using lipase, a lipid digestive enzyme, was performed, and hydrolysis of 1,2-diacylglycero-3-acetate and triacylglycerol was measured.
The substrate is 1,2-diacylglycero-3-acetate purified from akebi oil or triacylglycerol prepared from mixed oil, and 3.75 ml of 5% gum arabic is added to 50 mg of substrate. Was used as a substrate solution.
The enzyme used is lipase (derived from porcine pancreas, 30% protein, 277 U / mg protein using olive oil) in 100 mM N, N-Bis (2-hydroxyethyl) -2-amino-ethanesulfonic acid (BES) buffer. The enzyme solution was prepared to 1 mg / ml.
Prepare 135 μl of 100 mM BES buffer (containing pH 6.8, 3.0% bovine serum albumin, 200 mM NaCl), 32 μl of distilled water, and 15 μl of enzyme solution in a test tube, and shake at 100 rpm in a 37 ° C water bath. After incubating at a high speed for 3 minutes, 18 μl of substrate solution was added, followed by incubation at 37 ° C. for 0, 5, 10, 20, and 40 minutes.
The reaction was stopped by adding 2 ml of the extract chloroform: heptane: methanol (49: 49: 2), stirred for 10 minutes, centrifuged at 2000 rpm for 10 minutes, and the upper aqueous phase was removed with an aspirator. 1 ml of a copper reagent (triethanolamine 1.49 g, Cu (NO 3 ) 2 · 3H 2 O 1.21 g, NaOH 0.24 g dissolved in 100 ml distilled water and 33 g NaCl added) was added.
After further stirring for 10 minutes, the mixture was centrifuged at 2000 rpm for 20 minutes.
To 500 μl of the upper layer, 500 μl of a coloring reagent (0.1 g of bathocuproine and 0.05 g of butylhydroxyanisole dissolved in 100 ml of chloroform) was added, and the absorbance was measured at 480 nm.
In order to quantify the results, a calibration curve was prepared using oleic acid.
Add 3.5 ml of 5% gum arabic to 0.0598 g of oleic acid, stir, homogenize by sonication for 10 minutes, prepare 1.0 μmol, dilute with gum arabic, 0 μmol, 0.05 μmol, 0.1 μmol, 0.2 μmol, 0.35 μmol and 0.5 μmol were prepared as substrate solutions.
150 μl of 100 mM BES buffer and 32 μl of distilled water were prepared in a test tube, and 18 μl of the substrate solution was added.
The enzyme solution was not added and incubated, and the same procedure as that for akebi oil and mixed oil was performed, and the absorbance was measured.
As shown in FIG. 7, the mixed oil showed a value about 1.6 times that of the akebi oil after 40 minutes of lipase decomposition.
Thus, it became clear that akebi oil is less susceptible to degradation by enzymes than mixed oil.
以下に本発明の1,2-ジアシルグリセロ-3-アセテートを主成分とする液状汎用型油脂組成物の製造実施例をより詳細に説明するが、本発明はこれらの例に限定されるものではない。
アケビ科（Lardizabalaceae）の植物であるアケビ（Akebia quinata）、ミツバアケビ（Akebia tifoliata）、アケビとミツバアケビの雑種であるゴヨウアケビ（Akebia x pentaphylla）、ムベ（Stauntonia mube）の種子を無加熱による風乾、加熱もしくはマイクロウエーブ処理により乾燥させ、圧搾機による搾油もしくはヘキサンによる溶媒抽出で、粗原油を調整した。
粗原油に対し、３〜１０%の水を加水し、５０〜１２０℃で５〜３０分間攪拌した後、一晩静置させてビリ分及びリン脂質を主とするガム質を除去した。
上清の油脂を濾過し、液状汎用型油脂組成物を製造した。
尚、各油脂成分の分析は、次の方法により行った。
グリセリド組成の測定は順相カラムを装着した高速液体クロマトグラフィーにて行った。
1,2-ジアシルグリセロ-3-アセテートの構造は質量分析装置付ガスクロマトグラフィー、赤外吸収分析装置、1H-及び13C核磁気共鳴分析装置にて解析した。
脂肪酸組成の分析はメチルエステル誘導体化後、キャピラリーカラムを装着した水素炎イオン化検出機付ガスクロマトグラフィーで分析した。
The production examples of the liquid general-purpose oil / fat composition mainly comprising 1,2-diacylglycero-3-acetate of the present invention will be described in more detail below, but the present invention is not limited to these examples. Absent.
Air-dried, heated or heated seeds of Akebia quinata, Akebia tifoliata, Akebia x pentaphylla, and Stuntonia mube, which are hybrids of Lardizabalaceae The crude oil was dried by microwave treatment, and crude crude oil was prepared by oil extraction with a press or solvent extraction with hexane.
3-10% of water was added to the crude crude oil, and the mixture was stirred at 50 to 120 ° C. for 5 to 30 minutes, and then allowed to stand overnight to remove gums mainly composed of bili and phospholipid.
The supernatant oil was filtered to produce a liquid general-purpose oil composition.
In addition, the analysis of each fats and oils component was performed by the following method.
The glyceride composition was measured by high performance liquid chromatography equipped with a normal phase column.
The structure of 1,2-diacylglycero-3-acetate was analyzed by gas chromatography with a mass spectrometer, infrared absorption analyzer, 1 H- and 13 C nuclear magnetic resonance analyzer.
The fatty acid composition was analyzed by gas chromatography with a flame ionization detector equipped with a capillary column after derivatization of the methyl ester.
アケビ油の主成分（Unknown）をケイ酸カラムクロマトグラフィーにより精製し、マススペクトル、NMR及び赤外吸収スペクトルによる構造分析を行った結果、図８のような化学構造であることが分かった。
図９に示すように、グリセロールに脂肪酸が２本とアセチル基（酢酸）が結合した構造をしている1,2-ジアシルグリセロ-3-アセテートである。
この1,2-ジアシルグリセロ-3-アセテートを含有する液状汎用型油脂組成物をドレッシング、マヨネーズ、サプリメント、化粧品に利用するものである。
このような物質が主成分である食用油はこれまでに報告がなく、新規性が高いことが明らかとなった。
The main component (Unknown) of akebi oil was purified by silicic acid column chromatography, and as a result of structural analysis by mass spectrum, NMR and infrared absorption spectrum, it was found that the chemical structure was as shown in FIG.
As shown in FIG. 9, it is 1,2-diacylglycero-3-acetate having a structure in which two fatty acids and an acetyl group (acetic acid) are bonded to glycerol.
This liquid general-purpose oil-and-fat composition containing 1,2-diacylglycero-3-acetate is used for dressing, mayonnaise, supplements and cosmetics.
An edible oil containing such a substance as a main component has not been reported so far, and it has been clarified that it is highly novel.
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