JP7588930B2 - Method for isomerizing lycopene, composition containing cis-isomer lycopene and method for producing same - Google Patents

Description

Article 30, paragraph 2 of the Patent Act applies ▲1▼Publication name: Abstracts of the 32nd Carotenoid Research Symposium Distribution date: September 14, 2018 ▲2▼Meeting name and venue 32nd Carotenoid Research Symposium Kumamoto University, Kurokami Minami Campus, Faculty of Engineering Centennial Memorial Hall Date held: September 15, 2018 ▲3▼Publication name: Abstracts of the 2018 Japan Society for Food Science and Technology Chubu Branch Conference Distribution date: December 15, 2018 ▲4▼Meeting name and venue 2018 Japan Society for Food Science and Technology Chubu Branch Conference Meijo University, Tenpaku Campus, Common Lecture Building North Date held: December 15, 2018 ▲5▼Publication name: Abstracts of presentations at ifia JAPAN 2019 Carotenoid Forum Distribution date: May 23, 2019 ▲6▼Meeting name and venue ifia JAPAN 2019 Carotenoid Forum Tokyo Big Sight Aomi Exhibition Hall A & B Seminar Hall 101 Date held: May 23, 2019 ▲7▼Publication name: Scientific Reports, volume 9, Article number: 7979 (2019) Distribution date: May 28, 2019 ▲8▼Publication name: Abstracts of the 20th (2019) Annual Meeting of the Japan Society for Food Engineering Distribution date: July 25, 2019 ▲9▼Meeting name and venue The 20th (2019) Annual Meeting of the Japan Society for Food Engineering Kagawa International Conference Center Sunport Hall Takamatsu Conference Room Date held: August 7, 2019

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

Lycopene is a red pigment found in tomatoes and is a type of naturally occurring carotenoid compound. Lycopene has a strong antioxidant effect and is widely used as an additive in foods, beverages, cosmetics, medicines, animal feed, etc. Lycopene has 11 conjugated π bonds, so there are various cis isomers, and it is known that cis isomer lycopene (an isomer in which at least one of the 11 conjugated π bonds is a cis type) has better intestinal absorption than trans isomer lycopene (Non-Patent Document 1). In particular, 5-cis lycopene is known to be more stable and have higher antioxidant capacity than trans isomer and other cis isomers of lycopene (Non-Patent Documents 2, 3). However, the content of cis isomer lycopene in commercially available lycopene compositions is low, and most of them are trans isomers, so a composition containing a large amount of cis isomer lycopene is required to improve intestinal absorption.

As a method for isomerizing lycopene from trans to cis, 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 extracting lycopene in a supercritical fluid and heating it.

Special Publication No. 2007-522166 Special Publication No. 2010-500302 Special Publication No. 2010-502572 Special table 2015-051929 publication JP 2017-001959 A JP 2017-019756 A

Failla, et al., Journal of Nutrition, 2008, Vol. 138, pp. 482-486. Chasse et al., Journal of Molecular Structure (Theochem), 2001, Vol. 571, pp. 27-37. Muller, et al., Journal of Agricultural and Food Chemistry, 2011, Vol. 59, pp. 4504-4511.

The problem that this invention aims to solve is the efficient isomerization of trans-lycopene to cis-lycopene.

In light of the above, the inventors of the present application have conducted intensive research and discovered that a cyclic polysulfide or iodine is used as an isomerization catalyst, and is mixed with lycopene and fats and oils to carry out an isomerization reaction. In other words, 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 composition containing cis isomer lycopene and a method for producing the same. From this perspective, the present invention is defined as follows.

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, fats and oils, and an isomerization catalyst are mixed. In the heating step, lycopene, fats and oils, 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 concentration of lycopene per isomerization catalyst mixed (total lycopene (mM)/isomerization catalyst (mM)) is preferably 13 or less. The heating temperature may be 40°C or higher, and is preferably 80°C or higher. The cyclic polysulfide is preferably lenthionine, which is derived from a foodstuff that is widely eaten, 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 derived from a foodstuff that is widely eaten, such as seaweed or seafood.

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, fats and oils, and an isomerization catalyst are mixed. In the heating step, lycopene, fats and oils, 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, it is preferable that the concentration of lycopene per unit of isomerization catalyst mixed (total lycopene (mM)/isomerization catalyst (mM)) is 13 or less.

The cis-isomer lycopene-containing composition according to the present invention contains cis-isomer lycopene, fats and oils, and an isomerization catalyst. The 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 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 originates from a foodstuff that is widely eaten, for example, mushrooms of the Lentinus genus. Among mushrooms of the Lentinus genus, shiitake mushrooms are preferred, and dried mushrooms are more preferred. The iodine originates from a foodstuff that is widely eaten, for example, seaweed or seafood.

The food and drink of the present invention contains the above-mentioned cis-lycopene isomer-containing composition.

The present invention makes it possible to produce a composition containing cis-isomer lycopene by efficiently carrying out the cis-isomerization reaction of lycopene. In addition, 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.

Flow diagram of the method for producing the cis-isomer lycopene-containing composition An example of a chromatogram of cis-isomerized lycopene composition obtained by HPLC analysis.

<Composition containing cis-isomer lycopene>
The cis-isomer lycopene-containing composition according to the present embodiment (hereinafter referred to as "the composition") at least contains cis-isomer lycopene, fats and oils, and an isomerization catalyst. The 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 suitable for consumption. The raw materials do not exclude seasonings, food additives, and other food materials. The form of these raw materials is not important, and they may be solid or liquid.

<Lycopene>
The lycopene according to the present embodiment may be chemically synthesized, but is preferably derived from natural products derived from plants, animals, microorganisms, etc. Among them, lycopene derived from fruits and vegetables or lycopene synthesized by microorganisms is preferred, and lycopene derived from fruits and vegetables with a high lycopene content is more preferred. Examples of fruits and vegetables with a high lycopene content include tomatoes, watermelons, melons, grapefruits, persimmons, papayas, red guava navels, rose hips, carrots, and gac, with tomato processed products and oleoresin 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.

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, etc.

Oleoresin is a lipid fraction obtained by extracting fruits or vegetables or their juices from a sufficiently concentrated concentrate with an organic solvent or supercritical carbon dioxide, and then removing the solvent. The oleoresin may be mixed with a solvent, or may be oleoresin from which the oil has been removed. Oleoresin is commercially available, and an example is Lyc-O-Mato 15% (manufactured by LycoRed).

<Cis-isomer 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.

Compared to other cis-lycopene isomers, 5-cis-lycopene has a structure that is extremely stable in terms of thermoenergetics. 5-cis-lycopene is also 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 means that when used in products, it is possible to promote its high absorbability and antioxidant activity while ensuring an effective amount over a long period of time.

<Cisomer lycopene concentration>
The cis-lycopene isomer concentration can be calculated by multiplying the total lycopene concentration by the cis-lycopene isomer content. The cis-lycopene isomer content is the percentage (%) of the cis-lycopene to the total lycopene in the composition. The cis-lycopene isomer 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-lycopene isomer content (%) can be calculated by the following formula.

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

Cis-lycopene isomers are identified by the absorption spectrum and retention time of the peaks obtained by HPLC analysis. Figure 2 shows a chromatogram obtained by HPLC analysis of a composition containing cis-lycopene in section 16 of Example 2 described below. Among the peaks detected after the β-carotene peak and up to 5-cis-lycopene, those other than trans-lycopene can be identified as cis-lycopene. The absorption wavelength of lycopene changes slightly depending on the organic solvent in which lycopene is dissolved.

<5-cis-lycopene concentration>
The concentration of 5-cis-lycopene can be calculated by multiplying the lycopene concentration by the 5-cis-lycopene content. The 5-cis-lycopene content is the ratio (%) of 5-cis-lycopene to the total lycopene in the composition. The content of 5-cis-lycopene 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 content (%) of 5-cis-lycopene can be calculated by the following formula.

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

<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.

<Cyclic polysulfide>
A cyclic polysulfide satisfies the properties of both a cyclic compound and a polysulfide. A cyclic compound is a compound in which constituent atoms are bonded in a ring shape. A polysulfide is a compound having at least one or more sulfide bonds. Examples of cyclic polysulfides include lenthionine, tetrathiane, tetrathiolane, trithiolane, pentathiane, hexathiepane, and tetrathiepane, and may be natural or chemically synthesized. Among them, lenthionine is preferably used. Examples of natural products that contain a large amount of these cyclic polysulfides include mushrooms of the Lentinus genus, more specifically, shiitake mushrooms. Lenthionine, tetrathiane, and tetrathiolane are known as aroma components unique to shiitake mushrooms.

<Lentionine>
Lenthionine is a type of cyclic polysulfide known as the aroma component of shiitake mushrooms, and is also called pentathiepane (1,2,3,5,6-pentathiepane). Lenthionine may be extracted from shiitake mushrooms, but commercially available preparations can also be used. An example is 1,2,3,5,6-pentathiepane (manufactured by Fluorochem).

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.

Quantitation of lenthionine in shiitake mushrooms can be performed using GC-MS after organic solvent extraction.

<Iodine>
Iodine (I ₂ ) is an element that plays an important role as a component of thyroid hormone. This hormone is an essential mineral for the body, as 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 black seaweed. Examples of seafood include mackerel, cod, and abalone. There is no restriction on the method for quantifying the iodine contained in seaweed, and any known method can be used. For example, it is a method of incinerating seaweed and detecting it by gas chromatography.

Seaweed, seafood, or processed products thereof can also be used as an isomerization catalyst. In this case, the form of the seaweed, seafood, or processed products thereof is not important, and examples include a dried state or a rehydrated state. The seaweed or seafood used can be commercially available.

<Outline of the method for producing the composition>
1 shows a flow of the method for producing the present composition (hereinafter referred to as "the present method"). The present method mainly comprises mixing (S10) and heating (S20).

<Mixing (S10)>
In the mixing step, at least lycopene, fats and oils, and an isomerization catalyst are mixed. The purpose of mixing is to uniformly mix the substrate lycopene with the catalyst cyclic polysulfide or iodine. In addition, mixing the fats and oils promotes the isomerization of lycopene. The concentration of total lycopene per isomerization catalyst mixed (total lycopene (mM)/isomerization catalyst (mM)) may be 13 or less, preferably 1.3 or less, and more preferably 0.13 or less.

<Heating (S20)>
In the heating step, a mixture containing at least lycopene, fats and oils, and an isomerization catalyst (hereinafter referred to as the present mixture) is heated. The purpose of heating is to perform a thermal isomerization reaction to isomerize the trans-lycopene contained in the present mixture to cis-lycopene. The heating method is not limited, and examples include direct flame, steam, a water bath, and an oil bath. The heating temperature of the present mixture may be 40° C. or higher, and preferably 80° C. or higher, from the viewpoint that the thermal isomerization reaction is easily promoted. On the other hand, the higher the heating temperature, the more likely the decomposition of lycopene occurs, so the heating temperature is preferably 150° C. or lower. The heating time may be 30 minutes or more at 80° C. or lower, and more preferably 45 minutes or more. At temperatures higher than 80° C., the higher the temperature, the higher the reactivity, so the reaction time can be appropriately shortened. For example, at 120° C., the heating time may be 5 minutes or less.

<Cis-isomer lycopene concentration value of the present composition>
The cis-lycopene concentration of the composition depends on the total lycopene concentration in the mixture subjected to the heat treatment, and a composition having a high cis-lycopene concentration can be obtained when the total lycopene content is high. The cis-lycopene concentration (mM) per total lycopene (mM) in the composition is preferably 0.39 or more. The 5-cis-lycopene (mM) per total lycopene (mM) in the composition is preferably 0.071 or more, more preferably 0.10 or more.

<Uses of the composition>
The obtained composition can be used for various purposes, similar to the raw material lycopene. 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 food and drink, cosmetics, medicines, animal feed, etc. The food and drink is not particularly limited, but is preferably a seasoning, beverage, supplement (nutritional supplement), etc., and is particularly suitable for tomato-containing seasoning.

The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples.

Example 1
A tomato product (Kagome Tomato Paste HB Drum USA, Kagome Co., Ltd.) diluted to a total lycopene concentration of 12 mg/100 g was mixed with distilled water and olive oil (Nisshin Oillio Group Co., Ltd.) in a weight ratio of 60:35:5, and further mixed so that the final concentrations of the lenthionine or iodine catalysts were 0.01, 0.1, 1, and 10 mM. The control was one without the isomerization catalyst. The mixture was mixed uniformly in a mixer for 1 minute and then heated in a water bath at 80°C for 1 hour. The lycopene isomers were then quantified by HPLC. The results are shown in Table 1.

<Measurement of the proportion of cis-lycopene isomer in total lycopene>
1 g of this mixture was weighed, 30 ml of acetone (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 (Advantec, No. 2), dried in an evaporator, dissolved in 10 ml of hexane (Kanto Chemical, for HPLC), and passed through a 0.2 μm PTFE filter (Advantec) to obtain a sample to be subjected to HPLC. The obtained sample was subjected to HPLC under the following conditions, and the ratio of cis isomers was calculated by the above-mentioned calculation method.

<HPLC conditions>
Apparatus: Prominence LC-20AD, CTO-20AC, SIL-20A, SPD-M20A (Shimadzu Corporation), Column: Nucleosil 300-5 [stationary phase: fully porous silica gel, inner diameter: 4.6 mm x 250 mm, GL Sciences, 3 columns connected together],
Column temperature: 35° C.
Mobile phase: hexane (containing 0.075% DIPEA);
Flow rate of mobile phase: 1.0 mL/min,
Detector: photodiode array detector,
Detection wavelength: 460 nm.

Example 2
100.0 g of processed tomato (Tomato Paste HB Drum USA, Kagome Co., Ltd.) diluted to Bx 10.0, 5.0 g of extra virgin olive oil (Ajinomoto Co., Ltd.), and dried shiitake (sliced) (Kanesada Bussan Co., Ltd.) rehydrated with water or ground and powdered ma kombu (Minami Kayabe Fishery Cooperative Association) were added as isomerization catalysts in the amounts shown in Table 2, and then distilled water was added to make the total amount 140.0 g. For the control, distilled water was added instead of the isomerization catalyst to make the total amount 140.0 g. The method for rehydrating shiitake mushrooms was to add 8 times the weight of the dried shiitake mushrooms and store them in a refrigerator at 5°C for 16 hours. Then, the mixture was mixed uniformly in a mixer for 1 minute. After mixing, 35.0 g of the sample was weighed into a 50 ml polypropylene centrifuge tube and heated in a water bath under the conditions shown in Table 2. After heating, the samples were immediately cooled to room temperature or lower with cold water, and the lycopene isomers were quantified by HPLC. The conditions and results for each group are shown in Table 2. The method for quantifying lenthionine in shiitake mushrooms, the method for quantifying iodine in seaweed, the method for quantifying total lycopene concentration, and the HPLC conditions for measuring the cis-lycopene isomer ratio are shown below.

<Quantitative method for lenthionine>
The amount of lenthionine contained in shiitake mushrooms was quantified using GC-MS. As a pretreatment, 2.0 g of shiitake mushrooms were sampled in a container with a lid, and 20 ml of isooctane (2,2,4-trimethylpentane) was added to the sample. After shaking well for 1 minute, the isooctane layer (supernatant) was filtered through a 0.45 μm filter (13HP045AN, Toyo Roshi Kaisha, Ltd.) and used for analysis.

<GC-MS conditions>
Apparatus: 6890N, 7975C (manufactured by Agilent Technologies Company)
Analysis conditions Column: DB-5MS (30 m x 0.250 mm x 0.25 μm)
Inlet temperature: 200℃
Column temperature: 70°C (held for 2 minutes) - 10°C/min heating - 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 number: m/z 188, 142
<Method for quantifying iodine>
The amount of iodine contained in the isomerization catalyst was analyzed by gas chromatography (ashing method) at the request of the Japan Food Analysis Center, a general incorporated foundation. The specific analysis method was to place 2.0 g of crushed kelp in a nickel crucible, add 4 ml of 4 mol/L potassium hydroxide solution, 2 ml of 25% potassium nitrate solution, and 5 ml of ethanol to perform preliminary ashing, and then perform ashing 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 N0.5B filter paper, and the volume was adjusted to a constant volume in a 100 ml volumetric flask, and the appropriately diluted product was separated into a test tube with a stopper. Then, 1 ml of a mixture of equal amounts of sulfuric acid and distilled water, 1 ml of methyl ethyl ketone, and 1 ml of 200 ppm sodium nitrite solution were added and 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.

<GC conditions>
Apparatus: 6890N (manufactured by Agilent Technologies Company)
Detector: ECD
Column: DB-WAX [J&W scientific], φ250 μm × 30 m, film thickness 0.25 μm
Temperature: Sample injection port 200°C, detector 250°C
Column: 45°C (held for 2 minutes) → 10°C/min heating → 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: 1 μl
<Measurement of total lycopene concentration>
1.3 g of the composition was weighed out, and the volume was adjusted to 50 ml with acetone (Kanto Chemical Co., Ltd., for HPLC), and ultrasonic treatment was performed for 10 minutes. The solution after ultrasonic treatment was passed through a 0.45 μm PTFE filter (Advantec Co., Ltd.) to obtain a sample to be subjected to HPLC. The obtained sample was subjected to HPLC analysis under the following conditions.

Apparatus: Shimadzu high-performance liquid chromatograph LC-2030C Plus (manufactured by 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°C
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 from a commercially available lycopene reagent, and the weight and volume of the sample subjected to extraction.

<Measurement of cis-lycopene isomer ratio>
Approximately 1.3 g of the composition was weighed out, and the volume was adjusted to 50 ml with acetone (Kanto Chemical Co., Ltd., for HPLC), and ultrasonic treatment was performed for 10 minutes. The solution after ultrasonic treatment was suction filtered using filter paper (Kiriyama Seisakusho Co., Ltd., 5B filter paper), and dried with an evaporator (Tokyo Rikakiki Co., Ltd., NVC-2000), and then dissolved in 20 ml of hexane (Kanto Chemical Co., Ltd., for HPLC), and passed through a 0.45 μm PTFE filter (Advantec Co., Ltd.) to obtain a sample to be subjected to HPLC. The obtained sample was subjected to HPLC analysis under the following conditions.

<HPLC conditions>
Apparatus: Hitachi high performance liquid chromatograph Chromaster 5110, 5210, 5310, 5430 (manufactured by Hitachi High-Tech Science Corporation),
Column: Nucleosil 300-5 [stationary phase: fully porous silica gel, inner diameter: 4.6 mm x 250 mm, manufactured by GL Sciences, 3 columns connected together],
Column temperature: 30 ° C.
Mobile phase: hexane (containing 0.10% DIPEA);
Flow rate of mobile phase: 1.0 mL/min,
Detector: photodiode array detector,
Detection wavelength: 460 nm.

<Evaluation Results>
In Example 1, the values of cis-isomer lycopene concentration (mM)/total lycopene concentration (mM) were higher in all of Sections 1 to 7 than in the control. In addition, the higher the concentration of the isomerization catalyst, the more isomerization was promoted. In addition, the values of 5-cis-lycopene concentration (mM)/total lycopene concentration (mM) were higher in all of Sections 1 to 7 than in the control. In addition, there was a tendency that the higher the concentration of the isomerization catalyst, the higher the concentration of 5-cis-lycopene.

In Example 2, the cis-isomer lycopene concentration (mM)/total lycopene concentration (mM) values were higher in all of the sections 8 to 16 than in the control. In addition, in sections 8 to 10, the cis-isomer lycopene concentration (mM)/total lycopene concentration (mM) values in the composition were higher than in the control, even though the total lycopene concentration (mM)/lenthionine concentration (mM) values of the mixture were significantly higher than in sections 1 to 4 in Example 1. This is presumably because the lenthionine contained in the shiitake mushrooms was small, but other cyclic polysulfides functioned as isomerization catalysts. In section 11, the total lycopene concentration (mM)/iodine concentration (mM) was higher than in sections 5 to 7 in Example 1, resulting in lower values of the cis-isomer lycopene concentration (mM)/total lycopene concentration (mM) and the 5-cis-lycopene concentration (mM)/total lycopene concentration (mM). In section 12, the reaction time was short at 15 minutes, so the values of cis-isomer lycopene concentration (mM)/total lycopene concentration (mM) and 5-cis-lycopene concentration (mM)/total lycopene concentration (mM) 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 values of cis-isomer lycopene concentration (mM)/total lycopene concentration (mM) and 5-cis-lycopene concentration (mM)/total lycopene concentration (mM) were lower than in sections 15 and 16.

From the above, cyclic polysulfides and iodine function as lycopene isomerization catalysts and are useful for producing compositions containing cis-isomer lycopene.

The fields in which this invention is useful are pharmaceuticals, cosmetics, dietary supplements, functional foods, and general foods.

Claims (15)

A method for producing a cis-isomer lycopene-containing composition, comprising at least the following steps:
Mixing: what is mixed here is at least lycopene, fats and oils, and an isomerization catalyst;
Heating: Here, the lycopene, the fats and oils, and the isomerization catalyst are heated at the same time as or after mixing;
The origin of the lycopene is oleoresin ,
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 method of claim 1,
The concentration of lycopene per isomerization catalyst mixed (total lycopene (mM)/isomerization catalyst (mM)) is 13 or less. The method of claim 1 or 2,
The heating temperature is 40° C. or higher. The method of claim 3,
The heating temperature is 80° C. or higher. The manufacturing method according to any one of claims 1 to 4,
The origin of the lenthionine is a mushroom of the Lentinus genus. The method of claim 5,
The mushroom of the genus Lentinus is a shiitake mushroom. The method of claim 6,
The shiitake mushrooms are dried. A method for isomerizing lycopene comprising at least the following steps:
Mixing: what is mixed here is at least lycopene, fats and oils, and an isomerization catalyst;
Heating: Here, the lycopene, the fats and oils, and the isomerization catalyst are heated at the same time as or after mixing;
the isomerization catalyst is a cyclic polysulfide;
The cyclic polysulfide is lenthionine. 9. The method for isomerizing lycopene according to claim 8,
The concentration of lycopene per isomerization catalyst mixed (total lycopene (mM)/isomerization catalyst (mM)) is 13 or less. A cis-isomer lycopene-containing composition comprising:
Cis-isomer lycopene: wherein the cis-isomer lycopene per total lycopene (cis-isomer lycopene (mM)/total lycopene (mM)) is 0.39 or more;
The origin of the lycopene is oleoresin,
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 cis-isomer lycopene-containing composition of claim 10,
The 5-cis lycopene per total lycopene (5-cis lycopene (mM)/total lycopene (mM)) is 0.071 or more. The cis-isomer lycopene-containing composition of claim 10 or 11,
The origin of the lenthionine is a mushroom of the Lentinus genus. 13. The cis-isomer lycopene-containing composition of claim 12,
The mushroom of the genus Lentinus is a shiitake mushroom. 14. The cis-isomer lycopene-containing composition of claim 13,
The shiitake mushrooms are dried. A food or beverage,
It contains a cis-isomer lycopene-containing composition according to any one of claims 10 to 14.

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