JP2021134175A - Microbial inhibitor based on spiculisporic acid - Google Patents

Abstract

To inhibit microbes using spiculisporic acid-related substance.SOLUTION: In one aspect, the present disclosure provides a spiculisporic acid-related substance for inhibiting microbes. The spiculisporic acid-related substance may be spiculisporic acid or a derivative thereof or a salt thereof or a mixture of them. In one embodiment, the microbial inhibitor inhibits microbes including bacteria. In one embodiment, the microbial inhibitor inhibits microbes including fungi.SELECTED DRAWING: None

Description

The present disclosure relates to microbial inhibitors using spicrysporic acid-related substances and their use.

Microbial inhibitors are widely used in food disinfection, detergents, cleaning around water, and maintaining the surface cleanliness of various daily necessities. Since there are many opportunities for the microbial inhibitor to come into contact with the skin and mucous membranes of animals such as humans, naturally derived agents with high safety are required. However, there are few kinds of microbial inhibitors derived from natural products, and there are many cases where the productivity is poor (Patent Document 1). In addition, since properties such as hydrophilicity and other physicochemical properties, stability, and degradability may differ for each microbial inhibitor, it is useful to provide a microbial inhibitor having new properties (or a combination of properties). be.

Japanese Unexamined Patent Publication No. 1-132515

The present inventors have unexpectedly found that spicrysporic acid-related substances have microbial inhibitory activity. Based on this knowledge, new uses of spicrysporic acid-related substances as microorganism inhibitors and the like become possible.

（式中、
Ｒ^１、Ｒ^２およびＲ^３は、それぞれ独立に、−ＯＲ^Ａ、−ＮＨＲ^Ａまたは−Ｎ（Ｒ^Ａ）_２であり、
Ｒ^４は、−Ｈ、−ＯＨ、−ＯＲ^Ａまたは−ＮＨＲ^Ａであるか、または破線で示される部分に追加の結合を形成することで二重結合を形成し、
ここで、Ｒ^Ａは、１〜２個のカルボキシル基で必要に応じて置換されていてもよい炭素数１〜２１の飽和又は不飽和である分岐または直鎖炭化水素基であるか、または
Ｒ^１、Ｒ^２、Ｒ^３およびＲ^４のうちのいずれか２つは、一緒になって−Ｏ−の架橋を形成していてもよいし、あるいは
２つの分子におけるＲ^１、Ｒ^２、Ｒ^３およびＲ^４のうちのいずれか１つ同士が分子間で連結し、２量体を形成してもよい）
で表される化合物またはその塩を含む、項目１〜４のいずれか一項に記載の微生物抑制剤。
（項目６）
前記スピクリスポール酸関連物質が、

からなる群から選択される化合物またはその塩を含む、項目１〜４のいずれか一項に記載の微生物抑制剤。
（項目７）
前記スピクリスポール酸関連物質が、式Ａまたは式Ｂ
式Ａまたは式Ｂ

（式中、
Ｃ_１０Ｈ_２１は、直鎖状の飽和炭素鎖を表し、
−Ｘ^１−および−Ｘ^２−は、それぞれ独立に、−Ｏ−、−Ｓ−および−ＮＨ−からなる群から選択され、
−Ｙ−は、それぞれ独立に、炭素を含む２価のリンカー基であり、
Ｒ^１は、それぞれ独立に、−Ｈ、−ＯＨ、−ＯＲ^Ａまたは−ＮＨＲ^Ａであるか、または破線で示される部分に追加の結合を形成することで二重結合を形成し、
Ｒ^２は、それぞれ独立に、−ＯＨ、−ＯＲ^Ａ、−ＮＨＲ^Ａまたは−Ｎ（Ｒ^Ａ）_２であり、
ｎは、それぞれ独立に、１以上の整数であり、
ここで、Ｒ^Ａは、１〜２個のカルボキシル基で必要に応じて置換されていてもよい炭素数１〜２１の飽和又は不飽和である分岐または直鎖炭化水素基である）
で表される少なくとも１つの部分を含むスピクリスポール酸誘導ポリマーまたはその塩を含む、項目１〜４のいずれか一項に記載の微生物抑制剤。
（項目８）
金属成分を含む、項目１〜７のいずれか一項に記載の微生物抑制剤。
（項目９）
洗剤、皮膚に適用するスプレー、除菌または抗菌スプレーまたは水回り製品である、項目１〜８のいずれか一項に記載の微生物抑制剤。
（項目１０）
高分子材料である、項目１〜９のいずれか一項に記載の微生物抑制剤。 Therefore, the present invention provides the following.
(Item 1)
Microbial inhibitors, including spicrysporic acid-related substances.
(Item 2)
The microorganism inhibitor according to item 1, wherein the microorganism contains a bacterium.
(Item 3)
The microorganism inhibitor according to item 1, wherein the microorganism comprises a fungus.
(Item 4)
Wherein the microorganism, Escherichia genus, Methylobacterium spp, Micrococcus spp, Pseudomonas spp, Staphylococcus spp, Serratia spp, Rhodotorula spp, Aspergillus spp, Penicillium spp, Scolecobasidium spp, Exophiala spp, Cladosporium sp, Phoma spp, Trichoderma spp, Alternaria spp, Aureobasidium The microbial inhibitor according to item 1, which comprises a genus and a genus selected from the genus Ulocradium.
(Item 5)
The spicrysporic acid-related substance is the formula I.

(During the ceremony,
R ¹ , R ² and R ³ are independently -OR ^A , -NHR ^A or -N ( ^RA ) ₂ , respectively.
R ⁴ forms -H, -OH, or an -OR ^A, or -NHR ^A, or a double bond at the moiety indicated to form an additional bond by a broken line,
Here, ^RA is a saturated or unsaturated branched or linear hydrocarbon group having 1-21 carbon atoms, which may be optionally substituted with 1-2 carboxyl groups, or R. ^{1, R} 2, ^{R 3} and any two of ^{R 4} may be optionally form a bridge of together -O- ^R 1 or at the two ^molecules,, R 2, ^{R 3} and any one among of R ⁴ is connected between the molecules, it may form a dimer)
The microorganism inhibitor according to any one of items 1 to 4, which comprises the compound represented by (1) or a salt thereof.
(Item 6)
The spicysporic acid-related substance is

The microorganism inhibitor according to any one of items 1 to 4, which comprises a compound selected from the group consisting of or a salt thereof.
(Item 7)
The spicrysporic acid-related substance is Formula A or Formula B.
Formula A or formula B

(During the ceremony,
C ₁₀ H ₂₁ represents a linear saturated carbon chain.
-X ^1- and -X ² --are independently selected from the group consisting of -O-, -S- and -NH-, respectively.
-Y- is a divalent linker group containing carbon independently of each other.
R ¹ is, independently, formed -H, -OH, or an -OR ^A, or -NHR ^A, or a double bond at the moiety indicated to form an additional bond by a broken line,
R ² are independently -OH, -OR ^A , -NHR ^A or -N ( ^RA ) ₂ , respectively.
n is an integer of 1 or more independently of each other.
Here, ^RA is a saturated or unsaturated branched or linear hydrocarbon group having 1 to 21 carbon atoms which may be optionally substituted with 1 to 2 carboxyl groups).
The microorganism inhibitor according to any one of items 1 to 4, which comprises a spicrysporic acid-induced polymer or a salt thereof containing at least one moiety represented by.
(Item 8)
The microorganism inhibitor according to any one of items 1 to 7, which contains a metal component.
(Item 9)
The microbial inhibitor according to any one of items 1 to 8, which is a detergent, a spray applied to the skin, a disinfectant or antibacterial spray, or a water-related product.
(Item 10)
The microorganism inhibitor according to any one of items 1 to 9, which is a polymer material.

In the present invention, it is intended that the one or more features described above may be provided in combination in addition to the specified combinations. Further embodiments and advantages of the present invention will be appreciated by those skilled in the art upon reading and understanding the following detailed description, if necessary.

The present disclosure provides a microbial inhibitor that reflects at least one property of spicrysporic acid by providing a microbial inhibitor containing a spicrysporic acid-related substance.

The result of adding spicrysporic acid powder to the medium inoculated with various bacteria and culturing for 7 days is shown. From the upper left, the photographs show Escherichia coli, Methylobacterium aquaticum, Micrococcus luteus, Pseudomonas aeruginosa, Staphylococcus aureus, and Serratia marcus, respectively. In all the samples, bacterial growth was not observed and halos were formed near the center to which the spicrysporic acid powder was added. The results of adding spicrysporic acid powder to the medium in which various fungi were inoculated and culturing for 13 days are shown. The upper photo shows the result of Aspergillus niger (n = 2), and the lower photo shows the result of Chaetomium globosam (n = 2). In all the samples, the growth of fungi was suppressed near the center to which the spicrysporic acid powder was added. The result of adding open ring acid (O acid) together with Aspergillus niger and culturing for 40 hours is shown. The left photo shows the result of adding only Aspergillus niger (control), the center photo shows the result of adding monosodium O acid, and the right photo shows the result of adding trisodium O acid. Aspergillus niger was suppressed in the sample to which O acid was added as compared with the control sample. Aspergillus niger was suppressed in the sample to which the monosodium O acid was added as compared with the sample to which the trisodium O acid was added. The results of adding various concentrations of open ring acid (O acid) together with Escherichia coli and culturing with shaking at 30 ° C. and 150 rpm for 16 hours are shown. The left column shows the result of adding only E. coli (n = 3), the center column shows the result of adding E. coli and O acid (n = 3), and the right column shows the result of adding only O acid. Each stage shows the results of adding 0.5 g / L, 1 g / L, 3 g / L, and 5 g / L of O acid from the top. Escherichia coli was efficiently suppressed in the sample to which O acid was added at 3 g / L or 5 g / L. The result of adding various substances to the medium in which Aspergillus niger was inoculated and culturing for 10 days is shown (n = 3). Left 1st stage: Control (no chemical addition), Left 2nd stage: S acid, Left 3rd stage: O acid, Left 4th stage: D acid, Right 1st stage: Tea extract, Right 2nd stage: Chitosan, 3rd row on the right: Wasabi extract. In the sample to which S acid, O acid and D acid were added, suppression of Aspergillus niger was observed. The sample to which O acid was added showed the strongest inhibitory effect, followed by the effect of S acid. No inhibitory effect on Aspergillus niger was observed in any of the samples to which tea extract, wasabi extract and chitosan were added.

Hereinafter, the present invention will be described while showing the best mode. Throughout the specification, it should be understood that the singular representation also includes its plural concept, unless otherwise stated. Therefore, it should be understood that singular articles (eg, "a", "an", "the", etc. in English) also include the plural concept unless otherwise noted. It should also be understood that the terms used herein are used in the meaning commonly used in the art unless otherwise noted. Thus, unless otherwise defined, all terminology and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, this specification (including definitions) takes precedence.

(Definition)
The definitions and / or basic technical contents of terms particularly used in the present specification will be described below as appropriate.

As used herein, the term "spicrysporic acid-related substance" refers to spicysporic acid or a derivative thereof, a salt thereof, or a mixture thereof.

（３Ｓ，４Ｓ）−３−ヒドロキシ−１，３，４−テトラデカントリカルボン酸１，３−ラクトン（Ｓ酸）
を有する天然の両親媒性化合物であり、糸状菌（Ｐｅｎｉｓｉｌｌｉｕｍ ｓｐｉｃｕｌｉｓｐｏｒｕｍ Ｌｅｈｍａｎ １０−１）から生産することができ、ヒトへの刺激が少なく、生分解性に優れているなどの特徴を有する。本明細書において、（３Ｓ，４Ｓ）−３−ヒドロキシ−１，３，４−テトラデカントリカルボン酸１，３−ラクトンおよびその塩を総称して、スピクリスポール酸またはＳ酸と呼び得る。スピクリスポール酸は微生物由来の酵素反応によって生産でき、分子内に少なくとも二つのキラル炭素を含み、複数の官能基を有する。スピクリスポール酸は二価の酸であり、ｐＫａ_１は４．５１であり、ｐＫａ_２は６．８８である。１分子のスピクリスポール酸は、１分子の塩基または２分子の塩基とともに塩を形成し得る。 Spikrisporic acid (also referred to herein as "S acid") has the following structure:

(3S, 4S) -3-Hydroxy-1,3,4-Tetradecane tricarboxylic acid 1,3-lactone (S acid)
It is a natural amphipathic compound having the above, can be produced from filamentous fungi (Penisilium spiculusporum Lehman 10-1), has less irritation to humans, and has excellent biodegradability. In the present specification, (3S, 4S) -3-hydroxy-1,3,4-tetradecantricarboxylic acid 1,3-lactone and salts thereof can be collectively referred to as spicrysporic acid or S acid. Spicrisporic acid can be produced by an enzymatic reaction derived from a microorganism, contains at least two chiral carbons in the molecule, and has a plurality of functional groups. Spicrisporic acid is a divalent acid, pKa ₁ is 4.51 and pKa ₂ is 6.88. One molecule of spicrysporic acid can form a salt with one molecule of base or two molecules of base.

As used herein, the term "spicrysporic acid derivative" refers to a compound having a chemical structure similar to that of spicysporic acid, and examples thereof are described in the present specification such as spicysporic acid-induced polymers.

As used herein, the term "polymer material" refers to an article molded from one or more polymers, typically comprising the spicrysporic acid-derived polymers described herein, and optionally. It further comprises another polymer or resin.

As used herein, "suppression" of a microorganism (eg, fungus, bacterium, etc.) means a decrease and / or death of the microorganism and / or a decrease in the growth rate of the microorganism, which reduces the growth or growth of the microorganism. It also includes killing microorganisms.

As used herein, the term "animal" means any human or non-human animal. Non-human animals include, for example, dogs, cats, mice, rabbits, horses, pigs, monkeys, chimpanzees, etc. In one embodiment, the non-human animal can be a pet animal or an ornamental animal.

As used herein, "cosmetics" are worn and worn on the body of an animal (eg, human) to cleanse, beautify, enhance its attractiveness, change its appearance, or keep its skin or hair healthy. Refers to any product intended to be used by rubbing, spraying or similar methods. In the present specification, the “cosmetics” is not limited to “cosmetics” under the so-called Pharmaceutical and Medical Devices Act (former Pharmaceutical Affairs Law), and may be, for example, quasi-drugs, pharmaceuticals, or miscellaneous goods. In this specification, "quasi-drugs" is an intermediate classification between pharmaceuticals and cosmetics as defined in Japan's "Act on Securing Quality, Effectiveness, and Safety of Pharmaceuticals, Medical Devices, etc." , Including those with a mild action on the human body, and also includes machinery and equipment with a gentle action on the human body. Examples of quasi-drugs include medicated cosmetics (including medicated soaps, medicated toothpastes, etc.), bath salts, quasi-drugs for control (insecticides, etc.) and designated quasi-drugs (drinks, mouthwashes, etc.) Quasi-drugs, etc.), but are not limited to these. As used herein, the term "pharmaceutical drug" refers to a drug given to diagnose, treat, or prevent a human or animal disease, and is contained in the Japanese Pharmacy, or a diagnosis or treatment of a human or animal disease. Or those intended for prophylactic use that are not machinery, dental materials, medical or sanitary products (excluding non-pharmaceutical products), and the structure or function of the human or animal body. Includes items intended to affect

In the present specification, any compound and component may be provided in the form of a salt, unless otherwise specified. In particular, any compound and component may include common bases or acids such as phosphoric acid, phobic acid, polyphosphate, hydrochloric acid, sulfuric acid, carbonic acid, aldonic acid, uronic acid, aldanoic acid, alginic acid, gluconic acid, glucuronic acid. , Glucanoic acid, galactal acid, galacturonic acid, benzoic acid, 2,4-dihydroxybenzoic acid, silicic acid, hydroxy acid, cyclohexylcarboxylic acid, tannic acid, lactic acid, tartaric acid, citric acid, gluconic acid, glucoheptonic acid, adipic acid , Hydroxycitic acid, malic acid, fumaric acid, maleic acid, succinic acid, chlorogenic acid, salicylic acid, creatine, glucosamine hydrochloride, glucono-δ-lactone, caffeic acid, bile acid, acetic acid, ascorbic acid, alginic acid, erythorbic acid, poly Glutamic acid, aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid, glutamine, Hydroxyproline, taurine, norvaline, glutathione, sarcosin, poly-L-aspartic acid, ammonia, sodium, potassium, magnesium, calcium, guanidine, glucosamine, poly-L-lysine, poly-L-ornithine, or poly-L-arginine. Can be provided in the form of salts formed with. As used herein, the term "salt formed" of an acid and a base does not require that the salt is actually formed by reacting the acid and the base, but merely in the form of the final substance. Is an expression used to describe.

The term "about" refers to the indicated value plus or minus 10%. "About", when used for temperature, refers to the indicated temperature plus or minus 5 ° C.

(Preferable embodiment)
In one aspect, the present disclosure provides microbial control by spicrysporic acid-related substances. Any means to achieve this is contemplated as the scope of this disclosure. For example, even if there is no explicit description, the description of the method of using a certain ingredient reflects other means such as a composition containing the same ingredient, the use of the same ingredient and the same ingredient for use in the same method. The form is also intended at the same time. Although the present disclosure describes the present disclosure mainly in the embodiment of the composition, the description of the composition for a certain use containing a certain component is described in the method for the same use of the same component and the same component. An embodiment that reflects other means, such as its use, is also intended.

(Spicrisporic acid-related substances)
In one aspect, the present disclosure provides spicrysporic acid-related substances for microbial control. The spicrysporic acid-related substance may be either spicysporic acid or a derivative thereof, a salt thereof, or a mixture thereof. Spikrisporic acid is a natural substance that is less irritating to humans, has excellent biodegradability, and functions as a surfactant. As shown in the examples, the inventors have found that spicrysporic acid-related substances have an inhibitory effect on various bacteria and fungi. Some surfactants are known to have a bacterial inhibitory effect, but many are synthetic, such as benzonicome chloride. In addition, there are few substances that have a fungal inhibitory effect, and it was a particularly unexpected discovery that spicrysporic acid-related substances have an inhibitory effect on various fungi. Although not bound by any particular theory, the microbial inhibitory activity of spicrysporic acid-related substances is that of spicysporic acid (1) carboxyl group, (2) two chiral carbons, and / or (3). It is believed that it is conferred by a combination of long carbon chain moieties and hydrophilic moieties (which may be related to surface activity and microbial affinity for membranes). As shown in the examples, 3 sodium open ring acid (O acid) exhibits weaker microbial inhibitory activity than 1 sodium open ring acid (O acid), and the presence of a carboxyl group may improve the microbial inhibitory activity. Although it was suggested, since the microbial inhibitory activity was still observed even with 3 sodium O acid, it is expected that the contribution is not only the carboxyl group.

式中、
Ｒ^１、Ｒ^２およびＲ^３は、それぞれ独立に、−ＯＲ^Ａ、−ＮＨＲ^Ａまたは−Ｎ（Ｒ^Ａ）_２であり、
Ｒ^４は、−Ｈ、−ＯＨ、−ＯＲ^Ａまたは−ＮＨＲ^Ａであるか、または破線で示される部分に追加の結合を形成することで二重結合を形成し、
ここで、Ｒ^Ａは、１〜２個のカルボキシル基で必要に応じて置換されていてもよい炭素数１〜２１の飽和又は不飽和である分岐または直鎖炭化水素基（例えば、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、イソブチル、ｎ−ペンチル、アリル、オクチル、４−オクテニル、２−オクテニル、２−エチルヘキシル、オレイル、パルミチル、ヘキシル、２−ヘキセニル、１１−ヘキサデセニル、ヘキサデシル、シクロヘキシル、ステアリル、またはゲラニルなど）であるか、または
Ｒ^１、Ｒ^２、Ｒ^３およびＲ^４のうちのいずれか２つは、一緒になって−Ｏ−の架橋を形成していてもよいし、あるいは
２つの分子におけるＲ^１、Ｒ^２、Ｒ^３およびＲ^４のうちのいずれか１つ同士が分子間で連結し、２量体を形成してもよい。 In one embodiment, the spicrysporic acid-related substance of the present disclosure is spicysporic acid represented by the following formula I, a derivative thereof, or a salt thereof.

During the ceremony
R ¹ , R ² and R ³ are independently -OR ^A , -NHR ^A or -N ( ^RA ) ₂ , respectively.
R ⁴ forms -H, -OH, or an -OR ^A, or -NHR ^A, or a double bond at the moiety indicated to form an additional bond by a broken line,
Here, ^RA is a saturated or unsaturated branched or linear hydrocarbon group having 1 to 21 carbon atoms which may be optionally substituted with 1 to 2 carboxyl groups (eg, methyl, ethyl). , N-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, allyl, octyl, 4-octenyl, 2-octenyl, 2-ethylhexyl, oleyl, palmityl, hexyl, 2-hexenyl, 11-hexadecenyl, hexadecyl, cyclohexyl , stearyl or a geranyl, etc.), or any two of ^{R 1,} R 2, ^{R 3} and ^{R 4,} may form a bridge of together -O-, Alternatively, any one of R ¹ , R ² , R ³ and R ^{4 in} the two molecules may be linked between the molecules to form a dimer.

からなる群から選択される化合物またはその塩である。好ましい実施形態において、本開示のスピクリスポール酸関連物質は、Ｏ酸またはＤ酸あるいはその塩であり、高い微生物抑制能力および／または高い有機溶媒溶解性を有し得る。 In a specific embodiment, the spicrysporic acid-related substances of the present disclosure are:

A compound or a salt thereof selected from the group consisting of. In a preferred embodiment, the spicrysporic acid-related material of the present disclosure is an O-acid or a D-acid or a salt thereof, which may have high microbial control ability and / or high organic solvent solubility.

で表される構造を有する少なくとも１つの部分を含み、式中、
Ｃ_１０Ｈ_２１は、直鎖状の飽和炭素鎖を表し、
−Ｘ^１−および−Ｘ^２−は、それぞれ独立に、−Ｏ−、−Ｓ−および−ＮＨ−からなる群から選択され、
−Ｙ−は、それぞれ独立に、炭素を含む２価のリンカー基であり、
Ｒ^１は、それぞれ独立に、−Ｈ、−ＯＨ、−ＯＲ^Ａまたは−ＮＨＲ^Ａであるか、または破線で示される部分に追加の結合を形成することで二重結合を形成し、
Ｒ^２は、それぞれ独立に、−ＯＨ、−ＯＲ^Ａ、−ＮＨＲ^Ａまたは−Ｎ（Ｒ^Ａ）_２であり、
ｎは、それぞれ独立に、１以上の整数であり、
ここで、Ｒ^Ａは、１〜２個のカルボキシル基で必要に応じて置換されていてもよい炭素数１〜２１の飽和又は不飽和である分岐または直鎖炭化水素基（例えば、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、イソブチル、ｎ−ペンチル、アリル、オクチル、４−オクテニル、２−オクテニル、２−エチルヘキシル、オレイル、パルミチル、ヘキシル、２−ヘキセニル、１１−ヘキサデセニル、ヘキサデシル、シクロヘキシル、ステアリル、またはゲラニルなど）である。式Ｂの構造は、（１）カルボキシル基、（２）２つのキラル炭素、および（３）長鎖炭素鎖部分と親水性部分との組み合わせを含むことができ、式Ａの構造は、（２）２つのキラル炭素、および（３）長鎖炭素鎖部分と親水性部分との組み合わせを含むので、式Ｂの構造および式Ａの構造はいずれも、微生物抑制活性を有すると予測される。 In one embodiment, the spicrysporic acid-related material of the present disclosure is a spicysporic acid-derived polymer or a salt thereof. In one embodiment, the spicrysporic acid inducible polymers of the present disclosure are of formula A or formula B.

Containing at least one portion having a structure represented by, in the formula,
C ₁₀ H ₂₁ represents a linear saturated carbon chain.
-X ^1- and -X ² --are independently selected from the group consisting of -O-, -S- and -NH-, respectively.
-Y- is a divalent linker group containing carbon independently of each other.
R ¹ is, independently, formed -H, -OH, or an -OR ^A, or -NHR ^A, or a double bond at the moiety indicated to form an additional bond by a broken line,
R ² are independently -OH, -OR ^A , -NHR ^A or -N ( ^RA ) ₂ , respectively.
n is an integer of 1 or more independently of each other.
Here, ^RA is a saturated or unsaturated branched or linear hydrocarbon group having 1 to 21 carbon atoms which may be optionally substituted with 1 to 2 carboxyl groups (eg, methyl, ethyl). , N-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, allyl, octyl, 4-octenyl, 2-octenyl, 2-ethylhexyl, oleyl, palmityl, hexyl, 2-hexenyl, 11-hexadecenyl, hexadecyl, cyclohexyl. , Stearyl, or geranyl, etc.). The structure of formula B can include (1) a carboxyl group, (2) two chiral carbons, and (3) a combination of a long chain carbon chain moiety and a hydrophilic moiety, and the structure of formula A is (2). ) Two chiral carbons, and (3) a combination of a long-chain carbon chain moiety and a hydrophilic moiety, both the structure of formula B and the structure of formula A are expected to have microbial inhibitory activity.

In one embodiment, -Y- in formulas A and / or B comprises 1-10 carbon atoms and 0-6 heteroatoms selected from the group consisting of O, S and N. , A straight or branched divalent linker group containing 1 to 6 double bonds and / or 1 to 2 triple bonds as required, and optionally in any number. Hydrogen may be replaced by fluorine. In one embodiment, -Y- comprises a 4- to 7-membered aromatic or non-aromatic ring, optionally containing 1-2 heteroatoms selected from the group consisting of O, S and N. It may or may not be included. In one embodiment, -Y- may or may not contain one or two carboxyl groups. In one embodiment, -Y- refers to COC, CSC, COC = O, O = COC, CNC = O and O = C. It may or may not include one or more substructures selected from the group consisting of −NC. In one embodiment, -Y- _{^{is, -CH 2 -Y A -CH 2 -}} , - C (= O) -Y A -CH 2 -, - CH 2 -Y A -C (= O) - or ^{-C (= O) -Y a -C} (= O) - structure can have a (-Y ^a - moiety that may be included in the above -Y-). In one embodiment, -Y- is a divalent linear saturated linker group containing 1-10 carbon atoms.

In one embodiment, the spicrysporic acid inducible polymer of the present disclosure may comprise one or more moieties represented by formula A and / or one or more moieties represented by formula B. For example, when spicrysporic acid and 1,3-propanediol are mixed and subjected to appropriate dehydration conditions, a spicysporic acid-derived polymer containing a portion of formula A can be formed, and when further hydrolyzed, n Smaller values of the spicrysporic acid-derived polymer and the spicysporic acid-induced polymer containing the A and B moieties can be formed.

In one embodiment, the spicrysporic acid-derived polymers of the present disclosure are ethylene, propylene, styrene, urethane, tetrafluoroethylene, acrylonitrile butadiene styrene, acrylonitrile styrene, phenylensulfide, cyclic olefins, carbonates, amides, oxymethylene, and. It may include a unit structure used in a general resin such as styrene. In one embodiment, the spicrysporic acid inducible polymers of the present disclosure are used in the preparation of common resins such as vinyl acetate, lactic acid, acrylic acid, methacrylic acid, vinyl chloride, formaldehyde, urea, melamine, epoxides, and phenols. It may be formed together with the monomer to be formed.

In one embodiment, n in formulas A and / or B can be an integer greater than or equal to 1 (eg, 1-100, 1-1000, 1-1000, etc.), and those skilled in the art will appropriately value n. Can be controlled. For example, when spicrysporic acid and ethylenediamine are mixed and subjected to appropriate dehydration conditions, a spicysporic acid-derived polymer containing a portion of formula A having a large value of n can be formed. For example, when spicrysporic acid, open ring acid, phthalic acid and ethylenediamine are mixed and subjected to appropriate dehydration conditions, a random copolymer containing a portion of formula A, a portion of formula B and a portion of phthalic acid amide is formed and has a small value. A spicy phthalic acid inducible polymer having n of can be formed.

In one embodiment, the spicrysporic acid inducible polymers of the present disclosure may be crosslinked. Cross-linking may be carried out, for example, by adding any suitable cross-linking agent after or during the formation of the spicrysporic acid inducible polymer of the present disclosure, or an already cross-linked spicrysporic acid derivative (eg, dimer). It may be carried out by mixing a quantified spicrysporic acid derivative) to form a polymer.

The spicrysporic acid-derived polymer of the present disclosure is, for example, a divalent divalent containing spicysporic acid represented by the above formula I or a derivative thereof or a salt thereof and carbon represented by -Y- in the above formula A or B. It can be prepared by subjecting a mixture containing a bifunctional reagent containing a linker group to an appropriate chemical reaction (for example, dehydration condensation). In addition, the spicrysporic acid-induced polymer having the structure of formula A can be converted into the spicysporic acid-induced polymer having the structure of formula B through a hydrolysis reaction and / or an appropriate addition reaction, and similarly, the spicrysporic acid-induced polymer having the structure of formula B can be converted. It is also possible to convert from to equation A.

In one embodiment, the spicrysporic acid inducible polymers of the present disclosure are any resin (eg, ethylene, propylene, styrene, urethane, tetrafluoroethylene, acrylonitrile butadiene styrene, acrylonitrile styrene, phenylensulfide, cyclic olefin, carbonate, etc. General resins formed as monomers such as general resins containing unit structures such as amide, oxymethylene, and urethane, vinyl acetate, lactic acid, acrylic acid, methacrylic acid, vinyl chloride, formaldehyde, urea, melamine, epoxide, and phenol. Resins, polysulfones, polyether sulfones, polyether ether ketones, polyimides, polyamideimides, modified polyphenylene ethers, and common resins such as polyesters) may be formed. For example, the spicrysporic acid-derived polymer of the present disclosure may be mixed with another resin and molded, or may be placed on the surface of another resin. Since the spicrysporic acid-induced polymer of the present disclosure can exhibit microbial inhibitory activity when a portion of the formula A or B comes into contact with a microorganism, the spicysporic acid of the present disclosure is at least partially when molded together with another resin. It is preferable that the acid-induced polymer is molded so as to appear on the surface.

In one embodiment, the spicrysporic acid-derived polymers of the present disclosure have a molecular weight of at least 1%, at least 2%, at least 5%, at least 10% of the total molecular weight of the portions represented by formulas A and B. It can account for at least 15%, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, or at least 95%. This molecular weight ratio can be determined by any suitable method. For example, the spicrysporic acid-induced polymer of the present disclosure can produce spicysporic acid or a spicysporic acid derivative of the present disclosure (for example, a derivative represented by the formula I) by hydrolysis treatment, so that a part of the polymer is taken out. This molecular weight ratio can be calculated by measuring the amount of spicrysporic acid or spicysporic acid derivative produced by hydrolyzing this and comparing it with the weight of a part taken out. For example, when the spicrysporic acid-derived polymer of the present disclosure is molded with another resin to form a polymeric material, it is homogeneous in a homogeneous portion of the polymeric material (eg, physical or chemical properties such as crystallinity). The part) may be taken out and hydrolyzed with respect to this part as described above to calculate the molecular weight ratio, and this value may be used as the above molecular weight ratio of the spicrysporic acid-derived polymer of the present disclosure.

In one embodiment, the spicrysporic acid-related substances of the present disclosure, which are salts, are spicysporic acid or a derivative thereof of the present disclosure and sodium, potassium, lithium, magnesium, calcium, ammonia, monoethanolamine, diethanolamine, triethanol. It can be a salt formed in combination with a base selected from amines, guanidine, arginine, lysine and combinations thereof.

(Microbial inhibitor)
In one aspect, the disclosure provides a microbial inhibitor containing the spicrysporic acid-related substances described herein. In one embodiment, the microbial inhibitor suppresses microorganisms, including bacteria. In one embodiment, the microbial inhibitor suppresses microorganisms, including fungi. In one embodiment, the microbial inhibitors are from the genus Escherichia, the genus Methylobacterium, the genus Micrococcus, the genus Pseudomonas, the genus Staphylococcus, the genus Serratia, the genus Rhodotorula, the genus Aspergillus, It suppresses microorganisms, including microorganisms selected from the genera Trichoderma, Alternaria, Aureobasideium and Ulocradium.

As a microorganism of the genus Escherichia, E. Albertii, E.I. colli, E.I. fergusoni, E.I. hermannii, E.I. marmotae, E.I. vulneris and E.I. Marmotae can be mentioned.

As a microorganism of the genus Methylobacterium, Methylobacterium. adhaesivum, M. et al. aerolatum, M. et al. aminovorans, M.D. Aquaticum, M. et al. Brachiatum, M. et al. Brachythecii, M.D. bullatum, M. et al. cerastii, M. et al. dankookense, M.D. extorquens, M. et al. frigidaeris, M. et al. Fujisawaense, M.D. gnafalii, M. et al. goesingense, M.D. gossipicola, M. et al. Gregans, M.D. haplocradii, M. et al. chrysocolla, M. et al. inners, M.D. isbiliense, M.I. jetgali, M. et al. komagatae, M. et al. longum, M. longum. Marchantiae, M. et al. mesophilicum, M. et al. nodulans, M. et al. organophilum, M. et al. oryzae, M. et al. oxalidis, M. et al. persicinum, M. et al. phyllosphaerae, M. et al. phyllostachyos, M. et al. Platani, M. et al. podalium, M. et al. populi, M. et al. pseudosasae, M. et al. pseudosasicola, M. et al. radiotolerans, M.D. rhodesianum, M. et al. rhodinum, M. et al. salsuginis, M. et al. solo, M.M. suomiense, M.D. tardum, M.D. tarhaniae, M.D. thiocyanatum, M. et al. turgingiense, M.D. trifolia, M. et al. Variable and M.V. Zatmanii can be mentioned.

As a microorganism of the genus Micrococcus, M. aloeverae, M. et al. antarcticus, M. et al. cohnii, M.M. endophysicus, M. et al. flavus, M. et al. lactis, M. et al. luteus, M. et al. lylae, M. et al. Muciliaginosis, M. et al. roseus, M. et al. terreus, M.D. Mortus and M.M. yunnanensis can be mentioned.

As a microorganism of the genus Pseudomonas, P. aeruginosa, P. et al. Alcaligenes, P. et al. angulariseptica, P. et al. Argentinensis, P.M. borbori, P.M. citronellolis, P. et al. flavescens, P.M. mendocina, P.M. nitroreducens, P.M. oleovorans, P. et al. pseudoalcalines, P. et al. resinovorans and P.M. Straminea can be mentioned.

As a microorganism of the genus Staphylococcus, S. Argenteus, S.A. arlettae, S.A. Agnetis, S.A. aureus, S.A. auricalis, S.A. caeli, S.M. capitis, S.A. caprae, S.A. carnosus, S. et al. caseolyticus, S.A. Chromogenes, S.A. cohnii, S.M. cornubiensis, S. et al. condimenti, S.A. debucchii, S.A. delphini, S.M. devriesei, S.M. edaphicus, S.A. epidermidis, S. cerevisiae. equiorum, S. et al. felt, S.M. fleurettii, S.A. Gallinarum, S. haemolyticus, S.A. hominis, S.M. hyicus, S.A. intermediaus, S.M. jettensis, S. et al. kloosii, S.M. Leei, S.M. lentus, S.M. rugdunenis, S.M. lutrae, S.M. Lyticans, S.A. massiliensis, S.A. microti, S.M. Muscae, S.M. nepalensis, S.A. pasteuri, S.A. petrasii, S. et al. pettenkoferi, S. et al. picifermentans, S.A. pseudintermedius, S. et al. pseudorugdunensis, S. et al. Pulveri, S.M. rostri, S. ram saccharoliticus, S.A. staphylococcus, S. Schleiferi, S.M. schweitzeri, S.A. sciuri, S.M. simiae, S.M. simulans, S.M. stepanovicii, S.A. succinus, S.M. Vitulinus, S.A. warneri and S.M. xylosus can be mentioned.

As a microorganism belonging to the genus Serratia, S. aquatis, S.A. entomophila, S.A. ficaria, S. et al. focala, S.A. glossinae, S.A. grimesi, S.M. liquefaciens, S.A. marcescens, S.A. myotis, S.I. nematodiphila, S.A. odorifera, S.A. Primusica, S.A. proteamaculans, S.A. quinivorans, S.M. rubidaea, S.M. symbiotica, S.A. ureilitica and S. Vespertilionis can be mentioned.

As a microorganism of the genus Rhodotorula, R. acheniorum, R. et al. acta, R.M. araucariae, R. et al. Armeniaca, R. aurantiaca, R. et al. auriculariae, R. et al. bacarum, R. et al. benthica, R.M. biourgei, R.M. bogoriensis, R. et al. bronchialis, R. et al. buffonii, R.M. calliptogenae, R. et al. cladiensis, R. et al. cresolica, R. et al. crossa, R. et al. Cycloclastica, R. et al. evergladiensis, R. et al. ferulica, R.M. foliorum, R. et al. Fragaria, R. et al. Fujisanensis, R.M. futronensis, R. et al. gelatinosa, R. et al. glacialis, R. et al. glutinis, R. et al. gracilis, R. et al. gramnis, R. et al. grinbergsii, R. et al. Himalayensis, R.M. Hinnulea, R.M. histolytica, R. et al. hypofila, R. et al. incarnata, R. et al. ingeniosa, R. et al. javanica, R. et al. koishikawensis, R.M. lactosa, R. et al. lamellibraciae, R. et al. laringis, R. et al. lignophila, R. et al. lini, R.M. longissima, R. et al. ludwigii, R.M. lysinophila, R. et al. marina, R.M. matritensis, R. et al. meli, R.M. Minute, R.M. Mucilaginosa, R.M. nitens, R. et al. notofagi, R. et al. oryzae, R. et al. Pacifica, R. et al. parlida, R. et al. fililla, R. et al. pilimanae, R.M. pinicola, R. et al. Psychrophenolica, R. et al. psychophila, R. et al. pustule, R. et al. retinophila, R. et al. rosulata, R. et al. rubra, R.M. rubrorugosa, R. et al. silvestris, R. et al. sinensis, R. et al. slofiae, R.M. sonkii, R.M. straminea, R. et al. Subericola, R.M. terpenoidalis, R. et al. terrea, R.M. Tokyoensis, R.M. ulzamae, R.M. vanillica, R.M. Villeminii, R.M. Yarrowii, R.M. yunnanensis and R. ZZoltyi can be mentioned.

As a microorganism of the genus Aspergillus, A. aculeatus, A.I. awamori, A. caesielrus, A.I. candius, A.I. carneus, A. clavatus, A.I. deflectus, A.I. Fischerianus, A.I. flavus, A.I. fumigatus, A.I. Glaucus, A. et al. nidulans, A.I. niger, A. ochraceus, A. oryzae, A. parasiticus, A. et al. penicilloides, A.I. restrictus, A.I. sojae, A. so. sysdowii, A.I. Tamarii, A.M. terreus, A. ustus and A. Versicolor can be mentioned.

As a microorganism of the genus Penicillium, P. albocoremium, P. et al. aurantiogriseum, P. et al. biliae, P.M. camemberti, P. et al. candium, P.I. chrysogenum, P. et al. claviforme, P.M. community, P.M. crustosum, P. et al. digitatum, P. et al. echinulatum, P. et al. expansum, P.I. funiculosum, P.M. grabrum, P. et al. glaucum, P. et al. imranianum, P.I. italicum, P. et al. lacussarmientei, P.M. purpurogenum, P. et al. roqueforti, P.M. stoloniferum, P. et al. ulaiense, P.M. verrucosum and P. et al. Viridicatum can be mentioned.

As a microorganism of the genus Scorecobasidium, S. Constrictum, S.A. humicola, S.A. terreum and S. tsshawytschee can be mentioned.

As a microorganism of the genus Exophiala, E.I. alcalophila, E.I. Angulospora, E.I. attenuata, E.I. calicioides, E.I. castellani, E.I. dermatitidis, E.I. dopicola, E.I. E. e, E. heteromorpha, E.I. Hongkongensis, E.I. Jeanselmei, E.I. lecanii-corni, E.I. mansoni, E.I. mesofila, E.I. moniliae, E.I. Negroni, E.I. phaeomuriformis, E.I. piciphila, E.I. psychophila, E.I. salmonis, E.I. spinifera and E.I. werneckii can be mentioned.

As a microorganism of the genus Cladosporium, C.I. cladosporioides, C.I. cucumerinum, C.I. herbarum, C.I. oxysporum and C.I. Sphaerospermum can be mentioned.

As a microorganism of the genus Phoma, P. caricae, P.M. clematidina, P. et al. Costaricensis, P.M. cucurbitacearum, P.M. desertiva, P.M. draconis, P. et al. eupylena, P. et al. herbarum, P.M. insidoosa, P.M. microspore, P.I. Narcissi, P. et al. nebulosa, P.M. oncidi, P.M. pinodella, P.I. scabra, P. et al. scrollioides, P.M. strasseri, P.M. tracheipila, P. et al. multilostrata, P.M. dauci, P.M. exiga, P.M. glomerata, P.M. licopersici, P.M. lingum, P.M. Macrostoma can be mentioned.

As a microorganism belonging to the genus Trichoderma, T.I. alutaceum, T. et al. asperellum, T.I. brevicompactum, T.I. cattron, T.I. cerebriforme, T.I. citrinoviride, T.I. citrinum, T.I. cornu, T.I. Dingleyea, T.I. dorotheae, T.I. effusum, T.I. erinaceum, T. et al. estnicum, fertile, T. et al. T. gelatinosum, T.I. hamateum, T.I. harzianum, T.I. Koningii, T.K. longibraciatum, T.I. lixii, T.I. ovalisporum, T. et al. paucisporum, T. et al. Petereseni, T. et al. piliferum, T. et al. pseudokoningii, T.I. Pubessens, T. et al. Pleuroticola, T.I. pelletum, T.I. purvinatum, T.I. songyi, T.M. stromaticum, T.I. theobromicola, T.I. virens, T.I. Viridian can be mentioned.

As a microorganism of the genus Alternaria, A.I. alternata, A. tomato, A. solani, A. Classicola, A. et al. brassicae, A.I. japonica, A.I. cucumerina, A.I. spiniae, A.I. dauci, A. porri, A. petatisis, A. et al. nelumbi, A.I. Radicina can be mentioned.

As a microorganism of the genus Aureobasidium, A. pullulans, A.I. melanogenum, A. et al. namibiae, A.I. Subglacial is mentioned.

As a microorganism of the genus Ulocradium, U.S.A. Botrytis, U.C. atrum, U.S.A. Alternariae, U.S.A. Botrytis, U.C. chartarum, U.S.A. chalamydosporum, U.S.A. consider, U.S.A. cucurbitae, U.S.A. dauci, U.S.A. runuginosum, U.S.A. lithium, U.S.A. manihoticola, U.S.A. manihoticolum, U.S.A. microspore, U.S.A. multiforme, U.S.A. oblongo, U.S.A. ovoideum, U.S.A. odemansi, U.S.A. populi, U.S.A. septosporum, U.S.A. Tuberculatum can be mentioned.

In one embodiment, the microbe inhibitor, Escherichia coli, Methylobacterium aquaticum, Micrococcus luteus, Pseudomonas aeruginosa, Staphylococcus aureus, Serratia marcens, Rhodotorula mucillaginosa, Aspergillus nigar, Penicillium citrinum, selected from Scolecobasidium constrictum, Exophiala salmonis, and Cladosporium Cladosporioides Suppresses microorganisms including staphylococcus aureus.

In one embodiment, the microbial inhibitors of the present disclosure may comprise any suitable proportion of the spicrysporic acid-related substances of the present disclosure, eg, about 0.001% by weight, about 0.002% by weight, about. 0.005% by weight, about 0.01% by weight, about 0.02% by weight, about 0.05% by weight, about 0.1% by weight, about 0.2% by weight, about 0.5% by weight, about 1 %%, About 2% by weight, about 5% by weight, about 10% by weight, about 20% by weight, about 50% by weight, about 70% by weight, about 80% by weight or about 90% by weight, or any two of these. It can be included as a percentage of the range represented by the combination of values.

The microorganism inhibitor of the present disclosure may be in any form, and for example, oil-in-water (O / W) type, water-in-oil (W / O) type, W / O / W type, O / W / O. Examples include suspensions such as molds, solids, liquids, powders, jellies, pastes, and sheets. In a specific embodiment, the microbial inhibitors of the present disclosure are in solution or paste form and are applied to the subject by spraying, spraying or coating.

The microbial inhibitors of the present disclosure may be supplemented with any additional ingredients or additives, such as oily bases, moisturizers, surfactants, thickeners, solvents, propellants, antioxidants, reductions. Agents, oxidants, preservatives, chelating agents, pH regulators, powders, inorganic salts, UV absorbers, vitamins, anti-inflammatory agents, blood circulation promoters, hormones, anti-wrinkle agents, anti-aging agents, tightening agents , Cold sensitizer, warming agent, wound healing promoter, irritation palliative, analgesic, cell activator, plant / animal / microbial extract, antipruritic, keratin exfoliating / dissolving agent, antiperspirant, refreshing agent, astringent Agents, enzymes, nucleic acids, fragrances, pigments / colorants / dyes / pigments and the like may be added. In one specific embodiment, the microbial inhibitors of the present disclosure may comprise metal components such as copper, silver, zinc, cobalt, nickel or salts thereof. Although not bound by any theory, the spicrysporic acid-related substances described herein may have chelating ability, so that the metal component is coordinate-bonded to the spicy-sporic acid-related substance and is stable. Can result in improved chelation and / or microbial inhibitory activity.

(Use)
The spicysporic acid-related substances or microbial inhibitors of the present disclosure can be used for various purposes. Since the spicrysporic acid-related substance of the present disclosure can be hypoallergenic to animals such as humans, it can be suitably used for articles that come into contact with the skin and mucous membranes of animals such as humans. Further, since the spicrysporic acid-related substance of the present disclosure can have a high surface bonding force, it can be applied to the surface of various materials such as a metal surface and a plastic surface to exert an effect, and is safe because it is a natural substance. It is considered that the environmental load due to the residual is low. For example, detergents, disinfectant supplies (eg, disinfectant wipes), antibacterial supplies (eg, antibacterial cream), hygiene products (eg, masks, gauze, bandages, adhesive plasters), water supplies (eg, baths, washbasins, tubs). , Bandages, bathroom fixtures, toilet fixtures, towels), antibacterial agents, pharmaceuticals, non-pharmaceutical products, cosmetics, the spicysporic acid-related substances of the present disclosure may be beneficially used. In addition, the microbial inhibitor containing the spicrysporic acid-related substance of the present disclosure exhibits symptoms that may be related to skin bacteria such as water bug, eczema, dermatitis, xeroderma, urticaria, atopy, acne, armpit, and dandruff. Alternatively, it can be applied to a subject who may present it to improve or prevent its symptoms. The spicysporic acid-related substances of the present disclosure may also be used in building materials (eg, floors, wallpaper, walls, pillars, doors), filters (eg, air filters), animal (eg, livestock) articles, and the like. can. In a specific embodiment, the microbial inhibitors of the present disclosure are bathroom and / or toilet liquid detergents (eg, for spray application). In another specific embodiment, the microbial inhibitor of the present disclosure is an antiperspirant.

In one embodiment, the cosmetics, pharmaceuticals or non-pharmaceutical products containing the spicrysporic acid-related substances of the present disclosure include, for example, basic cosmetics (skin care cosmetics), finishing cosmetics (makeup cosmetics), bathing agents, perfumes, hair care products. (Hair tonics, shampoos, conditioners, conditioners, hair dyes, etc.), toothpaste, skin oil suppressants, soaps, odecolons, deodorants, baby powders, control agents (insecticides, etc.), but are not limited to these. Basic cosmetics include lotions, emulsions, wash pigments, serums, creams (eg hand creams, lip balms, sunscreens), aftershave lotions, shaving soaps, shaving oils, chemical peels, facial masks, etc. , Not limited to these. Finishing cosmetics include foundation, eyebrow, mascara, eyeshadow, eyeline, lipstick, gloss, teak, white powder, manicure, pedicure, concealer, dolan, nose shadow, eye petit, eyelashes, lipstick, lip gloss, lip liner, etc. However, it is not limited to these.

Since the spicysporic acid-related substances of the present disclosure can also suppress fungi, articles exposed to high humidity environment (for example, building materials for bathrooms such as tiles and packing, and clothing such as masks, shoes, socks, underwear and gloves). ) Etc. can also be used. In one embodiment, the spicrysporic acid-derived polymers described herein or polymeric materials comprising them may be used for these articles.

In one embodiment, the spicysporic acid-related substances of the present disclosure are: Escherichia, Methylobacterium, Micrococcus, Pseudomonas, Staphylococcus, Serratia, Rhodotorula, Asperu Since it may have the ability to suppress at least one of the genera, Phoma, Trichoderma, Alternaria, Aureobasideium and Ulocradium, it is suitable for articles in which it may be advantageous to suppress these microorganisms. Can be used.

In one embodiment, the spicrysporic acid-related substances of the present disclosure can suppress microorganisms that can attach to foods such as Escherichia coli, Micrococcus luteus, and Tupperwareccus aureus and cause infectious diseases, so that articles in contact with foods (for example, for example). Kitchenettes, cutting boards, noodle sticks, corks, aluminum foil, wraps, wraps, cups, tableware, tongs, trays, pouches, tappers, cooking sheets, lunch boxes, chopstick holders) and table products (eg table cloths, table cloths, pouches) , Tappers, cooking sheets, lunch boxes, chopstick holders).

(Method)
In one aspect, the disclosure provides a method for controlling a microorganism, comprising the step of applying the spicrysporic acid-related material described herein to a subject. The target may be an animal such as a human, or an article that can come into contact with an animal such as a human (for example, the above-mentioned article). The application may be any method such as spraying, mixing and spreading.

As used herein, "or" is used when "at least one" of the matters listed in the text can be adopted. The same applies to "or". When "within a range" of "two values" is specified in the present specification, the range also includes the two values themselves.

References such as scientific literature, patents, and patent applications cited herein are incorporated herein by reference in their entirety to the same extent as each specifically described.

The present invention has been described above with reference to preferred embodiments for ease of understanding. Hereinafter, the present invention will be described based on examples, but the above description and the following examples are provided for purposes of illustration only and not for the purpose of limiting the present invention. Therefore, the scope of the present invention is not limited to the embodiments or examples specifically described in the present specification, but is limited only by the claims.

Examples are described below.
(Example 1)
The effects of spicrysporic acid (S acid) on various microorganisms were tested.

The microorganisms tested were:
Bacteria Escherichia coli NBRC 3972 (E. coli)
・ Methylobacterium aquaticum NBRC 106537 (Methylobacterium)
・ Micrococcus luteus NBRC 13867 (Micrococcus luteus)
・ Pseudomonas aeruginosa NBRC 13275 (Pseudomonas aeruginosa)
・ Staphylococcus aureus NBRC 12732 (Staphylococcus aureus)
・ Serratia marces NBRC 16347 (Serratia marcescens)
・ Rhodotorula mucillaginosa NBRC 0382 (Rhodotorula muchiraginosa)

Fungus / Aspergillus niger NBRC 105649 (Aspergillus niger)
・ Chaetomium globosam NBRC 6347 (Chaetomium)
The medium components in the table below were weighed and then dissolved in ion-exchanged water. The pH of Medium B was adjusted to 7.0. Then, each medium was prepared by sterilizing in an autoclave. About 20 mL of each medium was aseptically dispensed into a 9 cm petri dish and solidified to prepare a plate medium.

Bacteria (Escherichia coli, Methylobacterium aquaticum, Micrococcus luteus, Pseudomonas aeruginosa, Staphylococcus aureus, Serratia marcens and Rhodotorula mucillaginosa) is bacteria are bacteria number concentration using sterile water was prepared to be about ¹⁰ 4 to 10 ⁶ cells / mL 1 mL of the body suspension was added dropwise to the medium and applied to the entire surface.

For fungi (Aspergillus niger, Chaetomium globosam NBRC 6347), ^{1 mL of a spore suspension prepared to a spore concentration of about 10 4} to 10 ⁶ cells / mL using sterile water was added dropwise to the medium and applied to the entire surface. ..
-Strain Escherichia coli NBRC 3972 using medium A

-Strain Serratia marcences NBRC 16347 using medium B
Pseudomonas aeruginosa NBRC 13275
Micrococcus luteus NBRC 13867
Staphylococcus aureus NBRC 12732
Methylobacterium aquaticum NBRC 106537

-Strain Chaetomium globosam NBRC 6347 using medium C
Aspergillus niger NBRC 105649
Rhodotorula mucillaginosa NBRC 0382
Then, 0.5 g of S acid powder was added to the center of the surface of the medium. After culturing at 30 ° C. (bacteria) or 26 ° C. (fungi) for 7 or 13 days, the growth status of microorganisms was confirmed.

The results are shown in FIGS. 1 and 2. S acid showed an inhibitory effect on all the microorganisms tested. In particular, it was unexpected that an inhibitory effect on fungi was observed.

(Example 2)
The test was carried out using open ring acid (O acid), which is a derivative of spicrysporic acid, instead of spicysporic acid.
(Plate medium test)
The test on the plate medium was performed as follows. A 1 mL sample solution (water, 1 wt% aqueous solution of 1 sodium O acid, and 1 wt% aqueous solution of 3 sodium O acid, respectively) was applied to the entire surface of the plate medium prepared in the same manner as in Example 1. Next, 1 mL of a spore suspension of Aspergillus niger NBRC 105649 (Aspergillus niger) prepared in the same manner as in Example 1 was applied to the entire surface of the medium. After culturing at 26 ° C. for 40 hours, the growth status of the bacterial cells was confirmed.

The results are shown in FIG. Suppression of Aspergillus niger was observed in the sample to which O acid was added, as compared with the control sample to which O acid was not added. In addition, the sample to which the monosodium O acid salt was added showed stronger suppression of Aspergillus niger than the sample to which the trisodium O acid salt was added.
(Suspension test)
The test on the suspension was performed as follows. 0.5 g / L, 1 g / L in liquid medium (tryptone (Wako Pure Chemical Industries, Ltd.) 10.0 g / L, yeast extract (Oriental Yeast Co., Ltd.) 5.0 g / L, sodium chloride (Wako Pure Chemical Industries, Ltd.) 10.0 g / L) O acid was added at concentrations such as L, 3 g / L, and 5 g / L. Next, 1 piece of Escherichia coli (Escherichia coli) prepared in the same manner as in Example 1 was inoculated into 2.5 mL of the liquid medium with a loop loop, and the cells were cultured with shaking at 30 ° C. and 150 rpm for 16 hours, and then the cells grew. I confirmed the situation.

The results are shown in FIG. Efficient suppression of E. coli was observed in samples supplemented with 3 g / L or 5 g / L of O acid.

As described above, various spicrysporic acid derivatives show an inhibitory effect on various microorganisms.

(Example 3)
The microbial inhibitory activity of spicrysporic acid and spicysporic acid derivatives was compared with known antibacterial substances.
(Plate medium test)
The test on the plate medium was performed as follows. 1 mL of a spore suspension of Aspergillus niger NBRC 105649 (Aspergillus niger) adjusted to ^{have a spore concentration of about 10 4} to 1 ⁶ cells / mL was applied to the entire surface of the plate medium prepared in the same manner as in Example 1. .. Then, 0.5 g of powder of S acid, O acid or D acid, or tea extract (Access One), wasabi extract (Kinjirushi wasabi) or chitosan (Yaegaki Fermentation Giken) was added to the center of the medium surface. After culturing at 26 ° C. for 10 days, the growth status of microorganisms was confirmed.

The results are shown in FIG. Suppression of Aspergillus niger was observed in the samples to which S acid, O acid, and D acid were added, as compared with the control sample to which no drug was added. In addition, the sample to which O acid was added showed the strongest inhibitory effect, followed by the effect of S acid. Although not intended to be bound by theory, the greater the number of carboxyl groups, the stronger the microbial inhibitory effect. On the other hand, no inhibitory effect on Aspergillus niger was observed in the samples to which tea extract, wasabi extract and chitosan, which are natural substances known to have antibacterial activity, were added. It has been found that spicrysporic acid or spicysporic acid derivatives exhibit superior microbial control ability than known antibacterial natural substances.

(Example 4)
A spicrysporic acid-induced polymer was synthesized.

Specifically, to N, N-dimethylformamide (Tokyo Chemical Industry), spicrysporic acid (Iwata Chemical Industry) and (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (Tokyo Chemical Industry) are added to 120 The reaction was carried out at ° C. for 3 hours to obtain the desired polymer.

(Note)
As described above, the present invention has been illustrated using the preferred embodiments of the present invention, but it is understood that the scope of the present invention should be interpreted only by the scope of claims. The patents, patent applications and documents cited herein are to be incorporated by reference in their content as they are specifically described herein. Understood.

The present disclosure can be applied to various daily necessities, cosmetics, etc., and can provide an improvement in a hygienic environment.

Claims (10)

Microbial inhibitors, including spicrysporic acid-related substances. The microorganism inhibitor according to claim 1, wherein the microorganism contains a bacterium. The microorganism inhibitor according to claim 1, wherein the microorganism contains a fungus. Wherein the microorganism, Escherichia genus, Methylobacterium spp, Micrococcus spp, Pseudomonas spp, Staphylococcus spp, Serratia spp, Rhodotorula spp, Aspergillus spp, Penicillium spp, Scolecobasidium spp, Exophiala spp, Cladosporium sp, Phoma spp, Trichoderma spp, Alternaria spp, Aureobasidium The microbial inhibitor according to claim 1, which comprises a genus and a genus selected from the genus Ulocradium. The spicrysporic acid-related substance is the formula I.

(During the ceremony,
R ¹ , R ² and R ³ are independently -OR ^A , -NHR ^A or -N ( ^RA ) ₂ , respectively.
R ⁴ forms -H, -OH, or an -OR ^A, or -NHR ^A, or a double bond at the moiety indicated to form an additional bond by a broken line,
Here, ^RA is a saturated or unsaturated branched or linear hydrocarbon group having 1-21 carbon atoms, which may be optionally substituted with 1-2 carboxyl groups, or R. ^{1, R} 2, ^{R 3} and any two of ^{R 4} may be optionally form a bridge of together -O- ^R 1 or at the two ^molecules,, R 2, ^{R 3} and any one among of R ⁴ is connected between the molecules, it may form a dimer)
The microorganism inhibitor according to any one of claims 1 to 4, which comprises the compound represented by (1) or a salt thereof. The spicysporic acid-related substance is

The microorganism inhibitor according to any one of claims 1 to 4, which comprises a compound selected from the group consisting of or a salt thereof. The spicrysporic acid-related substance is Formula A or Formula B.
Formula A or formula B

(During the ceremony,
C ₁₀ H ₂₁ represents a linear saturated carbon chain.
-X ^1- and -X ² --are independently selected from the group consisting of -O-, -S- and -NH-, respectively.
-Y- is a divalent linker group containing carbon independently of each other.
R ¹ is, independently, formed -H, -OH, or an -OR ^A, or -NHR ^A, or a double bond at the moiety indicated to form an additional bond by a broken line,
R ² are independently -OH, -OR ^A , -NHR ^A or -N ( ^RA ) ₂ , respectively.
n is an integer of 1 or more independently of each other.
Here, ^RA is a saturated or unsaturated branched or linear hydrocarbon group having 1 to 21 carbon atoms which may be optionally substituted with 1 to 2 carboxyl groups).
The microorganism inhibitor according to any one of claims 1 to 4, which comprises a spicrysporic acid-induced polymer or a salt thereof containing at least one moiety represented by. The microorganism inhibitor according to any one of claims 1 to 7, which contains a metal component. The microbial inhibitor according to any one of claims 1 to 8, which is a detergent, a spray applied to the skin, a disinfectant or antibacterial spray, or a water-related product. The microorganism inhibitor according to any one of claims 1 to 9, which is a polymer material.

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