WO2019099118A1 - Molécules dérivées de la stévia, procédés d'obtention de telles molécules, et leurs utilisations - Google Patents

Molécules dérivées de la stévia, procédés d'obtention de telles molécules, et leurs utilisations Download PDF

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Publication number
WO2019099118A1
WO2019099118A1 PCT/US2018/054631 US2018054631W WO2019099118A1 WO 2019099118 A1 WO2019099118 A1 WO 2019099118A1 US 2018054631 W US2018054631 W US 2018054631W WO 2019099118 A1 WO2019099118 A1 WO 2019099118A1
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WO
WIPO (PCT)
Prior art keywords
stevia
molecules
shows
rebaudioside
glycosides
Prior art date
Application number
PCT/US2018/054631
Other languages
English (en)
Inventor
Siddhartha Purkayastha
Avetik Markosyan
Siew Yin CHOW
Indra Prakash
John Clos
Ivory Xingyu PENG
Michael Z. Kagan
Steven F. Sukits
Kasi V. SOMAYAJULA
Khairul NIZAM BIN NAVI
Original Assignee
Purecircle Usa Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from PCT/US2017/061581 external-priority patent/WO2018090020A1/fr
Application filed by Purecircle Usa Inc. filed Critical Purecircle Usa Inc.
Priority to MX2020005404A priority Critical patent/MX2020005404A/es
Priority to JP2020526346A priority patent/JP2021502812A/ja
Priority to US16/764,336 priority patent/US11453693B2/en
Priority to BR112020009601-6A priority patent/BR112020009601A2/pt
Priority to CN201880079430.3A priority patent/CN112368303B/zh
Priority to EP18878508.3A priority patent/EP3710488A4/fr
Publication of WO2019099118A1 publication Critical patent/WO2019099118A1/fr
Priority to JP2022186793A priority patent/JP7431305B2/ja
Priority to JP2022186841A priority patent/JP7431306B2/ja
Priority to JP2024013964A priority patent/JP2024036456A/ja

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/256—Polyterpene radicals

Definitions

  • Rebaudioside A and stevioside have garnered the most commercial interest and have been extensively studied and characterized in terms of their suitability as commercial high intensity sweeteners. Stability studies in carbonated beverages confirmed their heat and pH stability (Chang S. S., Cook, J. M. (1983) Stability studies of stevioside and rebaudioside A in carbonated beverages. J. Agric. Food Chem. 31 : 409-412.)
  • FIG. 7 shows the structure of RSG4 (Related Steviol Glycoside 4).
  • FIG. 9 shows the structure of RSG6 (Related Steviol Glycoside 6).
  • FIG. 12 shows the structure of Rebaudioside 02.
  • FIG. 16 shows the structure of Rebaudioside U2.
  • FIG. 18 shows the structure of Rebaudioside V.
  • FIG. 22 shows the structure of RSG7 (Related Steviol Glycoside 7).
  • FIG. 24 shows the structure of Rebaudioside U3.
  • stevia-derived molecules shall refer to molecules obtained from any part of the plants of any variety of the species Stevia rebaudiana.
  • Methods of obtaining stevia-derived molecules include the methods used to extract steviol glycosides from Stevia plant leaves. Other methods may include extraction from other parts of the plant, or other extraction techniques and solvents.
  • the analytical system proved to be very sensitive towards changes in solvent composition and retention time shifts were observed when a new batch of solvents was used. Therefore, reference samples were analyzed before and after every analytical batch and the assignment of retention times was verified.
  • Stevia leaf extract A95 (100 g, white powder) were dissolved in ethanol/water 70/30 (750 ml_) at a temperature of 65°C.
  • the milky solution was allowed to cool down to room temperature in a water bath and then filtrated through a suction filter.
  • the collected crystals were washed with ethanol, dried and stored. Mother liquor and wash solution were kept separate and the respective solvent was removed under vacuum.
  • the respective sample (20 g) is dissolved in methanol, silica (40 g) is added and the solvent removed by a rotary evaporator.
  • the immobilized sample is transferred into a glass column and built into the high pressure liquid chromatography (HPLC) system described in Table 4. Air is removed from the transfer column by washing with Ethyl acetate/methanol 1 :1.
  • a time based fractionation leads to 90 fractions (0.5 min each) which are combined based on the UV and ELSD data generated during fractionation. Resulting fractions are analyzed by LCMS. Solvents and gradients are described in Table 4.
  • Isolated compounds were identified by NMR spectroscopy using a Bruker 500 Mhz NMR spectrometer. Identification of the aglycon was based on reference 1 H-NMR spectra using C17, C18 and C20 proton signals as primary indicators. Especially C20 proton shifts indicated alterations as seen in compounds #4 and #18. Glycosides were elucidated using H-H-Cosy, HSQC and HMBC and experiments using spectra of literature known steviosides as reference. 1.9 Results
  • Figure 1 shows the HPLC chart containing the major peaks identified in Table 7 by using analytical methodology as described above. The schematic steps to isolate different compounds in Table 7 are shown in Figure 2 and Figure 3.
  • Example 1 100 g stevia leaf extract A95 were recrystallized according to the method described in section 1.3 (Example 1) yielding 33.2 g of enriched minor compounds from mother liquor.
  • the enriched minor compounds were fractionated using normal phase chromatography as described in section 1.5 using gradient A (see Table 4).
  • Fractions 49-60 yielded 1.32 g of enriched minor compounds which were further fractionated using reversed phase HPLC according to section 1.4 using gradient L.
  • RP Reversed Phase
  • each of these minor molecules identified above preferably at purity levels ranging from 80-99%, including 90-95% purity, 99% purity, and 89% purity and higher, either as isolated or in combination with other stevia-derived molecules, are believed to have numerous desirable effects on the sweetness, taste and flavor profiles of products containing stevia-based ingredients.
  • These molecules can be useful in imparting specific tastes or modifying flavors, or both, in food, beverage, nutraceutical, pharmaceutical, and other comestible or consumable products.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Seasonings (AREA)

Abstract

L'invention concerne une composition purifiée de molécules de glycoside de stéviol. La composition confère des propriétés souhaitables de goût, d'arôme et de modification de l'arôme, à des aliments, boissons et autres produits de consommation.
PCT/US2018/054631 2016-11-14 2018-10-05 Molécules dérivées de la stévia, procédés d'obtention de telles molécules, et leurs utilisations WO2019099118A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
MX2020005404A MX2020005404A (es) 2016-11-14 2018-10-05 Moleculas derivadas de stevia, metodos para obtener tales moleculas y usos de las mismas.
JP2020526346A JP2021502812A (ja) 2016-11-14 2018-10-05 ステビア由来分子、そのような分子を得る方法、及びその使用
US16/764,336 US11453693B2 (en) 2016-11-14 2018-10-05 Stevia-derived molecules, methods of obtaining such molecules, and uses of the same
BR112020009601-6A BR112020009601A2 (pt) 2016-11-14 2018-10-05 moléculas derivadas de estévia, métodos para obtenção dessas moléculas, e usos das mesmas
CN201880079430.3A CN112368303B (zh) 2016-11-14 2018-10-05 甜叶菊衍生的分子，获得此类分子的方法，及其用途
EP18878508.3A EP3710488A4 (fr) 2017-11-14 2018-10-05 Molécules dérivées de la stévia, procédés d'obtention de telles molécules, et leurs utilisations
JP2022186793A JP7431305B2 (ja) 2016-11-14 2022-11-22 ステビア由来分子、そのような分子を得る方法、及びその使用
JP2022186841A JP7431306B2 (ja) 2016-11-14 2022-11-22 ステビア由来分子、そのような分子を得る方法、及びその使用
JP2024013964A JP2024036456A (ja) 2016-11-14 2024-02-01 ステビア由来分子、そのような分子を得る方法、及びその使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PCT/US2017/061581 WO2018090020A1 (fr) 2016-11-14 2017-11-14 Molécules dérivées de la stevia, procédés d'obtention de telles molécules, et leurs utilisations
USPCT/US2017/061581 2017-11-14

Publications (1)

Publication Number Publication Date
WO2019099118A1 true WO2019099118A1 (fr) 2019-05-23

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EP (1) EP3710488A4 (fr)
WO (1) WO2019099118A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160198748A1 (en) * 2013-05-28 2016-07-14 Purecircle Sdn Bhd High-Purity Steviol Glycosides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11447516B2 (en) * 2016-10-04 2022-09-20 The Coca-Cola Company Diterpene glycosides containing an ent-atisene core, compositions and methods

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160198748A1 (en) * 2013-05-28 2016-07-14 Purecircle Sdn Bhd High-Purity Steviol Glycosides

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE PubChem 26 October 2006 (2006-10-26), Database accession no. 11088897 *
IBRAHIM ET AL.: "Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana", J. NAT. PROD., vol. 77, 2014, pages 1231 - 1235, XP055340471 *
See also references of EP3710488A4 *

Also Published As

Publication number Publication date
EP3710488A4 (fr) 2021-08-25
EP3710488A1 (fr) 2020-09-23

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