JP2021533729A - テルペングリコシド誘導体およびその使用 - Google Patents
テルペングリコシド誘導体およびその使用 Download PDFInfo
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- JP2021533729A JP2021533729A JP2020554457A JP2020554457A JP2021533729A JP 2021533729 A JP2021533729 A JP 2021533729A JP 2020554457 A JP2020554457 A JP 2020554457A JP 2020554457 A JP2020554457 A JP 2020554457A JP 2021533729 A JP2021533729 A JP 2021533729A
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- Prior art keywords
- glucosylated
- compound
- rebaugioside
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- mono
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- -1 Terpene glycoside Chemical class 0.000 title claims abstract description 157
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- 238000006243 chemical reaction Methods 0.000 claims description 22
- UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 claims description 21
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Abstract
Description
本出願は、2018年8月22日に出願されたPCT出願番号PCT/CN2018/101661号の優先権の利益を主張し、その全体が本明細書に記載されているかのように参照により本明細書に組み込まれる。
本開示は、概して、テルペングリコシド、例えば、ステビア(Stevia rebaudiana Bertoni)、テンヨウケンコウシ(Rubus suavissimus)、またはラカンカ(Siraitia grosvenorii)から抽出された特定のかかる化合物に関する。本開示はまた、かかる化合物の、食品成分、フレーバー、および甘味料としての使用、および関連する方法も提供する。本開示はまた、かかる化合物を含む摂取可能な組成物、ならびにかかる化合物を特定の植物の源から選択的に抽出するための方法も提供する。
味覚システムは、外界の化学組成に関する感覚情報を提供する。味覚伝達は、動物の化学的に引き起こされる感覚のより洗練された形態の1つである。味覚のシグナル伝達は、単純な後生動物から最も複雑な脊椎動物まで、動物界全体で見られる。哺乳類には、甘味、苦味、酸味、塩味、およびうま味の5つの基本的な味覚様式があると考えられている。
本開示は、トランスグルコシル化方法と、かかる化合物の他のグルコシル化誘導体に対して改善された味覚プロファイルを有するグルコシル化天然低カロリー甘味料とを提供する。
以下の説明では、例示として示される、実施され得る特定の実施形態が参照される。これらの実施形態は、当業者が本明細書に記載される本発明を実施できるようにするために詳細に説明されており、他の実施形態を利用することができ、本明細書に提示される態様の範囲から逸脱することなく論理的変更を行うことができることを理解されたい。したがって、例示的な実施形態の以下の説明は、限定された意味で解釈されるべきではなく、本明細書に提示される様々な態様の範囲は、添付の特許請求の範囲によって定義される。要約は、読者が技術的開示の性質および要点を迅速に確認できるようにするために提供されている。要約は、特許請求の範囲の範囲または意味を解釈または制限するために使用されることにならないことを理解した上で提出される。
特定の態様では、本開示は、グルコシル化テルペングリコシドの製造方法であって、(a)α−グルコシル糖化合物、テルペングリコシド、およびトランスグルコシダーゼ酵素を含む水性組成物を供給する工程;および(b)α−グルコシル糖化合物を、トランスグルコシダーゼ酵素の存在下でテルペングリコシドと反応させて、テルペングリコシジル部分および1つ以上のα−グルコシル糖部分を有するグルコシル化テルペングリコシドを形成する工程を含み、ここで、該グルコシル化テルペングリコシドは、該テルペングリコシド部分と1つ以上のα−グルコシル糖部分のうちの1つとの間に1つのα−1,6グルコシド結合を有する、方法を提供する。いくつかのこのような態様では、方法は、テルペングリコシドの不快な味覚を低減する方法である。
いくつかの実施形態では、グルコシル化テルペングリコシドは、モノα−1,6グルコシル化ステビオシド、モノα−1,6グルコシル化レバウジオシドA、モノα−1,6グルコシル化レバウジオシドB、モノα−1,6グルコシル化レバウジオシドC、モノα−1,6グルコシル化レバウジオシドD、モノα−1,6グルコシル化レバウジオシドE、モノα−1,6グルコシル化レバウジオシドF、モノα−1,6グルコシル化レバウジオシドG、モノα−1,6グルコシル化レバウジオシドM、モノα−1,6グルコシル化ズルコシドA、モノα−1,6グルコシル化ステビオールビオシド、モノα−1,6グルコシル化ルブソシド、およびそれらの任意の組み合わせからなる群から選択される。
本明細書に記載されたグルコシル化テルペングリコシドは、様々な風味付けされた物品において甘味増強剤、フレーバー増強剤、または甘味料として使用され得る。そのいくつかの実施形態では、本開示は、風味付けされた物品の甘味を付与、増強、改善、または改変するためのかかるグルコシル化テルペングリコシドの使用を提供する。
実施例1:本明細書に提示されたいくつかの態様による方法による出発物質としてルブソシドおよびマルトデキストリンを使用するモノα−1,6−グルコシル化ステビオシド化合物(化合物IおよびII)の生成
ルブソシド(2g)およびデキストロース当量(DE)が18であるコーンマルトデキストリン(2g)を、10mlのNaOAc−HOAc(pH=6.0、0.2M、10mL)緩衝液または脱イオン水に室温で溶解した。続いて、100μlのトランスグルコシダーゼL(アマノ(Amano))を混合物に加えた。次に、酵素を含む混合物を60℃に加熱し、酵素を含む混合物を60℃で24時間インキュベートして、トランスグルコシド化反応を進行させ、それにより、単一のα−1,6グルコシド結合を有するグルコシル化テルペングリコシドを生成した。反応混合物を100℃で30分間インキュベートしてトランスグルコシダーゼを不活性化することにより反応を停止させた。
ルブソシド(2g)およびマルトース(2g)を、10mlのNaOAc−HOAc(pH=6.0、0.2M、10mL)緩衝液または脱イオン水に室温で溶解した。続いて、100μLのトランスグルコシダーゼL(アマノ)を混合物に加えた。次に、酵素を含む混合物を60℃に加熱し、酵素を含む混合物を60℃で24時間インキュベートして、トランスグルコシド化反応を進行させ、それにより、単一のα−1,6グルコシド結合を有するグルコシル化テルペングリコシドを生成した。反応混合物を100℃で30分間インキュベートしてトランスグルコシダーゼを不活性化することにより反応を停止させた。
レバウジオシドA(2g)およびデキストロース当量(DE)が18であるコーンマルトデキストリン(2g)を、室温で10mlの脱イオン水に溶解した。続いて、100μlのトランスグルコシダーゼL(アマノ)を混合物に加えた。次に、酵素を含む混合物を60℃に加熱し、酵素を含む混合物を60℃で24時間インキュベートして、トランスグルコシド化反応を進行させ、それにより、単一のα−1,6グルコシド結合を有するグルコシル化テルペングリコシドを生成した。反応混合物を100℃で30分間インキュベートしてトランスグルコシダーゼを不活性化することにより反応を停止させた。
ステビオールグリコシド(90w/w%)(1g)とデキストロース当量(DE)が18であるコーンマルトデキストリン(1g)との組成物を、室温で5mlの脱イオン水に溶解した。続いて、100μlのトランスグルコシダーゼL(アマノ)を混合物に加えた。次に、酵素を含む混合物を60℃に加熱し、酵素を含む混合物を60℃で24時間インキュベートして、トランスグルコシド化反応を進行させ、それにより、単一のα−1,6グルコシド結合を有するグルコシル化テルペングリコシドを生成した。反応混合物を100℃で30分間インキュベートしてトランスグルコシダーゼを不活性化することにより反応を停止させた。
化合物IおよびIIを含む組成物を、実施例1に記載された方法に従って生成した。組成物を、(i)水または(ii)2w/w%のスクロース溶液のいずれかに溶解し、ここで、溶液中の組成物の最終濃度は、40ppmであった。(i)1.5w/w%または(ii)2w/w%のスクロースの対応する対照溶液も生成した。6人の専門家のパネルが、三肢強制選択法(3-Alternative Forced Choice)(3−AFC)および甘味強度スケール法(sweet intensity scale method)を使用して、試験組成物の溶液とスクロース溶液との違いを評価した。すべてのサンプルを、ランダムな順序でブラインドで試験した。
少なくとも1種のグルコシル化テルペングリコシドを含む組成物を、前の実施例に記載された方法に従って生成した。化合物を水に溶解し(代替的に、化合物を、2(w/w)%または4(w/w)%のスクロース溶液または7(w/w)%の転化糖と組み合わせることに加えて、0.15(w/w)%のクエン酸溶液と組み合わせることもできる)、ここで、溶液中の組成物の最終濃度は、1〜1000ppmの範囲であり得る。味覚の専門家のパネルが溶液を評価した。
Claims (13)
- グルコシル化テルペングリコシドの製造方法であって、
(a)α−グルコシル糖化合物、テルペングリコシド、およびトランスグルコシダーゼ酵素を含む水性組成物を供給する工程;および
(b)前記α−グルコシル糖化合物を、前記トランスグルコシダーゼ酵素の存在下で前記テルペングリコシドと反応させて、テルペングリコシジル部分および1つ以上のα−グルコシル糖部分を有するグルコシル化テルペングリコシドを形成する工程
を含み、
ここで、前記グルコシル化テルペングリコシドは、前記テルペングリコシド部分と前記1つ以上のα−グルコシル糖部分のうちの1つとの間に1つのα−1,6グルコシド結合を有する、方法。 - 前記反応が、前記水性組成物をインキュベートすることを含む、請求項1記載の方法。
- 前記テルペングリコシドが、ステビオシド、レバウジオシドA、レバウジオシドB、レバウジオシドC、レバウジオシドD、レバウジオシドE、レバウジオシドF、レバウジオシドG、レバウジオシドM、ズルコシドA、ステビオールビオシド、ルブソシド、ステビア植物のテルペングリコシド、テンヨウケンコウシ植物のテルペングリコシド、ラカンカ植物のテルペングリコシド、およびそれらの任意の組み合わせからなる群から選択される、請求項1または2記載の方法。
- 前記α−グルコシル糖化合物が、マルトース、マルトトリオース、マルトテトラオース、デンプンの部分加水分解物、マルトデキストリン、グルコース、スクロース、およびそれらの任意の組み合わせからなる群から選択される、請求項1から3までのいずれか1項記載の方法。
- 前記トランスグルコシダーゼが、トランスグルコシダーゼLである、請求項1から4までのいずれか1項記載の方法。
- 前記グルコシル化テルペングリコシドが、モノα−1,6グルコシル化ステビオシド、モノα−1,6グルコシル化レバウジオシドA、モノα−1,6グルコシル化レバウジオシドB、モノα−1,6グルコシル化レバウジオシドC、モノα−1,6グルコシル化レバウジオシドD、モノα−1,6グルコシル化レバウジオシドE、モノα−1,6グルコシル化レバウジオシドF、モノα−1,6グルコシル化レバウジオシドM、モノα−1,6グルコシル化ズルコシドA、モノα−1,6グルコシル化ステビオールビオシド、モノα−1,6グルコシル化ルブソシド、およびそれらの任意の組み合わせからなる群から選択される、請求項1から5までのいずれか1項記載の方法。
- 前記グルコシル化テルペングリコシドが、式Iの化合物、式IIの化合物、式IIIの化合物、式IVの化合物、式Vの化合物、式VIの化合物、式VIIの化合物、式VIIIの化合物、および式IXの化合物からなる群から選択される、請求項1から5までのいずれか1項記載の方法。
- 前記グルコシル化テルペングリコシドが、式Iの化合物、式IIの化合物、式VIIの化合物、式VIIIの化合物、および式IXの化合物からなる群から選択される、請求項7記載の方法。
- 前記グルコシル化テルペングリコシドが、式IIIの化合物、式IVの化合物、式Vの化合物および式VIの化合物からなる群から選択される、請求項7記載の方法。
- 前記化合物が、請求項1から9までのいずれか1項記載の方法によって形成されたグルコシル化テルペングリコシドである、風味付けされた物品の甘味を増強するための化合物の使用。
- 前記化合物が、1ppm〜1000ppmの範囲の濃度で風味付けされた物品中に存在する、請求項10記載の使用。
- 前記風味付けされた物品が、カロリー甘味料、低カロリー甘味料、または無カロリー甘味料などの甘味料を含む、請求項10または11記載の使用。
- 前記甘味料が、スクロース、フルクトース、エリスリトール、キシリトール、ステビオールグリコシド、レバウジオシド、モグロシド、スクラロース、アセスルファムK、アスパルテーム、およびそれらの任意の組み合わせからなる群から選択される、請求項12記載の使用。
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CNPCT/CN2018/101661 | 2018-08-22 | ||
CN2018101661 | 2018-08-22 | ||
PCT/EP2019/072356 WO2020038990A2 (en) | 2018-08-22 | 2019-08-21 | Terpene glycoside derivatives and uses thereof |
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JP2021533729A true JP2021533729A (ja) | 2021-12-09 |
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US (1) | US20210147892A1 (ja) |
EP (1) | EP3759228A2 (ja) |
JP (1) | JP2021533729A (ja) |
KR (1) | KR20210048439A (ja) |
CN (1) | CN112639116A (ja) |
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WO2021252814A1 (en) * | 2020-06-11 | 2021-12-16 | Corn Products Development, Inc. | Production and uses of oligosaccharides and steviol glycosides |
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KR20130014227A (ko) * | 2011-07-29 | 2013-02-07 | 한국생명공학연구원 | 신규한 α-글루코실 스테비오사이드 및 이의 제조 방법 |
JP2018509902A (ja) * | 2015-03-10 | 2018-04-12 | レイクスユニフェルシテイト フローニンゲン | ステビオールグリコシドの酵素的修飾方法、それによって得られる修飾ステビオールグリコシド、およびそれらの甘味料としての使用 |
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WO2018114995A1 (en) * | 2016-12-22 | 2018-06-28 | Dsm Ip Assets B.V. | Fermentation process for producing steviol glycosides |
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2019
- 2019-08-21 KR KR1020207028283A patent/KR20210048439A/ko unknown
- 2019-08-21 EP EP19762099.0A patent/EP3759228A2/en active Pending
- 2019-08-21 BR BR112020020365-3A patent/BR112020020365A2/pt unknown
- 2019-08-21 JP JP2020554457A patent/JP2021533729A/ja active Pending
- 2019-08-21 CN CN201980054637.XA patent/CN112639116A/zh active Pending
- 2019-08-21 WO PCT/EP2019/072356 patent/WO2020038990A2/en unknown
- 2019-08-21 US US17/045,141 patent/US20210147892A1/en active Pending
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JPH04149191A (ja) * | 1990-10-09 | 1992-05-22 | Nakano Vinegar Co Ltd | ステビオサイド糖転移化合物及びその製造方法 |
WO2005096839A1 (ja) * | 2004-04-05 | 2005-10-20 | Ajinomoto Co., Inc. | 澱粉含有食品の物性改良方法及び物性改良剤 |
KR20130014227A (ko) * | 2011-07-29 | 2013-02-07 | 한국생명공학연구원 | 신규한 α-글루코실 스테비오사이드 및 이의 제조 방법 |
JP2018509902A (ja) * | 2015-03-10 | 2018-04-12 | レイクスユニフェルシテイト フローニンゲン | ステビオールグリコシドの酵素的修飾方法、それによって得られる修飾ステビオールグリコシド、およびそれらの甘味料としての使用 |
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EP3759228A2 (en) | 2021-01-06 |
BR112020020365A2 (pt) | 2021-03-02 |
KR20210048439A (ko) | 2021-05-03 |
WO2020038990A3 (en) | 2020-04-16 |
CN112639116A (zh) | 2021-04-09 |
WO2020038990A2 (en) | 2020-02-27 |
US20210147892A1 (en) | 2021-05-20 |
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