JP2018518952A - 甘味料または甘味増強剤として使用される新規なトリペルテングリコシド - Google Patents
甘味料または甘味増強剤として使用される新規なトリペルテングリコシド Download PDFInfo
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- JP2018518952A JP2018518952A JP2017560687A JP2017560687A JP2018518952A JP 2018518952 A JP2018518952 A JP 2018518952A JP 2017560687 A JP2017560687 A JP 2017560687A JP 2017560687 A JP2017560687 A JP 2017560687A JP 2018518952 A JP2018518952 A JP 2018518952A
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- sweetener
- oil
- dodecahydro
- cyclopenta
- Prior art date
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- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 235000019143 vitamin K2 Nutrition 0.000 description 1
- 239000011728 vitamin K2 Substances 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 229940041603 vitamin k 3 Drugs 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
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Abstract
【選択図】図1
Description
(i) 3−(3−(5−(2−ヒドロキシプロパン−2−イル)−2−メチルテトラヒドロフラン−2−イル)−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−4−((2S,3R,4S,5S)−3,4,5−トリヒドロキシテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸
化合物(i)〜(v)は、青銭柳(Cyclocarya paliurus)(同義語:Pterocarya paliurus)の水及び/又はアルコール抽出物から入手可能である。
特に好ましくは、以下の化合物のいずれか1つが豊富である抽出物である。
(ii)3−(4−(5−(アセトキシメチル)−3,4−ジヒドロキシテトラヒドロフラン−2−イロキシ)−3−(2,5−ジヒドロキシ−6−メチルヘプト−6−エン−2−イル)−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;
(iii)3−(6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−3−(2,4,5−トリヒドロキシ−6−メチルヘプト−6−エン−2−イル)−4−((2R,3R,4S,5S,6R)−3,4,5−トリヒドロキシ−6−メチルテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;
(iv)3−(6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−3−(2,4,5−トリヒドロキシ−6−メチルヘプト−6−エン−2−イル)−4−((2S,3R,4S,5S)−3,4,5−トリヒドロキシテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;
(v) 3−(3−アセチル−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−4−((2S,3R,4S,5S)−3,4,5−トリヒドロキシテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸。
本発明の抽出物は、例えば、植物全体または一部から、水抽出、アルコール抽出、または液体/アルコール抽出方法により調製可能である。好適な抽出過程としては、既知の抽出方法であり、例えば冷浸、再冷浸、温浸、撹拌冷浸、うず抽出、超音波抽出、向流抽出、パーコレーション、再パーコレーション、エバコレーション(減圧下での抽出)、ディアコレーション、および連続還流下での固/液抽出などである。工業用途にはパーコレーションが有利である。
(a)青銭柳の葉を水、C1−C4脂肪族アルコール又はこれらの混合物に浸し、懸濁液を生成する。
(b)水、C1−C4脂肪族アルコール又はこれらの混合物を使用し、摂氏50〜80度において、前述の懸濁液を抽出し、任意で、
(c)溶剤を分離する。
本発明の調製物は式(i)〜(v)の甘味料化合物を少なくとも1単位有し、例えば飲料、食品、歯磨き剤、リップスティック及び同様な製品等、様々な経口及び食品組成物、医薬組成物から望ましい甘味及び/又はフレーバーを放出するために使用され、これらの製品は消化可能または消化できないものであってもよく、他のフレーバー又は甘味料と共に使用又は別途であってよい。さらに本発明は、甘味料及び/又は調味料として使用される、式(I)の甘味料化合物を少なくとも1単位有する、様々な経口組成物及び食品組成物に関する。
本発明の他の目的は、甘味料組成物又は上述した抽出物が添加された食品組成物に関する。
・菓子類、好ましくは低カロリーまたはゼロカロリーの菓子類であって、以下を含む群から選択されるもの:ミューズリーバー製品、フルーツガム、ドラジェ、硬いキャラメルおよびチューインガム;
・ノンアルコール飲料であって、好ましくは以下を含む群から選択される:緑茶、紅茶、(緑茶および紅茶の)茶抽出物配合の緑茶あるいは紅茶飲料、ロイボスティー、他のハーブティー、フルーツ含有の低糖または無糖の清涼飲料、アイソトニック飲料、ネクター、フルーツジュースおよび野菜ジュース、フルーツジュースおよび野菜ジュース製品;
・インスタント飲料であって、好ましくは以下を含む群から選択されるもの:インスタント(緑茶、紅茶、ロイボスティー、ハーブティー)茶飲料;
・穀物製品であって、好ましくは以下を含む群から選択されるもの:低糖およびシ無糖の朝食用シリアルおよびムーズリバー;
・乳製品、好ましくは低脂肪及び無脂肪牛乳、ヨーグルト、ケフィール、ホエー、ホエー飲料、バターミルク、アイスクリームから選択される;
・大豆タンパク質または他の大豆蒸留物から製造されるものであって、好ましくは以下を含む群から選択されるもの:豆乳、豆乳製品、分離または酵素処理した大豆タンパク質を含有する飲料、大豆粉含有飲料、大豆レシチン含有製品、大豆レシチン含有製品から製造される製品、並びにフルーツ製品との混合物および追加調味料との混合物;
・甘味料製品、錠剤およびサッシェ;
・無糖ドラジェ;
・乳成分配合または無配合のアイスクリームであって、好ましくは無糖のもの。
本発明の食品組成物は、添加甘味料又は甘味化合物、アロマ化合物、調味料化合物、並びにこれらの群から選択された組成物をさらに含む。
アロマ化合物及び調味料は当業者に広く知られており、本発明のフレーバー組成物に添加してもよい。これらの調味料は、合成フレーバー液および/または油であって植物の葉、花、果実などに由来するものあるいはこれらの組合せであってよい。このようなフレーバー液の代表例としては以下のものが挙げられる:ユーカリノキ、レモン、オレンジ、バナナ、ブドウ、ライム、アプリコットおよびグレープフルーツ油などの天然又は合成のフルーツ性フレーバー、リンゴ、イチゴ、サクランボ、オレンジ、パイナップルなどのフルーツエッセンス、コーヒー、ココア、コーラ、南京豆、アーモンドなどの豆およびナッツ由来の調味料。
本発明において、「甘味料」という用語は、スクロースの甘味度(甘味度1度)を基準として少なくとも25度の相対甘味度を有する物質を指す。本発明(a)に係る経口消費可能製品(特に食品、飼料品または薬剤)に用いる甘味料は、好ましくは非齲蝕原性であり、及び/または経口消費可能製品1グラム当り5kcalのエネルギー量を有する。
・ミラクリン、モネリン、マビンリン、タウマチン、クルクリン、ブラゼイン、ペンタイジン、D−フェニルアラニン、D−トリプトファン、並びにこれらのアミノ酸及び/又はタンパク質を含有する天然源から得られる抽出物又は画分、並びにこれらのアミノ酸及び/又はタンパク質の生理学的に許容できる塩、特にナトリウム塩、カリウム塩、カルシウム塩又はアンモニウム塩;
・ネオヘスペリジンジヒドロカルコン、ナリンギンジヒドロカルコン、ステビオシド、ステビオルビオシド、レバウディオサイド、特にレバウディオサイドA、レバウディオサイドB、レバウディオサイドC、レバウディオサイドD、レバウディオサイドE、レバウディオサイドF、レバウディオサイドG、レバウディオサイドH、ズルコシド及びルブソシド、スアビオシドA、スアビオシドB、スアビオシドG、スアビオシドH、スアビオシドI、スアビオシドJ、バイユノシド1、バイユノシド2、フロミソシド1、フロミソシド2、フロミソシド3、及びロミソシド4、アブルソシドA、アブルソシドB、アブルソシドC、アブルソシドD、シクロカリオシドA及びシクロカリオシドI、オスラジン、ポリポドシドA、ストロギン1、ストロギン2、ストロギン4、セリグエアインA、ジヒドロクェルセチン−3−アセタート、ペリラルチン、テロスモシドA15、ペリアンドリンI−V、プテロカリオシド、シクロカリオシド、ムクロジオシド、trans−アネトール、trans−シンナムアルデヒド、ブリオシド、ブリオノシド、ブリオノズルコシド、カルノシフロシド、スカンデノシド、ギペノシド、トリロバチン、フロリジン、ジヒドロフラバノール、ヘマトキシリン、シアニン、クロロゲン酸、アルビジアサポニン、テロスモシド、ガウジカウジオシド、モグロシド、モグロシドV、ヘルナンズルシン、モナチン、フィロズルシン、グリチルレチン酸及びその誘導体、特にそのグリコシド、例えばグリチルリジン等、並びにこれらの化合物の生理学的に許容できる塩、特にナトリウム塩、カリウム塩、カルシウム塩又はアンモニウム塩;
・ソーマトコッカス(thaumatococcus)抽出物(カテンフ・ブッシュ(katemfe bush))、ステビア属亜種(特にステビア・レバウディアナ(Stevia rebaudiana))の抽出物、スウィングル抽出物(モモルジカ(Momordica)又はシラチア・グロスベノリイ(Siratia grosvenorii)、ルオハングオ)、グリセリジア(Glycerrhyzia)亜種(特にグリセリジア・グラブラ(Glycerrhyzia glabra))の抽出物、ルブス属亜種(特にルブス・スアビッシムス(Rubus suavissimus))の抽出物、柑橘類抽出物並びにメキシカン・スイートハーブ(Lippia dulcis)の抽出物から成る群より選択される抽出物又は抽出物の濃縮画分から成る群より選択される天然に存在する甘味料。
・甘い炭水化物または糖類(例えば、スクロース/サッカロース、トレハロース、ラクトース、マルトース、メリジトース、ラフィノース、パラチノース、ラクツロース、D−フルクトース、D−グルコース、D−ガラクトース、L−ラムノース、D−ソルボース、D−マンノース、D−タガトース、D−アラビノース、L−アラビノース、D−リボース、D−グリセルアルデヒド、マルトデキストリン);又は
・これらの炭水化物を含有する植物調製物、(例えば甜菜(ベータブルガリス(Beta vulgaris)亜種、糖画分、糖シロップ、糖蜜)、サトウキビ(サッカラム オフィシナラム(Saccharum officinarum)亜種、糖蜜、糖シロップ)由来、サトウカエデ(アセル(Acer)亜種)由来、アガーベ(例えば、アガーベ濃厚ジュース)由来);
・合成/酵素から製造した澱粉又は糖類の加水分解物(例えば、転化糖シロップ、コーンスターチから製造した高濃縮フルクトースシロップ);
・果実濃縮物(例えば、リンゴまたは西洋ナシ由来、りんごシロップ、西洋なしシロップ;
・糖アルコール類(例えば、エリスリトール、スレイトール、アラビトール、リビトール、キシリトール、ソルビトール、マンニトール、ズルシトール、ラクチトール);
・タンパク質(例えば、ミラクリン、モネリン、タウマチン、クルクリン、ブラゼイン);
・甘味化剤(例えば、マガップ、シクラミン酸ナトリウム、アセスルファムK、ネオヘスペリジンジヒドロカルコン、サッカリン−ナトリウム塩、アスパルテーム(登録商標)、スーパーアスパルテーム、ネオテーム、アリテーム、スクラロース、ラグドゥネーム、カレラーム、スクロノネート、スクロオクテート、モナチン);
・ある種の甘味アミノ酸(グリシン、D−ロイシン、D−スレオニン、D−アスパラギン、D−フェニルアラニン、D−トリプトファン、L−プロリン);
・他の甘味低分子物質(例えば、レバウディオサイド、ステビオシド、モグロシド、ヘルナンズルチン、フィルズルチン、ジヒドロカルコン、グリコシド類、グリシルリジン、グリシルレチン酸アンモニウム塩または他のグリシルレチン酸誘導体);
・甘味のある植物の抽出物、特にMomordica grosvenori(ルオハングオ)、アジサイ(Hydrangea macrophylla)、ステビア属亜種(特にステビア・レバウディアナ)、甜茶(Rubus suavissimus)、エゾデンダ(Polypodium vulgare)、トウアズキ(Abrus precatorius)、Pterocarya paliurus、Baccharis gaudichaudiana、Albizia myriophylla、Bryonia dioica、Phlomis betonicoides、Hemsleya carnosiflora、メキシカン・スイートハーブ、アマチャヅル(Gynostemma pentaphyllum)、スペインカンゾウ(Glycyrrhiza glabra(リコリス))又はこれらの植物から分離された甘味物質。
本発明に係る好適な経口消費可能製品(特に食品、飼料品または薬剤)に用いる有利な増粘剤は、以下を含む群から選択される:架橋ポリアクリル酸およびその誘導体、キサンタンガム、寒天、アルギン酸塩またはチロースなどの多糖類およびその誘導体、カルボキシメチルセルロースまたはヒドロキシカルボキシメチルセルロースなどのセルロース誘導体、脂肪アルコール、モノグリセリドおよび脂肪酸、ポリビニルアルコール、およびポリビニルピロリドン。
本発明に係る経口消費可能製品(特に食料品または飼料品)は、好ましくはチューインガムであって、チューインガムベースを含む。このチューインガムベースは、好ましくは以下を含む群から選択される:チューインガムベースまたはバブルガムベース。バブルガムベースはガムで風船を作ることができるように、より柔らかいベースである。本発明に係る好適なチューインガムベースは、従来用いられている天然樹脂または天然のチクル樹脂に加えて、以下を含む:ポリ酢酸ビニル(PVA)、ポリエチレン、(低分子量あるいは中間の分子量)、ポリイソブテン(PIB)、ポリブタジエン、イソブテン−イソプレンコポリマー(ブチルゴム)、ポリビニルエチルエーテル(PVE)、ポリビニルブチルエーテルのようなエラストマー、ビニルエステルのコポリマー、ビニルエーテル、スチレン−ブタジエンコポリマー(スチレン−ブタジエンゴム、SBR)、またはビニルエラストマー、例えば酢酸ビニル/ラウリン酸ビニル、酢酸ビニル/ステアリン酸ビニルまたはエチレン/酢酸ビニル、および前述のエラストマーとの混合物(欧州特許出願公開第0242325号、米国特許第4,518,615号、米国特許第5,093,136号、米国特許第5,266,336号、米国特許第5,601,858号または米国特許第6,986,709号参照)。また、本発明に好ましく用いるチューインガムベースは、例えば以下の更なる成分を含む:(ミネラル)充填材、可塑剤、乳化剤、抗酸化剤、ワックス、硬化植物性脂肪もしくは動物性脂肪などの脂肪または脂肪油、モノ−、ジ−またはトリグリセリド。好適な(ミネラル)充填材は、例えば、炭酸カルシウム、二酸化チタン、二酸化珪素、タルカム、酸化アルミニウム、リン酸二カルシウム、リン酸三カルシウム、および水酸化マグネシウム並びにこれらの混合物である。好適な可塑剤または粘着防止剤(脱粘着剤)は、例えば、ラノリン、ステアリン酸、ステアリン酸ナトリウム、酢酸エチル、ジアセチン(グリセリンジアセタート)、トリアセチン(グリセリントリアセテート)、トリエチルシトレートである。好適なワックスは、例えば、パラフィンワックス、キャンデリラワックス、カルナウバワックス、微結晶ワックスおよびポリエチレンワックスである。好適な乳化剤は、例えば、レシチンのようなホスファチドであり、例えばグリセリンモノステアレートなどの脂肪酸のモノ−およびジ−グリセリドである。
本発明の他の実施例として、食品添加剤には、添加剤の群としてビタミン(構成物e1)を含んでもよい。ビタミンは、生化学的作用において多岐に渡る機能を持つ。ビタミンの一部は、ホルモンと同様の機能を有し、ミネラルの代謝を維持し(例えばビタミンD)、または細胞及び組織の成長、並びに細胞分化を促す(例えばビタミンA)作用を持つ。他のビタミンは、酸化防止剤として用いられる(例えばビタミンE及び一定条件下のビタミンC)。ビタミンのうちの最大数は、酵素補因子の先駆体であり(例えばビタミンB)、一定の代謝過程において、触媒作用をする酵素の補酵素として機能する。これに伴い、例えば配合群の一部として、時にビタミンは酵素と強く結合する。配合群の一例として、脂肪酸の合成を起こす酵素の一部であるビオチンが挙げられる。一方、例えば容易に分離される群として、ビタミンが弱い力で結合し、共触媒として機能し、これによって分子間の化合物または電子を利用して輸送する。例えば葉酸は、様々な形態の炭素群−メチル基、ホルミル基、メチレン基の群を細胞内に輸送する。酵素−基質反応におけるビタミンの働きは良く知られているが、ビタミンの他の性質も身体にとって重要な要素である。本発明において、適したビタミンは以下の群から選択される。
・ビタミンB1(チアミン)
・ビタミンB2(リボフラビン)
・ビタミンB3(ナイアシン、ニコチンアミド)
・ビタミンB5(パントテン酸)
・ビタミンB6(ピリドキシン、ピリドキサミン、ピリドキサール)
・ビタミンB7(ビオチン)
・ビタミンB9(葉酸、フォリン酸)
・ビタミンB12(シアノコバラミン、ヒドロキソコバラミン、メチルコバラミン)
・ビタミンC(アスコルビン酸)
・ビタミンD(コレカルシフェロール)
・ビタミンE(トコフェロール、トコトリエノール)及び
・ビタミンK(フィロキノン、メナキノン)。
本発明の他の目的は、甘味料化合物又は上述の抽出物を含有する、経口組成物に関する。これらの組成物は、上述した内容に加え、さらなる甘味料又は甘味化合物、アロマ化合物、フレーバー化合物並びにこれらの混合物を含んでもよい。
本発明の他の目的は、上述した甘味化合物又は抽出物を含む医薬組成物に関する。これらの組成物は、アロマ及び調味料等、前述した食品及び経口組成物と同様の添加剤を含有し得る。
(i)少なくとも1つの化合物(i)〜(v)、及び
(ii)化合物(i)〜(v)とは異なる少なくとも1つの天然または合成甘味料。
<抽出>
乾燥した青銭柳の葉1.4kg(日本、東京都の株式会社ハイファジェネシスより購入)から、13Lのメタノール−MTB−エーテルを使用し、室温で24時間抽出した(結果物:98g)。
逆相中圧クロマトグラフィーを使用し、以下の条件において、青銭柳の抽出物99gを分離した。
・固定相:RP−18、40〜63μ(メルク社)
・移動相の溶剤A:水
・移動相の溶剤B:メタノール
・グラジエント:86%の溶剤A〜10%溶剤Aにて60分
・カラム寸法:50x250mm
・固定相:RP−18、40〜63μ(メルク社)
・移動相の溶剤A:水
・移動相の溶剤B:メタノール
・グラジエント:86%の溶剤A〜10%溶剤Aにて60分
・カラム寸法:50x250mm
手順Dで説明されたプレフラクショネーションによって抽出した画分を用いて、逆相クロマトグラフィーによって、精製された化合物を分離した。
調製されたHPLCの画分(各40ml)を収集し、HPLC−MSによって分析した。保管時間及び質量スペクトルに応じ、同じ化合物を含む画分を結合し、蒸発し、HPLC−MS及びNMR(1H−NMR、HH−COSY、HSQC、HMBC)によって分析した。NMR及びMSデータを解釈し、構造を解明した。
分離した式(i)〜(v)の化合物に対し、質量分析法及びNMR分析法によって特徴付けした。詳しくは図1〜図10を参照。化合物は以下の様に特定した。
化合物A〜E(各10mg)に記載されたアンモニウム塩は、各化合物に1Nの過量の水酸化アンモニウムを添加することにより調製した。結果物の塩はフリーズドライされ、水で容易に再分解できる。
3=コントロール溶液よりも甘い。
2=コントロール溶液に相当する甘味。
1=コントロール溶液よりも少ないが、甘味が存在する。
以下の表5a〜5dは、前述した甘味料を少なくとも1つ含む経口組成物の例である。
Claims (8)
- 以下の群から選択される、少なくとも1単位のトリテルペングリコシド化合物を含む甘味料組成物:
(i) 3−(3−(5−(2−ヒドロキシプロパン−2−イル)−2−メチルテトラヒドロフラン−2−イル)−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−4−((2S,3R,4S,5S)−3,4,5−トリヒドロキシテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;
(ii)3−(4−(5−(アセトキシメチル)−3,4−ジヒドロキシテトラヒドロフラン−2−イロキシ)−3−(2,5−ジヒドロキシ−6−メチルヘプト−6−エン−2−イル)−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;
(iii)3−(−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−3−(2,4,5−トリヒドロキシ−6−メチルヘプト−6−エン−2−イル)−4−((2R,3R,4S,5S,6R)−3,4,5−トリヒドロキシ−6−メチルテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;
(iv)3−(6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−3−(2,4,5−トリヒドロキシ−6−メチルヘプト−6−エン−2−イル)−4−((2S,3R,4S,5S)−3,4,5−トリヒドロキシテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;又は
(v)3−(3−アセチル−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−4−((2S,3R,4S,5S)−3,4,5−トリヒドロキシテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸。 - 食品または医薬品組成物に使用する甘味料である、請求項1に記載の甘味料組成物の使用。
- トリテルペングリコシド化合物の製造方法であって、前記トリテルペングリコシド化合物は:
(i) 3−(3−(5−(2−ヒドロキシプロパン−2−イル)−2−メチルテトラヒドロフラン−2−イル)−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−4−((2S,3R,4S,5S)−3,4,5−トリヒドロキシテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;
(ii) 3−(4−(5−(アセトキシメチル)−3,4−ジヒドロキシテトラヒドロフラン−2−イロキシ)−3−(2,5−ジヒドロキシ−6−メチルヘプト−6−エン−2−イル)−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;
(iii)3−(6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−3−(2,4,5−トリヒドロキシ−6−メチルヘプト−6−エン−2−イル)−4−((2R,3R,4S,5S,6R)−3,4,5−トリヒドロキシ−6−メチルテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;
(iv)3−(−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−3−(2,4,5−トリヒドロキシ−6−メチルヘプト−6−エン−2−イル)−4−((2S,3R,4S,5S)−3,4,5−トリヒドロキシテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;又は
(v)3−(3−アセチル−6,9a,9b−トリメチル−7−(プロパ−1−エン−2−イル)−4−((2S,3R,4S,5S)−3,4,5−トリヒドロキシテトラヒドロ−2H−ピラン−2−イロキシ)ドデカヒドロ−1H−シクロペンタ[a]ナフタレン−6−イル)プロパン酸;から選択され、
さらに、
(a)青銭柳の葉を水、C1−C4脂肪族アルコール又はこれらの混合物に浸し、懸濁液を生成する工程と、
(b)水、C1−C4脂肪族アルコール又はこれらの混合物を使用し、摂氏50〜80度にで、前記懸濁液を抽出する工程と、
(c)溶剤を分離する工程と、を含む、トリテルペングリコシド化合物の製造方法。 - 請求項1に記載の甘味料組成物を含む、経口組成物。
- さらに食品組成物又は医薬品組成物である、請求項4に記載の経口組成物。
- さらに、添加甘味料又は甘味化合物、アロマ化合物、フレーバー化合物、並びにこれらの群から選択された組成物をさらに含む、請求項5に記載の経口組成物。
- 請求項1に係る甘味料組成物を添加し、食料又は医薬組成物に甘味効果に与えるまたは増強する方法であって、経口摂取を目的とする組成物に十分な甘味を与える方法。
- 食料、口腔又は医薬組成物に対し、前記甘味料組成物又は前記抽出物を、最終組成物に対して1〜2,000ppm添加する、請求項7に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP15173722.8 | 2015-06-24 | ||
EP15173722.8A EP3108754B1 (en) | 2015-06-24 | 2015-06-24 | Novel triterpene glycosides as sweeteners or sweetener enhancer |
PCT/EP2016/063415 WO2016207001A1 (en) | 2015-06-24 | 2016-06-12 | Novel triterpene-glycosides as sweeteners or sweetener enhancer |
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JP2018518952A true JP2018518952A (ja) | 2018-07-19 |
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JP2017560687A Ceased JP2018518952A (ja) | 2015-06-24 | 2016-06-12 | 甘味料または甘味増強剤として使用される新規なトリペルテングリコシド |
Country Status (13)
Country | Link |
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US (1) | US20180354980A1 (ja) |
EP (1) | EP3108754B1 (ja) |
JP (1) | JP2018518952A (ja) |
KR (1) | KR20180021103A (ja) |
CN (1) | CN108235686A (ja) |
AR (1) | AR110571A1 (ja) |
AU (1) | AU2016284715A1 (ja) |
BR (1) | BR112017025657A2 (ja) |
CA (1) | CA2988029A1 (ja) |
EA (1) | EA201890129A1 (ja) |
MX (1) | MX2017016588A (ja) |
WO (1) | WO2016207001A1 (ja) |
ZA (1) | ZA201708013B (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3461349B1 (en) * | 2017-09-27 | 2020-12-09 | Analyticon Discovery GmbH | Novel diterpene glycosides as sweeteners or sweetener enhancer |
CN110746474B (zh) * | 2019-11-14 | 2022-10-04 | 广西师范大学 | 达玛烷型三萜皂苷类化合物及其制备方法和在制备抗炎药物中的应用 |
CN111100175A (zh) * | 2020-01-03 | 2020-05-05 | 中南大学 | 一种3,4-裂环达玛烷型四环三萜化合物及其提取方法和应用 |
EP3858155A1 (en) | 2020-01-30 | 2021-08-04 | Analyticon Discovery GmbH | A sweetener or sweetness enhancer composition |
CN113004354B (zh) * | 2020-04-20 | 2022-08-19 | 中南大学 | 达玛烷型四环三萜化合物及其抗痛风应用 |
CN113087750A (zh) * | 2021-03-23 | 2021-07-09 | 三峡大学 | 一种青钱柳甜苷及其制备方法及其应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2015082012A1 (en) * | 2013-12-05 | 2015-06-11 | Analyticon Discovery Gmbh | Novel triterpene-glycosides as sweeteners or sweetener enhancers |
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US3087821A (en) | 1961-11-28 | 1963-04-30 | Robert M Horowitz | Dihydrochalcone derivatives and their use as sweetening agents |
US4518615A (en) | 1983-08-23 | 1985-05-21 | Warner-Lambert Company | Non-adhesive chewing gum base composition |
US4721620A (en) | 1986-04-01 | 1988-01-26 | Warner-Lambert Company | Polyvinylacetate bubble gum base composition |
US5093136A (en) | 1991-05-08 | 1992-03-03 | Nabisco Brands, Inc. | Dual gum base bubble gum |
US5266336A (en) | 1991-11-12 | 1993-11-30 | Wm. Wrigley Jr. Company | High flavor impact non-tack chewing gum with reduced plasticization |
US5601858A (en) | 1994-12-29 | 1997-02-11 | Warner-Lambert Company | Non-stick chewing gum |
US6986709B2 (en) | 2001-09-21 | 2006-01-17 | Igt | Gaming device having games with variable game functions |
EP2187871B1 (en) | 2007-08-16 | 2016-04-13 | Symrise AG | Mixtures comprising pellitorin and uses thereof |
EP2188300B1 (en) | 2007-08-17 | 2013-01-30 | Givaudan SA | Novel sweetener iso-mogroside v |
CN101829187B (zh) * | 2010-04-28 | 2012-10-03 | 广西壮族自治区药用植物园 | 果味青钱柳咀嚼片的制备方法 |
US9101162B2 (en) | 2010-09-03 | 2015-08-11 | Purecircle Sdn Bhd | High-purity mogrosides and process for their purification |
US8691190B2 (en) * | 2010-10-01 | 2014-04-08 | The Procter & Gamble Company | Oral care compositions with improved sweetness |
EP2529633B1 (de) | 2011-06-01 | 2014-08-06 | Symrise AG | Oral konsumierbare Zubereitungen umfassend bestimmte süß schmeckende Triterpene und Triterpenglycoside |
CN102432660A (zh) * | 2011-12-20 | 2012-05-02 | 苏州宝泽堂医药科技有限公司 | 一种青钱柳苷ⅰ的提取分离方法 |
CN102552388B (zh) * | 2012-01-11 | 2013-07-03 | 南京林业大学 | 青钱柳胶囊及其制备方法 |
CN104543135A (zh) * | 2015-01-23 | 2015-04-29 | 湖南阿香茶果食品有限公司 | 一种黑茶口感改善添加剂及其应用 |
-
2015
- 2015-06-24 EP EP15173722.8A patent/EP3108754B1/en active Active
-
2016
- 2016-06-12 US US15/737,053 patent/US20180354980A1/en not_active Abandoned
- 2016-06-12 CA CA2988029A patent/CA2988029A1/en not_active Abandoned
- 2016-06-12 BR BR112017025657A patent/BR112017025657A2/pt not_active Application Discontinuation
- 2016-06-12 CN CN201680036359.1A patent/CN108235686A/zh active Pending
- 2016-06-12 WO PCT/EP2016/063415 patent/WO2016207001A1/en active Application Filing
- 2016-06-12 KR KR1020187002061A patent/KR20180021103A/ko unknown
- 2016-06-12 JP JP2017560687A patent/JP2018518952A/ja not_active Ceased
- 2016-06-12 EA EA201890129A patent/EA201890129A1/ru unknown
- 2016-06-12 MX MX2017016588A patent/MX2017016588A/es unknown
- 2016-06-12 AU AU2016284715A patent/AU2016284715A1/en not_active Abandoned
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2017
- 2017-11-24 ZA ZA2017/08013A patent/ZA201708013B/en unknown
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Patent Citations (1)
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---|---|---|---|---|
WO2015082012A1 (en) * | 2013-12-05 | 2015-06-11 | Analyticon Discovery Gmbh | Novel triterpene-glycosides as sweeteners or sweetener enhancers |
Non-Patent Citations (2)
Title |
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BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 2014年, vol. 57, JPN6020003112, pages 216 - 220, ISSN: 0004202808 * |
J. AGRIC. FOOD CHEM., 1995年, vol. 43, JPN6020003113, pages 2602 - 2607, ISSN: 0004202807 * |
Also Published As
Publication number | Publication date |
---|---|
ZA201708013B (en) | 2018-11-28 |
CN108235686A (zh) | 2018-06-29 |
KR20180021103A (ko) | 2018-02-28 |
CA2988029A1 (en) | 2016-12-29 |
EP3108754A1 (en) | 2016-12-28 |
EP3108754B1 (en) | 2019-01-30 |
EA201890129A1 (ru) | 2018-05-31 |
BR112017025657A2 (pt) | 2018-08-07 |
AR110571A1 (es) | 2019-04-10 |
MX2017016588A (es) | 2018-05-15 |
WO2016207001A1 (en) | 2016-12-29 |
US20180354980A1 (en) | 2018-12-13 |
AU2016284715A1 (en) | 2017-12-07 |
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