JP6501267B2 - 食品の褐変化抑制剤 - Google Patents
食品の褐変化抑制剤 Download PDFInfo
- Publication number
- JP6501267B2 JP6501267B2 JP2016131996A JP2016131996A JP6501267B2 JP 6501267 B2 JP6501267 B2 JP 6501267B2 JP 2016131996 A JP2016131996 A JP 2016131996A JP 2016131996 A JP2016131996 A JP 2016131996A JP 6501267 B2 JP6501267 B2 JP 6501267B2
- Authority
- JP
- Japan
- Prior art keywords
- miso
- browning
- peak
- ethanol extract
- roasted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 235000013305 food Nutrition 0.000 title claims description 35
- 239000003112 inhibitor Substances 0.000 title claims description 22
- 244000294411 Mirabilis expansa Species 0.000 claims description 102
- 235000015429 Mirabilis expansa Nutrition 0.000 claims description 102
- 235000013536 miso Nutrition 0.000 claims description 102
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- 239000000469 ethanolic extract Substances 0.000 claims description 40
- 239000004480 active ingredient Substances 0.000 claims description 11
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 claims description 10
- 238000001694 spray drying Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229930003935 flavonoid Natural products 0.000 claims description 8
- 235000017173 flavonoids Nutrition 0.000 claims description 8
- 150000002215 flavonoids Chemical class 0.000 claims description 8
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 claims description 8
- 235000006539 genistein Nutrition 0.000 claims description 8
- 229940045109 genistein Drugs 0.000 claims description 8
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 235000007240 daidzein Nutrition 0.000 claims description 5
- 238000004949 mass spectrometry Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 235000013555 soy sauce Nutrition 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 12
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 10
- 239000004471 Glycine Substances 0.000 description 10
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 10
- 239000000284 extract Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000001641 gel filtration chromatography Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 102000007327 Protamines Human genes 0.000 description 6
- 108010007568 Protamines Proteins 0.000 description 6
- 238000000944 Soxhlet extraction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000008363 phosphate buffer Substances 0.000 description 6
- 229940048914 protamine Drugs 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000010828 elution Methods 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 241001070941 Castanea Species 0.000 description 4
- 235000014036 Castanea Nutrition 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000002683 reaction inhibitor Substances 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000002292 Radical scavenging effect Effects 0.000 description 2
- 244000273928 Zingiber officinale Species 0.000 description 2
- 235000006886 Zingiber officinale Nutrition 0.000 description 2
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012156 elution solvent Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 235000008397 ginger Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000013379 molasses Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZIIIHCDYNKIMOD-UJPDDDSFSA-N 2-aminoacetic acid;(2r,3s,4r)-2,3,4,5-tetrahydroxypentanal Chemical compound NCC(O)=O.OC[C@@H](O)[C@H](O)[C@@H](O)C=O ZIIIHCDYNKIMOD-UJPDDDSFSA-N 0.000 description 1
- 241000193738 Bacillus anthracis Species 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 244000195452 Wasabia japonica Species 0.000 description 1
- 235000000760 Wasabia japonica Nutrition 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000012019 baked potatoes Nutrition 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000002481 ethanol extraction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940038487 grape extract Drugs 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000009923 sugaring Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Landscapes
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- General Preparation And Processing Of Foods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015133211 | 2015-07-02 | ||
| JP2015133211 | 2015-07-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017012168A JP2017012168A (ja) | 2017-01-19 |
| JP2017012168A5 JP2017012168A5 (enExample) | 2017-08-03 |
| JP6501267B2 true JP6501267B2 (ja) | 2019-04-17 |
Family
ID=57827414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016131996A Active JP6501267B2 (ja) | 2015-07-02 | 2016-07-01 | 食品の褐変化抑制剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP6501267B2 (enExample) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01289446A (ja) * | 1988-05-13 | 1989-11-21 | Toyo Seikan Kaisha Ltd | フラボノイド添加密封容器入り録茶飲料 |
| JP2997303B2 (ja) * | 1990-08-19 | 2000-01-11 | 三栄源エフ・エフ・アイ株式会社 | 褐変防止剤 |
| JP2677487B2 (ja) * | 1992-06-26 | 1997-11-17 | 日本水産株式会社 | 緑色野菜の変色防止方法 |
| JP2000093132A (ja) * | 1998-09-22 | 2000-04-04 | Akira Shirota | 大豆発酵食品、大豆発酵茶およびこれらの製造方法 |
| JP2006265249A (ja) * | 2005-02-22 | 2006-10-05 | Tokyo Univ Of Agriculture | 新規フラボノイド化合物及びその製造方法並びにそれを有効成分とする抗酸化剤 |
| JP4897229B2 (ja) * | 2005-03-15 | 2012-03-14 | 学校法人 関西大学 | メイラード反応阻害剤 |
| US20080317692A1 (en) * | 2007-06-25 | 2008-12-25 | Te-Sheng Chang | Suicide substrates of tyrosinase and use thereof |
| JP5713571B2 (ja) * | 2010-03-02 | 2015-05-07 | ヒガシマル醤油株式会社 | メイラード反応阻害剤およびＡＧＥｓ生成抑制剤 |
| JP6131164B2 (ja) * | 2013-10-07 | 2017-05-17 | マルコメ株式会社 | Ｐｐａｒ活性化剤およびその組成物 |
-
2016
- 2016-07-01 JP JP2016131996A patent/JP6501267B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017012168A (ja) | 2017-01-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Karamać et al. | Phenolic contents and antioxidant capacities of wild and cultivated white lupin (Lupinus albus L.) seeds | |
| Naczk et al. | Extraction and analysis of phenolics in food | |
| Ryan et al. | Critical Review. Phenolic compounds in olives | |
| Lee et al. | Determination of chokeberry (Aronia melanocarpa) polyphenol components using liquid chromatography–tandem mass spectrometry: Overall contribution to antioxidant activity | |
| Souza et al. | Isolation of gallic acid, caffeine and flavonols from black tea by on-line coupling of pressurized liquid extraction with an adsorbent for the production of functional bakery products | |
| Egydio et al. | Supercritical fluid extraction of lycopene from tomato juice and characterization of its antioxidation activity | |
| Gómez-Mejía et al. | Determination of phenolic compounds in residual brewing yeast using matrix solid-phase dispersion extraction assisted by titanium dioxide nanoparticles | |
| Ha et al. | Changes occurring in nutritional components (phytochemicals and free amino acid) of raw and sprouted seeds of white and black sesame (Sesamum indicum L.) and screening of their antioxidant activities | |
| Račkauskienė et al. | Effects of beetroot (Beta vulgaris) preparations on the Maillard reaction products in milk and meat-protein model systems | |
| Ahmad et al. | The effect of extraction methods of Bawang Dayak (Eleutherine palmifolia L. MERR) against TLC profiles and sunscreen activities | |
| Rungruang et al. | Antioxidant and anti-aging enzyme activities of bioactive compounds isolated from selected Zingiberaceae plants | |
| Kim et al. | Antioxidant and phytoestrogenic activities of puffed black soybeans (Glycine max) | |
| Coghe et al. | Effect of non-enzymatic browning on flavour, colour and antioxidative activity of dark specialty malts—A review | |
| Qiu et al. | Antioxidant and antigenotoxic activities of ethanol extracts from Rhus chinensis Mill leaves | |
| JP6501267B2 (ja) | 食品の褐変化抑制剤 | |
| Li et al. | Polyphenol profiles and antioxidant properties of ethanol extracts from Osmanthus fragrans (Thunb.) Lour. flowers | |
| KR102400713B1 (ko) | 유색밀 배유 염색방법 | |
| Agatonovic-Kustrin et al. | Determination of free phenolic acids in plant-derived foods by high-performance thin-layer chromatography with direct 2, 2′-diphenyl-1-picrylhydrazyl assay | |
| Ferysiuk et al. | The spectrophotometric analysis of antioxidant properties of selected herbs in VISION-PRO™ UV-VIS | |
| Long et al. | Novel pink pigments produced by thermal interaction of theaflavins, theanine, and glucose: Color formation, isolation, and structural characterization | |
| Kao et al. | Carotenoid composition in Rhinacanthus nasutus (L.) Kurz as determined by HPLC-MS and affected by freeze-drying and hot-air-drying | |
| JP2007517528A (ja) | 長生紅ドラジの調製方法とこの調製方法により調製された長生紅ドラジ及びそれを含む機能性食品素材 | |
| ABD-ALLA et al. | Comparative phytochemical and biological investigation of five Glycine max (L.) Merrill genotypes | |
| Tomar et al. | Comparative evaluation on phenolic content and antioxidant activity of legume sprouts as affected by various solvents for application in livestock products | |
| Lembong et al. | Antioxidant properties of cocoa (Theobroma cocoa L.) shell powder in fermentation and immersion treatments. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170620 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170620 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20170620 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170911 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20180427 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180508 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180709 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180904 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20181031 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190305 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190313 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 6501267 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |