JP6088872B2 - Sophorolipid powder with suppressed decomposition of lactone type sophorolipid - Google Patents
Sophorolipid powder with suppressed decomposition of lactone type sophorolipid Download PDFInfo
- Publication number
- JP6088872B2 JP6088872B2 JP2013061026A JP2013061026A JP6088872B2 JP 6088872 B2 JP6088872 B2 JP 6088872B2 JP 2013061026 A JP2013061026 A JP 2013061026A JP 2013061026 A JP2013061026 A JP 2013061026A JP 6088872 B2 JP6088872 B2 JP 6088872B2
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- Prior art keywords
- sophorolipid
- powder
- cyclodextrin
- natural
- mass
- Prior art date
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- ZTOKUMPYMPKCFX-CZNUEWPDSA-N (E)-17-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxyoctadec-9-enoic acid Chemical compound OC(=O)CCCCCCC/C=C/CCCCCCC(C)O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](COC(C)=O)O1 ZTOKUMPYMPKCFX-CZNUEWPDSA-N 0.000 title claims description 141
- 239000000843 powder Substances 0.000 title claims description 59
- 238000000354 decomposition reaction Methods 0.000 title claims description 11
- 125000000686 lactone group Chemical group 0.000 title claims 2
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
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Landscapes
- Medicinal Preparation (AREA)
Description
本発明は、ラクトン型ソホロリピッドの分解が抑制された、安定なソホロリピッド粉末及びその製造方法に関する。 The present invention relates to a stable sophorolipid powder in which decomposition of a lactone type sophorolipid is suppressed and a method for producing the same.
生物由来の界面活性剤であるバイオサーファクタントの一つとして知られるソホロリピッドは、酵母の発酵から得られる発酵産物である(非特許文献1)。前記ソホロリピッドは、例えば、グルコースなどの糖類と植物油脂などの炭素源を含む液体培地に酵母を接種し、穏和な温度、圧力条件下で通気・攪拌するだけで容易に生産される。ソホロリピッドは、その生産性及び安全性等の高さから、洗剤、医薬品、化粧品及び食品等、様々な分野での適用が試みられている(特許文献1)。 Sophorolipid, which is known as one of biosurfactants that are biologically derived surfactants, is a fermentation product obtained from yeast fermentation (Non-patent Document 1). The sophorolipid is easily produced by, for example, inoculating yeast into a liquid medium containing a sugar such as glucose and a carbon source such as vegetable oil and fat, and aeration and stirring under mild temperature and pressure conditions. Sophorolipid has been tried to be applied in various fields such as detergents, pharmaceuticals, cosmetics and foods because of its high productivity and safety (Patent Document 1).
発酵後の酵母から分離した天然型ソホロリピッドは、通常、常温で粘調な液体であり、酸型及びラクトン型の混合物として得られる。この天然型ソホロリピッドを経口で摂取した場合、例えば、腸管でのタンパク質吸収を促進する等の効果が期待できる。しかしながら、前記天然型ソホロリピッドを常温で保存すると、液中のラクトン型ソホロリピッドが分解し、組成及び液性が安定しないという問題点があり、タンパク質吸収促進効果も低下するおそれがあった。 Natural sophorolipid separated from yeast after fermentation is usually a viscous liquid at room temperature, and is obtained as a mixture of acid type and lactone type. When this natural sophorolipid is taken orally, for example, effects such as promoting protein absorption in the intestinal tract can be expected. However, when the natural sophorolipid is stored at room temperature, the lactone type sophorolipid in the liquid is decomposed and the composition and liquidity are not stable, and the protein absorption promoting effect may be reduced.
そこで、本発明者らは、安定したソホロリピッドを得るため、天然型ソホロリピッドの粉末化を試みたが、粘調なソホロリピッドを粉末化することは困難であった。また、凍結乾燥を試みても、凍結乾燥後のソホロリピッドは潮解性を示し、ラクトン型の分解も抑制されず、安定なソホロリピッド粉末は得られていなかった。 Therefore, the present inventors tried to powder natural sophorolipid in order to obtain stable sophorolipid, but it was difficult to powder viscous sophorolipid. Even when lyophilization was attempted, the sophorolipid after lyophilization showed deliquescence, the decomposition of the lactone type was not suppressed, and a stable sophorolipid powder was not obtained.
本発明は、ラクトン型ソホロリピッドを含有するソホロリピッド粉末であって、該ラクトン型ソホロリピッドの分解が抑制され、経時安定性を有するソホロリピッド粉末を提供することを目的とする。 An object of the present invention is to provide a sophorolipid powder containing a lactone type sophorolipid, the decomposition of the lactone type sophorolipid being suppressed, and having stability over time.
本発明者らは、上記課題を解決するため鋭意検討の結果、驚くべきことに、天然型ソホロリピッド含有液にシクロデキストリンを添加して乾燥を行ったところ、安定なソホロリピッド粉末が得られることを見出し、さらに検討を重ねて本発明を完成させた。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have surprisingly found that, when cyclodextrin is added to a natural sophorolipid-containing liquid and dried, a stable sophorolipid powder can be obtained. The present invention was completed through further studies.
すなわち、本発明は、以下の発明に関する。
[1]ラクトン型ソホロリピッド及びシクロデキストリンを含有することを特徴とするラクトン型ソホロリピッドの分解が抑制されたソホロリピッド粉末。
[2]前記シクロデキストリンがα−シクロデキストリン、β−シクロデキストリン及びγ−シクロデキストリンからなる群から選ばれる1以上であることを特徴とする前記[1]に記載のソホロリピッド粉末。
[3]シクロデキストリンの含有量が50質量%〜99質量%であることを特徴とする前記[1]又は[2]に記載のソホロリピッド粉末。
[4]ラクトン型ソホロリピッドの含有量が1質量%〜50質量%であることを特徴とする前記[1]〜[3]のいずれかに記載のソホロリピッド粉末。
[5]ラクトン型ソホロリピッド及びシクロデキストリンを含有する混合液を粉末化する工程を有することを特徴とするソホロリピッド粉末の製造方法。
[6]前記粉末化の工程が凍結乾燥及び噴霧乾燥であることを特徴とする前記[5]に記載のソホロリピッド粉末の製造方法。
[7]前記[1]〜[6]のいずれかに記載の粉末を含有する粉末組成物を打錠して得られることを特徴とする錠剤。
That is, the present invention relates to the following inventions.
[1] A sophorolipid powder containing lactone type sophorolipid and cyclodextrin, wherein decomposition of the lactone type sophorolipid is suppressed.
[2] The sophorolipid powder according to [1], wherein the cyclodextrin is one or more selected from the group consisting of α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin.
[3] The sophorolipid powder according to [1] or [2], wherein the content of cyclodextrin is 50% by mass to 99% by mass.
[4] The sophorolipid powder according to any one of [1] to [3], wherein the content of the lactone type sophorolipid is 1% by mass to 50% by mass.
[5] A method for producing a sophorolipid powder, comprising a step of pulverizing a mixed liquid containing a lactone type sophorolipid and cyclodextrin.
[6] The method for producing a sophorolipid powder according to [5], wherein the powdering step is freeze drying and spray drying.
[7] A tablet obtained by tableting the powder composition containing the powder according to any one of [1] to [6].
本発明のソホロリピッド粉末は、含有されるラクトン型ソホロリピッドの分解が抑制され、経時安定性を有する。さらに、本発明の粉末は、保存中の潮解が起こりにくく、固結が発生しにくいため、長期保存に適する。 In the sophorolipid powder of the present invention, decomposition of the contained lactone type sophorolipid is suppressed, and it has stability over time. Furthermore, the powder of the present invention is suitable for long-term storage because liquefaction during storage hardly occurs and caking hardly occurs.
ソホロリピッドとは、ソホロース又はヒドロキシル基が一部アセチル化したソホロースと、ヒドロキシル脂肪酸とからなる糖脂質である。なお、ソホロースとは、β1→2結合した2分子のブドウ糖からなる糖である。ヒドロキシル脂肪酸とは、ヒドロキシル基を有する脂肪酸である。また、ソホロリピッドは、ヒドロキシ脂肪酸のカルボキシル基が遊離した酸型(一般式(1))と、分子内のソホロースが結合したラクトン型(一般式(2))とに大別される。酵母の発酵によって得られるソホロリピッドには、一般式(1)と一般式(2)の混合物であり、脂肪酸鎖長(R3)が異なるもの、ソホロースの6’(R2)及び6”位(R1)がアセチル化あるいはプロトン化されたもの等、30種以上の構造同族体の集合体として得られるものがある。 Sophorolipid is a glycolipid composed of sophorose or sophorose partially hydroxylated with hydroxyl group and hydroxyl fatty acid. Sophorose is a sugar composed of two molecules of glucose linked by β1 → 2. A hydroxyl fatty acid is a fatty acid having a hydroxyl group. In addition, sophorolipid is roughly classified into an acid form (general formula (1)) in which a carboxyl group of a hydroxy fatty acid is liberated and a lactone type (general formula (2)) in which sophorose in the molecule is bound. The sophorolipid obtained by yeast fermentation is a mixture of the general formula (1) and the general formula (2), which has different fatty acid chain lengths (R 3 ), sophorose 6 ′ (R 2 ) and 6 ″ positions ( There are those obtained as an aggregate of 30 or more structural homologues such as those in which R 1 ) is acetylated or protonated.
前記一般式(1)又は(2)において、R0は水素あるいはメチル基のいずれかである。R1及びR2はそれぞれ独立して、水素又はアセチル基である。R3は飽和脂肪族炭化水素鎖又は二重結合を少なくとも一個有する不飽和脂肪族炭化水素鎖であり、一以上の置換基を有していても良い。該置換基は、本発明の効果を妨げない限り特に限定されないが、例えば、ハロゲン、水酸基、低級(C1〜6)アルキル基、ハロ低級(C1〜6)アルキル基、ヒドロキシ低級(C1〜6)アルキル基、ハロ低級(C1〜6)アルコキシ基等が挙げられる。また、R3の炭素数は、通常11〜20、好ましくは13〜17、より好ましくは14〜16である。 In the general formula (1) or (2), R 0 is either hydrogen or a methyl group. R 1 and R 2 are each independently hydrogen or an acetyl group. R 3 is a saturated aliphatic hydrocarbon chain or an unsaturated aliphatic hydrocarbon chain having at least one double bond, and may have one or more substituents. The substituent is not particularly limited as long as it does not impair the effects of the present invention, for example, halogen, hydroxyl, lower (C 1 to 6) alkyl group, a halo-lower (C 1 to 6) alkyl group, hydroxy-lower (C 1 6) alkyl group, a halo-lower (C 1 to 6) alkoxy group, and the like. The number of carbon atoms of R 3 is usually 11 to 20, preferably 13 to 17, more preferably 14 to 16.
本発明のソホロリピッド粉末は、前記一般式(2)で示されるラクトン型ソホロリピッド及びシクロデキストリンを含有することを特徴とする。前記シクロデキストリンとしては、本発明の効果を妨げない限り特に限定されないが、例えば、α−シクロデキストリン、β−シクロデキストリン、γ−シクロデキストリン及びこれらの誘導体から選ばれる1以上が用いられる。前記誘導体としては、例えば、分岐シクロデキストリン並びにメチル基、ヒドロキシプロピル基及びアセチル基等の置換基を有するシクロデキストリン等が挙げられる。前記シクロデキストリンのうち、特に、保存安定性の点から、α−シクロデキストリン、β−シクロデキストリン及びγ−シクロデキストリン等が好ましく挙げられる。 The sophorolipid powder of the present invention is characterized by containing the lactone type sophorolipid represented by the general formula (2) and cyclodextrin. The cyclodextrin is not particularly limited as long as the effects of the present invention are not hindered. For example, one or more selected from α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin and derivatives thereof are used. Examples of the derivatives include branched cyclodextrins and cyclodextrins having substituents such as a methyl group, a hydroxypropyl group, and an acetyl group. Among the cyclodextrins, α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin and the like are particularly preferable from the viewpoint of storage stability.
本発明のソホロリピッド粉末におけるシクロデキストリンの含有量は特に限定されないが、ラクトン型ソホロリピッドの分解が抑制され、かつソホロリピッドの生理活性が有効に発揮されうる等の点から、約50質量%〜99質量%であることが好ましく、約80質量%〜95質量%であることがより好ましい。また、本発明のソホロリピッド粉末におけるソホロリピッドの含有量は、潮解が生じない等、保存安定性の点から、シクロデキストリン100質量部に対し、約1質量部〜120質量部であることが好ましく、約1質量部〜80質量部であることがより好ましく、約20質量部〜80質量部であることがさらに好ましい。 Although the content of cyclodextrin in the sophorolipid powder of the present invention is not particularly limited, it is about 50% by mass to 99% by mass from the viewpoint that decomposition of the lactone type sophorolipid is suppressed and the physiological activity of the sophorolipid can be effectively exhibited. It is preferable that it is about 80 mass%-95 mass%. In addition, the content of the sophorolipid in the sophorolipid powder of the present invention is preferably about 1 part by mass to 120 parts by mass with respect to 100 parts by mass of cyclodextrin from the viewpoint of storage stability such that deliquescence does not occur. It is more preferably 1 part by mass to 80 parts by mass, and further preferably about 20 parts by mass to 80 parts by mass.
本発明のソホロリピッド粉末におけるラクトン型ソホロリピッドの含有量は、特に限定されないが、加工適正および粉末性状等から、約1質量%〜50質量%であることが好ましく、約5質量%〜20質量%であることがより好ましい。ただし、前記含有量は、ソホロリピッド粉末を製造した直後(例えば、約1時間以内)に測定したものとする。本発明のソホロリピッド粉末においては、ラクトン型ソホロリピッドの分解が抑制されており、従来品と比較して、製造時から一定時間が経過した時点でのラクトン型ソホロリピッドの残存率が高い。 The content of the lactone type sophorolipid in the sophorolipid powder of the present invention is not particularly limited, but is preferably about 1% by mass to 50% by mass, and about 5% by mass to 20% by mass from the processing suitability and powder properties. More preferably. However, the content is measured immediately after the production of the sophorolipid powder (for example, within about 1 hour). In the sophorolipid powder of the present invention, the decomposition of the lactone type sophorolipid is suppressed, and the residual rate of the lactone type sophorolipid is high when a certain time has elapsed from the time of manufacture as compared with the conventional product.
ラクトン型ソホロリピッド及びシクロデキストリンを含有する混合液を粉末化する工程を有するソホロリピッド粉末の製造方法も、本発明に包含される。前記混合液は、ラクトン型ソホロリピッドを含有するソホロリピッド含有液及びシクロデキストリンを有するものであれば特に限定されず、本発明の効果を妨げない範囲において、その余の成分を含んでいてもよい。 A method for producing a sophorolipid powder having a step of pulverizing a mixed liquid containing a lactone type sophorolipid and cyclodextrin is also included in the present invention. The liquid mixture is not particularly limited as long as it has a sophorolipid-containing liquid containing lactone type sophorolipid and cyclodextrin, and may contain other components as long as the effects of the present invention are not hindered.
前記ソホロリピッド含有液としては、本発明の効果を妨げない限り特に限定されないが、天然型ソホロリピッド含有液でもよく、天然型ソホロリピッドからラクトン型のみを分離したものであってもよいが、コスト等の面からは、天然型ソホロリピッド含有液を用いることが好ましい。ここで、天然型ソホロリピッドとは、酵母を培養して得られた培養液からソホロリピッドを含む成分を分離したものを指し、通常、酸型ソホロリピッド及びラクトン型ソホロリピッド等の混合物である。 The sophorolipid-containing liquid is not particularly limited as long as it does not interfere with the effects of the present invention, but may be a natural sophorolipid-containing liquid, or may be a product obtained by separating only a lactone type from a natural sophorolipid, but costs and the like Is preferably a natural sophorolipid-containing liquid. Here, the natural sophorolipid refers to a product obtained by separating components containing sophorolipid from a culture solution obtained by culturing yeast, and is usually a mixture of acid sophorolipid, lactone sophorolipid, and the like.
前記酵母としては、例えば、Starmerella(Candida) bombicola、C.apicola、C.petrophilum、Rhodotorula(Candia) bogoriensis、C. batistae、C.gropengiesseri、Wickerhamiella domercqiae及びYarrowia lipolytica等が挙げられ、これらの酵母を公知の方法で培養することにより、ソホロリピッドが産生される。前記酵母は、保存機関から分譲された菌株又はその継代培養によって得られた菌株であってもよい。ここで、Rhodotorula(Candia) bogoriensis NRCC9862が生産するソホロリピッドは、13−[(2’−O−β−D−glucopyranosyl−β−D−glucopyranosyl)oxy] docosanoic acid6’, 6’’−diacetateであり、アルキル基の中央のヒドロキシル基とソホロースがグリコシド結合している。このソホロリピッドは前記一般式(1)及び(2)とは異なるが、ソホロースとヒドロキシル脂肪酸から構成される点では同じであり、本発明においてはそのような化合物もソホロリピッドに包含される。 Examples of the yeast include Starmerella (Candida) bombicola, C.I. apicola, C.I. petrophilum, Rhodotorula (Candia), bogoriensis, C.I. batistae, C.I. , and so on. By culturing these yeasts by a known method, sophorolipid is produced. The yeast may be a strain distributed from a storage organization or a strain obtained by subculture thereof. Here, the sophorolipid produced by Rhodotorula (Candia) bogoriensis NRCC9862 is 13-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl) oxy] docosanoic acid 6 ', 6' The hydroxyl group at the center of the alkyl group and the sophorose are glycosidically bonded. Although this sophorolipid is different from the general formulas (1) and (2), it is the same in that it is composed of sophorose and hydroxyl fatty acid, and such compounds are also included in the sophorolipid in the present invention.
ソホロリピッド産生のための酵母の培養方法としては、例えば、高濃度の糖と疎水性の油性基質を同時に与えて培養する方法等が好ましく挙げられる。又は、これに限らず、本発明の効果を妨げない限り広く公知の方法を適用できる。前記公知の方法は、特開2002−045195号公報等に記載されたものであってもよい。具体的には、糖としてグルコース、疎水性の油性基質として脂肪酸と植物油からなる炭素源を用いて、Starmerella (Candida) bombicolaを生産酵母として培養する手法であってもよい。 As a method for culturing yeast for sophorolipid production, for example, a method of culturing by simultaneously giving a high concentration of sugar and a hydrophobic oily substrate is preferable. Alternatively, not limited to this, a widely known method can be applied as long as the effect of the present invention is not hindered. The known method may be one described in JP-A-2002-045195. Specifically, a technique may be used in which Starmerella (Candida) bombicola is cultured as a production yeast using glucose as a sugar and a carbon source comprising a fatty acid and vegetable oil as a hydrophobic oily substrate.
培地組成は、特に限定されないが、ソホロリピッドの脂肪酸部分は、与える疎水性基質の脂肪酸鎖長やその割合に依存することが知られており、ある程度の制御が可能である。疎水性基質としては、例えば、オレイン酸又はオレイン酸を高い割合で含有する脂質が好適である。そのような脂質としては、例えば、パーム油、米ぬか油、ナタネ油、オリーブ油、サフラワー油等の植物油、及び豚脂や牛脂等の動物油等が挙げられる。さらに、疎水性基質にトリグリセライドとオレイン酸の混合基質を用いれば、高い割合でオレイン酸を含むソホロリピッドを高い収量・収率で得ることが可能である。産業利用の観点からは、安定に高い収量・収率でソホロリピッドを発酵生産することが求められるが、この場合、炭素源として親水性の糖と疎水性の油脂を混合したものが好ましい。親水性基質としては、グルコースが多用される。 The medium composition is not particularly limited, but the fatty acid portion of sophorolipid is known to depend on the fatty acid chain length and the ratio of the hydrophobic substrate to be given, and can be controlled to some extent. As the hydrophobic substrate, for example, oleic acid or a lipid containing a high proportion of oleic acid is suitable. Examples of such lipids include vegetable oils such as palm oil, rice bran oil, rapeseed oil, olive oil and safflower oil, and animal oils such as pork fat and beef tallow. Furthermore, if a mixed substrate of triglyceride and oleic acid is used as the hydrophobic substrate, it is possible to obtain a sophorolipid containing oleic acid in a high ratio with a high yield and yield. From the viewpoint of industrial use, it is required to fermentatively produce sophorolipid with a stable and high yield / yield. In this case, a mixture of hydrophilic sugar and hydrophobic fat as a carbon source is preferable. Glucose is frequently used as the hydrophilic substrate.
得られた培養液から、例えば遠心分離、デカンテーション等の方法で分離後、水洗いすることにより、天然型ソホロリピッド含有液が回収される。前記培養液から天然型ソホロリピッド含有液を回収する方法は、本発明の効果を妨げない限り特に限定されず、公知の方法を用いることができる。そのような方法としては、例えば、特開2003−9896号公報等に記載されたものであってもよい。具体的には、精製プロセスでは、培養終了液中で沈殿するソホロリピッドのpHを変更することで、その水への溶解性を制御し、有機溶剤を一切使用することなく、約50%含水物として天然型ソホロリピッド粗精製物を得ることができる。 The natural sophorolipid-containing liquid is recovered from the obtained culture liquid by, for example, centrifugation, decantation, and the like, followed by washing with water. The method for recovering the natural sophorolipid-containing solution from the culture solution is not particularly limited as long as the effect of the present invention is not hindered, and a known method can be used. As such a method, for example, a method described in Japanese Patent Application Laid-Open No. 2003-9896 may be used. Specifically, in the purification process, by changing the pH of the sophorolipid that precipitates in the culture end solution, its solubility in water is controlled, so that about 50% water content can be obtained without using any organic solvent. A natural sophorolipid crude product can be obtained.
天然型ソホロリピッドからラクトン型ソホロリピッドのみを分離して用いる場合の分離方法としては、特に限定されず、例えば、クロマトグラフィー分離、再結晶法等の方法が挙げられる。 The separation method when separating and using only the lactone type sophorolipid from the natural type sophorolipid is not particularly limited, and examples thereof include chromatographic separation and recrystallization methods.
粉末化に供するための前記混合液において、ソホロリピッド(酸型及びラクトン型)の濃度は、粉末化が容易である等の点から、約0.5質量%〜50質量%であることが好ましく、約5質量%〜35質量%であることがより好ましい。シクロデキストリンの濃度は、約25質量%〜99質量%であることが好ましく、約30質量%〜70質量%であることがより好ましい。また、前記混合液の粘度は、粉末化が容易である等の点から、約5〜50mPa・Sであることが好ましく、約5〜20mPa・Sであることがより好ましい。前記濃度範囲又は粘度範囲に調節するため、前記混合液は、水、エタノール、メタノール及びグリセリン等の溶媒又は分散媒等で希釈されていてもよく、人体及び環境等に対する悪影響が低減されることから、エタノール又は精製水で希釈されることが特に好ましい。前記混合液のpHは、ラクトン型ソホロリピッドの分解抑制等の点から、pH5〜9程度に調節されることが好ましく、pH6〜8程度がより好ましく、pH6.5〜7.5程度が最も好ましい。pH調整剤は特に限定されず、炭酸水素ナトリウム等公知のpH調整剤を用いることができる。 In the mixed liquid for pulverization, the concentration of sophorolipid (acid type and lactone type) is preferably about 0.5% by mass to 50% by mass from the viewpoint of easy powdering, etc. More preferably, it is about 5 mass%-35 mass%. The concentration of cyclodextrin is preferably about 25% by mass to 99% by mass, and more preferably about 30% by mass to 70% by mass. Further, the viscosity of the mixed solution is preferably about 5 to 50 mPa · S, more preferably about 5 to 20 mPa · S, from the viewpoint of easy powdering. In order to adjust the concentration range or the viscosity range, the mixed solution may be diluted with a solvent or dispersion medium such as water, ethanol, methanol, and glycerin, because adverse effects on the human body and the environment are reduced. It is particularly preferable to dilute with ethanol or purified water. The pH of the mixed solution is preferably adjusted to about pH 5 to 9, more preferably about pH 6 to 8, and most preferably about pH 6.5 to 7.5 from the viewpoint of suppressing decomposition of the lactone type sophorolipid. A pH adjuster is not specifically limited, Well-known pH adjusters, such as sodium hydrogencarbonate, can be used.
前記混合液を粉末化する方法としては、本発明の効果を妨げない限り特に限定されず、例えば、凍結乾燥法、再結晶法及びスプレードライ法等の公知の方法が用いられ、特に、生産の効率性の面で、凍結乾燥法及び噴霧乾燥法等が好ましく用いられ、最も好ましくは、噴霧乾燥法等である。混合液の作製から粉末化までの時間は、ラクトン型ソホロリピッドの分解を防ぐため、約2週間以内であることが好ましく、約24時間以内であることがより好ましい。 The method for pulverizing the mixed solution is not particularly limited as long as the effect of the present invention is not hindered. For example, known methods such as a freeze-drying method, a recrystallization method, and a spray-drying method are used. From the viewpoint of efficiency, freeze-drying methods, spray-drying methods, and the like are preferably used, and most preferably, spray-drying methods and the like. The time from preparation of the mixed solution to pulverization is preferably within about 2 weeks, and more preferably within about 24 hours, in order to prevent decomposition of the lactone type sophorolipid.
本発明のソホロリピッド粉末の平均粒径は、特に限定されないが、体内での吸収性等の点から、約300μm以下であることが好ましく、約200μm以下であることがより好ましい。ここで、前記平均粒径とは、ふるい分け法によって測定した粒度分布の積算重量が50重量%に到達する粒径で定義される。 The average particle size of the sophorolipid powder of the present invention is not particularly limited, but is preferably about 300 μm or less, more preferably about 200 μm or less from the viewpoint of absorbability in the body. Here, the average particle size is defined as the particle size at which the cumulative weight of the particle size distribution measured by the sieving method reaches 50% by weight.
本発明のソホロリピッド粉末は、安定性をより増すため、所望によりコーティング層を有していてもよい。前記コーティング層としては、酵母細胞壁、ヒドロキシプロピルメチルセルロース、ドロマイト、乳酸カルシウム及びクエン酸カルシウム、メタクリル酸メチルとメタクリル酸の共重合体、アクリル酸エチルとメタクリル酸の共重合体、ヒドロキシプロピルメチルセルロースフタレート、セルロースアセテートフタレート及びシェラック等から選ばれる1以上のコーティング材を有する層であることが好ましく、腸溶性を有する点から、ヒドロキシプロピルメチルセルロースフタレート、セルロースアセテートフタレート及びシェラック等が特に好ましい。前記コーティング材には、さらに可塑剤を添加してもよい。可塑剤としては、例えばトリアセチン、マクロゴール400、クエン酸トリエチル、Tween80、ヒマシ油及び中鎖脂肪酸等が用いられる。コーティング方法は特に限定されないが、簡便性等の点から、微粒子コーティング装置を用いて溶液又は分散液等を噴霧することが好ましい。前記溶液又は分散液の濃度は、本発明の効果を妨げない限り特に限定されないが、例えば、0.5%〜30%程度が好ましく、1%〜10%程度がより好ましい。溶媒又は分散媒としては、本発明の効果を妨げない限り特に限定されず、水、エタノール、及びグリセリン等が挙げられるが、溶解性の点から、エタノール等を用いることが特に好ましい。 The sophorolipid powder of the present invention may optionally have a coating layer in order to further increase the stability. Examples of the coating layer include yeast cell wall, hydroxypropyl methylcellulose, dolomite, calcium lactate and calcium citrate, a copolymer of methyl methacrylate and methacrylic acid, a copolymer of ethyl acrylate and methacrylic acid, hydroxypropyl methylcellulose phthalate, cellulose A layer having one or more coating materials selected from acetate phthalate and shellac is preferred, and hydroxypropylmethylcellulose phthalate, cellulose acetate phthalate and shellac are particularly preferred from the viewpoint of enteric properties. A plasticizer may be further added to the coating material. As the plasticizer, for example, triacetin, macrogol 400, triethyl citrate, Tween 80, castor oil, medium chain fatty acid and the like are used. The coating method is not particularly limited, but it is preferable to spray a solution or dispersion using a fine particle coating apparatus from the viewpoint of simplicity. The concentration of the solution or dispersion is not particularly limited as long as the effect of the present invention is not hindered, but is preferably about 0.5% to 30%, and more preferably about 1% to 10%. The solvent or dispersion medium is not particularly limited as long as the effect of the present invention is not hindered, and examples thereof include water, ethanol, glycerin, and the like, but ethanol is particularly preferable from the viewpoint of solubility.
本発明のソホロリピッド粉末を経口投与する場合は、散剤、顆粒剤、丸剤、錠剤及びカプセル剤等の固型製剤としてもよく、シロップ剤等の液剤としてもよいが、保存安定性の点から、散剤及び錠剤等が特に好ましく、経口摂取における簡便性、取扱いの容易性等の点から、前記粉末組成物を打錠して得られる錠剤等が最も好ましい。本発明のソホロリピッド粉末を含有する粉末組成物を打錠して得られる錠剤等も、本発明に包含される。これらの製剤を製造する場合には、その製剤形態に応じた担体又は添加剤を使用することができる。また、前記製剤には、本発明のソホロリピッド含有粉末組成物以外に、その他の有効成分が含有されていてもよい。 When orally administering the sophorolipid powder of the present invention, it may be a solid preparation such as powder, granule, pill, tablet and capsule, and may be a liquid such as syrup, but from the viewpoint of storage stability, Powders, tablets, and the like are particularly preferable, and tablets obtained by tableting the powder composition are most preferable from the viewpoints of convenience in oral intake and ease of handling. Tablets obtained by tableting a powder composition containing the sophorolipid powder of the present invention are also included in the present invention. When these preparations are produced, carriers or additives corresponding to the preparation form can be used. In addition to the sophorolipid-containing powder composition of the present invention, the formulation may contain other active ingredients.
前記担体又は添加剤としては、例えば、賦形剤(ポリアクリル酸ナトリウム、ポリアクリル酸カルシウム、カルボキシメチルセルロース、乳糖、デキストリン、コーンスターチ、結晶セルロース、白糖、塩化ナトリウム、ブドウ糖、尿素、デンプン、炭酸カルシウム、カオリン、ケイ酸及びリン酸カリウム等)、滑沢剤(ステアリン酸マグネシウム、ステアリン酸カルシウム、ショ糖脂肪酸エステル、グリセリン脂肪酸エステル、精製タルク及びポリエチレングリコール等)、崩壊剤(カルボキシメチルセルロースカルシウム、無水リン酸水素カルシウム、カルボキシメチルセルロースナトリウム、低置換度ヒドロキシプロピルセルロース、乾燥デンプン、アルギン酸ナトリウム、カンテン末、炭酸水素ナトリウム及び炭酸カルシウム等)、結合剤(ヒドロキシプロピルセルロース、アラビアゴム液、水、エタノール、プロパノール、単シロップ、ブドウ糖液、デンプン液、ゼラチン溶液、カルボキシメチルセルロース、メチルセルロース及びポリビニルピロリドン等)、溶解補助剤(アラビアゴム及びポリソルベート80等)、吸収促進剤(ラウリル硫酸ナトリウム等)、緩衝剤(リン酸緩衝液、酢酸緩衝液、ホウ酸緩衝液、炭酸緩衝液、クエン酸緩衝液及びトリス緩衝液等)、保存剤(パラオキシ安息香酸メチル、パラオキシ安息香酸エチル、パラオキシ安息香酸プロピル、パラオキシ安息香酸ブチル、クロロブタノール、ベンジルアルコール、塩化ベンザルコニウム、デヒドロ酢酸ナトリウム及びエデト酸ナトリウム等)、増粘剤(プロピレングリコール、グリセリン、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロース、ポリビニルアルコール及びポリエチレングリコール等)、安定化剤(亜硫酸水素ナトリウム、チオ硫酸ナトリウム、エデト酸ナトリウム、クエン酸ナトリウム、アスコルビン酸及びジブチルヒドロキシトルエン等)、pH調整剤(塩酸、水酸化ナトリウム、リン酸及び酢酸等)等を挙げることができる。 Examples of the carrier or additive include excipients (sodium polyacrylate, calcium polyacrylate, carboxymethylcellulose, lactose, dextrin, corn starch, crystalline cellulose, sucrose, sodium chloride, glucose, urea, starch, calcium carbonate, Kaolin, silicic acid and potassium phosphate, etc.), lubricant (magnesium stearate, calcium stearate, sucrose fatty acid ester, glycerin fatty acid ester, purified talc, polyethylene glycol, etc.), disintegrant (carboxymethylcellulose calcium, anhydrous hydrogen phosphate) Calcium, sodium carboxymethylcellulose, low-substituted hydroxypropylcellulose, dried starch, sodium alginate, agar powder, sodium bicarbonate and calcium carbonate) Compound (hydroxypropyl cellulose, gum arabic solution, water, ethanol, propanol, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethyl cellulose, methyl cellulose, polyvinyl pyrrolidone, etc.), solubilizer (gum arabic and polysorbate 80, etc.) , Absorption enhancers (such as sodium lauryl sulfate), buffers (phosphate buffer, acetate buffer, borate buffer, carbonate buffer, citrate buffer, Tris buffer, etc.), preservatives (methyl parahydroxybenzoate) , Ethyl paraoxybenzoate, propyl paraoxybenzoate, butyl paraoxybenzoate, chlorobutanol, benzyl alcohol, benzalkonium chloride, sodium dehydroacetate and sodium edetate), thickener (propylene glycol, glycerin, hydride) Xylethylcellulose, hydroxypropylcellulose, polyvinyl alcohol, polyethylene glycol, etc.), stabilizers (sodium bisulfite, sodium thiosulfate, sodium edetate, sodium citrate, ascorbic acid, dibutylhydroxytoluene, etc.), pH adjusters (hydrochloric acid, Sodium hydroxide, phosphoric acid, acetic acid, etc.).
(製造例1)
培養培地として、1L当たり、グルコース10g(日本食品化工社製、製品名:日食含水結晶ブドウ糖)、ペプトン5g(オリエンタル酵母社製)、酵母エキス3g(アサヒフードアンドヘルスケア社製、製品名:ミーストパウダーN)、麦芽エキス3g(日本バイオコン社製、製品名:マルタックス10)を含有する液体培地を使用し、30℃で2日間、Candida bombicola ATCC22214を振盪培養し前培養液とした。本培養培地の組成としては、1L当たり、グルコース100g、パーム油100g(山桂産業社製)、塩化アンモニウム3g、リン酸水素カリウム1g、硫酸マグネシウム5g、酵母エキス5g、尿素1gを用いた。5L容量の発酵槽に3Lの本培養培地を仕込み、滅菌前のpHは4〜5に合わせた。仕込み量に対し0.4%植菌し、30℃、6日間通気量1vvmの条件下で発酵した。培養開始7日目後に発酵を停止させ、発酵槽から取り出した培養液を静置することで、沈降したソホロリピッドを分取し、天然型ソホロリピッド含有液(約50%含水物、製造例品1)を得た。
(Production Example 1)
As a culture medium, 10 g of glucose per liter (manufactured by Nippon Shokuhin Kako Co., Ltd., product name: eclipse-containing crystal glucose), 5 g of peptone (manufactured by Oriental Yeast Co., Ltd.), 3 g of yeast extract (manufactured by Asahi Food and Healthcare Co., Ltd., product name: Candida bombicola ATCC22214 was shaken and cultured at 30 ° C. for 2 days using a liquid medium containing Mist Powder N) and 3 g of malt extract (manufactured by Nippon Biocon Co., Ltd., product name: Maltax 10) to prepare a preculture solution. As a composition of the main culture medium, 100 g of glucose, 100 g of palm oil (manufactured by Yamagata Industrial Co., Ltd.), 3 g of ammonium chloride, 1 g of potassium hydrogen phosphate, 5 g of magnesium sulfate, 5 g of yeast extract, and 1 g of urea were used per 1 L. A 5 L fermenter was charged with 3 L of main culture medium, and the pH before sterilization was adjusted to 4-5. Inoculated 0.4% with respect to the charged amount, and fermented under conditions of 30 ° C. and 6 days aeration of 1 vvm. Fermentation was stopped 7 days after the start of the culture, and the culture solution taken out from the fermenter was left to stand, so that the settled sophorolipid was collected, and a natural sophorolipid-containing solution (approximately 50% water-containing product, production example product 1) Got.
(実施例1)
製造例1で得られた天然型ソホロリピッド含有液50gに水25gを加えて攪拌した。炭酸水素ナトリウムを加えてpHを7.0に調整し、水を加えて100gとして、中性天然型ソホロリピッド含有希釈液を得た。β−シクロデキストリン(CAVAMAX(R) W7 Food シクロケム)50gに中性天然型ソホロリピッド含有希釈液60gを添加した。よく混合した後、凍結乾燥機(タイテック製 VD-800R)を使用して凍結乾燥を行った。得られた乾燥物を乳鉢で粉砕し、目開き710μmのメッシュを通してソホロリピッド粉末を得た。
(実施例2)
製造例1で得られた天然型ソホロリピッド含有液50gに水25gを加えて攪拌した。炭酸水素ナトリウムを加えてpHを7.0に調整し、水を加えて100gとして、中性天然型ソホロリピッド含有希釈液を得た。β−シクロデキストリン(CAVAMAX(R) W7 Food シクロケム)100gに中性天然型ソホロリピッド含有希釈液120gを添加し、さらに水を220g加えて希釈した。よく攪拌した後、スプレードライヤー(坂本技研製 R-3K)を使用して噴霧乾燥を行い、ソホロリピッド粉末を得た。
Example 1
To 50 g of the natural sophorolipid-containing liquid obtained in Production Example 1, 25 g of water was added and stirred. Sodium bicarbonate was added to adjust the pH to 7.0, and water was added to 100 g to obtain a neutral natural sophorolipid-containing diluted solution. Neutral natural type sophorolipid-containing diluent 60g was added to 50g of β-cyclodextrin (CAVAMAX® W7 Food cyclochem). After mixing well, lyophilization was performed using a freeze dryer (VD-800R manufactured by Taitec Co., Ltd.). The obtained dried product was pulverized in a mortar, and sophorolipid powder was obtained through a mesh having an opening of 710 μm.
(Example 2)
To 50 g of the natural sophorolipid-containing liquid obtained in Production Example 1, 25 g of water was added and stirred. Sodium bicarbonate was added to adjust the pH to 7.0, and water was added to 100 g to obtain a neutral natural sophorolipid-containing diluted solution. To 100 g of β-cyclodextrin (CAVAMAX® W7 Food cyclochem) was added 120 g of a neutral natural sophorolipid-containing diluent, and 220 g of water was further added to dilute. After stirring well, spray drying was performed using a spray dryer (R-3K manufactured by Sakamoto Giken) to obtain a sophorolipid powder.
(実施例3)
製造例1で得られた天然型ソホロリピッド含有液50gに水25gを加えて攪拌した。炭酸水素ナトリウムを加えてpHを7.0に調整し、水を加えて100gとして、中性天然型ソホロリピッド含有希釈液を得た。α−シクロデキストリン(α−100 塩水港精糖)50gに中性天然型ソホロリピッド含有希釈液60gを添加した。よく混合した後、凍結乾燥を行った。得られた乾燥物を乳鉢で粉砕し、目開き710μmのメッシュを通してソホロリピッド粉末を得た。
(Example 3)
To 50 g of the natural sophorolipid-containing liquid obtained in Production Example 1, 25 g of water was added and stirred. Sodium bicarbonate was added to adjust the pH to 7.0, and water was added to 100 g to obtain a neutral natural sophorolipid-containing diluted solution. Neutral natural type sophorolipid-containing diluent 60 g was added to 50 g of α-cyclodextrin (α-100 saltwater refined sugar). After mixing well, lyophilization was performed. The obtained dried product was pulverized in a mortar, and sophorolipid powder was obtained through a mesh having an opening of 710 μm.
(実施例4)
製造例1で得られた天然型ソホロリピッド含有液50gに水25gを加えて攪拌した。炭酸水素ナトリウムを加えてpHを7.0に調整し、水を加えて100gとして、中性天然型ソホロリピッド含有希釈液を得た。γ−シクロデキストリン(γ−100 塩水港精糖)50gに中性天然型ソホロリピッド含有希釈液60gを添加した。よく混合した後、凍結乾燥を行った。得られた乾燥物を乳鉢で粉砕し、目開き710μmのメッシュを通してソホロリピッド粉末を得た。
Example 4
To 50 g of the natural sophorolipid-containing liquid obtained in Production Example 1, 25 g of water was added and stirred. Sodium bicarbonate was added to adjust the pH to 7.0, and water was added to 100 g to obtain a neutral natural sophorolipid-containing diluted solution. 60 g of a neutral natural sophorolipid-containing diluent was added to 50 g of γ-cyclodextrin (γ-100 saltwater port essential sugar). After mixing well, lyophilization was performed. The obtained dried product was pulverized in a mortar, and sophorolipid powder was obtained through a mesh having an opening of 710 μm.
(実施例5)
β−シクロデキストリン50gに製造例1で得られた天然型ソホロリピッド含有液30gを添加した。よく混合した後、凍結乾燥を行った。得られた乾燥物を乳鉢で粉砕し、目開き710μmのメッシュを通してソホロリピッド粉末を得た。
(Example 5)
30 g of the natural sophorolipid-containing liquid obtained in Production Example 1 was added to 50 g of β-cyclodextrin. After mixing well, lyophilization was performed. The obtained dried product was pulverized in a mortar, and sophorolipid powder was obtained through a mesh having an opening of 710 μm.
(実施例6)
実施例1で得られた天然型ソホロリピッド粉末65g、結晶セルロース(旭化成 セオラス FD101)33g及びステアリン酸カルシウム(日油製 オーラブライトCA-65)2gを混合し、自動運転による打錠を行ったところ、欠陥のない錠剤が得られた。打錠には、ロータリー式打錠機(菊水製作所 VIRGO 0512SS2AY-000-B00)を用いた。
(Example 6)
When 65 g of natural sophorolipid powder obtained in Example 1, 33 g of crystalline cellulose (Asahi Kasei Theuras FD101) and 2 g of calcium stearate (Nihon Oruralite CA-65) were mixed, tableting was performed automatically. A tablet without any was obtained. For tableting, a rotary tableting machine (Kikusui Seisakusho VIRGO 0512SS2AY-000-B00) was used.
(実施例7)
天然型ソホロリピッド粉末65gと結晶セルロース(旭化成 セオラス FD101)18g、ステアリン酸カルシウム(日油製 オーラブライトCA-65)2g及びラクトフェリン(森永乳業製 MLF-1)15gを混合し、実施例5と同様に自動運転による打錠を行ったところ、欠陥のない錠剤が得られた。
(Example 7)
65 g of natural sophorolipid powder, 18 g of crystalline cellulose (Asahi Kasei Theuras FD101), 2 g of calcium stearate (Nihon Oruralite CA-65) and 15 g of lactoferrin (MLF-1 manufactured by Morinaga Milk Industry) are mixed. When tableting was performed by driving, tablets without defects were obtained.
(比較例1)
製造例1で得られた天然型ソホロリピッド含有液50gに水25gを加えて攪拌した。炭酸水素ナトリウムを加えてpHを7.0に調整し、水を加えて100gとして、中性天然型ソホロリピッド含有希釈液を得た。中性天然型ソホロリピッド含有希釈液60gと多孔質デンプン50gを均一に攪拌後、凍結乾燥を行った。乾燥物を乳鉢で粉砕し、目開き710μmのメッシュを通してソホロリピッド粉末を得た。
(Comparative Example 1)
To 50 g of the natural sophorolipid-containing liquid obtained in Production Example 1, 25 g of water was added and stirred. Sodium bicarbonate was added to adjust the pH to 7.0, and water was added to 100 g to obtain a neutral natural sophorolipid-containing diluted solution. The neutral natural sophorolipid-containing diluted solution 60 g and porous starch 50 g were uniformly stirred and then freeze-dried. The dried product was pulverized in a mortar, and sophorolipid powder was obtained through a mesh having an opening of 710 μm.
(比較例2)
製造例1で得られた天然型ソホロリピッド含有液30gと多孔質デンプン50gを均一に攪拌後、凍結乾燥を行った。乾燥物を乳鉢で粉砕し、目開き710μmのメッシュを通してソホロリピッド粉末を得た。
(Comparative Example 2)
After 30 g of the natural sophorolipid-containing liquid obtained in Production Example 1 and 50 g of porous starch were uniformly stirred, lyophilization was performed. The dried product was pulverized in a mortar, and sophorolipid powder was obtained through a mesh having an opening of 710 μm.
(比較例3)
天然型ソホロリピッド20gを凍結乾燥した。得られた泡状乾燥物を乳鉢で破砕し、茶褐色のソホロリピッド粉末を得た。
(Comparative Example 3)
20 g of natural sophorolipid was lyophilized. The resulting foamy dried product was crushed with a mortar to obtain a brown sophorolipid powder.
(比較例4)
実施例1で得られた中性天然型ソホロリピッド含有希釈液20gを凍結乾燥した。得られた泡状乾燥物を乳鉢で破砕し、茶褐色のソホロリピッド粉末を得た。
(Comparative Example 4)
20 g of the neutral natural sophorolipid-containing diluent obtained in Example 1 was lyophilized. The resulting foamy dried product was crushed with a mortar to obtain a brown sophorolipid powder.
(比較例5)
流動層造粒装置を用いて多孔質デンプン(ロンフードOWP 日澱化学)200gに天然型ソホロリピッド(エタノールで5%天然型ソホロリピッドに希釈)を噴霧し、造粒を試みた。多孔質デンプン自体の流動性は良好であったが、噴霧直後から球状の塊が生じ、流動性が悪く造粒は困難であった。
(Comparative Example 5)
Using a fluidized bed granulator, natural sophorolipid (diluted to 5% natural sophorolipid with ethanol) was sprayed on 200 g of porous starch (Ronfood OWP Nissho Chemical) to attempt granulation. The flowability of the porous starch itself was good, but a spherical lump was formed immediately after spraying, and the flowability was poor and granulation was difficult.
(比較例6)
微粒子コーティング装置を用いて多孔質デンプンに(ロンフードOWP 日澱化学)200gに天然型ソホロリピッド(エタノールで5%天然型ソホロリピッドに希釈)を噴霧し、コーティングを試みた。微粒子コーティングユニットに粉が付着し、コーティングは困難であった。
(Comparative Example 6)
Using a fine particle coating apparatus, 200 g of porous starch (Lonfood OWP Nissho Chemical) was sprayed with natural sophorolipid (diluted to 5% natural sophorolipid with ethanol) to attempt coating. The powder adhered to the fine particle coating unit and coating was difficult.
(比較例7)
流動層造粒装置を用いてβ−シクロデキストリン(CAVAMAX(R) W7 Food シクロケム)200gに天然型ソホロリピッド(エタノールで5%天然型ソホロリピッドに希釈)を噴霧した。多孔質デンプン自体の流動性は良好であったが、噴霧直後から球状の塊が生じ、流動性が悪く造粒は困難であった。
(Comparative Example 7)
Using a fluidized bed granulator, natural sophorolipid (diluted to 5% natural sophorolipid with ethanol) was sprayed on 200 g of β-cyclodextrin (CAVAMAX® W7 Food cyclochem). The flowability of the porous starch itself was good, but a spherical lump was formed immediately after spraying, and the flowability was poor and granulation was difficult.
(比較例8)
微粒子コーティング装置を用いてβ−シクロデキストリン(CAVAMAX(R) W7 Food シクロケム)200gに天然型ソホロリピッド(エタノールで5%天然型ソホロリピッドに希釈)を噴霧した。微粒子コーティングユニットに粉が付着し、コーティングは困難であった。
(Comparative Example 8)
Using a fine particle coating apparatus, 200 g of β-cyclodextrin (CAVAMAX® W7 Food cyclochem) was sprayed with natural sophorolipid (diluted to 5% natural sophorolipid with ethanol). The powder adhered to the fine particle coating unit and coating was difficult.
(試験例1)
実施例1〜4および比較例1〜4で得られた天然型ソホロリピッド粉末を50℃、湿度45%RHで24時間放置し、粉末の固結発生状態(流動性)を確認して潮解の有無を判断した。判断基準は、710μmのメッシュを通過した場合を○(潮解なし)、メッシュ上にダマが残った場合を×(潮解あり)とした。シクロデキストリンを用いた場合、流動性が維持されており、潮解が生じていないと判断された。結果を下表に示す。
(Test Example 1)
The natural sophorolipid powders obtained in Examples 1 to 4 and Comparative Examples 1 to 4 are allowed to stand for 24 hours at 50 ° C. and a humidity of 45% RH. Judged. Judgment criteria were ◯ (no deliquescence) when passing through a 710 μm mesh, and x (with deliquescence) when lumps remained on the mesh. When cyclodextrin was used, it was judged that fluidity was maintained and deliquescence did not occur. The results are shown in the table below.
(試験例2)
実施例1、比較例1及び比較例4の粉末を、50℃で1ヶ月保存した試料を用い、ラクトン型ソホロリピッド含量の安定性について比較試験を行った。アニオン交換カラム(Nagel社Nuc−eosil100−5SB充填,φ4.6×250mm)を用いて0.2w/v% NaClO4メタノール溶液を移動相とし、HPLCを用いて天然型ソホロリピッドの含有量を比較した。検出は205nmで行った。実施例1の粉末を1ヶ月保存したものにおけるラクトン型ソホロリピッド含有量を1としたときの、他条件でのラクトン型ソホロリピッドの含有量の比を下表に示す。
(Test Example 2)
A comparative test was conducted on the stability of the lactone-type sophorolipid content using samples obtained by storing the powders of Example 1, Comparative Example 1 and Comparative Example 4 at 50 ° C. for 1 month. Using an anion exchange column (Nagel Nuc-eosil 100-5SB packed, φ4.6 × 250 mm) with 0.2 w / v% NaClO 4 methanol solution as the mobile phase, the content of natural sophorolipid was compared using HPLC. . Detection was performed at 205 nm. The following table shows the ratio of the content of the lactone type sophorolipid under other conditions when the content of the lactone type sophorolipid in the powder of Example 1 stored for 1 month is 1.
シクロデキストリンとともに粉末化した天然型ソホロリピッドの主成分であるラクトン型ソホロリピッドは、多孔質デンプンとともに粉末化した場合や天然型ソホロリピッド単独を凍結乾燥したものと比べて50℃での分解が抑制されていると考えられる。 Lactone-type sophorolipid, which is the main component of natural sophorolipid powdered with cyclodextrin, is less decomposed at 50 ° C than when powdered with porous starch or natural sophorolipid alone is freeze-dried. it is conceivable that.
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