JP6814182B2 - A novel tripelten glycoside used as a sweetener or sweetener - Google Patents

Description

The present invention is a novel available from an extract of a sweetener or sweetening agent, particularly a preparation or composition that can be used as an edible composition, Momordica grosvenorii (Siraitia grosvenori) or a physiologically acceptable salt thereof. Regarding tripelten glycoside compounds.

Sweetness is one of the major tastes sought by humans and animals. International uses of sweets that are naturally or synthetically produced to meet this naturally occurring requirement without physiological disadvantages such as obesity, nutritional imbalances, tooth decay, etc. have yet been discovered. Not. To solve this problem, there is considerable research and expense to develop substitutable compounds, such as to produce compounds that are low in nutritional value, calorie-free, and replaceable with natural or synthetic sweeteners. It was thrown in. These artificial sweeteners have a wide range of uses, meet the requirements of low nutritional value but sweetness, and can be used without adding calories and damaging the teeth, but artificial sweeteners are, for example, their toxicity (p. -Ethoxyphenylurea), chromosomal or bladder disorders (sodium cyclamate), and other unique challenges are often discovered. Therefore, the above artificial sweeteners are not recommended for use as sweeteners and are seemingly unsuitable for consumption. Saccharin compounds are also commonly used as artificial sweeteners because the use of cyclo compounds is restricted by the government. The saccharin compound also has sweetness characteristics, but in most cases, the saccharin compound alone has a sweetness because a bitter taste remains in the consumer's mouth for a long time after consumption of the food or beverage composition containing the compound. It is not desired to be used as a fee. For many years, saccharin and cyclo have been used as artificial sweeteners, but in recent years new groups of artificial sweeteners have been discovered.

For example, US Pat. No. 3,087,821 (Horowitz and Gentili) discloses the use of various dihydrochalcones with saccharide substituents (dihydrochalcone glycosides) as sweeteners. All sweet dihydrochalcones have a licorice-like aftertaste and remain in the mouth for a period of time.

U.S. Pat. No. 3,087,821

Siraitia grosvenorii (Luo Han Guo) is a member of the Cucurbitaceae family and grows in South Asia and China. The sweetness of Luohango is due to the triterpene glycoside, also known as mogroside. Although multiple mogrosides are identified in Luohango, the concentration of mogroside V (CAS No: 88901-36-4) is higher than that of other mogrosides when compared with the concentration of other mogrosides. Mogrol glycosides have the same core molecule, mogrol or oxomogrol, and differ from each other in the number and type of residual glycosides bound to mogrol or oxomogrol (US Patent Publication No. 2012/0059071, Journal "Chemistry". Biology (1989), pp. 3347-3349, magazine "Chemical Pharmaceutical Bulletin" (1990), pp. 2030-2032.) Some mogrosides have a strong sweetness, and in most cases the common tripelten glycosides of Luo Han Guo (Siraitia grosvenori), mogroside V and its isomer, isomogroside V (see US Patent Publication No. 2011/0027413). It is 100 times sweeter than the sweetness of sucrose including sucrose, but all have a certain bitterness after eating.

Typical mogrosides in Luohango fruit are listed in Table A below.

The leaves of Stevia rebaudiana are known for their sweetness because they contain a sweet diperten glycoside. Rebaudioside A, the main sweetening compound derived from Stevia, has been approved for use as a natural sweetener in the United States (since 2008) and Europe (2011). With the exception of that sweetness, all stevia-derived sweeteners develop a slower sweetness, lasting longer than sugar and, at higher concentrations, with a licorice-like bitter aftertaste (Lemus-Mondaca et al). . Food Chemistry 132 (2012) 1121-1132)).

Other examples relate to triterpenes and triterpene glycosides and / or physiologically acceptable salts thereof disclosed in Symrise European Patent Publication No. 2529633. Triterpenes are preferably the naturally occurring triterpenes and triterpenes glycosides of Mycetia balansae, which produce a sweetness sensation with an orally consumable formulation or enhance sweetness with an orally consumable formulation. These triterpene glycosides differ from the triterpene structures described in the present invention.

Therefore, a main object of the present invention relates to novel sweeteners and physiologically acceptable salts thereof that provide beneficial sweetness to food compositions and oral compositions. In particular, the main purpose is a consumable composition with a relatively low balance between the degree of sweetness and the amount that must be taken to obtain sweetness in order to eliminate the disadvantages of conventional sweeteners. With respect to a sweetening composition that can give sweetness to. Another object relates to sweetener compounds that do not leave astringency or bitterness after eating. The identified sweetener compounds are non-toxic, safe, effective at low concentrations, tolerant of digestion, stable (especially in conventional cosmetic and / or drug formulations), and It is easy to formulate and can be produced economically.

After extensive research on sweeteners, the inventor of the present application succeeded in separating the sweetener compound of formula (I), and the sweetener compound of formula (I) was surprisingly compared with sucrose and mogroside V. It was found to produce a good and strong sweetness. Surprisingly, the sweetener compound of formula (I) has a very strong sweetness with significantly reduced unpleasant taste after consumption.

The present invention relates to a sweet compound having formula (I):

(I)
Here, R ₁ , R ₂ , and R ₃ are independent of each other and represent a sugar component selected from the group of hydrogen, hydroxyl, carbonyl or monosaccharide and / or oligosaccharide.

Preferably, in the sweetening compound of formula (I), the monosaccharide units of the monosaccharides and / or oligosaccharides are selected from the following groups: furanose, glucose, sucrose, xylose, maltose, mannose, lambnorse, galactose, Lactose, gentiobiose, sophorose, β-glucopyranoseyl- (1-2)-[β-glucopyranose- (1-6)]-β-glucopyranose, cellobiose, mannitol, sorbitol, xylitol or arabitol, glucuronic acid, quinobos, arabino Pyranose, arabinofuranose, xylopyranose, xylofranose and / or apiose (2,3,4-trihydroxy-3- (hydroxy-methyl) butanal), and oligosaccharides contain 2-5 units of monosaccharide units.

The term "monosaccharide" is one of the simplest sugars. Monosaccharides are the most basic unit of biologically important carbohydrates. Examples of monosaccharides include glucose (dexstrose), fructose (rebroth), galactose, xylose and ribose. Monosaccharides are constituents of disaccharides (sucrose, etc.) and polysaccharides (cellulose, starch, etc.). In addition, each carbon atom attached to a hydroxyl group (except for the first and last structures) is a chiral compound, increasing the number of isomer forms derived from the same compounding formula. For example, galactose and glucose are both aldohexoses, but each has different chemical and physical properties.

The term "oligosaccharide" refers to a saccharide consisting of at least 2-10 glycoside-linked monosaccharide polymers, preferably 2-5 units of monosaccharide units. In most cases, the oligosaccharide monosaccharides are glycosidic linked to each other.

The term "sugar component" has the same meaning as an element or unit constituting a sugar component.

The sugar component of the present invention may have the simplest structure and is preferably represented by the following formula (II).

Here, D is any of O, S, and N.

X, Y, and Z are independent of each other and represent hydrogen, hydroxyl, carbonyl, or other sugar components, which are other units represented by the formula (II). The sugar component is bound to formula (I) by an oxygen or nitrogen or sulfur atom, and more preferably to an oxygen atom represented by the integer D of formula (II). In a preferred embodiment of the invention, when R ₁ , R ₂ , and R ₃ are independent sugar components, the compounds are preferably bonded to each other by oxygen atoms.

The three-dimensional structure of monosaccharides is represented by the following four forms. a) The Fischer projection formula is a method for systematically expressing the skeletal formula of an acyclic monosaccharide, and can express the hardness of each asymmetric carbon (chiral carbon). Each stereoisomer of a simple chain monosaccharide is identified by its position (right or left) in the Fischer projection of a chiral hydroxyl (hydroxyl group attached to an asymmetric carbon).
b) Haworth projection: In the Haworth projection, the α-isomer has -OH of anomer carbon downward with respect to the plane of the carbon atom, and the β-isomer has the -OH of the anomer carbon upward with respect to the plane of the carbon atom. It has -OH of anomeric carbon. Pyranose, like cyclohexane, typically has a chair conformation. In this structure, the α-isomer has an anomeric carbon −OH at the axial position and the β-isomer has an anomeric carbon OH − at the equatorial plane position.
c) A more realistic structure is a chair-shaped structure, which represents a carbon chain with corners formed.
d) Absolute three-dimensional chemistry schemes, such as cyclohexane structure, are also common:

Different schemes of α-D-glucopyranose are trence (1), hearth (2), chair type (3), and absolute conformation (4). (Reference: Wikipedia: http://de.wikipedia.org/wiki/Monosaccharide)

For formula (II), since the sugar unit is illustrated as a planar moiety, the sugar unit of the present invention may have all possible steric isomers and is a primary specific isomer. Not restricted to the body.

It is a graph which shows H-NMR of compound Aa. It is a graph which shows the H-NMR of the compound Bb. It is a graph which shows the H-NMR of the compound Cc. It is a graph which shows the H-NMR of the compound Dd. It is a graph which shows the H-NMR of the compound Ee. It is a graph which shows the H-NMR of the compound Ff. It is a graph which shows the H-NMR of the compound Gg. It is a graph which shows the H-NMR of the compound Hh. It is a graph which shows the H-NMR of the compound Jj. It is a graph which shows the H-NMR of the compound Kk. It is a graph which shows the H-NMR of the compound Ll. It is a graph which shows the H-NMR of the compound Mm. It is a graph which shows ESI-MS of compound Aa. It is a graph which shows ESI-MS of compound Bb. It is a graph which shows ESI-MS of compound Cc. It is a graph which shows ESI-MS of compound Dd. It is a graph which shows ESI-MS of compound Ee. It is a graph which shows ESI-MS of compound Ff. It is a graph which shows ESI-MS of compound Gg. It is a graph which shows ESI-MS of compound Hh. It is a graph which shows ESI-MS of compound Jj. It is a graph which shows ESI-MS of compound Kk. It is a graph which shows ESI-MS of compound Ll. It is a graph which shows ESI-MS of compound Mm.

(1) In a preferred embodiment, the compound of formula (I) comprises at least one sugar unit of formula (II) (monosaccharide). In a preferred embodiment, the sugar unit of formula (II) is a repeating sugar unit of 2, 3, 4 or 5 times, each bound by the oxygen atom of the carbohydrate.

(2) In a preferred embodiment, the sugar unit of formula (II) is represented only once in formula (I), which is any of R ₁ , R ₂ , and R ₃ .

(3) In a preferred embodiment of the present invention, R ₁ and R ₂ of the formula (I) are independent of each other and are selected from the group containing hydrogen, hydroxyl, carbonyl or monosaccharide and / or oligosaccharide. Representing a component, R ₃ of the formula (I) represents hydrogen, hydroxyl or carbonyl. Preferred monosaccharide and / or oligosaccharide monosaccharide units are selected from the following groups: fructose, glucose, sucrose, xylose, maltose, mannose, lambnorse, galactose, lactose, gentiobiose, sophorose, β-glucopyranose- (1). -2)-[β-Glucopyranose- (1-6)]-β-glucopyranose, cellobiose, mannitol, sorbitol, xylitol or arabitol, glucuronic acid, quinobos, arabinopyranose, arabinofuranose, xylopyranose, xylofranose and / Or apiose (2,3,4-trihydroxy-3- (hydroxymethyl) butanal). Glucose, maltose, galactose, arabinopyranose and xylopyranose are particularly suitable, and particularly preferable sugar components are glucose, galactose, arabinopyranose and xylopyranose.

(4) In a preferred embodiment of the present invention, R ₁ and R ₂ of the formula (I) are independent and selected from the group containing hydrogen, hydroxyl, carbonyl or monosaccharide and / or oligosaccharide. Representing the ingredients, the group is selected from: fructose, glucose, sucrose, xylose, maltose, mannose, lambnorse, galactose, lactose, cellobiose, gentiobiose, sophorose, β-glucopyranose- (1-2)-[ β-Glucopyranose- (1-6)]-β-Glucopyranose, mannitol, sorbitol, xylitol or arabitol, glucuronic acid, quinobos, arabinopyranose, arabinofuranose, xylopyranose, xylofranose and / or apiose (2,3) , 4-Trihydroxy-3- (hydroxymethyl) butanal). R ₃ of formula (I) represents hydrogen, hydroxyl or carbonyl.

(5) Preferred sugar components are fructose, glucose, sucrose, maltose, galactose, arabinopyranose and xylopyranose, and particularly preferred sugar components are glucose, arabinopyranose and xylopyrannose.

(6) In another embodiment, R ₁ and R ₂ of the formula (I) are independent monosaccharides, preferably glucose and / or arabinopyranose and / or xylopyranose.

(7) In another embodiment, R ₁ and R ₂ of the formula (I) are independent oligosaccharides, and the monosaccharide units are preferably glucose and / or galactose and / or arabinopyranose and / or. Xylopyranose. Preferably, the oligosaccharide has 1, 2, 3 or 4 units of glucose and / or galactose and / or arabinopyranose and / or xylopyranose. More preferably, the oligosaccharide is 1, 2 or 3 units of glucose.

(8) In another preferred embodiment, R ₃ is hydrogen and R ₁ and R ₂ of formula (I) are independent and contain hydrogen, hydroxyl, carbonyl or monosaccharide and / or oligosaccharide. Represents the sugar component selected from. Monosaccharides and / or oligosaccharides include fructose, glucose, sucrose, xylose, maltose, mannose, lambnorth, galactose, lactose, cellobiose, mannitol, sorbitol, xylitol or arabitol, glucuronic acid, quinovose, arabinopyranose, arabinofuranose, It is selected from the group of xylopyranose, xylofranose and / or apiose (2,3,4-trihydroxy-3- (hydroxymethyl) butanal).

(9) In another preferred embodiment, R ₃ is hydrogen and R ₁ and R ₂ of formula (I) are independent of each other, from the group containing monosaccharides and / or oligosaccharides having monosaccharide units. Represents the selected sugar component. Monosaccharides and / or oligosaccharides include fructose, glucose, sucrose, xylose, maltose, mannose, lambnorse, galactose, lactose, gentiobiose, sophorose, β-glucopyranose- (1-2)-[β-glucopyranose- (1-6). )]-Β-Glucopyranose, cellobiose, mannitol, sorbitol, xylitol or arabitol, glucuronic acid, quinobos, arabinopyranose, arabinofuranose, xylopyranose, xylofranose and / or apiose (2,3,4-trihydroxy- It is selected from the group of 3- (hydroxymethyl) butanal).

(10) In another preferred embodiment of the present invention, R ₁ and R ₂ of formula (I) are independent of each other and represent a sugar component selected from hydroxyl or monosaccharide and / or oligosaccharide.

The monosaccharide units of monosaccharides and / or oligosaccharides are selected from the following groups: glucose, 2-glucopyranosyl-glucose, 3-glucopyranosyl-glucose, 4-glucopyranosyl-glucose, 6-glucopyranosyl-glucose, or glucopyranosyl. -(1 → 2)-[Glucopyranosyl- (1 → 6)]-For glucose and oligosaccharides, the monosaccharide units of the oligosaccharides are glycoside-linked to each other, and
-R ₃ is hydrogen, hydroxyl or carbonyl.

(11) In another preferred embodiment, compound R ₂ of formula (I) is an oligosaccharide having 2 units of monosaccharide unit (disaccharide), and the disaccharide monosaccharide unit of R ₂ is 1 → 6. They are glycosidic bound to each other rather than bound to each other.

(12) In a more preferred embodiment, R ₂ is an oligosaccharide having 2 units of monosaccharide units (disaccharide) and R ₃ is hydrogen, hydroxyl or carbonyl.

(13) In a more preferred embodiment, R ₁ is hydrogen, hydroxyl, carbonyl or an oligosaccharide having 2, 3, 4 or 5 monosaccharide units and R ₂ is 2 units of monosaccharide unit (disaccharide). It is an oligosaccharide having, and R ₃ is a hydroxyl group.

(14) In a more preferred embodiment of the invention, when R ₂ is an oligosaccharide having three monosaccharide units (trisaccharides):
R ₁ is a carbonyl and / or R ₃ is not a hydroxyl or carbonyl, or R ₃ is a hydroxyl and R ₁ is an oligosaccharide having 2, 4 or 5 monosaccharide units. The monosaccharide unit of the oligosaccharide of R ₁ has a glycosidic bond, which is not a 1 → 6 bond or a 1 → 4 bond.

(15) In a more preferred embodiment of the invention, R ₁ is a monosaccharide or an oligosaccharide containing at least 3 monosaccharide units.
R ₂ is an oligosaccharide having 3 units of monosaccharide units (trisaccharides), and R ₃ is a carbonyl.

(16) In a more preferred embodiment of the invention, R ₁ is an oligosaccharide having 2, 4 or 5 units of monosaccharide units but not 3 units of monosaccharide units.

(17) In a more preferred embodiment of the invention, R ₂ is an oligosaccharide having 2-5 units of monosaccharide units, but not only (1 unit) of monosaccharides.

(18) In a more preferred embodiment of the invention, when R ₂ is a carbonyl,
・ R ₃ is not carbonyl,
-R ₃ is a hydroxyl group.

(19) In the sweetener compound of the formula (I) in a more preferable embodiment of the invention.
If R ₁ is a sugar component containing 2 units of sugar and R ₂ is a sugar component containing 3 units of sugar
R ₃ represents a group of hydrogen or carbonyl, preferably hydrogen, and / or the glycosidic bond in the sugar unit of R ₁ is mogroside V and iso-mogroside V having a disaccharide component is 1 → 4 or It has a 1 → 6 glycosidic bond, not a 1 → 2 glycosidic bond.

(20) In the sweetener compound of formula (I) in another preferred embodiment.
-R ₁ is a sugar component containing 2 units of sugar units, and-R ₂ is a sugar component containing 3 units of sugar units.
-R ₃ is hydrogen.

<Especially important compounds>
The most important compounds of formula (I) are shown below.
<Compound A>
3,11-Dihydroxy-4,4,9,13,14-Pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro- 1H-Cyclopentane [a] phenanthrene-17-yl) -2-hydroxy-2-methylheptane-3-yloxy) -4,5-dihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy)- 6- (Hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol

<Compound B>
4,5-Dihydroxy-2-(2-Hydroxy-2-methyl-6-((4,4,5,13,14-pentamethyl-3-(3,4,5-trihydroxy-6-((3)) , 4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10 , 11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6-((3,4,5-trihydroxy) -6- (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol

<Compound C>
4,5-Dihydroxy-3- (3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-((3,4,5-trihydroxy-6-) (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -4,4,9,13,14 -Pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro-1H-cyclopenta [a] phenanthrene-3-yloxy) -4, 5-Dihydroxy-2- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol

<Compound D>
2- (2- (17- (5- (4,5-dihydroxy-3- (3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6- ( (3,4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2- Il) -4,4,9,13,14-pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [A] Phenantren-3-yloxy) -4,5-dihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5 − Triol


<Compound E>
2- (4,5-Dihydroxy-2- (2-Hydroxy-2-methyl-6- (4,4,5,13,14-Pentamethyl-3- (3,4,5-Trihydroxy-6-) Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a] Phenantren-17-yl) heptane-3-yloxy) -6-((3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H- Piran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-piran-3,4,5-triol

<Compound F>
2-((6-(6-(3- (4,5-dihydroxy-6- (hydroxymethyl) -3- (3,4,5-dihydroxytetrahydro-2H-pyran-2-yloxy) tetrahydro-2H-) Pyran-2-yloxy) -11-Hydroxy-4,4,9,13,14-Pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17 -Tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-hydroxy-2-methylheptane-3-yloxy) -3,4-dihydroxy-5- (3,4,5-trihydroxy- 6- (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) tetrahydro-2H-pyran-2-yl) methoxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol

<Compound G>
2- (4,5-Dihydroxy-2- (2-Hydroxy-2-methyl-6- (4,4,5,13,14-Pentamethyl-3- (3,4,5-Trihydroxy-6-) Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a] Phenantren-17-yl) heptane-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5- Triol

<Compound H>
2-Hydroxy-6- (11-Hydroxy-4,4,9,13,14-Pentamethyl-3- (3,4,5-Trihydroxy-6-((3,4,5-Trihydroxy-6-) (Hydroxymethyl) Tetrahydro-2H-pyran-2-yloxy) Methyl) Tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15 , 16,17-Tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-methylheptane-3-one

<Compound J>
17- (5- (4,5-dihydroxy-3- (3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-((3,4,5) -Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -11-hydroxy -4,4,9,13,14-Pentamethyl-4,7,8,9,10,11,12,13,14,15,16,17-Dodecahydro-1H-cyclopenta [a] phenanthrene-3 (2H) ) -On


<Compound K>
2- (4,5-Dihydroxy-2- (2-Hydroxy-6- (3-Hydroxy-4,4,9,13,14-Pentamethyl-2,3,4,7,8,9,10,11) , 12,13,14,15,16,17-Tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-methylheptane-3-yloxy) -6-((3,4,5-yl) Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5 Triol

<Compound L>
17- (5- (4,5-dihydroxy-3- (3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-((3,4,5) -Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -4,4 , 9,13,14-Pentamethyl-3- (3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -3,4,7,8,9,10, 12, 13, 14, 15, 16, 17-dodecahydro-1H-cyclopenta [a] phenanthrene-11 (2H) -on


<Compound M>
2- (4,5-Dihydroxy-2- (2-Hydroxy-2-methyl-6- (4,4,5,13,14-Pentamethyl-3- (3,4,5-Trihydroxy-6-) Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a] Phenantren-17-yl) heptane-3-yloxy) -6-((3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H- Piran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-piran-3,4,5-triol

Compounds A to M have a planar structure, which is particularly preferred. This means that the displayed compounds A to M contain all isomers, which is possible with each compound. The isomer has the same number of atoms in each component, but the arrangement of atoms in space is different. The isomers need not have the same properties unless the functional groups are also the same. There are various groups of isomers such as positional isomers, cis-trans isomers, and enantiomers. There are mainly two types of isomers, structural isomers and steric isomers (spatial isomers).

Each isomer of the compounds A to M of the formula (I) is included in the above-mentioned structure and is preferable due to the nature of the present invention.

In particular, the following isomers are preferable for the compound of the formula (I).
<Compound Aa>
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -2-((3R, 6R) -6-((3S, 8S, 9R, 11R, 13R,) 14S, 17R) -3,11-dihydroxy-4,4,9,13,14-pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17 -Tetradecahydro-1H-cyclopentane [a] phenanthrene-17-yl) -2-hydroxy-2-methylheptane-3-yloxy) -4,5-dihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran- 3-Iloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol


<Compound Bb>
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl-) 6-((3S, 9R, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran- 2-Iloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) heptane -3-Iloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro -2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol

<Compound Cc>
(2S, 3R, 4S, 5S, 6R) -2-((2R, 3S, 4R, 5R, 6R) -6-((3S, 9R, 13R, 14S, 17R) -17-((2R, 5R)) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxy) Methyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran- 2-Iloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -4,4,9,13,14-pentamethyl-2,3,4,7 , 8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-3-yloxy) -4,5-dihydroxy-2- (hydroxymethyl) Tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol

<Compound Dd>
(2S, 3R, 4S, 5S, 6R) -2-((2R, 3R, 4S, 5S, 6R) -2-((3S, 8R, 9R, 13R, 14S, 17R)) -17-((2R, 6R) 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H- Pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -4,4,9,13,14-pentamethyl-2,3,4 , 7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-3-yloxy) -4,5-dihydroxy-6- (hydroxy) Methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol

<Compound Ee>
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl- 6-((3S, 8R, 9R, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5- Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradeca Hydro-1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxy) Methyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol

<Compound Ff>
(2S, 3R, 4S, 5S, 6R) -2-((2R, 3R, 4S, 5S, 6R) -2-((3S, 8S, 9R, 11R, 13R, 14S, 17R)) -17-(( 2R, 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy- 6- (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro- 2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -11-hydroxy-4,4,9,13,14-pentamethyl -2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro-1H-cyclopenta [a] phenanthrene-3-yloxy) -4,5- Dihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol


<Compound Gg>
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl- 6-((3S, 9R, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy) -6- (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro- 1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3, 4,5-triol

<Compound Hh>
(6R) -2-Hydroxy-6-((3S, 9R, 10R, 11R, 13R, 14S, 17R) -11-Hydroxy-4,4,9,13,14-Pentamethyl-3-((2R, 3R) , 4S, 5S, 6R) -3,4,5-trihydroxy-6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-) 2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra Decahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-methylheptane-3-one

<Compound Jj>
(9R, 10R, 11R, 13R, 14S, 17R) -17-((2R, 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 5R) 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R)) -3,4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2- Il) -11-Hydroxy-4,4,9,13,14-Pentamethyl-4,7,8,9,10,11,12,13,14,15,16,17-Dodecahydro-1H-cyclopenta [a] ] Phenantren-3 (2H) -on

<Compound Kk>
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-6-(((3R, 6R) -2-hydroxy-6-(( 3S, 9R, 10S, 13R, 14S, 17R) -3-Hydroxy-4,4,9,13,14-Pentamethyl-2,3,4,7,8,9,10,11,12,13,14 , 15, 16, 17-Tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-methylheptane-3-yloxy) -6-(((2R, 3R, 4S, 5S, 6R)- 3,4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran- 3,4,5-triol

<Compound Ll>
(3S, 9R, 10R, 13R, 14S, 17R) -17-((2R, 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 5R) 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R)) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2- Il) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran -2-Iloxy) -3,4,7,8,9,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta [a] phenanthrene-11 (2H) -on

<Compound Mm>
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl-) 6-((3S, 9R, 10S, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5- Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradeca Hydro-1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxy) Methyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol.

When the compound of formula (I) contains 2 or more units of sugar constituents (di- or oligosaccharides), the sugar units are glycosidic bonded to each other. Glycosidic bonds are covalent bonds that bind a molecule of carbohydrate (sugar) to a carbohydrate or a different group. Glycosidic bonds occur between the hemiacetal group of the sugar (or a molecule derived from the sugar) and the hydroxyl group of an organic compound such as alcohol. When the group bound to the carbohydrate residue is not another sugar, it is known as an aglycone. For other sugars, the residual unit is also referred to as the reducing end or end of the structure. This is the academic name when the reducing end of the di- or polysaccharide is the last anomeric carbon of the structure, with the ends located on opposite sides.

Glycosidic bonds by the triterpene glycoside compounds of the present invention are shown in Table B.

Furthermore, the present invention relates to extracts containing one or more compounds of formula (I), which are available by liquid and / or alcohol extraction from plants of Momordica grosvenorii (also known as Siraitia grosvenori).

The extract by the method described above comprises at least one formula (I) selected from the following groups.
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -2-((3R, 6R) -6-((3S, 8S, 9R, 11R, 13R) , 14S, 17R) -3,11-dihydroxy-4,4,9,13,14-pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16, 17-Tetradecahydro-1H-cyclopentane [a] phenanthrene-17-yl) -2-hydroxy-2-methylheptane-3-yloxy) -4,5-dihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran -3-Iloxy) -6- (Hydroxymethyl) Tetrahydro-2H-Pyran-3,4,5-Triol (Compound Aa)
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl) -6-((3S, 9R, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5-tri Hydroxy-6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran -2-Iloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) Heptane-3-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) Tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) Tetrahydro-2H-pyran-3,4,5-triol (Compound Bb)
-(2S, 3R, 4S, 5S, 6R) -2-((2R, 3S, 4R, 5R, 6R) -6-((3S, 9R, 13R, 14S, 17R) -17-((2R, 5R) )-5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6-( Hydroxymethyl) Tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran) -2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptane-2-yl) -4,4,9,13,14-pentamethyl-2,3,4 7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-3-yloxy) -4,5-dihydroxy-2- (hydroxymethyl) ) Tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol (Compound Cc)
(2S, 3R, 4S, 5S, 6R) -2-((2R, 3R, 4S, 5S, 6R) -2-((3S, 8R, 9R, 13R, 14S, 17R)) -17-((2R) , 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6) -(Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H) -Pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -4,4,9,13,14-pentamethyl-2,3 4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-3-yloxy) -4,5-dihydroxy-6- ( Hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol (compound Dd)
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl) -6-((3S, 8R, 9R, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5 -Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra Decahydro-1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6-((2R, 3R, 4S, 5S, 6R)) Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol (Compound Ee)
(2S, 3R, 4S, 5S, 6R) -2-((2R, 3R, 4S, 5S, 6R) -2-((3S, 8S, 9R, 11R, 13R, 14S, 17R) -17-( (2R, 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy) -6- (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro) -2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -11-hydroxy-4,4,9,13,14- Pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-3-yloxy) -4,5 -Dihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol (compound Ff)
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl) -6-((3S, 9R, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5-tri Hydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro -1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3 , 4,5-Triol (Compound Gg)
(6R) -2-Hydroxy-6-((3S, 9R, 10R, 11R, 13R, 14S, 17R) -11-Hydroxy-4,4,9,13,14-Pentamethyl-3-((2R,) 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro) -2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17- Tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-methylheptane-3-one (Compound Hh)
(9R, 10R, 11R, 13R, 14S, 17R) -17-((2R, 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S) , 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) ) -3,4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2 -Il) -11-Hydroxy-4,4,9,13,14-Pentamethyl-4,7,8,9,10,11,12,13,14,15,16,17-Dodecahydro-1H-cyclopenta [ a] Phenantren-3 (2H) -on (Compound Jj)
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-6-( (3S, 9R, 10S, 13R, 14S, 17R) -3-Hydroxy-4,4,9,13,14-Pentamethyl-2,3,4,7,8,9,10,11,12,13, 14,15,16,17-Tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-methylheptane-3-yloxy) -6-(((2R, 3R, 4S, 5S, 6R)) -3,4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran -3,4,5-Triol (Compound Kk)
(3S, 9R, 10R, 13R, 14S, 17R) -17-((2R, 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S) , 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) ) -3,4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2 -Il) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H- Pyran-2-yloxy) -3,4,7,8,9,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta [a] phenanthrene-11 (2H) -one (Compound Ll) )
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl) -6-((3S, 9R, 10S, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5 -Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra Decahydro-1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6-((2R, 3R, 4S, 5S, 6R)) Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol (Compound Mm)

The present invention relates to preparations containing 1, 2 or 3 units or more of sweetener compounds of formula (I). Such preparations further include raw materials such as aromatic compounds and / or seasoning compounds and / or sweeteners and / or sweet substances.

Preferred aromatic compounds, seasoning compounds, sweeteners and sweeteners are described in detail below.

The preparations of the present invention have at least one unit of the sweetener compound of formula (I) and are desirable from a variety of oral and food compositions, pharmaceutical compositions such as beverages, foods, dentifrices, lipsticks and similar products. Used to release sweetness and / or flavors, these products may be digestible or indigestible and may be used or separately with other flavors or sweeteners. Furthermore, the present invention relates to various oral and food compositions having at least one unit of the sweetener compound of formula (I) used as a sweetener and / or seasoning.

The sweetener of the present invention is widely applied to general edible substances, and is mainly applied to food compositions such as candies, confectioneries and processed foods, and beverages such as beer and soft drinks. It is also suitable for use in sweetening other edible substances such as chemicals, dentifrices, adhesives for stamps and envelopes, animal feeds, foods and the like. These examples are used only for explanation and do not limit the embodiment of the sweetener used in the present invention to a specific type of edible substance. As a general rule, the sweeteners of the present invention may be applied where sweetness is required. The sweeteners of the present invention may be used alone or in combination with other sweeteners, nutrients or non-nutrients. If desired, a binder or diluent may be added to the sweetener. This is generally not necessary because sweeteners are solids with good handling properties. This allows the sweetener to be mixed with the edible substance using conventional simple techniques. The sweetener may be mixed with the edible substance in the solid or liquid state if desired.

The present invention further relates to a method of using a sweetener compound or preparation of formula (I) to sweeten a composition or preparation, in which an effective amount sufficient to produce the desired sweetness is administered to the human body. Will be done.

That is, the present invention relates to a method of imparting a sweetening effect to a composition and / or enhancing the sweetening effect, which method is sufficiently effective to produce a sweetener compound of formula (I) at a desired degree of sweetness. It is a method of administering to the human body in an amount.

The effective amount is preferably in the range of 1 to 2,000 ppm of the total amount of the composition and the total content of all the compounds of the formula (I).

The food composition, oral composition, and pharmaceutical composition will be described below.

<Food composition>
The food composition according to the present invention is any preparation or composition suitable for consumption and is used for a nutritional product or a favorite product, is usually a product for ingestion from the oral cavity of a human or animal and is incorporated. After that, it stays in the oral cavity for a predetermined time and is then swallowed (food or feed that can be ingested as it is, see also below) or exhaled from the oral cavity (eg, chewing gum). Such products include any substance or product that is ingested in a treated, partially treated, or untreated state. These products also include substances added during the manufacture, preparation or treatment of orally consumable products for ingestion from the oral cavity of humans or animals.

The food composition according to the present invention is also intended for humans or animals to swallow and then digest in either untreated, treated or prepared state, so that the orally consumable product according to the present invention is: Also includes exteriors, clothing and other encapsulations that are or should be swallowed at the same time as the product. The term "orally consumable product" refers to ready-to-eat foods and feed products, i.e. foods and feed products that are already complete with respect to flavor-critical substances. The terms "ready-to-eat food" and "ready-to-eat feed" also include beverages and solid or semi-solid ready-to-eat foods or feeds. Examples include frozen products that need to be thawed or heated before eating. Products such as yogurt, ice cream, or chewing gum or hard caramel are also included in ready-to-eat foods or feeds.

Preferred food compositions according to the invention also include "semi-finished products". In the present specification, the term "semi-finished product" is understood to mean a product (particularly food or feed product) that is not suitable for use as an orally consumable product that can be ingested as it is due to its high content of flavors and seasonings. It should be. This semi-finished product can only be mixed with at least one additional ingredient (eg, reducing the concentration of the flavoring or seasoning corresponding to the above) or by performing a further processing step (eg, heating or freezing). Can be converted into ready-to-eat, orally consumable products (especially food or feed products). Examples of such semi-finished products include the following.

The food composition according to the invention preferably comprises one or more preparations for nutritional intake or preference. Specifically, these include: (low calorie) baked products (eg bread, dried biscuits, cakes and other baked products), confectionery (eg chocolate, chocolate bars, other bar-shaped products, etc. Fruit gum, dragee, hard and soft caramel, chewing gum), non-alcoholic beverages (eg cocoa, coffee, green tea, tea, tea beverages with concentrates of tea extracts (of green tea and tea), roybo tea, and other herbal teas , Fruit-containing soft drinks, isotonic beverages, soft beverages, nectar, fruit and vegetable juices, fruit or vegetable beverages), instant beverages (eg instant cocoa beverages, instant tea beverages, instant coffee beverages), meat products (eg ham) , Fresh sausage or raw sausage products, spice-added products, fresh marine products, or salt-added meat products), eggs or egg products (dried eggs, egg whites, egg yolks), grain products (eg breakfast cereals, mousse rivers, cooked and raw) Ingestible rice products), dairy products (eg whole-fat, low-fat or non-fat milk beverages, rice pudding, yogurt, kefia, cream cheese, soft cheese, hard cheese, dried milk powder, milk syrup, butter , Butter milk, all or partly hydrolyzed dairy protein-containing products), soybean protein or other soybean distillates (eg soymilk or soymilk products, beverages containing separated or enzyme-treated soybean protein, soybean flour-containing beverages , Tofu, Tempe and other soy lecithin-containing products, or products manufactured from them that are a mixture of fruit products and seasoning additives), fruit products (eg jams, sherbets, fruit sauces, fruit pastes), vegetable products (Eg ketchup, sauces, dried vegetables, frozen vegetables, cooked vegetables, boiled vegetables), snacks (eg baked or fried potato chips or potato dough products, corn-based extruded or peanut-based extruded), fats and oils Base products or emulsions thereof (eg mayonnaise, lemlad sauces, dressings, all-fat or low-fat products in any case), other retort foods and soups (eg, dried soups, instant soups, cooked soups), Spices, spice mixtures, especially seasonings, sweeteners, tablets or sachets used in the snack field, whitening drinks, etc. Or other foods. Products within the scope of the present invention can also be used in the form of semi-finished products for the production of further nutritional or favorite products. Products within the scope of the invention are in the form of capsules, tablets (uncoated tablets or tablets coated with, for example, enteric coatings), dragees, granules, pellets, solid mixtures, or emulsions, powders, solutions, or It can be in the form of a dispersion in the liquid phase, such as a paste, or in the form of other swallowable or chewable products, and dietary supplements.

This semi-finished product is usually used in the production of ready-to-use or ready-to-use nutritional or luxury products.

Additional ingredients of ready-to-eat nutritional products or semi-finished products or luxury products or semi-finished products are exemplified below, for example, in the base substances, auxiliary substances, and additives of conventional foods or luxury products such as: May be: water, or unprocessed or processed vegetables, animal-derived foods or raw substances (eg, raw, roasted, dried, fermented, smoked and / or boiled meat, Bone, cartilage, fish, vegetables, herbs, nuts, vegetable juices, vegetable pastes, or mixtures thereof), digestible or non-digestible carbohydrates (eg sucrose, maltose, fructose, glucose, dextrin, amylose, Amylopectin, inulin, xylan, cellulose, tagatose), sugar alcohols (eg sorbitol, erythritol), natural or hardened fats (eg tallow, lard, palm fat, cocoa oil, hardened vegetable fat), oils (eg sunflower oil, Pepper oil, corn germ oil, olive oil, fish oil, soybean oil, sesame oil), fatty acids or salts thereof (eg potassium stearate), proteinogenic or non-proteinogenic amino acid related compounds (eg γ-aminobutyric acid, tagatose) peptides (eg γ-aminobutyric acid, taurine) For example, glutathione), natural or processed proteins (eg gelatin), enzymes (eg peptidases), nucleic acids, nucleotides, flavor modifiers that modify unpleasant flavors, and usually flavor modifiers that modify even more unpleasant flavors, and others. Flavor modifiers (eg, nucleotides such as inositol phosphate, guanosine monophosphate and adenosine monophosphate, other substances such as sodium glutamate or 2-phenoxypropionic acid), emulsifiers (eg lecithin, diacylglycerol, gum arabic), stable Agents (eg caragi-nan, alginate), preservatives (eg benzoic acid and its salts, sorbic acid and its salts), antioxidants (eg tocopherol, ascorbic acid), chelating agents (eg citric acid), organic or Bitter foods as additives (eg quinine, caffeine, limonene, amarogentin, humron, lupron, catechol, tannin), enzymatic browning inhibitors (eg sucrose ester, ascorbic acid) ), Essential oils, vegetable extracts, natural or synthetic colorants or coloring pigments (eg carotinoids, flavonoids, anthocyans, sucrose and derivatives thereof), spices, three Botanical extracts, synthetic fragrances, natural fragrances, nature identity synthetic fragrances, or odorants, and aroma modifiers containing forked nerve active substances or such trigeminal nerve active substances.

The food composition according to the present invention, for example in the form of a preparation or semi-preparation, preferably contains a seasoning component in order to make its taste and aroma better than the finish. The preparation may contain a solid carrier and a seasoning component as components. Suitable seasoning compounds include, for example: synthetic, natural, or nature-identical seasonings, aromatics and seasonings, reactive seasonings, smoke seasonings or other seasonings (eg, protein (partial) hydrolyzed. Protein (partial) hydrolyzate, preferably arginine-rich), barbecue seasonings, plant extracts, spices, spice products, vegetables and / or vegetable products, and suitable auxiliary substances and carriers. Also here, seasoning compounds or components thereof that produce the following flavors are particularly preferred: roasted meat flavors (chicken, fish, seafood, beef, pork, lamb, mutton, goat, etc.), vegetables. Flavors (especially tomatoes, onions, garlic, celery, leek, mushrooms, eggplant, seaweed, etc.), spice flavors (especially black pepper, white pepper, cardamon, nutmeg, piment, mustard, and mustard product flavors), fried Flavors, yeast product flavors, boiled product flavors, fatty flavors, salty flavors and / or pungent flavors that can enhance the spice flavor. A seasoning compound generally contains two or more of the above-mentioned components.

The food composition of the present invention is preferably selected from the group comprising:
Confectionery, preferably low-calorie or zero-calorie confectionery, selected from the group including: Museliever products, fruit gums, dragees, hard caramel and chewing gum,
Non-alcoholic beverages, preferably selected from the group including: green tea, black tea, green tea or black tea beverages with tea extracts (of green tea and black tea), roybos tea, other herbal teas, fruit-containing Low sugar or sugar-free soft drinks, isotonic drinks, nectar, fruit and vegetable juices, fruit and vegetable juice products,
-Instant beverages, preferably selected from the group including: Instant (green tea, black tea, roybosty, herbal tea) tea beverages
-Cereal products, preferably selected from the group including: low sugar and sugar-free breakfast cereals and mood rivers,
Dairy products, preferably selected from the group including: low-fat and non-fat milk drinks, yogurt, kefir, milk syrup, buttermilk and ice cream,
Produced from soy protein or other soy distillates, preferably selected from the group including: soy milk, soy milk products, beverages containing separated or enzymatically treated soy protein, soy flour containing Beverages, soy lecithin-containing products, products manufactured from soy lecithin-containing products, and mixtures with fruit products and additional seasonings,
・ Sweetener products, tablets and sachets,
・ Sugar-free dragee,
-Ice cream with or without milk ingredients, preferably sugar-free.

<A. Aromatic compounds or seasoning compounds>
Aromatic compounds and seasonings known to those skilled in the art can be added to the seasoning compounds of the present invention. Such seasonings may be synthetic seasonings and / or oils derived from plant leaves, flowers, fruits and the like, or combinations thereof. Typical examples of such seasonings include: eucalyptus, lemon, orange, banana, grape, lime, apricot and grape, lime, apricot, and artificial, natural such as grapefruit oil and fruit essence. , Or synthetic fruit seasonings, including apples, strawberries, cherries, oranges, pineapples; coffee, cocoa, cola, Nanjing beans, almonds, etc. Bean and nut-derived seasonings; A seasoning derived from the roots of.

This seasoning is preferably selected from the group including: anisole, basil oil, bergamot oil, bitter almond oil, camphor oil, citronella oil, lemon oil and other essential oils, extracts, tinctures, and balsam; Eucalyptus citriodora oil. , Eucalyptus oil, fennel oil, grapefruit oil, chamomile oil, spearmint oil, caraway oil, lime oil, mandarin oil, nutmeg oil (especially nutmeg flower oil = mace oil), milla oil, butterfly oil, clove flower oil , Orange oil, oregano oil, parsley (seed) oil, peppermint oil, rosmarin (rosemary) oil, sage oil (clary sage oil, dalmesian oil, or Spanish sage oil), staranis oil, thyme oil, vanilla extraction Things, juniper oils (especially juniper berry oils), winter green oils, cinnamon leaf oils; cinnamon skin oils, and their distillates, or components separated from them.

It is particularly advantageous that the seasoning component according to the present invention contains at least one, preferably 2, 3, 4, 5, 6, 7, 8 or more seasonings selected from the group comprising: Menthone (preferably l-menthol and / or menthol racemic), anetol, anisole, anisaldehyde, anisyl alcohol, neomenthol racem, eucalypto (1,8-cineole), menthone (preferably L-menthone) , Isomentone (preferably D-isomentone), isopregol, menthyl acetate (preferably L-menthyl acetate), menthyl propionate, carboxylic (preferably (-)-carboxylic, or may be a component of spearmint oil), methyl salicylate. (Or it may be a component of winter green oil), Eugenol acetate, Isooygenol dimethyl ether, Beta homocyclocitral, Eugenol, Isobutylaldehyde, 3-Octanol, Dimethyl sulfide, Hexanol, Hexanal, trans-2-hexenal, cis-3- Hexenol, 4-terpineol, piperitone, linalol, 8-oxymethylacetate, isoamyl alcohol, isobarrelaldehyde, α-pinene, β-pinene, limonene (preferably as a component of D-limonene or essential oil), piperitone, trans-sabinene hydrate, menthone, cariophyllene, germaneculene D, cinnamaldehyde are lactone, timol, γ-octalactone, γ-nonalactone, γ-decalactone, (1,3E, 5Z) -undecatorien, 2- Butanone, ethyl formate, octyl 3-acetate, isoamylisovalerate, cis- and trans-carbyl acetate, p-simole, damasenone, damascon, cis-rose oxide, trans-rose oxide, fencol, acetaldehyde diethylacetal, 1 -Ethoxyethyl acetate, cis-4-heptenal, cis-jasmon, methyldihydrojasmonate, 2'-hydroxypropiophenone, menthone methyl ether, myltenyl acetate, 2-phenylethyl alcohol, 2-phenylethyl isobutyrate , 2-Phenylethylisovalerate, geraniol, nerol, and viridiflorol.

Particularly preferred aroma or seasoning compounds include: menthol, cineole, eugenol, timol, cinnamaldehyde, peppermint oil, spearmint oil, eucalyptus oil, thyme oil, siliceous oil, butterfly oil, peppermint leaf oil, fennel oil, sage. Oils, anis oils, star anis oils, chamomile oils and caraway oils, and mixtures thereof.

<B. Sweeteners and sweeteners>
In the present invention, the term "sweetener" refers to a substance having a relative sweetness of at least 25 degrees based on the sweetness of sucrose (sweetness of 1 degree). The sweetener used in the orally consumable product (particularly food, feed or drug) according to the present invention (a) is preferably non-cariogenic and / or has an energy content of 5 kcal per gram of the orally consumable product. Have.

The sweetener used in the orally consumable product (particularly food, feed or drug) based on the present invention is selected from the following groups (a1) and (a2).

(I) Naturally-derived sweeteners, preferably selected from the group comprising:
Miraculin, monellin, mabinlin, taumatin, curculin, brazzein, pentamidine, D-phenylalanine, D-tryptophan, and naturally occurring extracts or distillates containing these amino acids and / or proteins physiologically. / Or protein salts, especially those acceptable as sodium chloride, potassium chloride, calcium chloride, or ammonium chloride;
・ Neohesperidin dihydrochalcone, naringingihydrochalcone, stebioside, steviolbioside, rebaudioside, especially rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaugioside F, rebaudioside G , Suavioside B, Suavioside G, Suavioside H, Suavioside I, Suavioside J, Bayunoside 1, Bayunoside 2, Fromisoside 1, Fromisoside 2, Fromisoside 3, and Fromisoside 4, Abulsoside A, Abulososide B, Abulososide C, Abulososide D A. trans-annetol, trans-cinnamaldehyde, brioside, brionoside, brionozzurcoside, carnosifloside, scandenoside, gipenoside, trilobatin, phlorizin, dihydroflavanol, hematoxylin, cyanine, chlorogenic acid, alvidia saponin, telosmoside, mogroside, mogroside , Mogroside V, Hernandultin, Monatin, Phyllodulcin, Glycyrrhetinic acid and its derivatives, especially glycosides such as glycyrrhizin, and physiologically acceptable salts of these compounds, especially sodium chloride, potassium chloride, calcium chloride, or chloride. Acceptable as ammonium;
An extract or a concentrated distillate of the extract selected from the group including: licorice extract (miracle fruit tree), Stevia subspecies (especially Stevia rebaudiana) extract), raspberry Extracts (Momordica or Siratia grosvenorii (Luo Han Guo)), licorice (Glycyrrhiza) subspecies (especially licorice (Glycyrrhiza glabra) extract, raspberry subspecies extract (especially Rubus suavissimus)), citrus extracts and Mexican sweet herb (Lippia dulcis) extract.
(Ii) Synthetic sweeteners, preferably selected from the group comprising: Magap, sodium saccharinate or other physiologically acceptable salts of saccharinate, acesulfame K or other physiological of acesulfame. Acceptable salts for, neohesperidin dihydrocalcone, naringingihydrocalcone, saccharin, saccharin-sodium salt, aspartame, superaspartame, neotame, alitame, advantage, perilartin, sucralose, ragduname, carreram, sucralose, and scrooctate.

Suitable sweeteners, including natural products of these substances, are, for example:
-Sweet carbohydrates or sugars (eg, sucrose / saccharose, trehalose, lactose, maltose, meriditose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, L-lamnose, D-sorbose, D- Mannose, D-tagatose, D-arabinose, L-arabinose, D-ribose, D-glyceraldehyde, maltodextrin), or plant preparations containing these carbohydrates (eg, beta vulgaris). ) Subspecies, sugar fraction, sugar syrup, sugar honey), sugar cane (Saccharum officinarum subspecies, sugar syrup, sugar syrup), sugar maple (Acer subspecies), agarbe (eg, agarbe) Derived from concentrated juice),
Hydrolyzate of starch or sugar produced from synthetic / enzyme (eg, invert sugar syrup, highly concentrated fructose syrup produced from cornstarch)
-Fruit concentrates (eg apple or pear derived, apple syrup, pear syrup,
-Sugar alcohols (eg, erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, zulcitol, lactitol)
-Proteins (eg miraculin, monellin, taumatin, curculin, brazzein)
Sweeteners (eg, magap, sodium cyclamate, acesulfame K, neohesperidin dihydrocalcon, saccharin-sodium salt, aspartame®, superaspartame, neotame, alitame, sucralose, rugduname, carreram, scrononate, Sucralose, monatin),
-Some sweet amino acids (glycine, D-leucine, D-threonine, D-asparagine, D-phenylalanine, D-tryptophan, L-proline)
Other sweet low molecular weight substances (eg, rebaudioside, stevioside, mogroside, hernan dulcin, fildulcin, dihydrochalcone, glycosides, glycyrrhizin, ammonium glycyrrhetinate or other glycyrrhizic acid derivatives)
Extracts of sweet plants, especially Momordica grosvenori (Luo Han Guo), Hydrangea macrophylla, Stevia ssp. (Especially Stevia rebaudiana), Rubus suavissimus, Ezodenda (Polypodium vulgare) , Touazuki (Abrus precatorius), Pterocarya paliurus, Baccharis gaudichaudiana, Albizia myriophylla, Bryonia dioica, Phlomis betonicoides, Hemsleya carnosiflora, Mexican sweet herb (Lippia dulcis), Amachazuru (Gynost) A sweet substance isolated from these plants.

<C. Thickener>
Advantageous thickeners for use in suitable orally consumable products (particularly foods, feeds or drugs) according to the present invention are selected from the group including: crosslinked polysaccharide cellulose and derivatives thereof, xanthan gum, agar, alginic acid. Polysaccharides such as salts or tyroses and derivatives thereof, cellulose derivatives such as carboxymethyl cellulose or hydroxycarboxymethyl cellulose, fatty alcohols, monoglycerides and fatty acids, polyvinyl alcohols, and polyvinylpyrrolidone.

Further, the orally consumable products (particularly food products or feed products) according to the present invention are preferably milk thickened by lactic acid bacteria and / or cream thickened by lactic acid bacteria, preferably yogurt, kefir, quackti. It is selected from the group consisting of lactic acid.

The food composition according to the present invention comprising milk thickened by Lactobacillus lactic acid or cream thickened by Lactobacillus lactic acid bacteria is advantageously an orally consumable product containing probiotics, the probiotics preferably comprising: Selected from the group: Bifidobacterium Animalis Subspecies Lactis BB-12, Bifidobacterium Animalis Subspecies Lactis DN-173010, Bifidobacterium Animalis Subspecies Lactis HN019, Lactobacillus Acidophilus LA5, Lactobacillus acidophilus NCFM, Lactobacillus Johnsoni La1, Lactobacillus casei immunitas / defense, Lactobacillus casei Shirota (DSM20312), Lactobacillus casei CRL431, Lactobacillus reuteri (ATCC 55730) and Lactobacillus reuteri (ATCC 55730) ..

<D. Chewing gum additive>
Also, the orally consumable products (particularly food or feed products) according to the present invention are preferably chewing gum and include a chewing gum base. This chewing gum base is preferably selected from the group including: chewing gum base or bubble gum base. Bubble gum base is a softer base so that you can make balloons with gum. Suitable chewing gum bases according to the present invention include, in addition to conventionally used natural resins or natural tickle resins, the following: polyvinyl acetate (PVA), polyethylene, (low or medium molecular weight), polyisobutene ( PIB), polybutadiene, isobutene-isoprene copolymer (butyl rubber), polyvinyl ethyl ether (PVE), elastomers such as polyvinyl butyl ether, vinyl ester copolymers, vinyl ether, styrene-butadiene copolymer (styrene-butadiene rubber, SBR), or vinyl elastomer , For example, a mixture of vinyl acetate / vinyl laurate, vinyl acetate / vinyl stearate or ethylene / vinyl acetate, and the above-mentioned elastomers (European Patent Application Publication No. 0242325, US Patent No. 4,518,615, US Patent No. 5,093,136, US Pat. No. 5,266,336, US Pat. No. 5,601,858 or US Pat. No. 6,986,709). In addition, the chewing gum base preferably used in the present invention contains, for example, the following additional components: (mineral) fillers, plasticizers, emulsifiers, antioxidants, waxes, hardened vegetable fats or animal fats and other fats or Fat oil, mono, di- or triglyceride. Suitable (mineral) fillers are calcium carbonate, titanium dioxide, silicon dioxide, talcum, aluminum oxide, dicalcium phosphate, tricalcium phosphate, and magnesium hydroxide and mixtures thereof. Suitable plasticizers or anti-adhesive agents (de-adhesives) are, for example, lanolin, stearic acid, sodium stearate, ethyl acetate, diacetin (glycerin diacetate), triacetin (glycerin triacetate), triethylcitrate. Suitable waxes are, for example, paraffin wax, candelilla wax, carnauba wax, microcrystalline wax and polyethylene wax. Suitable emulsifiers are, for example, phosphatides such as lecithin, mono- and di-glycerides of fatty acids such as glycerin monostearate.

The chewing gum according to the present invention (particularly as described above) preferably contains the following components: different types of sugars, sucrose substitutes, other sweeteners, sugar alcohols (particularly sorbitol, xylitol, mannitol), refreshing. Ingredients that have an effect, flavor modifiers to prevent unpleasant flavors, as well as inositol phosphate, nucleotides (eg guanosine, monophosphate, adenosine monophosphate or other substances (eg sodium glutamate or 2-phenoxypropionic acid) )) Flavor modifiers, wetting agents, thickeners, emulsifiers, stabilizers, aroma modifiers and seasonings (eg eucalyptus xylitol, sakurambo, strawberries, grapefruit, vanilla, bananas, citrus fruits, peaches, etc. Flavored seasonings such as black sorbitol, tropical fleet, ginger, coffee, cinnamon, and in combination with mint flavored seasonings, spare mint flavored seasonings, peppermint flavored seasonings, or when used alone). In particular, seasonings that also have a refreshing effect, a heating effect and / or mouth moisturizing performance are particularly beneficial.

<E. Vitamins>
As another embodiment of the present invention, the food additive may contain a vitamin (constituent e1) as a group of additives. Vitamins have a wide range of functions in biochemical action. Some vitamins have similar functions to hormones, maintain mineral metabolism (eg, vitamin D), or promote cell and tissue growth and cell differentiation (eg, vitamin A). Other vitamins are used as antioxidants (eg vitamin E and vitamin C under certain conditions). The maximum number of vitamins is a precursor of enzyme cofactors (eg, B vitamins) and functions as a coenzyme for catalytic enzymes in certain metabolic processes. Along with this, vitamins sometimes bind strongly to enzymes, for example as part of a formulation group. An example of the compounding group is biotin, which is a part of an enzyme that causes fatty acid synthesis. On the other hand, for example, as a group that is easily separated, vitamins bind with a weak force and function as a cocatalyst, thereby transporting by utilizing intermolecular compounds or electrons. Thus, for example, folic acid transports a group of methyl, formyl, and methylene groups into the cell. Although the function of vitamins in enzyme-substrate reactions is well known, other properties of vitamins are also important factors for the body.
Vitamins suitable in the present invention are selected from the following groups.
・ Vitamin A (retinol, retinal, β-carotene),
・ Vitamin B ₁ (thiamine),
・ Vitamin B ₂ (riboflavin),
・ Vitamin B ₃ (niacin, nicotinamide),
・ Vitamin B ₅ (pantothenic acid),
・ Vitamin B ₆ (pyridoxine, pyridoxamine, pyridoxal),
・ Vitamin B ₇ (biotin),
・ Vitamin B ₉ (folic acid, folinic acid),
-Vitamin B ₁₂ (cyanocobalamin, hydroxocobalamin, methylcobalamin),
・ Vitamin C (ascorbic acid),
・ Vitamin D (cholecalciferol),
-Vitamin E (tocopherol, tocotrienol) and-Vitamin K (phylloquinone, menaquinone).

Particularly preferred vitamins are the tocopherols, in addition to ascorbic acid.
The above-mentioned vitamins are contained in the food composition in a proportion of about 0.1 to 5% by weight, preferably in a proportion of about 0.5 to 1% by weight.

<Oral care compound>
Typical examples of oral care compounds that cannot be consumed as food include products intended for cleaning and protecting teeth and refreshing the oral cavity.

The oral care compounds of the present invention are generally abrasives (grinding or abrasives), such as surface active substances such as silicic acid, calcium carbonate, calcium phosphate, aluminum oxide and / or hydroxylapatite, such as sodium lauryl sulfate, lauryl sarcosin. Wetting agents such as sodium and / or cocamidopropyl betaine, such as glycerin and / or sorbite, thickeners such as carboxymethyl cellulose, polyethylene glycol, caragi-nan and / or Laponite®, unpleasant taste. Taste-correcting agents for, additional generally non-unpleasant taste-correcting agents, taste modifiers (eg, inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances, such as sodium glutamate). Or 2-phenoxypropionic acid) and other coolants, such as menthol, menthol derivatives (eg L-menthol, L-mentyl lactate, L-mentyl alkyl carbonate, menton ketal, menthan carboxylic acid amide), 2, 2, 2 -Stabilizers and active substances such as trialkylacetamide (eg 2,2-diisopropylpropionic acid methylamide), isylin derivatives, etc., such as sodium fluoride, sodium monofluorophosphate, tin fluoride, quaternary ammonium fluoride, citric acid Zinc, zinc sulfate, stannous pyrophosphate, tin chloride, mixtures of various pyrophosphates, triclosan, cetylpyridinium chloride, aluminum lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, fragrances and / Or it contains sodium carbonate or an odor correctant.

The formulations or products of the present invention in the form of chewing gum or dental care chewing gum are described, for example, in European Patent No. 0242 325, US Pat. No. 4,518,615, No. 5,093,136. Elastomers such as polyvinyl acetate (PVA), as described in the book, 5,266,336, 5,601,858, or 6,986,709. Polyethylene, (low molecular weight or intermediate molecular weight), polyisobutene (PIB), polybutadiene, isobutene-isoprene copolymer (butyl rubber), polyvinyl ethyl ether (PVE), polyvinylbutyl ether, vinyl ester and divinyl ether copolymer, styrene / butadiene copolymer (styrene / butadiene / Includes butadiene rubber, SBR) or vinyl elastomers, such as those based on vinyl acetate / vinyl laurate, vinyl acetate / vinyl stearate or ethylene / vinyl acetate, or chewing gum bases containing a mixture of the elastomers described. In addition, chewing gum bases can further include ingredients such as (mineral) fillers, plasticizers, emulsifiers, antioxidants, waxes, fats or fatty oils, such as hardened (hydrogenated) vegetable fats or Contains animal fats, or mono, di- or triglycerides. Suitable (mineral) fillers are, for example, calcium carbonate, titanium dioxide, silicon dioxide, talc, aluminum oxide, dicalcium phosphate, tricalcium phosphate, magnesium hydroxide or mixtures thereof. Suitable plasticizers or substances that prevent sticking (stripping agents) are, for example, lanolin, stearic acid, sodium stearate, ethyl acetate, diacetin (glycerol diacetate), triacetin (glycerol triacetate) or triethylcitrate. Suitable waxes are, for example, paraffin wax, candelilla wax, carnauba wax, microcrystalline wax or polyethylene wax. Suitable emulsifiers are, for example, phospholipids such as lecithin, or mono- or di-glycerides of fatty acids such as glycerol monostearate.

The formulations of the present invention, especially those in the form of oral care products, preferably further include one or more aromatics and / or flavoring substances such as essential oils or extracts, tinctures and balsams such as anisole and basil. Oil, bergamot oil, bitter peach oil, cypress oil, citronella oil, lemon oil; Eucalyptus citriodora oil, eucalyptus oil, fennel oil, grapefruit oil, ginger oil, chamomile oil, sparemint oil, caraway oil, lime Oil, mandarin oil, nikuzuku oil (especially nutmeg blossom oil = maces oil, maces oil), millula oil, clove oil, orange oil, oregano oil, parsley (seed) oil, peppermint oil, rosemary oil, sage oil (especially Clarisage, Dalmesian or Spanish Sage Oil), Staranis Oil, Thyme Oil, Vanilla Extract, Juniper Oil (especially Juniper Berry), Winter Green Oil, Cinnamon Leaf Oil; Cinnamon Burke Oil, Fractions of These, or Separated From Contains ingredients.

It is particularly advantageous when the formulation of the present invention contains at least one limonene selected from the following group, preferably 2, 3, 4, 5, 6, 7, 8, 9, 10 or more limonene. Yes: menthol (preferably I-menthol and / or racemic menthol), anetol, anisole, anisaldehyde, anisyl alcohol, (lame) neomenthol, eucalypto (1,8-cineole), menton ( As a component of preferably L-mentone), isomentone (preferably D-isomenton), isopregol, menthyl acetate (preferably L-mentyl acetate), menthyl propionate, carboxylic acid (preferably (-)-carboxylic acid, and optionally sparemint oil). ), Methyl salicylate (as a component of winter green oil if necessary), Eugenol acetate, Isoeugenol methyl ether, Beta-homocyclocitral, Eugenol, Isobutylaldehyde, 3-Octanol, Dimethylsulfide, Hexanol, Hexanal, Trans-2-hexenal, Sis-3-hexenol, 4-terpineol, piperitone, linarool, 8-osimenyl acetate, isoamyl alcohol, isobarrelaldehyde, alpha-pinene, beta-pinene, limonene (preferably D-limonene, optionally as a component of essential oils), Piperiton, Trans-Sabinene Hydrate, Mentofuran, Cariophyllene, Germaclen D, Sinnamaldehyde, Mintlactone, Timor, Gamma-Octalactone, Gamma-Nonalactone, Gammadecalactone, (1,3E, 5Z) -Undecatorien, 2-butanone, ethylhomet, 3-octyl acetate, isoamyl isovalerate, cis-carbyl acetate, trans-carbyl acetate, p-simole, damasenone, damascon, cis-rose oxide, trans-rose oxide, fencor , Acetaldehyde diethyl acetic acid, 1-ethoxyethyl acetate, cis-4-heptenal, cis-jasmon, methyldihydrojasmonate, 2'-hydroxypropiophenone, menthylmethyl ether, myltenyl acetate, 2-phenylethyl alcohol, 2 -Phenylethyl isobutyrate, 2-phenylethyl isovalerate, geraniol, nerol and viridiflorol.

<Pharmaceutical composition>
The pharmaceutical composition of the present invention may contain additives such as aromas and flavors similar to those of the food and oral compositions described above. In addition, the pharmaceutical composition comprises an oil or emulsifier and, in particular, a coactive element that enhances the beneficial properties of the pharmaceutically active agent. Therefore, the boundary between the food composition and the pharmaceutical composition is the flow rate, and the components shown in one application method are applied without exception in the other application method without any wording repetition.

A further object of the present invention is the use of a preparation containing at least one sweetener compound of formula (I) or at least one sweetener compound of formula (I), which is a food, oral or pharmaceutical composition. It relates to a compound that gives sweetness when ingested as a substance and / or emphasizes the sweetening effect and is ingested by the human body. Preferably, when one or more units of the compound of formula (I) are used, one or two of the compounds of formula (I) will be added to the total weight of the composition and the total amount of all the compounds of formula (I). On the other hand, it is used in an amount of 1 to 2,000 ppm. More preferably, when one or more units of the compound of the formula (I) are used, one or two of the compounds of the formula (I) is the total weight of the composition and the total amount of all the compounds of the formula (I). On the other hand, it is used in an amount of 10 to 1,000 ppm, and particularly preferably in an amount of 20 to 500 ppm.

In another example, a preparation comprising a sweetener compound of formula (I) or at least one sweetener compound of formula (I) to synergistically emphasize the sweetness of the sweetener contained in the composition. , Compounds or preparations are used. Preferred examples of the compounds of formula (I) are preferably selected from the following groups:
-Compound A
3,11-Dihydroxy-4,4,9,13,14-Pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro- 1H-Cyclopentane [a] phenanthrene-17-yl) -2-hydroxy-2-methylheptane-3-yloxy) -4,5-dihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy)- 6- (Hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol;
-Compound B
4,5-Dihydroxy-2-(2-Hydroxy-2-methyl-6-((4,4,5,13,14-pentamethyl-3-(3,4,5-trihydroxy-6-((3)) , 4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10 , 11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6-((3,4,5-trihydroxy) -6- (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol;
-Compound C
4,5-Dihydroxy-3- (3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-((3,4,5-trihydroxy-6-) (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -4,4,9,13,14 -Pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro-1H-cyclopenta [a] phenanthrene-3-yloxy) -4, 5-Dihydroxy-2- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol;
-Compound D
2- (2- (17- (5- (4,5-dihydroxy-3- (3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6- ( (3,4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2- Il) -4,4,9,13,14-pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [A] Phenantren-3-yloxy) -4,5-dihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5 -Triol;
-Compound E
2- (4,5-Dihydroxy-2- (2-Hydroxy-2-methyl-6- (4,5,9,13,14-Pentamethyl-3- (3,4,5-Trihydroxy-6-) Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a] Phenantren-17-yl) heptane-3-yloxy) -6-((3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H- Piran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-piran-3,4,5-triol;
-Compound F
2-((6-(6-(3- (4,5-dihydroxy-6- (hydroxymethyl) -3- (3,4,5-dihydroxytetrahydro-2H-pyran-2-yloxy) tetrahydro-2H-) Pyran-2-yloxy) -11-Hydroxy-4,4,9,13,14-Pentamethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17 -Tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-hydroxy-2-methylheptane-3-yloxy) -3,4-dihydroxy-5- (3,4,5-trihydroxy- 6- (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) tetrahydro-2H-pyran-2-yl) methoxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol;
-Compound G
2- (4,5-Dihydroxy-2- (2-Hydroxy-2-methyl-6- (4,5,9,13,14-Pentamethyl-3- (3,4,5-Trihydroxy-6-) Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a] Phenantren-17-yl) heptane-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5- Triol;
-Compound H
2-Hydroxy-6- (11-Hydroxy-4,4,9,13,14-Pentamethyl-3- (3,4,5-Trihydroxy-6-((3,4,5-Trihydroxy-6-) (Hydroxymethyl) Tetrahydro-2H-pyran-2-yloxy) Methyl) Tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15 , 16,17-Tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-methylheptane-3-one;
-Compound J
17- (5- (4,5-dihydroxy-3- (3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-((3,4,5) -Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -11-hydroxy -4,4,9,13,14-pentamethyl-4,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta [a] phenanthrene-3 (2H) ) -On;
-Compound K
2- (4,5-Dihydroxy-2- (2-Hydroxy-6- (3-Hydroxy-4,4,9,13,14-Pentamethyl-2,3,4,7,8,9,10,11) , 12,13,14,15,16,17-Tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-methylheptane-3-yloxy) -6-((3,4,5-yl) Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5 Triol;
-Compound L
17- (5- (4,5-dihydroxy-3- (3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-((3,4,5) -Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -4,4 , 9,13,14-Pentamethyl-3- (3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -3,4,7,8,9,10, 12, 13, 14, 15, 16, 17-dodecahydro-1H-cyclopenta [a] phenanthrene-11 (2H) -on;
・ Compound M
2- (4,5-Dihydroxy-2- (2-Hydroxy-2-methyl-6- (4,5,9,13,14-Pentamethyl-3- (3,4,5-Trihydroxy-6-) Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a] Phenantren-17-yl) heptane-3-yloxy) -6-((3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H- Piran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-piran-3,4,5-triol;

Here, the above-mentioned isomers (Aa) to (Mm) are most preferable.

A further aspect of the present invention is an extract comprising one or more compounds of formula (I).

Here, R ₁ , R ₂ , and R ₃ are independent of each other and represent a sugar component selected from the group of hydrogen, hydroxyl, carbonyl, or monosaccharide and / or oligosaccharide.
The extract is available by liquid and / or alcoholic extraction from the plants of Momordica grosvenorii (also known as Siraitia grosvenori).

As used herein, the term "vegetable substance" means a portion of a plant of Momordica grosvenorii (Siraitia grosvenori). Botanical material includes plant parts such as flowers, fruits, buds, roots, seeds and / or leaves, or all plants.

The extract comprises at least one formula (I) selected from compounds A, B, C, D, E, F, G, H, J, K, L, M or mixtures thereof.

Here, the above-mentioned isomers (Aa) to (Mm) are most preferable.

More preferably, the extract contains at least 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 compounds of formula (I). Preferably, the extract comprises all of compounds I to XII of formula (I), particularly comprising the isomers (Aa) to (Mm) described above.

<Extract>
The extracts of the present invention can be prepared, for example, by an extraction method using water, alcohol, or liquid / alcohol for whole or part of the plant or lychee-fruit shell. Suitable extraction processes are known extraction methods, such as cold immersion, re-cold immersion, warm immersion, stirring cold immersion, vortex extraction, ultrasonic extraction, countercurrent extraction, percolation, repercoration, evacuation (decompression). Extraction below), diacholation, and solid / liquid extraction under continuous reflux. Percolation is advantageous for industrial applications. Lychee shells are preferred as starting material and may be mechanically reduced in size prior to extraction. Selective sizing methods known to those of skill in the art (eg, freeze milling) can be used. Preferred solvents for the extraction process are organic solvents, water (preferably hot water at temperatures above 80 ° C., more specifically above 95 ° C.) or mixtures of organic solvents and water, more specifically. It is a low molecular weight alcohol with a slightly high water content. Extraction with methanol, ethanol, isopropanol and hydrous mixtures thereof is particularly preferred. The extraction process is usually carried out at about 20 to about 100 degrees Celsius, preferably about 50 to about 70 degrees Celsius. In one preferred embodiment, the extraction process is carried out in an inert gas atmosphere to prevent oxidation of the extract components. This is especially important when the extraction is performed at a temperature of 40 ° C. or higher. The extraction time will be selected by those skilled in the art depending on the starting material, extraction method, extraction temperature and ratio of solvent to raw material. After the extraction process, the resulting crude extract can optionally be subjected to other conventional steps (eg, purification, concentration and / or decolorization, etc.). If desired, the extracts thus prepared can be subjected to, for example, selective removal of individual unwanted components. The extraction process can be carried out to a selective degree, but is usually depleted. The usual yield (= dry extract based on the amount of raw material used) in the extraction of dried leaves is 1 to 20% by weight, preferably 2 to 15% by weight, more preferably 5 to 10% by weight based on the starting material. It is in the range of%.

The content of the extracts of each compound (A) to (M) varies from mass to mass depending on the raw material used for the fruit of M. grosvenori. A common tripelten glycoside, commonly known as an extract of M. grosvenori, is mogroside V, with relative amounts of the total amount of tripelten glycosides between 50-90%. Compounds (A) to (M) represent 0.01 to 5% of the total amount of tripelten glycosides contained in M. grosvenori.

Furthermore, the present invention administers at least one sweet compound of formula (I) or at least one preparation of formula (I) or at least one extract of formula (I) to a food composition, oral composition. The present invention relates to a method for imparting a sweetening effect and / or an enhanced sweetening effect to a composition such as a substance or a pharmaceutical composition.

Suitable food compositions include, for example, confectioneries such as chocolate, chewing gum, hard caramel, dairy products such as yogurt, buttermilk, cheese, ice cream, non-alcoholic beverages, soft beverages, fruit beverages and other beverages, and baked products. Foods, meat products such as sausages, cereal products such as museuri and cereals, fruit products such as jams, sherbets, and fruit sauces, and "semi-finished products". Applicable forms are exemplary and are not limited to the above. The sweetener compound of formula (I) can be used in all products to impart sweetness.

Furthermore, the present invention relates to a method of using a compound of formula (I) to synergistically emphasize the sweetness of a sweetening substance.

The present invention further relates to a method of sweetening or emphasizing an oral composition, comprising a method of adding one or more compounds of formula (I) to the composition in an amount of about 1 ppm to 2,000 ppm.

In particular, the present invention relates to an edible composition comprising an edible substance and at least one compound of formula (I).

Here, R ₁ , R ₂ and R ₃ are independent and represent sugar components selected from the group of hydrogen, hydroxyl, carbonyl or monosaccharide and / or oligosaccharide to produce the desired sweetness. Sufficient amount is included.

A preferred effective amount is between 1 ppm and 2,000 ppm (based on edible material) of the weight of the composition and the total amount of the compound of formula (I), particularly preferably 10 ppm to 1,000 ppm by weight. Of, more preferably between 20 ppm and 500 ppm by weight.

Preferred edible compositions are the food compositions described herein.

In addition, the compounds of formula (I) are suitable as sweeteners in the composition.

The present invention will be further described by the following examples.
These examples are for explaining the present invention and do not reduce the scope of the present invention.

Further, the present invention relates to a preparation containing 1, 2 or 3 units or more of the sweetener compound of the formula (I), wherein the preparation is optionally an aromatic compound and / or a seasoning compound and / or a sweetener and / or a sweetness. Including substances and the like.

The preparation is preferably an edible composition.

The following examples of use describe the invention without limiting the scope of the invention. Unless otherwise stated, all quantities, parts and percentages are based on weight and total amount or total weight and total amount of preparation.

<Example 1>
Extraction and identification of compounds of formula (I) <A. Extraction>
2 kg of Momordica grosvenorii (also known as Siraitia grosvenori) provided by Cfm Oskar Tropitzsch in Marktredwitz, Germany, was extracted with 18 liters of methanol-MTB-ether at room temperature for 24 hours (results). Thing: 275 g of extract). Extracted from 1 kg of Momordica grosvenorii (also known as Siraitia grosvenori) provided by DAXING ANLING SNOW LOTUS HERB BIO-TECHNOLOGY in China with 10 liters of methanol at room temperature for 24 hours (result: 310 g extraction). Stuff).
<B. Concentration>
To remove polar sugars, the raw material of the extract was dissolved in 5 liters of water ethanol (9: 1 ratio) and 500 ml of adsorbent HP-20 was added. The filtered resin was rinsed with water to dissolve unwanted highly polar components. By dissolving with methanol, 37 g of a mixture of tripelten glycosides was extracted.
<C. Prefractionation by normal phase chromatography>
The separated fraction of B was separated by medium pressure chromatography under the following conditions.
-Fixed phase: Silica 60 (Merck)
-Mobile phase solvent A: CHCl3, methanol and water in a ratio of 1680: 720: 120-Mobile phase solvent B: CHCl3, methanol and water in a ratio of 1350: 900: 225-Gradient: 100% A for 40 minutes From 50% A, 10 minutes 50% A, 10 minutes 90% methanol-10% water-Column dimensions: 50x250 mm
Seven fractions were collected and evaporated. Details are shown in the table below.

<D. Prefractionation by reverse phase chromatography>
The extracted 300 g of raw material of M. grosvenorii was separated by reverse phase chromatography under the following conditions.
Conditions for separating the concentrated tripelten glycoside fraction-Fixed phase: RP-18, 40-63 μm (Merck)
-Mobile phase solvent A: Water-Mobile phase solvent B: Methanol-Column dimensions: 50x250 mm
Seven types of fractions were collected. Details are shown in the table below.

<E. Final purification by reverse phase chromatography>
The purified compounds were separated by reverse phase chromatography using the fractions extracted by the prefractionation described in Procedure D.

<F. Analytical characteristics of the isolated tripelten glycosides>
The prepared HPLC fractions (40 ml each) were collected and analyzed by HPLC-MS. Fractions containing the same compound were combined, evaporated and analyzed by HPLC-MS and NMR (1H-NMR, HH-COSY, HSQC, HMBC), depending on storage time and mass spectrum. The structure was elucidated by interpreting NMR and MS data.

<G. Identification: Analysis of compound characteristics>
The separated compounds of formula (I) were characterized by mass spectrometry and NMR spectroscopy. See FIGS. 1 to 24 for details. The compounds were identified as follows:

<Example 2>
Sensory stimulation test when the compound of formula (I) reacts with sucrose or mogroside V The separated pure compound is added to a non-carbonated mineral water (Fonsana Quelle) at a ratio of 0.4 mg / ml (400 ppm). It was dissolved. The four examiners compared the sweetness of each sample with a sucrose solution at a concentration of 20 mg / ml and a mogroside V solution at a concentration of 0.1 mg / ml (100 ppm) (separated from Momordica grosvenori by AnalytiCon). did.
The sweetness was compared as follows.
3 = sweeter than the regulated solution 2 = sweeter than the regulated solution 1 = less sweet than the regulated solution but sweet.

<Example 3>
<Example of composition>
Tables 11-14 below show examples of oral compositions containing at least one disclosed sweetener.

Claims (1)

A sweetener compound having the formula (I), wherein the sweetener compound is selected from the following group.
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl- 6-((3S, 9R, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran- 2-Iloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) heptane -3-Iloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro -2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol (Compound Bb);
(2S, 3R, 4S, 5S, 6R) -2-((2R, 3S, 4R, 5R, 6R) -6-((3S, 9R, 13R, 14S, 17R) -17-((2R, 5R)) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxy) Methyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran- 2-Iloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -4,4,9,13,14-pentamethyl-2,3,4,7 , 8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-3-yloxy) -4,5-dihydroxy-2- (hydroxymethyl) Tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol (Compound Cc);
(2S, 3R, 4S, 5S, 6R) -2-((2R, 3R, 4S, 5S, 6R) -2-((3S, 8R, 9R, 13R, 14S, 17R)) -17-((2R, 6R) 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H- Pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2-yl) -4,4,9,13,14-pentamethyl-2,3,4 , 7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [a] phenanthrene-3-yloxy) -4,5-dihydroxy-6- (hydroxy) Methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol (compound Dd);
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl- 6-((3S, 8R, 9R, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5- Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradeca Hydro-1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxy) Methyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol (Compound Ee);
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl- 6-((3S, 9R, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy) -6- (Hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro- 1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3, 4,5-Triol (Compound Gg);
(6R) -2-Hydroxy-6-((3S, 9R, 10R, 11R, 13R, 14S, 17R) -11-Hydroxy-4,4,9,13,14-Pentamethyl-3-((2R, 3R) , 4S, 5S, 6R) -3,4,5-trihydroxy-6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-) 2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra Decahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-methylheptane-3-one (Compound Hh);
(9R, 10R, 11R, 13R, 14S, 17R) -17-((2R, 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 5R) 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R)) -3,4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2- Il) -11-Hydroxy-4,4,9,13,14-Pentamethyl-4,7,8,9,10,11,12,13,14,15,16,17-Dodecahydro-1H-cyclopenta [a] ] Phenantren-3 (2H) -on (Compound Jj);
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-6-(((3R, 6R) -2-hydroxy-6-(( 3S, 9R, 10S, 13R, 14S, 17R) -3-Hydroxy-4,4,9,13,14-Pentamethyl-2,3,4,7,8,9,10,11,12,13,14 , 15, 16, 17-Tetradecahydro-1H-cyclopenta [a] phenanthrene-17-yl) -2-methylheptane-3-yloxy) -6-(((2R, 3R, 4S, 5S, 6R)- 3,4,5-Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran- 3,4,5-Triol (Compound Kk);
(3S, 9R, 10R, 13R, 14S, 17R) -17-((2R, 5R) -5-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-3-((2S, 5R) 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -6-(((2R, 3R, 4S, 5S, 6R)) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-2-yloxy) -6-hydroxy-6-methylheptan-2- Il) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran -2-Iloxy) -3,4,7,8,9,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta [a] phenanthrene-11 (2H) -one (Compound Ll) ;
(2S, 3R, 4S, 5S, 6R) -2-((2S, 3R, 4S, 5S, 6R) -4,5-dihydroxy-2-((3R, 6R) -2-hydroxy-2-methyl- 6-((3S, 9R, 10S, 13R, 14S, 17R) -4,4,9,13,14-pentamethyl-3-((2R, 3R, 4S, 5S, 6R) -3,4,5- Trihydroxy-6- (hydroxymethyl) tetrahydro-2H-pyran-2-yloxy) -2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradeca Hydro-1H-cyclopenta [a] phenanthrene-17-yl) heptane-3-yloxy) -6-(((2R, 3R, 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxy) Methyl) tetrahydro-2H-pyran-2-yloxy) methyl) tetrahydro-2H-pyran-3-yloxy) -6- (hydroxymethyl) tetrahydro-2H-pyran-3,4,5-triol (Compound Mm).