JP7794549B2 - Method for isomerizing lycopene, composition containing cis-isomer lycopene and method for producing the same - Google Patents

Description

Article 30, paragraph 2 of the Patent Act applies ▲1▼Publication name: Abstracts of the 32nd Carotenoid Research Colloquium Distribution date: September 14, 2018 ▲2▼Meeting name, venue 32nd Carotenoid Research Colloquium Kumamoto University, Kurokami South Campus, Faculty of Engineering Centennial Memorial Hall Date held: September 15, 2018 ▲3▼Publication name: Abstracts of the 2018 Japanese Society for Food Science and Technology Chubu Branch Conference Distribution date: December 15, 2018 ▲4▼Meeting name, venue 2018 Japanese Society for Food Science and Technology Chubu Branch Conference Meijo University, Tempaku 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 Room 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 Annual Meeting of the Japan Society for Food Engineering (2019) Distribution date: July 25, 2019 ▲9▼Meeting name and venue Japan Society for Food Engineering 20th Annual Meeting (2019) Kagawa International Congress 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 a naturally occurring carotenoid compound. It possesses strong antioxidant properties and is widely used as an additive in foods, beverages, cosmetics, pharmaceuticals, animal feed, and more. Lycopene has 11 conjugated π bonds, resulting in various cis isomers. Cis-lycopene (an isomer in which at least one of the 11 conjugated π bonds is cis-form) is known to be better 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 higher 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 being trans-lycopene. Therefore, to improve intestinal absorption, a composition rich in cis-lycopene is required.

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 supercritical extraction and heating lycopene.

Special Publication No. 2007-522166 Special Publication No. 2010-500302 Special Publication No. 2010-502572 Special table 2015-051929 publication Japanese Patent Application Laid-Open No. 2017-001959 Japanese Patent Application Laid-Open No. 2017-019756

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 to improve the efficiency of isomerization of trans-lycopene to cis-lycopene.

In light of the above, the present inventors conducted extensive research and discovered a method for carrying out an isomerization reaction by mixing lycopene and fats and oils with a cyclic polysulfide or iodine as an isomerization catalyst. Specifically, 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, oil, and an isomerization catalyst are mixed. In the heating step, the lycopene, oil, and isomerization catalyst are heated. The heating step is performed simultaneously with or after the mixing. The isomerization catalyst is a cyclic polysulfide or iodine. The lycopene concentration per unit of isomerization catalyst (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 Lentinus mushrooms, shiitake mushrooms are preferred, with dried mushrooms being more preferred. The iodine is preferably derived from commonly eaten foodstuffs, such as seaweed or seafood.

The lycopene isomerization method of the present invention comprises at least a mixing step and a heating step. In the mixing step, at least lycopene, oil, and isomerization catalyst are mixed. In the heating step, lycopene, oil, and 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 cis-isomer lycopene-containing composition of the present invention contains cis-isomer lycopene, an oil or fat, and an isomerization catalyst. The cis-isomer lycopene per total lycopene (cis-isomer lycopene (mM)/total lycopene (mM)) is 0.39 or greater, 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 greater. The cyclic polysulfide is preferably lenthionine, which originates from a widely consumed food source, such as mushrooms of the genus Lentinus. Among mushrooms of the genus Lentinus, shiitake mushrooms are preferred, with dried mushrooms being more preferred. The iodine originates from a widely consumed food source, such as seaweed or seafood.

The food and beverage product according to the present invention contains the aforementioned cis-isomer lycopene-containing composition.

The present invention makes it possible to efficiently carry out the cis-isomerization reaction of lycopene, thereby producing 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, it is possible to easily obtain a composition containing cis-isomer lycopene that is highly absorbable by the intestinal tract and suitable for consumption.

Flowchart of the method for producing a 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 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 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.

<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.

Examples of tomato processed products include tomato juice, tomato puree, tomato paste, tomato pulp, and tomato powder. Tomato pulp is the sediment 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 and vegetables or their juices, which have been thoroughly concentrated, with an organic solvent or supercritical carbon dioxide, followed by removal of the solvent. The oleoresin may be mixed with a solvent, or the oil content of the oleoresin may be removed. Oleoresin is commercially available; for example, Lyc-O-Mato 15% (manufactured by LycoRed).

<Cis-isomer lycopene>
Cis isomers of lycopene contained in cis isomer 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 thermal energy. Furthermore, compared to trans-lycopene, 9-cis-lycopene, and 13-cis-lycopene, 5-cis-lycopene is known to have higher antioxidant activity and be more easily absorbed by the human body. A high 5-cis-lycopene content means that when used in products, it is possible to ensure effective amounts over a long period of time while promoting its high absorbability and antioxidant activity.

<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:

[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.

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 a composition containing cis-isomer lycopene in section 16 of Example 2, which will be described later. 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 the lycopene.

<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:

[5-cis lycopene content (%)] = ([5-cis lycopene peak area] / [total peak area of total lycopene]) × 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 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.

<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>
Cyclic polysulfides have the properties of both cyclic compounds and polysulfides (polysulfides). 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 containing a large amount of these cyclic polysulfides is a mushroom of the Lentinus genus, more specifically, shiitake mushroom. 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 ( _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 restriction on the method for quantifying iodine contained in seaweed, and known methods can be used. For example, it is possible to incinerate the seaweed and detect it using gas chromatography.

Seaweed, seafood, or processed products thereof can also be used as an isomerization catalyst. The form of the seaweed, seafood, or processed products is not important; for example, it can be in a dried state or a rehydrated state. Commercially available seaweed or seafood can be used.

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

<Mixing (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 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, 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, and the like. 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 appropriately shortened. For example, at 120°C, the heating time may be 5 minutes or shorter.

<Cis-isomer lycopene concentration of the present composition>
The cis-lycopene concentration of the composition depends on the total lycopene concentration in the mixture subjected to heat treatment, and a high total lycopene content results in a composition with a high cis-lycopene concentration. The cis-lycopene concentration (mM) per total lycopene (mM) in the composition is preferably 0.39 or more. Furthermore, 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 lycopene used as a raw material. In particular, the composition obtained by the production method of 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.

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

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

<Measurement of the proportion of cis-isomer lycopene in total lycopene>
1 g of this mixture was weighed, 30 ml of acetone (Sigma-Aldrich, analytical grade) was added, and ultrasonic treatment was performed for 10 minutes. The solution after ultrasonic treatment was suction filtered using filter paper (Advantec, No. 2) and evaporated to dryness. The solution was then dissolved in 10 ml of hexane (Kanto Chemical, HPLC grade) and passed through a 0.2 μm PTFE filter (Advantec) to obtain a sample for HPLC. The obtained sample was subjected to HPLC under the following conditions, and the proportion of cis isomers was calculated using 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 × 250 mm, GL Sciences, three columns connected together);
Column temperature: 35°C,
Mobile phase: hexane (containing 0.075% DIPEA),
Mobile phase flow rate: 1.0 mL/min
Detector: photodiode array detector,
Detection wavelength: 460 nm.

Example 2
100.0 g of processed tomato product (Tomato Paste HB Drum USA, Kagome Co., Ltd.) diluted to Bx 10.0, 5.0 g of extra virgin olive oil (Ajinomoto Co., Inc.), and rehydrated dried shiitake mushrooms (sliced) (Kanesada Bussan Co., Ltd.) or ground and powdered ma kombu (Minami Kayabe Fisheries Cooperative Association) were added as isomerization catalysts in the amounts listed in Table 2, followed by distilled water to a total of 140.0 g. For the control, distilled water was added instead of the isomerization catalyst to a total of 140.0 g. Shiitake mushrooms were rehydrated by adding 8 times the weight of the dried shiitake mushrooms in distilled water and storing them in a refrigerator at 5°C for 16 hours. The mixture was then uniformly mixed 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 listed in Table 2. After heating, the samples were immediately cooled to room temperature or below in cold water, and the lycopene isomers were quantified by HPLC. The conditions and results for each group are shown in Table 2. The methods for quantifying lenthionine in shiitake mushrooms, iodine in seaweed, and total lycopene concentration, as well as the HPLC conditions for measuring the cis-lycopene ratio, are shown below.

<Method for quantifying lenthionine>
The lenthionine content of shiitake mushrooms was quantified using GC-MS. As a pretreatment, 2.0 g of shiitake mushrooms were sampled in a lidded container, and 20 ml of isooctane (2,2,4-trimethylpentane) was added. The sample was then shaken well for 1 minute, and the isooctane layer (supernatant) was filtered through a 0.45 μm filter (13HP045AN, Toyo Roshi Kaisha, Ltd.) 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/minute temperature increase - 250°C (10 minutes)
Ion source temperature: 230°C
Injection volume: 2μl
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 quantitative analysis of the iodine contained in the isomerization catalyst was performed by gas chromatography (ashing method) at the request of the Japan Food Analysis Center, a general incorporated foundation. Specifically, 2.0 g of crushed kelp was placed in a nickel crucible, and 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. The mixture was then ashed for approximately 3 hours in an electric furnace at 500 ° C. After cooling, water was added and heated on a hot plate at 100 ° C. for 30 minutes. The mixture was filtered through N0.5B filter paper, and the volume was adjusted to a constant volume in a 100 ml volumetric flask. The appropriately diluted mixture was then dispensed into a stoppered test tube. 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/minute temperature increase → 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 amount: 1 μl
<Measurement of total lycopene concentration>
1.3 g of the composition was weighed out, adjusted to 50 ml with acetone (Kanto Chemical, HPLC grade), and subjected to ultrasonic treatment for 10 minutes. The solution after ultrasonic treatment was passed through a 0.45 μm PTFE filter (Advantec Co., Ltd.) to obtain a sample for HPLC analysis. The obtained sample was subjected to HPLC analysis under the following conditions.

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°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 separately from a commercially available lycopene reagent, and the weight and volume of the sample subjected to extraction.

<Measurement of cis-isomer lycopene ratio>
Approximately 1.3 g of the composition was weighed, adjusted to 50 ml with acetone (Kanto Chemical Co., Ltd., for HPLC), and subjected to ultrasonic treatment for 10 minutes. The solution after ultrasonic treatment was suction filtered using filter paper (Kiriyama Manufacturing Co., Ltd., 5B filter paper), dried in 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 for HPLC analysis. 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 Inc., used in three columns connected together]
Column temperature: 30°C,
Mobile phase: hexane (containing 0.10% DIPEA),
Mobile phase flow rate: 1.0 mL/min
Detector: photodiode array detector,
Detection wavelength: 460 nm.

<Evaluation results>
In Example 1, the ratio of cis-isomer lycopene concentration (mM)/total lycopene concentration (mM) was higher in all of Sections 1 to 7 than in the control. Furthermore, the higher the concentration of the isomerization catalyst, the more isomerization was promoted. Furthermore, the ratio of 5-cis-lycopene concentration (mM)/total lycopene concentration (mM) was higher in all of Sections 1 to 7 than in the control. Furthermore, the higher the concentration of the isomerization catalyst, the higher the 5-cis-lycopene concentration tended to be.

In Example 2, the cis-isomer lycopene concentration (mM)/total lycopene concentration (mM) values were higher in all of the samples in sections 8 to 16 than in the control. Furthermore, even though the total lycopene concentration (mM)/lenthionine concentration (mM) values of the mixtures in sections 8 to 10 were significantly higher than those in sections 1 to 4 in Example 1, the cis-isomer lycopene concentration (mM)/total lycopene concentration (mM) values of the compositions were higher than those of the control. This is presumably because the lenthionine contained in the shiitake mushrooms was minimal, but other cyclic polysulfides functioned as isomerization catalysts. In section 11, the total lycopene concentration (mM)/iodine concentration (mM) values were higher than those in 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 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 invention is useful in the fields of pharmaceuticals, cosmetics, nutritional supplements, functional foods, and general foods.

Claims (3)

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 . 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 . 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.