JPWO2020249746A5

JPWO2020249746A5 -

Info

Publication number: JPWO2020249746A5
Application number: JP2021573335A
Authority: JP
Publication date: 2023-06-19

Description

抽出物の遊離サッカライド化合物の力価(TSRL)は、以下の式で示す：

［式中、QSRLはmg/mlで、pe₃はmgで示す］。
さらに、本願発明は次の態様を含む。
［１］ローソンが豊富な抽出物の調製方法であって、：
a) ヘンナの地上部に元々存在するグリコシル化ローソン誘導体、例えばヘンノシド類を部分的にまたは完全に酵素的に加水分解するためにヘンナの地上部をpH 4～8の範囲の水に浸漬し、ローソンを含有する水溶液を提供する工程;
b) 工程a)で得られた溶液に有機溶媒を添加して水相および有機相を提供する工程であって、該有機溶媒は、C ₄ -C ₁₂ 直鎖または分岐鎖のアルコールから選択される工程;
c) 工程b)から得られた有機相を収集する工程;および
d) 工程c)で収集された有機相を濃縮し、ローソンが豊富な抽出物を得る工程、
を含む方法。
［２］工程(a)が、20℃～60℃の範囲の温度で行われる、［１］に記載の方法。
［３］工程a)が、pH 5～7.5の範囲で行われる、［１］または［２］に記載の方法。
［４］酸または塩基の添加による水溶液または水相のpHを変更させるいかなる工程も含まない、［１］～［３］のいずれか一項に記載の方法。
［５］工程a)が、攪拌下で15分間～2時間行われる、［１］～［４］のいずれか一項に記載の方法。
［６］工程a)が、浸漬の対象となるヘンナの地上部の重量より2～15倍大きい容量の水中で行われる、［１］～［５］のいずれか一項に記載の方法。
［７］有機溶媒が、生物資源のアルコールである、［１］～［６］のいずれか一項に記載の方法。
［８］有機溶媒が、C ₄ -C ₈ 直鎖または分枝鎖のアルコールまたはこれらの混合物であり、好ましくは、有機溶媒が、n-ブタノール、sec-ブタノール、イソブタノールおよびこれらの混合物からなる群から選択される、［１］～［７］のいずれか一項に記載の方法。
［９］工程d)で得られるローソンが豊富な抽出物が、ヘンナの地上部に元々存在するローソンの50％を超えて含み、該ローソンは、浸漬の対象となるヘンナの地上部において遊離形態、またはヘンノシド類などのグリコシル化誘導体の形態のどちらか一方である、［１］～［８］のいずれか一項に記載の方法。
［１０］さらに、工程c)およびd)の間に工程c')を含み、該工程c'は、工程c)で収集された有機相に担体を添加することを含み、工程d)の後に抽出物を乾燥させる工程e)を含み、ローソンが豊富な乾燥抽出物を提供する、［１］～［９］のいずれか一項に記載の方法。
［１１］工程d)で得られる、ローソンが豊富な抽出物が、乾燥抽出物の総重量に対して7重量％～60重量％のローソンを含有し、ルテオリン、アピゲニンおよび2,3,4,6-テトラヒドロキシアセトフェノンをさらに含む、［１］～［９］のいずれか一項に記載の方法。
［１２］工程d)で得られる、ローソンが豊富な抽出物が、クマル酸および／またはグリコシル化ルテオリン、特にルテオリン-6-C-ネオヘスペリドシドをさらに含む、［１］～［９］および［１１］のいずれか一項に記載の方法。
［１３］工程d)で得られる、ローソンが豊富な抽出物が、乾燥抽出物の総重量に対して2重量％を超えるタンパク質、ペプチドまたはアミノ酸を含まない、［１］～［９］および［１１］および［１２］のいずれか一項に記載の方法。
［１４］工程e)で得られる、ローソンが豊富な乾燥抽出物が、乾燥抽出物の総重量に対して0.6重量％～1.4重量％のローソンを含有し、ルテオリン、アピゲニンおよび2,3,4,6-テトラヒドロキシアセトフェノンをさらに含む、［１０］に記載の方法。
［１５］工程e)で得られる、ローソンが豊富な乾燥抽出物がさらに、ローソンが豊富な乾燥抽出物の総重量に対して、
0.05重量％～1.0重量％のルテオリン、
0.01重量％～0.5重量％のアピゲニン、および
0.05重量％～1.0重量％の2,3,4,6-テトラヒドロキシアセトフェノン、を含有する、［１４］に記載の方法。

The extract free saccharide compound potency (TSRL) is given by the following formula:

[wherein QSRL is in mg/ml and pe ₃ is in mg].
Furthermore, the present invention includes the following aspects.
[1] A method for preparing a Lawsone-enriched extract, comprising:
a) immersing the aerial parts of henna in water in the pH range of 4 to 8 to partially or completely enzymatically hydrolyze the glycosylated lawsone derivatives, such as hennosides, naturally present in the aerial parts of henna; providing an aqueous solution containing Lawsone;
b) adding an organic solvent to the solution obtained in step a) to provide an aqueous phase and an organic phase, wherein the organic solvent is selected from C4-C12 linear or _branched alcohols _; process;
c) collecting the organic phase obtained from step b); and
d) concentrating the organic phase collected in step c) to obtain a Lawsone-enriched extract;
method including.
[2] The method according to [1], wherein step (a) is carried out at a temperature in the range of 20°C to 60°C.
[3] The method according to [1] or [2], wherein step a) is carried out at a pH range of 5 to 7.5.
[4] The method according to any one of [1] to [3], which does not include any step of altering the pH of the aqueous solution or aqueous phase by addition of acid or base.
[5] The method according to any one of [1] to [4], wherein step a) is performed under stirring for 15 minutes to 2 hours.
[6] The method according to any one of [1] to [5], wherein step a) is performed in a volume of water 2 to 15 times greater than the weight of the aerial part of the henna to be soaked.
[7] The method according to any one of [1] to [6], wherein the organic solvent is a biologically sourced alcohol.
[8] The organic solvent is a C4 _- C8 _linear or branched alcohol or mixture thereof, preferably the organic solvent consists of n-butanol, sec-butanol, isobutanol and mixtures thereof The method according to any one of [1] to [7], which is selected from the group.
[9] The lawsone-rich extract obtained in step d) contains more than 50% of the lawsone originally present in the aerial parts of the henna, said lawsone being in free form in the aerial parts of the henna subject to steeping. , or in the form of glycosylated derivatives such as hennosides.
[10] Further comprising step c') between steps c) and d), said step c' comprising adding a carrier to the organic phase collected in step c), and after step d) The method of any one of [1] to [9], comprising the step e) of drying the extract to provide a dry extract enriched in Lawsone.
[11] The Lawsone-rich extract obtained in step d) contains 7% to 60% by weight of Lawsone relative to the total weight of the dry extract, luteolin, apigenin and 2,3,4, The method according to any one of [1] to [9], further comprising 6-tetrahydroxyacetophenone.
[12] The Lawsone-rich extract obtained in step d) further comprises coumaric acid and/or glycosylated luteolin, in particular luteolin-6-C-neohesperidoside, [1] to [9] and The method according to any one of [11].
[13] The Lawsone-rich extract obtained in step d) does not contain more than 2% by weight of proteins, peptides or amino acids relative to the total weight of the dry extract, [1] to [9] and [ 11] and the method according to any one of [12].
[14] The dry extract rich in Lawsone obtained in step e) contains 0.6% to 1.4% by weight of Lawsone relative to the total weight of the dry extract, luteolin, apigenin and 2,3,4 The method of [10], further comprising ,6-tetrahydroxyacetophenone.
[15] The Lawsone-enriched dry extract obtained in step e) further comprises, relative to the total weight of the Lawsone-enriched dry extract,
0.05% to 1.0% by weight of luteolin;
0.01% to 0.5% apigenin by weight, and
The method according to [14], containing 0.05% to 1.0% by weight of 2,3,4,6-tetrahydroxyacetophenone.

Claims

A method of preparing a Lawsone-enriched extract, comprising:
a) Aerial parts of henna are immersed in water in the pH range of 4-8 to partially or fully enzymatically hydrolyze the glycosylated lawsone derivatives originally present in the aerial parts of henna, containing Lawsone. providing an aqueous solution that
b) adding an organic solvent to the solution obtained in step a) to provide an aqueous phase and an organic phase, wherein the organic solvent is selected from _C4 - _C12 linear or branched alcohols; process;
c) collecting the organic phase obtained from step b); and
d) concentrating the organic phase collected in step c) to obtain a Lawsone-enriched extract;
method including.

The method of claim 1, wherein step (a) is performed at a temperature in the range of 20°C to 60°C.

3. A method according to claim 1 or 2, wherein step a) is carried out at a pH range of 5-7.5.

A process according to any one of claims 1 to 3, which does not comprise any step of altering the pH of the aqueous solution or phase by adding acid or base.

Process according to any one of claims 1 to 4, wherein step a) is carried out under stirring for 15 minutes to 2 hours.

A method according to any one of claims 1 to 5, wherein step a) is carried out in a volume of water 2 to 15 times greater than the weight of the aerial part of the henna to be soaked.

The method according to any one of claims 1 to 6, wherein the organic solvent is a biosourced alcohol.

The method according to any one of claims 1 to 7, wherein the organic solvent is a _C4 - _C8 linear or branched alcohol or a mixture thereof.

the lawsone-rich extract obtained in step d) contains more than 50% of the lawsone originally present in the aerial parts of the henna, said lawsone being in free form in the aerial parts of the henna subject to steeping, or A method according to any one of claims 1 to 8, in one of the forms of glycosylated derivatives.

Further comprising step c') between steps c) and d), said step c' comprising adding a carrier to the organic phase collected in step c), and adding the extract after step d). 10. A method according to any one of claims 1 to 9, comprising a drying step e) to provide a dry extract enriched in Lawsone.

The Lawsone-rich extract obtained in step d) contains 7% to 60% Lawsone by weight relative to the total weight of the dry extract and contains luteolin, apigenin and 2,3,4,6-tetra The method of any one of claims 1-9, further comprising hydroxyacetophenone.

12. The method according to any one of claims 1 to 9 and 11, wherein the Lawsone-enriched extract obtained in step d) further comprises coumaric acid and/or glycosylated luteolin .

13. Any of claims 1-9 and 11 and 12, wherein the Lawsone-enriched extract obtained in step d) does not contain more than 2% by weight of proteins, peptides or amino acids relative to the total weight of the dry extract. The method according to item 1.

The dry extract rich in lawsone obtained in step e) contains 0.6% to 1.4% by weight of lawsone relative to the total weight of the dry extract and contains luteolin, apigenin and 2,3,4,6- 11. The method of claim 10, further comprising tetrahydroxyacetophenone.

The Lawsone-enriched dry extract obtained in step e) further comprises, relative to the total weight of the Lawsone-enriched dry extract,
0.05% to 1.0% by weight of luteolin;
0.01% to 0.5% apigenin by weight, and
15. The method of claim 14, containing 0.05% to 1.0% by weight of 2,3,4,6-tetrahydroxyacetophenone.