Triterpene-glycoside as sweetener or sweetener enhancer

Abstract

What claimed is a method of sweetening or enhancing sweetening effect of a composition that is administered orally to an individual by adding a specific triterpene glycoside obtained from Momordica grosvenorii (Siraitia grosvenori).

Claims

1. A method of sweetening or enhancing sweetening effect of a composition that is administered orally to an individual by adding the sweetener compound of formula (I) ##STR00021## into the composition to sweeten or enhance the sweetening effect in the composition.

2. The method of claim 1, wherein said sweetener of formula (I) is added in an amount of from about 1 to about 2,000 ppm.

3. The method of claim 1 wherein said composition represents a food composition, an oral composition or a pharmaceutical composition.

4. A method of sweetening or enhancing sweetening effect of a composition that is administered orally to an individual by adding the sweetener compound of formula (II) ##STR00022## into the composition to sweeten or enhance the sweetening effect in the composition.

5. The method of claim 4, wherein said sweetener of formula (II) is administered in the form an extract, said extract being obtained by the method of aqueous and/or alcoholic extraction of plant materials selected from the group consisting of Momordica grosvenorii (Siraitia grosvenori).

6. The method of claim 5, wherein said extract further contains at least one of the following compounds: TABLE-US-00016 Com- pound 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-cyclopenta[a]phenanthren-17-yl)-2- hydroxy-2-methylheptan-3-yloxy)-4,5-dihydroxy-6- (hydroxymethyptetrahydro-2H-pyran-3-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Com- pound 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-yloxy)- 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H- cyclopenta[a]phenanthren-17-yl)heptan-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 Com- pound 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- (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]phenanthren-3-yloxy)-4,5-dihydroxy-2- (hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Com- pound Dd (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]phenanthren-3-yloxy)-4,5-dihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Com- pound 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-tetradecahydro-1H- cyclopenta[a]phenanthren-17-yl)heptan-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 Com- pound 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]phenanthren-3-yloxy)-4,5-dihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Com- pound 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]phenanthren-17-yl)heptan-3-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Com- pound 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-tetradecahydro-1H- cyclopenta[a]phenanthren-17-yl)-2-methylheptan-3-one Com- pound Jj (9R,10R,11R,13R,14S,17R)-17-((2R,5R)-5- ((2S,3R,4S,5S,6R)-4,5-dihydroxy-3-((25,3R,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- 4,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H- cyclopenta[a]phenanthren-3(2H)-one Com- pound Kk (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]phenanthren-17-yl)-2-methylheptan-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, or Com- pound 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-tetradecahydro-1H- cyclopenta[a]phenanthren-17-yl)heptan-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.

7. The method of claim 4, wherein said sweetener of formula (II) is added in an amount of from about 1 to about 2,000 ppm.

8. The method of claim 4, wherein said composition represents a food composition, an oral composition or a pharmaceutical composition.

Description

EXAMPLES

(1) The examples which follow are intended to illustrate the present invention without limiting the invention. Unless indicated otherwise all amounts, parts and percentages are based on the weight and the total amount or on the total weight and the total amount of the preparations.

Example 1

(2) Extraction and Identification of Compounds of Formula (I)

(3) A) Extraction

(4) 2 kg dried fruits of Momordica grosvenori (Syn. Siraitia grosvenori), provided by Cfm Oskar Tropitzsch, Marktredwitz, Germany, were extracted with 181 methanol-MTB-ether at room temperature for 24 h (yield: 275 g extract). 1 kg dried fruits of Momordica grosvenori (Syn. Siraitia grosvenori), provided by DAXINGANLING SNOW LOTUS HERB BIO-TECHNOLOGY CO., LTD., China, were extracted with 101 methanol at room temperature for 24 h (yield: 310 g extract).

(5) B) Enrichment

(6) In order to remove very polar sugars the raw extract were dissolved in 51 water-methanol (9:1) and 500 ml of absorber resin HP-20 was added. The filtered resin was washed with water to elute the polar ingredients which are not wanted. Elution with methanol yielded 37 g of a mixture of triterpene-glycosides.

(7) C) Pre-Fractionation by Normal Phase Chromatography

(8) The resulted fraction of B) was then separated by medium pressure chromatography under the following conditions: stationary phase: Silica 60 (Merck) mobile phase solvent A: CHCl.sub.3-methanol-water 1680:720:120 mobile phase solvent: B CHCl.sub.3-methanol-water 1350:900:225 gradient: 100% A to 50% A in 40 min, 10 min 50% A, 10 min 90% methanol-10% water column dimension: 50250 mm

(9) Seven fractions were collected and evaporated as set out in the following Table C:

(10) TABLE-US-00002 TABLE C Fractions Fraction Volume [ml] Yield [g] C-1780-A 150 5.85 C-1780-B 220 4.72 C-1780-C 450 3.85 C-1780-D 550 2.96 C-1780-E 410 2.08 C-1780-F 500 2.32 C-1780-G 550 13.38
D) Pre-Fractionation by Reverse Phase Chromatography

(11) 300 g raw extract of M. grosvenori were separated by reverse phase medium pressure chromatography under the following conditions:

(12) Conditions of the separation of enriched triterpene glycoside fraction: stationary phase: RP-18, 40-63u (Merck) mobile phase solvent A: water mobile phase solvent B: methanol column dimension: 50250 mm

(13) Seven Fractions were collected as set out in the following Table D:

(14) TABLE-US-00003 TABLE D Fractions Fraction Volume [ml] Yield [g] H-1714-B 3000 54.06 H-1714-C 3000 32.52 H-1714-D 3000 36.69 H-1714-E 3000 36.87 H-1714-F 3000 11.25 H-1714-G 3000 3.57 H-1714-I 3000 0.96
E) Final Purification by Reverse Phase Chromatography

(15) Pure compounds were isolated by reverse phase chromatography using enriched fractions generated by pre-fractionation steps described in step D).

(16) TABLE-US-00004 TABLE 1 Conditions of the separation of C-1780-C stationary phase LichrospherSelect B. 10 m mobile phase solvent A water + 5 mM ammoniumformiat + 0.1% formic acid mobile phase solvent B acetonitril/methanol = 1:1 + 5 mM ammoniumformiat + 0.1% formic acid flowrate 80 ml/min gradient 36-65% B in 57 min detection ELSD and UV column dimension 50 250 mm used prefraction sample 3.85 g C-1780-C

(17) TABLE-US-00005 TABLE 2 Conditions of the separation of C-1780-D stationary phase LichrospherSelect B. 10 m mobile phase solvent A water + 5 mM ammoniumformiat + 0.1% formic acid mobile phase solvent B acetonitril/methanol = 1:1 + 5 mM ammoniumformiat + 0.1% formic acid flowrate 80 ml/min gradient 32-50% B in 57 min detection ELSD and UV column dimension 50 250 mm used prefraction sample 2.96 g C-1780-D

(18) TABLE-US-00006 TABLE 3 Conditions of the separation of C-1780-E stationary phase LichrospherSelect B. 10 m mobile phase solvent A water + 5 mM ammonium formiate + 0.1% formic acid mobile phase solvent B acetonitrile/methanol = 1:1 + 5 mM ammonium formiate + 0.1% formic acid flowrate 80 ml/min gradient 32-50% B in 57 min detection ELSD and UV column dimension 50 250 mm used pre-fraction sample 2.08 g C-1780-E

(19) TABLE-US-00007 TABLE 4 Conditions of the separation of C-1780-F stationary phase LichrospherSelect B. 10 m mobile phase solvent A water + 5 mM ammonium formiate + 0.1% formic acid mobile phase solvent B acetonitrile/methanol = 1:1 + 5 mM ammonium formiate + 0.1% formic acid flowrate 80 ml/min gradient 29-49% B in 57 min detection ELSD and UV column dimension 50 250 mm used pre-fraction sample 2.32 g C-1780-F

(20) TABLE-US-00008 TABLE 5 Conditions of the separation of H-1949-G stationary phase LichrospherSelect B. 10 m mobile phase solvent A water + 5 mM ammonium formiate + 0.1% formic acid mobile phase solvent B acetonitrile/methanol = 1:1 + 5 mM ammonium formiate + 0.1% formic acid flowrate 80 ml/min gradient 35-50% B in 57 min detection ELSD and UV column dimension 50 250 mm used pre-fraction sample 0.57 g H-1714-G

(21) TABLE-US-00009 TABLE 6 Conditions of the separation of C-1750-N stationary phase Kromasil C-18 mobile phase solvent A water + 0.1% formic acid mobile phase solvent B acetonitrile + 0.1% formic acid flowrate 80 ml/min gradient 20-37% B in 57 min detection ELSD and UV column dimension 50 250 mm used pre-fraction sample 1.3 g H-1714-F

(22) TABLE-US-00010 TABLE 7 Conditions of the separation of C-1743-A stationary phase Kromasil C-18 mobile phase solvent A water + 5 mM ammonium formiate + 0.1% formic acid mobile phase solvent B methanol = 1:1 + 5 mM ammonium formiate + 0.1% formic acid flowrate 80 ml/min gradient 53-62% B in 57 min detection ELSD and UV column dimension 50 250 mm used pre-fraction sample 2.08 g H-1714-F

(23) TABLE-US-00011 TABLE 8 Conditions of the separation of H-1714-G stationary phase Kromasil C-18 mobile phase solvent A water + 0.1% formic acid mobile phase solvent B acetonitrile + 0.1% formic acid flowrate 80 ml/min gradient 20-37% B in 57 min detection ELSD and UV column dimension 50 250 mm used prefraction sample 1.3 g H-1714-F
F) Analytical Characterization of Isolated Triterpene-Glycosides

(24) Fractions from preparative HPLC were collected (40 ml each) and analyzed by HPLC-MS. Fractions containing the same compound according to retention time and mass spectrum were combined, evaporated and analyzed by HPLC-MS and NMR (.sup.1H-NMR; HH-COSY; HSQC; HMBC). Structures were elucidated by interpretation of NMR and MS data.

(25) TABLE-US-00012 TABLE 9 Conditions of the HPLC-MS of isolated compounds HPLC HPLC PE series 200 MS System Applied Biosystems API 150. 165 or 365 Data system Analyst 1.3 stationary phase Phenomenex Luna C8 (2). 5 m. 50 4.6 mm flowrate 1.2 mL/min detection (+/()-ESI. Fast-Switching-mode. ELSD (Sedex 75) injection volume 10 L mobile phase: A: 5 mM ammonium formiate and 0.1% formic acid B: Acetonitril/Methanol = 1:1 + 5 mM ammonium formiate + 0.1% formic acid (pH 3) gradient time [min] % A % B 0 95 5 6 0 100 8 0 100
G) Identification: Analytical Characterization of the Compounds

(26) The isolated compounds of formula (I) are characterized through mass spectroscopy and NMR spectroscopy. The compounds were identified as:

(27) TABLE-US-00013 Com- pounds Structure and IUPAC name Com- pounds 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-cyclopenta[a]phenanthren-17-yl)-2-hydroxy-2-methylheptan- 3-yloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Com- pound Bb 0 (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- yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H- cyclopenta[a]phenanthren-17-yl)heptan-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 Com- pound 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- (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-tetradecohydro-1H- cyclopenta[a]phenanthren-3-yloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro- 2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Com- pound Dd (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]phenanthren-3-yloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro- 2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Com- pound 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-tetradecahydro-1H- cyclopenta[a]phenanthren-17-yl)heptan-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 Com- pound 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]phenanthren-3-yloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro- 2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Com- pound Gg (2S,3R,4S,5S,6R)-2-((2S,3R,4S,5S,6S)-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]phenanthren-17-yl)heptan-3-yloxy)-6-(hydroxymethyl)tetrahydro- 2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Com- pound 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-tetradecahydro-1H- cyclopenta[a]phenanthren-17-yl)-2-methylheptan-3-one Com- pound Jj (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-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]phenanthren-3(2H)-one Com- pound Kk (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]phenanthren-17-yl)-2-methylheptan-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 Com- pound Ll (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-yl)-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]phenanthren-11(2H)-one Com- pound Mm 0 (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-tetradecahydro-1H- cyclopenta[a]phenanthren-17-yl)heptan-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.

(28) For the avoidance of doubt it should be noted that when adding the extract as described above for sweetening of a composition or sweetness enhancement, Component LI is added along with all other components mentioned above.

Example 2

(29) Organoleptic Test of Compound L Against Sucrose and Mogroside V

(30) The isolated Compound LI according to formula (II) was dissolved in non-carbonated mineral water (Fonsana Quelle) in a concentration of 0.4 mg/ml (400 ppm). The sweet taste of the samples was compared by a panel of 4 panelists with a solution of sucrose in a concentration of 20 mg/ml and with a solution of the known sweetener mogroside V (isolated by AnalytiCon from Momordica grosvenori) in a concentration of 0.1 mg/ml (100 ppm).

(31) The sweetness was evaluated as follows:

(32) 3=sweeter than the control solution

(33) 2=sweetness comparable with the control solution

(34) 1=less sweet than the control solution but still sweet

(35) TABLE-US-00014 TABLE 10 Organoleptic evaluation Compound compared to sucrose compared to mogroside V Ll 3 3

Example 3

Formulation Example

(36) The following Tables 11 provides a formulation example for Compound LI:

(37) TABLE-US-00015 TABLE 11 Hard boiled candy, sugar-free; all amounts in % b.w. Composition Amount Isomalt 94.98 Xylitol 2.40 Compound Kk Compound Ll 0.01 Compound Mm Citric acid 0.050 Cherry aroma 0.25 Water Ad 100