Method for isomerizing lycopene, composition containing cis-isomer lycopene and method for producing the same

Abstract

To increase efficiency of isomerization from trans-form lycopene to cis isomer lycopene.SOLUTION: The inventor of the present application has found by devoted examination that a cyclic polysulfide or iodine is used as an isomerization catalyst for lycopene. That is, there is provided a method for efficiently isomerizing lycopene from trans-form to cis isomer by mixing and heating lycopene, fat and an isomerization catalyst. A composition containing cis isomer lycopene and a method for manufacturing the composition are also provided.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a method for isomerizing lycopene, a composition containing cis-isomer lycopene, and a method for producing the same. [Background technology]

[0002] Lycopene is a red pigment found in tomatoes and a naturally occurring carotenoid compound. Lycopene has strong antioxidant properties and is widely used as an additive in foods, beverages, cosmetics, pharmaceuticals, animal feed, and other products. Lycopene has 11 conjugated π bonds, resulting in various cis isomers. Cis-lycopene (an isomer containing at least one cis-form bond among the 11 conjugated π bonds) is known to be more readily absorbed in the intestinal tract than trans-lycopene (Non-Patent Document 1). In particular, 5-cis-lycopene is known to be more stable and have a stronger antioxidant capacity than trans-lycopene and other cis-lycopene isomers (Non-Patent Documents 2 and 3). However, commercially available lycopene compositions contain a low content of cis-lycopene, with most containing trans-lycopene. Therefore, to improve intestinal absorption, a composition rich in cis-lycopene is required.

[0003] As a method for isomerizing lycopene from trans to cis isomers, Patent Document 1 discloses a method of photoisomerizing lycopene in an organic solvent using iodine as a catalyst. Patent Documents 2 and 3 disclose methods of heating lycopene in an organic solvent together with a solid catalyst. Patent Document 4 discloses a method of dissolving lycopene in an organic solvent and irradiating it with light of a specific wavelength. Patent Document 5 discloses a method of dissolving and dispersing lycopene in sesame oil and heating it. Patent Document 6 discloses a method of supercritical extraction and heating lycopene. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Special Publication No. 2007-522166 [Patent Document 2] Special Publication No. 2010-500302 [Patent Document 3] Special Publication No. 2010-502572 [Patent Document 4] Special Publication No. 2015-051929 [Patent Document 5] Japanese Patent Application Publication No. 2017-001959 [Patent Document 6] Japanese Patent Application Publication No. 2017-019756 [Non-patent literature]

[0005] [Non-Patent Document 1] Failla, et al., Journal of Nutrition, 2008, Vol. 138, pp. 482-486. [Non-patent document 2] Chasse, et al., Journal of Molecular Structure (Theochem), 2001, Vol. 571, pp. 27-37. [Non-patent document 3] Muller, et al., Journal of Agricultural and Food Chemistry, 2011, Vol. 59, pp. 4504-4511. Summary of the Invention [Problem to be solved by the invention]

[0006] The problem to be solved by the present invention is to improve the efficiency of isomerization of trans-lycopene to cis-lycopene. [Means for solving the problem]

[0007] Based on the above, the present inventors have conducted extensive research and found that a cyclic polysulfide or iodine is used as an isomerization catalyst to mix with lycopene and fats and oils to carry out an isomerization reaction. That is, the present invention provides a method for efficiently isomerizing lycopene from the trans isomer to the cis isomer by mixing lycopene, fats and oils and an isomerization catalyst and heating the mixture, as well as a cis isomer lycopene-containing composition and a method for producing the same. From this perspective, the present invention is defined as follows.

[0008] The method for producing a cis-isomer lycopene-containing composition according to the present invention comprises at least a mixing step and a heating step. In the mixing step, at least lycopene, a fat or oil, and an isomerization catalyst are mixed. In the heating step, lycopene, a fat or oil, and an isomerization catalyst are heated. The heating step is performed simultaneously with or after the mixing. The isomerization catalyst is a cyclic polysulfide or iodine. Here, the lycopene concentration per unit of isomerization catalyst mixed (total lycopene (mM) / isomerization catalyst (mM)) is preferably 13 or less. The heating temperature is 40°C or higher, preferably 80°C or higher. The cyclic polysulfide is preferably lenthionine, which is derived from commonly eaten foodstuffs, such as mushrooms of the Lentinus genus. Among mushrooms of the Lentinus genus, shiitake mushrooms are preferred, and dried mushrooms are more preferred. The iodine is preferably derived from commonly eaten foodstuffs, such as seaweed or seafood.

[0009] The lycopene isomerization method according to the present invention comprises at least a mixing step and a heating step. In the mixing step, at least lycopene, a fat or oil, and an isomerization catalyst are mixed. In the heating step, the lycopene, a fat or oil, and the isomerization catalyst are heated. The heating step is carried out simultaneously with or after the mixing. The isomerization catalyst is a cyclic polysulfide or iodine. Here, the concentration of lycopene per unit of isomerization catalyst mixed (total lycopene (mM) / isomerization catalyst (mM)) is preferably 13 or less.

[0010] The cis-isomer lycopene-containing composition of the present invention contains cis-isomer lycopene, an oil or fat, and an isomerization catalyst. The ratio of cis-isomer lycopene per total lycopene (cis-isomer lycopene (mM) / total lycopene (mM)) is 0.39 or more, and the isomerization catalyst is a cyclic polysulfide or iodine. Furthermore, the ratio of 5-cis-lycopene per total lycopene (5-cis-lycopene (mM) / total lycopene (mM)) is 0.071 or more. The cyclic polysulfide is preferably lenthionine, which is derived from a widely eaten foodstuff, such as mushrooms of the genus Lentinus. Among mushrooms of the genus Lentinus, shiitake mushrooms are preferred, and dried mushrooms are more preferred. The iodine is preferably derived from a widely eaten foodstuff, such as seaweed or seafood.

[0011] The food and drink according to the present invention contains the above-mentioned cis-isomer lycopene-containing composition. [Effects of the Invention]

[0012] The present invention makes it possible to efficiently carry out the cis-isomerization reaction of lycopene to produce a composition containing cis-isomer lycopene. Furthermore, by using cyclic polysulfides contained in shiitake mushrooms, which are widely consumed, or iodine contained in seaweed or seafood as a catalyst, a composition containing cis-isomer lycopene that is highly absorbable by the intestinal tract and suitable for consumption can be easily obtained. [Brief explanation of the drawings]

[0013] [Figure 1] Flowchart of the method for producing a cis-isomer lycopene-containing composition [Figure 2] An example of a chromatogram of cis-isomerized lycopene composition obtained by HPLC analysis DETAILED DESCRIPTION OF THE INVENTION

[0014] <Composition containing cis-isomer lycopene> The cis-isomer lycopene-containing composition according to this embodiment (hereinafter referred to as "the composition") contains at least cis-isomer lycopene, fats and oils, and an isomerization catalyst. Details of the cis-isomer lycopene, fats and oils, and the isomerization catalyst will be described later. Other raw materials and ingredients (hereinafter referred to as "raw materials") are not particularly limited as long as they are edible. These raw materials do not exclude seasonings, food additives, and other food ingredients. The form of these raw materials is not important and may be solid or liquid.

[0015] <Lycopene> The lycopene according to the present embodiment may be chemically synthesized, but is preferably derived from natural products such as plants, animals, and microorganisms. Lycopene derived from fruits and vegetables or lycopene synthesized by microorganisms is particularly preferred, with those derived from fruits and vegetables with a high lycopene content being more preferred. Examples of fruits and vegetables with a high lycopene content include tomatoes, watermelons, melons, grapefruits, persimmons, papayas, red guava navels, rosehips, carrots, and gac, with processed tomatoes and oleoresins being particularly preferred. The lycopene may be in a liquid form or in a semi-solid or solid form such as a concentrate or dried product.

[0016] Examples of tomato processed products include tomato juice, tomato puree, tomato paste, tomato pulp, and tomato powder. Tomato pulp is the precipitate obtained by centrifuging tomato juice, tomato puree, or tomato paste. Tomato powder is a dried powder of tomato paste, tomato pulp, tomato skin, or the like.

[0017] Oleoresin is a lipid fraction obtained by extracting fruits and vegetables or their juices with an organic solvent or supercritical carbon dioxide, followed by removal of the solvent. Oleoresin may be mixed with a solvent, or may be oleoresin from which the oil content has been removed. Oleoresin is commercially available, for example, Lyc-O-Mato 15% (manufactured by LycoRed).

[0018] <Cisomer lycopene> Cis isomers of lycopene contained in cis lycopene include mono-cis isomers such as 5-cis lycopene, 9-cis lycopene, and 13-cis lycopene, and di-cis isomers such as 9,13'-cis lycopene and 5,9'-cis lycopene.

[0019] Compared to other cis-lycopene isomers, 5-cis-lycopene has a structure that is thermoenergetically very stable. Furthermore, 5-cis-lycopene is known to have higher antioxidant activity and be more easily absorbed by the human body than trans-lycopene, 9-cis-lycopene, and 13-cis-lycopene. A high 5-cis-lycopene content makes it possible to advertise its high absorbability and antioxidant activity while ensuring effective amounts over a long period of time when used in products.

[0020] <Cisomer lycopene concentration> The cis-isomer lycopene concentration can be calculated by multiplying the total lycopene concentration by the cis-isomer lycopene content. The cis-isomer lycopene content is the ratio (%) of cis-isomer lycopene to the total lycopene in the composition. The cis-isomer lycopene content can be measured by HPLC (high performance liquid chromatography) using a reverse-phase column or a normal-phase column, and is calculated based on the peak area of ​​each lycopene peak in the chromatogram. More specifically, the cis-isomer lycopene content (%) can be calculated using the following formula:

[0021] [Cisomer lycopene content (%)] = ([Total peak area of ​​cis isomer lycopene] / [Total peak area of ​​total lycopene]) × 100 Here, total lycopene refers to the sum of trans-lycopene and cis-lycopene, and cis-lycopene refers to the sum of all cis-lycopene isomers.

[0022] Cis-isomer lycopene is identified by the absorption spectrum and retention time of the peak obtained by HPLC analysis. Figure 2 shows a chromatogram obtained by HPLC analysis of the cis-isomer lycopene-containing composition in section 16 of Example 2 described below. Peaks detected after the β-carotene peak and up to 5-cis-lycopene, other than trans-lycopene, can be identified as cis-isomer lycopene. The absorption wavelength of lycopene varies slightly depending on the organic solvent used to dissolve lycopene.

[0023] <5-cis-lycopene concentration> The 5-cis-lycopene concentration can be calculated by multiplying the lycopene concentration by the 5-cis-lycopene content. The 5-cis-lycopene content is the percentage (%) of 5-cis-lycopene relative to the total lycopene in the composition. The 5-cis-lycopene content can be measured by HPLC (high-performance liquid chromatography) using a reverse-phase column or a normal-phase column, and is calculated based on the peak area of ​​each lycopene peak in the chromatogram. More specifically, the 5-cis-lycopene content (%) can be calculated using the following formula:

[0024] [5-cis lycopene content (%)] = ([5-cis lycopene peak area] / [total peak area of ​​total lycopene]) × 100 <Oils> The fats and oils are esters of glycerin and fatty acids. The type of fats and oils is not important, but it is preferably animal-derived or plant-derived. Examples of animal-derived fats and oils include whale oil, shark oil, beef tallow, lard, butter, etc. Examples of plant-derived fats and oils include, but are not limited to, olive oil, soybean oil, rapeseed oil, sesame oil, etc.

[0025] <Isomerization catalyst> The purpose of adding the isomerization catalyst is to promote the cis-isomerization of lycopene by heating. The isomerization catalyst is a cyclic polysulfide or iodine.

[0026] <Cyclic polysulfide> A cyclic polysulfide has the properties of both a cyclic compound and a polysulfide (polysulfide). A cyclic compound is a compound in which constituent atoms are bonded in a ring. A polysulfide (polysulfide) is a compound having at least one sulfide bond. Examples of cyclic polysulfides include lenthionine, tetrathiane, tetrathiolane, trithiolane, pentathiane, hexathiepane, and tetrathiepane, and they may be natural or chemically synthesized. Among these, lenthionine is preferred. An example of a natural product that contains a large amount of these cyclic polysulfides is a mushroom of the genus Lentinus, more specifically, shiitake mushroom. Lenthionine, tetrathiane, and tetrathiolane are known as aroma components unique to shiitake mushrooms.

[0027] <Lentionine> Lenthionine, a type of cyclic polysulfide known as the aroma component of shiitake mushrooms, is also known as pentathiepane (1,2,3,5,6-pentathiepane). Lenthionine can be extracted from shiitake mushrooms, but commercially available preparations can also be used. For example, 1,2,3,5,6-pentathiepane (Fluorochem) is one example.

[0028] Shiitake mushrooms or processed products thereof can also be used as the isomerization catalyst. The form of the shiitake mushrooms is not particularly limited, but dried shiitake mushrooms are preferred because the lenthionine content tends to increase when dried. Shiitake mushrooms that have been rehydrated after drying can also be used. Commercially available shiitake mushrooms can be used.

[0029] The amount of lenthionine in shiitake mushrooms can be determined using GC-MS after organic solvent extraction.

[0030] <Iodine> Iodine (I2) is an element that plays an important role as a component of thyroid hormones. This hormone is an essential mineral for the body because it promotes metabolism and, in children, growth together with growth hormone. Foods that contain a lot of iodine include seaweed and seafood. Examples of seaweed include kelp, hijiki, and kurome. Examples of seafood include mackerel, cod, and abalone. There is no specific method for quantifying the iodine contained in seaweed, and known methods can be used. For example, the iodine can be ashed and detected by gas chromatography.

[0031] Seaweed, seafood, or processed products thereof can also be used as the isomerization catalyst. In this case, the form of the seaweed, seafood, or processed products thereof is not important, and for example, it can be in a dried state or a rehydrated state. Commercially available seaweed or seafood can be used.

[0032] <Outline of the method for producing the composition> Figure 1 shows the flow of the method for producing the present composition (hereinafter referred to as "the present method"), which mainly consists of mixing (S10) and heating (S20).

[0033] <Mixed (S10)> In the mixing step, at least lycopene, a fat or oil, and an isomerization catalyst are mixed. The purpose of mixing is to uniformly mix the lycopene substrate with the cyclic polysulfide or iodine catalyst. Furthermore, mixing the fat or oil promotes the isomerization of lycopene. The concentration of total lycopene per isomerization catalyst (total lycopene (mM) / isomerization catalyst (mM)) may be 13 or less, preferably 1.3 or less, and more preferably 0.13 or less.

[0034] <Heating (S20)> In the heating step, a mixture containing at least lycopene, a fat or oil, and an isomerization catalyst (hereinafter referred to as "the mixture") is heated. The purpose of heating is to isomerize the trans-lycopene contained in the mixture to the cis-lycopene isomer by a thermal isomerization reaction. Any heating method may be used, including direct flame, steam, a water bath, an oil bath, etc. The heating temperature for the mixture is sufficient to facilitate the thermal isomerization reaction, and is preferably 40°C or higher, and more preferably 80°C or higher. On the other hand, since the higher the heating temperature, the more likely lycopene decomposition occurs, the heating temperature is preferably 150°C or lower. At temperatures below 80°C, the heating time is sufficient to be 30 minutes or longer, and more preferably 45 minutes or longer. At temperatures higher than 80°C, the reactivity increases with increasing temperature, so the reaction time can be shortened as appropriate. For example, at 120°C, the heating time may be 5 minutes or shorter.

[0035] <Concentration of cis-isomer lycopene in this composition> The cis-lycopene concentration of the composition depends on the total lycopene concentration in the heat-treated mixture, and a higher total lycopene content results in a composition with a higher cis-lycopene concentration. The cis-lycopene concentration (mM) per total lycopene (mM) in the composition is preferably 0.39 or higher. Furthermore, the 5-cis-lycopene (mM) per total lycopene (mM) in the composition is preferably 0.071 or higher, more preferably 0.10 or higher.

[0036] <Uses of this composition> The obtained composition can be used for various purposes, similar to the lycopene used as a raw material. In particular, the composition obtained by the production method according to the present invention can be suitably used as a raw material or additive for foods and beverages, cosmetics, pharmaceuticals, animal feed, etc. The foods and beverages are not particularly limited, but are preferably seasonings, beverages, supplements (nutritional supplements), etc., and are particularly suitable for tomato-containing seasonings. [Example]

[0037] Examples are given below to explain the present invention in detail, but the present invention is not limited to these examples.

[0038] <Example 1> A tomato processed product (Kagome Tomato Paste HB Drum USA, manufactured by Kagome Co., Ltd.) diluted so that the total lycopene concentration was 12 mg / 100 g, distilled water, and olive oil (manufactured by Nisshin Oillio Group Co., Ltd.) were mixed at a weight ratio of 60:35:5. Further, each catalyst of lenthionine or iodine was mixed so that the final concentration became 0.01, 0.1, 1, 10 mM. The control was without adding an isomerization catalyst. After uniformly mixing it with a mixer for 1 minute, it was heated in a water bath at 80°C for 1 hour. Then, each isomer of lycopene was quantified by HPLC. The results are shown in Table 1.

[0039] <Measurement of the ratio of cis-isomer lycopene in total lycopene> 1 g of this mixture was weighed, 30 ml of acetone (manufactured by Sigma-Aldrich, for analysis) was added, and ultrasonic treatment was performed for 10 minutes. The solution after ultrasonic treatment was suction-filtered using filter paper (manufactured by Advantec, No. 2), dried by an evaporator, then dissolved in 10 ml of hexane (manufactured by Kanto Chemical Co., Inc., for HPLC), passed through a 0.2-μm PTFE filter (manufactured by Advantec), and a sample for HPLC was obtained. The obtained sample was subjected to HPLC under the following conditions, and the ratio of the cis-isomer was calculated by the above-described calculation method.

[0040] <HPLC conditions> Apparatus: Prominence LC-20AD, CTO-20AC, SIL-20A, SPD-M20A (manufactured by Shimadzu Corporation), Column: Nucleosil 300-5 [Stationary phase: fully porous silica gel, Inner diameter: 4.6 mm × 250 mm, manufactured by GL Sciences Inc., used in three connected columns], Column temperature: 35°C, Mobile phase: hexane (containing 0.075% DIPEA), Flow rate of the mobile phase: 1.0 mL / min, Detector: photodiode array detector, Detection wavelength: 460 nm.

[0041]

Table 1

[0042] <Example 2> 100.0 g of tomato processed product (tomato paste HB drum, made by Kagome Co., Ltd., USA) diluted to Bx10.0, 5.0 g of extra-virgin olive oil (made by Ajinomoto Co., Inc.), and rehydrated dried shiitake (sliced, made by Kanemasa Sangyo Co., Ltd.) or pulverized kombu (made by Minami Kayabe Fishermen's Cooperative Association) were added with the amounts shown in Table 2 as an isomerization catalyst, and then distilled water was added so that the total amount became 140.0 g. For the control, distilled water was added instead of the isomerization catalyst so that the total amount became 140.0 g. The method for rehydrating shiitake was to add 8 times the weight of dried shiitake in distilled water and store it in a refrigerator at 5°C for 16 hours. Then, it was uniformly mixed with a mixer for 1 minute. The mixed sample was weighed out in a 50 ml polypropylene centrifuge tube in an amount of 35.0 g and heated under the conditions shown in Table 2 using a water bath. The heated sample was immediately cooled with cold water to below room temperature, and each isomer of lycopene was quantified by HPLC. The conditions and results for each section are shown in Table 2. The quantification method for lentionin contained in shiitake, the quantification method for iodine contained in seaweed, the quantification method for the concentration of total lycopene, and the HPLC conditions for measuring the ratio of cis-isomer lycopene are shown below.

[0043] [[ID=1​​​​​​​Apparatus: 6890N, 7975C (manufactured by Agilent Technologies Company) Analysis condition column: DB-5MS (30m × 0.250mm × 0.25μm) Inlet temperature: 200°C Column temperature: 70°C (held for 2 minutes) - heated at 10°C / min - 250°C (10 minutes) Ion source temperature: 230°C Injection volume: 2 μl Injection method: Splitless Gas: Helium Gas flow rate: 1.5 ml / min Ionization method: EI Set mass numbers: m / z 188, 142 <Quantification method of iodine> Quantification of iodine contained in the isomerization catalyst was analyzed by gas chromatography (ashing method) by entrusting the Japan Food Analysis Center, a general incorporated foundation. The specific analysis method was as follows: 2.0 g of ground kelp was placed in a nickel crucible, 4 ml of 4 mol / L potassium hydroxide solution, 2 ml of 25% potassium nitrate solution, and 5 ml of ethanol were added for preliminary ashing, and then ashing was carried out in an electric furnace at 500°C for about 3 hours. After cooling, water was added and heated on a hot plate at 100°C for 30 minutes, filtered with No. 5B filter paper, made up to volume in a 100 ml volumetric flask, and an appropriately diluted sample was aliquoted into a test tube with a stopper. Then, 1 ml of a mixture of sulfuric acid and distilled water in equal amounts, 1 ml of methyl ethyl ketone, and 1 ml of 200 ppm sodium nitrite solution were added, left for 60 minutes, 10 ml of hexane was added and shaken, and the hexane layer was subjected to gas chromatography (GC) under the following conditions.

[0045] <GC conditions> Apparatus: 6890N (manufactured by Agilent Technologies Company) Detector: ECD Column: DB-WAX [J&W scientific], φ250μm × 30m, film thickness 0.25μm Temperature: Sample inlet 200°C, detector 250°C Column 45°C (held for 2 minutes) → heated at 10°C / min → 150°C (held for 5 minutes) Injection method: Splitless Gas flow rate: Helium (carrier gas) 1.2 ml / min Nitrogen (additional gas) 30.0 ml / min Injection volume: 1μl <Measurement of total lycopene concentration> 1.3 g of the composition was weighed out, adjusted to 50 ml with acetone (Kanto Chemical, for HPLC), and subjected to ultrasonic treatment for 10 minutes. The solution after ultrasonic treatment was passed through a 0.45 μm PTFE filter (Advantec) to obtain a sample for HPLC analysis. The obtained sample was subjected to HPLC analysis under the following conditions.

[0046] Apparatus: Shimadzu high-performance liquid chromatograph LC-2030C Plus (Shimadzu Corporation) Column: L-column [stationary phase: ODS, inner diameter: 4.6 mm x 150 mm, manufactured by Chemicals Evaluation and Research Institute, Japan] Column temperature: 40℃ Sample injection volume: 10 μL Mobile phase: Acetonitrile / methanol / tetrahydrofuran (55:40:5 (v / v)) mixture (containing 50 ppm of α-tocopherol) Flow rate: 1.5mL / min Detection wavelength: 453 nm The total lycopene concentration was calculated from the peak area in the chromatogram obtained by HPLC analysis based on a calibration curve prepared separately from a commercially available lycopene reagent, and the weight and volume of the sample subjected to extraction.

[0047] <Measurement of cis-isomer lycopene ratio> Weighed about 1.3 g of the composition, made up the volume to 50 ml with acetone (manufactured by Kanto Chemical Co., Inc., for HPLC), and performed ultrasonic treatment for 10 minutes. The solution after ultrasonic treatment was suction filtered using filter paper (manufactured by Kiriyama Seisakusho, No. 5B filter paper), dried with an evaporator (manufactured by Tokyo Rikakikai Co., Ltd., NVC-2000), then dissolved in 20 ml of hexane (manufactured by Kanto Chemical Co., Inc., for HPLC), passed through a 0.45 μm PTFE filter (manufactured by ADVANTEC), and obtained a sample for HPLC. The obtained sample was subjected to HPLC analysis under the following conditions.

[0048] <HPLC Conditions> Apparatus: Hitachi High-Speed Liquid Chromatograph Chromaster 5110, 5210, 5310, 5430 (manufactured by Hitachi High-Technologies Corporation), Column: Nucleosil 300-5 [Stationary phase: fully porous silica gel, inner diameter: 4.6 mm × 250 mm, manufactured by GL Sciences Inc., used with three columns connected in series], Column temperature: 30 °C, Mobile phase: hexane (containing 0.10% DIPEA), Flow rate of the mobile phase: 1.0 mL / min, Detector: Photodiode array detector, Detection wavelength: 460 nm.

[0049]

Table 2

[0050] <Evaluation Results> In Example 1, for all of Sections 1 to 7, the value of the cis-isomer lycopene concentration (mM) / total lycopene concentration (mM) was higher than that of the control. Also, the higher the concentration of the isomerization catalyst, the more the isomerization was promoted. Moreover, for all of Sections 1 to 7, the value of the 5-cis-lycopene concentration (mM) / total lycopene concentration (mM) was higher than that of the control. Also, the higher the concentration of the isomerization catalyst, the more the concentration of 5-cis-lycopene tended to increase.

[0051] In Example 2, the cis-isomer lycopene concentration (mM) / total lycopene concentration (mM) values ​​for all of Sections 8 to 16 were higher than those for the control. Furthermore, even though the total lycopene concentration (mM) / lenthionine concentration (mM) values ​​for Sections 8 to 10 were significantly higher than those for Sections 1 to 4 in Example 1, the cis-isomer lycopene concentration (mM) / total lycopene concentration (mM) values ​​for the compositions were higher than those for the control. This is presumably because the lenthionine content in the shiitake mushrooms was low, but other cyclic polysulfides functioned as isomerization catalysts. In Section 11, the total lycopene concentration (mM) / iodine concentration (mM) values ​​were higher than those for Sections 5 to 7 in Example 1, resulting in lower cis-isomer lycopene concentration (mM) / total lycopene concentration (mM) and 5-cis-lycopene concentration (mM) / total lycopene concentration (mM). In Section 12, the reaction time was short at 15 minutes, so the cis-isomer lycopene concentration (mM) / total lycopene concentration (mM) and 5-cis-lycopene concentration (mM) / total lycopene concentration (mM) values ​​were lower than in Section 14, which was reacted for 30 minutes.In Section 13, the reaction temperature was low at 30°C, so the cis-isomer lycopene concentration (mM) / total lycopene concentration (mM) values ​​and 5-cis-lycopene concentration (mM) / total lycopene concentration (mM) values ​​were lower than in Sections 15 and 16.

[0052] From the above, it can be seen that cyclic polysulfides and iodine function as lycopene isomerization catalysts and are useful for producing a composition containing cis-isomer lycopene. [Industrial Applicability]

[0053] The invention is useful in the fields of pharmaceuticals, cosmetics, dietary supplements, functional foods, and general foods.

Claims

1. A method for producing a cis-isomer lycopene-containing composition, comprising at least the following steps: Mixing: At least lycopene, fats and oils, and an isomerization catalyst are mixed here; Heating: Here, the lycopene, the fat or oil, and the isomerization catalyst are heated, and the heating time is simultaneous with or after mixing; The lycopene is derived from a processed tomato product, The tomato processed product is one or more of tomato juice, tomato puree, tomato paste, tomato pulp, and tomato powder, The lycopene concentration in the lycopene-containing composition is 0.13 mM or more; the isomerization catalyst is a cyclic polysulfide, The cyclic polysulfide is lenthionine, The concentration of lycopene per isomerization catalyst mixed (total lycopene (mM) / isomerization catalyst (mM)) is 13 or less.

2. A cis-isomer lycopene-containing composition comprising: cis-isomer lycopene: wherein the cis-isomer lycopene per total lycopene (mM cis-isomer lycopene / mM total lycopene) is 0.39 or more; The lycopene concentration in the lycopene-containing composition is 0.13 mM or more; Isomerization catalyst: wherein the isomerization catalyst is a cyclic polysulfide; and, It is an oil and fat, The cyclic polysulfide is lenthionine, The concentration of lycopene per isomerization catalyst (total lycopene (mM) / isomerization catalyst (mM)) is 13 or less.

3. The cis-isomer lycopene-containing composition of claim 2, The 5-cis lycopene per total lycopene (5-cis lycopene (mM) / total lycopene (mM)) is 0.071 or more.

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