JP2016023174A - Functional agent with maillard reaction inhibiting function or antioxidative function - Google Patents
Functional agent with maillard reaction inhibiting function or antioxidative function Download PDFInfo
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- JP2016023174A JP2016023174A JP2014150454A JP2014150454A JP2016023174A JP 2016023174 A JP2016023174 A JP 2016023174A JP 2014150454 A JP2014150454 A JP 2014150454A JP 2014150454 A JP2014150454 A JP 2014150454A JP 2016023174 A JP2016023174 A JP 2016023174A
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- glucuronide
- functional agent
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- dry distillation
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- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 49
- 238000006243 chemical reaction Methods 0.000 title claims description 22
- 230000002401 inhibitory effect Effects 0.000 title claims description 20
- 238000000197 pyrolysis Methods 0.000 claims abstract description 29
- DUBCCGAQYVUYEU-UHFFFAOYSA-N Querciturone Natural products O1C(C(O)=O)C(O)C(O)C(O)C1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O DUBCCGAQYVUYEU-UHFFFAOYSA-N 0.000 claims abstract description 25
- DUBCCGAQYVUYEU-ZUGPOPFOSA-N miquelianin Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O DUBCCGAQYVUYEU-ZUGPOPFOSA-N 0.000 claims abstract description 25
- LOJXBHNAFUDMIQ-UHFFFAOYSA-N quercetin-3-alpha-glucuronide Natural products OC1OC(C(O)C(O)C1O)C(=O)Oc1c(oc2cc(O)cc(O)c2c1=O)-c1ccc(O)c(O)c1 LOJXBHNAFUDMIQ-UHFFFAOYSA-N 0.000 claims abstract description 25
- DUBCCGAQYVUYEU-GGTBVAQXSA-N quercetin-3-glucuronide Natural products O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O DUBCCGAQYVUYEU-GGTBVAQXSA-N 0.000 claims abstract description 25
- 239000000284 extract Substances 0.000 claims abstract description 23
- FNTJVYCFNVUBOL-ZUGPOPFOSA-N kaempferol 3-O-glucuronide Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=C(C=2C=CC(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O FNTJVYCFNVUBOL-ZUGPOPFOSA-N 0.000 claims abstract description 21
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 239000004480 active ingredient Substances 0.000 claims abstract description 11
- 239000002683 reaction inhibitor Substances 0.000 claims abstract description 7
- 244000144730 Amygdalus persica Species 0.000 claims description 36
- 235000006040 Prunus persica var persica Nutrition 0.000 claims description 36
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 34
- 238000005292 vacuum distillation Methods 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 241000196324 Embryophyta Species 0.000 claims description 12
- AYEKKSTZQYEZPU-RYUDHWBXSA-N pentosidine Chemical group OC(=O)[C@@H](N)CCCCN1C=CC=C2N=C(NCCC[C@H](N)C(O)=O)N=C12 AYEKKSTZQYEZPU-RYUDHWBXSA-N 0.000 claims description 9
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- 239000000463 material Substances 0.000 claims description 6
- 238000003763 carbonization Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 3
- 230000007246 mechanism Effects 0.000 claims description 3
- 230000009471 action Effects 0.000 abstract description 5
- 235000013411 Alpinia speciosa Nutrition 0.000 abstract 2
- 244000041517 Etlingera elatior Species 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 28
- 235000006708 antioxidants Nutrition 0.000 description 17
- 230000005764 inhibitory process Effects 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 229940087168 alpha tocopherol Drugs 0.000 description 14
- 229960000984 tocofersolan Drugs 0.000 description 14
- 239000002076 α-tocopherol Substances 0.000 description 14
- 235000004835 α-tocopherol Nutrition 0.000 description 14
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 239000000341 volatile oil Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- 229930182480 glucuronide Natural products 0.000 description 7
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 6
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 235000005875 quercetin Nutrition 0.000 description 6
- 229960001285 quercetin Drugs 0.000 description 6
- UBDZFAGVPPMTIT-UHFFFAOYSA-N 2-aminoguanidine;hydron;chloride Chemical compound [Cl-].NC(N)=N[NH3+] UBDZFAGVPPMTIT-UHFFFAOYSA-N 0.000 description 5
- 239000002537 cosmetic Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- -1 glucuronide glucuronide Chemical class 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 3
- 229940097043 glucuronic acid Drugs 0.000 description 3
- 150000008134 glucuronides Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000013641 positive control Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- WRYLYDPHFGVWKC-UHFFFAOYSA-N 4-terpineol Chemical compound CC(C)C1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-UHFFFAOYSA-N 0.000 description 2
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 2
- 244000273928 Zingiber officinale Species 0.000 description 2
- 235000006886 Zingiber officinale Nutrition 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229930003944 flavone Natural products 0.000 description 2
- 150000002212 flavone derivatives Chemical class 0.000 description 2
- 235000011949 flavones Nutrition 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 235000008397 ginger Nutrition 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 2
- OCZVHBZNPVABKX-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine;ethanol Chemical compound CCO.[O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 OCZVHBZNPVABKX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WRYLYDPHFGVWKC-SNVBAGLBSA-N 4-Terpineol Natural products CC(C)[C@]1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-SNVBAGLBSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 1
- 244000141009 Hypericum perforatum Species 0.000 description 1
- 235000017309 Hypericum perforatum Nutrition 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 206010072810 Vascular wall hypertrophy Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 239000013566 allergen Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 210000004958 brain cell Anatomy 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002481 ethanol extraction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000008810 intracellular oxidative stress Effects 0.000 description 1
- 235000008777 kaempferol Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
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- 238000011084 recovery Methods 0.000 description 1
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- 239000002453 shampoo Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- General Preparation And Processing Of Foods (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
本発明は、ショウガ科の植物である「月桃」の「葉部」から分離取得した特定の成分を有効成分とする「メイラード反応抑制機能または／および抗酸化機能を有する機能剤」（すなわち「メイラード反応抑制剤または／および抗酸化剤」）に関するものである。 The present invention relates to a “functional agent having a Maillard reaction inhibitory function and / or an antioxidant function” (ie, “a functional agent having a function of inhibiting Maillard reaction”), which comprises a specific component separated and obtained from the “leaf” of “Ginger” which is a plant of the family Ginger. Maillard reaction inhibitor or / and antioxidant ").
[月桃について]
月桃は、ショウガ科ハナミョウガ属の多年草であり、我が国においては、主として琉球諸島（沖縄諸島や奄美諸島）や九州南部において、民家の庭先でもよく見かけるなじみの植物である。成長した月桃の高さはたとえば３ｍにも達し、葉の長さは４０〜６０ｃｍ程度、葉の巾は１５ｃｍ程度である。
月桃の葉（月桃葉）に含まれる成分には、防虫、防カビ、抗菌、消臭、鎮静作用などの作用があることも知られている。
[About moon peach]
Tsuki-Peach is a perennial plant belonging to the genus Glyceraceae, and in Japan, it is a familiar plant often found in the gardens of private houses mainly in the Ryukyu Islands (Okinawa Islands and Amami Islands) and southern Kyushu. The height of the grown moon peach reaches, for example, 3 m, the leaf length is about 40 to 60 cm, and the leaf width is about 15 cm.
It is also known that the ingredients contained in moon peach leaves (moon peach leaves) have effects such as insect repellent, fungicidal, antibacterial, deodorant, and sedative effects.
[その１]
「月桃の蒸留液」については、次のような文献がある。
[Part 1]
The following documents are available for “moon peach distillate”.
（特許文献１）
−１−
特開２００２−３２２０２３（特許文献１）の請求項１には、「月桃の地上部から、乾留法、減圧蒸留法、水蒸気蒸留法などの手法により月桃蒸留液を抽出した後、分液ロート又はオイルセパレーター等で精油分を分離除去し、残った成分をろ過して、化粧品などの製造に利用することを特徴とする月桃精油除去液の製造方法が示されている。この精油除去液の用途は、化粧水、美容液、脂肪酸クリーム、シャンプーなどである。
−２−
月桃を蒸留したときの蒸留液（留出液のこと）には精油分が含まれるので、通常であればその精油分を有効成分として利用するのであるが、この特許文献１の発明においては、蒸留液から精油分を除去した残りの液を利用するという逆の発想を採用している。
(Patent Document 1)
-1-
Claim 1 of Japanese Patent Application Laid-Open No. 2002-322023 (Patent Document 1) states that “After extracting the moon peach distillate from the above-ground part of moon peach by a method such as dry distillation, vacuum distillation, steam distillation, etc. There is shown a method for producing a moon peach essential oil removing liquid characterized in that essential oil is separated and removed with a funnel or oil separator, etc., and the remaining components are filtered and used for the production of cosmetics and the like. The use of the liquid is skin lotion, cosmetic liquid, fatty acid cream, shampoo and the like.
-2-
The distillate (distillate) obtained when distilling moon peach contains essential oils, so normally the essential oil is used as an active ingredient. However, in the invention of Patent Document 1, The reverse idea of using the remaining liquid after removing the essential oil from the distillate is adopted.
[その２]
「ケルセチン−３−Ｏ−グルクロニド」の記載のある文献
特許電子図書館による公報全文の検索において、「ケルセチン−３−Ｏ−グルクロニド」の記載のある文献は３件ある。
[Part 2]
Documents with description of “quercetin-3-O-glucuronide” In the search of the full text of the gazette by the patent electronic library, there are three documents with description of “quercetin-3-O-glucuronide”.
（特許文献２）
そのうちの１件の特開２００４−０１０４８８（特許文献２）はアレルゲンの腸管透過抑制剤にかかるものであって、その請求項６には香辛料からの抽出物であるケルセチン−３−Ｏ−グルクロニドにつき記載がある。
また、この文献の段落００１７にはケルセチン−３−Ｏ−グルクロニドの化学式が示されており、段落００４５にはこの化合物の１Ｈ−ＮＭＲ、１３Ｃ−ＮＭＲも示されている。
(Patent Document 2)
One of them, JP-A-2004-010488 (Patent Document 2) relates to an intestinal permeation inhibitor of allergen, and in claim 6, quercetin-3-O-glucuronide, which is an extract from spices, is disclosed. There is a description.
Also, paragraph 0017 of this document shows the chemical formula of quercetin-3-O-glucuronide, and paragraph 0045 also shows 1H-NMR and 13C-NMR of this compound.
[その３]
「ケルセチン、グルクロニド、抗酸化、メイラード」の記載のある文献
特許電子図書館による公報全文の検索において、「ケルセチン クエルセチン」×「グルクロニド グルクロナイド」×「抗酸化 メイラード」の検索式による検索によれば、たとえば次のような文献がある。
[Part 3]
Documents with description of `` quercetin, glucuronide, antioxidant, maillard '' In the search of the full text of the gazette by the electronic library, according to the search formula of `` quercetin quercetin '' x `` glucuronide glucuronide '' x `` antioxidant maillard '' The following documents are available.
（特許文献３）
特開２００９−１０６２６５（特許文献３）の段落０００７には、「抗酸化性の高いフラボンの７位グルクロン酸抱合体が蓄積している」旨の記載がある。
(Patent Document 3)
In paragraph 0007 of JP-A-2009-106265 (Patent Document 3), there is a description that “the 7-position glucuronide conjugate of flavone having high antioxidant property is accumulated”.
（特許文献４）
特開２００７−１０６６９６（特許文献４）の段落０００２には、「ケルセチン抱合体は抗酸化作用、抗炎症作用、脂質吸収抑制作用、脳細胞伝達物質の強化作用等を有することが知られている」旨の記載がある。
(Patent Document 4)
In paragraph 0002 of JP 2007-106696 (Patent Document 4), it is known that “the quercetin conjugate has an antioxidant action, an anti-inflammatory action, a lipid absorption inhibitory action, a brain cell transmission substance enhancing action, and the like. Is described.
（特許文献５）
特開２００１−１２２７９１（特許文献５）には、「ケルセチン−３−β−Ｄ−グルクロナイドのインビトロ研究は抗酸化および抗炎症性を有すること、および血小板凝縮およびヒアルニダーゼを阻止し、毛細血管透過性を減らすことにより浮腫を縮小することを示す」旨の記載がある。
(Patent Document 5)
JP 2001-122791 (Patent Document 5) states that “An in vitro study of quercetin-3-β-D-glucuronide has antioxidant and anti-inflammatory properties, and prevents platelet condensation and hyaluridase, and capillary permeability. Indicates that edema can be reduced by reducing ”.
（特許文献６）
再表２０１０／０８４８７９（特許文献６）には、「ケルセチンの３位グルクロン酸配糖体はミケリアンと呼ばれ、抗鬱剤として用いられるセントジョーンズワートの薬理種成分の一つとして知られており、・・・」、「ケルセチンの３位グルクロン酸配糖体は、ＬＤＬ分解阻害活性や、Ｈ２Ｏ２による細胞内酸化ストレスの軽減効果や、アンジオテンシンによる血管肥大の抑制効果等が知られている」旨の記載がある。
(Patent Document 6)
In Table 2010/084879 (Patent Document 6), “the 3-position glucuronic acid glycoside of quercetin is called Michelian and is known as one of the pharmacological species components of St. John's wort used as an antidepressant.・ ・ ”,“ Quercetin 3-position glucuronic acid glycoside is known to have LDL degradation inhibitory activity, an effect of reducing intracellular oxidative stress by H2O2, an angiotensin-suppressing effect of vascular hypertrophy, etc. ” There is.
[その４]
「ケンフェロール−３−Ｏ−グルクロニド」の記載のある文献
特許電子図書館による公報全文の検索において、「ケンフェロール−３−Ｏ−グルクロニド」の記載のある文献はヒットしなかった。
（従って、「ケルセチン−３−Ｏ−グルクロニド」と「ケンフェロール−３−Ｏ−グルクロニド」との双方について記載のある文献もヒットしなかった。）
[Part 4]
Documents with description of “Kempferol-3-O-glucuronide” In the search of the full text of the gazette by the patent electronic library, documents with description of “Kaempferol-3-O-glucuronide” were not hit.
(Thus, the literature describing both “quercetin-3-O-glucuronide” and “kaempferol-3-O-glucuronide” did not hit.)
[その５]
「ケンフェロール」×「グルクロニド グルクロナイド」×「抗酸化 メイラード」の記載のある文献
[Part 5]
Literature with description of "Kaempferol" x "Glucuronide Glucuronide" x "Antioxidant Maillard"
（特許文献７）
特開２００９−１０６２６５（特許文献７）の段落０００７には、「抗酸化性の高いフラボンの７位グルクロン酸抱合体が蓄積している」旨の記載がある。
(Patent Document 7)
In paragraph 0007 of JP-A-2009-106265 (Patent Document 7), there is a description that “the 7-position glucuronide conjugate of flavone having high antioxidant property is accumulated”.
（特許文献８）
再表２０１０−０２６６６６（特許文献８）の段落０００７のすぐ前の個所には、「このようにして得られるグルクロン酸抱合体（フラボノイドの）は、機能性食品の材料、その生体内での機能を調べるための試薬、あるいは、抗酸化剤などとして有用である」旨の記載がある。
(Patent Document 8)
In the part immediately before paragraph 0007 of Table 2010-026666 (Patent Document 8), “the glucuronic acid conjugate (flavonoid) thus obtained is a functional food material, its function in vivo”. It is useful as a reagent for investigating or an antioxidant. "
（特許文献１について）
特許文献１においては、「月桃の地上部から、乾留法、減圧蒸留法、水蒸気蒸留法などの手法により月桃蒸留液を抽出した後、その蒸留液につき、分液ロート又はオイルセパレーター等で精油分を分離除去し、残った成分をろ過して、化粧品などの製造に利用している。
つまり、特許文献１の発明においては、月桃蒸留液は「精油分」と「精油分以外の部分（水分や、水に懸濁している精油分）」とからなるところ、その蒸留液のうちの「精油分以外の部分」に着目している。
特許文献１においては、蒸留操作による蒸留液以外の部分である「缶残」については何の注目もしていない。
(Regarding Patent Document 1)
In Patent Document 1, “After extracting the moon peach distillate from the above-ground part of moon peach by a method such as dry distillation, vacuum distillation, steam distillation, etc., the distillate is separated with a separatory funnel or oil separator, etc. The essential oil is separated and removed, and the remaining components are filtered for use in the production of cosmetics.
That is, in the invention of Patent Document 1, the moon peach distillate is composed of “essential oil” and “parts other than essential oil (moisture and essential oil suspended in water)”. We focus on “the part other than essential oil”.
In Patent Document 1, no attention is paid to “can residue” which is a portion other than the distillate obtained by distillation operation.
（特許文献２〜６について）
特許文献２〜６には、ケルセチン−３−Ｏ−グルクロニドあるいはその類似物質の作用効果（抗酸化作用など）についての記載があるにとどまる。
(Regarding Patent Documents 2 to 6)
Patent Documents 2 to 6 contain only a description of the action effect (antioxidant action, etc.) of quercetin-3-O-glucuronide or a similar substance.
（特許文献７〜８について）
特許文献７〜８には、ケンフェロール−３−Ｏ−グルクロニドあるいはその類似物質の作用効果（抗酸化作用など）についての記載があるにとどまる。
(Regarding Patent Documents 7 to 8)
Patent Documents 7 to 8 merely describe the action and effect (antioxidant action and the like) of kaempferol-3-O-glucuronide or a similar substance.
（特許文献１、２〜６、７〜８についてのまとめ）
−１−
上述の特許文献１においては、月桃葉の蒸留液に着目しているが、上述のように、蒸留液以外の部分である「缶残」については何らの注目も払っていない。
(Summary about patent documents 1, 2-6, 7-8)
-1-
In the above-mentioned patent document 1, attention is paid to the distillate of moon peach leaves, but as mentioned above, no attention is paid to the “can residue” which is a part other than the distillate.
−２−
上記の特許文献２〜６にはケルセチン−３−Ｏ−グルクロニドの抗酸化作用などにつき記載があり、上記の特許文献７〜８にはケンフェロール−３−Ｏ−グルクロニドの抗酸化作用などにつき記載があるが、本願発明のように、
・植物原料として月桃葉に着目すること、
・「低温減圧乾留残渣（Ｒ）そのもの」またはその「低温減圧乾留残渣（Ｒ）からの溶媒による抽出物（Ｅ）」を有効成分とすること、
・ケルセチン−３−Ｏ−グルクロニドとケンフェロール−３−Ｏ−グルクロニドとの双方」を含有するものであること、
については、いずれも記載がない。
-2-
The above Patent Documents 2 to 6 describe the antioxidant action of quercetin-3-O-glucuronide, and the above Patent Documents 7 to 8 describe the antioxidant action of kaempferol-3-O-glucuronide. However, as in the present invention,
-Focus on moon peach leaves as plant raw materials,
-"Low temperature vacuum distillation residue (R) itself" or its "extract by solvent from low temperature vacuum distillation residue (R) (E)" as an active ingredient,
-Both quercetin-3-O-glucuronide and kaempferol-3-O-glucuronide "
There is no description about either.
−３−
これらの特許文献１〜８に記載の発明は、本願発明とは着眼点や技術思想が相違しているのである。
-3-
The inventions described in these Patent Documents 1 to 8 are different from the present invention in terms of focus and technical idea.
本発明のメイラード反応抑制機能または／および抗酸化機能を有する機能剤は、
減圧機構を備えた乾留装置を用いて含水状態にある植物原料を低温かつ減圧条件下に乾留したときに留出する成分を「低温減圧乾留留出分（Ｄ）」としかつその低温減圧乾留操作後にその乾留装置内に残る乾燥状態の粉末ないしフレーク状の残渣を「低温減圧乾留残渣（Ｒ）」と称するとき、
前記の植物原料が月桃葉であること、
その月桃葉の「低温減圧乾留残渣（Ｒ）そのもの」またはその「低温減圧乾留残渣（Ｒ）からの溶媒による抽出物（Ｅ）」を有効成分とするものであること、および、
前記の残渣（Ｒ）または抽出物（Ｅ）が、「ケルセチン−３−Ｏ−グルクロニドとケンフェロール−３−Ｏ−グルクロニドとの双方」を含有するものであること、
を特徴とするものである。
The functional agent having the Maillard reaction inhibitory function or / and antioxidant function of the present invention,
The component which is distilled when the plant raw material in the water-containing state is subjected to dry distillation under low temperature and reduced pressure conditions using a dry distillation apparatus equipped with a vacuum mechanism is referred to as “low temperature reduced pressure dry distillation fraction (D)” and the low temperature reduced pressure dry distillation operation When a dry powder or flaky residue that remains in the carbonization apparatus later is referred to as a “low temperature vacuum distillation residue (R)”,
The plant material is moon peach leaves,
The moon peach leaf "low-temperature vacuum dry distillation residue (R) itself" or the "low-temperature vacuum dry distillation residue (R) extract by solvent (E)" as an active ingredient, and
Said residue (R) or extract (E) contains "both quercetin-3-O-glucuronide and kaempferol-3-O-glucuronide",
It is characterized by.
ここで、上記のメイラード反応抑制機能を有する機能剤は、メイラード反応抑制剤、特にそのメイラード反応抑制剤の範疇の中のペントシジン生成阻害剤であることが特に好ましい。 Here, the functional agent having the Maillard reaction inhibitory function is particularly preferably a Maillard reaction inhibitor, particularly a pentosidine production inhibitor in the category of the Maillard reaction inhibitor.
また、上記の抗酸化機能を有する機能剤は、抗酸化剤であることが特に好ましい。 In addition, the functional agent having the antioxidant function is particularly preferably an antioxidant.
そして、上記の低温減圧乾留操作は、より具体的には、水分率が９０重量％以下の含水状態にある月桃葉を、６０〜２０℃の低温条件下にかつゲージ圧で−８８ｋＰａ以下の減圧条件下に行う乾留操作であることが特に好ましい。 More specifically, the low-temperature vacuum distillation operation described above is more specifically performed on a peach leaf in a water-containing state having a moisture content of 90% by weight or less under a low temperature condition of 60 to 20 ° C. and a gauge pressure of −88 kPa or less. Particularly preferred is a carbonization operation performed under conditions.
（着想の特異性と作用効果について）
−１−
本発明者らは、植物原料として月桃葉に着目している。
月桃葉を蒸留したときの留分（蒸留エキス）の良い香りの成分はテルピネン−４−オールであることが知られており、本発明者らもそのことを確認しているが、本発明者らは、月桃葉については、その蒸留エキス以外の部分に何らかの未知の可能性があるとの予感を抱いていたのである。
(Specificity of idea and action effect)
-1-
The present inventors have focused on moon peach leaves as plant materials.
The fragrant component of the fraction (distilled extract) obtained by distilling moon peach leaves is known to be terpinen-4-ol, and the present inventors have confirmed that. Et al. Had a premonition that there were some unknown possibilities for the moon peach leaves other than the distilled extract.
−２−
特許文献１のように、植物中の着目成分（Ａとする）は、蒸留により留出する留分に含まれるとするのが技術上の通念であり、乾留装置内に残る固体状の残渣（缶残）は、本来は廃棄物として処理されるべきものである。
蒸留操作により留分中に移行するはずの着目成分Ａの一部が残渣（缶残）側に残るので、その着目成分Ａを残渣側から少しでも回収しようとすることは考えられるが、残渣から回収した着目成分Ａは純度が劣りかつ不純物や着色物が入り込むおそれがあるので、化粧品原料に使用するようなケースにおいてはそのような回収はしないのが通常である。たとえ回収するときでも、その回収物につき精製処理を施すことが必要となるので、かえってコスト的に割高になってしまうのである。
-2-
As in Patent Document 1, it is a technical wisdom that the component of interest (referred to as A) in a plant is contained in a fraction distilled by distillation, and a solid residue ( The can residue is originally to be treated as waste.
Since a part of the target component A that should be transferred into the fraction by distillation operation remains on the residue (can residue) side, it is conceivable to attempt to recover the target component A from the residue side as much as possible. Since the recovered component A of interest is inferior in purity and may contain impurities and colored substances, such recovery is usually not performed in cases where it is used as a cosmetic raw material. Even if it is collected, it is necessary to carry out a purification process for the collected material, which is rather expensive.
−３−
しかるに、本発明者らは、その月桃葉について「常温程度の低温での減圧乾留」を行ったときに乾留装置内に残る固体状の残渣（低温減圧乾留残渣（Ｒ））に着目し、
その残渣（Ｒ）そのもの、および、
その残渣（Ｒ）からの溶媒による抽出物（Ｅ）
が、抗酸化機能または／およびペントシジン生成阻害率の点ですぐれた作用効果を示すという予想外の事実を見い出すに至ったのである。
ここで「予想外」と形容したのは、植物原料に含まれる有効成分は減圧乾留液（留出液）の方に移行しかつ減圧乾留操作中に分解ないし変性により生じた有効成分も減圧乾留液（留出液）の方に移行し、減圧乾留残渣の側には有効成分は余り残らないと考えるのが常識的であるからである。
-3-
However, the present inventors pay attention to the solid residue (low-temperature vacuum dry distillation residue (R)) remaining in the dry distillation apparatus when performing “vacuum dry distillation at a low temperature of about normal temperature” for the moon peach leaves,
The residue (R) itself, and
Extract (E) with solvent from the residue (R)
Has come to find the unexpected fact that it exhibits an excellent effect in terms of antioxidant function or / and inhibition of pentosidine production.
Here, “unexpected” describes that the active ingredient contained in the plant raw material is transferred to the vacuum distillation solution (distillate), and the active ingredient produced by decomposition or modification during the vacuum distillation operation is also vacuum distillation. This is because it is common sense to move toward the liquid (distilled liquid) and think that there is not much active ingredient on the vacuum dry distillation residue side.
−４−
そして、前記の低温減圧乾留操作は、水分率が９０重量％以下の含水状態にある月桃葉を、６０〜２０℃の低温条件下にかつゲージ圧で−８８ｋＰａ以下の減圧条件下に行う乾留操作であることが望ましい。
-4-
The low-temperature reduced-pressure dry distillation operation is a dry-distillation operation in which moon peach leaves in a water-containing state having a moisture content of 90% by weight or less are subjected to a low-temperature condition of 60 to 20 ° C. and a reduced-pressure condition of −88 kPa or less in gauge pressure It is desirable that
（月桃葉）
本発明においては、植物原料として月桃葉（つまり「月桃の葉部」）を用いる。月桃葉を用いたときに、本発明の目的に沿う有効成分を含む目的物が得られるからである。
月桃葉の減圧乾留を行うにあたっては、月桃の葉が極めて大きいことから、必要な大きさにまで裁断しておく。なお、月桃の葉部以外に月桃の他の部位が混在していても、特に支障とはならない。
(Moon peach leaves)
In the present invention, moon peach leaves (that is, “moon peach leaves”) are used as plant materials. This is because when moon peach leaves are used, an object containing an active ingredient that meets the object of the present invention can be obtained.
When performing vacuum distillation of moon peach leaves, the peach leaves are extremely large, so they are cut to the required size. In addition, even if other parts of the moon peach besides the moon peach leaves are mixed, there is no particular problem.
（低温減圧乾留時の水分率の条件）
本発明においては、減圧機構を備えた乾留装置を用いて含水状態にある月桃葉を低温かつ減圧条件下に乾留する。ただし、水分率が余りに高いときは乾留に長時間を要し、工業性を欠くことになるので、水分率は９０重量％以下にとどめることが望ましい。
(Condition of moisture content during low-temperature vacuum distillation)
In the present invention, the moon peach leaves in a water-containing state are subjected to dry distillation under a low temperature and reduced pressure using a dry distillation apparatus equipped with a reduced pressure mechanism. However, when the moisture content is too high, dry distillation takes a long time and industrial properties are lacking. Therefore, it is desirable to keep the moisture content at 90% by weight or less.
（低温減圧乾留時の温度条件と圧力条件）
−１−
低温減圧乾留を行うときの温度条件としては、６０〜２０℃程度の範囲内の低温が適当であり、より好ましい範囲は５５〜２５℃、さらに好ましい範囲は５０〜３０℃である。
温度条件が６０℃を越えるような条件で減圧乾留を行うと、乾留装置内に残る固体状の残渣を溶媒で抽出してもその抽出物（Ｅ）中の有効成分の量が少なくなる上、取得した抽出物（Ｅ）を用いたときのメイラード反応抑制機能や抗酸化機能が不足するようになる傾向がある。
−２−
低温減圧乾留を行うときの圧力条件（減圧条件）としては、ゲージ圧表記で、−８８ｋＰａ以下（−６６０ｍｍＨｇ以下）、通常は−９６〜−１００ｋＰａ（−７２０〜−７５０ｍｍＨｇ）とすることが好ましい。
絶対圧表記では、１３．３ｋＰａ以下（１００ｍｍＨｇ以下）、通常は１．３〜５．３ｋＰａ（１０〜４０ｍｍＨｇ）とすることが好ましい。
減圧の度合いが上記範囲よりも緩くなると（減圧度が不足すると）乾留に長時間を要することになり、一方、減圧の度合いを余りに大きくすることは真空装置上の制約があるので、いずれも工業性を欠くことになる。
−３−
上述のような条件下での低温減圧乾留により、所期の目的物を工業的に効率良く取得できる。
(Temperature and pressure conditions during low-temperature vacuum distillation)
-1-
As a temperature condition when performing low-temperature vacuum distillation, a low temperature in the range of about 60 to 20 ° C is appropriate, a more preferable range is 55 to 25 ° C, and a further preferable range is 50 to 30 ° C.
When vacuum distillation is carried out under conditions where the temperature exceeds 60 ° C., the amount of the active ingredient in the extract (E) decreases even if the solid residue remaining in the distillation apparatus is extracted with a solvent. When the acquired extract (E) is used, the Maillard reaction suppression function and the antioxidant function tend to be insufficient.
-2-
The pressure condition (depressurization condition) when performing low temperature vacuum distillation is preferably -88 kPa or less (-660 mmHg or less), usually -96 to -100 kPa (-720 to -750 mmHg) in gauge pressure notation.
In absolute pressure notation, it is preferably 13.3 kPa or less (100 mmHg or less), usually 1.3 to 5.3 kPa (10 to 40 mmHg).
If the degree of decompression is less than the above range (when the degree of decompression is insufficient), it will take a long time for dry distillation. On the other hand, too large a degree of decompression has restrictions on the vacuum equipment, so both are industrial. Lack of sex.
-3-
The desired product can be industrially efficiently obtained by low-temperature vacuum distillation under the above-described conditions.
（低温減圧乾留残渣（Ｒ））
−１−
上記のようにして低温減圧乾留を行ったときに乾留装置内に残る固体状の残渣である「低温減圧乾留残渣（Ｒ）そのもの」が本発明の目的物である。
また、その「低温減圧乾留残渣（Ｒ）からの溶媒による抽出物（Ｅ）」も本発明の目的物である。ここで溶媒としては種々の溶媒が使用できるが、水、エタノール、これらの混合物が特に好適である。
−２−
前者の「低温減圧乾留残渣（Ｒ）」はそれ自体が製品となるが、その製品の購入業者はいずれその残渣（Ｒ）を用いて溶媒による抽出を行って抽出物（Ｅ）となし、その抽出物（Ｅ）を自ら使用して二次製品や三次製品を製造・販売したり、その抽出物（Ｅ）をさらに第三者に販売することになる。
−３−
後者の「低温減圧乾留残渣（Ｒ）からの溶媒による抽出物（Ｅ）」は、メイラード反応抑制機能または抗酸化機能としての好ましい性能を有するので（ちなみにこれら双方の機能を併せ有することも多い）、極めて有用である。
(Low temperature vacuum distillation residue (R))
-1-
“Low-temperature vacuum distillation residue (R) itself”, which is a solid residue remaining in the carbonization apparatus when performing low-temperature vacuum distillation as described above, is an object of the present invention.
Further, the “extract (E) with a solvent from the low-temperature vacuum distillation residue (R)” is also an object of the present invention. Here, various solvents can be used as the solvent, but water, ethanol, and a mixture thereof are particularly suitable.
-2-
The former “low-temperature vacuum distillation residue (R)” itself becomes a product, but the purchaser of the product eventually uses the residue (R) to perform extraction with a solvent to obtain an extract (E). The extract (E) is used by itself to manufacture and sell secondary products and tertiary products, and the extract (E) is further sold to a third party.
-3-
Since the latter “extract (E) by solvent from low-temperature reduced-pressure dry distillation residue (R)” has a preferable performance as a Maillard reaction suppressing function or an antioxidant function (in many cases, both functions are combined). Is extremely useful.
（低温減圧乾留留出分（Ｄ））
一方、上記の低温減圧乾留による「低温減圧乾留留出分（Ｄ）」は、本発明の目的物ではないが、抗菌成分や香気成分を含むので、無駄にはならない。
(Low temperature vacuum distillation distillation (D))
On the other hand, the “low-temperature reduced-pressure dry distillation fraction (D)” by the low-temperature reduced-pressure dry distillation is not an object of the present invention, but is not wasted because it contains an antibacterial component and an aroma component.
次に実施例をあげて本発明をさらに説明する。 The following examples further illustrate the invention.
（第１）月桃葉乾燥粉末の５０％エタノール抽出
月桃葉乾燥粉末１０ｇを秤り、５０体積％エタノール水（以下「５０％エタノール」というように略称する）１００ｍＬを加え、２時間室温で攪拌抽出した。抽出液を遠心分離し、上清を濾紙濾過した。残渣に５０％エタノール５０ｍＬを加え、室温で更に１時間抽出した。抽出液を遠心分離し、上清を濾紙濾過した。濾液を合わせて減圧濃縮し、残渣１．２２ｇを得た。
(First) 50% ethanol extraction of dried moon peach leaf powder Weighed 10 g of dried moon peach leaf powder, added 100 mL of 50 vol% ethanol water (hereinafter abbreviated as “50% ethanol”), and stirred and extracted at room temperature for 2 hours. did. The extract was centrifuged and the supernatant was filtered through filter paper. To the residue was added 50 mL of 50% ethanol, and the mixture was further extracted at room temperature for 1 hour. The extract was centrifuged and the supernatant was filtered through filter paper. The filtrates were combined and concentrated under reduced pressure to obtain 1.22 g of residue.
（第２）残渣のＯＤＳカラム精製
残渣に１０％エタノール２０ｍＬを加え、撹拌抽出した。不溶物を遠心濾過で除き、上清を濾紙濾過した。
濾液をＯＤＳカラム（１７５ｍＬ，２．５ｘ３５ｃｍ）にチャージした。１０％エタノール、２０％エタノール、３０％エタノール、５０％エタノールの順で溶出液をそれぞれ２５０ｍＬ得た。
(Second) ODS column purification of residue 20 mL of 10% ethanol was added to the residue and extracted with stirring. Insoluble matter was removed by centrifugal filtration, and the supernatant was filtered through filter paper.
The filtrate was charged to an ODS column (175 mL, 2.5 × 35 cm). 250 mL of eluate was obtained in the order of 10% ethanol, 20% ethanol, 30% ethanol, and 50% ethanol.
（第３）各溶出液の抗酸化活性とメイラード反応抑制活性（ペントシジン生成阻害活性）の測定
（１）方法
（その１）抗酸化活性
（１−１）４００μＭ ＤＰＰＨ（１，１−ｄｉｐｈｅｎｙｌ−２−ｐｉｃｒｙｌｈｙｄｒａｚｙｌ）エタノール溶液の調製
ＤＰＰＨ ３．９４ｍｇを秤量し、エタノール２５ｍＬに攪拌溶解する。
(Third) Measurement of Antioxidant Activity and Maillard Reaction Inhibitory Activity (Pentocidin Production Inhibitory Activity) of Each Eluate (1) Method
(Part 1) Antioxidant activity (1-1) Preparation of 400 μM DPPH (1,1-diphenyl-2-picrylhydrazyl) ethanol solution 3.94 mg of DPPH is weighed and dissolved in 25 mL of ethanol with stirring.
（１−２）検量線の作成
ア：４００μＭ ＤＰＰＨエタノール溶液をエタノールで３倍に希釈し、その希釈液０．９ｍＬを試験管に分注する。
イ：希釈液の入った試験管にエタノール３００，２５０，２００，１５０，１００μＬをｎ＝２で添加する。
ウ：０．２ｍＭ α−トコフェロールエタノール溶液（８．６ｍｇ→エタノール１００ｍＬ）をイで加えたエタノールと０．２ｍＭ α−トコフェロールエタノール溶液の合計が３００μＬになるよう試験管（ｎ＝２）に添加し、攪拌する。このとき、α−トコフェロールの量は０，１０，２０，３０，４０ｎｍｏｌ／ａｓｓａｙとなる。
エ：添加２０分後に５１６ｎｍで吸光度を測定する。
オ：横軸にα−トコフェロール量（ｎｍｏｌ／ａｓｓａｙ）、縦軸に吸光度をプロットし、最小二乗法により、検量線を作成する。
(1-2) Preparation of calibration curve A: A 400 μM DPPH ethanol solution is diluted 3 times with ethanol, and 0.9 mL of the diluted solution is dispensed into a test tube.
A: Add 300, 250, 200, 150, and 100 μL of ethanol to a test tube containing the diluted solution at n = 2.
C: Add 0.2 mM α-tocopherol ethanol solution (8.6 mg → 100 mL of ethanol) to the test tube (n = 2) so that the total of the ethanol and 0.2 mM α-tocopherol ethanol solution is 300 μL. , Stir. At this time, the amount of α-tocopherol is 0, 10, 20, 30, 40 nmol / assay.
D: The absorbance is measured at 516 nm 20 minutes after the addition.
E: The amount of α-tocopherol (nmol / assay) is plotted on the horizontal axis, and the absorbance is plotted on the vertical axis, and a calibration curve is prepared by the least square method.
（１−３）試験液の測定
ア：ＤＰＰＨ希釈液０．９ｍＬを試験管に分注し、それにエタノール２５０μＬを添加する。
イ：試験液５０μＬを試験管（ｎ＝２）に添加し、攪拌する。
ウ：添加２０分後に５１６ｎｍで吸光度を測定する。
エ：得られた吸光度より、検量線を用いてα−トコフェロール相当量を算出する。
(1-3) Measurement of test solution A: Dispense 0.9 mL of DPPH diluted solution into a test tube, and add 250 μL of ethanol thereto.
A: Add 50 μL of the test solution to a test tube (n = 2) and stir.
C: The absorbance is measured at 516 nm 20 minutes after the addition.
D: From the obtained absorbance, an α-tocopherol equivalent amount is calculated using a calibration curve.
（その２）メイラード反応抑制活性（ペントシジン生成阻害）
下記の表に示す組成の反応液を１．５ｍＬ容量のプラスチックチューブに調製し、６０℃、２４時間ヒートブロック上でインキュベートした。
(Part 2) Maillard reaction inhibitory activity (inhibition of pentosidine production)
A reaction solution having the composition shown in the following table was prepared in a 1.5 mL plastic tube and incubated on a heat block at 60 ° C. for 24 hours.
反応終了後、反応液１００μＬに４００μＬの精製水を加え、その希釈液をＨＰＬＣ分析することにより得られるペントシジンのピーク面積を測定し、阻害率を求めた。
また、アミノグアニジン塩酸塩の１０ｍＭ液を陽性コントロールとした。
After completion of the reaction, 400 μL of purified water was added to 100 μL of the reaction solution, and the peak area of pentosidine obtained by HPLC analysis of the diluted solution was measured to determine the inhibition rate.
A 10 mM solution of aminoguanidine hydrochloride was used as a positive control.
・ＨＰＬＣ分析条件
カラム： ＹＭＣ−Ｐａｃｋ ＯＤＳ Ａ−３１２ １５０×６ｍｍＩ．Ｄ．
溶出液： ３％ＣＨ３ＣＮ／０．１％ＴＦＡ
流量： １．０ｍＬ／ｍｉｎ、カラム温度 ４０℃
検出器： 分光蛍光検出器 ＥＸ３３５ｎｍ、ＥＭ３８０ｎｍ
注入量： ２０μＬ
保持時間：約１２分
HPLC analysis conditions Column: YMC-Pack ODS A-312 150 × 6 mmI. D.
Eluent: 3% CH3CN / 0.1% TFA
Flow rate: 1.0 mL / min, column temperature 40 ° C
Detector: Spectral fluorescence detector EX335nm, EM380nm
Injection volume: 20 μL
Retention time: about 12 minutes
・阻害率
阻害率（％）＝１００−[（試料溶液のペントシジンのピーク面積／ブランクのペントシジンのピーク面積）×１００]
Inhibition rate Inhibition rate (%) = 100 − [(peak area of pentosidine in sample solution / peak area of pentosidine in blank) × 100]
（その３）結果
結果を次の表２に示す。
(Part 3) Results The results are shown in Table 2 below.
上記の結果から、抗酸化活性物質およびメイラード反応抑制活性物質は、主として２０％エタノール溶出液中に含まれていることが示された。 From the above results, it was shown that the antioxidant active substance and the Maillard reaction inhibitory active substance are mainly contained in the 20% ethanol eluate.
（第４）２０％エタノール溶出液のＨＰＬＣ分析
（１）分析条件
・カラム： ＹＭＣ−Ｐａｃｋ ＯＤＳ Ａ−３１２ １５０×６ｍｍＩ．Ｄ．
・カラム温度：４０℃
・移動相： ０．１％ＴＦＡ−０．１％ＴＦＡ ｉｎ エタノール
グラジエント溶出
・検出器： ＵＶ 波長２８０ｎｍ
・流量： ０．８ｍＬ／ｍｉｎ．
・注入量： ２０μＬ
（２）ＨＰＬＣクロマトグラム
図１を参照
(4th) HPLC analysis of 20% ethanol eluate (1) Analysis conditions Column: YMC-Pack ODS A-312 150 × 6 mmI. D.
-Column temperature: 40 ° C
Mobile phase: 0.1% TFA-0.1% TFA in ethanol
Gradient elution ・ Detector: UV wavelength 280nm
-Flow rate: 0.8 mL / min.
・ Injection volume: 20μL
(2) HPLC chromatogram See Fig. 1.
（第５）２０％エタノール溶出液のＨＰＬＣ分取
２０％エタノール溶出液を減圧濃縮し、残渣１４０ｍｇを得た。これを５０％エタノール８ｍＬに溶解し、上記クロマトグラムで保持時間１５分から２５分のブロードな山の部分をフラクション１、保持時間約２８分の鋭いピークをフラクション２、保持時間約３０分の鋭いピークをフラクション３としてＨＰＬＣ分取を行った。
(5th) HPLC fractionation of 20% ethanol eluate The 20% ethanol eluate was concentrated under reduced pressure to obtain 140 mg of residue. Dissolve this in 8 mL of 50% ethanol, and in the above chromatogram, the broad peak portion with a retention time of 15 to 25 minutes is fraction 1; the sharp peak with a retention time of about 28 minutes is fraction 2; the sharp peak with a retention time of about 30 minutes Was subjected to HPLC fractionation as fraction 3.
（１）分取条件
・カラム：ＹＭＣ−Ｐａｃｋ ＯＤＳ−Ａ ２φ×２０ｃｍ
・移動相：０．５％ギ酸 ｉｎ ３０％エタノール
・カラム温度：４０℃
・流量：５ｍＬ／ｍｉｎ．
・検出：２８０ｎｍ
・注入量：０．５ｍＬ
(1) Preparative conditions ・ Column: YMC-Pack ODS-A 2φ × 20 cm
-Mobile phase: 0.5% formic acid in 30% ethanol-Column temperature: 40 ° C
-Flow rate: 5 mL / min.
・ Detection: 280 nm
・ Injection volume: 0.5 mL
（２）結果
フラクション１を３００ｍＬ、単一ピークのフラクション２を１００ｍＬ、単一ピークのフラクション３を１２５ｍＬ得た。各フラクションを減圧濃縮し、フラクション１〜３からそれぞれ１１０ｍｇ、１６ｍｇ、１９ｍｇを得た。
(2) Results 300 mL of fraction 1, 100 mL of fraction 2 with a single peak, and 125 mL of fraction 3 with a single peak were obtained. Each fraction was concentrated under reduced pressure to obtain 110 mg, 16 mg, and 19 mg from fractions 1 to 3, respectively.
（第６）フラクション１〜３のメイラード反応抑制（ペントシジン生成阻害）活性の測定
（１）結果
結果を次の表３に示す。
(Sixth) Measurement of Maillard reaction inhibition (pentocidine production inhibition) activity of fractions 1 to 3 (1) Results The results are shown in Table 3 below.
上記の結果から、フラクション２のピークとフラクション３のピークがメイラード反応抑制活性物質であることが示された。また、抗酸化活性物質も同様であることが推定された。 From the above results, it was shown that the peak of fraction 2 and the peak of fraction 3 are Maillard reaction-inhibiting active substances. It was also estimated that the antioxidant active substance was the same.
（第７）フラクション２および３の残渣のＮＭＲ測定
フラクション２および３の残渣のＮＭＲ測定を行い、それらの構造を検討した結果、フラクション２は下記の化１のケルセチン−３−Ｏ−グルクロニドであり、フラクション３は下記の化２のケンフェロール−３−Ｏ−グルクロニドであった。
(Seventh) NMR measurement of residues of fractions 2 and 3 As a result of conducting NMR measurement of residues of fractions 2 and 3 and examining their structures, fraction 2 is quercetin-3-O-glucuronide of the following chemical formula 1 Fraction 3 was kaempferol-3-O-glucuronide of Chemical Formula 2 below.
（ＮＭＲデータ）
−１−
１Ｈ−ＮＭＲ（４００ＭＨｚ、ＣＤ３ＯＤ）
δ3.45-3.61(3H,2”,3”,4”), 3.76(1H,d,J=10Hz,5”), 5.35(1H,d,J=8Hz,1”),
6.19(1H,d,J=4Hz,6), 6.39(1H,d,J=4Hz,8), 6.85(1H,d,J=8Hz,5’),
7.63(1H,dd,J=4Hz,8Hz,6’), 7.65(1H,d,J=4Hz,2’)
−２−
１３Ｃ−ＮＭＲ（１００ＭＨｚ、ＣＤ３ＯＤ）
δ72.9(C-4”), 75.5(C-2”), 77.2(C-5”), 77.7(C-3”), 94.8(C-8),
100.0(C-6), 104.4(C-1”), 105.7(C-10), 116.1(C-5’), 117.3(C-2’),
122.9(C-1’), 123.5(C-6’), 135.5(C-3), 146.0(C-3’), 149.9(C-4’),
158.5(C-9), 159.1(C-2), 163.1(C-5), 166.1(C-7), 172.5(C-6’’),
179.3(C-4)
−３−
これらのデータは、文献値（Phytochemistry, 1985, 24, 465-467）と一致していた。
(NMR data)
-1-
1H-NMR (400 MHz, CD3OD)
δ3.45-3.61 (3H, 2``, 3 '', 4 ''), 3.76 (1H, d, J = 10Hz, 5 ''), 5.35 (1H, d, J = 8Hz, 1 ''),
6.19 (1H, d, J = 4Hz, 6), 6.39 (1H, d, J = 4Hz, 8), 6.85 (1H, d, J = 8Hz, 5 '),
7.63 (1H, dd, J = 4Hz, 8Hz, 6 '), 7.65 (1H, d, J = 4Hz, 2')
-2-
13C-NMR (100 MHz, CD3OD)
δ72.9 (C-4 ″), 75.5 (C-2 ″), 77.2 (C-5 ″), 77.7 (C-3 ″), 94.8 (C-8),
100.0 (C-6), 104.4 (C-1 ''), 105.7 (C-10), 116.1 (C-5 '), 117.3 (C-2'),
122.9 (C-1 '), 123.5 (C-6'), 135.5 (C-3), 146.0 (C-3 '), 149.9 (C-4'),
158.5 (C-9), 159.1 (C-2), 163.1 (C-5), 166.1 (C-7), 172.5 (C-6``),
179.3 (C-4)
-3-
These data were consistent with literature values (Phytochemistry, 1985, 24 , 465-467).
（ＮＭＲデータ）
−１−
１Ｈ−ＮＭＲ（４００ＭＨｚ、ＣＤ３ＯＤ）
δ3.45-3.60(3H,2”,3”,4”), 3.75(1H,d,J=10Hz,5”), 5.33(1H,d,J=7Hz,1”),
6.19(1H,d,J=4Hz,6), 6.38(1H,d,J=4Hz,8), 6.86(2H,d,J=8Hz,3’,5’),
8.05(2H,d,J=8Hz,2’,6’)
−２−
１３Ｃ−ＮＭＲ（１００ＭＨｚ、ＣＤ３ＯＤ）
δ72.9(C-4”), 75.5(C-2”), 77.1(C-5”), 77.6(C-3”), 94.9(C-8), 100.0(C-6),
104.5(C-1”), 105.7(C-10), 116.2(C-3’,C-5’), 122.6(C-1’), 132.4(C-2’,C-6’),
135.4(C-3), 158.5(C-9), 159.3(C-2), 161.6(C-4’), 163.1(C-5), 166.1(C-7),
172.2(C-6”), 179.3(C-4)
(NMR data)
-1-
1H-NMR (400 MHz, CD3OD)
δ3.45-3.60 (3H, 2``, 3 '', 4 ''), 3.75 (1H, d, J = 10Hz, 5 ''), 5.33 (1H, d, J = 7Hz, 1 ''),
6.19 (1H, d, J = 4Hz, 6), 6.38 (1H, d, J = 4Hz, 8), 6.86 (2H, d, J = 8Hz, 3 ', 5'),
8.05 (2H, d, J = 8Hz, 2 ', 6')
-2-
13C-NMR (100 MHz, CD3OD)
δ72.9 (C-4 ″), 75.5 (C-2 ″), 77.1 (C-5 ″), 77.6 (C-3 ″), 94.9 (C-8), 100.0 (C-6),
104.5 (C-1 ''), 105.7 (C-10), 116.2 (C-3 ', C-5'), 122.6 (C-1 '), 132.4 (C-2', C-6 '),
135.4 (C-3), 158.5 (C-9), 159.3 (C-2), 161.6 (C-4 '), 163.1 (C-5), 166.1 (C-7),
172.2 (C-6 ”), 179.3 (C-4)
（第８）「抗酸化活性」および「メイラード反応抑制活性」の強さの検討
上述のケルセチン−３−Ｏ−グルクロニドおよびケンフェロール−３−Ｏ−グルクロニドの「抗酸化活性」および「メイラード反応抑制活性」の強さを検討した。
(8) Examination of strength of “antioxidant activity” and “Maillard reaction inhibitory activity” “Antioxidant activity” and “Maillard reaction inhibition” of quercetin-3-O-glucuronide and kaempferol-3-O-glucuronide described above The strength of “activity” was examined.
（１）抗酸化活性
ケルセチン−３−Ｏ−グルクロニドの１．０ｍＭ，０．５ｍＭ，０．２５ｍＭ，０．１２５ｍＭ，０．０６３ｍＭ−５０％ＥｔＯＨ溶液およびケンフェロール−３−Ｏ−グルクロニドの１０ｍＭ，５ｍＭ，２．５ｍＭ，１．２５ｍＭ，０．０６３ｍＭ−５０％ＥｔＯＨ溶液をそれぞれ調製し、抗酸化活性を測定した。
結果を次の表４に示す。
(1) Antioxidant activity 1.0 mM, 0.5 mM, 0.25 mM, 0.125 mM, 0.063 mM-50% EtOH solution of quercetin-3-O-glucuronide and 10 mM of kaempferol-3-O-glucuronide, 5 mM, 2.5 mM, 1.25 mM, and 0.063 mM-50% EtOH solutions were prepared, and the antioxidant activity was measured.
The results are shown in Table 4 below.
上記の結果から、ケルセチン−３−Ｏ−グルクロニドは、α−トコフェロールの１．６倍の抗酸化活性を有していることがわかる（下記の計算基礎を参照）。
一方、ケンフェロール−３−Ｏ−グルクロニドの抗酸化活性は、α−トコフェロールの２％程度にすぎず（下記の計算基礎を参照）、事実上、抗酸化活性が認められなかったことがわかる。
From the above results, it can be seen that quercetin-3-O-glucuronide has 1.6 times the antioxidant activity of α-tocopherol (see the calculation basis below).
On the other hand, the antioxidative activity of kaempferol-3-O-glucuronide is only about 2% of α-tocopherol (see the calculation basis below), indicating that virtually no antioxidative activity was observed.
[α−トコフェロールとの対比における抗酸化活性能の計算基礎]
−０−
念のため、上記の表４における「抗酸化活性」の計算基礎を、以下に項を改めて説明する。
後述の表５は、α−トコフェロールとの対比におけるケルセチン−３−Ｏ−グルクロニドの抗酸化活性能の計算基礎を示すためのものである。
後述の表６は、α−トコフェロールとの対比におけるケンフェロール−３−Ｏ−グルクロニドの抗酸化活性能の計算基礎を示すためのものである。
[Calculation basis for antioxidant activity in comparison with α-tocopherol]
-0-
As a precaution, the calculation basis of “antioxidant activity” in the above Table 4 will be described below again.
Table 5 to be described later shows the calculation basis of the antioxidant activity ability of quercetin-3-O-glucuronide in comparison with α-tocopherol.
Table 6 to be described later shows the calculation basis of the antioxidative activity ability of kaempferol-3-O-glucuronide in comparison with α-tocopherol.
−１−
（ケルセチン−３−Ｏ−グルクロニドに関して）
上記の表４の左欄の上半分の「試料（ｍＭ）」の欄が下記の表５の（Ａ）欄に対応し、上記の表４の右欄の上半分の「抗酸化活性（注１）」の欄が下記の表５の（Ｃ）欄に対応する。
-1-
(Regarding quercetin-3-O-glucuronide)
The column “Sample (mM)” in the upper half of the left column in Table 4 corresponds to the column (A) in Table 5 below, and the “Antioxidant activity (Note)” in the upper half of the right column in Table 4 above. The column “1)” corresponds to the column (C) in Table 5 below.
−２−
下記の表５の（Ｄ）欄（抗酸化活性能の比率（Ｃ）/（Ｂ）を示す）における５個の比率のうち最大値（２．２０）と最小値（０．８６）とをカットし、残りの３個の値（１．２８と１．６８と１．９０）の平均値（１．６）を、ケルセチン−３−Ｏ−グルクロニドのα−トコフェロールとの対比における抗酸化活性能の値とした。
この結果から、ケルセチン−３−Ｏ−グルクロニドは、α−トコフェロールの約１．６倍の抗酸化活性を有していることがわかる。
-2-
The maximum value (2.20) and the minimum value (0.86) among the five ratios in the column (D) (showing the ratio (C) / (B) of antioxidant activity ability) in Table 5 below. Cut the average of the remaining three values (1.28, 1.68 and 1.90) (1.6) against antioxidant activity of quercetin-3-O-glucuronide versus α-tocopherol It was set as the value of Noh.
This result shows that quercetin-3-O-glucuronide has an antioxidant activity about 1.6 times that of α-tocopherol.
−３−
（ケンフェロール−３−Ｏ−グルクロニドに関して）
上記の表４の左欄の下半分の「試料（ｍＭ）」の欄が下記の表６の（Ａ）欄に対応し、上記の表４の右欄の下半分の「抗酸化活性（注１）」の欄が下記の表６の（Ｃ）欄に対応する。
-3-
(For kaempferol-3-O-glucuronide)
The column of “Sample (mM)” in the lower half of the left column of Table 4 corresponds to the column (A) of Table 6 below, and “Antioxidant activity (Note)” in the lower half of the right column of Table 4 above. The column “1)” corresponds to the column (C) in Table 6 below.
−４−
上記の表６の（Ｄ）欄（抗酸化活性能の比率（Ｃ）/（Ｂ）を示す）における５個の比率のうち最大値（０．０６３）と最小値（０．０１４）とをカットし、残りの３個の値（０．０１６と０．０２４と０．０３２）の平均値（０．０２４）を、ケンフェロール−３−Ｏ−グルクロニドのα−トコフェロールとの対比における抗酸化活性能の値とした。
この結果から、ケンフェロール−３−Ｏ−グルクロニドは、α−トコフェロールの０．０２４倍（約０．０２倍、つまり２％）の抗酸化活性を有しているにすぎなかったことがわかる。
すなわち、ケンフェロール−３−Ｏ−グルクロニドについては、ケルセチン−３−Ｏ−グルクロニドとは異なり、抗酸化活性は奏されなかった。
-4-
The maximum value (0.063) and the minimum value (0.014) among the five ratios in the column (D) (showing the ratio of antioxidant activity (C) / (B)) in Table 6 above. Cut and average the remaining three values (0.016, 0.024 and 0.032) (0.024) against antioxidants of kaempferol-3-O-glucuronide versus α-tocopherol It was set as the value of activity ability.
From this result, it can be seen that kaempferol-3-O-glucuronide only had an antioxidant activity of 0.024 times (about 0.02 times, that is, 2%) of α-tocopherol.
That is, kaempferol-3-O-glucuronide did not exhibit antioxidant activity unlike quercetin-3-O-glucuronide.
−５−
しかしながら、本発明の「低温減圧乾留残渣（Ｒ）そのもの」またはその「低温減圧乾留残渣（Ｒ）からの溶媒による抽出物（Ｅ）」は、ケルセチン−３−Ｏ−グルクロニドとケンフェロール−３−Ｏ−グルクロニドとの双方を含むので、結局は抗酸化活性についても好ましい作用を示すことになる。
-5-
However, “the low-temperature vacuum distillation residue (R) itself” or “the extract from the low-temperature vacuum distillation residue (R) by the solvent (E)” of the present invention is quercetin-3-O-glucuronide and kaempferol-3- Since both O-glucuronide and O-glucuronide are contained, the antioxidative activity is also shown to be favorable.
（その２）メイラード反応抑制活性（ペントシジン生成阻害活性）
（２−１）ペントシジン生成阻害活性の測定
ケルセチン−３−Ｏ−グルクロニドの１．０ｍＭ，０．５ｍＭ，０．２５ｍＭ，０．１２５ｍＭ，０．０６３ｍＭ−５０％ＥｔＯＨ溶液と、およびケンフェロール−３−Ｏ−グルクロニドの１０ｍＭ，５ｍＭ，２．５ｍＭ，１．２５ｍＭ，０．０６３ｍＭ−５０％ＥｔＯＨ溶液とをそれぞれ調製し、メイラード反応抑制活性（ペントシジン生成阻害率）を測定した。
結果を表７および表８に示す。
(Part 2) Maillard reaction inhibitory activity (pentosidine production inhibitory activity)
(2-1) Measurement of pentosidine production inhibitory activity Quercetin-3-O-glucuronide in 1.0 mM, 0.5 mM, 0.25 mM, 0.125 mM, 0.063 mM-50% EtOH solution, and kaempferol-3 -O-glucuronide in 10 mM, 5 mM, 2.5 mM, 1.25 mM, and 0.063 mM-50% EtOH solutions were prepared, and Maillard reaction inhibitory activity (pentocidin production inhibition rate) was measured.
The results are shown in Table 7 and Table 8.
（２−２）測定結果
測定結果を次の表７と表８に示す。
(2-2) Measurement results The measurement results are shown in Tables 7 and 8 below.
（２−４）解析
−１−
上記の表７の結果から、ケルセチン−３−Ｏ−グルクロニドの５０％阻害率濃度は０．５ｍＭであり、一方、陽性コントロールであるアミノグアニジン塩酸塩の５０％阻害率濃度は１０ｍＭ強であるので、ケルセチン−３−Ｏ−グルクロニドはアミノグアニジン塩酸塩のおよそ２０倍（１０ｍＭ／０．５ｍＭ≒２０）の強さのメイラード反応抑制活性を示したことがわかる。（なお、５０％阻害率濃度は、表７の濃度と阻害率とをプロットすることにより求めることができる。）
(2-4) Analysis-1-
From the results in Table 7 above, the 50% inhibition rate concentration of quercetin-3-O-glucuronide is 0.5 mM, whereas the 50% inhibition rate concentration of aminoguanidine hydrochloride, which is a positive control, is slightly over 10 mM. It can be seen that quercetin-3-O-glucuronide exhibited Maillard reaction inhibitory activity about 20 times as strong as aminoguanidine hydrochloride (10 mM / 0.5 mM≈20). (The 50% inhibition rate concentration can be obtained by plotting the concentrations and inhibition rates in Table 7.)
−２−
また、上記の表８の結果から、ケンフェロール−３−Ｏ−グルクロニドの５０％阻害率濃度は３ｍＭであり、一方、陽性コントロールであるアミノグアニジン塩酸塩の５０％阻害率濃度は１０ｍＭ強となるので（１０ｍＭの場合の阻害率が４５％なのでそれよりも数％大きくなる）、ケンフェロール−３−Ｏ−グルクロニドはアミノグアニジン塩酸塩の３．５倍程度の強さのメイラード反応抑制活性を示したことがわかる。（なお、５０％阻害率濃度は、表８の濃度と阻害率とをプロットすることにより求めることができる。）
-2-
Moreover, from the result of said Table 8, the 50% inhibition rate density | concentration of kaempferol-3-O-glucuronide is 3 mM, On the other hand, the 50% inhibition rate density | concentration of aminoguanidine hydrochloride which is positive control becomes a little over 10 mM. Therefore, kaempferol-3-O-glucuronide exhibits a Maillard reaction inhibitory activity about 3.5 times stronger than aminoguanidine hydrochloride. I understand that. (The 50% inhibition rate concentration can be obtained by plotting the concentrations and inhibition rates in Table 8.)
月桃葉の「低温減圧乾留残渣（Ｒ）そのもの」またはその「低温減圧乾留残渣（Ｒ）からの溶媒による抽出物（Ｅ）」を有効成分とし、かつ、前記の残渣（Ｒ）または抽出物（Ｅ）が「ケルセチン−３−Ｏ−グルクロニドとケンフェロール−３−Ｏ−グルクロニドとの双方」を含有する本発明の機能剤は、メイラード反応抑制剤としても抗酸化剤としてもすぐれた作用を示すので、化粧品をはじめとする外用剤、食品、医薬部外品などへの添加剤として有用である。
Tsukitomo's “low-temperature vacuum distillation residue (R) itself” or its “extract with solvent from low-temperature vacuum distillation residue (R) (E)” as an active ingredient, and the residue (R) or extract ( The functional agent of the present invention in which E) contains “both quercetin-3-O-glucuronide and kaempferol-3-O-glucuronide” exhibits an excellent action as both a Maillard reaction inhibitor and an antioxidant. Therefore, it is useful as an additive for external preparations such as cosmetics, foods, quasi drugs and the like.
Claims (5)
前記の植物原料が月桃葉であること、
その月桃葉の「低温減圧乾留残渣（Ｒ）そのもの」またはその「低温減圧乾留残渣（Ｒ）からの溶媒による抽出物（Ｅ）」を有効成分とするものであること、および、
前記の残渣（Ｒ）または抽出物（Ｅ）が、「ケルセチン−３−Ｏ−グルクロニドとケンフェロール−３−Ｏ−グルクロニドとの双方」を含有するものであること、
を特徴とするメイラード反応抑制機能または／および抗酸化機能を有する機能剤。 The component which is distilled when the plant raw material in the water-containing state is subjected to dry distillation under low temperature and reduced pressure conditions using a dry distillation apparatus equipped with a vacuum mechanism is referred to as “low temperature reduced pressure dry distillation fraction (D)” and the low temperature reduced pressure dry distillation operation When a dry powder or flaky residue that remains in the carbonization apparatus later is referred to as a “low temperature vacuum distillation residue (R)”,
The plant material is moon peach leaves,
The moon peach leaf "low-temperature vacuum dry distillation residue (R) itself" or the "low-temperature vacuum dry distillation residue (R) extract by solvent (E)" as an active ingredient, and
Said residue (R) or extract (E) contains "both quercetin-3-O-glucuronide and kaempferol-3-O-glucuronide",
A functional agent having a Maillard reaction inhibitory function or / and an antioxidant function.
The low-temperature vacuum distillation operation described above is a carbonization operation in which moon peach leaves in a water-containing state having a moisture content of 90% by weight or less are subjected to a low-temperature condition of 60 to 20 ° C. and a reduced-pressure condition of −88 kPa or less in gauge pressure. The functional agent according to claim 1.
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