JP2019165728A - 農薬を含まない羅漢果抽出物およびその調製方法 - Google Patents
農薬を含まない羅漢果抽出物およびその調製方法 Download PDFInfo
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- JP2019165728A JP2019165728A JP2019072498A JP2019072498A JP2019165728A JP 2019165728 A JP2019165728 A JP 2019165728A JP 2019072498 A JP2019072498 A JP 2019072498A JP 2019072498 A JP2019072498 A JP 2019072498A JP 2019165728 A JP2019165728 A JP 2019165728A
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- Prior art keywords
- fruit extract
- activated carbon
- pesticide
- mogroside
- rahan fruit
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000284 extract Substances 0.000 title claims abstract description 216
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- 239000003765 sweetening agent Substances 0.000 claims abstract description 44
- 235000003599 food sweetener Nutrition 0.000 claims abstract description 43
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 38
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- 238000004062 sedimentation Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
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- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
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- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
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- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
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- 238000004809 thin layer chromatography Methods 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
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Abstract
Description
(I−1)農薬含有羅漢果抽出物を活性炭処理して農薬を除去する工程を有する、農薬不含羅漢果抽出物の調製方法であって、
上記活性炭処理で使用する活性炭が、ヨウ素吸着量が少なくとも1500mg/gである活性炭及びカラメル脱色能が少なくとも85%である活性炭よりなる群から選択されるいずれか少なくとも1つの活性炭であり、
当該活性炭の処理によるモグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドIからなる羅漢果配糖体の回収率が少なくとも70%である、上記調製方法。
(I−2)上記農薬不含羅漢果抽出物に含まれるモグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドIの総量が、当該農薬不含羅漢果抽出物100重量%あたり少なくとも33重量%である、(I−1)に記載する調製方法。
(I−3)農薬が、ジメトモルフ、トリアジメノール、テブコナゾール、ジフェノコナゾール、メタラキシルおよびメタラキシルMからなる群より選択される少なくとも1種、好ましくは2種以上、より好ましくは6種である、(I−1)または(I−2)に記載する調製方法。
なお、当該発明は上記(I−1)に記載する独立項の形式で、下記のように言い換えることができる。
「農薬を含有する羅漢果抽出物(農薬含有羅漢果抽出物)を活性炭処理して当該農薬を除去する工程を有する、当該農薬を含まない羅漢果抽出物(農薬不含羅漢果抽出物)の調製方法であって、
上記活性炭処理で使用する活性炭が、ヨウ素吸着量が少なくとも1500mg/gである活性炭及びカラメル脱色能が少なくとも85%である活性炭よりなる群から選択されるいずれか少なくとも1つの活性炭であり、 上記農薬がジメトモルフ、トリアジメノール、テブコナゾール、ジフェノコナゾール、メタラキシルおよびメタラキシルMからなる群より選択される少なくとも1種、好ましくは2種以上、より好ましくは6種類であり、
当該活性炭の処理によるモグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドIからなる羅漢果配糖体の回収率が少なくとも70%である、上記調製方法。」
(I−4)上記農薬不含羅漢果抽出物が、これを下記条件のHPLCに供した場合、当該HPLC分析で検出される保持時間16分付近のピークの面積が全ピークの総面積の3%以下である、(I−1)〜(I−3)のいずれかに記載する調製方法:
[HPLC条件]
カラム:Kaseisorb LC ODS2000(150mm×4.6mmI.D.)((株)東京化成工業製)移動相:アセトニトリルと水の混合液
0分→10分(イソクラティック):アセトニトリル20容量%、
10分→50分(リニアグラジエント):アセトニトリル20容量%→55容量%流速:1mL/分
カラム温度:40℃
検出器:UV 203nm。
(II-1)農薬を含まない羅漢果抽出物(農薬不含羅漢果抽出物)であって、
当該農薬不含羅漢果抽出物に含まれるモグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドIの総量が、農薬不含羅漢果抽出物100重量%あたり少なくとも33重量%であり、
下記条件のHPLC分析において保持時間16分付近に検出されるピークの面積が全ピークの総面積の3%以下である、上記農薬不含羅漢果抽出物:
[HPLC条件]
カラム:Kaseisorb LC ODS2000(150mm×4.6mmI.D.)((株)東京化成工業製)移動相:アセトニトリルと水の混合液
0分→10分(イソクラティック):アセトニトリル20容量%、
10分→50分(リニアグラジエント):アセトニトリル20容量%→55容量%流速:1mL/分
カラム温度:40℃
検出器:UV 203nm。
(II-2)上記HPLC分析において保持時間16分付近に検出されるピークが分子量358ダルトンの化合物のピークである、(II-1)に記載する農薬不含羅漢果抽出物。(II-3)上記農薬が、ジメトモルフ、トリアジメノール、テブコナゾール、ジフェノコナゾール、メタラキシルおよびメタラキシルMである(II-1)または(II-2)に記載する農薬不含羅漢果抽出物。なお、当該発明は上記(II-1)に記載する独立項の形式で、下記のように言い換えることができる。
「農薬を含まない羅漢果抽出物(農薬不含羅漢果抽出物)であって、
当該農薬不含羅漢果抽出物に含まれるモグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドIの総量が、農薬不含羅漢果抽出物100重量%あたり少なくとも33重量%であり、
上記農薬は少なくともジメトモルフ、トリアジメノール、テブコナゾール、ジフェノコナゾール、メタラキシルおよびメタラキシルMであり、
下記条件のHPLC分析において保持時間16分付近に検出されるピークの面積が全ピークの総面積の3%以下である、上記農薬不含羅漢果抽出物:
[HPLC条件]
カラム:Kaseisorb LC ODS2000(150mm×4.6mmI.D.)((株)東京化成工業製)移動相:アセトニトリルと水の混合液 0分→10分(イソクラティック):アセトニトリル20容量%、
10分→50分(リニアグラジエント):アセトニトリル20容量%→55容量%流速:1mL/分
カラム温度:40℃
検出器:UV 203nm。」
(II-4)(I-1)〜(I-4)のいずれか一項に記載する調製方法を用いて、農薬含有羅漢果抽出物から調製された(II-1)〜(II-3)のいずれか一項に記載する農薬不含羅漢果抽出物。
(III-1)(II-1)〜(II-4)のいずれか一項に記載する農薬不含羅漢果抽出物からなるか、または(II-1)〜(II-4)のいずれか一項に記載する農薬不含羅漢果抽出物及び補助甘味成分を含有する甘味料組成物。
(III-2)上記補助甘味成分が、単糖類、二糖類、オリゴ糖類、糖アルコール類、非糖質系甘味料、及び食物繊維類からなる群より選択される少なくとも1種である、(III-1)に記載する甘味料組成物。
(III-3)(III-1)または(III-2)に記載する甘味料組成物を含有する飲食物、医薬部外品、化粧品または医薬品。
本発明は農薬を含む羅漢果抽出物(農薬含有羅漢果抽出物)を活性炭処理して農薬を除去する工程を有することを特徴とする、農薬不含羅漢果抽出物の調製方法である。
また、抽出方法として超臨界抽出法または亜臨界抽出法を用いる場合は、抽出溶媒として二酸化炭素、及び亜酸化窒素を例示することができる。
なお、参考までに、上記6種類のうちジメトモルフ、テブコナゾール、ジフェノコナゾール、メタラキシル及びメタラキシルMのLogPow 値を下記に示す。
農薬含有羅漢果抽出物における農薬含有量は、上記農薬の個々の量として0.01ppm以上である。
活性炭のヨウ素吸着量の測定方法としては、「JIS K 1474:2014活性炭試験方法」の「7.1吸着性能」「7.1.2.2よう素吸着性能」で規定されている方法を挙げることができる。
ヨウ素カリウム25.0gを蒸留水30mLに溶解し、これにヨウ素約13gを加えて溶かし、蒸留水で1,000mLとして0.05mol/Lのヨウ素溶液を調製する。被験試料(活性炭)1.0gを共栓付三角フラスコに入れ、調製しておいたヨウ素溶液50mLを加え、アルミホイルで包む。室温(20〜30℃)で振盪機を用いて振盪した後、所定時間毎に取り出し、遠心分離用沈殿管50mLに移し入れ、遠心分離機を用いて3,000rpm、15分間で沈殿させる。この中から上澄液10mLを正確に取り、0.1mol/Lチオ硫酸ナトリウム溶液で滴定し、ヨウ素の黄色が薄くなったとき指示薬のでんぷん溶液(10g/L)1mLを加え、さらに滴定を続け、ヨウ素でんぷんの青色が消える時を終点とする。そして、残留しているヨウ素濃度(ヨウ素残留濃度)から供試炭のヨウ素吸着力を求める。
予め115±5℃の恒温乾燥器中で3時間乾燥し、デシケーター中で室温まで放冷した被験試料(活性炭)150mgに、カラメル試験液50mLを加え、室温(20〜30℃)で振盪機を用いて30分間振盪する。その後、濾紙でろ過する。始めのろ液20mLは捨てて、その後のろ液の430nmの吸光度を測定する。別に空試験として、カラメル試験液50mLについて、上記振盪以降の操作を同様に行う。ろ液の吸光度とカラメル試験液(空試験)の吸光度からカラメル脱色性能を求める。
なお、ここでカラメル試験液は、下記の方法によって調製したものを用いる。
デシケーターの中で24時間以上乾燥させたスクロース60gを500mL容量の三角フラスコに入れる。これに水240mL加えて室温(20〜30℃)で溶解し、硫酸(硫酸1:水4)25mLを加え、80±1℃に調節した水浴中に浸漬する。三角フラスコ内の溶液をかき混ぜながら80℃近くまで上昇させ、さらに30分間、80±1℃の状態に保つ。水浴から三角フラスコを取り出し、直ちに水酸化ナトリウム溶液(200g/L)50mLを加え、直ちに沸騰水浴中に三角フラスコを入れて15分間加熱する。三角フラスコを沸騰水浴中から取り出して、室温で一夜放置した後、硫酸(硫酸1:水10)又は水酸化ナトリウム溶液(100g/L)を加えてpH7.0±0.1に調製する。三角フラスコ内の溶液を、全量フラスコ500mLに移し入れ、水を500mLの標線まで加える。
斯くして調製したカラメル原液を、水で体積比1:20に薄めて30分間放置した後、光度計を用いて波長430nmの吸光度を測定する。下記の色度標準液の吸光度に一致するように、希釈割合を調製し、調製した溶液をカラメル試験液とする。
ニクロム酸カリウムをめのう乳鉢で砕き、105±5℃に調節した恒温乾燥器中で3〜4時間乾燥し、デシケーター中で放冷した後、その0.310gを量り取り、水を加えて溶かす。これを全量フラスコに移し入れ、水を標線まで加えて色度標準液とする。この溶液を光度計を用いて波長430nmの吸光度を測定する。
(1)カラムに必要量の粒状活性炭を充填し、脱イオン水をカラムの頂部から底部へ流し、活性炭微粉等を洗い流す。
(2)上記で調製した粒状活性炭充填カラムに、予め水を加えて5〜20w/vol%、より好ましくは5〜10w/vol%に調整した羅漢果抽出物水溶液を注入する。
(3)上記カラムに脱イオン水を注入し、流出する羅漢果抽出物を含む溶液を分画する。(4)上記で分画した各溶液について、薄層クロマトグラフィーまたはHPLC等を用いてモグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドIの有無を確認し、これらの羅漢果配糖体を含む画分をそれぞれ回収する。
(5)回収した各羅漢果配糖体を含む画分を一緒にして、農薬不含羅漢果配糖体とする。
・HPLC装置:Prominence LC-20AD((株)島津製作所製)
・LCカラム:Shodex Asahipak NH2-50 4E(250mm×4.6mm I.D.、(株)昭和電工製)
・LC条件
注入量 :20μL
カラム温度:40℃
移動相:74容量%アセトニトリル/26容量%水
流速:1.0 mL/分
検出波長:UV 203nm。
・LCカラム:Kaseisorb LC ODS 2000(150mm×4.6mm I.D.、(株)東京化成工業製)
・LC条件
注入量 :20μL
カラム温度:40℃
移動相:A相:水、B相:アセトニトリル
0→10分(イソクラティック):A相80容量%、B相20容量%
10→50分(リニアグラジエント):「A相80容量%、B相20容量%」→「A相45容量%、B相55容量%」
流速 :1.0 mL/分
検出波長:UV 203 nm。
また本発明において「農薬含有羅漢果抽出物から農薬を除去する」とは、ジメトモルフ、トリアジメノール、テブコナゾール、ジフェノコナゾール、メタラキシルおよびメタラキシルMからなる群より選択される少なくとも1種の農薬を含む羅漢果抽出物(農薬含有羅漢果抽出物)から当該農薬を除去して、羅漢果抽出物中に含まれる当該農薬の個々の量(残留濃度)を乾燥物換算で0.01ppm未満にすることを意味する。
・LC/MS装置:LCMS-2010EV((株)島津製作所製)
・LCカラム:Inertsil ODS-3(250mm×4.6mm,I.D.5μm、(株)ジーエルサイエンス製)
・LC条件
注入量 :30μL
カラム温度:40℃
移動相 :80容量%アセトニトリル/20容量%水
流速 :1.0mL/分
・MS条件
イオン化法 :APCI法、ポジティブモード
ネブライズガス流量 :2.5 L/分
APCIインターフェイス温度:350℃
CDL温度 :200℃
ヒートブロック温度 :300℃。
背景技術の欄に記載するように、モグロサイドV,モグロサイドIV,11−オキソ−モグロサイドVおよびシアメノサイドIからなる羅漢果配糖体の総量が全体、つまり農薬不含羅漢果抽出物の33重量%以上になるまで精製した羅漢果抽出物(高純度羅漢果配糖体)は、甘味の基本性能である、「後引き、しつこさ、くせ、渋味、刺激、すっきり感、まろやかさ、こく、苦み」のいずれの評価に対しても砂糖に極めて高い甘味質を有していることが知られている。
後述する実験例3に示すように、本発明の方法で調製される農薬不含羅漢果抽出物は、下記条件のHPLCに供した場合、当該HPLC分析で検出される保持時間16分付近のピーク(以下、「P16」という)の面積が全ピークの総面積の3%以下であることを特徴とする。
[HPLC条件]
カラム:Kaseisorb LC ODS2000(150mm×4.6mmI.D.)((株)東京化成工業製)移動相:アセトニトリルと水の混合液
0分→10分(イソクラティック):アセトニトリル20容量%、
10分→50分(リニアグラジエント):アセトニトリル20容量%→55容量%流速:1mL/分
カラム温度:40℃
検出器:UV 203nm。
ここで本発明が対象とする羅漢果抽出物は、下記(ロ)及び(ハ)の特徴を有する農薬を含まない羅漢果抽出物(農薬不含羅漢果抽出物)である。
(ロ)農薬不含羅漢果抽出物に含まれるモグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドIの総量が、農薬不含羅漢果抽出物100重量%あたり少なくとも33重量%である。
(ハ)下記条件のHPLC分析において保持時間16分付近に検出されるピークの面積が全ピークの総面積の3%以下である:
ここで、限定はされないが、保持時間16分付近とは、例えば保持時間15分から17分の間に存在することを示す。ピーク面積は、例えば、解析ソフトLabSolution((株)島津製作所)を使用することで求めることができる。
[HPLC条件]
カラム:Kaseisorb LC ODS2000(150mm×4.6mmI.D.)(東京化成工業株式会社製)移動相:アセトニトリルと水の混合液
0分→10分(イソクラティック):アセトニトリル20容量%、
10分→50分(リニアグラジエント):アセトニトリル20容量%→55容量%流速:1mL/分
カラム温度:40℃
検出器:UV 203nm。
本発明の甘味料組成物は、前述する農薬不含羅漢果抽出物からなるか、または当該農薬不含羅漢果抽出物に加えて補助甘味成分を含有するものである。
本発明の方法によって調製した羅漢果抽出物または本発明の羅漢果抽出物によれば、モグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドIからなるモグロサイド類(羅漢果配糖体)を高い収率で回収するとともに、農薬が選択的且つ効率的に除去できるだけでなく、羅漢果抽出物に含まれている特定の雑味成分の除去低減も可能となる。このため、従来の方法で調製される羅漢果抽出物と比べて、良好な甘味質を有する羅漢果抽出物を得ることができる。
羅漢果抽出物に含まれるモグロサイドV及びその他の羅漢果配糖体(モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドI)の定量は、高速液体クロマトグラフィー(HPLC)を用いて行った。使用した装置および条件は下記の通りである。
・LCカラム:Shodex Asahipak NH2-50 4E(250mm×4.6mm I.D.、(株)昭和電工製)
・LC条件
注入量 :20μL
カラム温度:40℃
移動相:74容量%アセトニトリル/26容量%水
流速:1.0 mL/分
検出波長:UV 203nm
・HPLC装置:Prominence LC-20AD((株)島津製作所製)
・LCカラム:Kaseisorb LC ODS 2000(150mm×4.6mm I.D.、(株)東京化成工業製)
・LC条件
注入量 :20μL
カラム温度:40℃
移動相:A相:水、B相:アセトニトリル
0→10分(イソクラティック):A相80容量%、B相20容量%
10→50分(リニアグラジエント):「A相80容量%、B相20容量%」→「A相45容量%、B相55容量%」
流速 :1.0 mL/分
検出波長:UV 203 nm。
(1)前処理
羅漢果抽出物に含まれる農薬の量を液体クロマトグラフィー/マススペクトロメトリー(LC/MS)で定量するに先立ち、羅漢果抽出物を下記手順で前処理し、得られた処理物を「LS/MS測定用試料」とする。
羅漢果抽出物に含まれる農薬(ジメトモルフ、トリアジメノール、テブコナゾール、ジフェノコナゾール、メタラキシルおよびメタラキシルM)の定量は、液体クロマトグラフィー/マススペクトロメトリー(LC/MS)により行う。使用する装置および条件は下記の通りである。なお、当該方法による各種農薬の定量限界値はいずれも0.01ppmである。
・LC/MS装置:LCMS-2010EV((株)島津製作所製)
・LCカラム:Inertsil ODS-3(250mm×4.6mm,I.D.5μm、(株)ジーエルサイエンス製)
・LC条件
注入量 :30μL
カラム温度:40℃
移動相 :80容量%アセトニトリル/20容量%水
流速 :1.0mL/分
・MS条件
イオン化法 :APCI法、ポジティブモード
ネブライズガス流量 :2.5 L/分
APCIインターフェイス温度:350℃
CDL温度 :200℃
ヒートブロック温度 :300℃。
農薬除去処理による農薬除去率は、下式(1)から求めることができる。
桂林莱茵生物科技股▲分▼有限公司より入手した羅漢果抽出物(Luohanguo Glucoside 40% yellow type)(以下、これを「原料羅漢果抽出物」ともいう)中に含まれる羅漢果配糖体(モグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドI)の含有量、及び農薬(ジメトモルフ、トリアジメノール、テブコナゾール、ジフェノコナゾール、メタラキシルおよびメタラキシルM)の含有量を、上記参考例1及び2に記載する方法に従って求めた。
結果を表3及び4に示す。なお、各表に記載する値は、いずれも原料羅漢果抽出物(乾燥物)に含まれる各成分の乾燥物換算値である。
(1)原料羅漢果抽出物(桂林莱茵生物科技股▲分▼有限公司より入手、(Luohanguo Glucoside 40% yellow type))5gを、25容量%エタノールを含む水溶液に溶解し500mLに定容した。この定容液を、あらかじめ25容量%エタノール/75容量%水で一晩以上膨潤させておいた活性炭(粒状)(実施例1、比較例1〜3)40mLを充填したカラム(カラム内径:15mm、長さ:300mm)にポンプを用いて流速3.3mL/分で注入した。
実施例1:ヨウ素吸着能1610mg/g(FG−3:(株)日本エンバイロケミカルズ製)
比較例1:ヨウ素吸着能990mg/g(ブロコールCM:(株)太平化学産業製)
比較例2:ヨウ素吸着能≧1000mg/g、且つ<1500mg/g (クラレコールKL:(株)クラレケミカル製)
比較例3:ヨウ素吸着能>1000mg/g、且つ<1500mg/g (GCN 1240 PULS:(株)キャボット・ノリット ジャパン製)。
ここで、40mlでの膨潤した活性炭の重量は、FP−3は、13.84g、ブロコールCMは、17.46g、クラレコールKLは、18.04g、GCN 1240 PULSは、20.67gであった。
なお、上記の操作はいずれも室温で行った。
(1)原料羅漢果抽出物(桂林莱茵生物科技股▲分▼有限公司より入手、(Luohanguo Glucoside 40% yellow type))5gを水に溶解し50mLに定容した。この定容液全量をビーカーに移し、これに活性炭(粉末状)(実施例2〜4、比較例4〜7)を1g添加した。これを、攪拌子を用いて30分間攪拌した後、0.45μmのメンブレンフィルターを用いて減圧濾過し、活性炭を除去した。得られたろ液を凍結乾燥して活性炭処理物を得た。なお、上記の操作はいずれも室温で行った。
実施例2:カラメル脱色能86.2%(クラレコールPK-D:(株)クラレケミカル製)、粒度75 μm以下86 μm以上
実施例3:カラメル脱色能94.6%(FP-1:(株)日本エンバイロケミカルズ製)実施例4:カラメル脱色能95.7%(FP-6:(株)日本エンバイロケミカルズ製)比較例4:カラメル脱色能73.1%(FP-4:(株)日本エンバイロケミカルズ製)比較例5:カラメル脱色能17.6%(FP-8:(株)日本エンバイロケミカルズ製)比較例6:カラメル脱色能70.9%(FP-4:(株)日本エンバイロケミカルズ製)比較例7:カラメル脱色能80%(ブロコールB印活性炭:(株)太平化学産業製)
(1)成分分析
活性炭未処理物(原料羅漢果抽出物)及び活性炭処理物(実施例3及び4、比較例7)を、参考例1(羅漢果配糖体の定量法)(2)に記載するHPLC装置及び条件を有する高速液体クロマトグラフィーに供した。得られた活性炭未処理物のクロマトグラムと活性炭処理物のクロマトグラムを比較することで、保持時間16分付近に検出されるピーク(以下、このピークを「P16」とも称する)の面積(以下「P16面積」とも称する)が、活性炭処理によって顕著に減少することが確認された。
ここで、面積は、LabSolutions((株)島津製作所)により各ピークの面積値を求めた。P16面積の割合(%)は、全ピーク面積合計値の比率で算出した。保持時間16分付近とは、ここでは保持時間15分から17分の間のピークが全ピーク面積に占める割合とした。
上記P16成分を分取し、参考例2(2)(2−1)に記載する条件のLC/MS分析に供したところ、当該成分は、分子量358ダルトンの化合物であることが確認された。
上記(1)で調製した活性炭処理物(実施例3及び4、比較例7)を0.1 w/v%の水溶液(被験試料)に調製して、官能試験に熟練したパネリスト15名に対して官能試験を実施した。
官能試験に熟練したパネリスト5名を対象として、活性炭未処理物(原料羅漢果抽出物)及び活性炭処理物(実施例4)の甘味質(8項目)について、官能試験を実施した。
(1−1)前調製
活性炭未処理物(原料羅漢果抽出物)及び活性炭処理物(実施例4)をそれぞれ、下記条件のHPLCに供して、保持時間27分以前に溶出する画分(以下「分画物(前)」と称する)と保持時間27分以後に溶出する画分(以下「分画物(後)」と称する)をそれぞれ分取し、それぞれロータリーエバポレーターで減圧濃縮し、凍結乾燥した。ここで、分取時は5w/w%水溶液であった。また、下記クロマトグラム時は、0.2%水溶液であった。
[HPLC条件]
・HPLC装置: LC-10ADvp((株)島津製作所製)
・LCカラム:Nucleosil 100-5C18(250 mm×20 mm I.D.、(株)GLサイエンス製)
・LC条件
注入量 :1 mL
カラム温度:40℃
移動相:A相:水、B相:アセトニトリル
0→10分(イソクラティック):A相80容量%、B相20容量%
10→50分(リニアグラジエント):「A相80容量%、B相20容量%」→「A相45容量%、B相55容量%」
流速 :9.999 mL/分
検出波長:UV 203 nm。
上記で調製した活性炭未処理物、活性炭未処理物の分画物(後)、及び活性炭処理の分画物(後)をそれぞれ0.05 g量り取り、水を加えて25 gとし、甘味質評価試料とした。
健常被験者5名を対象に、羅漢果抽出物および実施例4で得られた活性炭未処理物、活性炭未処理物の分画物(後)、及び活性炭処理の分画物(後)を水に溶解し、0.2%の水溶液を調製した。この水溶液を絶対評価で、甘味質(8項目:苦味、しつこさ、くせ、渋味、刺激、すっきり、まろやか、コク)を視覚的アナログ尺度(Visual Analogue Scale:VAS)方法により評価した。VASは、感覚を直線上の点として評価する方法であり、甘味などの基本味のスクリーニング検査に汎用されている(例えば、「高齢者における主観的健康感アセスメント法の検討」、Psychological Research 2004, No.3, 89−98:「4基本味における味覚機能のスクリーニング検査法の構築」、顎機能誌20; 115-129, 2014)。本実験において、VASは100mmの直線を示し、左端に「苦味が弱い」、右端には「苦味が強い」と示し、対象者には線上に点を記入してもらう。例えば、その記入した点が左端から50mmに記入されていればこの対象者は50点の苦味を感じたことにした(図3)。つまり各苦味の数値が大きくなるほど悪く苦味が強く、逆に小さくなるほど苦味が弱く甘味質として良好である。なお、試験液は被験者へランダムに渡した。それぞれ項目でVAS線の左端からの点までの距離を測定し、その平均値を軸上にプロットしレーダーチャートを作成した。
図3に示すように、活性炭未処理物と活性炭未処理物の分画物(後)との甘味質に殆ど差異は認められなかった。このことから羅漢果抽出物の分画物(前)は、甘味質に殆ど関与していないことが確認された。一方、活性炭処理物の分画物(後)は、活性炭未処理物及び活性炭未処理物の分画物(後)と比較して、苦み、くせ、刺激、すっきり、及びコクの項目において評価合計点が低下しており、良好な甘味質を有することが確認された。
Claims (7)
- 農薬を含まない羅漢果抽出物であって、
当該農薬不含羅漢果抽出物に含まれるモグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドIの総量が、当該農薬不含羅漢果抽出物100重量%あたり少なくとも33重量%であり、
下記条件のHPLC分析において保持時間16分付近に検出されるピークの面積が全ピークの総面積の3%以下である、上記農薬不含羅漢果抽出物:
[HPLC条件]
カラム:Kaseisorb LC ODS2000(150mm×4.6mmI.D.)(東京化成工業株式会社製)移動相:アセトニトリルと水の混合液
0分→10分(イソクラティック):アセトニトリル20容量%、
10分→50分(リニアグラジエント):アセトニトリル20容量%→55容量%流速:1mL/分
カラム温度:40℃
検出器:UV 203nm。 - 上記HPLC分析において保持時間16分付近に検出されるピークが分子量358ダルトンの化合物のピークである、請求項1に記載する農薬不含羅漢果抽出物。
- 上記農薬が、ジメトモルフ、トリアジメノール、テブコナゾール、ジフェノコナゾール、メタラキシルおよびメタラキシルMである請求項1または2に記載する農薬不含羅漢果抽出物。
- 農薬含有羅漢果抽出物を活性炭処理して農薬を除去する工程を有する、農薬不含羅漢果抽出物の調製方法であって、該活性炭処理で使用する活性炭が、ヨウ素吸着量が少なくとも1500mg/gである活性炭およびカラメル脱色能が少なくとも85%である活性炭よりなる群から選択されるいずれか少なくとも1つの活性炭であり、
当該活性炭の処理によるモグロサイドV、モグロサイドIV、11−オキソ−モグロサイドV及びシアメノサイドIからなる羅漢果配糖体の回収率が少なくとも70%である、調製方法、
を用いて、農薬含有羅漢果抽出物から調製された農薬不含羅漢果抽出物。 - 請求項1〜4のいずれか一項に記載する農薬不含羅漢果抽出物からなるか、または請求項1〜4のいずれか一項に記載する農薬不含羅漢果抽出物及び補助甘味成分を含有する甘味料組成物。
- 上記補助甘味成分が、単糖類、二糖類、オリゴ糖類、糖アルコール類、非糖質系甘味料、及び食物繊維類からなる群より選択される少なくとも1種である、請求項5に記載する甘味料組成物。
- 請求項5または6に記載する甘味料組成物を含有する飲食物、医薬部外品、化粧品または医薬品。
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