Terpene glycoside derivatives and uses thereof

A technology of 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: 2020-12-11
FIRMENICH SA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many currently disclosed glycated 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

[0105] Example 1: Generation of mono-β-1,4-glucosylated terpene glycoside compounds (compounds I and II) starting from rubusoside by methods according to some morphologies proposed herein

[0106] Rubusoside (1 g) and cellobiose (1 g) were dissolved in 10 ml of NaOAc-HOAc (pH=5.0, 0.2 M, 5 mL) buffer at room temperature. Subsequently, 200 mg of cellulase (Aladdin) was added to the mixture. The enzyme-containing mixture was then heated to 37°C and incubated at 37°C for 24 hours to allow the transglucosidation reaction to proceed to produce a At least one glucosylated terpene glycoside of a single glucosyl residue linked to an glycoside. The reaction was terminated by inactivating the cellulase by incubating the reaction mixture at 100°C for 30 minutes.

[0107] The resulting reaction mixture was analyzed by UPLC-UV, and the mixture was identified to contain glucosylated terpene glycosides with a single glucosyl residue linked to the terpene glycoside via a β-1,4 glucosidic bo...

Embodiment 2

[0110] Example 2: Sensory properties of compositions comprising compounds I and II

[0111] According to the method described in Example 1, a composition comprising a mixture of a compound of formula I and a compound of formula II in a ratio (w / w) of 2:1 was produced. The composition was dissolved in (i) a 4% w / w solution of sucrose, or (ii) a 0.02% w / w solution of 95% steviol glycosides. A panel of 25 trained individuals rated them on a scale of -5 to 5 (-5 being no effect, 5 being very strong effect, 0 being the strength of a reference aqueous solution containing (i) 4% w / w sucrose solution or (ii) 0.02% w / w of 95% steviol glycoside solution) to evaluate the taste characteristics (sweet, licorice and sweetness residue) of the test solution. The results are shown in the table below.

[0112]

[0113] These data show that a composition comprising Compounds I and II in a 2:1 ratio significantly enhanced the sweetness intensity of a 4% w / w sucrose solution with and without ...

Embodiment 3

[0114] Example 3: Sensory properties of compositions comprising at least one mono-β-1,4-glucosylated terpene glycoside proposed herein

[0115]Compositions comprising at least one glucosylated terpene glycoside can be produced according to the method described in Example 1. The composition can be dissolved in (i) water, or (ii) 4% w / w sucrose solution, or (iii) 7% (w / w) invert sugar plus 0.15% citric acid (w / w ) solution, wherein the final concentration of the composition in the solution ranges from 0 to 1000 ppm. Corresponding control solutions will also be produced, respectively (i) 1.5%, or (ii) 4% w / w sucrose, or (iii) 7% (w / w) invert sugar plus 0.15% citric acid (w / w) solution. A panel of 10 experts will use the 3-Alternative Forced Choice (3-AFC) or sweetness intensity scale to evaluate the difference between the test composition solution and the sucrose solution. All samples will be tested blind in random order.

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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 alsoprovides 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 / 108629 filed September 29, 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/08C07H13/08A23L2/60
CPCC07H13/08A23L2/60C07H1/08A23L27/36C12N9/2437C12P19/14C12Y302/01004A23V2002/00C12P19/56
Inventor 甘贤文
Owner FIRMENICH SA
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