JPH10120695A - Production of sesame lignan - Google Patents
Production of sesame lignanInfo
- Publication number
- JPH10120695A JPH10120695A JP31538796A JP31538796A JPH10120695A JP H10120695 A JPH10120695 A JP H10120695A JP 31538796 A JP31538796 A JP 31538796A JP 31538796 A JP31538796 A JP 31538796A JP H10120695 A JPH10120695 A JP H10120695A
- Authority
- JP
- Japan
- Prior art keywords
- sesame
- oil
- molecular distillation
- actions
- lignan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Compounds Of Unknown Constitution (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、ゴマリグナンの効率的
な製造法に関する。The present invention relates to an efficient method for producing sesame lignan.
【0002】[0002]
【従来技術と発明が解決すべき課題】ゴマ種子には様々
な種類のゴマリグナンが存在しており、通常、d−セサ
ミンが0.3〜0.5重量%程度含まれる外、セサモー
ル、セサモリン、セサミノール等が含有されていること
が知られている。また、ゴマ種子から搾油した未精製ゴ
マ油にはゴマリグナンとしてd−セサミンが0.5〜
1.0重量%程度も含有されている。さらに、硫酸等の
鉱酸、活性白土等で処理した未精製ゴマ油には、セサミ
ン類として、d−セサミンの外にd−セサミンの光学的
転位生成物であるエピセミン等が含有されている。これ
ら、セサミン類を主成分とするゴマリグナンには、コレ
ステロール低下作用、悪酔防止作用等の多様な生理活性
が知られており、健康食品としての有用性が大いに期待
されている。従来、ゴマリグナンの製造法としては、ゴ
マ油をメタノール等のアルコール、アセトン、石油エー
テル及びアセトニトリル等の有機溶媒、またはそれらと
水との混合溶媒を用いて抽出する方法が提案されてい
る。しかし、この従来法には以下の問題点があった。
1)抽出物にセサミン類以外のグリセライド等が相当量
含有され、最終製品中のセサミン含有率が低い(約1%
程度);2)多量の有機溶媒を必要とする:3)有機溶
媒の留去に要するエネルギーコストが大きい;4)残存
溶媒により、食品衛生上、食用に不適である;5)セサ
ミン回収率が低い。2. Description of the Related Art Various kinds of sesame lignans are present in sesame seeds, and usually contain about 0.3 to 0.5% by weight of d-sesamin, as well as sesamol, sesamolin, It is known that sesaminol and the like are contained. Unrefined sesame oil squeezed from sesame seeds contains 0.5-0.5% of d-sesamin as sesame lignan.
It also contains about 1.0% by weight. Furthermore, unrefined sesame oil treated with a mineral acid such as sulfuric acid, activated clay, and the like contains episesmin, which is an optical rearrangement product of d-sesamin, as sesamin, in addition to d-sesamin. These sesame lignans, which are mainly composed of sesamin compounds, are known to have various physiological activities such as a cholesterol-lowering effect and a sickness-preventing effect, and are expected to be useful as health foods. Conventionally, as a method for producing sesame lignan, a method has been proposed in which sesame oil is extracted using an alcohol such as methanol, an organic solvent such as acetone, petroleum ether and acetonitrile, or a mixed solvent of these and water. However, this conventional method has the following problems.
1) The extract contains a considerable amount of glycerides other than sesamin, etc., and the sesamin content in the final product is low (about 1%
2) requires a large amount of organic solvent: 3) requires a large energy cost for distilling off the organic solvent; 4) is unsuitable for food hygiene and edible due to the residual solvent; Low.
【0003】[0003]
【課題を解決するための手段】本発明は、ゴマ油を分子
蒸留に供することを特徴とするゴマリグナンの製造法を
提供するものである。本発明方法によれば、ゴマ油を直
接分子蒸留するだけで、セサミンを高濃度に含有するゴ
マリグナンを効率よく得ることができる。しかも、有機
溶媒抽出に伴う、溶媒可溶性のグリセライド等の混入を
回避し、かつ安全性の高い製品を得ることができるの
で、従来法の課題を悉く解決することができる。SUMMARY OF THE INVENTION The present invention provides a method for producing sesame lignan, which comprises subjecting sesame oil to molecular distillation. According to the method of the present invention, sesame oil can be efficiently obtained only by direct molecular distillation of sesame oil. In addition, it is possible to avoid contamination with glyceride or the like which is soluble in a solvent due to extraction with an organic solvent and to obtain a highly safe product, so that the problems of the conventional method can be completely solved.
【0004】本発明方法には、ゴマ種子の圧搾搾油等の
公知の方法で得られるゴマ油を使用しうる。分子蒸留
は、公知の分子蒸留機を用いて行えばよい。具体例とし
て流下薄膜式分子蒸留機や遠心式分子蒸留機が挙げられ
る。分子蒸留の条件としては、ゴマ油からのゴマリグナ
ンの蒸留に適した条件であれば、任意であるが、好まし
くは油の温度を150〜270℃、より好ましくは18
0〜250℃とし、真空度を0.1torr以下、より
好ましくは0.008torr以下で行うと、セサミン
類の回収率は80%以上と向上し、セサミン含有率が3
重量%以上、約10重量%にも達する、高濃度のセサミ
ンを含有するゴマリグナンを含む留分を効率よく得るこ
とができる。このようにして得られた留分はそのまま、
或いはサフラワー油等の食用油を配合してソフトカプセ
ル類にし、健康食品に利用しうる。また、セサミンに富
む油としてドレッシングやマヨネーズ等の一般食品にも
利用可能である。さらに、上記の留分は、所望によりエ
タノール等の適当な溶媒から結晶化させて精製してもよ
い。そのようにして得られる結晶は適当な賦形剤や担
体、添加物と一緒に、打錠するか、顆粒に成形し、同じ
く健康食品として利用しうる。特に、結晶形のゴマリグ
ナンはクッキーやキャンディー等の菓子類や、パン、振
りかけ、練り製品に配合するのに好適である。[0004] In the method of the present invention, sesame oil obtained by a known method such as squeezing and pressing of sesame seeds can be used. The molecular distillation may be performed using a known molecular distillation machine. Specific examples include a falling film molecular distillation machine and a centrifugal molecular distillation machine. The conditions for the molecular distillation are arbitrary as long as the conditions are suitable for the distillation of sesame lignan from sesame oil, but the oil temperature is preferably 150 to 270 ° C., more preferably 18 to 270 ° C.
When the temperature is 0 to 250 ° C. and the degree of vacuum is 0.1 torr or less, more preferably 0.008 torr or less, the recovery of sesamin is improved to 80% or more, and the sesamin content is 3%.
It is possible to efficiently obtain a fraction containing sesame lignan containing a high concentration of sesamin, which is not less than about 10% by weight and reaches about 10% by weight. The fraction obtained in this way is
Alternatively, edible oil such as safflower oil may be blended into soft capsules to be used for health foods. It can also be used in general foods such as dressings and mayonnaise as sesamin-rich oil. Further, the above fraction may be purified by crystallization from an appropriate solvent such as ethanol, if desired. The crystals thus obtained can be tableted or formed into granules together with suitable excipients, carriers and additives, and used as health foods. In particular, the crystalline form of sesame lignan is suitable for blending into confectionery such as cookies and candies, bread, sprinkles, and paste products.
【0005】[0005]
【実施例】以下に実施例を挙げ、本発明を詳しく説明す
るが、これらは本発明を制限するものではない。実施例1 原料ゴマ油として、焙煎油(1)(196.4g)、焙
煎精製油(2)(163.4g)及び生圧搾精製油
(3)(181.2g)の各種ゴマ油を用いた。流下薄
膜式分子蒸留機を用い、フィード量0.5〜0.7g/
分、油温230℃、及び真空度0.01torr以下で
分子蒸留を行い、留分1を得た。さらにフィード量は同
一で、油温を250℃とし、0.01torr以下の真
空度で分子蒸留行い、留分2を得た。留分1、留分2及
び残渣中のセサミン類の含量を高速液体クロマトグラフ
ィーを用い、下記の条件下で測定した。 カラム:ZOLBA x SIL 4.6mmφ x
250mm 移動相:n−ヘキサン:IPA:酢酸=99:0.5:
0.5 流量:2.0ml/min 検出器:分光蛍光スペクトロモニター 測定波長:Ex(励起波長)295nm Em(蛍光波
長)330nm。 結果を表1に示す。なお、セサミン類は、セサミン及び
エピセサミンの合計で計算した。The present invention will be described in more detail with reference to the following Examples, which do not limit the present invention. Example 1 Various sesame oils of roasted oil (1) (196.4 g), refined roasted oil (2) (163.4 g) and refined raw pressed oil (3) (181.2 g) were used as raw material sesame oil. . Using a falling film molecular distillation machine, the feed amount is 0.5 to 0.7 g /
The fraction was subjected to molecular distillation at an oil temperature of 230 ° C. and a degree of vacuum of 0.01 torr or less to obtain a fraction 1. Further, the feed amount was the same, the oil temperature was set to 250 ° C., and molecular distillation was performed at a degree of vacuum of 0.01 torr or less to obtain a fraction 2. The content of sesamin in the fraction 1, the fraction 2 and the residue was measured using high performance liquid chromatography under the following conditions. Column: ZOLBA x SIL 4.6 mmφ x
250 mm mobile phase: n-hexane: IPA: acetic acid = 99: 0.5:
0.5 Flow rate: 2.0 ml / min Detector: Spectral fluorescence spectro monitor Measurement wavelength: Ex (excitation wavelength) 295 nm Em (fluorescence wavelength) 330 nm. Table 1 shows the results. In addition, sesamin was calculated by the total of sesamin and episesamin.
【0006】[0006]
【表1】 表1の結果より、留分1及び2のセサミン類含量(%)
は10%以下と低いが、セサミン類回収率はいずれも8
0%以上となっていることが分かる。本実施例では、分
子蒸留を230℃と250℃で2回行ったが、工業化に
際しては、250℃付近で一回蒸留すれば良い。また、
これら留分1及び2にはセサモールやセサモリンも多量
に含有されており、本発明方法はゴマリグナンの極めて
効率的な製造法である。[Table 1] From the results in Table 1, the sesamin content of fractions 1 and 2 (%)
Is as low as 10% or less, but the sesamin
It turns out that it is 0% or more. In the present embodiment, the molecular distillation was performed twice at 230 ° C. and 250 ° C. However, in the case of industrialization, the distillation may be performed once at around 250 ° C. Also,
These fractions 1 and 2 also contain a large amount of sesamol and sesamolin, and the method of the present invention is a very efficient method for producing sesame lignan.
【0007】実施例2 実施例1で用いた原料(3)を同様の条件下で分子蒸留
して得られる留分1を更に同一条件下で直接分子蒸留
し、得られた留分を約2倍量のエチルアルコールに溶解
して−20℃の冷凍庫に一夜放置した。次いで、結晶を
ろ別し、乾燥した。結果を表2に示す。 Example 2 A fraction 1 obtained by molecular distillation of the raw material (3) used in Example 1 under the same conditions is further subjected to direct molecular distillation under the same conditions, and the obtained fraction is reduced to about 2 It was dissolved in twice the volume of ethyl alcohol and left in a freezer at -20 ° C overnight. Then the crystals were filtered off and dried. Table 2 shows the results.
【表2】 同様にして、他の留分を結晶化することにより、セサミ
ン含量を90%以上に高めることができる。[Table 2] Similarly, by crystallizing other fractions, the sesamin content can be increased to 90% or more.
Claims (4)
するゴマリグナンの製造法。1. A method for producing sesame lignan, comprising subjecting sesame oil to molecular distillation.
空度0.1torr以下で行うことを特徴とする請求項
1記載の製造法。2. The method according to claim 1, wherein the molecular distillation is performed at a temperature of 150 to 270 ° C. and a degree of vacuum of 0.1 torr or less.
%以上である請求項1又は2記載の製造法。3. The process according to claim 1, wherein the sesame lignan has a sesamin content of 3% by weight or more.
製造されゴマリグナン。4. Sesame lignan produced by the method according to claim 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP31538796A JPH10120695A (en) | 1996-10-22 | 1996-10-22 | Production of sesame lignan |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP31538796A JPH10120695A (en) | 1996-10-22 | 1996-10-22 | Production of sesame lignan |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH10120695A true JPH10120695A (en) | 1998-05-12 |
Family
ID=18064793
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP31538796A Pending JPH10120695A (en) | 1996-10-22 | 1996-10-22 | Production of sesame lignan |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH10120695A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007037385A1 (en) | 2005-09-30 | 2007-04-05 | Suntory Limited | Method and apparatus for producing episesamin-rich composition |
KR101181556B1 (en) * | 2004-01-29 | 2012-09-10 | 제이-오일 밀스, 인코포레이티드 | Sesame oil and process for producing the same |
US9408803B2 (en) | 2006-03-31 | 2016-08-09 | Suntory Holdings Limited | Compositions containing lignan-class compounds |
-
1996
- 1996-10-22 JP JP31538796A patent/JPH10120695A/en active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101181556B1 (en) * | 2004-01-29 | 2012-09-10 | 제이-오일 밀스, 인코포레이티드 | Sesame oil and process for producing the same |
WO2007037385A1 (en) | 2005-09-30 | 2007-04-05 | Suntory Limited | Method and apparatus for producing episesamin-rich composition |
US7943663B2 (en) | 2005-09-30 | 2011-05-17 | Suntory Holdings Limited | Process and an apparatus for producing episesamin-rich compositions |
US9408803B2 (en) | 2006-03-31 | 2016-08-09 | Suntory Holdings Limited | Compositions containing lignan-class compounds |
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