JP2010037282A - Antibacterial agent and antibacterial method - Google Patents
Antibacterial agent and antibacterial method Download PDFInfo
- Publication number
- JP2010037282A JP2010037282A JP2008202907A JP2008202907A JP2010037282A JP 2010037282 A JP2010037282 A JP 2010037282A JP 2008202907 A JP2008202907 A JP 2008202907A JP 2008202907 A JP2008202907 A JP 2008202907A JP 2010037282 A JP2010037282 A JP 2010037282A
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- Prior art keywords
- extract
- antibacterial agent
- antibacterial
- genus
- acid
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Landscapes
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Abstract
Description
本発明は、抗菌剤及び抗菌方法に関し、さらに詳しくは、ベータ酸含有ホップ抽出物とシソ科植物抽出物とを含有する抗菌剤及びそれを用いる抗菌方法に関する。 The present invention relates to an antibacterial agent and an antibacterial method, and more particularly to an antibacterial agent containing a beta acid-containing hop extract and a Labiatae plant extract and an antibacterial method using the same.
最近の研究から、リステリア種（Listeria）、特にリステリア・モノシトジェネス（Listeria monocytogenes）によって起こされるヒトでのリステリア症は、様々な種類の食品、特にソフトチーズ及びパテ並びにハム及び他のプレパッケージ食用獣肉及び鳥肉製品の摂取に関連することが明らかにされている（例えば、PHLS食品チェーンの１６の公衆衛生研究所での調査（非特許文献１）参照）。 Recent studies, Listeria species (Listeria), in particular listeriosis in humans caused by L. mono citrate monocytogenes (Listeria monocytogenes), various types of food, especially soft cheeses and pate and ham and other pre-packaged food It has been shown to be related to the consumption of animal and poultry products (see, for example, a survey of 16 public health laboratories of the PHLS food chain (Non-Patent Document 1)).
食品病原菌であるリステリア・モノシトジェネスは年間約７０例の死亡の原因となっており、これは他の食品病原菌の場合の数字の２倍を超えている。また、リステリアの主たる汚染源は食品製造者であると一般に考えられている。一方、ホップ酸及びそれらの関連酸は以前から細菌阻害剤として認識されている（特許文献１参照）。 Listeria monocytogenes, a food pathogen, causes approximately 70 deaths annually, more than twice the number for other food pathogens. In addition, it is generally considered that the main source of contamination of Listeria is food manufacturers. On the other hand, hop acids and their related acids have long been recognized as bacterial inhibitors (see Patent Document 1).
しかしながら、一般的に抗菌剤（特に天然物由来の抗菌剤）は、微生物の種類によりその抗菌活性が異なることが知られており、従来の抗菌剤は、サルモネラ菌、病原性大腸菌などに対して抗菌活性は有するものの、リステリア属の細菌などのグラム陽性菌に効果がある抗菌剤、特に食品などに添加しても安全な天然物由来の抗菌剤は余り知られていない。また、ホップ酸（特にベータ酸含有ホップ抽出物）は、リステリア菌に対する抗菌活性を有することが知られているが、特有の臭気があり、それにより使用の制限を余儀なくされていた。 However, it is generally known that antibacterial agents (especially antibacterial agents derived from natural products) have different antibacterial activities depending on the type of microorganism, and conventional antibacterial agents are antibacterial against Salmonella and pathogenic E. coli. There are few known antibacterial agents that have activity but are effective against Gram-positive bacteria such as Listeria bacteria, especially natural products that are safe to add to foods. Hop acid (especially beta acid-containing hop extract) is known to have antibacterial activity against Listeria monocytogenes, but has a peculiar odor, which inevitably limits its use.
本発明者らは、上記課題を解決するべく鋭意検討した結果、ベータ酸含有ホップ抽出物とシソ科植物抽出物とを配合して使用することにより、スタフィロコッカス属、ラクトバシルス属、リステリア属、アリシクロバシルス属、及び、バシルス属などのグラム陽性菌に対して相乗的な抗菌活性を持ち、かつホップ抽出物の特有の臭気が抑制された抗菌剤を取得できることを見出し、本発明を完成させた。 As a result of diligent studies to solve the above problems, the present inventors have combined and used a beta acid-containing hop extract and a Labiatae plant extract, so that Staphylococcus, Lactobacillus, Listeria, Discovered that an antibacterial agent having synergistic antibacterial activity against gram-positive bacteria such as Alicyclobacillus and Bacillus can be obtained, and that the odor of the hop extract is suppressed, and the present invention is completed. I let you.
即ち、本発明は、次の［１］〜［７］に記載される事項により特定される、次のとおりのものである。
［１］ベータ酸含有ホップ抽出物とシソ科植物抽出物とを含有することを特徴とする抗菌剤。
［２］シソ科植物抽出物が、非油溶性シソ科植物抽出物である、上記［１］に記載の抗菌剤。
［３］ベータ酸含有ホップ抽出物と非油溶性シソ科植物抽出物との含有割合が、成分の重量比で９９：１〜１：９９である、上記［１］又は［２］に記載の抗菌剤。
［４］臭気が抑制されたものである、上記［１］乃至［３］の何れかに記載の抗菌剤。
［５］グラム陽性菌に属する細菌に対して抗菌活性を示す、上記［１］乃至［４］の何れかに記載の抗菌剤。
［６］グラム陽性菌に属する細菌が、スタフィロコッカス（Staphyrococcus）属、ラクトバシルス（Lactobacillus）属、リステリア（Listeria）属、アリシクロバシルス（Alicyclobacillus）属、及び、バシルス（Bacillus）属から成る群より選ばれる何れかの属に属する細菌である、上記［５］に記載の抗菌剤。
［７］上記［１］乃至［６］の何れかに記載の抗菌剤を、試料中に含有させることを特徴とする抗菌方法。
That is, this invention is as follows specified by the matter described in following [1]-[7].
[1] An antibacterial agent comprising a beta acid-containing hop extract and a Labiatae plant extract.
[2] The antibacterial agent according to [1], wherein the Labiatae plant extract is a non-oil-soluble Labiatae plant extract.
[3] The content ratio of the beta acid-containing hop extract and the non-oil-soluble Lamiaceae plant extract is 99: 1 to 1:99 by weight ratio of the components, according to the above [1] or [2] Antibacterial agent.
[4] The antibacterial agent according to any one of [1] to [3], wherein the odor is suppressed.
[5] The antibacterial agent according to any one of [1] to [4], which exhibits antibacterial activity against bacteria belonging to Gram-positive bacteria.
[6] A group in which a bacterium belonging to a gram-positive bacterium comprises the genus Staphyrococcus, the genus Lactobacillus, the genus Listeria, the genus Alicyclobacillus , and the genus Bacillus The antibacterial agent according to [5] above, which is a bacterium belonging to any genus selected from the above.
[7] An antibacterial method comprising incorporating the antibacterial agent according to any one of [1] to [6] in a sample.
本発明の抗菌剤を使用することにより、試料に対して非常に少ない添加量で、スタフィロコッカス属、ラクトバシルス属、リステリア属、アリシクロバシルス属、及び、バシルス属などのグラム陽性菌、特にリステリア属に属する細菌に対して十分な抗菌効果が発揮される。本発明の抗菌剤は、ホップ抽出物の特有の臭気が抑制されているので、例えば、食品、飲料、医療、医薬品、環境安全の分野において広く使用することができるが、特に食品保存剤として有用であり、本発明の抗菌方法は、特に食品の保存方法として有用である。 By using the antibacterial agent of the present invention, Gram-positive bacteria such as Staphylococcus, Lactobacillus, Listeria, Alicyclobacillus, and A sufficient antibacterial effect is exerted against bacteria belonging to the genus Listeria. The antibacterial agent of the present invention suppresses the odor characteristic of the hop extract, so that it can be widely used, for example, in the fields of food, beverages, medicine, pharmaceuticals, and environmental safety, but is particularly useful as a food preservative. Thus, the antibacterial method of the present invention is particularly useful as a food preservation method.
以下、本発明を詳細に説明するが、この説明は本発明の実施態様の一例（代表例）であり、本発明はその要旨を超えない限り、以下の内容に限定されるものではない。 Hereinafter, the present invention will be described in detail, but this description is an example (representative example) of an embodiment of the present invention, and the present invention is not limited to the following contents unless it exceeds the gist.
本発明の抗菌剤は、ベータ酸含有ホップ抽出物とシソ科植物抽出物を有効成分として含有する。
本発明で用いられるベータ酸含有ホップ抽出物としては、ホップ抽出物であって、ルプロン、コルプロン、アルドプロン等のベータ酸を含むものであれば特に制限されず、如何なる方法で調製されたものでも良い。
The antibacterial agent of the present invention contains a beta acid-containing hop extract and a Labiatae plant extract as active ingredients.
The beta acid-containing hop extract used in the present invention is not particularly limited as long as it is a hop extract and contains a beta acid such as lupron, colpron, and aldopron, and may be prepared by any method. .
ベータ酸含有ホップ抽出物を得る方法としては、液状または臨界状態の二酸化炭素抽出による方法を採用することが望ましい。この方法は、それ自体既知の方法であり、その詳細は、特開昭６１−１３７４号公報や特開平６−２４０２８８号公報等に記載されている。この方法によれば、一般にベータ酸を５０重量％以上含有するホップ抽出物（残部はホップ樹脂やホップ精油である）を効率よく得ることができる。この方法で得られる抽出物は市販もされており、市販品としては、例えば、ステイナー社（S. S. Steiner Inc.）製のベータ・アロマ・エクストラクト（BETA AROM EXTRACT：商品名）が挙げられる。 As a method for obtaining a beta acid-containing hop extract, it is desirable to employ a method using liquid or critical carbon dioxide extraction. This method is a method known per se, and details thereof are described in JP-A-61-1374, JP-A-6-240288, and the like. According to this method, a hop extract generally containing 50% by weight or more of beta acid (the balance is hop resin or hop essential oil) can be obtained efficiently. Extracts obtained by this method are also commercially available, and examples of commercially available products include Beta AROM EXTRACT (trade name) manufactured by S. S. Steiner Inc.
なお、ベータ酸含有ホップ抽出物を得る方法は上記の方法に限定されるものではなく、例えば、熱水で抽出する方法、エタノールやアセトンや酢酸エチルなどの有機溶媒で抽出する方法、水酸化ナトリウムや炭酸ナトリウムや水酸化カリウムやリン酸ナトリウムなどのアルカリ性水溶液で抽出する方法などであってもよい。 In addition, the method for obtaining a beta acid-containing hop extract is not limited to the above-mentioned method. For example, a method of extracting with hot water, a method of extracting with an organic solvent such as ethanol, acetone, or ethyl acetate, sodium hydroxide Alternatively, a method of extracting with an alkaline aqueous solution such as sodium carbonate, potassium hydroxide or sodium phosphate may be used.
本発明で用いられるシソ科植物抽出物としては、例えばシソ、アオジソ、セージ、タイム、オレガノ、チリメンジソ、ローズマリー（マンネンロウ）等のシソ科植物の抽出物であれば、如何なる方法で調製されたものであっても良い。これらの中で、特にローズマリー抽出物が好ましい。また、本発明においては、シソ科植物抽出物としては非油溶性植物抽出物が好ましい。従って、本発明においては、シソ科植物（特にローズマリー）の非油溶性植物抽出物が最も好ましい。シソ科植物からは、各種のテルペン類が抽出される。 As a Labiatae plant extract used in the present invention, for example, an extract of a Labiatae plant such as perilla, blue mushroom, sage, thyme, oregano, chimmen diso, rosemary (mannenrou) is prepared by any method. It may be. Of these, rosemary extract is particularly preferable. Moreover, in this invention, a non-oil soluble plant extract is preferable as a Labiatae plant extract. Therefore, in the present invention, a non-oil soluble plant extract of Labiatae plant (especially rosemary) is most preferable. Various terpenes are extracted from Lamiaceae plants.
テルペン類には、モノテルペン、セスキテルペン、ジテルペン、トリテルペン等があり、具体的には、モノテルペノイドアルコール又はモノテルペノイドケトン、例えばリナロール、イソボルネオール、ボルナン−２−オン、ボルナン−２，３−ジオン、フェカン−２−オール、フェカン−２−オン、ｐ−メンタン−３−オール、ｐ−メンタン−１（６），８−ジエン−２−オ−ル、ｐ−メンタ−１，８−ジエン−７−オール、ｐ−メンタ−１−エン−８−オール、ｐ−メンタン−３−オン、ｐ−メンタ−１（６），８−ジエン−２−オン、ｐ−メンタ−１−エン−３−オン、ｐ−メンタ−４（８）−エン−３−オン、ピナ−２−エン−７−オン、ピナ−２−エン−４−オン、ツジャン−３−オン等が挙げられる。また、本発明においては、ロスマリン酸、カルノソール、カルノジック酸、ロスマノール、エピロスマノール、エピイソロスマノール、ロスマリジオール、ルテオリン等のジテルペン及びトリテルペンも好適に使用することができる。これらの中では、特に、ロスマリン酸、カルノソール又はカルノジック酸が好ましい。なお、上記のテルペノイドアルコール、テルペノイドケトン、ジテルペン、トリテルペンは合成品であってもよい。 Terpenes include monoterpenes, sesquiterpenes, diterpenes, triterpenes, etc., specifically, monoterpenoid alcohols or monoterpenoid ketones such as linalool, isoborneol, bornane-2-one, bornane-2,3-dione. , Fecan-2-ol, fecan-2-one, p-menthan-3-ol, p-menthan-1 (6), 8-dien-2-ol, p-menthan-1,8-diene- 7-ol, p-mentha-1-en-8-ol, p-menthan-3-one, p-mentha-1 (6), 8-dien-2-one, p-mentha-1-ene-3 -On, p-menta-4 (8) -en-3-one, pin-2-en-7-one, pin-2-en-4-one, tzjan-3-one and the like. In the present invention, diterpenes and triterpenes such as rosmarinic acid, carnosol, carnosic acid, rosmanol, epirosmanol, epiisorosmanol, rosmaridiol, and luteolin can also be suitably used. Among these, rosmarinic acid, carnosol or carnosic acid is particularly preferable. The terpenoid alcohol, terpenoid ketone, diterpene, and triterpene may be synthetic products.
ロスマリン酸は、フェノールカルボン酸の一つであり、特にローズマリーの中に多く含まれている。その構造は、フェノールカルボン酸が２個結合した形である。従って、構造的、機能的に、フェルラ酸、カフェ酸、クロロゲン酸などのフェノールカルボン酸より、フェノール性水酸基が多いので、酸化防止効力が高い。また、ＳＯＤ（スーパーオキシドデスムターゼ）様などの酵素阻害活性効果も高い。また、構造中に共役二重結合を有しているため、光劣化防止効力が高い。使用するロスマリン酸は、安全の観点から、天然からの抽出物が好ましく、ロスマリン酸が多量に存在するローズマリーからの抽出物が好ましい。 Rosmarinic acid is one of the phenol carboxylic acids, and is particularly contained in rosemary. The structure is a form in which two phenol carboxylic acids are bonded. Therefore, structurally and functionally, since there are more phenolic hydroxyl groups than phenol carboxylic acids, such as ferulic acid, caffeic acid, and chlorogenic acid, antioxidant effect is high. Moreover, enzyme inhibitory activity effects such as SOD (superoxide desmutase) are also high. Moreover, since it has a conjugated double bond in the structure, it has a high photodegradation prevention effect. From the viewpoint of safety, the rosmarinic acid used is preferably an extract from nature, and an extract from rosemary containing a large amount of rosmarinic acid is preferable.
ロスマリン酸の一般的な製法は次の通りである。原料としては、シソ科植物、例えばローズマリーの全草、または、その葉、根、茎、花、果実、種子の何れを使用してもよいが、好ましくは葉を使用する。通常、抽出効率を高めるため、刻んでから使用する。ロスマリン酸は、ローズマリーの水溶性（非油溶性）抽出物として得られる。従って、含水エタノールで抽出処理し、当該抽出液に水を添加して非水溶性成分を析出させ、非水溶性成分を分離した溶液を減圧濃縮することにより得られる。含水エタノールとしては含水率４０〜６０重量％のものが好適に使用される。 The general production method of rosmarinic acid is as follows. As a raw material, any of Lamiaceae plants such as whole rosemary or its leaves, roots, stems, flowers, fruits and seeds may be used, but leaves are preferably used. Usually, it is used after chopping to improve the extraction efficiency. Rosmarinic acid is obtained as a water-soluble (non-oil-soluble) extract of rosemary. Therefore, it is obtained by extracting with water-containing ethanol, adding water to the extract to precipitate a water-insoluble component, and concentrating the solution from which the water-insoluble component has been separated under reduced pressure. Water-containing ethanol having a water content of 40 to 60% by weight is preferably used.
カルノソール及びカルノジック酸は、セージ、タイム、オレガノ等のシソ科抽出物系香辛料中に多く含まれている。その構造は、他の抗酸化剤と異なり、イソプレン骨格のアピエタンの構造を有している。油脂などの酸化防止効果が他の抗酸化剤よりも格段に強い。また、構造中に共役二重結合を有しており、更に、光により生じたラジカルの影響を受けても互変異性の構造を有する為、ラジカル安定化構造をとりやすく、光劣化防止効力が高い。 Carnosol and carnosic acid are contained abundantly in spices such as sage, thyme and oregano. The structure is different from other antioxidants, and has an isoprene skeleton apietan structure. Antioxidants such as fats and oils are much stronger than other antioxidants. In addition, it has a conjugated double bond in the structure, and also has a tautomeric structure even under the influence of radicals generated by light. high.
使用するカルノソール及びカルノジック酸は、安全の観点から、天然からの抽出物が好ましい。この天然物は、セージ、タイム、オレガノ等のシソ科抽出物系の植物から抽出されるが、多量に存在する、ローズマリーからの抽出物が好ましい。 The carnosol and carnosic acid used are preferably natural extracts from the viewpoint of safety. This natural product is extracted from a plant of the Lamiaceae extract system such as sage, thyme, oregano, and an extract from rosemary which is present in a large amount is preferable.
カルノソール及びカルノジック酸は、その製法の一例は次の通りである。先ず、前述の水溶性抽出物の場合と同様に、含水エタノールで抽出し、当該抽出液に水を添加して非水溶性成分を析出させ、活性炭を加えて撹拌した後、非水溶性成分と活性炭との混合物を分離し、得られた混合物をエタノールで抽出処理し、得られた抽出液からエタノールを留去し、粉末状の濃縮物として、カルノソール及びカルノジック酸を得る。その詳細は、特公昭５９−４４６９号公報の記載を参照することができる。 An example of the production method of carnosol and carnosic acid is as follows. First, as in the case of the water-soluble extract described above, extraction with hydrous ethanol, water is added to the extract to precipitate water-insoluble components, activated carbon is added and stirred, and water-insoluble components and The mixture with activated carbon is separated, the resulting mixture is extracted with ethanol, ethanol is distilled off from the resulting extract, and carnosol and carnosic acid are obtained as a powdery concentrate. The details can be referred to the description in Japanese Patent Publication No. 59-4469.
本発明の抗菌剤におけるベータ酸含有ホップ抽出物とシソ科植物抽出物との含有割合は、本発明の効果を奏する割合であれば特に限定されないが、ベータ酸含有ホップ抽出物の含有割合が少なすぎると、抗菌活性が劣る傾向があり、またシソ科植物抽出物の含有割合が少なすぎると、臭気抑制効果が劣る傾向がある。従って、ベータ酸含有ホップ抽出物と非油溶性シソ科植物抽出物との含有割合は、成分の重量比で、通常９９：１〜１：９９、好ましくは９９：１〜２０：８０、より好ましくは９５：５〜５０：５０、特に好ましくは９０：１０〜７０：３０である。 The content ratio of the beta acid-containing hop extract and the Labiatae plant extract in the antibacterial agent of the present invention is not particularly limited as long as it has the effect of the present invention, but the content ratio of the beta acid-containing hop extract is small. If it is too much, the antibacterial activity tends to be inferior, and if the content of the Labiatae plant extract is too small, the odor suppressing effect tends to be inferior. Therefore, the content ratio of the beta acid-containing hop extract and the non-oil-soluble Labiatae plant extract is usually 99: 1 to 1:99, preferably 99: 1 to 20:80, more preferably by weight ratio of the components. Is 95: 5 to 50:50, particularly preferably 90:10 to 70:30.
本発明の抗菌剤には、必要に応じ、乳化剤、増量剤などを添加することができる。また、本発明の抗菌剤は、粉末、造粒物などの固体としても使用できるが、使用上の便を考慮し、水、エタノール等の溶液として使用することもできる。 If necessary, an emulsifier, a bulking agent and the like can be added to the antibacterial agent of the present invention. The antibacterial agent of the present invention can be used as a solid such as a powder or a granulated product, but can also be used as a solution of water, ethanol or the like in consideration of convenience in use.
上記の乳化剤として、例えば、ポリグリセリンラウリン酸エステル、ポリグリセリンミリスチン酸エステル、ポリグリセリンパルミチン酸エステル、ポリグリセリンステアリン酸エステル、ポリグリセリンオレイン酸エステル、ポリグリセリンベヘン酸エステル等のポリグリセリン脂肪酸エステル；ショ糖オクタン酸エステル、ショ糖デカン酸エステル、ショ糖ラウリン酸エステル、ショ糖ミリスチン酸エステル、ショ糖パルミチン酸エステル、ショ糖ステアリン酸エステル、ショ糖オレイン酸エステル等のショ糖脂肪酸エステル；ポリソルベート４０、６０、６５、８０等のポリソルベート類が挙げられ、これらは２種以上を併用してもよい。乳化剤の含有量は、通常０．０１〜９０重量％、好ましくは０．１〜５０重量％、更に好ましくは１〜２０重量％である。 Examples of the emulsifier include polyglycerol fatty acid esters such as polyglycerol laurate, polyglycerol myristate, polyglycerol palmitate, polyglycerol stearate, polyglycerol oleate, and polyglycerol behenate; Sucrose fatty acid esters such as sugar octoate, sucrose decanoate, sucrose laurate, sucrose myristic ester, sucrose palmitate, sucrose stearate, sucrose oleate; polysorbate 40, Examples thereof include polysorbates such as 60, 65, and 80, and these may be used in combination of two or more. The content of the emulsifier is usually 0.01 to 90% by weight, preferably 0.1 to 50% by weight, and more preferably 1 to 20% by weight.
上記の増量剤としては、例えば、デキストリン、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、化工でんぷんの他、ショ糖、乳糖などの糖類；オリゴトース、トレハロース、キシリトール、エリスリトール等の糖アルコール類；ベツリン酸、ベツリン酸エステル誘導体等のトリテルペン類が挙げられ、これらは２種以上を併用してもよい。増量剤の含有量は、通常０．１〜９０重量％、好ましくは０．５〜５０重量％、更に好ましくは１〜２０重量％である。 Examples of the bulking agent include saccharides such as dextrin, α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, modified starch, sucrose and lactose; sugar alcohols such as oligotose, trehalose, xylitol and erythritol And triterpenes such as betulinic acid and betulinic acid ester derivatives, and two or more of these may be used in combination. The content of the extender is usually 0.1 to 90% by weight, preferably 0.5 to 50% by weight, and more preferably 1 to 20% by weight.
本発明においては、ビタミンＣ、トコフェロール、ビタミンＰ、クロロゲン酸、コーヒー豆抽出物、ひまわり抽出物、ぶどう種子物、α−Ｇルチン、カテキン、緑茶抽出物などの他の酸化防止剤を併用してもよい。これらは２種以上を併用してもよく、その含有量は、通常０．１〜５０重量％、好ましくは０．５〜３０重量％、更に好ましくは１〜２０重量％である。 In the present invention, vitamin C, tocopherol, vitamin P, chlorogenic acid, coffee bean extract, sunflower extract, grape seed extract, α-G rutin, catechin, green tea extract and other antioxidants are used in combination. Also good. Two or more of these may be used in combination, and the content thereof is usually 0.1 to 50% by weight, preferably 0.5 to 30% by weight, and more preferably 1 to 20% by weight.
本発明の抗菌剤は、前記の各成分を混合して製造される。混合順序や方法は特に制限されない。ベータ酸含有ホップ抽出物、シソ科植物抽出物、その他の成分の割合（重量比）は、上記のとおり、特に限定されず広い範囲から選択することができる。 The antibacterial agent of the present invention is produced by mixing the components described above. The mixing order and method are not particularly limited. The ratio (weight ratio) of the beta acid-containing hop extract, Lamiaceae plant extract, and other components is not particularly limited as described above, and can be selected from a wide range.
通常、本発明の抗菌剤の１つの剤形は、前記の各成分を水またはエタノール−水の混合溶媒に溶解させた溶液である。他の剤形は、上記の溶液をスプレードライ又は凍結乾燥した粉体である。粉体の場合は、常法に従い、賦形剤などの各種の添加剤が使用される。 Usually, one dosage form of the antibacterial agent of the present invention is a solution in which each of the above components is dissolved in water or a mixed solvent of ethanol-water. Another dosage form is a powder obtained by spray drying or freeze-drying the above solution. In the case of powder, various additives such as excipients are used in accordance with conventional methods.
また、本発明の抗菌剤は、徐放性を発揮し得る形態で使用することができる。例えば、劣化臭防止剤を包む吸湿性のカプセル粒子を作成し、一定の湿度以上の雰囲気下で当該物質を放出し得るような、サイクロデキストリン、アラビアガム、ゼラチン、ヘミセルロース、微生物産生多糖類、改質デンプン等の水溶性フィルム形成剤と必要に応じて粉末賦形剤を水中に溶解および／または分散させた後、本発明の劣化臭防止剤を乳化処理することで得られた乳化液を噴霧乾燥して粉末化することにより製造することができる。乳化処理の際は必要に応じて乳化剤を使用してもよい。 Moreover, the antibacterial agent of this invention can be used with the form which can exhibit sustained-release property. For example, hygroscopic capsule particles enclosing a deodorizing odor preventing agent are prepared, and cyclodextrin, gum arabic, gelatin, hemicellulose, microbially produced polysaccharides, modified so as to release the substance in an atmosphere of a certain humidity or higher. A water-soluble film forming agent such as starch and a powder excipient as necessary are dissolved and / or dispersed in water, and then the emulsion obtained by emulsifying the deterioration odor inhibitor of the present invention is sprayed. It can be produced by drying and pulverizing. In the emulsification treatment, an emulsifier may be used as necessary.
本発明の抗菌剤は、上記のように、用途に合わせ、溶解液、乳化製剤、粉末その他任意の剤形で使用でき、用途により適宜付加することもできる。 As described above, the antibacterial agent of the present invention can be used in the form of a solution, an emulsified preparation, a powder, or any other dosage form according to the application, and can be appropriately added depending on the application.
本発明の抗菌剤は、諸種の微生物に対して効果的な抗菌活性を示すが、特にグラム陽性菌、例えば、スタフィロコッカス（Staphyrococcus）属、ラクトバシルス（Lactobacillus）属、リステリア（Listeria）属、アリシクロバシルス（Alicyclobacillus）属、及び、バシルス（Bacillus）属から成る群より選ばれる何れかの属に属する細菌に対して使用することが好ましい。 Antibacterial agent of the present invention exhibit effective antimicrobial activity against microorganisms Shoshu, especially gram-positive bacteria, e.g., Staphylococcus (Staphyrococcus) genus Lactobacillus (Lactobacillus) genus Listeria (Listeria) genus, Ali Shikurobashirusu (Alicyclobacillus) genus, and it is preferable to use against bacteria belonging to any genus selected from the group consisting of Bacillus (Bacillus) genus.
特に、本発明の抗菌剤は、スタフィロコッカス・アウレウス（Staphyrococcus aureusu）、ラクトバシルス・プランタルム（Lactobacillus plantarum）、リステリア・モノシトジェネス（Listeria monocytogenes）、アリシクロバシルス・アシドテレストリス（Alicyclobacillus acidoterrestris）、及び、バシルス・サブチルス（Bacillus subtilis）から成る群より選ばれる種に属する細菌に対して顕著な効果を発揮する。また、本発明の抗菌剤は、リステリア（Listeria）属に属する細菌、例えばリステリア・モノシトジェネス（Listeria monocytogenes）に対する抗菌剤として特に有効である。 In particular, the antibacterial agent of the present invention includes Staphyrococcus aureusu , Lactobacillus plantarum , Listeria monocytogenes , Alicyclobacillus acidoterrestris , And it exerts a remarkable effect on bacteria belonging to a species selected from the group consisting of Bacillus subtilis . The antibacterial agent of the present invention is particularly effective as an antibacterial agent against bacteria belonging to the genus Listeria , such as Listeria monocytogenes .
本発明の抗菌剤は、例えば、食品、飲料、医療、医薬品、環境安全の分野において広く使用することができるが、特に食品保存剤として有用である。本発明の抗菌剤を、これら分野における諸種の試料に添加することにより、試料中における抗菌活性を発現することができる。
本発明の抗菌剤を添加する試料としては、微生物の生育し易い食品が好適であり、その具体例としては、水産、畜肉、油脂加工品が挙げられる。特に、劣化し易い水産、畜肉、油脂加工品及び長期間保存する水産、畜肉、油脂加工品に好ましく使用できる。その具体例としては、鮮魚、干物、一夜干し、みりん干し、貝類、赤魚、甲殻類の色素維持剤、すり身、水産練り製品、珍味、魚肉ソーセージ、塩蔵品、ノリ、海藻食品、鶏肉、豚肉、牛肉、羊肉、ソーセージ、ハム、それを加工した製品などがある。
The antibacterial agent of the present invention can be widely used, for example, in the fields of food, beverages, medicine, pharmaceuticals, and environmental safety, but is particularly useful as a food preservative. By adding the antibacterial agent of the present invention to various samples in these fields, the antibacterial activity in the sample can be expressed.
The sample to which the antibacterial agent of the present invention is added is preferably a food that easily grows microorganisms, and specific examples thereof include fishery products, livestock meat, and processed oils and fats. In particular, it can be preferably used for marine products, livestock meat, processed oil products that are easily deteriorated, and fishery products, livestock meat, processed oil products that are stored for a long time. Specific examples include fresh fish, dried fish, dried overnight, mirin dried, shellfish, red fish, crustacean pigment preservation agent, surimi, marine products, delicacy, fish sausage, salted products, seaweed, seaweed food, chicken, pork, There are beef, lamb, sausage, ham and processed products.
本発明の抗菌剤の試料への添加濃度は、ベータ酸量として、通常１〜１５０ｐｐｍ、好ましくは３〜１００ｐｐｍ、更に好ましくは５〜５０ｐｐｍである。また、本発明の抗菌剤は、他の抗菌剤（例えば、グラム陰性菌に効力のあるポリリジン、グレープフルーツ種子抽出物、カラシ抽出物等）と組み合わせて使用することにより、より効率的に抗菌活性を示すことができる。 The concentration of the antibacterial agent of the present invention added to the sample is usually 1 to 150 ppm, preferably 3 to 100 ppm, more preferably 5 to 50 ppm as the amount of beta acid. In addition, the antibacterial agent of the present invention has a more efficient antibacterial activity when used in combination with other antibacterial agents (for example, polylysine effective against gram-negative bacteria, grapefruit seed extract, mustard extract, etc.). Can show.
以下、実施例をあげて本発明を更に詳細に説明するが、本発明は、その要旨を超えない限り、以下の実施例に制限されるものではない。 EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further in detail, this invention is not restrict | limited to a following example, unless the summary is exceeded.
（非油溶性ローズマリー抽出物）
ローズマリー１ｋｇに５０％含水エタノール１０Ｌを加えて３時間加熱還流し、温時に濾過して濾液を得た。残渣を５０％含水エタノール６Ｌで同様に抽出する操作を更に２回繰り返して濾液を得た。これらの濾液を合わせ、水５Ｌを加えて沈殿物を析出させた。これに活性炭１００ｇを加え、１時間撹拌し、一夜冷所で保存した後に濾過して濾液Ａを得た。また、ローズマリー１ｋｇに５０％含水エタノール１０Ｌを加えて３時間加熱還流し、温時に濾過して濾液を得た。残渣を５０％含水エタノール６Ｌで同様に抽出する操作を更に２回繰り返して濾液を得た。これらの濾液を合わせ、水５Ｌを加えて沈殿物を析出させた。これに活性炭１００ｇを加え、１時間撹拌し、一夜冷所で保存した後に濾過して沈殿と活性炭の混合物を得た。この混合物にエタノール４Ｌを加え、３時間加熱還流し、温時に濾過して濾液を得た。残渣をエタノール２．４Ｌで同様に抽出する操作を更に２回繰り返して濾液Ｂを得た。濾液Ａと濾液Ｂを合わせ、減圧濃縮して、粉末状の非油溶性ローズマリー抽出物を得た。以下の実施例では、かくして得られた非油溶性ローズマリー抽出物（ＲＭ抽出物）を用いた。
(Non-oil soluble rosemary extract)
10 kg of 50% aqueous ethanol was added to 1 kg of rosemary, heated under reflux for 3 hours, and filtered while warm to obtain a filtrate. The operation of extracting the residue with 6 L of 50% aqueous ethanol in the same manner was repeated twice more to obtain a filtrate. These filtrates were combined, and 5 L of water was added to precipitate a precipitate. 100 g of activated carbon was added thereto, stirred for 1 hour, stored in a cold place overnight, and then filtered to obtain a filtrate A. Further, 10 L of 50% aqueous ethanol was added to 1 kg of rosemary, and the mixture was heated to reflux for 3 hours and filtered while warm to obtain a filtrate. The operation of extracting the residue with 6 L of 50% aqueous ethanol in the same manner was repeated twice more to obtain a filtrate. These filtrates were combined, and 5 L of water was added to precipitate a precipitate. 100 g of activated carbon was added thereto, stirred for 1 hour, stored in a cold place overnight, and then filtered to obtain a mixture of precipitate and activated carbon. 4 L of ethanol was added to this mixture, and the mixture was heated to reflux for 3 hours and filtered while warm to obtain a filtrate. The operation of extracting the residue in the same manner with 2.4 L of ethanol was repeated twice more to obtain filtrate B. The filtrate A and the filtrate B were combined and concentrated under reduced pressure to obtain a powdery non-oil-soluble rosemary extract. In the following Examples, the oil-insoluble rosemary extract (RM extract) thus obtained was used.
（ホップ抽出物）
市販ホップエキス製品を用いてもよく、具体的にはステイナー社の超臨界抽出ホップエキス（商品名：ベータ・アロマ・エクストラクト）が好適に使用できる。
このものは、ベータ酸濃度が約４０〜５０％程度である。更にこのものを精製して用いることもできる。精製法はホップエキスを水酸化ナトリウム等のアルカリ溶液でベータ酸類を溶解した後浮遊する油分を除去する。油分除去後塩酸等で中和するとベータ酸７０％程度の高濃度のものが得られる。以下の実施例では、かくして得られたベータ酸濃度が７０％程度のホップ抽出物（ＨＯＰ抽出物）を用いた。
(Hop extract)
A commercially available hop extract product may be used, and specifically, a supercritical extraction hop extract (trade name: Beta Aroma Extract) manufactured by Steiner can be suitably used.
This has a beta acid concentration of about 40-50%. Furthermore, this thing can also be refine | purified and used. In the refining method, the hop extract is dissolved in beta acids with an alkaline solution such as sodium hydroxide, and then the floating oil is removed. After removal of the oil, neutralization with hydrochloric acid or the like provides a high concentration of about 70% beta acid. In the following examples, the hop extract (HOP extract) having a beta acid concentration of about 70% thus obtained was used.
実施例１（リステリア・モノシトジェネスに対する抗菌活性）
増殖培地として、ブレインハートインヒュージョンブイヨン（ＢＨＩ）「ニッスイ」、試験培地として、ニュートリエントブロス（ＮＢ）「ニッスイ」を使用した（何れも日水製薬社製）。
先ず、ＢＨＩ培地中で３７℃、一晩増殖培養させたリステリア・モノシトジェネス（L.monocytogenes）(ATCC49594）の菌液を滅菌リン酸緩衝液で希釈し、１．６×１０4 個／ｍｌの試験菌液を調製した。
一方、上記ＲＭ抽出物１ｇをエタノール１０ｍLに懸濁させ、１０重量％ローズマリー非水溶生物エタノール懸濁液を作成し、滅菌水で希釈して５、１０、３０、５０、１００ｐｐｍの非水溶性物ローズマリー抽出物の水溶液（ＲＭ水溶液）を調製した。
また、ＨＯＰ抽出物は１ｇをエタノール１０ｍｌに溶解させ１０％重量ホップエタノール液を作成し、滅菌水で希釈して１０、５０、１００、２００、５００、７５０ｐｐｍのホップ抽出物の水溶液（ＨＯＰ水溶液）を調製した。
Example 1 (Antimicrobial activity against Listeria monocytogenes)
Brain heart infusion bouillon (BHI) “Nissui” was used as the growth medium, and Nutrient broth (NB) “Nissui” was used as the test medium (all manufactured by Nissui Pharmaceutical Co., Ltd.).
First, a bacterial solution of L. monocytogenes (ATCC49594) grown overnight in a BHI medium at 37 ° C. was diluted with a sterile phosphate buffer, and 1.6 × 10 4 cells / ml. A test bacterial solution was prepared.
On the other hand, 1 g of the above RM extract is suspended in 10 mL of ethanol to prepare a 10 wt% rosemary water-insoluble biological ethanol suspension, diluted with sterilized water, and water-insoluble at 5, 10, 30, 50, 100 ppm. An aqueous solution (RM aqueous solution) of a product rosemary extract was prepared.
In addition, 1 g of HOP extract is dissolved in 10 ml of ethanol to prepare a 10% weight hop ethanol solution, diluted with sterilized water, and 10, 50, 100, 200, 500, 750 ppm hop extract aqueous solution (HOP aqueous solution) Was prepared.
次いで、ＮＢ培地４．０ｍｌの入った滅菌済み試験管に、各濃度のＲＭ水溶液及びＨＯＰ水溶液を各０．５ｍｌ添加した。これらに、調製した菌液０．１ ｍｌを添加し、溶液が均一になるように攪拌した。肉眼観察時の対照として、菌液の替わりに滅菌精製水０．１ｍｌ添加したものを、各濃度ごとに１本ずつ作成した。
３７℃、２４時間培養後に試験液の濁りを肉眼観察して増殖抑制を判定した。その結果を表１に示す。なお、表１〜５中、「−」は「液は対照液と同じ透明性で菌の増殖を認めない」、「＋」は「液は対照液より白濁し菌の増殖を認める」を示す。
Subsequently, 0.5 ml of RM aqueous solution and HOP aqueous solution of each concentration were added to a sterilized test tube containing 4.0 ml of NB medium. To these, 0.1 ml of the prepared bacterial solution was added and stirred so that the solution was uniform. As a control during macroscopic observation, 0.1 ml of sterilized purified water added instead of the bacterial solution was prepared for each concentration.
After incubation at 37 ° C. for 24 hours, the turbidity of the test solution was visually observed to determine growth inhibition. The results are shown in Table 1. In Tables 1 to 5, “-” indicates “the liquid is the same transparency as the control solution and no growth of the bacteria is observed”, and “+” indicates “the liquid is more cloudy than the control solution and the growth of the bacteria is recognized”. .
実施例２（スタフィロコッカス・アウレウスに対する抗菌活性）
増殖培地として、ブレインハートインヒュージョンブイヨン（ＢＨＩ）「ニッスイ」、試験培地として、ニュートリエントブロス（ＮＢ）「ニッスイ」を使用した（何れも日水製薬社製）。
先ず、ＢＨＩ培地中で３７℃、一晩増殖培養させたスタフィロコッカス・アウレウス（S.aureus）(IFO12732）の菌液を滅菌リン酸緩衝液で希釈し、３．２×１０4 個／ｍｌの試験菌液を調製した。以後の操作は実施例１と同様に行い増殖抑制の試験を実施した。その結果を表２に示す。
Example 2 (Antimicrobial activity against Staphylococcus aureus)
Brain heart infusion bouillon (BHI) “Nissui” was used as the growth medium, and Nutrient broth (NB) “Nissui” was used as the test medium (all manufactured by Nissui Pharmaceutical Co., Ltd.).
First, 37 ° C. in BHI medium diluted with bacterial solution sterile phosphate buffer overnight growth culture is Staphylococcus aureus was (S. Aureus) (IFO12732) , 3.2 × 10 4 cells / ml A test bacterial solution was prepared. Subsequent operations were performed in the same manner as in Example 1, and a growth inhibition test was performed. The results are shown in Table 2.
実施例３（ラクトバシルス・プランタルムに対する抗菌活性）
増殖培地として、ブレインハートインヒュージョンブイヨン（ＢＨＩ）「ニッスイ」、試験培地として、ニュートリエントブロス（ＮＢ）「ニッスイ」を使用した（何れも日水製薬社製）。
先ず、ＢＨＩ培地中で３７℃、一晩増殖培養させたラクトバシルス・プランタルム（L.plantarum）(TFC2005）の菌液を滅菌リン酸緩衝液で希釈し、２．０×１０4 個／ｍｌの試験菌液を調製した。以後の操作は実施例１と同様に行い増殖抑制の試験を実施した。その結果を表３に示す。
Example 3 (Antimicrobial activity against Lactobacillus plantarum)
Brain heart infusion bouillon (BHI) “Nissui” was used as the growth medium, and Nutrient broth (NB) “Nissui” was used as the test medium (all manufactured by Nissui Pharmaceutical Co., Ltd.).
First, a bacterial solution of L. plantarum (TFC2005) grown overnight in a BHI medium at 37 ° C. was diluted with a sterilized phosphate buffer and tested at 2.0 × 10 4 cells / ml. A bacterial solution was prepared. Subsequent operations were performed in the same manner as in Example 1, and a growth inhibition test was performed. The results are shown in Table 3.
実施例４（バシルス・サブチルスに対する抗菌活性）
増殖培地として、ブレインハートインヒュージョンブイヨン（ＢＨＩ）「ニッスイ」、試験培地として、ニュートリエントブロス（ＮＢ）「ニッスイ」を使用した（何れも日水製薬社製）。
先ず、ＢＨＩ培地中で３７℃、一晩増殖培養させたバシルス・サブチルス（B.subtillis）(ATCC6633）の菌液を滅菌リン酸緩衝液で希釈し、２．８×１０4 個／ｍｌの試験菌液を調製した。以後の操作は実施例１と同様に行い増殖抑制の試験を実施した。その結果を表４に示す。
Example 4 (Antimicrobial activity against Bacillus subtilis)
Brain heart infusion bouillon (BHI) “Nissui” was used as the growth medium, and Nutrient broth (NB) “Nissui” was used as the test medium (all manufactured by Nissui Pharmaceutical Co., Ltd.).
First, a bacterial solution of B. subtillis (ATCC6633) grown overnight at 37 ° C. in BHI medium was diluted with a sterile phosphate buffer and tested at 2.8 × 10 4 cells / ml. A bacterial solution was prepared. Subsequent operations were performed in the same manner as in Example 1, and a growth inhibition test was performed. The results are shown in Table 4.
実施例５（アリシクロバシルス・アシドテレストリスに対する抗菌活性）
増殖培地および試験培地として、硫酸でｐＨ３．８に調製したブレインハートインヒュージョンブイヨン（ＢＨＩ）「ニッスイ」を使用した（日水製薬社製）。
先ず、ＢＨＩ培地中で４０℃、一晩増殖培養させたアリシクロバシルス・アシドテレストリス（A.acidterrestris）(ATCC49025）の菌液を滅菌リン酸緩衝液で希釈し、９．３×１０３ 個／ｍｌの試験菌液を調製した。以後の操作は、培養温度を０℃に試験培地を硫酸でｐＨ３．８に調製したＢＨＩに変更した以外は実施例１と同様に行った。その結果を表５に示す。
Example 5 (Antimicrobial activity against Alicyclobacillus acid telestris)
Brain heart infusion bouillon (BHI) “Nissui” adjusted to pH 3.8 with sulfuric acid was used as a growth medium and test medium (manufactured by Nissui Pharmaceutical Co., Ltd.).
First, a bacterial solution of A. acidterrestris (ATCC49025) grown overnight in BHI medium at 40 ° C. was diluted with a sterile phosphate buffer to obtain 9.3 × 10 3. Individual / ml test bacterial solution was prepared. The subsequent operation was carried out in the same manner as in Example 1 except that the culture temperature was changed to 0 ° C. and the test medium was changed to BHI adjusted to pH 3.8 with sulfuric acid. The results are shown in Table 5.
実施例６（臭気抑制作用）
（１）官能試験
上記７０％ＨＯＰ抽出物をエタノールに溶解し、１重量％溶液（１％ＨＯＰ溶液）とした。また、上記ＲＭ抽出物をエタノールに溶解し、１重量％溶液（１％ＲＭ溶液）とした。これら溶液を表６に示す割合で混合し、臭いの評価を行った。
Example 6 (Odor control action)
(1) Sensory test The 70% HOP extract was dissolved in ethanol to give a 1 wt% solution (1% HOP solution). The RM extract was dissolved in ethanol to give a 1% by weight solution (1% RM solution). These solutions were mixed at the ratios shown in Table 6 and the odor was evaluated.
その結果、サンプルＮｏ．１１と比べて、サンプルＮｏ．１０と８の間（１％ＨＯＰ溶液／１％ＲＭ溶液＝９０／１０〜７０／３０）で、ホップ臭が急激に弱まり、さらに１％ＲＭ溶液の混合割合高いサンプルＮｏ．４と３の間（１％ＨＯＰ溶液／１％ＲＭ溶液＝２０／８０〜３０／７０）で、ホップ臭が完全に消失した。この結果から、ホップ臭を抑制に関して、官能面からのＨＯＰ抽出物とＲＭ抽出物の混合割合は、成分比でホップ濃度が高い条件では、９０：１０〜７０：３０が好ましく、ホップ臭が消える条件は２０：８０よりもＲＭ濃度が高いことが好ましいことがわかった。 As a result, sample no. Compared to sample 11, sample no. Between 10 and 8 (1% HOP solution / 1% RM solution = 90 / 10-70 / 30), the hop odor sharply decreased, and the mixing ratio of the 1% RM solution was high. The hop odor disappeared completely between 4 and 3 (1% HOP solution / 1% RM solution = 20 / 80-30 / 70). From this result, regarding the suppression of the hop odor, the mixing ratio of the HOP extract and the RM extract from the functional aspect is preferably 90:10 to 70:30 under the condition that the hop concentration is high in the component ratio, and the hop odor disappears. It was found that the condition is preferably higher in RM concentration than 20:80.
（２）ガスクロマトグラフィー分析
上記の官能試験に供したサンプルを用いて、ヘッドスペース固相マイクロ抽出法（ＨＳ−ＳＰＭＥ）で臭気成分を抽出し、ＧＣ／ＭＳにより分析を行った。ＨＳ−ＳＰＭＥ装置はＭＰＳ２（ＧＥＲＳＴＥＬ社製）、ＧＣ／ＭＳ装置はＨＰ６８９０（Ａｇｉｌｅｎｔ社製）／Ｍａｓｓ Ｓｅｎｓｉｔｉｖｅ Ｄｅｔｅｃｔｏｒ ５９７３Ｎ（Ａｇｉｌｅｎｔ社製）を用いた。
その結果を表７に示す。表７中の値は、サンプルＮｏ．１１（１％ＨＯＰ溶液／１％ＲＭ溶液＝１００／０）の測定値を１００％とする相対値である。
(2) Gas Chromatographic Analysis Using the sample subjected to the above sensory test, odor components were extracted by the headspace solid phase microextraction method (HS-SPME) and analyzed by GC / MS. MPS2 (manufactured by GERSTEL) was used as the HS-SPME device, and HP6890 (manufactured by Agilent) / Mass Sensitive Detector 5973N (manufactured by Agilent) was used as the GC / MS device.
The results are shown in Table 7. The values in Table 7 are sample Nos. 11 (1% HOP solution / 1% RM solution = 100/0) is a relative value with the measured value as 100%.
表７の結果から明らかなとおり、１％ＲＭ溶液の混合割合が高いほど臭気成分は減少し、サンプルＮｏ．１１（１％ＨＯＰ溶液／１％ＲＭ溶液＝１００／０）と比較し、サンプルＮｏ．１０（１％ＨＯＰ溶液／１％ＲＭ溶液＝９０／１０）では、２−メチル−１，３−ブタンジエンが５４％減少、２−メチル−３−ブテナールが３４％減少した。この結果は、上記官能試験の結果と一致するものであった。 As apparent from the results in Table 7, the higher the mixing ratio of the 1% RM solution, the lower the odor component. 11 (1% HOP solution / 1% RM solution = 100/0). In 10 (1% HOP solution / 1% RM solution = 90/10), 2-methyl-1,3-butanediene decreased by 54% and 2-methyl-3-butenal decreased by 34%. This result was consistent with the result of the sensory test.
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| EP3253232B1 (en) * | 2015-02-06 | 2020-08-12 | Naturex S.A. | Antimicrobial compositions |
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| JPS51133438A (en) * | 1974-04-03 | 1976-11-19 | Jitsuo Kawabata | Method of producing natural food preservatives |
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| EP3253232B1 (en) * | 2015-02-06 | 2020-08-12 | Naturex S.A. | Antimicrobial compositions |
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