Method for calculating and analyzing influence of ferulic acid on release of sulfur-containing aroma substances

Abstract

The invention provides a method for calculating and analyzing the influence of ferulic acid on release of sulfur-containing aroma substances, and belongs to the field of food flavor chemistry. The method comprises the following steps: establishing a monomer molecule model for selected ferulic acid and sulfur-containing aroma substances; carrying out structure optimization and imaginary frequency interference elimination on the constructed monomer molecules; carrying out molecular surface electrostatic potential distribution calculation on the monomer after structure optimization and imaginary frequency interference elimination; docking the monomer molecules with the optimized structure to form a binary compound model; carrying out molecular surface electrostatic potential distribution calculation on the binary complex model, and calculating quantitative molecular surface analysis energy through molecular surface electrostatic potential distribution before and after molecular binding; and comparing quantitative molecular surface analysis energy before and after molecular combination to judge the release change of the sulfur-containing aroma substance. The method overcomes the defects of the research technology of interaction between aroma substances, and is simple and rapid, visual and reliable in result and wide in applicability.

Description

Technical Field

[0001] The present invention relates to the field of food flavor chemistry, and particularly to a method for computationally analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances. Background Art

[0002] Sulfur-containing aroma substances (such as methanethiol, dimethyl trisulfide, etc.), as important contributors to food flavor, are widely present in fermented products, baked foods, and meat processed products. These substances are generated through the Maillard reaction and thiamine pyrolysis, and endow foods with characteristic sensory experiences such as meaty aroma and caramel aroma. As a plant-derived polyphenol compound, the unique phenolic hydroxyl group and acrylic acid conjugated structure of ferulic acid have been proven to be able to regulate the dynamic release of sulfur-containing substances through a hydrogen bond network and effectively inhibit the generation of off-flavors caused by the oxidation of thioether substances. However, the mechanism of its effect on the release of sulfur-containing aroma substances has not been clarified.

[0003] Currently, gas chromatography-mass spectrometry combined with sensory evaluation is generally used in the industry for aroma analysis, but there are two major technical bottlenecks: First, instrument detection can only reflect the total amount of static volatile substances and cannot dynamically characterize the influence of intermolecular interactions on the release efficiency; Second, sensory evaluation is significantly affected by individual olfactory threshold differences, resulting in poor result reproducibility. Although molecular simulation technology has been maturely applied in the field of drug design, a systematic analysis method has not yet been formed in the field of food flavor regulation. Summary of the Invention

[0004] Therefore, in order to overcome the above-mentioned shortcomings of the prior art, the present invention provides a method for computationally analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances. Calculating the effect of ferulic acid on the release of sulfur-containing aroma substances using the molecular surface electrostatic potential distribution has the characteristics of high precision, high accuracy, and strong repeatability, and can solve the problems of single characterization means and poor repeatability in the current research on the effect of ferulic acid on the release of sulfur-containing aroma substances.

[0005] To achieve the above object, the present invention provides a method for calculating and analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances, including: Step 1, constructing molecular visualization models of ferulic acid, sulfur-containing aroma substances, and binary complexes of ferulic acid and sulfur-containing aroma substances; Step 2, optimizing the molecular structure models of ferulic acid, sulfur-containing aroma substances, and binary complexes of ferulic acid and sulfur-containing aroma substances through a calculation program based on molecular theory to obtain wave functions; Step 3, using the wave functions calculated by the calculation program to optimize the structures of ferulic acid, sulfur-containing aroma substances, and binary complexes of ferulic acid and sulfur-containing aroma substances to obtain stable spatial configurations; Step 4, calculating the molecular surface electrostatic potential distributions of the optimized molecular structures of ferulic acid, sulfur-containing aroma substances, and binary complexes of ferulic acid and sulfur-containing aroma substances; Step 5, comparing the changes in the molecular surface electrostatic potential distributions of ferulic acid, sulfur-containing aroma substances, and binary complexes of ferulic acid and sulfur-containing aroma substances to calculate the quantitative molecular surface analysis energy; Step 6, judging the effect of ferulic acid on the release of sulfur-containing aroma substances based on the quantitative molecular surface analysis energy.

[0006] In one embodiment, dimethyl trisulfide is selected as the sulfur-containing aroma substance in Step 1.

[0007] In one embodiment, GaussianView 5.0 is selected as the tool for constructing molecular visualization models of ferulic acid, sulfur-containing aroma substances, and binary complexes of ferulic acid and sulfur-containing aroma substances in Step 1.

[0008] In one embodiment, the B3LYP / 6-311+G basis set is selected as the parameter of the calculation program in Step 2.

[0009] In one embodiment, the B3P86 / 6-311+G** basis set is selected as the parameter of the calculation program when calculating the molecular surface electrostatic potential distribution of ferulic acid and sulfur-containing aroma substances in Step 4.

[0010] In one embodiment, the B3P86 / 6-311+G** basis set is selected as the parameter of the calculation program when calculating the molecular surface electrostatic potential distribution of the binary complex of ferulic acid and sulfur-containing aroma substances in Step 4.

[0011] In one embodiment, the quantitative molecular surface analysis energy calculation in Step 5 adopts the formula

[0012] Calculation, where the unit of ΔG is kilojoules per mole, and the unit of the electrostatic potential is kilocalories per mole. The formula parameters are fitted to the experiment for the case of B3P86 / 6-311+G** level optimization and wave function analysis. In the formula, V minrefers to the minimum value of the electrostatic potential in the entire three-dimensional space, V s,max and V s,min are the maximum and minimum values of the electrostatic potential at the points on the molecular surface, respectively. A - is the surface area of the region where the electrostatic potential on the molecular surface is negative, refers to the average value of the electrostatic potential in the region where the electrostatic potential on the molecular surface is negative.

[0013] In one embodiment, the discrimination method for judging the influence of ferulic acid on the release of sulfur-containing aroma substances according to the quantitative molecular surface analysis energy in step 6 is as follows: when the absolute value of the quantitative molecular surface analysis energy of the binary complex of ferulic acid and sulfur-containing aroma substances is larger, it is determined that the effect of ferulic acid on hindering the release of sulfur-containing aroma substances is more obvious.

[0014] Compared with the prior art, the advantages of the present invention are as follows: through density functional theory, the calculation results of the molecular structures and electronic properties of ferulic acid, sulfur-containing aroma substances, and their binary complexes can be accurately provided. This method also has the characteristics of high precision, and can predict the changes in the molecular structures and energies of ferulic acid, sulfur-containing aroma substances, and their binary complexes, so as to better understand the interaction between ferulic acid and sulfur-containing aroma substances.

[0015] Moreover, this method is a brand-new method for studying the interaction between ferulic acid and sulfur-containing aroma substances, making up for the deficiencies in the research technology of the interaction between ferulic acid and sulfur-containing aroma substances. This method is simple and fast, with intuitive and reliable results and wide applicability. Brief Description of the Drawings

[0016] In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings required to be used in the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For those of ordinary skill in the art, other drawings can be obtained based on these drawings without creative efforts.

[0017] Figure 1 is a simplified diagram of the steps for calculating and analyzing the influence of ferulic acid on the release of sulfur-containing aroma substances in the embodiments of the present invention. Detailed Embodiments

[0018] The embodiments of the present application will be described in detail below with reference to the drawings.

[0019] The following describes the implementation manners of the present application through specific specific examples. Those skilled in the art can easily understand other advantages and effects of the present application from the content disclosed in this specification. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all embodiments. The present application can also be implemented or applied through other different specific implementation manners. Various details in this specification can also be modified or changed based on different viewpoints and applications without departing from the spirit of the present application. It should be noted that, without conflict, the following embodiments and the features in the embodiments can be combined with each other. Based on the embodiments in the present application, all other embodiments obtained by those of ordinary skill in the art without creative efforts belong to the scope of protection of the present application.

[0020] It should be noted that the following describes various aspects of embodiments within the protection scope of the present invention. It should be obvious that the aspects described herein can be embodied in a wide variety of forms, and any specific structure and / or function described herein is only illustrative. Based on the present application, those skilled in the art should understand that one aspect described herein can be implemented independently of any other aspect, and two or more of these aspects can be combined in various ways. For example, any number and aspects described herein can be used to implement the device and / or practice the method. In addition, this device and / or this method can be implemented using other structures and / or functions in addition to one or more of the aspects described herein.

[0021] It should also be noted that the diagrams provided in the following embodiments only illustrate the basic concept of the present application in a schematic manner. Only the components related to the present application are shown in the diagrams, rather than being drawn according to the number, shape, and size of the components in actual implementation. The type, quantity, and ratio of each component in its actual implementation can be an arbitrary change, and the component layout type may also be more complex.

[0022] In addition, in the following description, specific details are provided to facilitate a thorough understanding of the examples. However, those skilled in the art will understand that the described aspects can be practiced without these specific details.

[0023] As Figure 1 shown, an embodiment of the present application provides a method for calculating and analyzing the influence of ferulic acid on the release of sulfur-containing aroma substances based on the molecular surface electrostatic potential distribution, including the following steps:

[0024] Step 1, construct a molecular structure visualization model of ferulic acid, sulfur-containing aroma substances, and their binary complex.

[0025] Preferably, dimethyl trisulfide is selected as the research object among sulfur-containing aroma substances. Preferably, GaussianView 5.0 is selected as the tool for constructing the molecular visualization model of ferulic acid, sulfur-containing aroma substances, and their binary complexes.

[0026] Step 2: Optimize the molecular structure models of ferulic acid, sulfur-containing aroma substances, and the binary complex of ferulic acid and sulfur-containing aroma substances based on a computational program based on molecular theory calculations to obtain the molecular structure model of the wave function.

[0027] Using the Gaussian 09W software package, optimize the molecular structure models of ferulic acid, sulfur-containing aroma substances, and the binary complex of ferulic acid and sulfur-containing aroma substances based on a computational program based on molecular theory calculations to obtain the wave function. Preferably, the B3LYP / 6-311+G basis set is selected as the parameter of the computational program in the computational program parameters.

[0028] Step 3: Utilize the wave function calculated by the computational program to optimize the structures of ferulic acid, sulfur-containing aroma substances, and the binary complex of ferulic acid and sulfur-containing aroma substances to obtain stable spatial configurations.

[0029] Step 4: Calculate the molecular surface electrostatic potential distribution of the optimized molecular structures of ferulic acid, sulfur-containing aroma substances, and the binary complex of ferulic acid and sulfur-containing aroma substances.

[0030] Preferably, the B3P86 / 6-311+G** basis set is selected as the parameter of the computational program when calculating the molecular surface electrostatic potential distribution of ferulic acid and sulfur-containing aroma substances. Preferably, the B3P86 / 6-311+G** is selected as the parameter of the computational program when calculating the molecular surface electrostatic potential distribution of the binary complex of ferulic acid and sulfur-containing aroma substances.

[0031] Step 5: Compare the changes in the molecular surface electrostatic potential distributions of ferulic acid, sulfur-containing aroma substances, and the binary complex of ferulic acid and sulfur-containing aroma substances to calculate the quantitative molecular surface analysis energy.

[0032] Preferably, the quantitative molecular surface analysis energy is calculated according to the formula where the unit of ΔG is kJ / mol, the unit of the electrostatic potential is kcal / mol, and the formula parameters are fitted to the experiment for the case of B3P86 / 6-311+G** level optimization and wave function analysis. In the formula, V min refers to the minimum value of the electrostatic potential in the entire three-dimensional space, V s,max and V s,min are the maximum and minimum point values of the electrostatic potential on the molecular surface, respectively. A -is the surface area of the region where the electrostatic potential on the molecular surface is negative, refers to the average value of the electrostatic potential of the region where the electrostatic potential on the molecular surface is negative.

[0033] Step 6, judge the influence of ferulic acid on the release of sulfur-containing aroma substances by quantitatively analyzing the energy of the molecular surface.

[0034] In one embodiment, the discrimination method for judging the influence of ferulic acid on the release of sulfur-containing aroma substances according to the quantitatively analyzed energy of the molecular surface in Step 6 is as follows: when the absolute value of the quantitatively analyzed energy of the binary complex of ferulic acid and sulfur-containing aroma substances is larger, it is determined that the effect of ferulic acid on hindering the release of sulfur-containing aroma substances is more obvious.

[0035] The above method can accurately provide the calculation results of the molecular structures and electronic properties of ferulic acid, sulfur-containing aroma substances, and the binary complex of ferulic acid and sulfur-containing aroma substances through the electrostatic potential distribution on the molecular surface. This method also has the characteristics of high precision and can predict the changes in the molecular structures and energies of ferulic acid, sulfur-containing aroma substances, and their binary complex, so as to better understand the interaction between ferulic acid and sulfur-containing aroma substances.

[0036] Moreover, this method is a brand-new method for studying the interaction between sulfur-containing aroma substances and ferulic acid, making up for the deficiencies in the research technology of the interaction between ferulic acid and sulfur-containing aroma substances. This method is simple and fast, the results are intuitive and reliable, and it has wide applicability.

[0037] In one embodiment, dimethyl trisulfide is selected as the research object in Step 1 among sulfur-containing aroma substances.

[0038] In one embodiment, GaussianView 5.0 is selected as the tool for constructing the molecular visualization model of ferulic acid, sulfur-containing aroma substances, and their binary complex in Step 1.

[0039] In one embodiment, the B3LYP / 6-311+G basis set is selected as the parameter of the calculation program in the calculation program parameters in Step 2.

[0040] In one embodiment, the B3P86 / 6-311+G** basis set is selected as the parameter of the calculation program when calculating the electrostatic potential distribution on the molecular surface of ferulic acid and sulfur-containing aroma substances in Step 4.

[0041] In one embodiment, the B3P86 / 6-311+G** basis set is selected as the parameter of the calculation program when calculating the electrostatic potential distribution on the molecular surface of the binary complex of ferulic acid and sulfur-containing aroma substances in Step 4.

[0042] Example 1

[0043] Step 1: Use GaussianView 5.0 software to visually construct the molecular structure models of ferulic acid and dimethyl trisulfide monomers. Select the C1 point group to restrict structural changes, and visually construct the molecular structure model of the binary complex of ferulic acid and dimethyl trisulfide. Use the "clean" function to pre-optimize the above three groups of molecular structure models.

[0044] Step 2: Set the calculation program parameters for the three groups of models constructed in Step 1 to "opt-Freq" - B3LYP / 6-311+G basis set. Calculate the wave functions of the three groups of molecular structure models through Muitiwfn software and optimize their structures to obtain stable spatial configurations.

[0045] Step 3: Calculate the molecular surface electrostatic potential distribution for the three groups of molecular structure models after structural optimization. When calculating the molecular structures of ferulic acid and dimethyl trisulfide monomers, set the calculation program parameters to B3P86 / 6-311+G** - enable Muitiwfn software - select the option of "considering the van der Waals surface corresponding to all atoms" - output the calculation results, and select the unit as kcal / mol; when calculating the binary complex of ferulic acid and sulfur-containing aroma substances, set the calculation program parameters to B3P86 / 6-311+G** - enable Muitiwfn software - select the option of "considering the van der Waals surface corresponding to all atoms" - output the calculation results, and select the unit as kcal / mol. Calculate the molecular surface electrostatic potential distribution for the three groups of molecular structure models according to the above parameters respectively.

[0046] Step 4: From the calculation files of the molecular surface electrostatic potential distribution for the three groups of molecular structure models, it can be known the optimization parameters in the B3P86 / 6-311+G** level optimization and wave function analysis, the minimum value of the electrostatic potential in the three-dimensional space of the molecule, the maximum and minimum point values of the electrostatic potential on the molecular surface, the surface area of the region where the molecular surface electrostatic potential is negative, and the average value of the electrostatic potential in the region where the molecular surface electrostatic potential is negative.

[0047] Step 5: Calculate according to the formula for quantitative molecular surface analysis energy calculation where the unit of ΔG is kJ / mol and the unit of the electrostatic potential is kcal / mol. The formula parameters are fitted to the experiment for the case of B3P86 / 6-311+G** level optimization and wave function analysis. In the formula, V min refers to the minimum value of the electrostatic potential in the entire three-dimensional space, V s,max and V s,min are the maximum and minimum point values of the electrostatic potential on the molecular surface respectively. A - is the surface area of the region where the molecular surface electrostatic potential is negative. It refers to the average electrostatic potential value in the negative value region. The results are shown in the following table.

[0048]

[0049] According to the above table, it can be known that the free energy of the binary complex of ferulic acid and dimethyl trisulfide is greater than the sum of the monomer energies of ferulic acid and dimethyl trisulfide, indicating that ferulic acid has an inhibitory effect on dimethyl trisulfide.

[0050] The method of this embodiment is a brand-new method for studying the interaction between sulfur-containing aroma substances and ferulic acid, making up for the deficiencies in the research technology of the interaction between ferulic acid and sulfur-containing aroma substances. This method is simple and fast, the results are intuitive and reliable, and it has a wide range of applicability, helping people better understand the interaction between ferulic acid and sulfur-containing aroma substances, and providing a theoretical basis for designing high-quality food processing products.

[0051] The above is only the specific embodiment of the present application, but the protection scope of the present application is not limited thereto. Any changes or substitutions that can be easily thought of by those skilled in the art within the technical scope disclosed in the present application should be covered within the protection scope of the present application.

Claims

1. A method for calculating and analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances, characterized in that: include: Step 1, constructing a molecular visualization model for ferulic acid, sulfur-containing aroma substances, and a binary complex of ferulic acid and sulfur-containing aroma substances; Step 2, optimizing the molecular structure models of ferulic acid, sulfur-containing aroma substances, and binary complexes of ferulic acid and sulfur-containing aroma substances by a calculation program based on molecular theoretical calculation to obtain wave functions; Step 3, using the wave function calculated by the computing program, optimizing the structure of ferulic acid, sulfur-containing aroma substances, and the binary complex of ferulic acid and sulfur-containing aroma substances to obtain a stable spatial configuration; Step 4, calculating the molecular surface electrostatic potential distribution of the optimized molecular structures of ferulic acid, sulfur-containing aroma substances, and binary complexes of ferulic acid and sulfur-containing aroma substances; Step 5, comparing the changes in the molecular surface electrostatic potential distributions of ferulic acid, sulfur-containing aroma substances, and binary complexes of ferulic acid and sulfur-containing aroma substances to calculate the quantitative molecular surface analysis energy; Step 6, determining the effect of ferulic acid on the release of sulfur-containing aroma substances by quantitative molecular surface analysis energy.

2. The method for calculating and analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances according to claim 1, characterized in that: The sulfur-containing aroma substance in step 1 is dimethyl trisulfide.

3. The method for calculating and analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances according to claim 1, characterized in that: In the step 1, the Gaussian View tool is used to construct a molecular visualization model of ferulic acid, sulfur-containing aroma substances, and a binary complex of ferulic acid and sulfur-containing aroma substances.

4. The method for calculating and analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances according to claim 1, characterized in that: In step 2, the B3LYP / 6-311+G basis set is selected as the parameter of the calculation program.

5. The method for calculating and analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances according to claim 1, characterized in that: In the step 4, when calculating the surface electrostatic potential distribution of ferulic acid and sulfur-containing aroma substance molecules, the B3P86 / 6-311+G** basis set is selected as the parameter of the calculation program.

6. The method for calculating and analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances according to any one of claims 1 or 5, characterized in that: In the step 4, when calculating the molecular surface electrostatic potential distribution of the binary complex of ferulic acid and sulfur-containing aroma substances, the B3P86 / 6-311+G** basis set is selected as a parameter of the calculation program.

7. The method for calculating and analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances according to claim 1, characterized in that: The quantitative molecular surface analysis energy calculation in step 5 is calculated using the formula Calculation; where V min V refers to the minimum value of electrostatic potential in the entire three-dimensional space. s,max and V s,min are the maximum and minimum values ​​of the electrostatic potential on the molecular surface, A - is the surface area of ​​the molecule where the electrostatic potential is negative, It refers to the average value of the electrostatic potential in the negative region of the molecular surface.

8. The method for calculating and analyzing the effect of ferulic acid on the release of sulfur-containing aroma substances according to claim 1, characterized in that: The method for judging the effect of ferulic acid on the release of sulfur-containing aroma substances based on the quantitative molecular surface analysis energy in step 6 is: when the absolute value of the quantitative molecular surface analysis energy of the binary complex of ferulic acid and sulfur-containing aroma substances is larger, it is judged that the effect of ferulic acid in hindering the release of sulfur-containing aroma substances is more obvious.

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