Separation medium, use for separation medium, steviol glycoside separation method using separation medium, and steviol glycoside production method using separation method

12083,500

17/230082

April 14, 2021

An object of the present invention is to provide a separation medium and a separation method, ensuring high selectivity and good separation efficiency for specific steviol glycosides. The present invention is related to a separation medium in which polyethyleneimine is immobilized to porous particles of a (meth)acrylic polymer having a crosslinked structure and a hydroxyl group.

Mitsubishi Chemical Corporation (Tokyo, JP)

Mitsubishi Chemical Corporation (Tokyo, JP)

1. A separation method for steviol glycosides, comprising: loading a solution including two or more types of steviol glycosides to a separation medium; and allowing a solvent A to flow through the separation medium such that at least two types of steviol glycosides in the steviol glycosides are separated, wherein the separation medium comprises polyethyleneimine immobilized to porous particles of a (meth)acrylic polymer having a crosslinked structure, a diol structure, and a hydroxyl group.

2. The separation method for steviol glycosides according to claim 1 , wherein the solution includes rebaudioside A such that at least one fraction is a fraction including the rebaudioside A as a main component.

3. The separation method for steviol glycosides according to claim 1 , wherein the solvent A comprises alcohols freely miscible with water.

4. The separation method for steviol glycosides according to claim 1 , further comprising: conducting a decolorization of a pigment component in the solution.

5. A separation method for steviol glycosides, comprising: separating at least two types of steviol glycosides in two or more types of steviol glycosides by using a separation medium, wherein the separation medium includes a diol structure and polyethyleneimine immobilized to porous particles of a (meth)acrylic polymer.

6. The separation method for steviol glycosides according to claim 5 , wherein a mass average molecular weight of the polyethyleneimine is 200 or more.

7. The separation method for steviol glycosides according to claim 5 , wherein a nitrogen content rate of the separation medium is in a range of from 0.3 to 30% by mass.

8. The separation method for steviol glycosides according to claim 5 , wherein a pore diameter of the porous particles is in a range of from 1 to 1,000 nm.

9. The separation method for steviol glycosides according to claim 5 , wherein the (meth)acrylic polymer has a crosslinked structure and a hydroxyl group.

10. A production method for steviol glycosides, comprising: the separation method of claim 5 .

11. The separation method for steviol glycosides according to claim 2 , wherein the solvent A comprises alcohols freely miscible with water.

12. The separation method for steviol glycosides according to claim 2 , further comprising: conducting a decolorization of a pigment component in the solution.

13. The separation method for steviol glycosides according to claim 3 , further comprising: conducting a decolorization of a pigment component in the solution.

14. The separation method for steviol glycosides according to claim 6 , wherein a nitrogen content rate of the separation medium is in a range of from 0.3 to 30% by mass.

15. The separation method for steviol glycosides according to claim 6 , wherein a pore diameter of the porous particles is in a range of from 1 to 1,000 nm.

16. The separation method for steviol glycosides according to claim 6 , wherein the (meth)acrylic polymer has a crosslinked structure and a hydroxyl group.

17. A production method for steviol glycosides, comprising: the separation method of claim 6 .

18. The separation method for steviol glycosides according to claim 7 , wherein a pore diameter of the porous particles is in a range of from 1 to 1,000 nm.

19. The separation method for steviol glycosides according to claim 7 , wherein the (meth)acrylic polymer has a crosslinked structure and a hydroxyl group.

20. A production method for steviol glycosides, comprising: the separation method of claim 7 .

4772635 September 1988 Mitschker
5190660 March 1993 Lindoy et al.
6260715 July 2001 Simard
20080203029 August 2008 Deorkar et al.
20110183056 July 2011 Morita et al.
20140187761 July 2014 Morita et al.
20140194543 July 2014 Deorkar et al.
20160058050 March 2016 Morita et al.
20180077959 March 2018 Morita et al.
20190357581 November 2019 Morita et al.
20210037864 February 2021 Morita et al.
102060891 May 2011
102216313 October 2011
102603984 July 2012
104098734 October 2014
105440197 March 2016
60-160823 August 1985
2-251251 October 1990
5-86205 April 1993
5-86206 April 1993
2008-528966 July 2008
2012-504552 February 2012
2017-211352 November 2017

Lv, X. et al “Preparative separation of steviol gycosides . . . ” Acta Chromatog., vol. 26, pp. 123-135. (Year: 2014). cited by examiner
Shi, Y. et al “An efficient for decoloration of polysaccharides . . . ” Food Chem., vol. 217, pp. 461-467. (Year: 2017). cited by examiner
International Search Report issued May 29, 2018 in PCT/JP2018/006320 filed Feb. 21, 2018 (with English translation). cited by applicant
Written Opinion issued May 29, 2018 in PCT/JP2018/006320 filed Feb. 21, 2018. cited by applicant
General columns catalog Shodex 2016-2017, Showa Denko Kabushiki Kaisha, 2016, pp. 22-23. cited by applicant
Diaion Manual 2 (Mitsubishi Chemical Corporation), 2016, pp. 302-305. cited by applicant
Zhang, R. et al., Hydrophilic modification gigaporous resins with poly (ethylenimine) for high-throughput proteins ion-exchange chromatography, Journal of Chromatography A, 2014, vol. 1343, pp. 109-118. cited by applicant
Zhou, W. et al., Synthesis of macroporous poly (glycidyl methacrylate) microspheres by surfactant reverse micelles swelling method, European Polymer Journal, 2007, vol. 43, pp. 4493-4502. cited by applicant
Ba, Jing et al., Separation of Rebaudiana A from Steviol glycoside using a polymeric adsorbent with multi-hydrogen bonding in a non-aqueous system, Journal of Chromatography B, 2014, vol. 971, pp. 141-149. cited by applicant
Yu, Y., et al., “Preparation of Mixed-mode Chromatography Supports Based on Gigaporous Polymer Microspheres”, Chin. J. Anal. Chem., vol. 44, No. 12, pp. 1874-1879 (2016). cited by applicant
Chen, B. et al., Purification and Preparation of Rebaudioside A from Steviol Glycosides Using One-Dimensional Hydrophilic Interaction Chromatography, Journal of Chromatographic Science, 2016, vol. 54, No. 8, pp. 1408-1414. cited by applicant
Combined Chinese Office Action and Search Report issued Apr. 8, 2022 in Patent Application No. 201880011416.X (with English machine translation and English translation of Category of Cited Documents), 23 pages. cited by applicant
Chinese Offices Action issued on Dec. 26, 2023 in Chinese Patent Application 201880011416.X, (with English translation) 27 pages. cited by applicant
Combined Chinese Office Action and Search Report issued Aug. 19, 2022, in corresponding Chinese Patent Application No. 201880011416.X (with English Translation), 23 pages. cited by applicant
Biotechnology, Malu, Morta Morta, Shanghai Wadade Academy Press, pp. 202-203. Dec. 31, 1991, (with English Translation). cited by applicant
“Application of Capillary Electrophoresis in Pharmaceutical Analysis”, Lewis, Sieam Northw., pp. 55-57. Oct. 31, 2013, (with English Translation). cited by applicant
Japanese Office Action issued Jul. 6, 2021 in Japanese Patent Application No. 2019-501390 (with unedited computer generated English translation), 5 pages. cited by applicant
Combined Chinese Office Action and Search Report issued Sep. 30, 2021 in Patent Application No. 201880011416.X (with English language translation), 23 pages. cited by applicant

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