Device for analyzing sense of taste and method for analyzing sense of taste

Abstract

To provide a device for analyzing a sense of taste which can acquire data with a simple configuration and can easily analyze the taste of food or drink as a target.SOLUTION: The device for analyzing a sense of taste which achieves the above objective includes: a light emission information acquisition unit for emitting light by excitation and acquiring light emission information of a light emission probe of which light emission behavior is changed by a mutual interaction with food or drink; excitation means for exciting the light emission probe; and an analysis unit for analyzing the sense of taste of the food or drink on the basis of the light emission information.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates to a taste analysis device and a taste analysis method. [Background technology]

[0002] Taste is a sensation that is mainly sensed by taste buds on the human tongue, and is generally divided into five tastes: sweet, sour, salty, bitter, and umami. Conventionally, taste has been estimated by detecting specific components in food and drink using various sensors and analyzing their concentrations. In addition, programs and systems have been proposed that measure the content of specific components such as organic acids, amino acids, and sugars, as well as the carbonation level using a carbon dioxide meter, to estimate taste in more detail (e.g., Patent Documents 1 and 2). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2022-47369 A [Patent Document 2] JP 2022-55690 A Summary of the Invention [Problem to be solved by the invention]

[0004] However, in the method described in the above patent document, it is necessary to detect and quantify different components for each of the five tastes and other elements in food and drink. Therefore, many sensors are required, and complex processing and devices are required to separate them. There are also problems such as the time required for these analyses. Furthermore, in this method, components that are not of interest are not used to estimate taste. Therefore, there is also a problem that taste cannot be accurately estimated when new or unknown components that affect taste are included.

[0005] In response to the above-mentioned problems, the present invention aims to provide an analysis method capable of easily acquiring data and accurately analyzing the taste of a target food or drink, and a taste analysis device used therefor. [Means for solving the problem]

[0006] In order to achieve the above-mentioned object, one aspect of the present invention provides a taste analysis device including a luminescence information acquisition unit for acquiring luminescence information of a luminescent probe that emits light upon excitation and whose luminescence behavior changes upon interaction with food or drink, an excitation means for exciting the luminescent probe, and an analysis unit for analyzing the taste of the food or drink based on the luminescence information.

[0007] In order to achieve the above-mentioned object, one aspect of the present invention further provides a method for analyzing taste, comprising the steps of: exciting a luminescent probe that emits light upon excitation and whose luminescence behavior changes upon interaction with food or drink while not interacting with the food or drink, and acquiring single luminescence information; allowing the luminescent probe to interact with the food or drink; exciting the luminescent probe in a state of interaction with the food or drink, and acquiring interaction luminescence information; and analyzing the taste of the food or drink based on the single luminescence information and the interaction luminescence information. Effect of the Invention

[0008] According to one embodiment of the present invention, there is provided a taste analysis method that can easily acquire data and can analyze the taste of food and drink in detail, and a taste analysis device that can be used for this method. [Brief description of the drawings]

[0009] [Figure 1] FIG. 1 is a diagram showing a flow of a taste analysis method according to one embodiment of the present invention. [Diagram 2] FIG. 2 is a diagram showing a flow of a taste analysis method according to a modified example of one embodiment of the present invention. [Diagram 3]FIG. 3 is a plan view of a well plate used in the taste analysis method according to one embodiment of the present invention. [Figure 4] FIG. 4 is a diagram illustrating the structure of a luminescent probe used in one embodiment of the present invention. [Diagram 5] FIG. 5 is a diagram for explaining a method for producing a luminescent probe used in one embodiment of the present invention. [Figure 6] 6A to 6D are diagrams for explaining the mechanism by which the luminescent probe used in one embodiment of the present invention exerts its effect. [Figure 7] 7A to 7D are diagrams illustrating a method for causing an interaction between a luminescent probe and food or drink in another embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] Hereinafter, one embodiment of the present invention will be described in detail. However, the present invention is not limited to this embodiment. In the following, a taste analysis method will be described first, and then a taste analysis device that can be used therefor will be described.

[0011] 1. Taste Analysis Method FIG. 1 shows a flow of the taste analysis method of this embodiment. In this embodiment, a luminescent probe that emits light by excitation and whose luminescence behavior changes by interaction with food or drink is prepared, and single luminescence information is obtained when the luminescent probe is excited (S10, hereinafter also referred to as the "single luminescence information acquisition step"). Next, the luminescent probe and food or drink are allowed to interact (S11, hereinafter also referred to as the "interaction step"). Furthermore, the luminescent probe in an interacting state with the food or drink is excited to acquire interaction luminescence information (S12, hereinafter also referred to as the "interaction luminescence information acquisition step"). After that, the taste of the food or drink is analyzed from the single luminescence information and the interaction luminescence information (S13, hereinafter also referred to as the "analysis step"). However, in cases where the single luminescence information is already known, the single luminescence information acquisition step S11 does not necessarily have to be performed. Furthermore, the interaction luminescence information acquisition step S12 and the single luminescence information acquisition step S10 may be performed simultaneously.

[0012] 2, a step of acquiring chemical information and / or physical information of the food and drink (S14, hereinafter also referred to as a "food and drink information acquiring step") may be performed separately before the analyzing step S13. In this case, in the analyzing step S13, it becomes possible to analyze the taste of the food and drink not only from the single luminescence information acquired in the single luminescence information acquiring step S10 and the interaction luminescence information acquired in the luminescence information acquiring step S12, but also from the chemical information and / or physical information of the food and drink acquired in the food and drink information acquiring step S14, enabling a more detailed analysis.

[0013] In the taste analysis method of this embodiment, the individual components contained in the target food or drink are not identified, but the luminescence state of the luminescent probe, whose luminescence state changes due to interaction with the food or drink, is identified. Therefore, the taste of the food or drink can be analyzed in a simple manner, and the analysis can be performed in a short time. In addition, since the focus is not only on a specific component, the taste of the food or drink can be analyzed comprehensively. Therefore, the taste of the food or drink can be analyzed more accurately. Each step of the analysis method of this embodiment will be described below. In the following description, an example will be described in which 12 types of food or drink are analyzed using a 96-hole well plate 100 shown in FIG. 3. However, the present invention is not limited to this embodiment.

[0014] (Single light emission information acquisition process) In the single luminescence information step S10, a luminescent probe is prepared and excited to obtain luminescence information (single luminescence information) of the luminescent probe in a state where it is not interacting with food or drink. When multiple luminescent probes are used for analyzing food or drink, single luminescence information may be obtained for each luminescent probe individually, but it is preferable to obtain single luminescence information for multiple luminescent probes simultaneously in terms of efficiency, etc. In this embodiment, 16 types of luminescent probes (not shown) are prepared, and different luminescent probes are arranged in each row (r1 row to r8 row) of a 96-well well plate 100 shown in FIG. 3. The same luminescent probe is arranged in each of the same rows. However, this method can be changed arbitrarily. For example, the same luminescent probe may be arranged in all wells. In addition, although a well plate is used in this embodiment, the member (holding member) that holds the luminescent probe and food or drink is not limited to a well plate as long as it can hold them, and may be, for example, a flat plate or the like, or may be an organic EL element, as described later.

[0015] In this embodiment, the method of arranging the luminescent probes at predetermined positions on the well plate 100 is appropriately selected depending on the type of luminescent probe, etc. For example, when a liquid luminescent probe is used, it may be injected using a dispenser or the like. It may also be arranged using an automatic dispenser or by inkjet printing.

[0016] The method of exciting the luminescent probes is appropriately selected depending on the type of luminescent probe, and in this embodiment, the luminescent probes are excited by irradiating them with excitation light. Then, information on the light emitted by each luminescent probe is obtained as single luminescence information. At this time, the luminescent probes placed in the well plate may be excited in sequence to obtain single luminescence information, but generally, it is preferable in terms of analysis efficiency to simultaneously excite all the luminescent probes placed in the well plate to obtain multiple single luminescence information at once.

[0017] In addition, the type of excitation light for exciting the luminescent probe and the type of data acquired as the single luminescence information are appropriately selected according to the analysis method, etc. For example, a specific excitation light (excitation light of a single wavelength) may be irradiated, and the intensity and wavelength (luminescence information) of the light emitted by each luminescent probe may be measured using a spectrophotometer or the like, and this may be used as the single luminescence information. Furthermore, the obtained light may be decomposed into, for example, tristimulus values ​​(for example, XYZ of the CIE color system), and three pieces of data for each of XYZ may be acquired as the single luminescence information. In addition, when a specific excitation light is irradiated, the change over time in the spectral distribution of the light emitted by the luminescent probe and the change in chromaticity over time may be continuously or intermittently measured using a spectrophotometer or the like, and this may be used as the single luminescence information.

[0018] Furthermore, the change in chromaticity of the light emitted by the luminescent probe may be acquired. In this case, excitation light of a single wavelength may be irradiated for a short period of time, and the light emitted by the luminescent probe in response to this may be acquired as an image or video using a CCD camera, CMOS camera, etc. The chromaticity may be identified from the acquired image or video, and data on the change in chromaticity over time may be used as single luminescence information.

[0019] The wavelength of the excitation light is appropriately selected depending on the type of luminescent probe and the type of food or drink to be analyzed, and can be, for example, light with a wavelength of 300 nm or more and 700 nm or less. Such light is unlikely to affect the food or drink. Also, no special light source is required.

[0020] About luminescent probes The luminescent probe used in this embodiment may be any substance that emits light when excited and whose luminescence behavior changes when interacting with food or drink. In this embodiment, the luminescent probe is a compound that is excited by irradiation with excitation light to emit light and whose luminescence behavior changes when interacting with food or drink. In this specification, the luminescent probe's luminescence behavior changes when interacting with food or drink refers to the fact that the atoms, molecular structure, electronic state, etc. in the luminescent probe change chemically or physically when interacting with food or drink, causing a change in the light emitted by the luminescent probe (e.g., spectrum, lifetime, etc.).

[0021] The structure of the luminescent probe is not particularly limited, and the luminescent probe prepared in this embodiment is a compound having one or more luminescent moieties in the molecule that are excited by irradiation with excitation light to emit light. The luminescent probe may have a plurality of the luminescent moieties. When one luminescent probe (molecule) has a plurality of luminescent moieties, the types of the plurality of luminescent moieties may be the same or different.

[0022] The light emitted by the luminescent probe excited by irradiation with excitation light may be light emitted by one luminescent unit alone in the luminescent probe, or may be light emitted by the interaction of multiple luminescent units in the luminescent probe. Examples of light emitted by the luminescent probe include fluorescence, phosphorescence, excimer luminescence, exciplex luminescence, thermally activated delayed fluorescence, excited state intramolecular proton luminescence, triplet triplet annihilation luminescence, twisted intramolecular charge transfer luminescence, and aggregation-induced luminescence. One luminescent probe may emit only one type of light, but if one luminescent probe generates multiple types of light, more complex luminescence information can be obtained.

[0023] The luminescent probe of this embodiment has a nucleic acid structure and one or more luminescent moieties (hereinafter also referred to as "chromophore" or "luminophore") bound to the main chain of the nucleic acid structure. In this specification, the nucleic acid structure includes not only structures derived from DNA or RNA, but also structures derived from one or more compounds selected from the group consisting of phosphorothioate oligodeoxynucleotides, 2'-O-(2-methoxy)ethyl-modified nucleic acids, siRNA, crosslinked nucleic acids, peptide nucleic acids, aTNA, SNA, GNA, LNA, and morpholino antisense nucleic acids. In the following, an example will be described in which the luminescent probe is a compound having a main chain having a pentose or hexose-derived sugar structure and one or more structural units containing a phosphate ester bond bound to the sugar structure, and one or more luminescent moieties (chromophore or luminophore) bound to the sugar structure.

[0024] The main chain of the luminescent probe may have one or more structural units including a sugar structure derived from pentose or hexose and a phosphate bond bonded to the sugar structure. The main chain may contain only one of the structural units, or may contain a plurality of the structural units. That is, the main chain may have a structure including one sugar structure and one phosphate bond bonded to the sugar structure, or may have a structure including sugar structures and phosphate bonds alternately. Usually, both ends of the main chain of the luminescent probe are sugar structures, so that the number of sugar structures is one more than the number of phosphate bonds. When the main chain of the luminescent probe contains a plurality of structural units, the structural units may be the same as or different from each other.

[0025] The number of the structural units contained in the main chain of the luminescent probe is appropriately selected depending on the type of food or drink, and is preferably 2 to 6. The greater the amount of the structural units, the easier it is for the luminescent probe to act specifically on food or drink. However, it is also preferable to obtain a large amount of data by allowing the luminescent probe to interact with various structures of food or drink. Therefore, it is preferable that the luminescent probe and food or drink have appropriate (not excessive) specificity, and the number of the structural units is preferably 6 or less.

[0026] The main chain of the luminescent probe may partially contain a structure other than the structural unit containing the pentose or hexose-derived sugar structure and the phosphate ester bond, within the scope that does not impair the purpose and effect of this embodiment. In addition, the structures at both ends of the main chain are not particularly limited, and can be various structures such as OH groups and alkoxy groups.

[0027] Examples of pentose include ribose, deoxyribose, and xylose. Examples of hexose include allose, glucose, mannose, and the like. Among these, a sugar structure derived from ribose or deoxyribose is particularly preferable because the main chain of the luminescent probe has a structure similar to that of DNA or RNA, and is more likely to interact with DNA or RNA in food and drink.

[0028] When the main chain of the luminescent probe contains a structure derived from ribose or deoxyribose, the phosphate ester bond is preferably bonded to the 3rd carbon and the 5th carbon of the ribose or deoxyribose. In addition, the chromophore or luminophore described below is preferably bonded to the 1st position of the ribose or deoxyribose. In other words, the luminescent probe of this embodiment preferably contains a structure represented by the following general formula (1a) or (1b). [ka] In the general formulae (1a) and (1b), Y represents a chromophore or luminophore as described below.

[0029] On the other hand, the light-emitting portion (chromophore or luminophore) of the luminescent probe may have a structure that emits a specific type of light by itself in response to a single excitation light, or emits a specific light by the action of multiple chromophores or luminophores. It is preferable that the chromophore or luminophore is bound to the sugar structure of the main chain so that the sugar structure is in a β form. In this specification, the term "chromophore" refers to a structure that absorbs light with a wavelength of 300 nm or more, and the term "luminophore" refers to a structure that absorbs light with a wavelength of 300 nm or more and emits light.

[0030] The number of chromophores or luminophores in one luminescent probe may be 1 or 2 or more. However, from the viewpoint that the luminescent probe is likely to exhibit multiple types of luminescence, 2 or more is preferable, and 3 to 6 is more preferable. When the luminescent probe has multiple chromophores or luminophores, these may be the same as each other or different. In the luminescent probe, one chromophore or luminophore is usually bound to one sugar structure in the main chain. Therefore, when the luminescent probe has multiple chromophores or luminophores, it is preferable that the number of sugar structures in the main chain is also multiple. In other words, it is preferable that the number of chromophores or luminophores in the luminescent probe is the same as or less than the number of sugar structures (or peptide structures) in the main chain of the above-mentioned signal generating part.

[0031] Here, when the luminescent probe has a plurality of chromophores or luminophores, the chromophores or luminophores may be evenly arranged in the main chain (sugar structure) of the luminescent probe. On the other hand, as shown in FIG. 4, the chromophores or luminophores may be bound only to a part of the region of the luminescent probe (the 10th sugar structure from the tip in FIG. 4). Such a luminescent probe has a region (hereinafter also referred to as "signal generating part") to which the chromophores or luminophores are bound and which contributes to luminescence, and a region (hereinafter also referred to as "base") to which almost no chromophores or luminophores are bound and which does not contribute to luminescence. In this case, a natural nucleic acid base may be bound to the sugar structure on the base side. In this specification, the natural nucleic acid base refers to adenine, guanine, cytosine, thymine, and uracil. A natural nucleic acid base may be bound to a part of the sugar structure on the signal generating part side. However, on the signal generating part side, the ratio of natural nucleobases to the total number of sugar structures in the signal generating part is preferably 50% or less, more preferably 25% or less.

[0032] Usually, the signal generating part is preferably arranged in the first ten sugar structures from the tip. However, when the food or drink contains a large molecular size such as a protein or liposome, the signal generating part may continue from the tip to the tenth sugar structure and beyond. Here, in the signal generating part, it is preferable that 50% or more of the sugar structures to which the chromophore or luminophore is bound are β-form. Generally, DNA has a structure in which bases are bound to a main chain (deoxyribose) containing a phosphate ester bond and a structure derived from deoxyribose, but in natural DNA, all deoxyribose in the main chain is β-form. Therefore, if 50% or more of the sugar structures in the signal generating part (region to which the chromophore or luminophore is bound) are β-form, it can be said that the structure is highly similar to substances existing in nature, such as DNA and RNA. When such a luminescent probe is mixed with food or drink, it is unlikely to cause steric hindrance, and it can penetrate inside or conform to the shape of the food or drink. Therefore, it is possible to analyze the food or drink in more detail.

[0033] In addition, in the signal generating portion of the luminescent probe, it is more preferable that 80% or more of the sugar structures to which the chromophore or luminophore is bound are β-forms, and it is even more preferable that all of them are β-forms. Whether the sugar structure to which the chromophore or luminophore is bound is β-form or α-form can be confirmed by NMR analysis, X-ray crystal structure analysis, or the like.

[0034] Here, examples of chromophores or luminophores that emit fluorescence include structures derived from fluorescein, rhodamine, boron dipyrromethene, and the like. Examples of chromophores or luminophores that emit phosphorescence include structures derived from iridium complexes, platinum complexes, and the like. Examples of chromophores or luminophores that emit excimer emission include structures derived from pyrene, anthracene, perylene, and the like. Examples of chromophores or luminophores that emit exciplex emission include structures derived from pyrene-dimethylaniline, and the like. Examples of chromophores or luminophores that emit thermally activated delayed fluorescence include structures derived from 4CzIPN, DABNA, and the like. Examples of chromophores or luminophores that emit excited state intramolecular proton emission include structures derived from hydroxyphenylbenzoxazole, and the like. Examples of chromophores or luminophores that emit triplet triplet annihilation emission include structures derived from 9,10-diphenylanthracene, rubrene, and the like. Examples of chromophores or lumophores that emit twisted intramolecular charge transfer luminescence include structures derived from diaminoanthracene, diaminonaphthalene, etc. Examples of chromophores or lumophores that emit aggregate organic luminescence include structures derived from tetraphenylethene, hexaphenylsilole, etc.

[0035] Furthermore, compounds used as light-emitting materials or hosts, electron transport materials, hole transport materials, and light-emitting materials in organic electroluminescence can also be suitably used as the above-mentioned chromophore or luminophore materials. Specific examples of such compounds include those described in "State-of-the-art organic electroluminescence" (CMC Publishing), Organic electroluminescence material technology (CMC Publishing), All about organic electroluminescence (Nihon Jitsugyo Publishing), and Diverse dye materials that open up the future (Kagaku Dojinsha).

[0036] The reasons why various compounds for organic EL are suitable as the chromophore or luminophore of the signal generating part of the luminescent probe are as follows. For example, since the electron transport material is a substance containing an electron-accepting aromatic compound that easily becomes an anion radical, it strongly interacts with electron-rich compounds in food and drink. Conversely, since the hole transport material is a substance containing an electron-donating aromatic compound that easily becomes a cation radical, it strongly interacts with electron-deficient compounds in food and drink. The luminescent material of the organic EL has both properties and is a substance with a high luminescence quantum yield, so a strong luminescence signal can be obtained. In addition, phosphorescent materials and delayed fluorescent materials can also be used. These emit light at a time delayed by about nanoseconds to μseconds compared to conventional fluorescent emission, so that as a sensing material, the factor of time can also be included in the number of dimensions, and as described later, when the analysis is performed using machine learning or deep learning, it is preferable because the data can be multidimensionalized.

[0037] Representative examples of organic electroluminescent materials are given below. These are molecular groups that can be Y in the above general formulas (1a) and (1b). Y may also be formed via a linking group or the like.

[0038] [ka]

[0039] [ka]

[0040] [ka]

[0041] [ka]

[0042] Further, examples of chromophores or luminophores other than those mentioned above include the following: [ka]

[0043] Furthermore, the luminescent probe used in this embodiment may have a structure derived from a non-luminescent monomer. Such a structure derived from a non-luminescent monomer can function as a site that controls the interaction between food and drink and the luminescent probe. Examples of representative functions and monomer structures that realize them are shown below.

[0044] A1) Compounds that capture metal ions Representative examples include those having a ligand structure that forms a chelate, and the coordination types include N,N coordination, N,O coordination, O,O coordination, N,S coordination, O,S coordination, S,S coordination, N,Se coordination, O,Se coordination, S,Se coordination, Se,Se coordination, etc. Specific examples include 2,2'-bipyridine, phenanthroline, 1,8-diaminonaphthalene, amino acids, cryptands, crown ethers, 8-hydroxyquinoline, 3-mercaptopropanol, 3-mercaptopropionic acid, thiocatechol, salicylaldehyde, acetoacetic esters, β-diketones, etc.

[0045] A2) A compound whose molecular shape changes depending on the wavelength of light irradiated to it Representative examples include azobenzenes, stilbenes, fulgides, diarylethenes, spiropyrans, spirooxazines, dihydropyrenes, phenoxyquinones, biindenylidenediones, cobalt complexes, imidazole dimers, and the like.

[0046] A3) Compounds that act as Lewis acids Representative examples include Group 13 elements and transition metals, and specific examples include triarylborane, trialkylborane, trialkoxyborane, trifluoroborane, trichloroborane, and tribromoborane.

[0047] A4) Compounds that act as Lewis bases Representative examples include Group 15 and 16 elements, and specific examples include arylamines, alkylamines, arylphosphines, alkylphosphines, aryl ethers, alkyl ethers, aryl sulfides, and alkyl sulfides.

[0048] A5) Compounds that interact with peptides and proteins Representative examples include nucleic acid bases, transition metal complexes, and oxoacids, and specific examples include adenine, thymine, guanine, thymine, cytosine, zinc complexes, copper complexes, nickel complexes, cobalt complexes, tungstic acid, molybdic acid, and phosphoric acid.

[0049] A6) Compounds that form hydrophobic-hydrophobic interactions Representative examples include straight chain alkanes, straight chain alkenes, straight chain alkynes, branched alkanes, branched alkenes, branched alkynes, aromatic rings, heteroaromatic rings, and the like.

[0050] A7) Compounds that form dipole-dipole or quadrupole-quadrupole interactions Representative examples include alkyl halides, aryl halides, nitriles, nitroarenes, anilines, anisoles, heterocycles, and the like.

[0051] In this embodiment, the luminescent probe preferably contains at least one structure selected from a structure that emits fluorescence, a structure that emits excimer emission, and a structure that emits exciplex emission as a chromophore or luminophore, and preferably contains at least a structure that emits fluorescence. When the luminescent probe emits fluorescence, it has the advantage of being easy to detect and analyze.

[0052] Furthermore, the luminescent probe preferably exhibits multiple types of luminescence when irradiated with light having a wavelength of 300 to 400 nm. If the luminescent probe exhibits multiple types of luminescence when irradiated with light having the wavelength, no special light source is required when analyzing food and drink, and damage to the food and drink is unlikely to be caused.

[0053] However, when an LED or an organic EL element is used as the excitation light source, excitation in the visible light range is advantageous. In such a case, the absorption wavelength of the above-mentioned luminescent probe is effective at 400 to 700 nm, and such a dye can also be used.

[0054] The molecular weight of the luminescent probe (the molecular weight of the signal generating part when it has a signal generating part and a base part) is appropriately selected depending on the type of chromophore or luminophore possessed by the luminescent probe, the length of the main chain, etc., and is usually preferably from 500 to 10,000, more preferably from 500 to 4,000. When the molecular weight of the luminescent probe is 10,000 or less, the specificity for food and drink is appropriately low, making it possible to react nonspecifically with multiple sites in food and drink.

[0055] In the above description, the structural unit constituting the main chain of the nucleic acid structure of the signal generating part has a structural unit containing a sugar structure derived from pentose or hexose such as DNA or RNA and a phosphate ester bond, but as mentioned above, it is not limited to these. Representative examples of other structural units include peptide nucleic acid type structural units such as those shown below. [ka]

[0056] Like DNA / RNA, peptide nucleic acids can be comprehensively synthesized using a commercially available automatic synthesizer (peptide synthesizer). Since peptide nucleic acids have no charge and no electrostatic repulsion, they can form stronger associations with food and drink. In addition, they are resistant to enzymes such as nucleases and proteases. Furthermore, they can be synthesized on a relatively large scale. However, because of their non-ionic structure, they may aggregate in water and lose their solubility. Therefore, when the signal generating part has a structure derived from peptide nucleic acid, it is preferable to appropriately select the type of base to be linked to the signal generating part and to select the solvent.

[0057] Here, the method for producing the luminescent probe is appropriately selected according to the structure of the luminescent probe. For example, the luminescent probe having the above-mentioned sugar structure can be produced by the following method. A monomer is prepared by binding the above-mentioned chromophore or luminophore and a phosphate ester to a pentose or hexose. The monomer can be synthesized by polymerizing the monomer in a desired sequence using a phosphoramidite method with a DNA / RNA synthesizer or the like. According to this method, for example, as shown in the schematic diagram of FIG. 5, multiple types of monomers (three types in FIG. 5) with different types of chromophore or luminophore (represented by A, B, and C in FIG. 5) can be prepared, and the monomers can be bonded in a desired number by changing the sequence order (three are bonded in FIG. 5). In other words, a wide variety of luminescent probes can be synthesized from multiple types of monomers with different types of chromophore or luminophore. In the example shown in FIG. 5, 27 types of luminescent probes can be synthesized. By changing the type of monomer used and the number of monomers bonded, a very large number of luminescent probes can be synthesized.

[0058] In addition, when the phosphoramidite method is performed, a part of the monomer, for example, a hydroxyl group of a sugar structure (for example, a hydroxyl group bonded to the carbon at the 3rd position of ribose or deoxyribose) or a hydroxyl group derived from phosphoric acid is usually supported on a particulate carrier (also referred to as "carrier particles" in this specification) and a polymerization reaction is carried out. The carrier particles are, for example, porous glass, porous silica gel, or polystyrene, and porous glass includes porous bodies of metal oxides such as silica gel and alumina. After synthesis of the luminescent probe (polymerization of the monomer), the carrier may be removed to obtain only the luminescent probe, or the luminescent probe may be used in a state where it is supported on the carrier particles. Furthermore, the luminescent probe may be mixed with a liquid and used as an ink.

[0059] The luminescent probe has a main chain structure similar to that of substances present in nature (e.g., DNA and RNA). Therefore, it can easily interact with various foods and drinks, and the luminescent probe can be used to grasp the state of the foods and drinks in detail. In addition, the luminescent probe emits light when irradiated with light of a specific wavelength. Therefore, it is possible to obtain various luminescence data depending on the state of the foods and drinks, and it is possible to analyze the foods and drinks in great detail.

[0060] The mechanism by which this effect manifests is shown diagrammatically in Figures 6A to 6D. First, for the purpose of facilitating understanding, the luminescent probe is a molecule having four sugar structures and four luminophores as shown in Figure 6A. All four R's may be pyrene (Py in Figure 6), dimethylaminobiphenyl (N in Figure 6), or a mixture of both. Furthermore, one or two of the four R's may be hydrogen atoms. With such a molecular structure, a composite luminescent probe can be constructed.

[0061] In this embodiment, the luminescent probe causes a complex interaction with food and drink, generating a large amount of multidimensional data as light and color signals. Figures 6B to 6D show this concept in the simplest and most specific way, and there are three main aims.

[0062] For example, assuming that all of the R's above are pyrene, when food or drink is brought into contact with the liquid or medium in which this luminescent probe is present and excited with ultraviolet light, if there is a component contained in the food or drink that is inserted between the pyrenes present in the luminescent probe and has a wide band gap that does not quench the fluorescence of pyrene (e.g., an aliphatic compound), monomeric pyrene emission as shown in the left diagram in Figure 6B will be observed from the luminescent probe.

[0063] If the food or drink does not contain any components that interact with pyrene, excimer emission from pyrene is observed, as shown in the center of Figure 6 B. If the sample contains a component (fluorescent substance) that interacts with pyrene and has an energy level close to the band gap of pyrene, exciplex emission from pyrene and the component (fluorescent substance) is observed, as shown in the right diagram of Figure 6 B.

[0064] Furthermore, when metal ions such as sodium ions or calcium ions are present in food or drink, a chelate is formed between the phosphate group in the main chain of the luminescent probe. However, as shown in Figure 6D, the intermolecular distance between pyrene molecules changes depending on the size of the metal ion, and therefore the emission color (emission spectrum) of the excimer emission itself also changes.

[0065] In addition, when R in the structure shown in Figure 6A is dimethylaminobiphenyl (N), the emission color (spectrum) of the fluorescent dye (N) changes due to the proximity of the acid and base as shown in Figure 6C. This is different from the on / off switching of acid-base ion pairs such as mineral acids (such as sulfuric acid and nitric acid) and alkali metals. In this case, the approach distance with N changes continuously depending on the acidity (ease of donating protons) of the substance contained in the sample. Therefore, using this emission phenomenon as a signal leads to an expansion of the dynamic range. In addition, since N is a Lewis base, it interacts similarly with Lewis acidic substances (such as triarylborane, trialkylaluminum, and tetraalkoxytitanium) in addition to protic acidic substances. Therefore, when such ingredients are contained in food or drink, a specific emission color change occurs.

[0066] Next, when every other R in the luminescent probe is pyrene (Py) and dimethylaminobiphenyl (N), exciplex luminescence between pyrene and dimethylaminobiphenyl is observed if there is no interaction between the sample and pyrene or dimethylaminobiphenyl, unlike the above. On the other hand, if there is interaction, complex luminescence due to mixed exciplexes between the sample components and pyrene and / or dimethylaminobiphenyl is obtained as above.

[0067] Furthermore, when one or two of the inner R's are hydrogen atoms, excimer or exciplex emission does not occur from the luminescent probe itself, or the contribution of such emission is small, and monomer emission is observed almost entirely. However, because the steric hindrance of the hydrogen atoms is small, the interaction between the food or drink and the R of the luminophore is enhanced, resulting in an enhanced change in the luminescence signal.

[0068] In the case where Py and N in Fig. 6A are not normal fluorescent substances but phosphorescent compounds or thermally excited delayed fluorescent compounds, light is emitted several tens of nanoseconds to several microseconds after excitation. Therefore, the dynamic range is expanded by the factor of "time" rather than the color of the emitted light, and such a phenomenon can be applied to this embodiment in addition to the mechanisms shown in Figs. 6B to 6D.

[0069] Until now, such intermolecular interactions and the resulting subtle changes in luminescence color and spectrum, or the delay in luminescence of several microseconds, as well as the extremely subtle changes in luminescence phenomena brought about by metal chelate formation due to the main chain structure, have not been applicable as analytical information for humans to understand. However, assuming the use of artificial intelligence (AI), which has become widely available in recent years, and machine learning and informatics that utilize it, such diverse luminescence phenomena that are beyond human understanding can become state description data corresponding to the target food and drink.

[0070] (interaction process) In the interaction step S11, the target food and drink are allowed to interact with the luminescent probe from which the above-mentioned single luminescence information was obtained. In this embodiment, 12 types of food and drink are arranged in each row (row c1 to row c12) of the above-mentioned 96-well plate 100. In this embodiment, the same food and drink are arranged in the same row, but the arrangement method is not limited to this.

[0071] The method of interaction between the food or drink and the luminescent probe is not particularly limited, and may be, for example, simply mixed in a well plate, or may be heated or a chemical for promoting the interaction may be added as necessary. Furthermore, the interaction may be promoted by leaving the mixture to stand for a predetermined period of time.

[0072] Food and drink The food and drink to which the method of the present embodiment can be applied may be any food and drink that can interact with the luminescent probe, and may be a beverage, a vegetable, meat, fish, or other raw material itself, or raw materials before processing or cooking. The food and drink may be in the process of processing or cooking, or may be processed or cooked. Furthermore, the food and drink may be stored for a certain period of time. The food and drink may be in a liquid state, a solid state, a paste state, or the like. However, the liquid state is more likely to interact with the luminescent probe. In addition, when a food and drink contains multiple ingredients, the multiple ingredients are more likely to mix uniformly in a liquid state, making it easier to analyze the overall taste. Therefore, the solid ingredients may be finely chopped or crushed, and liquid ingredients may be extracted from these to interact with the luminescent probe.

[0073] (Interaction luminescence information acquisition step) In the interaction luminescence information acquisition step S12, the luminescent probe is excited (irradiated with excitation light in this embodiment) while the food or drink and the luminescent probe are interacting with each other, and interaction luminescence information emitted by the luminescent probe is acquired. In this step, the interaction luminescence information of the luminescent probe interacting with the food or drink placed in each well described above may be acquired individually, but it is more preferable to acquire the interaction luminescence information of the luminescent probes in all well plates at once in terms of analysis efficiency, etc.

[0074] The type of interaction luminescence information to be acquired is not particularly limited, and it is usually preferable to acquire the same type of information as the above-mentioned single luminescence information. For example, a specific excitation light (single wavelength excitation light) may be irradiated, and the intensity and wavelength (luminescence information) of the light emitted by each luminescent probe may be detected by a spectrophotometer or the like. Furthermore, the obtained light may be decomposed into, for example, tristimulus values ​​(for example, XYZ of the CIE color system), and three pieces of data for each of XYZ may be acquired as interaction luminescence information. In addition, when a specific excitation light is irradiated, the change over time in the spectral distribution of the light emitted by the luminescent probe or the change in chromaticity over time may be detected continuously or intermittently by a spectrophotometer or the like.

[0075] Furthermore, the chromaticity change of the light emitted by the luminescent probe may be acquired. In this case, excitation light of a single wavelength may be irradiated for a short period of time, and the light emitted by the luminescent probe in response to this may be acquired as an image or video using a CCD camera, CMOS camera, etc. The chromaticity may be identified from the acquired image or video, and data on the chromaticity change over time may be used as the interaction luminescence information.

[0076] It is preferable to obtain the interaction luminescence information when the interaction between the food or drink and the luminescent probe has progressed sufficiently. Therefore, for example, when obtaining the above-mentioned tristimulus value XYZ as the interaction luminescence information, it is preferable to obtain the interaction luminescence information by the following method. First, the tristimulus value XYZ of the light emitted by the luminescent probe is obtained multiple times. Note that multiple times means that the tristimulus value XYZ is obtained at different times. Then, from the tristimulus value XYZ obtained multiple times, the time-dependent change of each of the tristimulus values ​​XYZ is specified. From the specified time-dependent change, a range in which the value fluctuation rate for 10 minutes is ±10% or less is specified for each stimulus value. The fluctuation rate is the rate obtained by dividing the difference between (stimulus value a at a specific time point t) and (stimulus value b 10 minutes before the specific time point t) by (stimulus value a 10 minutes before the specific time point t), that is, the value calculated by {(ab) / a}×100. Usually, the fluctuation rate of each stimulus value decreases as the interaction between the food or drink and the luminescent probe progresses. It is preferable to obtain the tristimulus values ​​XYZ obtained after the fluctuation rate of at least one of the stimulus values ​​for 10 minutes becomes ±10% or less as the interaction luminescence information. Note that which data is to be the interaction luminescence information may be determined in the analysis process described later.

[0077] (Food and drink information acquisition process) As described above, in this embodiment, a food and drink information acquisition step S14 may be further performed to acquire chemical information and / or physical information of the food and drink. Examples of chemical information acquired in the food and drink information acquisition step include information on the structure and concentration of specific components in the food and drink (e.g., substances that affect the taste or aroma). Examples of physical information include the color, viscosity, hardness, etc. of the food and drink. In this step S14, one or more types of information may be acquired from the food and drink.

[0078] There are no particular limitations on the method of acquiring chemical information or physical information from food or drink, and it can be performed using a known sensor or the like according to the desired information. Examples of known sensors include various devices for component analysis, various devices for color analysis, and taste sensors. Ingredient analysis can identify the contents of, for example, protein, lipid, carbohydrate, fatty acid, ketone free fatty acid, milk fat, etc. In color analysis, a spectrophotometer (such as the spectrophotometric measuring device CM-700d manufactured by Konica Minolta) can compile data on the color of food or drink. Furthermore, a taste sensor (such as the taste sensor TS5000Z manufactured by Insent and the ASTREE manufactured by Alpha MOS) can acquire data on the five tastes.

[0079] (Analysis process) In the analysis step S13 in this process, the single luminescence information acquired in the single luminescence information acquisition step S10 and the interaction luminescence information acquired in the interaction luminescence information acquisition step S12 may be used as analytical data to analyze the taste of the food or drink. On the other hand, when the food or drink information acquisition step S14 is performed, the taste of the food or drink may be analyzed in more detail using the chemical information and / or physical information acquired in the step. The type of information derived by the analysis is not particularly limited, and may be, for example, information on each of the five tastes of the food or drink, or a sensory evaluation that combines these. Also, elements other than the five tastes, such as flavor intensity, smell, aftertaste, and texture, may be included.

[0080] When carrying out this analysis, the standard data and the analytical data may be simply compared, or, for example, the result of the comparison between the standard data and the analytical data may be converted into a distance matrix and analyzed using a heat map (unweighted), or the distance matrix may be subjected to principal component analysis (also known as PCA, weighting that emphasizes anisotropy) or analysis using DL (weighting that emphasizes isotropy).

[0081] On the other hand, the analysis data may be analyzed using a trained model constructed in advance. The trained model may be created, for example, by a machine learning process described later, but the trained model used is not limited to the one created by the machine learning process described later. Using the trained model allows for more appropriate analysis of the taste of food and drink.

[0082] When referring to a trained model, the above-mentioned analysis data can be applied to the trained model to determine (predict) the taste of the food or drink from accumulated data, etc. The prediction result may be obtained as, for example, classification, regression, clustering, anomaly detection (outlier detection), etc.

[0083] (Machine learning process) The analysis method of this embodiment may further include a learning step of performing machine learning on the analysis data to generate a learned model.

[0084] For example, in the machine learning process, a plurality of predictive models may be constructed based on the above-mentioned analysis data, and the results of the plurality of predictive models may be combined to create a trained model capable of predicting various information related to the taste of food and beverages.

[0085] When the taste of a food or drink (e.g., the five tastes or sensory evaluation) is known in advance, the above prediction model can be constructed by performing machine learning with the characteristics of the analysis data as explanatory variables and the taste as the objective variable. As explanatory variables, numerical values ​​representing the characteristics of the above analysis data and numerical values ​​calculated from them can be used. When the above-mentioned single emission information or interaction emission information is a spectroscopic spectrum, the light intensity for each wavelength can be used as an explanatory variable. Furthermore, when chemical information and / or physical information of the above-mentioned food or drink is obtained, this information can be used as explanatory variables.

[0086] On the other hand, the objective variable can be appropriately selected depending on the purpose of the analysis, and is not limited to one element of the taste of food and drink, but may be multiple elements.

[0087] The machine learning performed in this process may be supervised learning or unsupervised learning. Note that supervised learning refers to a learning method for learning the "relationship between input and output" from training data with a correct answer label. Unsupervised learning refers to a learning method for learning the "structure of a data group" from training data without a correct answer label.

[0088] Machine learning may be reinforcement learning, deep learning, or deep reinforcement learning. Reinforcement learning is a learning method that learns an "optimal action sequence" through trial and error. Deep learning is a learning method that learns features contained in data in a stepwise and deeper manner (at a deep level) from a large amount of data. Deep reinforcement learning is a learning method that combines reinforcement learning and deep learning.

[0089] General analysis methods (algorithms) can be applied to machine learning. For example, a predictive model constructed by an analysis method selected from linear regression (multiple regression analysis, partial least squares (PLS) regression, LASSO regression, Ridge regression, principal component regression (PCR), etc.), random forest, decision tree, support vector machine (SVM), support vector regression (SVR), neural network, discriminant analysis, etc. can be applied to machine learning.

[0090] ·others In the above, it has been described that the single luminescence information acquisition step S10 and the interaction luminescence information acquisition step S13 are performed at different times. However, in the interaction step S12, food and drink may not be added to one row (e.g., row c1) of the well plate 100 shown in Fig. 3, and food and drink may be added to the remaining rows (e.g., rows c2 to c12). When the luminescent probes and food and drink are arranged in this manner and each luminescent probe is excited, the luminescence information acquired in row c1 becomes single luminescence information, and the luminescence information acquired in rows c2 to c12 becomes interaction luminescence information.

[0091] Other embodiments In the above description, the well plate shown in FIG. 3 is used to obtain the single emission information and the interaction emission information. However, the single emission information and the interaction emission information may be obtained by applying an organic EL element or the like. The embodiment will be described using the process diagrams (schematic cross-sectional views) of FIG. 7A to FIG. 7D. In the embodiment, a laminate is prepared in which a transparent substrate 111, a transparent electrode 112 (e.g., an ITO film, etc.), a hole transport layer 113 (e.g., a polyaromatic diamine, etc.), and a receptor layer / host layer 114 such as polystyrene are formed (FIG. 7A). The transparent substrate 111, the transparent electrode 112, the hole transport layer 113, etc. are the same as those of a known organic EL element. On the other hand, the receptor layer / host layer 114 may be any layer as long as it is capable of receiving the above-mentioned food, drink, or luminescent probe.

[0092] Then, food or drink 121 is applied to a desired area of ​​the receptor layer 114 of such a laminate by any method (FIG. 7B). Next, the above-mentioned luminescent probe is applied in a pattern by an inkjet method or the like to a desired position of the receptor layer 114 to which the food or drink 121 has been applied (FIG. 7C). As a result, the area to which the luminescent probe is applied becomes the luminescent layer 122. In the luminescent layer 122, the luminescent probe and the food or drink interact with each other. Although not shown, in this embodiment, it is also possible to obtain single luminescence information by applying the luminescent probe to an area to which the food or drink is not applied. Then, a counter electrode layer 115 that pairs with the transparent electrode 112 is disposed on the luminescent layer 122 to form an organic EL element. The luminescent probe in the luminescent layer 122 of the organic EL element is excited by a conventional method to obtain interaction luminescence information (step S13 described above), which is then analyzed in the analysis step S14.

[0093] In the above, it has been described that food and drink are applied first to the receiving layer 114, but the light-emitting probe may be applied first, and then the food and drink may be applied. In addition, the configuration of the organic EL element is not limited to the above configuration, and can be modified as desired.

[0094] 2.Analysis equipment The above-mentioned taste analysis method only needs to have an excitation means for exciting the luminescent probe (e.g., an excitation light source or a power supply means in the case of an organic EL element), a luminescence information acquisition unit for acquiring luminescence information of the luminescent probe (single luminescence information or interaction luminescence information), and an analysis unit for analyzing the taste of food and drink based on the luminescence information.

[0095] The excitation means may be any means capable of exciting the luminescent probe. Examples of the excitation light source include a supercontinuum light source (a broadband pulse light source that utilizes the nonlinear effect of optical fibers to emit strong light with a uniform phase over a very wide wavelength range, also known as an "SC light source") and an LED. These excitation light sources can increase the amount of light, making it easier to clarify the luminescence information.

[0096] On the other hand, the luminescence information acquisition unit is configured to acquire luminescence information emitted by the excited luminescent probe, and the type thereof is appropriately selected according to the luminescence information to be acquired. For example, the luminescence information acquisition unit may be a spectrophotometer or an ultraviolet-visible light absorptiometer, or may be a fluorescent fingerprint measuring device. It may also be a circular dichroism spectrometer or a high performance liquid chromatograph (HPLC), or may be a CCD camera or a CMOS camera. The luminescence information acquisition unit may also be a combination of two or more of these.

[0097] In addition, the analysis unit that analyzes the acquired luminescence information (single luminescence information and interaction luminescence information) and, if necessary, chemical information and physical information of food and drink, can be a general information processing device, for example, a personal computer. As such an analysis unit, a general computer (general-purpose computer) equipped with a storage means such as a hard disk drive (HDD), a solid-state drive (SSD), or a read-only memory (ROM) for storing programs, data, trained models, etc., and a central processing unit (CPU) for executing programs and performing calculation processing, etc., can be used. In addition, the computer may further have input means such as a keyboard and a mouse, and output means such as a monitor and a printer.

[0098] The analytical device may have the above-mentioned well plate or an organic EL element (e.g., a laminate including a transparent substrate, a transparent electrode, an electron transport layer, a receptor layer, etc.) as a holding member for holding the luminescent probe or food or drink inside.

[0099] Furthermore, the device may further include a sensor for acquiring chemical information and / or physical information of the food or drink. The type of sensor is not particularly limited and is appropriately selected based on the desired information. For example, the sensor may be a known taste sensor. Furthermore, the sensor may be any of known chromatography devices, viscosity measuring devices, colorimeters, etc.

[0100] The analysis device may further include an inkjet printing unit for placing the above-mentioned luminescent plate and food and drink at desired positions. EXAMPLES

[0101] 1. Sensory evaluation test Thirteen types of commercially available milk were prepared. Then, the milk was subjected to a sensory test by 30 evaluators. Specifically, the richness, sweetness, aroma, aftertaste, and likability of one milk were set as the standard value (rating 0). Then, the remaining 12 types of milk (A to L) were evaluated for richness, sweetness, aroma, aftertaste, and likability using the multiple comparison method to determine whether there was a significant difference in each evaluation item, and were rated on a 7-point scale from -3 to 3 relative to the standard value. The results are shown in Table 1.

[0102] [Table 1]

[0103] 2. Synthesis of Luminescent Probes Luminescent probes 1-16 were synthesized as follows. All reactions were carried out in oven-dried glassware under nitrogen atmosphere unless otherwise noted. All chemical products were purchased from Aldrich, TCI, or Kanto Chemical and used as is without further purification.

[0104] (1) Synthesis of Monomer 1 Based on the following reaction formula, intermediates 1 to 6 were used to synthesize monomer 1 having a main chain containing a phosphate ester and a luminophore bonded to the main chain. [ka]

[0105] Synthesis of intermediate 1 Thymidine (15.0 g, 61.9 mmol) and imidazole (16.9 g, 248 mmol) were dissolved in DMF (124 mL), tert-butyldimethylsilyl chloride (19.6 g, 130 mmol) was added, and the mixture was stirred at room temperature for 17 hours. Water was added to the reaction solution, and the mixture was separated and extracted with ethyl acetate. The resulting organic phase was dried over magnesium sulfate, and the solvent was distilled off to obtain the desired intermediate 1 as a colorless solid (28.3 g, 97%).

[0106] Synthesis of intermediate 2 Intermediate 1 (28.3 g, 60.1 mmol) and ammonium sulfate (12.7 g, 96.2 mmol) were dissolved in hexamethyldisilazane (314 mL, 1.50 mol), and the mixture was heated under reflux for 3 hours. Water was then added to the reaction mixture, and the mixture was separated and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, and the solvent was distilled off to obtain a crude product. The crude product was purified by silica gel column chromatography to obtain the desired intermediate 2 as a brown liquid (13.2 g, 64%).

[0107] Synthesis of intermediate 4 A mixture of intermediate 2 (10.1 g, 29.3 mmol), 1-bromopyrene (8.24 g, 29.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (671 mg, 733 μmol), tritert-butylphosphonium tetrafluoroborate (850 mg, 2.93 mmol), dicyclohexylmethylamine (9.35 mL, 44.0 mmol), and 1,4-dioxane (100 mL) was heated at 90 ° C for 1 hour. The reaction was stopped by adding water, and the mixture was separated and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, and the solvent was distilled off to obtain a crude product containing intermediate 3, which was used as it was in the next reaction.

[0108] To the crude product containing intermediate 3, 100 mL of THF, 1 M tetrabutylammonium fluoride THF solution (117 mL, 117 mmol), and acetic acid (6.74 mL, 117 mmol) were added and stirred at 40°C for 2 hours. Water was added to stop the reaction, and separation and extraction were performed with ethyl acetate. The obtained organic phase was dried over magnesium sulfate, and the solvent was distilled off to obtain a crude product, which was purified by silica gel column chromatography to obtain the desired intermediate 4 as a light brown solid (5.87 g, 63%).

[0109] Synthesis of intermediate 5 A solution of sodium triacetylborate (11.8 g, 55.8 mmol) and acetic acid (7.87 mL, 138 mmol) dissolved in acetonitrile (93 mL) was cooled to 0°C, and a solution of intermediate 4 (5.87 g, 18.6 mmol) dissolved in THF (62 mL) was added dropwise. After the dropwise addition, the temperature was raised to room temperature and the mixture was stirred for 15 minutes, after which water was added to stop the reaction. The organic phase obtained by liquid separation and extraction with ethyl acetate was dried over magnesium sulfate, and the solvent was distilled off to obtain a crude product. The product was purified by silica gel column chromatography and reverse phase HPLC to obtain the desired intermediate 5 as a colorless solid (3.44 g, 58%).

[0110] Synthesis of intermediate 6 A mixture of intermediate 5 (3.44 g, 10.8 mmol), 4,4'-dimethoxytrityl chloride (4.40 g, 13.0 mmol), ethyldiisopropylamine (2.82 mL, 16.2 mmol), and dehydrated pyridine (54 mL) was stirred at room temperature for 4 hours, and then methanol was added to stop the reaction. The solvent was distilled off, and the resulting crude product was purified by silica gel column chromatography to obtain the desired intermediate 6 as a colorless viscous solid (5.71 g, 85%).

[0111] Synthesis of Monomer 1 2-Cyanoethyldiisopropylchlorophosphoramidite (3.08mL, 13.8mmol) was added dropwise to a mixture of intermediate 6 (5.71g, 9.20mmol), ethyldiisopropylamine (6.42mL, 36.8mmol), and dehydrated dichloromethane (92mL) at 0°C. The mixture was warmed to room temperature and stirred for 3 hours, after which the solvent was distilled off to obtain a crude product. The product was purified by silica gel column chromatography to obtain the desired monomer 1 as a colorless solid (4.64g, 61%).

[0112] (2) Preparation of Monomer 2 Monomer 2 was purchased from Glen Research (Sterling, Virginia) as a reagent having the structure shown below. [ka]

[0113] (3) Synthesis of luminescent probes 1 to 16 According to a conventional method, 16 kinds of mixed sequence oligonucleotides (Seq1-16) of monomer 1 and monomer 2 were synthesized as shown in Table 2 below. DNA synthesis reagents were purchased from Glen Research (Sterling, Virginia). All oligonucleotides were synthesized using a standard protocol for phosphoramidite-based coupling method using a DNA / RNA synthesizer NTS T-series manufactured by Nippon Techno Service Co., Ltd. Each luminescent probe carrier obtained by automatic synthesis was reacted with ammonium water at room temperature for 2 hours to be cut out from the particulate carrier, and the solvent was dried with a centrifugal dryer, and then ultrapure water was added to obtain first components 1-16 containing each luminescent probe 1-16. It was confirmed that the luminescent probes 1-15 emit fluorescence and excimer emission by specific excitation light (light with a wavelength of 350 nm). The luminescent probe 16 did not exhibit fluorescence or excimer emission.

[0114] [Table 2]

[0115] 3. Taste analysis 3-1.Example Analysis of the taste of milk was performed by the following method. The analysis device used included a luminescence information acquisition unit for acquiring luminescence information from the luminescent probe, an excitation means for exciting the luminescent probe, and an analysis unit luminescence information acquisition unit for analyzing the taste of the food or drink based on the luminescence information. The luminescence information acquisition unit and the excitation means used were a microplate reader Spark manufactured by Tecan. The analysis unit used an information processing device (computer) connected to the luminescence information acquisition unit and the excitation means.

[0116] (1) Single emission information acquisition process Two wells with 96 holes (12 columns x 8 rows) were prepared. Then, luminescent probe 1 was injected into the first row (12 columns) of the first well. Next, luminescent probe 2 was injected into the second row, and similarly, luminescent probes 3 to 8 were injected into the third to eighth rows, one row at a time. Similarly, luminescent probes 9 to 16 were injected into the second well, one row at a time. Then, in this state, the luminescent probes injected into each well were excited using the luminescence information acquisition unit (microplate reader Spark, manufactured by Tecan Corporation), and their spectra (single luminescence information) were obtained.

[0117] (2) Interaction process Milks A to L, which had been subjected to the above-mentioned sensory evaluation, were dropped into each of the two rows of wells from which the above-mentioned single luminescence information was obtained. Specifically, milk A was dropped into the first row of two wells (8 wells x 2). Milk B was then dropped into the second row (8 wells x 2), and milks C to L were dropped into the third row to the twelfth row, respectively.

[0118] (3) Interaction luminescence information acquisition step After the milk was dropped into the well, a spectrum (interaction luminescence information) was obtained by the luminescence information acquisition unit in the same manner as in the single luminescence information acquisition step. At this time, the spectrum was measured multiple times at different times.

[0119] (4) Machine learning process and analysis process The spectra acquired in the above-mentioned single information acquisition step and interaction luminescence information step were converted into tristimulus values ​​XYZ of the CIE color system. For the tristimulus values ​​of the multiple spectra acquired in the interaction luminescence information step, the time-dependent changes of each tristimulus value were identified. Then, the data (tristimulus values) after the fluctuation rate of at least one stimulus value for 10 minutes became within ±10% were adopted as the interaction luminescence information.

[0120] Then, machine learning was performed using the data of milks A to I. Specifically, the data obtained for milks A to I (3 × 16 pieces = tristimulus values ​​(X, Y, Z) × 16 types of luminescent probes) were used as explanatory variables, and the results of the sensory evaluation performed earlier were used as objective variables to create a prediction formula using PLS regression.

[0121] Next, the remaining milks J to L were predicted for richness, sweetness, aroma, and aftertaste using the prediction formula created, and compared with the results of the sensory evaluation. The results are shown in Table 3. The evaluation was performed according to the following criteria. A: Correlation coefficient with sensory evaluation is 0.9 or more B: Correlation coefficient with sensory evaluation is 0.7 or more and less than 0.9 C: Correlation coefficient with sensory evaluation is less than 0.7

[0122] Furthermore, based on the above results, the overall prediction accuracy was judged based on the following criteria. ◎: 3 or more A's in the above evaluations ○: 1 to 2 A's in the above evaluation △: A in the above evaluation is 0

[0123] 3-2.Comparative Example Using the following taste sensors, we measured multiple types of data that each device could identify for milk A to L. Device A: insent taste sensor TS5000Z Device B: Alpha MOS ASTREE Then, for milks A to I, the values ​​measured by devices A and B were used as explanatory variables, and the results of the sensory evaluation were used as objective variables to create prediction equations for each device using PLS regression. Next, the remaining milks J to L were used to predict their strength, sweetness, aroma, and aftertaste. Then, as in the examples, the results were compared with the sensory evaluation results. The results are shown in Table 3.

[0124] 3-3.Results [Table 3]

[0125] As shown in Table 3 above, the method of the embodiment showed very good prediction accuracy, with a correlation coefficient of 0.9 for strength, sweetness, and preference. On the other hand, the comparative example using the device A and the device B showed low prediction accuracy, with a correlation coefficient of 0.7 or less for all items. [Industrial Applicability]

[0126] According to the present invention, there is provided a taste analysis method that can easily obtain data and can analyze the taste of food and drink in detail, and a taste analysis device that can be used for the same. The taste analysis method and taste analysis device are very useful in fields such as food manufacturing, processing, and quality control. [Explanation of symbols]

[0127] 100 well plate 111 Transparent substrate 112 Transparent electrode 113 Hole transport layer 114 Receptor 115 Counter electrode layer 122 Light-emitting layer

Claims

1. a luminescence information acquisition unit for acquiring luminescence information of a luminescent probe that emits light upon excitation and whose luminescence behavior changes upon interaction with food and drink; an excitation means for exciting the luminescent probe; an analysis unit that analyzes the taste of the food or drink based on the light emission information; A taste analysis device comprising:

2. The apparatus further includes a holding member for holding the light-emitting probe and the food or drink therein. The taste analysis device according to claim 1 .

3. The luminescent probe is a compound containing a nucleic acid structure. The taste analysis device according to claim 1 .

4. Further comprising a sensor for acquiring chemical and / or physical information of the food or drink; The analysis unit analyzes the taste of the food or drink based on the luminescence information and the chemical information and / or physical information. The taste analysis device according to claim 1 .

5. The analysis unit analyzes the taste of the food and drink using a pre-constructed trained model. The taste analysis device according to claim 1 .

6. a step of exciting a luminescent probe that emits light upon excitation and whose luminescence behavior changes upon interaction with food or drink, in a state where the luminescent probe is not interacting with the food or drink, and acquiring independent luminescence information; Allowing the luminescent probe and the food or drink to interact with each other; A step of exciting the luminescent probe that is in an interacting state with the food or drink and acquiring interaction luminescence information; analyzing the taste of the food or drink based on the single luminescence information and the interaction luminescence information; Including, How to analyze taste.

7. In the step of acquiring the interaction luminescence information, tristimulus values ​​of the excitation light of the luminescent probe in an interaction state with the food or drink are acquired multiple times, and the tristimulus value at a predetermined timing after a fluctuation rate of at least one of the tristimulus values ​​over 10 minutes becomes ±10% or less is acquired as the interaction luminescence information. The method for analyzing taste according to claim 6.

8. The method further comprises obtaining chemical and / or physical information of the food or beverage; In the step of analyzing the taste of the food or drink, the analysis is performed based on the single luminescence information, the interaction luminescence information, and the chemical information and / or physical information. The method for analyzing taste according to claim 6.

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