WO2019181529A1 - Plante de capsicum aromatique - Google Patents

Plante de capsicum aromatique Download PDF

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Publication number
WO2019181529A1
WO2019181529A1 PCT/JP2019/009049 JP2019009049W WO2019181529A1 WO 2019181529 A1 WO2019181529 A1 WO 2019181529A1 JP 2019009049 W JP2019009049 W JP 2019009049W WO 2019181529 A1 WO2019181529 A1 WO 2019181529A1
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Prior art keywords
capsicum
pepper
capsaicinoid
vanillyl
plant
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PCT/JP2019/009049
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English (en)
Japanese (ja)
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哲也 関
雅文 太田
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味の素株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
    • A01H6/00—Angiosperms, i.e. flowering plants, characterised by their botanic taxonomy
    • A01H6/82—Solanaceae, e.g. pepper, tobacco, potato, tomato or eggplant
    • A01H6/822—Capsicum sp. [pepper]
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
    • A01H6/00—Angiosperms, i.e. flowering plants, characterised by their botanic taxonomy
    • A01H6/82—Solanaceae, e.g. pepper, tobacco, potato, tomato or eggplant
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/81—Solanaceae (Potato family), e.g. tobacco, nightshade, tomato, belladonna, capsicum or jimsonweed
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants

Definitions

  • the present invention relates to a red pepper having an aroma component and a low pungent taste, a method for producing the same, and a composition containing the red pepper.
  • Capsicum sp. Plants are widely used around the world as foods, spices and pharmaceutical ingredients.
  • the pungent component is a group of substances consisting of 12 or more homologues such as capsaicin and dihydrocapsaicin, and is collectively called capsaicinoid.
  • capsaicin is known to have various physiological activities, for example, effects such as suppression of obesity by enhancement of energy metabolism based on promotion of adrenaline secretion (non-patent literature). 1, 2).
  • capsaicinoid has a problem that its use as a food or a food additive or a medicine is limited because its use amount is limited because of its strong pungency and invasiveness.
  • Capsinoids are known to have the same energy metabolism promoting effect, obesity suppressing effect, immunostimulating effect and the like as capsaicinoids.
  • food compositions and pharmaceutical compositions containing capsinoids are disclosed (Patent Document 1), and obesity inhibitors, body fat accumulation inhibitors, and adrenergic secretion promoters containing capsinoids as active ingredients are disclosed. (Patent Document 2).
  • a blood circulation promoting external preparation has been reported as a cosmetic (Patent Document 3).
  • capsaicinoid is a compound in which a fatty acid is amide-bonded to vanillylamine
  • capsinoid is a compound in which a fatty acid is ester-bonded to vanillyl alcohol (Non-Patent Document). 4). So far, capsiate, dihydrocapsiate and nordihydrocapsiate have been reported as capsinoids.
  • Patent Document 4 extraction methods from capsicum
  • Patent Document 5 drying methods
  • Patent Document 6 removal of the placenta portion containing a lot of pungent taste of pepper has been performed (Patent Document 6), but the operation is complicated and costly.
  • the capsicum with high capsaicinoid content is highly irritating, making it difficult to avoid dangerous work.
  • Capsicum sp. Is characterized by its pungency, redness and aroma, and is used as a variety of spices. Its main purpose is generally pungent. On the other hand, some peppers have a strong fragrance that is desirable for food depending on the variety, but at the same time, they contain a pungent component and are widely known as a material for imparting a pungent taste, and are actively used as a fragrance. None before.
  • vanillylamine is formed via phenylalanine as a precursor, ferulic acid, vanillin, etc.
  • capsaicinoids are biosynthesized by branched chain fatty acids and capsaicinoid synthase, but contain the above-mentioned capsinoids
  • p-AMT aminotransferase
  • capsioid-containing peppers dominated the reduction reaction from vanillin to vanillyl alcohol in place of the transamination reaction from vanillin to vanillylamine, and as a result of esterification reaction with branched chain fatty acids, capsinoids It has been reported that the production of capsaicinoid greatly increases and the production of capsaicinoid significantly decreases (Patent Document 7). In addition, a method for selecting such a plant body has also been reported (Patent Document 8).
  • Non-patent Document 17 studies have been conducted on the stability in various solvents. It has been reported that capsinoids are decomposed in the presence of water, methanol and ethanol to produce vanillyl alcohol, vanillyl methyl ether and vanillyl ethyl ether, respectively. However, this study has been conducted on the stable retention of capsinoids, and no studies have been made on the production of useful flavors and compounds by actively using capsinoids as reaction substrates. In the past, vanillyl alcohol and vanillyl ethyl ether have been reported as vanillyl alcohol derivatives in vanilla beans as sweet flavors having a weak pungent taste (Patent Document 9, Non-Patent Document 18).
  • Vanillyl ethyl ether is known as a Sweet and Smoky flavor that is also registered in FEMA GRAS (Non-Patent Documents 19, 20, and 21), and is an important aroma component that constitutes the scent in vanilla beans. It is added as a flavor to various foods such as bread, dairy products, gum, candy, and coffee, and since there are many requests for natural products, it is sold by multiple companies, but it is insufficient for supply (non- Patent Document 20).
  • vanilla beans containing vanillyl ethyl ether and fragrances extracted from vanilla beans are chemically synthesized from eugenol, guaiacol, etc. It is widely used in high-class confectionery, cosmetics and the like that require aroma that cannot be obtained with inexpensive synthetic vanillin produced by decomposition of lignin (Patent Document 13).
  • vanillyl butyl ether is a flavor that is also registered in FEMA GRAS (Non-patent Documents 22 and 23), and is used as a flavor by mixing with vanillin etc. to make a scent of vanilla, or for cosmetic materials and oral use. It is used as a composition (Patent Document 14). Both vanillyl butyl ether and vanillyl ethyl ether have been reported as carbonic acid enhancers (Patent Document 15).
  • Non-patent Document 23 Moreover, like vanillyl ethyl ether, it is added as a flavor to various foods such as bread, dairy products, gum, candy, coffee and cereal (Non-patent Document 23). However, although many studies have been made in the past, there has been no report of producing vanillyl butyl ether from pepper, and no report of producing vanillyl butyl ether from capsinoid as a raw material.
  • Non-Patent Document 6 Non-Patent Document 6
  • Capsicum species capsicinoid varieties with high capsaicinoid content, such as Capsicum chinense species including Habanero and Boot Jolokia, and Capsicum frutescens species whose gene has been inherited by Boot Jolokia, contain various ester compounds and have a unique fruity nature. It has a strong flavor and is used for ethnic dishes including the effect of enhancing the taste (Non-Patent Documents 7, 8, and 11).
  • Non-patent Documents 7 and 8 there is a report that capsicinoid content is not less than 1.6 mg / g (per fresh weight) in capsicum having a fruity flavor (Non-patent Documents 7 and 8), and the strength of fruity flavor and sweet flavor is strong.
  • Non-Patent Documents 7 to 12 Because of the coexistence of savory and pungent taste, its use, including umami and sour taste, has been limited (Non-Patent Documents 7 to 12). When calculated using the value of a moisture content of 93.4% (non-patent document 13) of the same pepper (blue pepper) in fresh pepper, the capsaicinoid content of the above-mentioned pepper with the fruity flavor is 24.2 mg / g. It is a dry weight, and has a high value (Non-patent Document 14) compared with a Takatsume (3.2 mg / g dry weight) having a strong pungent taste and a habanero having a strong pungent taste (13.2 mg / g dry weight). The capsicum is restricted in eating.
  • Non-Patent Documents 9 and 10 Zapory Hot, Aji Dustrain 2, Caribbean Sweet, and Capsicum frucescens S3212, which are capsicum chinense species with p-AMT dysfunction, have been reported. However, it has not yet been popularized as a substitute for fruity fragrance, replacing strong hot pepper such as habanero (Non-patent Documents 15 and 16).
  • a low-pungency S3212 genotype of Capsicum frutescens caused by a mutation in the putative aminotransferase (p-AMT) gene Young-Jun Park, Tomotaro Nishikawa, Mineo Mamio, Genuine M pp 1-8 2015 (Jun. 06) Stability of capsinoid in various solvents, Sutoh K, Kobata K, Watanabe T., J Agric Food Chem., 2001, 49 (8), 4026-4030.
  • FEMA GRAS reference 3815 https://www.femaflavor.org/flavor-library/vanillyl-ethyl-ether vanillyl ethyl ether http://www.thegoodscentscompany.com/data/rw1434631.html
  • FEMA GRAS reference 3796 https://www.femaflavor.org/flavor-library/vanillyl-butyl-ether vanillyl butyl ether http://www.thegoodscentscompany.com/data/rw1038461.html
  • the pungent taste which is the biggest feature of red peppers, limited the use of varieties other than the pungent taste of pepper, such as ⁇ flavor '', ⁇ flavor '', ⁇ sweetness '', ⁇ umami '' and ⁇ acidity ''
  • An object of the present invention is to provide a novel natural plant, a composition thereof, and a method for producing them, which can remove the pungent taste and enhance and impart characteristics other than the pungent taste.
  • the present inventors crossed a capsicin-rich capsicum with a capsicum in which the biosynthetic pathway of vanillylamine was suppressed, and the selected capsicum varieties were removed from the ⁇ pungency ''.
  • the inventors have found that the scent and flavor can be utilized to the maximum, and have completed the present invention (see FIG. 1).
  • R1 and R2 are each independently a methyl group
  • [4] The plant according to any one of [1] to [3], wherein the compound of formula (I) is selected from the group consisting of vanillyl pivalic acid esters and analogs thereof.
  • [5] The plant according to any one of [1] to [4], wherein the compound of formula (I) is contained in the fruit in a total amount of 0.01 mg or more per gram of dry weight of the fruit.
  • [6] The plant according to any one of [1] to [5], wherein the fruit contains 0.5 mg or more of capsinoid per gram of dry weight.
  • [7] The plant according to any one of [1] to [6] obtained by the following steps: (1) Capsicum line and capsicum chinense, capsicum annuum, capsicum frucense or capsicum baccatum with suppressed biosynthesis pathway of vanillylamine Obtaining an F1 population by crossing with a species; (2) obtaining an F2 population by self-pollination of plants from the F1 population; (3) Breeding the F2 population and measuring capsaicinoid and capsinoid content in the fruit; (4) A step of selecting plants having a low capsaicinoid content and a high capsinoid content.
  • R is a methyl group
  • R1 and R2 are each independently a methyl group
  • a saturated or unsaturated linear, branched or cyclic hydrocarbon group selected from the group consisting of m being 0 to 15 or 1 to 15) (excluding capsinoids) A method for producing a plant of the genus Capsicum containing at least one kind, wherein the plant contains 1 mg or less of capsaicinoid per 1 g of dry weight of the fruit: (1) A step of obtaining an F1 population by crossing a capsicum strain in which the biosynthesis pathway of vanillylamine is suppressed and a Capsicum chinense, Capsicum annuum, Capsicum fructense or Capsicum baccatum species; (2) obtaining an F2 population by self-pollination of pepper from the F1 population; (3) Breeding the F2 population and measuring capsaicinoid and capsinoid content in the fruit; (4) A step of selecting plants having a low capsaicinoid content and a high capsinoid content. [20] A step of adding alcohol, water or a mixture thereof to the plant
  • R is a methyl group
  • n 0 to 15).
  • the production method according to [20] further comprising a step of adding an alkaline substance.
  • vegetables, dried vegetables, extracts, processed products, and methods for producing the same can be used to maximize and widely use the “scent”, “flavor”, and “other flavors” of hot pepper after removing “pungency” Can be provided.
  • the range of use of flavors, etc. that had been restricted due to the pungent taste can be expanded, making it possible to use for various products.
  • a vanilla-like flavor can be added.
  • the peppers of the present invention are superior in fragrance strength. Since the present invention uses natural products, it can respond to consumers' safety and security orientations and natural orientations, and can be used as a substitute for "synthetic flavors and synthetic fragrances" to the maximum extent.
  • FIG. 1 shows a diagram comparing the pungent strength and fragrance strength of the fruit of the Capsicum plant of the present invention with existing varieties.
  • FIG. 2 shows GC-MS chromatograms of Example 17 and Comparative Example 12.
  • FIG. 3 shows GC-MS chromatograms of Example 18 and Comparative Example 13.
  • FIG. 4 shows GC-MS chromatograms of Comparative Examples 14-17.
  • R1 and R2 are each independently a methyl group
  • the present invention relates to a plant belonging to the genus Capsicum containing seeds and containing 1 mg or less of capsaicinoid per 1 g of the dry weight of the fruit (sometimes abbreviated as the plant of the present invention).
  • the plant belonging to the genus Capsicum of the present invention is characterized in that the content of capsaicinoid in the fruit is low.
  • the capsaicinoid content is usually 1 mg or less, preferably 0.5 mg or less, more preferably 0.25 mg or less, still more preferably 0.1 mg or less, and particularly preferably 0.05 mg or less per 1 g of the dry weight of the fruit.
  • the lower limit of the capsaicinoid content is preferably 0, and may be contained in an amount of about 0.03 mg or more.
  • the capsaicinoid content is the total amount of capsaicin, dihydrocapsaicin, and nordihydrocapsaicin.
  • Flavor is specifically a compound in which fatty acid and alcohol are ester-bonded, and capsicum chinense and capsicum fruitescens that are fragrant peppers such as habanero and boot jorochia It is known that these ester compounds substantially remain as a main component of fragrance (Non-patent Documents 7 and 8).
  • These structural formulas are represented by the following formula (I). Both are esters of saturated or unsaturated fatty acids and saturated or unsaturated alcohols.
  • the fatty acid may be linear or branched.
  • the alcohol may be linear or branched. Any combination of esters may be included.
  • the plant belonging to the genus Capsicum of the present invention contains at least one compound (also referred to as a compound of formula (I)) represented by the above formula (I) other than capsinoid.
  • R 1 and R 2 are each independently a saturated or unsaturated linear, branched or cyclic hydrocarbon group consisting of carbon and hydrogen, a methyl group,
  • M is 0 to 15, preferably 0 to 12, more preferably 0 to 9, and still more preferably 0 to 5.
  • M is 1 to 15, preferably 1 to 12, more preferably 1 to 9, and still more preferably 1 to 5.
  • R1 is a methyl group
  • Preferred examples include compounds in which m is 0 to 5.
  • Specific examples of the compound represented by the formula (I) are ester compounds having a molecular weight of 500 or less.
  • (E) -8-methyl-6-nonenoic acid 1-hexanol ester, 8-methylnonanoic acid 1-hexanol ester, 7-methyloctanoic acid 1-hexanol ester,
  • (E) -8-methyl-6-nonenoic acid 1-pentanol ester, 8-methylnonanoic acid 1-pentanol ester, 7-methyloctanoic acid 1-pentanol ester, vanillyl pival And acid esters and analogs thereof.
  • An analog is a compound having the same molecular weight as the compound.
  • vanillyl pivalic acid ester and its analog are more preferable.
  • the compound of formula (I) is usually 0.01 mg or more, preferably 0.1 mg or more, more preferably 0.15 mg or more, more preferably in the fruit as a total amount per 1 g of the fruit dry weight. Contains 0.2 mg or more, particularly preferably 0.5 mg or more. Although an upper limit is not specifically limited, Usually, it is 200 mg or less, 100 mg or less is preferable and 50 mg or less is more preferable.
  • the plant of the present invention contains capsinoids in the fruit in a total amount of usually 0.5 mg or more, preferably 0.7 mg or more, more preferably 1 mg or more per 1 g of the fruit dry weight.
  • an upper limit is not specifically limited, Usually, it is 100 mg or less, and 50 mg or less is preferable.
  • the plant of the present invention is not particularly limited as long as it contains the compound of the formula (I) and the capsaicinoid content is 1 mg or less per 1 g of the dry weight of the fruit, but is a hybrid of Capsicum chinense, Capsicum annuum, Capsicum fruccens or Capsicum baccatum species.
  • the biosynthesis pathway of vanillylamine is suppressed by methods such as breeding by breeding peppers whose biosynthesis pathway of vanillylamine was suppressed, capsicum, mutagenesis, genetic recombination, etc. where the biosynthesis pathway of selected vanillylamine was suppressed Pepper is preferred.
  • the selection can be performed by the method described in Patent Document 8 (JP2010-67A). However, the sorting method is not limited to this method.
  • red pepper strain in which the biosynthesis pathway of vanillylamine is suppressed C.I. annuum, C.I. chinense, C.I. Frucescens species, preferably C. aureus. Chinense species, among others, from the viewpoint of ease of cultivation, yield, etc.
  • a line obtained by crossing Aji Dulce or Aji Dulce, a line obtained by crossing Caribbean Sweet or Caribbean Sweet, or Zavory Hot or A line obtained by crossing the Zavory Hot is preferable, and a line obtained by crossing the Aji Dulce or Aji Dulce is more preferable.
  • Examples of varieties to be bred with capsicum with suppressed vanillylamine biosynthetic pathway include, for example, Capsicum annuum (CH-19 sweet, CH-19 spicy, himoto garashi, round salad, Yamato Akanban, Hawk's claw, eight bunch, Hontaka, Cayenne, Jalapeno, Explosive Ember, Pervian Purple, Birdseye, Sweet Chocolate Cherry, Pretty Purple, Sweet Cayenne, Thunder Mountain Longhorn, Chave Lovet, Curry Chile, Serrano, lenders Bird, Sapporo Daicho Namba, Chile Pecan, Hot Portugal, Maui Purple, Royal Black, Cedrino, Chile de Albor, Joe's Long, Yellow Pepper, Yatsufusa, etc.), C.I.
  • Frutescens red pepper, tabasco, Prickine Suan, S3212, etc.
  • C.I. Pubescens Rosto, Manzano Red Hot, etc.
  • hybrids thereof natural or artificial mutants, genetically modified plants, selected varieties, and the like.
  • Capsicum chinense, Capsicum annuum, Capsicum baccatum species or their hybrids are preferable.
  • C.I. chinense C.I. More preferred is a breeding variety using frutescens as a mating parent.
  • C.I. chinense, C.I. Among Frucescens, a crossbred that is crossed and selected using capsicinoids having a capsaicinoid content of 2 mg / g dry chili or more as a crossing parent is more preferable.
  • capsicum chinense habanero and infinity, boot joroquia, capsicum fruitence island chili, especially boot jorochia (boot jorochia is a cultivar that inherits both C. chinense and C. frucencece species DNA. ) Has a strong pungent taste and a strong fruity scent.
  • boot jorochia is a cultivar that inherits both C. chinense and C. frucencece species DNA.
  • Has a strong pungent taste and a strong fruity scent are crossed with Aji Dulce, a chili pepper whose biosynthesis pathway of vanillylamine is suppressed, and selected, so that natural vegetables that maintain and enhance the characteristics of these flavors and processed products such as extracts thereof can be obtained.
  • Aji Dulce a chili pepper whose biosynthesis pathway of vanillylamine is suppressed, and selected, so that natural vegetables that maintain and enhance the characteristics of these flavors and processed products such as extracts thereof can be obtained.
  • the plant of the present invention can be used as a composition as it is or with various additives added depending on the purpose.
  • capsinoids have been reported to react with alcohols to form various corresponding vanillyl alcohol ethers (Non-patent Document 17).
  • Mixing by spraying alcohol directly on pepper, cooking and brewing Etc., and mixing through extraction produces vanillyl alcohol and vanillyl alcohol ether that can be used as a flavor with a strong sweetness. Therefore, when used as a flavor, alcohol, water is added to the composition. Or it is preferable to add the mixture.
  • Alcohol is usually ethanol, propanol or butanol, preferably ethanol or butanol, from the viewpoints of use in food production, volatility as a flavor, safety and security.
  • an alkaline substance it is desirable to add an alkaline substance to the plant of the present invention in order to promote the reaction with alcohol.
  • an alkaline substance any substance can be used as long as it is a basic substance.
  • a food additive that can be used for food production or a food that can be tilted to the normal alkali side is desirable. .
  • alkaline substances include sodium hydroxide, potassium hydroxide, sodium bicarbonate, sodium carbonate, calcium carbonate, calcium hydroxide, calcium oxide, magnesium hydroxide, magnesium carbonate, sodium phosphate, barium hydroxide, ammonia, Ammonia water, basic amino acid, electrolyzed water and the like can be mentioned, but sodium hydroxide, potassium hydroxide, sodium bicarbonate, sodium carbonate, calcium carbonate, magnesium carbonate, ammonia, ammonia water, basic amino acid are preferable, sodium hydroxide Sodium bicarbonate, sodium carbonate, calcium carbonate, ammonia, aqueous ammonia, and basic amino acids are more preferable. Further, after the treatment with an alkaline substance, an appropriate treatment such as addition of an acidic substance can be performed.
  • the pH during the reaction after the addition of the alkali substance is not limited, it is usually at least pH 7 and preferably at least 7.5 from the viewpoint of promoting the reaction. Although an upper limit is not specifically limited, Usually, pH is 15 or less.
  • composition of the present invention it is desirable to add an excipient to the plant of the present invention in order to retain useful components after drying, improve dispersibility, and improve processing suitability.
  • excipient include dextrin, cyclodextrin, sucrose, lactose, starch, ⁇ -lactose, maltodextrin, ascorbic acid, tocophenol, gum arabic and the like. From the viewpoint of maintenance and storage stability of useful substances including flavor and other capsinoids, carotenoids, etc., cyclodextrin is preferable, and ⁇ -cyclodextrin or ⁇ -cyclodextrin is more preferable.
  • composition includes a compound represented by the following formula (II) (also referred to as a compound of formula (II)).
  • formula (II) also referred to as a compound of formula (II):
  • R is a linear or branched alkyl group, preferably a methyl group
  • n is 0 to 15, preferably 0 to 5.
  • R is a methyl group, an ethyl group,
  • the compound which is is mentioned preferably.
  • the compound of the formula (II) include vanillyl methyl ether, vanillyl ethyl ether, vanillyl propyl ether, vanillyl butyl ether and analogs thereof.
  • An analog is a compound having the same molecular weight as the compound.
  • vanillyl ethyl ether, vanillyl propyl ether, vanillyl butyl ether and analogs thereof are preferred from the viewpoints of use in food production, volatility as a flavor, safety and security, and vanillyl ethyl ether, vanillyl. Butyl ether is more preferred.
  • the compound of the formula (II) is usually contained in a total amount of 0.15 mg or more, preferably 0.2 mg or more, and usually 50 mg or less, preferably 30 mg or less, per 1 g of the fruit dry weight.
  • the compound of formula (II) can impart a sweet scent, vanilla scent, chocolate scent, Smoky scent, and fruity scent.
  • the plant and composition of the present invention have a weak pungent taste and retain and enhance the fragrance, flavor and flavor peculiar to pepper, and examples of the form include dried products, frozen products, refrigerated products, extracts and processed products.
  • the plant and composition of the present invention can be appropriately used depending on their use, whether or not sterilized.
  • the dried product is prepared by artificial drying, sun drying or the like.
  • sun drying for example, drying in about 5 to 15 days can be mentioned.
  • the artificial drying include a greenhouse treatment, a hot air treatment, a drum drying treatment, a freeze drying treatment, and the like, for example, drying in about 1 to 3 days.
  • the drying method is not limited to these methods, but the dried product in the present invention is preferably prepared by freeze drying or sun drying.
  • Refrigerated products and refrigerated products are prepared according to conventional methods, and processed products are prepared by processing methods such as crushing, crushing, grinding, extraction, concentration, dissolution, enzyme treatment, and acid-alkali treatment.
  • the plant extract of the present invention was subjected to chilling, freezing, heating, drying, crushing, pulverizing treatment, etc., as it was or as needed, the fruit portion of Capsicum sp. It is obtained by later extraction.
  • the extraction treatment method is not particularly limited, and can be performed according to a conventional method, and any apparatus can be used at low temperature, room temperature, and heating.
  • the extraction solvent is not particularly limited, but edible oils such as olive oil, rapeseed oil, safflower oil, soybean oil, sunflower oil, organic solvents such as hexane, ethanol, ethyl acetate, acetone, methanol, water, or a mixture thereof Extraction is possible under various conditions such as solvent. An acid, an alkali, etc.
  • Carbon dioxide extraction, steam distillation, etc. can also be used.
  • seasonings such as garlic, pepper, green onions and ginger
  • seasonings such as amino acids, salt, sugar, organic acids, and other additives are extracted and seasoned flavors are added. It can also be extracted.
  • these extracts can also be processed, such as powdered, depending on the application.
  • the extraction raw material is put into a container filled with the extraction solvent, and the soluble components are eluted with occasional stirring. At this time, the extraction conditions can be appropriately adjusted according to the type and part of the extraction raw material, but in the case of water, 5 to 100 ° C.
  • the plant and composition of the present invention are used as a substitute for a pepper having a general pungent taste, a pepper or paprika having a weak fragrance, a spice extract and its preparation, and a synthetic colorant.
  • it is used as pulverized products, extracts, oils, flavors and fragrances to be added to foods and chemicals, pharmaceuticals, health foods, beverages including alcoholic beverages, confectionery, and other processed products.
  • Synthetic flavors and synthetic fragrances are problematic in terms of safety and security, and Habanero, which is famous for its fruity fragrance and taste-improving effect, was certified in the Guinness Book of 1994-2006 as a pepper with the strongest pungency.
  • Habanero which is famous for its fruity fragrance and taste-improving effect, was certified in the Guinness Book of 1994-2006 as a pepper with the strongest pungency.
  • the use for foods is limited, and when the amount of pepper using the flavor is added to the food, strong pungency and irritation cannot be avoided.
  • Boot Jorokia is a hot pepper that was recognized in the Guinness Book in 2007 as a spicy pepper, and in its native Indian Assam language, Bif Jorokia Bih Jolkia, “poisonous chili”, Borbif Jorokia Borbih Jolokia, “Very poisonous” It is called “Chilli” and it is crushed and applied to the fence to repel elephants, so it cannot avoid strong pungent taste and irritation.
  • contact with the skin causes pain and inflammation, so protective equipment such as rubber gloves, masks, and goggles is used for handling. Therefore, the use of these peppers in foods and chemicals, pharmaceuticals, health foods, beverages including alcoholic beverages, confectionery, and other processed products is limited.
  • the plant and composition of the present invention solve these problems, and can become a more preferable pepper flavor, pepper pepper fragrance, and pepper processed product.
  • the total content of the compound of formula (I), which is an aroma component in the extract is 0.2 mg or more, preferably 0.5 mg or more, more preferably 1 mg or more, particularly preferably 2 mg or more, per 1 g of fruit dry weight. It is.
  • the total content of the compound of formula (I), which is an aroma component in the dried product, frozen product, refrigerated product, processed product, and composition is 0.01 mg or more, preferably 0.02 mg or more per 1 g of dry fruit weight. More preferably, it is 0.05 mg or more, and particularly preferably 0.1 mg or more.
  • the plant and composition of the present invention are less pungent and invasive than capsaicin, they can be suitably used as foods or pharmaceuticals or additives thereto.
  • the plant and composition of the present invention have effects of lowering blood triglyceride concentration, increasing blood free fatty acid concentration, increasing blood adrenaline level, increasing blood glucose concentration and increasing oxygen consumption.
  • it is useful for improving general nutritional status and improving health, such as suppression of obesity and improvement of metabolic state, such as transient improvement of hypoglycemia.
  • Examples of uses as pharmaceuticals include, for example, pharmaceuticals having various physiological activities such as energy metabolism activators, obesity inhibitors, body fat accumulation inhibitors, analgesics, adrenaline secretion promoters, endurance enhancers, etc. Can do.
  • plant and composition of the present invention when added to foods, they can be used as health foods or functional foods having various physiological activities as described above.
  • Plants and compositions of the present invention include, for example, dressing, camellia oil, salad oil, olive oil, rapeseed oil, soybean oil, rice oil, safflower oil, sunflower oil, and other oils, mayonnaise, sauce, butter, margarine, savory powder, cinnamon chili, shichimi Pepper, aubergine pepper, cola goose, yangyeom, gochujang, bean sauce, potato sauce, harissa, salsa, tabasco, kanzuri, chili pepper, chili powder, red pepper, maple grated, sauce, miso, soy sauce, salt, amino acid, nucleic acid, yeast Condiments such as beer, Japanese sake, shochu, brandy, whiskey, etc., fried rice flour, kimchi, pickles, sprinkles, bread, confectionery, pet food, side dish, toppings, canned food, meat, ham , Chinese food such as sausages, cup noodles, pizza, ramen, dumplings, mapo tofu, tacos, enchiladas, Ahita
  • composition ratio can be used at a known blending ratio, and since the pungent component is low, the blending may be changed depending on the taste and aroma.
  • flavors using capsicum chinense habanero When used as a raw material for capsicum oil, flavors using capsicum chinense habanero have a fruity flavor, sweetness, flavor and taste compared to flavors using capsicum annuum such as Takatsume and Hachibo.
  • capsicum annuum such as Takatsume and Hachibo.
  • the superiority of the effect has been recognized in the past, but the addition amount was limited due to the strong pungent taste.
  • the plant and composition of the present invention can utilize the fruity flavor and flavor of pepper as well as the effects of ester compounds possessed by capsicum chinense and capsicum fruitescens such as habanero in the widest range.
  • the plant and composition of the present invention have a sweet fragrance, a vanilla-like fragrance, a chocolate-like fragrance, a smokey fragrance, and a fruity fragrance as a fragrance imparting the flavor, fragrance, and flavor of pepper. It can be used as a flavoring agent.
  • the present invention is a method for producing a plant of the genus Capsicum containing at least one compound represented by the above formula (I), wherein the plant contains 1 mg or less of capsaicinoid per 1 g of the dry weight of the fruit,
  • a manufacturing method including the following steps is also included: (1) A step of obtaining an F1 population by crossing a capsicum strain in which the biosynthesis pathway of vanillylamine is suppressed and a Capsicum chinense, Capsicum annuum, Capsicum fructense or Capsicum baccatum species; (2) obtaining an F2 population by self-pollination of pepper from the F1 population; (3) Breeding the F2 population and measuring capsaicinoid and capsinoid content in the fruit; (4) A step of selecting plants having a low capsaicinoid content and a high capsinoid content.
  • a plant having a low capsaicinoid content means a capsaicinoid content of 1 mg or less per gram of dry fruit weight
  • a plant having a high capsinoid content means a plant having a capsinoid content of 0.5 mg or more per gram of dry fruit weight.
  • the breeding in (3) is a concept including cultivation and breeding. That is, (3) includes a step of measuring capsaicinoid and capsinoid content in the fruits of the F2 population. Moreover, you may include the process of breeding F2 population, measuring the compound content of Formula (I) in a fruit, and selecting the plant with high compound content of Formula (I).
  • a plant having a high content of the compound of the formula (I) means a plant having a compound content of the formula (I) of 0.01 mg or more per 1 g of fruit dry weight.
  • Capsaicinoid content, capsinoid content and the compound content of formula (I) are measured using high performance liquid chromatography (HPLC), detection system using ultraviolet absorption spectrum, mass spectrum, fluorescence spectrum, gas chromatography Examples of the detection system include a mass spectrum and a method using a flame ionization detector.
  • HPLC high performance liquid chromatography
  • breeding selection is to repeat selection of individuals and line cultivation for each selected individual, and to select and fix and make a pure line by comparing the lines in the separated generation of hybrids. It can be done by a method.
  • the cultivation method of the produced pepper is not particularly limited as long as it is a cultivation method usually used in pepper cultivation.
  • outdoor cultivation rain-free soil cultivation, rain-free hydroponics, plant factory cultivation, and multi-soil Cultivation cultivation etc. are mentioned.
  • the plant of the genus Capsicum of the present invention is a capsicum obtained by breeding selection by crossing, and does not include a capsicum by a gene recombination technique.
  • the chili pepper by the genetic recombination technique means a red pepper artificially introduced with a foreign gene by the genetic recombination technique, and does not mean a red pepper bred by crossing.
  • Various definitions, contents, and the like in the production method of the present invention are the same as described above.
  • the present invention also includes a method for producing the compound represented by the above formula (II).
  • the production method includes a step of adding alcohol, water or a mixture thereof to the plant of the present invention.
  • the amount of alcohol added is usually 0.1 to 10000 parts by weight, preferably 2 to 1000 parts by weight, per 1 part by weight of the plant of the present invention. Specific alcohol and the like are as described above.
  • the amount of water added is usually 0.1 to 10000 parts by weight, preferably 2 to 1000 parts by weight, per 1 part by weight of the plant of the present invention.
  • the manufacturing method may further include a step of adding an alkaline substance.
  • the addition amount of the alkaline substance is usually 0.001 to 10 parts by weight, preferably 0.001 to 1 part by weight, with respect to 1 part by weight of the plant of the present invention.
  • Specific alkaline substances are the same as described above.
  • the production method includes a step of adjusting the mixture of the plant, alcohol, water or a mixture thereof and an alkaline substance of the present invention to pH 7 or more.
  • the pH is usually 7 or more, but 7.5 or more is preferable from the viewpoint of considering unevenness of the reaction product. Although an upper limit is not specifically limited, Usually, pH is 15 or less. pH can be adjusted with alkaline substances, but after alkali treatment, organic acids such as citric acid, succinic acid and malic acid, inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid, vitamins such as amino acids, aspartic acid and pantothenic acid The process of adding and adjusting acidic substances, such as, may be included.
  • the manufacturing method may include conventional steps such as a stirring step and a heating step.
  • a stirring step and a heating step For example, after adding alcohol or the like and an alkaline substance to the plant of the present invention, the above formula (II) generated after stirring at ⁇ 20 to 70 ° C., preferably ⁇ 10 to 65 ° C. for 1 minute or longer, preferably 10 to 300 minutes.
  • recovering the represented compound is mentioned.
  • the reaction can also be advanced by adding plants to foods containing alcohol and storing them for a long time.
  • Examples of the method for recovering the compound represented by the above formula (II) include, but are not limited to, solvent extraction, supercritical fluid extraction, molecular distillation, and column chromatography.
  • the manufacturing method may further include a step of adding an excipient.
  • the excipient include dextrin, cyclodextrin, sucrose, lactose, starch, ⁇ -lactose, maltodextrin, ascorbic acid, tocophenol, gum arabic and the like.
  • cyclodextrin is preferable, and ⁇ -cyclodextrin or ⁇ -cyclodextrin is more preferable.
  • the amount of cyclodextrin added is usually 0.0001 to 10 parts by weight, preferably 0.01 to 1 part by weight per 1 part by weight of the plant of the present invention.
  • HPLC measurement conditions for capsaicinoid and capsinoid are as follows. All examples and comparative examples were quantified using this method. HPLC conditions: Column: YMC Trial Phenyl plus 3 ⁇ m (diameter 4.6 mm ⁇ 250 mm) Eluent: 70% (v / v) aqueous methanol detection: Fluorescence Ex 280 nm Em 320 nm Column oven temperature 40 ° C.
  • capsaicinoid preparation (capsaicin (Sigma Aldrich M2028), dihydrocapsaicin (Sigma Aldrich M1022), nordihydrocapsaicin (Nacalai Tesque 05085-31)), or capsinoid preparation (Patent No. 1) Based on the ratio of the respective peak areas of capsiate, dihydrocapsiate and nordihydrocapsiate synthesized under the conditions described in No. 4696588, the amounts were determined as capsaicinoid amounts and capsinoid amounts.
  • GC / MS Gas chromatograph / mass spectrometer
  • Capillary column trade name “DB-5ms” (122-5532G length 30 m, inner diameter 0.25 mm, film thickness 0.25 ⁇ m)
  • Oven temperature 40 ° C (0 to 1 minute) ⁇ 10 ° C / minute ⁇ 280 ° C (25 to 30 minutes)
  • Carrier gas He, 10 psi low-pressure air transfer line Temperature: 240 ° C
  • MS ion source temperature 230 ° C
  • MSQ pole temperature 150 ° C
  • Front inlet temperature 200 ° C
  • the extracted ions were the sum of (target ions ⁇ 0.5), the total ions were the sum of the ion range 35 to 1000, and the total value of the total chromatogram was the integrated value for 5 to 30 minutes after injection.
  • Raw fatty acids ((6E) -8-methyl-6-nonenoic acid ((6E) -8-Methyl-6-nonenoic acid; Santa Cruz sc-210575), 8-methylnonanoic acid (8-Methylnonanoic acid; CAY ( (Funakoshi) 9000310), 7-methyloctanoic acid (7-Methyloctanic acid; Santa Cruz sc-488478)) were weighed into a vial, followed by each alcohol (1-hexanol (Nacalai Tesque), 1-pentanol (Nacalai Tesque)).
  • Vanillyl alcohol (Tokyo Chemical Industry Co., Ltd. V0018), vanillyl ethyl ether (Tokyo Chemical Industry Co., Ltd. E1028), vanillyl butyl ether (Wako Pure Chemical Industries, Ltd. 321-80402, 323-80401) are purchased and standardized. Used as a product. Vanillyl methyl ether and vanillyl propyl ether were synthesized by mixing capsiate with methanol (Pure Chemical 73125-1230) and 1-propanol (Wako Pure Chemical Industries, Ltd. 162-04816), respectively. Mass ion peaks (168.1, 196.1) were obtained and used as standard products.
  • Example 1 Raw material used for freeze-dried pepper: Aji Dulce (purchased from Sunoyayasai, p-AMT (p-aminotransferase, vanillylamine is biosynthesized by this enzyme, which is an important enzyme in capsaicin biosynthesis.
  • Capsicum chinense spicy varieties pepper cultivar Infinity purchased from Tongarashi Yodogawa Co., Ltd. was selected for two generations. Varieties that have mutations in p-AMT and cannot synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials.
  • Raw material preparation The collected pepper was lyophilized for 2 days with a freeze dryer (FD-1000 manufactured by Tokyo Rika Kikai Co., Ltd.).
  • Preparation of ground vegetable products containing flavors Preparation of fine powder:
  • Raw material used Prepared according to the above raw material preparation method. In the preparation, first, the chili pepper was pulverized with Milser 800DG (Iwatani Corporation). The capsaicinoid content of the obtained product was 0.03 mg / g (0.003 g / 100 g), and was confirmed to be 0.003 g / 100 g or less. The capsinoid content measured at the same time was 6.0 mg / g.
  • Example 1 The results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows. ⁇ Ingestion of 1 mg “Fruity fragrance” 3 “Pungency” 0 ⁇ 10mg intake “Fruity fragrance” 5 “Pungency” 0 ⁇ 100mg intake “Fruity fragrance” 6 “Spicy” 1.5
  • the p-AMT-suppressed cultivar contained almost no capsaicinoid and was less irritating, while the fruity fragrance was enhanced, as compared with Comparative Example 1, which was the original species. Furthermore, since it was hypoallergenic, it was possible to take a high volume. Table 1 shows the sensory evaluation results of fragrance and capsaicinoid and capsinoid contents.
  • Example 2 Raw material using freeze-dried red pepper: Capsicum chinense hot pepper seed cultivar Boot Jolokia (purchased from Tongarashi Yodogawa Co., Ltd.) was cultivated, and fully matured reddish fruits were harvested and used as raw materials. Preparation of raw materials: The same method as in Example 1 was used. Preparation of pulverized vegetable product containing flavor: The same method as in Example 1 was used. The capsaicinoid content of the obtained product was 44.8 mg / g, which was estimated to be extremely high pungency and irritation. The capsinoid content measured simultaneously was 0.23 mg / g. The results of sensory evaluation when this ground sample was ingested are as follows. ⁇ 1mg intake “Fruity fragrance” 1 “Spicy” 6 Ingestion of 10 mg or more was difficult because the pungent taste was strong, and was interrupted. Table 1 shows the sensory evaluation results of fragrance and capsaicinoid and capsinoid contents.
  • Example 2 Freeze-dried red pepper used raw material: Aji Dulce (red pepper with suppressed p-AMT activity) was crossed with Capsicum chinense red pepper variety boot Jolokia (purchased from Tongarashi Yodogawa Co., Ltd.) and selected for 2 generations A variety that has a mutation in p-AMT and cannot synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same method as in Example 1 was used. Preparation of pulverized vegetable product containing flavor: The same method as in Example 1 was used.
  • the capsaicinoid content of the obtained product was 0.01 mg / g (0.001 g / 100 g), and was confirmed to be 0.003 g / 100 g or less.
  • the capsinoid content measured at the same time was 3.8 mg / g.
  • the results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows.
  • Example 3 Freeze-dried red pepper used raw material: Aji Dulce (red pepper with suppressed p-AMT activity) was crossed with Capsicum chinense spicy red pepper variety Habanero (purchased from Tongarashi Yodogawa Co., Ltd.). There are varieties that have mutations in p-AMT and cannot synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same method as in Example 1 was used. Preparation of pulverized vegetable product containing flavor: The same method as in Example 1 was used.
  • the capsaicinoid content of the obtained product was 0.02 mg / g (0.002 g / 100 g), and was confirmed to be 0.003 g / 100 g or less.
  • the capsinoid content measured at the same time was 1.0 mg / g.
  • the results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows.
  • Example 1 Compared with Example 1 and Example 2 which are cultivars crossed with Infinity and Boot Jolokia, Aji Dulce (p-AMT inhibitory varieties) contains almost no capsaicinoids and is hypoallergenic while being fruity. The scent was not very strong and was considered insufficient for use as a flavor. Table 1 shows the sensory evaluation results of fragrance and capsaicinoid and capsinoid contents.
  • Example 1 Compared with Example 1 and Example 2 which are varieties crossed with Infinity and Boot Jolokia, CH-19 sweet (p-AMT inhibitory varieties) contains almost no capsaicinoid and is hypoallergenic, Even the mature fruit did not almost have a fruity fragrance, and was considered insufficient for use as a flavor.
  • Table 1 shows the sensory evaluation results of fragrance and capsaicinoid and capsinoid contents.
  • Example 4 Raw capsicum raw material: Aji Dulce (capsicum with suppressed p-AMT activity) was crossed with Capsicum chinense spicy spruce cultivar Infinity (purchased from Tongarashi Yodogawa Co., Ltd.) There are varieties that have mutations in p-AMT and are almost unable to synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw material: The collected pepper was stored frozen. Preparation of ground vegetable product containing flavor: Raw material used: Prepared according to the above raw material preparation method. In the preparation, first, the chili pepper was pulverized with Milser 800DG (Iwatani Corporation).
  • the results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows. ⁇ 1mg intake “Fruity fragrance” 2.5 “Pungency” 0 ⁇ 10mg intake “Fruity fragrance” 5 “Pungency” 0 ⁇ 100mg intake “Fruity fragrance” 6 “Spicy” 1
  • the frozen p-AMT-suppressed variety was hypoallergenic while having a strong fruity scent. Furthermore, since it was hypoallergenic, it was possible to take a high volume. Table 1 shows the sensory evaluation results of the scent.
  • Example 5 Raw pepper used raw material: Aji Dulce (capsicum with suppressed p-AMT activity) was crossed with Capsicum chinense spicy cultivar Boot Jolokia (purchased from Tongarashi Yodogawa Co., Ltd.), cultivar selected over two generations And varieties that have mutations in p-AMT and are almost unable to synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same procedure as in Example 4 was performed. Preparation of pulverized vegetable product containing flavor: The same method as in Example 4 was used. The results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows.
  • Example 6 Raw pepper ⁇ Examples of breeding and aroma sensory test of the present invention pepper> Ingredients: Aji Dulce (capsicum with suppressed p-AMT activity) was crossed with Capsicum chinense spicy varieties Habanero (purchased from Tongarashi Yodogawa) and selected for two generations. Varieties that have almost no capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same procedure as in Example 4 was performed. Preparation of pulverized vegetable product containing flavor: The same method as in Example 4 was used. The results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows.
  • Example 7 Raw material used for freeze-dried red pepper: Capsicum annuum species CH-19 sweetness (p-AMT activity was suppressed) to the infinity-type pepper (capsicum with suppressed p-AMT activity) bred in Example 1 A cultivar selected from two generations, crossed with capsicum, non-patent document 3), mutated in p-AMT, an interspecies hybrid of Capsicum chinense and Capsicum annuum, and hardly capable of synthesizing capsaicinoid. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same method as in Example 1 was used.
  • Example 8 Raw material used for freeze-dried red pepper: Boot Jorokia red pepper bred in Example 2 (capsicum with suppressed p-AMT activity) and Capsicum annuum species CH-19 sweet (inhibited p-AMT activity) Cultivar, non-patent document 3) crossed over two generations, varieties of p-AMT, varieties of capsicum chinense species and capsicum annuum species, and varieties that hardly synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same method as in Example 1 was used. Preparation of pulverized vegetable product containing flavor: The same method as in Example 1 was used.
  • the capsaicinoid content of the obtained product was 0.03 mg / g (0.003 g / 100 g), and was confirmed to be 0.003 g / 100 g or less.
  • the capsinoid content measured at the same time was 2.5 mg / g.
  • the results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows.
  • Example 9 Raw material to be used for freeze-dried pepper: Crossing the Infinity pepper bred in Example 1 (capsicum with p-AMT activity suppressed), Capsicum baccatum species Aji Franco (purchased from Tongarashi Yodogawa) Variety selected over two generations, with a mutation in p-AMT, a variety between capsicum chinense and capsicum baccatum, which cannot synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same method as in Example 1 was used. Preparation of pulverized vegetable product containing flavor: The same method as in Example 1 was used.
  • the capsaicinoid content of the obtained product was 0.01 mg / g (0.001 g / 100 g), and was confirmed to be 0.003 g / 100 g or less.
  • the capsinoid content measured at the same time was 1.1 mg / g.
  • the results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows.
  • Example 10 Raw material to be used for freeze-dried pepper: Crossing the Infiniti peppers cultivated in Example 1 (capsicum with suppressed p-AMT activity), Capsicum baccatum seed kaleidoscope (purchased from Tongarashi Yodogawa), 2 A variety that has been selected over generations, has a mutation in p-AMT, and is an interspecific hybrid of Capsicum chinense and Capsicum baccatum, which cannot synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same method as in Example 1 was used. Preparation of pulverized vegetable product containing flavor: The same method as in Example 1 was used.
  • the capsaicinoid content of the obtained product was 0.02 mg / g (0.002 g / 100 g), and was confirmed to be 0.003 g / 100 g or less.
  • the capsinoid content measured at the same time was 1.8 mg / g.
  • the results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows.
  • Example 11 Raw material used for freeze-dried red pepper: Boot Joloquia red pepper bred in Example 2 (capsicum with suppressed p-AMT activity) is crossed with Capsicum baccatum spp. Variety selected over two generations, with a mutation in p-AMT, a variety between capsicum chinense and capsicum baccatum, which cannot synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same method as in Example 1 was used. Preparation of pulverized vegetable product containing flavor: The same method as in Example 1 was used.
  • the capsaicinoid content of the obtained product was 0.03 mg / g (0.003 g / 100 g), and was confirmed to be 0.003 g / 100 g or less.
  • the capsinoid content measured at the same time was 1.2 mg / g.
  • the results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows.
  • Example 12 Raw material used for freeze-dried capsicum: Boot Jolokia capsicum cultivated in Example 2 (capsicum with suppressed p-AMT activity) was crossed with Capsicum baccatum seed kaleidoscope (purchased from Tongarashi Yodogawa) A variety that has been selected over two generations, has a mutation in p-AMT, is an interspecific hybrid of Capsicum chinense and Capsicum baccatum, and can hardly synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same method as in Example 1 was used. Preparation of pulverized vegetable product containing flavor: The same method as in Example 1 was used.
  • the capsaicinoid content of the obtained product was 0.01 mg / g (0.001 g / 100 g), and was confirmed to be 0.003 g / 100 g or less.
  • the capsinoid content measured at the same time was 1.9 mg / g.
  • the results of sensory evaluation when 1 mg, 10 mg, and 100 mg of this ground sample were ingested are as follows.
  • p-AMT (+ / +) Pepper with both p-AMT enzyme genes in diploid pepper. The biosynthetic pathway for vanillylamine is not inhibited.
  • p-AMT (-/-) Pepper with mutated both p-AMT enzyme genes in diploid pepper. The biosynthesis pathway of vanillylamine is suppressed.
  • Raw pepper and fresh cream ingredients Infinity varieties selected in Example 1 that have a mutation in p-AMT and hardly synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials.
  • Raw material preparation The collected pepper was stored frozen.
  • Comparative Example 9 Raw pepper and fresh cream ingredients: Infinity of Comparative Example 1 was used. Fruits that were fully matured and turned red were harvested and used as raw materials. Raw material preparation: The collected pepper was stored frozen. Preparation of ground vegetable products containing flavors: Raw material used: Performed in the same manner as in Example 13. Preparation of vegetable pulverized product containing flavor: The same method as in Example 13 was used. 0.1 g of this crushed sample was added to 25 g of fresh cream (Seven Premium Hokkaido Pure Fresh Cream), mixed, and it was “pungent” 6 according to the sensory evaluation when 0.5 g was ingested. Therefore, sensory evaluation was stopped. Infinity seeds were intensely irritating and difficult to add to food. The sensory test results of scent are shown in Table 2.
  • Example 14 Raw Capsicum + Raw Cream Use Raw Material: A boot Jorokia variety selected in Example 2 that has a mutation in p-AMT and hardly synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same procedure as in Example 13 was performed. Preparation of vegetable pulverized product containing flavor: The same method as in Example 13 was used. The result of sensory evaluation when 0.1 g or 1 g of this ground sample is added to and mixed with 25 g of fresh cream (Seven Premium; Hokkaido Pure Fresh Cream) and 5 g is ingested is as follows.
  • Example 15 Raw pepper and raw cream ingredients: Infinity varieties selected in Example 1 that have a mutation in p-AMT and hardly synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same procedure as in Example 13 was performed. Preparation of extract containing flavor: For the preparation, first, the pepper was pulverized with Milcer 800DG (Iwatani Corporation), 10 g of ethanol was added per 1 g of pepper, and allowed to stand at room temperature for 5 days. The results of sensory evaluation when 0.25 g of this ethanol extracted sample was added to and mixed with 25 g of fresh cream (Seven Premium; Hokkaido Pure Fresh Cream) and 5 g were ingested are as follows.
  • Example 16 Raw pepper and fresh cream ingredients: Boot Jolocia variety selected in Example 2 that has a mutation in p-AMT and hardly synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same procedure as in Example 13 was performed. Preparation of extract containing flavor: For the preparation, first, the pepper was pulverized with Milcer 800DG (Iwatani Corporation), 10 g of ethanol was added per 1 g of pepper, and allowed to stand at room temperature for 5 days.
  • Milcer 800DG Milcer 800DG
  • Example 17 and 18, Comparative Examples 12 to 17 Aji Dulce (capsicum with suppressed p-AMT activity) was crossed with Capsicum chinense pepper cultivar Infinity (purchased from Tongarashi Yodogawa Co., Ltd.) and selected for two generations. A variety that can hardly synthesize capsaicinoids.
  • GC / MS analysis was performed, and total ions of the entire chromatogram were calculated by integrating the ion range of 35 to 1000 and 5 to 30 minutes after injection.
  • GC / MS analysis of the Infinity species was performed under the same conditions (Comparative Example 12). Table 3 and FIG. 2 show the results of GC-MS analysis of
  • Aji Dulce (capsicum with suppressed p-AMT activity) was crossed with Capsicum chinense hot pepper cultivar Boot Jolokia (purchased from Tongarashi Yodogawa Co., Ltd.), and varieties selected for two generations had mutations in p-AMT However, it is a variety that can hardly synthesize capsaicinoids.
  • ester compounds (E) -8-methyl-6-nonenoic acid 1-hexanol ester (8EH), 8-methylnonanoic acid 1-hexanol ester (8EH) identified by comparing retention times and fragment ions with the standard flavor product synthesized 8MH), 7-methyloctanoic acid 1-hexanol ester (7MH), (E) -8-methyl-6-nonenoic acid 1-pentanol ester (8EP), 8-methylnonanoic acid 1-pentanol ester (8MP), The characteristic ion peak areas of 7-methyloctanoic acid 1-pentanol ester (7MP), vanillyl n-valerate (VV), and vanillyl pivalic acid ester (VP) were compared, and the content was calculated.
  • Example 18 Detected (Example 18).
  • a GC / MS analysis of the boot Jorokia species was performed under the same conditions (Comparative Example 13). Separately, the common Capsicum annuum varieties George Long (Tongarashi Yodogawa) and paprika (Ito-Yokado), which have normal p-AMT under the same conditions, and the existing varieties of Capsicum chinense varieties with mutations in p-AMT.
  • GC / MS analysis of CH19 sweet which is a certain Aji Dulce and Capsicum annuum variety was performed (Comparative Examples 14, 15, 16, and 17), respectively.
  • Table 3 and FIGS. 3 and 4 show the results of GC-MS analysis in red pepper.
  • Non-patent document 7 shows that capsicum varieties having a fruity fragrance have a high total ion content by GC / MS).
  • the cultivar (p-AMT ( ⁇ / ⁇ )) in which p-AMT is suppressed at many peaks other than capsaicinoid is the original p-AMT (+ / +) It was shown that the peak area was high compared to the variety.
  • the ester flavor was shown to be 2 to 20 times higher than in Comparative Examples 12 and 13. Therefore, by crossing p-AMT-suppressed varieties to obtain p-AMT-suppressed varieties, there are few capsaicinoids, which are strong pungent compounds, and flavors consisting of volatile compounds, particularly ester compounds, that are the source of a fruity scent. As a result, it was possible to obtain a red pepper containing so much that it surpassed the original species of red pepper. Moreover, since the GC / MS peak was small in Comparative Examples 14, 15, 16, and 17 and the total number of ions was low, it was shown that the existing varieties had less flavor than the examples.
  • Example 19 to 48 Comparative Examples 18 and 19
  • Aji Dulce capsicum with suppressed p-AMT activity
  • Capsicum chinense spicy cultivar Infinity purchased from Tongarashi Yodogawa
  • Boot Jolokia purchased from Tongarashi Yodogawa
  • Fruits were harvested and used as raw materials. After freezing and pulverizing, 1 ml of hexane was added per 0.1 g of sample, the sample tube was sealed, and after extraction for 24 hours at room temperature, 1 ⁇ L of this extract was subjected to analysis.
  • p-AMT (-/-) varieties bred from capsaicin-rich strains contain 0.01 mg / g or more of vanillyl pivalate (VP). It was suggested that it is a pepper having an excellent flavor compared with the control product and the existing pepper. Pepper with less pungency and its processed product that improves the taste and flavor by increasing the content by suppressing p-AMT of hot pepper as well as confirming the content of VP as a fruity ester flavor for the first time was found to be manufacturable.
  • Examples 49 to 54 Raw material used for freeze-dried capsicum: Aji Dulce (purchased from Sunoyayasai, capsicum with suppressed p-AMT activity) Capsicum chinense spicy cultivar Infinity (purchased from Tongarashi Sasagawa) or boot A variety that crosses Jorokia (purchased from Tongarashi Yodogawa Co., Ltd.) and has been selected for two generations, has a mutation in p-AMT, and cannot synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials: The same method as in Example 1 was used. Preparation of an ethanol mixture containing flavor: the same procedure as in Example 1.
  • Examples 55 and 56 Fresh peppers The same boot Joloquia p-AMT (-/-) variety 0011-0301-01x01Nx03N-1 as Example 49, Infinity p-AMT same as Example 53 (- /-) Using varieties 0041-0601-02x01Nx01x02N-2, 10 g of 99.5% ethanol per gram was added, and allowed to stand at room temperature for 3 days. Vanillyl alcohol, vanillyl ethyl ether, capsaicinoid in the liquid The amount of capsinoid was measured. It was confirmed that the capsaicinoid and capsinoid content of the pepper was 0.01 mg / g (0.001 g / 100 g) or less for all samples.
  • vanillyl alcohol measured simultaneously was 0.92 mg / g and 0.84 mg / g, respectively.
  • vanillyl ethyl alcohol was 0.21 mg / g and 0.15 mg / g, respectively.
  • the p-AMT-suppressed varieties contain almost no capsaicinoids and are hypoallergenic.
  • the addition of alcohol produces vanillyl alcohol and vanillyl ethyl ether. A sweet, long brewed scent like vanilla beans.
  • the pepper was pulverized with Milcer 800DG (Iwatani Corporation).
  • the capsinoid content of the obtained product was 17.2 mg / g.
  • the capsaicinoid content was 0.03 mg / g (0.003 g / 100 g), and even when the powder was directly consumed, it did not feel almost pungent.
  • This ground sample was weighed into a 10 mg tube, and water (Example 61), methanol (Pure Chemical 73125-1230) (Example 62), ethanol (Pure Chemical 17065-1230) (Example 63), 1-propanol ( Wako Pure Chemical Industries, Ltd.
  • Example 64 1 mL of 1-butanol (Pure Chemical 63130-0380) (Example 65) was added, and then 0.002 mL of 6M sodium hydroxide solution was added. The reaction was allowed to proceed for 1 hour at room temperature. Table 6 shows the flavor substance content and the pH after reaction for 1 hour after the addition of sodium hydroxide. Capsinoids contained in red pepper reacted rapidly to form vanillyl alcohol, vanillyl methyl ether, vanillyl ethyl ether, vanillyl propyl ether, and vanillyl butyl ether, respectively. The vanilla-like sweet scent was enhanced.
  • the capsinoid content of the obtained product was 16.6 mg / g.
  • the capsaicinoid content was 0.01 mg / g (0.001 g / 100 g), and even when the powder was eaten directly, almost no pungency was felt.
  • the ground sample was weighed into a 10 mg tube, and water (Example 66), methanol (Example 67), ethanol (Example 68), 1-propanol (Example 69), and 1-butanol (Example 70) were respectively obtained. 1 mL was added, and then 0.002 mL of 6M sodium hydroxide solution was added and reacted at room temperature for 1 hour.
  • Table 6 shows the flavor substance content and the pH after reaction for 1 hour after the addition of sodium hydroxide.
  • Capsinoids contained in red pepper reacted rapidly to form vanillyl alcohol, vanillyl methyl ether, vanillyl ethyl ether, vanillyl propyl ether, and vanillyl butyl ether, respectively.
  • the vanilla-like sweet scent was enhanced.
  • Example 71 Genetic of flavor substance from ground pepper of the present invention> A raw material Aji Dulce (capsicum with reduced p-AMT activity) was crossed with Capsicum chinense hot pepper cultivar Boot Jolokia (purchased from Tongarashi Yodogawa) and selected for two generations and mutated to p-AMT It is a variety that has almost no capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw material The collected pepper was freeze-dried with a freeze dryer (FD-1000 manufactured by Tokyo Rika Kikai Co., Ltd.) for 2 days.
  • FD-1000 freeze dryer manufactured by Tokyo Rika Kikai Co., Ltd.
  • the pepper was pulverized with Milcer 800DG (Iwatani Corporation).
  • the capsinoid content of the obtained product was 17.2 mg / g.
  • the capsaicinoid content was 0.03 mg / g (0.003 g / 100 g), and even when the powder was directly consumed, it did not feel almost pungent.
  • the ground sample was weighed into a 100 mg tube, 10 mL of ethanol was added, and then 0.002 mL of 6M sodium hydroxide solution was added and allowed to react at room temperature for 1 hour.
  • the capsinoid contained in the pepper reacted rapidly, yielding 8.9 mg / g vanillyl ethyl ether per dried pepper.
  • the vanilla-like sweet scent was enhanced.
  • Example 72 to 75 ⁇ Conjugation of flavor substance from ground pepper of the present invention with cyclodextrin> A raw material Aji Dulce (capsicum with reduced p-AMT activity) was crossed with Capsicum chinense hot pepper cultivar Boot Jolokia (purchased from Tongarashi Yodogawa) and selected for two generations and mutated to p-AMT A variety that has almost no capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials Cyclodextrins (Nippon Food Chemical Co., Ltd.
  • Example 75 A dry sample without cyclodextrin was also prepared in the same manner (Example 75).
  • Preparation of vegetable pulverized product The freeze-dried pulverized sample obtained was stored at room temperature for 30 days, then weighed into a 20 mg tube, added with 1 mL of pure water, suspended, contained in the mouth, and the degree of fruity scent by two panels Evaluation was made by a sensory test. The evaluation was performed according to the same criteria as in Example 1 (7-level evaluation from very weak (0) to very strong (6)). All samples had a fruity scent, but the samples to which each cyclodextrin was added maintained a stronger scent. In particular, ⁇ cyclodextrin and ⁇ cyclodextrin strongly maintained the fragrance (Table 7).
  • Example 76 to 79 ⁇ Conjugation of flavor substance from ground pepper of the present invention with cyclodextrin> Used raw material Aji Dulce (capsicum with reduced p-AMT activity) was crossed with Capsicum chinense spicy pepper cultivar Infiniti (purchased from Tongarashi Yodogawa) and selected for two generations, with mutations in p-AMT However, it is a variety that can hardly synthesize capsaicinoids. Fruits that were fully matured and turned red were harvested and used as raw materials. Preparation of raw materials Cyclodextrin (Nippon Food Chemicals Co., Ltd.
  • the present invention can provide a capsicum plant and a composition thereof capable of maximally and widely using the “fragrance”, “flavor”, and “other flavor” inherent to the capsicum, excluding “pungency”.

Abstract

L'invention concerne une plante de Capsicum qui permet une utilisation large et maximale de l'arôme, du goût, etc. inhérents à Capsicum annuum, sans le caractère épicé. Le fruit de ladite plante de Capsicum contient au moins un composé (défini dans la description) qui est représenté par la formule (I) (à l'exclusion des capsinoïdes). La plante de Capsicum a une teneur en capsaïcinoïde ne dépassant pas 1 mg pour 1 g de fruit sec.
PCT/JP2019/009049 2018-03-23 2019-03-07 Plante de capsicum aromatique WO2019181529A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114051924A (zh) * 2021-12-08 2022-02-18 金华市农业科学研究院(浙江省农业机械研究院) 一种降糖辣椒的选育方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004100942A1 (fr) * 2003-05-15 2004-11-25 Ajinomoto Co., Inc. Composition permettant de reduire le taux de lipides corporels
WO2007021020A1 (fr) * 2005-08-16 2007-02-22 Ajinomoto Co., Inc. Composition contenant un capsinoïde
WO2012086811A1 (fr) * 2010-12-22 2012-06-28 味の素株式会社 Suppresseur d'absorption d'aliments et agent anti-obésité
WO2016153011A1 (fr) * 2015-03-25 2016-09-29 高砂香料工業株式会社 Dérivé méthylé de menthol et composition d'agent de refroidissement le contenant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004100942A1 (fr) * 2003-05-15 2004-11-25 Ajinomoto Co., Inc. Composition permettant de reduire le taux de lipides corporels
WO2007021020A1 (fr) * 2005-08-16 2007-02-22 Ajinomoto Co., Inc. Composition contenant un capsinoïde
WO2012086811A1 (fr) * 2010-12-22 2012-06-28 味の素株式会社 Suppresseur d'absorption d'aliments et agent anti-obésité
WO2016153011A1 (fr) * 2015-03-25 2016-09-29 高砂香料工業株式会社 Dérivé méthylé de menthol et composition d'agent de refroidissement le contenant

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
SUTOH K. ET AL.: "Stability of capsinoid in various solvents", J. AGRIC. FOOD CHEM., vol. 49, 2001, pages 4026 - 4030, XP002388561, ISSN: 0021-8561, doi:10.1021/jf0103424 *
TANAKA Y. ET AL.: "Assessment of capsiconinoid composition, nonpungent capsaicinoid analogues, in Capsicum cultivars", J. AGRIC. FOOD CHEM., vol. 57, 2009, pages 5407 - 5412, XP055637516, ISSN: 0021-8561 *
TANAKA Y. ET AL.: "Multiple loss-of-function putative aminotransferase alleles contribute to low pungency and capsinoid biosynthesis in Capsicum chinense", MOL. BREEDING, vol. 35, no. 142, 2015, pages 1 - 13, XP055637515, ISSN: 1380-3743 *
TANAKA YOSHIYUKI ET AL: "research on capsiconinoid contents nonpungent capsaicinoid analogues in capsicum cultivars", SCIENTIFIC REPORT OF THE FACULTY OF AGRICULTURE, vol. 103, 2014 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114051924A (zh) * 2021-12-08 2022-02-18 金华市农业科学研究院(浙江省农业机械研究院) 一种降糖辣椒的选育方法

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