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Terpene glycoside derivatives and uses thereof

A technology for terpene glycosides and terpene glycosides, applied in the field of terpene glycosides, can solve problems such as bad taste attributes, preventing widespread adoption, etc.

Pending Publication Date: 2021-04-09
FIRMENICH SA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many currently disclosed glucosylated low-calorie sweeteners continue to exhibit undesirable taste attributes, preventing their widespread adoption

Method used

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  • Terpene glycoside derivatives and uses thereof
  • Terpene glycoside derivatives and uses thereof
  • Terpene glycoside derivatives and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] Example 1: Generation of mono-α-1,6-glucosylated stevioside compounds (compounds I and II)

[0118] At room temperature, rubusoside (2 g) and corn maltodextrin (2 g) with a dextrose equivalent (DE) of 18 were dissolved in 10 ml of NaOAc-HOAc (pH=6.0, 0.2 M, 10 mL) buffer or removed ionized water. Subsequently, 100 µl of transglucosidase L (Amano) was added to the mixture. The enzyme-containing mixture was then heated to 60°C and incubated at 60°C for 24 hours to allow the transglucosidation reaction to proceed, resulting in a glucosidase with a single α-1,6 glucosidic bond. Glycosylated terpene glycosides. The reaction was stopped by inactivating the transglucosidase by incubating the reaction mixture at 100°C for 30 minutes.

[0119] The resulting reaction mixture was analyzed by UPLC-UV and a mixture containing glucosylated terpene glycosides with a single α-1,6 glucosidic linkage was identified (see figure 1 ). The identified mixture was purified by preparative...

Embodiment 2

[0120] Example 2: Generation of mono-alpha-1,6-glucosylated stevioside compounds (compounds I and II) by methods according to some morphologies presented herein, using rubusoside and maltose as starting materials

[0121] Rubusoside (2 g) and maltose (2 g) were dissolved in 10 ml of NaOAc-HOAc (pH=6.0, 0.2 M, 10 mL) buffer or deionized water at room temperature. Subsequently, 100 μL of transglucosidase L (Amano) was added to the mixture. The enzyme-containing mixture was then heated to 60°C and incubated at 60°C for 24 hours to allow the transglucosidation reaction to proceed, resulting in a glucosidase with a single α-1,6 glucosidic bond. Glycosylated terpene glycosides. The reaction was stopped by inactivating the transglucosidase by incubating the reaction mixture at 100°C for 30 minutes.

[0122] The resulting reaction mixture was analyzed by UPLC-UV and a mixture containing glucosylated terpene glycosides with a single α-1,6 glucosidic linkage was identified (see figu...

Embodiment 3

[0123] Example 3: Generation of mono-alpha-1,6-glucosylated rebaudioside A (Compound III) by methods according to some morphologies presented herein, using rebaudioside as starting material

[0124] Rebaudioside A (2 g) and corn maltodextrin (2 g) with a dextrose equivalent (DE) of 18 were dissolved in 10 ml of deionized water at room temperature. Subsequently, 100 µl of transglucosidase L (Amano) was added to the mixture. The enzyme-containing mixture was then heated to 60°C and incubated at 60°C for 24 hours to allow the transglucosidation reaction to proceed, resulting in a glucosidase with a single α-1,6 glucosidic bond. Glycosylated terpene glycosides. The reaction was stopped by inactivating the transglucosidase by incubating the reaction mixture at 100°C for 30 minutes.

[0125] The resulting reaction mixture was analyzed by UPLC-UV, and glucosylated terpene glycosides with a single α-1,6 glucosidic linkage were identified (see image 3 ). The identified mixture was...

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Abstract

The present disclosure relates generally to terpene glycosides, such as certain such compounds extracted from Stevia rebaudiana Bertoni, Rubus suavissimus, or Siraitia grosvenorii. The disclosure also provides for the use of such compounds as food ingredients, flavors, and sweeteners, and related methods. The disclosure also provides ingestible compositions comprising such compounds, as well as processes for extracting such compounds selectively from certain plant sources.

Description

[0001] Cross References to Related Applications [0002] This application claims priority from PCT Application PCT / CN2018 / 101661 filed on August 22, 2018, the entire contents of which are hereby incorporated by reference in their entirety. technical field [0003] The present disclosure generally relates to terpene glycosides, such as certain such compounds extracted from Stevia rebaudiana Bertoni, Rubus suavissimus, or Siraitia grosvenorii. The present disclosure also provides the use of such compounds as food ingredients, flavorings and sweeteners, and related methods. The present disclosure also provides ingestible compositions comprising such compounds, and methods of selectively extracting such compounds from certain plant sources. Background technique [0004] The gustatory system provides sensory information about the chemical composition of the outside world. Taste transduction is a more complex form of chemically triggered sensation in animals. Taste signals are ...

Claims

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Application Information

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IPC IPC(8): C12P19/18A23L27/30C12P19/44
CPCC12P19/18C12P19/44A23L27/36A23L2/60A23L23/00A23L7/135A23L33/40A23G1/56A23D7/0056A23G4/00A23G1/50A23D7/0053
Inventor 印丹婷甘贤文
Owner FIRMENICH SA
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