JP5285852B2 - DFAIII production method and DFAIII-rich plant extract - Google Patents
DFAIII production method and DFAIII-rich plant extract Download PDFInfo
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- JP5285852B2 JP5285852B2 JP2006356119A JP2006356119A JP5285852B2 JP 5285852 B2 JP5285852 B2 JP 5285852B2 JP 2006356119 A JP2006356119 A JP 2006356119A JP 2006356119 A JP2006356119 A JP 2006356119A JP 5285852 B2 JP5285852 B2 JP 5285852B2
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Classifications
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- A61K36/8962—Allium, e.g. garden onion, leek, garlic or chives
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- A—HUMAN NECESSITIES
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- A23K20/00—Accessory food factors for animal feeding-stuffs
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- A23K20/163—Sugars; Polysaccharides
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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Description
本発明は、DFAIIIの製造方法及びDFAIII高含有植物エキスに関する。 The present invention relates to a method for producing DFAIII and a DFAIII-rich plant extract.
本出願人は、ダイフラクトースアンハイドライドIIIに着目して、その活用について研究開発を続けており、いくつかの提案をしてきた。例えば、特許文献1(特開2006−241057号公報)カルシウム吸収促進組成物およびその利用、特許文献2(特開2006−104103号公報)ダイフラクトースアンハイドライド含有経口組成物、特許文献3(特開2006−83141号公報)速崩壊性固形製剤、特許文献4(特開2006−36656号公報)DFA含有経皮吸収促進剤、特許文献5(特開2006−6177号公報)DFAと砂糖を含有するコーヒーエキス組成物及び飲料、特許文献6(特開2005−170855号公報)結晶又は結晶粒子末ダイフラクトースアンハイドライドIII、特許文献7(特開2004−149427号公報)ミネラル吸収亢進組成物、特許文献8(特開2004−137194号公報)便通改善組成物等がある。 The present applicant has paid attention to the difructose anhydride III, has continued research and development on its utilization, and has made several proposals. For example, Patent Document 1 (Japanese Patent Laid-Open No. 2006-241057) Calcium absorption promoting composition and use thereof, Patent Document 2 (Japanese Patent Laid-Open No. 2006-104103) Oral composition containing difructose anhydride, Patent Document 3 (Japanese Patent Laid-Open No. 2006-104103) 2006-83141) Fast disintegrating solid preparation, Patent Document 4 (Japanese Patent Laid-Open No. 2006-36656) DFA-containing transdermal absorption promoter, Patent Document 5 (Japanese Patent Laid-Open No. 2006-6177) containing DFA and sugar Coffee extract composition and beverage, Patent Document 6 (Japanese Patent Laid-Open No. 2005-170855) Crystalline or Crystal Particle Powder Difructose Anhydride III, Patent Document 7 (Japanese Patent Laid-Open No. 2004-149427) Mineral Absorption Enhancement Composition, Patent Document 8 (Japanese Patent Application Laid-Open No. 2004-137194).
ダイフラクトースアンハイドライドIII(di-D-fructo-furanose 1,2’:2,3’ dianyhyd
ride(以下「DFAIII」と称する場合もある)は、フラクトース2分子の還元末端がお互い
に他のフラクトース還元末端以外の水酸基に環状に結合するという特異な構造を持った難消化性オリゴ糖である。その生理機能として小腸および大腸において高いミネラル吸収促進機能を持つことがラットやヒトにおいて確認されている。また、非う蝕性、低カロリー、血糖値やインスリン値に影響を及ぼさないといった特徴を有し、機能性糖類として利用されている(非特許文献1 製糖技術研究会誌, 51, 27-32 (2003)「新規オリゴ糖DFAIIIの機能性について」)、(非特許文献2 社団法人菓子総合技術センター発行、2004, p. 1-16.「農林水産省総合食料局食品産業振興課推薦“食品新素材有効利用技術シリーズ14 ダイフラクトース アンハイドライドIII(ツイントース)」)、(非特許文献3 富田響子著「新規オリゴ糖「ツイントース」の機能性と応用,機能性糖質素材の開発と食品への応用」 p.179-187 (2005).)シーエムシー出版)。
Di-D-fructo-furanose 1,2 ': 2,3' dianyhyd
Ride (hereinafter sometimes referred to as “DFAIII”) is an indigestible oligosaccharide having a unique structure in which the reducing ends of two fructose molecules are cyclically linked to other hydroxyl groups other than the fructose reducing ends. . As a physiological function, it has been confirmed in rats and humans that it has a high function of promoting mineral absorption in the small and large intestines. In addition, it has non-cariogenic properties, low calories, and does not affect blood sugar levels and insulin levels, and is used as a functional sugar (Non-patent Document 1 Journal of Sugar Technology Research, 51, 27-32 ( 2003) “Functionality of the new oligosaccharide DFAIII”), (Non-patent document 2 Published by the Confectionery Technology Center, 2004, p. 1-16. “Recommended by Food Industry Promotion Section, General Food Bureau, Ministry of Agriculture, Forestry and Fisheries” Material Utilization Technology Series 14: Difructose Anhydride III (Twin Tose)), (Non-patent Document 3: Functionality and Application of New Oligosaccharide “Twin Tose” by Kyoko Tomita, Development of Functional Carbohydrate Material and Application to Food P.179-187 (2005).) CMC Publishing).
このDFAIIIが最初に報告されたのは1929年であり、イヌリンから硫酸処理によりフラクトースを生成する過程で、副生物として得られ単離されている。工業的にはチコリー(Cichorium intybus)やキクイモ(Helianthus tuberosus L.)の根から、イヌリンを抽出し、Arthrobactor Sp.由来のフラクシルトランスフェラーゼ(E.C 2.4.1.93)を使った酵素法によって製造されている(非特許文献4 J. Ferment. Bioeng., 72:258-261 (1991)「 Yokota, A., Hirayama, S., Enomoto, K., Miura, Y., Takao, S., Tomita, F., Production of inulin fructotransferase (depolymerizing) by Arthrobacter sp. H65-7 and preparation of DFAIII from inulin by the enzyme.」)(非特許文献5 J. Ferment. Bioeng., 72: 262-265「Yokota, A., Enomoto, K., Tomita, F., Purification and properties of an inulin fructotransferase (depolymerizing) by Arthrobacter sp. H65-7.」)。(特許文献9(特開昭62−275694号公報 アースロバクター・グロビフォルミスに属する微生物又はその産生する酵素をイヌリン含有植物抽出液に作用させてDFAIIIを製造する方法) This DFAIII was first reported in 1929 and was obtained and isolated as a by-product in the process of producing fructose from inulin by sulfuric acid treatment. Industrially, inulin is extracted from the roots of chicory (Cichorium intybus) and Jerusalem artichoke (Helianthus tuberosus L.), and is produced by an enzymatic method using Arthrobactor Sp.-derived frucyltransferase (EC 2.4.1.93). (Non-Patent Document 4 J. Ferment. Bioeng., 72: 258-261 (1991) "Yokota, A., Hirayama, S., Enomoto, K., Miura, Y., Takao, S., Tomita, F. , Production of inulin fructotransferase (depolymerizing) by Arthrobacter sp. H65-7 and preparation of DFAIII from inulin by the enzyme. ”(Non-patent document 5 J. Ferment. Bioeng., 72: 262-265 Enomoto, K., Tomita, F., Purification and properties of an insulin fructotransferase (depolymerizing) by Arthrobacter sp. H65-7 "). (Patent Document 9 (Japanese Patent Application Laid-Open No. Sho 62-275694) A method of producing DFAIII by allowing a microorganism belonging to Arthrobacter globiformis or an enzyme produced therein to act on an inulin-containing plant extract)
本発明は、酵素法によらないダイフラクトースアンハイドライドIII(DFAIII)を製造する方法の開発することを目的とするものである。 An object of the present invention is to develop a method for producing difructose anhydride III (DFAIII) which is not based on an enzymatic method.
本発明は、ユリ科あるいはキク科に属する植物を高温加熱することによって、ダイフラクトースアンハイドライドIIIを生成し、ダイフラクトースアンハイドライドIIIを高含有する抽出エキス及びダイフラクトースアンハイドライドIIIを製造する方法である。 The present invention is a method for producing difructose anhydride III by heating a plant belonging to the family Liliaceae or Asteraceae at a high temperature, and producing an extract containing a high content of difructose anhydride III and difructose anhydride III. is there.
本発明の主な構成は次のとおりである。
(1)エシャロット(Allium ascalonicum)、ニンニク(Allium sativum)、ゴボウ(Arctium lappa L. )、アーティチョーク(Cynara scolymus)のいずれかを150〜250℃の温度で15分間以上ロースト処理し、水を添加し、クエン酸を添加せず加熱して熱水抽出することによって、ダイフラクトースアンハイドライドIIIを生成する方法。
The main configuration of the present invention is as follows.
(1) shallots (Allium ascalonicum), garlic (Allium sativum), burdock (Arctium lappa L.), roasted treated either at least 15 minutes at a temperature of 0.99 to 250 DEG ° C. artichoke (Cynara scolymus), water was added A method of producing difructose anhydride III by heating and extracting with hot water without adding citric acid .
ユリ科あるいはキク科植物を原料として、酵素法によらない加熱手段を施すことによりダイフラクトースアンハイドライドIIIを生成する方法を提供できる。ダイフラクトースアンハイドライドIIIを高含有するユリ科あるいはキク科植物抽出エキス及び含有食品、含有飼料を提供する。 A method for producing difructose anhydride III can be provided by using a lily family or asteraceae plant as a raw material and applying a heating means not based on an enzymatic method. A lilyaceae or asteraceae plant extract containing a high content of difructose anhydride III, a food containing it, and a feed containing it.
[概要]
難消化性オリゴ糖であるdifructose anhydride III (DFAIII:di-D-fructo-furanose 1,2’:2,3’ dianhydride)は、工業的にはチコリーの根からイヌリンを抽出し、さらにこれを酵素処理することによって製造されている。本発明は、イヌリンを含む食材であるニンニクを高温焙煎処理(ロースト処理)し、これを熱水抽出して得たエキスをモードの異なる3種類のHPLC分析にかけ、その結果、DFAIIIを定性・定量することができた。
このロースト処理によるニンニク抽出エキス中のDFAIII含有率は、処理時間と共に増加し、60分でエキス中の固形分あたり10%(W/W)近くにまでなる。一方、処理温度には適温があり、100℃以下ではDFAIIIは生成せず、150℃以上で生成が認められ、200℃の処理でニンニク抽出エキス中のDFAIIIは最も多く含まれ、それ以上の温度での処理は、逆にDFAIII含有率は減少する結果が示された。したがって、DFAIIIの生成温度は150℃以上であって、200℃付近が最も好ましく、300℃では炭化が激しくなるので実用的ではない。
[Overview]
Difuructose anhydride III (DFAIII: di-D-fructo-furanose 1,2 ': 2,3' dianhydride), an indigestible oligosaccharide, industrially extracts inulin from chicory roots, Manufactured by processing. The present invention is a high-temperature roasting treatment (roasting treatment) of garlic, which is an ingredient containing inulin, and the extract obtained by hot water extraction is subjected to three types of HPLC analysis with different modes. Quantification was possible.
The DFAIII content in the garlic extract by this roasting treatment increases with the treatment time, and reaches nearly 10% (W / W) per solid in the extract in 60 minutes. On the other hand, there is an appropriate temperature for the treatment, DFAIII is not produced at 100 ° C or lower, the production is observed at 150 ° C or higher, and the DFAIII in the garlic extract is most contained in the treatment at 200 ° C. On the other hand, the treatment with was shown that the DFAIII content decreased. Therefore, the production temperature of DFA III is 150 ° C. or higher, and is most preferably around 200 ° C., and carbonization becomes severe at 300 ° C., which is not practical.
本発明で提供できる植物は、ユリ科の植物であるタマネギ(Allium cepa)、ニンニク(Allium sativum)、ネギ(Allium fistulosum)、エシャロット(Allium ascalonicum)等、キク科植物であるゴボウ(Arctium lappa L.)、アーティチョーク(Cynara scolymus)、チコリー(Cichorium intybus;葉)等である。特に、ニンニク、エシャロット、アーティチョーク、ゴボウの抽出エキスには1%以上である3%以上のDFAIIIを高含有している。特に、ニンニクでは9%近い含有量を確認した。
その他身近に入手できた素材では、リンゴ(Malus pumila var. domestica)、バナナ(Musa acuminata)を加熱処理した抽出エキスにDFAの存在が確認できた。
その他、ニンジン(Daucus carota L.)(セリ科)、ジャガイモ(Solanum tuberosum L.)(ナス科)、ショウガ、(Zingiber officinale)(ショウガ科)、ミョウガ(Zingiber mioga Zingiber)(ショウガ科)、カブ(Brassica rapa)(アブラナ科)、ダイコン(Raphanus sativus L. )(アブラナ科)、サトイモ(Colocasia esculenta Schott )(サトイモ科)、サツマイモ(Ipomoea batatas L.)(ヒルガオ科)、ナガイモ(Dioscorea batatas)(ヤマイモ科)、レンコン(Nelumbo nucifera )(ハス科)、ビーツ(Beta vulgaris )(アカザ科)、カボチャ(Cucurbita maxima)(ウリ科)、トマト(Lycopersicon esculentum Mill.)(ナス科)も抽出試験をしたがDFAIIIの存在は確認できなかった。
Plants that can be provided by the present invention include lilies of onion (Allium cepa), garlic (Allium sativum), leeks (Allium fistulosum), shallot (Allium ascalonicum), and other asteraceae burdock (Arctium lappa L.). ), Artichoke (Cynara scolymus), chicory (Cichorium intybus; leaf) and the like. In particular, the extract of garlic, shallot, artichoke and burdock contains a high content of 3% or more DFAIII, which is 1% or more. In particular, the content of garlic was confirmed to be close to 9%.
Among other materials that were available to the public, the presence of DFA could be confirmed in extracts extracted from heat-treated apples (Malus pumila var. Domestica) and bananas (Musa acuminata).
In addition, carrot (Daucus carota L.) (Seriaceae), potato (Solanum tuberosum L.) (Solanum), ginger, (Zingiber officinale) (Ginger family), ginger (Zingiber mioga Zingiber), turnip (Ginger family) Brassica rapa) (Brassicaceae), Japanese radish (Raphanus sativus L.) (Brassicaceae), taro (Colocasia esculenta Schott) (Araceae), sweet potato (Ipomoea batatas L.) (Convolvulaceae), Chinese yam (Dioscorea batatas) ), Lotus root (Nelumbo nucifera) (Lotusaceae), beet (Beta vulgaris) (Rubiaceae), pumpkin (Cucurbita maxima) (Cucurbitaceae), tomato (Lycopersicon esculentum Mill.) (Solanum) The presence of DFAIII could not be confirmed.
[製法]
対象植物を細かく刻み、100℃以上の温度で20分以上加熱ロースト処理し、100℃で熱水抽出することにより、DFAIIIを生成した熱水抽出液を得ることができる。
加熱温度は、250℃では植物の炭化が激しくエキスの抽出には不向きである。200℃でも60分以上加熱すると炭化が進み抽出には不向きである。対象植物が生状体である場合は、軽く脱水処理することが可能である。脱水処理は、例えば、天日乾燥や電子レンジを使用することができる。
熱水抽出は、ロースト処理を施した植物を10倍量の精製水を添加し、100℃で60分間熱水抽出する。これをろ過して抽出エキスを得ることができる。ろ過条件は、ろ紙でろ過し、そのろ液をディスポーザブル0.45μm,0.22μmフィルター(DISMIC-25cs Cellulose Acetate 0.45μm, 0.22μm、ADVANTEC)で、段階的にろ過を行って抽出エキスとすることができる。この抽出エキスは、-80℃のフリーザーで凍結させた後、凍結乾燥した。
[Production method]
The hot water extract which produced | generated DFAIII can be obtained by chopping a target plant finely, carrying out the heating roast process for 20 minutes or more at the temperature of 100 degreeC or more, and extracting with hot water at 100 degreeC.
When the heating temperature is 250 ° C., the carbonization of the plant is severe and it is not suitable for extraction of the extract. When heated at 200 ° C. for 60 minutes or longer, carbonization proceeds and is not suitable for extraction. When the target plant is a living body, it can be lightly dehydrated. For the dehydration treatment, for example, sun drying or a microwave oven can be used.
In hot water extraction, 10 times the amount of purified water is added to the roasted plant, and hot water extraction is performed at 100 ° C. for 60 minutes. This can be filtered to obtain an extract. Filtration conditions are filtered through filter paper, and the filtrate can be extracted into an extract by stepwise filtration with a disposable 0.45μm, 0.22μm filter (DISMIC-25cs Cellulose Acetate 0.45μm, 0.22μm, ADVANTEC). . This extract was frozen in a freezer at −80 ° C. and then freeze-dried.
[DFAIII確認試験]
(1)装置及び測定条件
1)HPLC分析条件
DFAIII標準品のサンプルを準備し、0.005%DFAIII溶液を定性実験に使用した。
熱水抽出エキスを凍結乾燥で濃縮された抽出エキスを精製水に溶かしてHPLCのサンプルとし、以下の条件でHPLCを行った。
HPLC装置はESA,Inc.製のクーロアレイシステム(ポンプ;Model 582 Solvent Delivery System2台、荷電化粒子検出器;Corona CADクーロメトリック型多電極式電気化学検出器クーロアレイ16チャンネル、オートサンプラー;Model 540、カラムオーブン;MODEL 502 (FLOM社)・テンパレーチャーモジュール(ESA社))にインテグレータとしてクーロアレイオペレーションソフトVer2.0を接続したものを用い、以下の条件で測定した。
カラム;Shodex SUGAR SZ5532(6.0mmID×150mm、昭和電工(株)製)、移動層;75% CH3CN、流速;0.8 mL/min、カラム温度;40℃、検出器用窒素ガス流速;1.53mL/min、ガス圧:35〜36psi、注入量;10μL。以下この分析条件をHPLC条件−Aとする。
[DFAIII confirmation test]
(1) Equipment and measurement conditions 1) HPLC analysis conditions
Samples of DFA III standard were prepared and 0.005% DFA III solution was used for qualitative experiments.
The extract extracted by concentrating the hot water extract extract by freeze-drying was dissolved in purified water to prepare a HPLC sample, and the HPLC was performed under the following conditions.
The HPLC system is a coulo array system (pump; Model 582 Solvent Delivery System 2 units, manufactured by ESA, Inc., charged particle detector; Corona CAD coulometric multi-electrode electrochemical detector 16 channel, auto sampler; Model 540, A column oven; MODEL 502 (FLOM) / temperature module (ESA)) connected with Couloarray operation software Ver2.0 as an integrator was measured under the following conditions.
Column: Shodex SUGAR SZ5532 (6.0 mm ID × 150 mm, manufactured by Showa Denko KK), moving bed: 75% CH3CN, flow rate: 0.8 mL / min, column temperature: 40 ° C., nitrogen gas flow rate for detector: 1.53 mL / min, Gas pressure: 35-36 psi, injection volume: 10 μL. Hereinafter, this analysis condition is referred to as HPLC condition-A.
2)定性分析
HPLC条件−Aで得られたピークがDFAIIIであることを確認するために、2回の異なるHPLC条件を使って分取と定性分析を行った。まず、以下のHPLC条件で分取を行った。
分取用のHPLC装置として(ポンプ;LC-10ADVP (島津製作所) 2台、検出器;RI-101 (昭和電工)、オートサンプラー;AS-8020 (東ソー)、カラムオーブン;CO-8020(東ソー)にインテグレータとしてSMC21(資生堂)を接続したものを使い、以下の条件で測定した。
カラム; YMC Hydrosphere C18 S-5(4.6mmID×150mmL、(株)ワイエムシィ製)、ガードカラム;YMC Hydrosphere C18 S-5(4.6mmID×150mmL、(株)ワイエムシィ製)、移動層;水、流速;1.0 mL/min、カラム温度;40℃、注入量;5μL
DFAIII標準品と同じリテンションタイム(3.0分)にピークがある画分を分取し、この分取液をまとめて濃縮乾固した後、水にて再溶解し、定性分析用に用いた。
定性分析として、以下の条件のHPLCにかけた。
HPLC装置としては(ポンプ;AGP-1(ダイオネクス社) 2台、検出器;PED (ダイオネクス社)、オートサンプラー;AS-8020 (東ソー))にインテグレータとしてSMC21(資生堂)を接続したものを使い、以下の条件で測定した。
カラム;Dionex, CarboPac PA1(4.0mmID×250mmL、日本ダイオネクス(株))、ガードカラム;Dionex, CarboPac PA1 Guard(4.0mmID×50mmL、日本ダイオネクス(株))、移動層A:100 mM NaOH/20 mM 酢酸ナトリウム、移動層B:100 mM NaOH/60 mM 酢酸ナトリウム、グラジエント 0〜100%B in 20 min、流速;1.0 mL/min、カラム温度;室温、注入量;20μL、測定電位(E1); +0.05V (0.00〜0.40s)、酸化電位(E2); +0.75V (0.41〜0.61s)、還元電位(E3); -0.15V (0.62〜1.02s)
2) Qualitative analysis
In order to confirm that the peak obtained under HPLC condition-A was DFAIII, preparative and qualitative analysis was performed using two different HPLC conditions. First, fractionation was performed under the following HPLC conditions.
As a preparative HPLC system (pump; LC-10ADVP (Shimadzu Corporation) 2 units, detector; RI-101 (Showa Denko), autosampler; AS-8020 (Tosoh), column oven; CO-8020 (Tosoh)) Using an SMC21 (Shiseido) connected as an integrator, measurement was performed under the following conditions.
Column: YMC Hydrosphere C18 S-5 (4.6 mm ID × 150 mmL, manufactured by YMC), guard column; YMC Hydrosphere C18 S-5 (4.6 mm ID × 150 mmL, manufactured by YMC), moving bed: water, flow rate; 1.0 mL / min, column temperature; 40 ° C, injection volume: 5 μL
Fractions having a peak at the same retention time (3.0 minutes) as the DFA III standard product were collected, and the fractions were collected, concentrated to dryness, redissolved in water, and used for qualitative analysis.
As a qualitative analysis, it was subjected to HPLC under the following conditions.
As an HPLC device, a pump (AGP-1 (Dionex) 2 units, detector; PED (Dionex), autosampler: AS-8020 (Tosoh)) connected to an SMC21 (Shiseido) as an integrator, Measurement was performed under the following conditions.
Column: Dionex, CarboPac PA1 (4.0mmID × 250mmL, Nippon Dionex), guard column; Dionex, CarboPac PA1 Guard (4.0mmID × 50mmL, Nippon Dionex), moving bed A: 100 mM NaOH / 20 mM Sodium acetate, moving bed B: 100 mM NaOH / 60 mM sodium acetate, gradient 0-100% B in 20 min, flow rate; 1.0 mL / min, column temperature; room temperature, injection volume; 20 μL, measurement potential (E1); 0.05V (0.00 to 0.40s), oxidation potential (E2); + 0.75V (0.41 to 0.61s), reduction potential (E3); -0.15V (0.62 to 1.02s)
2)定量方法;
試験溶液は、上記のHPLC条件−Aを使って分析し、定量を行った。試料中のDFAIII含量は、クロマトグラムのピークのリテンションタイムにより同定し、以下の式を使って求めた。
「ローストされた食品の抽出エキス中のDFAIII含有率」(W/W%)=(A/1000)/B*C*100
A: 検線から求めた試験溶液中のDFAIIIの濃度(μg/mL)
B: 抽出エキス採取量(mg)
C: サンプル希釈率
2) Quantitative method;
The test solution was analyzed and quantified using the above HPLC condition-A. The DFAIII content in the sample was identified by the retention time of the chromatogram peak and was determined using the following formula.
“DFAIII content in the extract of roasted food” (W / W%) = (A / 1000) / B * C * 100
A: DFAIII concentration (μg / mL) in the test solution obtained from the calibration
B: Extracted extract amount (mg)
C: Sample dilution rate
(2)HPLCによる定性分析結果
対象植物としてニンニクを用いた分析結果は次とおりである。
HPLC条件−Aでは、DFAIII標準品のリテンションタイムは、5.46分であった。
ロースト処理されたニンニク抽出エキスのHPLCパターンを比較したところ、同じく5.46分にピークが確認された。また、構造異性体であるDFAIV標準品のピークのリテンションタイムを確認したところ、DFAIIIの標準品と大きく異なっていた。
この、分析条件−Aで使用した、ローストニンニクエキスと同じサンプルを分取し、HPLC条件−Bで分析した。未分取のニンニクエキスサンプルからも分取して得たサンプルからも、DFAIII標準品のリテンションタイムと同じ位置(8.4-8.5分)に、ピークが確認された。分配・吸着+配位子交換モードで分離するShodex SUGAR SZ5532、逆相モードであるYMC Hydrosphere C18 S-5、陰イオン交換モードのDionex, CarboPac PA1といった3本の分離モードが異なるカラムで、DFAIII標準品のリテンションタイムと同じ位置にピークが確認されたことから、このローストニンニクのサンプルには、DFAIIIが含まれていることが明らかになった。
同様にして、他の植物についても、分析を行いDFAIIIの生成の有無を確認した。
(2) Qualitative analysis results by HPLC The analysis results using garlic as the target plant are as follows.
Under HPLC condition-A, the retention time of the DFA III standard product was 5.46 minutes.
When the HPLC patterns of the roasted garlic extract were compared, a peak was also confirmed at 5.46 minutes. Moreover, when the retention time of the peak of the DFAIV standard product, which is a structural isomer, was confirmed, it was significantly different from the DFAIII standard product.
The same sample as the roasted garlic extract used under this analysis condition-A was collected and analyzed under HPLC condition-B. A peak was confirmed at the same position (8.4-8.5 minutes) as the retention time of the DFA III standard product from the sample obtained by fractionating from the unprepared garlic extract sample. DFAIII standard with three different separation modes: Shodex SUGAR SZ5532, which separates in partitioning / adsorption + ligand exchange mode, YMC Hydrosphere C18 S-5 in reverse phase mode, Dionex, CarboPac PA1 in anion exchange mode As a peak was confirmed at the same position as the product retention time, it became clear that this roasted garlic sample contained DFAIII.
Similarly, other plants were also analyzed to confirm the presence or absence of DFAIII production.
[DFAIIIの利用]
本発明で得られるDFAIIIを含有する植物エキスは、DFAIIIの通常用途に使用することができる。特に、本出願人が既に提案したDFAIIIの作用効果を発揮する剤及び食品に添加して使用することができる。
例えば、カルシウム吸収促進作用(特開2006-241057)、ナトリウム及び/又はカリウムの排泄促進作用(特開2006-104103)、速崩壊性固形製剤(特開2006-083141)、経皮吸収促進剤(特開2006-036656)、コーヒー添加剤(特開2006-006177)(特開2006-006176)、カルシウム配合組飲料添加剤(特開2006-006175)、ヨーグルト食品添加剤(特開2006-006174)、家畜動物用飼料添加剤(特開2004-329110)、ミネラル吸収亢進剤(特開2004-149427)、便通改善剤(特開2004-137194)、骨形成促進用経口剤(特開2004−161619)、う蝕誘発抑制剤(特開2004−284985)等である。
[Use of DFAIII]
The plant extract containing DFAIII obtained in the present invention can be used for normal use of DFAIII. In particular, it can be used by being added to an agent and food that exerts the action and effect of DFAIII already proposed by the present applicant.
For example, calcium absorption promoting action (JP 2006-241057), sodium and / or potassium excretion promoting action (JP 2006-104103), fast disintegrating solid preparation (JP 2006-083141), transdermal absorption enhancer ( JP 2006-036656), coffee additive (JP 2006-006177) (JP 2006-006176), calcium-containing beverage additive (JP 2006-006175), yogurt food additive (JP 2006-006174) Feed additive for livestock animals (JP 2004-329110), mineral absorption enhancer (JP 2004-149427), bowel movement improving agent (JP 2004-137194), oral agent for promoting bone formation (JP 2004-161619) ), Caries induction inhibitor (Japanese Patent Application Laid-Open No. 2004-284985) and the like.
[ニンニクの例]
1.抽出処理
1)野菜のロースト処理
市販の購入したニンニク355gをスライスして細かく刻み、ラップなしで電子レンジ(1000W)に3分程度かけて、軽く脱水した。室温になるまで放置した後、ステンレス製のバットに薄く並べ、オーブンで100〜250℃の温度で0〜60分間加熱ロースト処理し106gのローストニンニクを得た。
[Example of garlic]
1. Extraction treatment 1) Roasting of vegetables 355 g of commercially purchased garlic was sliced and finely chopped, and lightly dehydrated over a microwave oven (1000 W) for about 3 minutes without wrapping. After being allowed to stand at room temperature, it was thinly arranged on a stainless steel vat and roasted by heating in an oven at a temperature of 100 to 250 ° C. for 0 to 60 minutes to obtain 106 g of roasted garlic.
2)抽出処理
ロースト処理を施したニンニクを10倍量のMilli -Q水(日本ミリポア製により精製して得られた超純水)を添加し、100℃で60分間熱水抽出した。これをろ紙でろ過し、そのろ液をディスポーザブル0.45μm,0.22μmフィルター(DISMIC-25cs Cellulose Acetate 0.45μm, 0.22μm、ADVANTEC)で、段階的にろ過を行って抽出エキスを得た。この抽出エキスは、-80℃のフリーザーで凍結させた後、凍結乾燥器(FDU-2100 EYELA)で温度-81.2℃、気圧38Paの状態で2日程度凍結乾燥処理を行った。
2) Extraction treatment The roasted garlic was added with 10 times the amount of Milli-Q water (ultra pure water obtained by purification by Nihon Millipore) and extracted with hot water at 100 ° C for 60 minutes. This was filtered with a filter paper, and the filtrate was filtered stepwise with a disposable 0.45 μm, 0.22 μm filter (DISMIC-25cs Cellulose Acetate 0.45 μm, 0.22 μm, ADVANTEC) to obtain an extract extract. This extract was frozen in a freezer at −80 ° C., and then freeze-dried for about 2 days in a freeze dryer (FDU-2100 EYELA) at a temperature of −81.2 ° C. and a pressure of 38 Pa.
2.測定装置及び測定条件
1)HPLC分析条件
(DFAIII標準サンプル)
DFAIIIの標準品として、和光純薬工業(株)のdifructose anhydride IIIを用いた。標
準品のDFAIIIとDFAIVを適量(10mg)精秤し、そこに10mLのMilli-Q水を添加した(0.1%サンプル)。このDFAIV標準品のサンプルは、さらに0.05%に希釈し、定性実験に用いた。
また、DFAIII標準品のサンプルも順次希釈し、0.0005−0.01%(5-1000μg/mL)の濃度に調製し、定性・定量実験に用いた。
2. Measuring equipment and measuring conditions 1) HPLC analysis conditions (DFAIII standard sample)
As standards of DFA III, using difructose a nhydride III of Wako Pure Chemical Industries, Ltd.. Standard DFAIII and DFAIV were weighed appropriately (10 mg), and 10 mL of Milli-Q water was added thereto (0.1% sample). This DFAIV standard sample was further diluted to 0.05% and used for qualitative experiments.
In addition, DFAIII standard samples were also diluted in order and adjusted to a concentration of 0.0005-0.01% (5-1000 μg / mL) and used for qualitative and quantitative experiments.
凍結乾燥で濃縮されたニンニク抽出エキスを、10mg程度精秤し、これにMilli-Q水を1mL添加した。15分間超音波をかけて完全に溶解し、これをHPLCのサンプルとし、以下の条件でHPLCを行った。 About 10 mg of garlic extract concentrated by freeze-drying was precisely weighed, and 1 mL of Milli-Q water was added thereto. The solution was completely dissolved by applying ultrasonic waves for 15 minutes, and this was used as an HPLC sample. The HPLC was performed under the following conditions.
HPLC装置はESA,Inc.製のクーロアレイシステム(ポンプ;Model 582 Solvent Delivery System2台、荷電化粒子検出器;Corona CADクーロメトリック型多電極式電気化学検出器クーロアレイ16チャンネル、オートサンプラー;Model 540、カラムオーブン;MODEL 502 (FLOM社)・テンパレーチャーモジュール(ESA社))にインテグレータとしてクーロアレイオペレーションソフトVer2.0を接続したものを用い、以下の条件で測定した。以下この分析条件をHPLC条件−Aとする。
カラム;Shodex SUGAR SZ5532(6.0mmID×150mm、昭和電工(株)製)、移動層;75% CH3CN、流速;0.8 mL/min、カラム温度;40℃、検出器用窒素ガス流速;1.53mL/min、ガス圧:35〜36psi、注入量;10μL。
The HPLC system is a coulo array system (pump; Model 582 Solvent Delivery System 2 units, manufactured by ESA, Inc., charged particle detector; Corona CAD coulometric multi-electrode electrochemical detector 16 channel, auto sampler; Model 540, A column oven; MODEL 502 (FLOM) / temperature module (ESA)) connected with Couloarray operation software Ver2.0 as an integrator was measured under the following conditions. Hereinafter, this analysis condition is referred to as HPLC condition-A.
Column: Shodex SUGAR SZ5532 (6.0 mm ID × 150 mm, manufactured by Showa Denko KK), moving bed: 75% CH3CN, flow rate: 0.8 mL / min, column temperature: 40 ° C., nitrogen gas flow rate for detector: 1.53 mL / min, Gas pressure: 35-36 psi, injection volume: 10 μL.
2)定性分析
HPLC条件−Aで得られたピークがDFAIIIであることを確認するために、2回の異なるHPLC条件を使って分取と定性分析を行った。まず、以下のHPLC条件で分取を行った。
分取用のHPLC装置として(ポンプ;LC-10ADVP (島津製作所) 2台、検出器;RI-101 (昭和電工)、オートサンプラー;AS-8020 (東ソー)、カラムオーブン;CO-8020(東ソー)にインテグレータとしてSMC21(資生堂)を接続したものを使い、以下の条件で測定した。以下この分析条件をHPLC条件−Bとする。
カラム; YMC Hydrosphere C18 S-5(4.6mmID×150mmL、(株)ワイエムシィ製)、ガードカラム;YMC Hydrosphere C18 S-5(4.6mmID×150mmL、(株)ワイエムシィ製)、移動層;水、流速;1.0 mL/min、カラム温度;40℃、注入量;5μL
DFAIII標準品と同じリテンションタイム(3.0分)にピークがある画分を分取し、この分取液をまとめて濃縮乾固した後、水にて再溶解し、定性分析用に用いた。
定性分析として、以下の条件のHPLCにかけた。
HPLC装置としては(ポンプ;AGP-1(ダイオネクス社) 2台、検出器;PED (ダイオネクス社)、オートサンプラー;AS-8020 (東ソー))にインテグレータとしてSMC21(資生堂)を接続したものを使い、以下の条件で測定した。
カラム;Dionex, CarboPac PA1(4.0mmID×250mmL、日本ダイオネクス(株))、ガードカラム;Dionex, CarboPac PA1 Guard(日本ダイオネクス(株))、移動層A;1N NaOH、移動層B; 1M NaOAc (%)、移動層C;水、グラジェント条件;10→10%A,2→6%B,88→84%C(0→20分)、10→10%A,6→10%B,84→80%C(20.1→30分)、10→10%A,10→2%B,80→88%C(30.1→35分)、流速;1.0 mL/min、カラム温度;室温、注入量;20μL、測定電位(E1); +0.05V (0.00〜0.40s)、酸化電位(E2); +0.75V (0.41〜0.61s)、還元電位(E3); -0.15V (0.62〜1.02s)
2) Qualitative analysis
In order to confirm that the peak obtained under HPLC condition-A was DFAIII, preparative and qualitative analysis was performed using two different HPLC conditions. First, fractionation was performed under the following HPLC conditions.
As a preparative HPLC system (pump; LC-10ADVP (Shimadzu Corporation) 2 units, detector; RI-101 (Showa Denko), autosampler; AS-8020 (Tosoh), column oven; CO-8020 (Tosoh)) In addition, an SMC21 (Shiseido) connected as an integrator was measured under the following conditions, and this analytical condition is hereinafter referred to as HPLC condition-B.
Column: YMC Hydrosphere C18 S-5 (4.6 mm ID × 150 mmL, manufactured by YMC), guard column; YMC Hydrosphere C18 S-5 (4.6 mm ID × 150 mmL, manufactured by YMC), moving bed: water, flow rate; 1.0 mL / min, column temperature; 40 ° C, injection volume: 5 μL
Fractions having a peak at the same retention time (3.0 minutes) as the DFA III standard product were collected, and the fractions were collected, concentrated to dryness, redissolved in water, and used for qualitative analysis.
As a qualitative analysis, it was subjected to HPLC under the following conditions.
As an HPLC device, a pump (AGP-1 (Dionex) 2 units, detector; PED (Dionex), autosampler: AS-8020 (Tosoh)) connected to an SMC21 (Shiseido) as an integrator, Measurement was performed under the following conditions.
Column: Dionex, CarboPac PA1 (4.0mmID × 250mmL, Nippon Dionex Co., Ltd.), guard column; Dionex, CarboPac PA1 Guard (Nippon Dionex Co., Ltd.), moving layer A; 1N NaOH, moving layer B; 1M NaOAc (% ), Moving bed C; water, gradient conditions: 10 → 10% A, 2 → 6% B, 88 → 84% C (0 → 20 min), 10 → 10% A, 6 → 10% B, 84 → 80% C (20.1 → 30 min), 10 → 10% A, 10 → 2% B, 80 → 88% C (30.1 → 35 min), flow rate: 1.0 mL / min, column temperature; room temperature, injection volume: 20 μL , Measured potential (E1); + 0.05V (0.00 to 0.40s), oxidation potential (E2); + 0.75V (0.41 to 0.61s), reduction potential (E3); -0.15V (0.62 to 1.02s)
3)定量方法;
試験溶液は、上記のHPLC条件−Aを使って分析し、定量を行った。試料中のDFAIII含量は、クロマトグラムのピークのリテンションタイムにより同定し、以下の式を使って求めた。
「ローストされた食品の抽出エキス中のDFAIII含有率」(W/W%)=(A/1000)/B*C*100
A: 検線から求めた試験溶液中のDFAIIIの濃度(μg/mL)
B: 抽出エキス採取量(mg)
C: サンプル希釈率
3) Quantitative method;
The test solution was analyzed and quantified using the above HPLC condition-A. The DFAIII content in the sample was identified by the retention time of the chromatogram peak and was determined using the following formula.
“DFAIII content in the extract of roasted food” (W / W%) = (A / 1000) / B * C * 100
A: DFAIII concentration (μg / mL) in the test solution obtained from the calibration
B: Extracted extract amount (mg)
C: Sample dilution rate
3.結果および考察
(1)HPLCによる定性分析
HPLC条件−Aでは、DFAIII標準品のリテンションタイムは、5.46分であった(図1)。ロースト処理されたニンニク抽出エキスのHPLCパターンを比較したところ、同じく5.46分にピークが確認された(図2)。また、構造異性体であるDFAIV標準品のピークのリテンションタイムを確認したところ、DFAIIIの標準品と大きく異なっていた。
この、分析条件−Aで使用したローストニンニクエキスと同じサンプルを分取し、HPLC条件−Bで分析した。未分取のニンニクエキスサンプルからも分取して得たサンプルからも、DFAIII標準品のリテンションタイムと同じ位置(8.4-8.5分)に、ピークが確認された(図3)。分配・吸着+配位子交換モードで分離するShodex SUGAR SZ5532、逆相モードであるYMC Hydrosphere C18 S-5、陰イオン交換モードのDionex, CarboPac PA1といった3本の分離モードが異なるカラムで、DFAIII標準品のリテンションタイムと同じ位置にピークが確認されたことから、このローストニンニクのサンプルには、DFAIIIが含まれていることが明らかになった。
3. Results and discussion (1) Qualitative analysis by HPLC
Under HPLC condition-A, the retention time of the DFA III standard product was 5.46 minutes (FIG. 1). When the HPLC patterns of the roasted garlic extract were compared, a peak was also confirmed at 5.46 minutes (FIG. 2). Moreover, when the retention time of the peak of the DFAIV standard product, which is a structural isomer, was confirmed, it was significantly different from the DFAIII standard product.
The same sample as the roasted garlic extract used in this analysis condition-A was collected and analyzed under HPLC condition-B. A peak was also confirmed from the sample obtained by fractionating from an unsorted garlic extract sample at the same position (8.4-8.5 min) as the retention time of the DFA III standard product (Fig. 3). DFAIII standard with three different separation modes: Shodex SUGAR SZ5532, which separates in partitioning / adsorption + ligand exchange mode, YMC Hydrosphere C18 S-5 in reverse phase mode, Dionex, CarboPac PA1 in anion exchange mode As a peak was confirmed at the same position as the product retention time, it became clear that this roasted garlic sample contained DFAIII.
(2)ロースト処理条件に伴うニンニク中のDFAIII含有率の変化
ニンニクのロースト処理温度を200℃に固定し、処理時間を0分、15分、20分、30分、45分、60分と変化させた。60分以上の処理ではサンプルの炭化が激しく、抽出に不向きであった。抽出されたエキスサンプルは、凍結乾燥させないスープサンプルとしてそのまま、HPLC 分析にかけた。標準品のDFAIII(0.0005−0.01%)を使って作成した検量線により、このスープサンプル中のDFAIII含有率を測定したところ、処理時間の増加に伴って、DFAIIIの含有率も増加した(表1、図4)。
表1及び図4から15分経過以降のロースト処理時間による検体の重量の減少率が10%程度であったことに対して、その抽出エキス中のDFAIII含有率は27倍も増加していることから、加熱乾燥に伴う重量減少によって、DFAIIIが増えたように見えるわけではなく、ロースト処理時間の増加に伴い、ニンニク中のDFAIII生成量が急激に増加していることが認められる。ロースト時間は20分以上、好ましくは30分以上、より好ましくは60分程度である。30分以上で2%以上、60分では約9%のDFAIII含有抽出エキスが得られた。
(2) Change in DFAIII content in garlic due to roasting treatment conditions Garlic roasting treatment temperature is fixed at 200 ° C, and treatment time is changed to 0, 15, 20, 30, 45, and 60 minutes. I let you. When the treatment was performed for 60 minutes or longer, the sample was severely carbonized and was not suitable for extraction. The extracted extract sample was directly subjected to HPLC analysis as a soup sample that was not lyophilized. When the DFAIII content in this soup sample was measured using a calibration curve prepared using the standard DFAIII (0.0005-0.01%), the DFAIII content increased with increasing treatment time (Table 1). , FIG. 4).
From Table 1 and FIG. 4, the DFAIII content in the extract increased by 27 times, whereas the decrease in the weight of the specimen due to the roasting time after 15 minutes was about 10%. From the results, it can be seen that DFAIII does not appear to increase due to the weight loss accompanying heat drying, and that the amount of DFAIII produced in garlic increases rapidly as the roasting time increases. The roasting time is 20 minutes or longer, preferably 30 minutes or longer, more preferably about 60 minutes. An extract containing DFA III containing 2% or more at 30 minutes or more and about 9% at 60 minutes was obtained.
ニンニクのロースト処理時間を60分に固定して、処理温度を、100℃、150℃、200℃、250℃と変化させ、スープサンプルをHPLC 分析にかけたところ、このスープサンプル中では、200℃で最も高いDFAIII含有率を示した(表2)。
表2から、DFAの生成は、100℃〜250℃、好ましくは150℃〜250℃、最適は200℃付近であると認められる。250℃でのDFAIII生成量の減少は、DFAIIIの加熱分解が促進されるか、二糖環状構造という特殊な構造を取れにくくなるためと推測している。また、250℃ではニンニクの炭化が進み熱水抽出には適さないことからも、上限となる。
The roasted garlic treatment time was fixed at 60 minutes, the treatment temperature was changed to 100 ° C, 150 ° C, 200 ° C, 250 ° C, and the soup sample was subjected to HPLC analysis. The highest DFAIII content was shown (Table 2).
From Table 2, it is recognized that the production of DFA is 100 ° C. to 250 ° C., preferably 150 ° C. to 250 ° C., and optimally around 200 ° C. The decrease in the amount of DFAIII produced at 250 ° C. is presumed to be because the thermal decomposition of DFAIII is promoted or it is difficult to take a special structure called a disaccharide cyclic structure. Moreover, since carbonization of garlic proceeds at 250 ° C. and is not suitable for hot water extraction, it becomes an upper limit.
[他の植物のDFAIII含有率]
実施例1の結果より、処理条件を200℃、60分として、次の植物の抽出エキスに含まれるDFAIIIを測定した。
抽出する食品試料として2006年7月〜9月に店頭で販売されていた、タマネギ(Allium cepa)、ニンニク(Allium sativum)、ゴボウ(Arctium lappa L.)、ニンジン(Daucus carota L.)、ジャガイモ(Solanum tuberosum L.)、ショウガ、(Zingiber officinale)、ミョウガ(Zingiber mioga Zingiber)、カブ(Brassica rapa)、ダイコン(Raphanus sativus L. )、サトイモ(Colocasia esculenta Schott )、サツマイモ(Ipomoea batatas L.)、ナガイモ(Dioscorea batatas)、レンコン(Nelumbo nucifera )、ビーツ(Beta vulgaris )、ネギ(Allium fistulosum)、エシャロット(Allium ascalonicum)アーティチョーク(Cynara scolymus)、チコリー(Cichorium intybus;葉)、カボチャ(Cucurbita maxima)、トマト(Lycopersicon esculentum Mill.)、リンゴ(Malus pumila var. domestica)、バナナ(Musa acuminata)を用いた。
[DFA III content of other plants]
From the results of Example 1, DFAIII contained in the extract of the next plant was measured at a treatment condition of 200 ° C. for 60 minutes.
Onion (Allium cepa), garlic (Allium sativum), burdock (Arctium lappa L.), carrot (Daucus carota L.), potato (which was sold in stores from July to September 2006 as food samples to extract Solanum tuberosum L.), ginger, (Zingiber officinale), ginger (Zingiber mioga Zingiber), turnip (Brassica rapa), radish (Raphanus sativus L.), taro (Colocasia esculenta Schott), sweet potato (Ipomoea batatas L.) (Dioscorea batatas), lotus root (Nelumbo nucifera), beets (Beta vulgaris), leek (Allium fistulosum), shallot (Allium ascalonicum) artichoke (Cynara scolymus), chicory (Cichorium intybus; leaf), pumpkin (Cucurbita max) Lycopersicon esculentum Mill.), Apple (Malus pumila var. Domestica), and banana (Musa acuminata) were used.
その計測結果を表3に示す。
高温加熱処理を行っていない食品素材からは、DFAIIIは検出されなかった。以上の結果から、ニンニク、ネギ、エシャロット、タマネギといったユリ科の野菜とゴボウ、アーティチョークなどのキク科の食品素材をロースト処理したものにDFAIIIが多量に含まれることが確認された。また、ローストされた果物類にも、DFAIIIが若干ではあるが含まれていることが示された。
このユリ科の鱗茎(タマネギ、エシャロット、ニンニク)、葉身(ネギ)、キク科植物の中でも直根(ゴボウ)、花托(アーティチョーク)といった肥大し、貯蔵部器官として働いている部位には含まれ、成長を続けている葉(チコリー)には含まれないことが確認された。このユリ科のニンニク、キク科のゴボウは、貯蔵多糖類としてイヌリンを含むことが知られており、その他の科の野菜ではイヌリンを貯蔵多糖として含まないことから、イヌリンのロースト処理がDFAIIIの生成に関わっていることが示唆される。
また、若干のDFAIIIが確認された果物は、イヌリンではなくフラクトースが多く含まれていることが知られている。さらに、今回の結果から、果物中の糖分の組成中でシュークロースの割合が高いバナナよりもフラクトースの割合が高いリンゴのほうが、DFAIII生成量が高いことが示された。その為、イヌリンのロースト処理による反応以外にも、フラクトースのみでの何らかの反応が、DFAIIIの生成に関与していることが推測された。
The measurement results are shown in Table 3.
DFAIII was not detected from food materials not subjected to high-temperature heat treatment. From the above results, it was confirmed that a large amount of DFAIII was contained in roasted lignins such as garlic, leeks, shallots, and onions and asteraceae such as burdock and artichokes. It was also shown that the roasted fruits contained a small amount of DFAIII.
These lily family bulbs (onions, shallots, garlic), leaf blades (onions), among the asteraceae plants are enlarged, such as straight roots (burdock), flower buds (artichokes), are included in the parts that act as storage organs It was confirmed that it was not included in the growing leaf (chicory). This lily family garlic and asteraceae burdock are known to contain inulin as a storage polysaccharide, and other family vegetables do not contain inulin as a storage polysaccharide, so roasting inulin produces DFAIII. It is suggested that they are involved.
Moreover, it is known that the fruit in which some DFAIII is confirmed contains a lot of fructose, not inulin. Furthermore, the results showed that apples with higher fructose content had higher DFAIII production than bananas with higher sucrose content in the sugar composition of fruits. Therefore, it was speculated that some reaction with only fructose was involved in the production of DFAIII in addition to the reaction by roasting of inulin.
Claims (1)
Shallots (Allium ascalonicum), garlic (Allium sativum), burdock (Arctium lappa L.), roasted treated either at least 15 minutes at a temperature of 0.99 to 250 DEG ° C. artichoke (Cynara scolymus), water was added, citric acid A method of producing difructose anhydride III by heating and extracting with hot water without addition of .
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