WO 2015/082012 Al 11 June 2015 (11.06.2015) W P O P C T

Home , Cyclohexane conformation

(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2015/082012 Al 11 June 2015 (11.06.2015) W P O P C T

(51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A23L 1/236 (2006.01) C07J 17/00 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/EP2013/075724 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 5 December 2013 (05.12.2013) KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (25) Filing Language: English OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (26) Publication Language: English SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, (71) Applicant (for all designated States except US): ANA- ZW. LYTICON DISCOVERY GMBH [DE/DE]; Her- mannswerder Haus 17, 14473 Potsdam (DE). (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (72) Inventors; and GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (71) Applicants (for US only): SIEMS, Karsten [DE/DE]; UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, FeuerbachstraBe 7, 14552 Michendorf (DE). KLUGE, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, Grit [DE/DE]; Muhlenberg 608, 14959 Trebbin (DE). EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, JAKUPOVIC, Sven [DE/DE]; DilgesstraBe 24, 12249 MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, Berlin (DE). HETTERLING, Gregor [DE/DE]; Steglitzer TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, Damm 44, 121 69 Berlin (DE). TSCHIRINTZI, Fotini KM, ML, MR, NE, SN, TD, TG). [DE/DE]; Wurtembergische Strasse 3 1, 10707 Berlin (DE). Published: (74) Agent: FABRY, Bernd; IP2 Patentanwalts GmbH, — with international search report (Art. 21(3)) SchlossstraBe 523-525, 41238 Monchengladbach (DE).

(54) Title: NOVEL TRITERPENE-GLYCOSIDES AS SWEETENERS OR SWEETENER ENHANCERS

Figure 1: H-NM of compound Aa

- (57) Abstract: Suggested are triterpene-glycoside compounds, which are obtainable by the extraction of Momordica grosvenorii © (Siraitia grosvenori) which are useful as a sweetener or sweetener enhancer in preparations and compositions, especially oral edible o compositions. NOVEL TRITERPENE-GLYCOSIDES AS SWEETENERS OR SWEETENER ENHANCERS

FIELD OF INVENTION

The invention relates t o novel triterpene-glycoside compounds, which are obtainable by the extraction of Momordica grosvenorii (Siraitia grosvenori) and its physiologically acceptable salts which are useful as a sweetener or sweetener enhancer in preparations and composi¬ tions, especially oral edible compositions.

STATE OF THE ART

Sweetness is one of the primary taste and cravings of both animals and humans. The univer¬ sal use of naturally occurring and synthetic sweeteners to satisfy this natural craving has not been met without its accompanying physiological disadvantages, e.g. obesity, nutritional imbalance and dental decay. To overcome these unwanted disadvantages considerable re- search efforts and expenditures have been made to develop alternative compounds, e.g. as substitute for the naturally occurring sweeteners or synthetic sweeteners which have no food value and are free of caloric input. While these artificial sweeteners enjoyed a wide use, and fulfilled the requirements of a sweet taste with no food value, and could be used without providing calories or damaging teeth, they were frequently found to possess inher- ent disadvantages that prevented their use for their intended purpose, e.g. because of their toxicity (p-ethoxyphenylurea) or chromosome damage and bladder trouble (sodium cycla- mate). Thus, these sweeteners could not be safely recommended for use as a sweetener and are apparently unacceptable for consumption. Saccharin compounds are also common¬ ly used as artificial sweeteners, since cyclamates have been come under governmental re- strictions. Although saccharin compounds possess sweetness characteristics, they are unde¬ sirable as the sole sweetening agent in most food and beverage compositions because of the lingering bitter aftertaste perceived by most users. While saccharin and the cyclamates have been in common use as artificial sweetening agents for a number of years, there has been more recently discovered a series of new artificial sweeteners.

For example, Horowitz and Gentili, US 3,087,821, teach the use of various dihydrochalcones having sugar substituents (dihydrochalcones glycosides) as sweetening agents. All sweet dihydrochalkones have a licorice like aftertaste and linger in the mouth for some time.

Siraitia grosvenori (Luo han guo), a member of the Cucurbitaceae family, is a plant native t o some regions of southern Asia and China. The sweet taste of fruits of luo han guo mainly comes from triterpene glycosides generally known as mogrosides. There are a number of mogrosides identified in luo han guo but generally mogroside V (CAS No: 88901-36-4) has the highest concentration compared t o others (Table 1). Mogrol glycosides have the same core molecule— mogrol or oxo-mogrol and differ from each other by number and type of glycosidic residues bonded t o mogrol or oxo-mogrol molecules (US 2012/0059071, Kasai et al. Agric.Biol.Chem. (1989), 3347-3349), Matsumoto et. al. Chem. Pharm. Bu.. (1990) 2030- 2032. Several mogrosides taste very sweet, often >100x sweeter than sucrose, including the major triterpen glycoside of Siraitia grosvenori, mogroside V, and its isomer iso-mogroside V (US2011/0027413), but all of them have a certain bitter aftertaste.

Major mogrosides present in Luo han guo fruits are compiled in the following Table A.

Table A Mogrosid

Leaves of Stevia rebaudiana are well known for its sweet taste due t o its content of sweet diterpene glycosides. One of the major sweet compounds from stevia, Rebaudioside A, is approved as natural sweetener in US (since 2008) und EU (since 2011). Apart from its sweet taste, all sweeteners from stevia have a slower onset and longer duration than that of sugar, and a bitter or licorice-like aftertaste at high concentrations (Lemus-Mondaca et al. Food Chemistry 132 (2012) 1121-1132).

Another example is Symrise AG, EP 2529633 Al, which relates t o triterpenes and triterpene glycosides and/or physiologically acceptable salts thereof. The triterpenes are, preferably naturally occurring triterpenes and triterpene glycosides from Mycetia balansae, for gener ating a sweet impression in an orally consumable formulation or for reinforcing the sweet impression of an orally consumable formulation. These triterpene-glycosides differ in structure from the triterpenes claimed in the present invention.

Accordingly, it is a primary object of the present invention t o provide novel sweetener co m pounds and its physiologically acceptable salts, which have a positive sweet benefit in food and oral compositions. In particular, the object was t o provide sweetener compounds which are capable t o provide sweetness t o consumable compositions in a way, that the balance between the degree of sweetness and the amount which has t o be administered t o obtain a sweet effect is comparable low, t o overcome the aforesaid disadvantages associated with the prior art sweetener. It is another object of the present invention t o provide sweetener compounds without astringent or bitter-taste aftertaste. The sweetener compounds t o be specified should be toxicologica lly safe, effective already at relative ly low concentrations, wel l tolerated by the digestion, sta ble (in particu la r in norma l cosmetic and/or pha rmaceut i ca l form ulations), and easy t o form ulate and economica l t o produce.

In the cou rse of extensive studies on sweeteners, the present inventors succeeded in the isolation of novel sweetener com pou nds of form ula (I) and found that these sweetener com pounds of form ula ( I) show astonishingly good and strong sweetness when com pared with that of sucrose and mogroside V. Surprisingly, it has been further observed that the sweetener com pounds of form ula ( I) have significa ntly less negative aftertaste at all and have high sweete ning power.

DESCRI PTION O F THE INVENTION

The su b ect of the invention relates t o a sweetener com pound of form ula ( I)

(I) whe rei n R1 R2, R3 are independently of one another and denote hydrogen, hydroxyl, carbonyl or a suga r moiety selected from the group consisti ng of a monosaccha ride and/or o li gosaccha ride.

Prefera bly in the sweetener com pound of form ula ( I) the monosaccha ride and/or the monosaccha ride units of the oligosaccha ride are selected from the grou p consisting of fructose, glucose, sucrose, xylose, maltose, mannose, rha mnose, galactose, lactose, gentiobiose, sophorose, -Glucopyra nosyl-(l-2)-[p -Gl ucopyra nosyl-(l-6)]-p -gl ucopyra nose, cel lobiose, mannitol, sorbitol, xylitol or arabitol, glucuronic acid, quinovose, arabinopyra nose, arabinofura nose, xylopyra nose, xylofu ranose and/or apiose (2,3,4-tri hydroxy-3-(hyd roxymethyl)buta nal), and whe rei n the oligosaccha ride consists of 2 t o 5 monosaccha ride units.

The term "monosaccha ride" mea ns the sim plest form of suga r. Monosaccha rides are the most basic units of biologica lly importa nt ca rbohydrates. Exa mples of monosaccha rides in clude glucose (dextrose), fructose (levulose), galactose, xylose and ribose. Monosaccha rides are the bui lding blocks of disaccha rides (such as sucrose) and polysaccha rides (such as cel lu lose and sta rch). Further, each ca rbon atom that supports a hydroxyl group (except for the first and last) is chira l, givi ng rise t o a number of isomeric forms all with the sa me chemica l form ula . For insta nce, galactose and glucose are both aldohexoses, but have different chem ica l and physica l properties.

The term "oligosaccha ride" represents a kind of a saccha ride polymer contai ning a sma ll num ber of 2 t o 10, prefera bly 2 t o 5 of suga r units (monosaccha ride units) which are li nked together. The monosaccharides of the oligosaccharides are usually linked with each other through a glycosidic bond.

The term "sugar moiety" is equal t o the term sugar moiety component or unit.

The sugar moiety of the present invention may be in its simplest form, preferably, represented b the unit formula (II):

( ) wherein D is 0 , S or N

X, Y and Z are independently of one another and denote hydrogen, hydroxyl, carbonyl or another sugar moiety, which is another unit represented by formula (ll).The sugar moiety is preferably linked t o formula (I) through an oxygen or a nitrogen or a sulphur atom, more preferably an oxygen atom, which is represented in formula (II) by the integer D. In the pre ferred embodiments of the present invention, in case that Ri, R2, 3 are independently sugar moieties, the compounds are linked t o each other, preferably, through an oxygen atom.

The three-dimensional structure of a monosaccharide can be represented in four different forms: a) The Fischer projection is a systematic way of drawing the skeletal formula of an acyclic monosaccharide so that the handedness of each chiral carbon is well specified. Each stereoisomer of a simple open-chain monosaccharide can be identified by the positions (right or left) in the Fischer diagram of the chiral hydroxyls (the hydroxyls attached t o the chiral carbons), b) Haworth projection: In this diagram, the a-isomer has the -OH of the anomeric carbon below the plane of the carbon atoms, and the β-isomer has the -OH of the anomeric carbon above the plane. Pyranoses typically adopt a chair conformation, simi lar t o cyclohexane. In this conformation, the a-isomer has the -OH of the anomeric carbon in an axial position, whereas the β-isomer has the OH- of the anomeric carbon in equatorial position, c) A more realistic illustration is the chair form, which show the angulated for mation of the carbon chains and d) at least the absolute stereo-chemical illustration of the, e.g. cyclohexane conformation is also common:

1 Different illustrations of alpha-D-Gl ucopyra nose : Tollens (1); Haworth (2); chair (3); absol ute stereo (Source : Wikepedia : http ://de.wikipedia .org/wiki/Monosaccha ride)

As t o form ula ( II), the suga r unit is illustrated as a pla nar moiety, and mea ns that the suga r unit in the present invention may possess all possi ble stereo-isomeric forms, and is not restricted t o a certain isomeric form in first line.

Preferred embodiments of the invention

(1) In a preferred embodi ment, a com pound of form ula (I) possess a suga r unit of form ula (II) at least one t imes (monosaccha ride). In a preferred embodiment the suga r unit of form ula ( II) is a repeated suga r unit, which is repeated two, three, four or five times which are li nked together t hrough the oxygen atom of the ca rbohydrate.

(2) In a preferred embodi ment the suga r unit of form ula ( II) is only one time represented in form ula (I), which is either R R or R . 1 2 3 (3) In a preferred embodiment of the invention R R of form ula ( I) are independently of 1 2 one another and denote hyd rogen, hyd roxyl, ca rbonyl or a suga r moiety selected from

the group consisting of a monosaccha ride and/or oligosaccha ride and R3 of form ula (I) denote hydrogen, hyd roxyl or ca rbonyl. The preferred monosaccha ride and/or the monosaccha ride units of the oligosaccha ride are selected from the group consisti ng of fructose, glucose, sucrose, xylose, maltose, mannose, rha mnose, galactose, lactose, gentiobiose, sophorose, β- Ιυ ρ ηο Ι-(1-2)-[ β -Glucopyra nosyl-(l-6)]^ glucopyra nose, cel lobiose, mannitol, sorbitol, xylitol or arabitol, glucu ronic acid, quinovose, arabinopyra nose, arabinofu ranose, xylopyra nose, xylofu ranose and/or apiose (2,3,4-tri hydroxy-3-(hyd roxymethyl)buta nal). Glucose, maltose, galactose, arabinopy ranose and xylopyra nose are preferred, and glucose, galactose, arabinopyra nose and xylopyra nose are most preferred as suga r moiety.

(4) In a preferred embodiment of the invention R R of form ula ( I) are independently of 1 2 one another and denote hyd rogen, hyd roxyl, ca rbonyl or a suga r moiety selected from the group consisting of a monosaccha ride and/or oligosaccha ride which is selected from the group consisti ng of fructose, glucose, sucrose, xylose, maltose, mannose, rha mnose, galactose, lactose, ce llobiose, gentiobiose, sophorose, β- Ιυ ρ ηο Ι-(1- 2)-^-Gl ucopyra nosyl-(l-6)]^-gl ucopyra nose, mannitol, sorbitol, xylitol or arabitol, glucuronic acid, quinovose, arabinofu ranose, xylopyra nose, xylofu ranose and/ or ap i ose (2,3,4-trihydroxy-3-(hydroxymethyl)buta nal),

and R3 of form ula (I) denote hydrogen, hyd roxyl or ca rbonyl. (5) Preferred com ponent for the suga r moiety are fructose, glucose, sucrose, maltose, galactose, ara binopyra nose and xylopyra nose, and glucose, arabinopyra nose and xy lopyra nose are most preferred as suga r moiety.

(6) In another preferred embodi ment R and R2 are independently of one another and denote a monosaccha ride, which are prefera bly a glucose and /or arabinopyra nose and/ or xylopyra nose.

(7) In another preferred embodi ment R and R2 are independently of one another and denote an oligosaccha ride, in which the monosaccha ride units are prefera bly a glucose and/ or galactose and /or arabinopyra nose and/ or xylopyra nose. Prefera bly, the o li gosaccha ride contai ns one, two, t hree or four units of glucose and / or galactose and/ or arabinopyra nose and/ or xylopyra nose. More prefe rably, the oligosaccha ride co n tai ns one, two or t hree units of glucose.

(8) In another preferred embodi ment R3 is hydrogen and R1 R2 of form ula ( I) are inde pendently of one another and denote hydrogen, hydroxyl, ca rbonyl or a suga r moiety selected from the group consisti ng of a monosaccha ride and/or oligosaccha ride which is selected from the grou p consisting of fructose, glucose, sucrose, xylose, maltose, mannose, rha mnose, galactose, lactose, cel lobiose, mannitol, sorbitol, xylitol or arabitol, glucuronic acid, quinovose, arabinopyra nose, arabinofu ranose, xylopyra nose, xylofura nose and/ or apiose (2,3,4-tri hydroxy-3-(hydroxymethyl)buta nal).

(9) In another preferred embodi ment R3 is hydrogen and R1 R2 of form ula ( I) are inde pendently of one another and denote a suga r moiety selected from the group co nsist ing of a monosaccha ride and/or oligosaccha ride with monosaccha ride units which are selected from the group consisting fructose, glucose, sucrose, xylose, maltose, mannose, rha mnose, galactose, lactose, ge ntiobiose, sophorose, -Glucopyra nosyl-(l-2)-[p -Gl ucopyra nosyl-(l-6)]-p -glucopyra nose, cel lobiose, mannitol, sorbitol, xylitol or ara bitol, glucu ronic acid, quinovose, arabinopyra nose, arabinofura nose, xylopyra nose, xylofura nose and/or apiose (2,3,4-trihyd roxy-3-(hyd roxymethyl)buta nal).

(10) In a preferred embodi ment of the invention R and R2 of form ula (I) are independently of one another and denote hydroxyl or a suga r moiety selected from a monosaccha ride and/or oligosaccha ride,

• wherein the monosaccha ride and/or the monosaccha ride units of the oligosaccha ride are selected from the group consisting of glucose, 2-glucopyra nosyl-glucose, 3-glucopyra nosyl-glucose, 4-glucopyra nosyl-gl ucose, 6-glucopyra nosyl-gl ucose, or glucopyra nosyl-(l->2)-[gl ucopyra nosyl-(l->6)]-gl ucose, and

• whereby in case of the oligosaccha ride, the monosaccha ride units of the oligosac cha ride are lin ked via glycosidic bonds t o each other, and

• R3 denote hyd rogen, hydroxyl or ca rbonyl .

(11) In a further preferred embodi ment of the invention in case R2 of com pou nd of form ula (I) is an oligosaccha ride with 2 monosaccha ride units (disaccha ride), and wherein the

monosaccha ride units of the disaccha ride of R2 are lin ked via glycosidic bonds t oget h er, which is not a l - 6 lin king.

(12) Fu rthermore, in a preferred embodi ment R2 is an oligosaccha ride with 2 monosaccha-

ride units (disaccha ride), and R3 denote hyd rogen or ca rbonyl . (13) In another preferred embodiment of the invention Ri denotes hydrogen, hydroxyl,

ca rbonyl or an oligosaccha ride with 2, 3, 4 or 5 monosaccha ride units, and R2 is an o li

gosaccha ride with 2 monosaccha ride units (disaccha ride), and R3 denotes hyd roxyl.

(14) In a preferred embodiment of the invention wherein in case R2 is an oligosaccha ride with 3 monosaccha ride units (trisaccha ride), then

• R is ca rbonyl and/or

• R3 is not hydroxyl or ca rbonyl or • R3 is hydroxyl and Ri is an oligosaccha ride with 2, 4 or 5 monosaccha ride units, wherein the monosaccha ride units of the oligosaccha ride of Ri are lin ked via glyco side bonds together which is not a l - 6 or l - 4 linking.

(15) In a preferred embodiment of the invention Ri is a monosaccha ride or an oligosaccha ride with at least 3 monosaccha ride units, and

• R2 is an oligosaccha ride with 3 monosaccha ride units (trisaccha ride), and

• R3 is ca rbonyl .

(16) In a preferred embodiment of the invention Ri is an oligosaccha ride with 2, 4 or 5 monosaccha ride units, but not with 3 monosaccha ride units.

(17) In a preferred embodi ment of the invention R2 is an oligosaccha ride with 2 t o 5 mono saccha ride units, but not a (si ngle) monosaccha ride.

(18) In a preferred embodi ment of the invention whe n R2 is ca rbonyl, then

• R3 is not ca rbonyl or

• R3 is hydroxyl .

(19) In another preferred embodi ment of the sweetener com pou nd of form ula (I), in case

• R denotes a suga r moiety with two suga r units, and

• R2 denotes a suga r moiety with three suga r units, the n

• R3 denotes a hyd rogen or ca rbonyl group, prefera bly a hyd roge n and/ or

• the glycosidic bonds in the suga r units in Ri differ from that in mogroside V and iso- mogroside V with disaccha ride moieties li nked via 1 - 4 or l - 6 glycosidic bond, and not l - 2 glycosidic bond.

(20) In another preferred embodi ment of the sweetener com pou nd of form ula (I), in case

• R denotes a suga r moiety with two suga r units, and

• R2 denotes a suga r moiety with three suga r units, and

• R3 denotes hydrogen.

Compounds of particular interest

Of particula r interest are the com pounds of Form ula ( I) identified as:

Compound A

3, ll-dihydroxy-4,4,9,13, 14-penta methyl-2,3,4,7,8,9,10, ll,12, 13,14, 15,16, 17- tetradeca hydro-lH-cyclopenta [a] phena nthren-17-yl)-2-hydroxy-2-methylhepta n-3-yloxy)- 4,5-dihyd roxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-3-yloxy)-6- (hyd roxymethyl)tetra hydro-2H-pyra n-3,4,5-triol (Compound A)

Compound B 4,5-dihydroxy-2-(2-hydroxy-2-methyl-6-((4A9A3A4-pentamethyl-3-(3A5-trihydroxy-6- ((3A5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-2H- pyran-2-yloxy)-2,3,4,7,8,9,10,H,12,13,14,15,16,17-tetradecahydro-lH- cyclopenta[a]phenanthren-17-yl)heptan-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 B)

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,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-3-yloxy) 4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

(Compound C)

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-yl)-4,4,9,13,14- pentamethyl-2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH- cyclopenta[a]phenanthren-3-yloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol Compound E 2-(4,5

(Com pou nd E)

Compound F 2-((6-(6-(3-(4,5-dihyd roxy-6-(hyd roxymethyl)-3-(3,4,5-trihydroxytetra hydro-2H-pyra n- yloxy)tetra hyd ro-2H-pyra n-2-yloxy)-ll-hyd roxy-4,4,9 13,14-penta methyl- 2,3,4,7,8,9, 10,ll, 12,13, 14,15, 16,17-tetradeca hydro-lH-cyclopenta [a] phena nthren-17 hyd roxy-2-methyl hepta n-3-yloxy)-3,4-di hydroxy-5-(3,4,5-trihydroxy-6- (hydroxymethyl)tetra hydro-2H-pyra n-2-yloxy)tetra hyd ro-2H-pyra n-2-yl)methoxy)-6- (hydroxymethyl)tetra hydro-2H-pyra n-3,4,5-triol

(Com pound F) Compound G 2-(4,5-dihydroxy-2-(3-hydroxy-2-methyl-6-(4A9A3A4-pentamethyl-3-(3A5-trihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2,3A7,8,9,10,ll,12,13,14,15,16,17- tetradecahydro-lH-cyclopenta[a]phenanthren-17-yl)heptan-2-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3A5- triol

(Compound G)

Compound H 2-hydroxy-6-(ll-hydroxyA4,9,13,14-pentamethyl-3-(3A5-trihydroxy-6-((3A5-trihydroxy- 6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-2H-pyran-2-yloxy)- 2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-17-yl)-2- methylheptan-3-one

(Compound H) 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)-ll-hydroxy-4,4,9,13,14-pentamethyl- 4,7,8,9,10,ll,12,13,14,15,16,17-dodecahydro-lH-cyclopenta[a]phenanthren-3(2H)-one

(Compound J)

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,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-17-yl)-2- methylheptan-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 K) Compound L 17-(5-(4,5-dihydroxy-3-(3A5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-6- ((3A5-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-lH-cyclopenta[a]phenanthren-ll(2H)-one

(Compound L)

Compound M 2-(4,5-dihydroxy-2-(2-hydroxy-2-methyl-6-(4,4,9,13,14-pentamethyl-3-(3,4,5-trihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2,3,4,7,8,9,10,ll,12,13,14,15,16,17- tetradecahydro-lH-cyclopenta[a]phenanthren-17-yl)heptan-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 M) The compounds A to M are represented in planar forms, which is especially preferred. That means that all compounds A to M as represented herewith include all isomeric forms which are possible for the respect compound. Isomers contain the same number of atoms of each element, but have different arrangements of their atoms in space. Isomers do not necessari- ly share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like positional isomers, cis-trans isomers and enantio- mers, etc.. There are two main forms of isomerism: structural isomerism and stereoisomer ism (spatial isomerism).

Every isomer of the compounds A to M of formula (I) is herewith also included by the above given structures and are preferred in the sense of the present invention.

In particular, the following isomers of the compounds of formula (I) are preferred:

Compound Aa (2S,3R,4S,5S,6R)-2-((2S,3R,4S,5S,6R)-2-((3R,6R)-6-((3S,8S,9R,llR,13R,14S,17R)-3,ll- dihydroxy-4,4,9,13,14-pentamethyl-2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH- 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

(Compound Aa)

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-yloxy)-2,3,4,7,8,9,10,ll,12,13,14,15,16,17- tetradecahydro-lH-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 (Compound Bb)

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- (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-lH-cyclopenta[a]phenanthren-3-yloxy)-4,5-dihydroxy-2- (hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5- triol

(Compound Cc) Compound 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-lH-cyclopenta[a]phenanthren-3-yloxy)-4,5-dihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5- triol

(Compound Dd)

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,ll,12,13,14,15,16,17- tetradecahydro-lH-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 (Compound Ee)

Compound Ff (2S,3R,4S,5S,6R)-2-((2R,3R,4S,5S,6R)-2-((3S,8S,9R,llR,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)-ll-hydroxy-4, 4,9,13, 14-pentamethyl- 2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-3-yl 4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

(Compound Ff) 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)-4A9,13,14-pentamethyl-3-((2R,3R,4S,5S,6R)-3A5-trihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2,3A7,8,9,10,ll,12,13,14,15,16,17- tetradecahydro-lH-cyclopenta[a]phenanthren-17-yl)heptan-3-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3A5- triol

(Compound Gg)

Compound Hh (6R)-2-hydroxy-6-((3S,9R,10R,llR,13R,14S,17R)-ll-hydroxyA4,9,13,14-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,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-17-yl)-2- methylheptan-3-one

(compound Hh) Compound Jj (9R,10R,llR,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)-ll-hydroxy- 4,4,9,13,14-pentamethyl-4,7,8,9,10,H,12,13,14,15,16,17-dodecahydro-lH- cyclopenta[a]phenanthren-3(2H)-one

(Compound Jj)

Compound 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,ll,12,13,14,15,16,17-tetradecahydro-lH-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

(Compound Kk) Compound LI

(3S,9R, 10R, 13R,14S, 17R)-17-((2R,5R)-5-((2S,3R,4S,5S,6R)-4,5-dihyd roxy-3-((2S,3 R,4S,5S,6R)- 3,4,5-tri hydroxy-6-(hyd roxymethyl)tetra hydro-2H-pyran-2-yloxy)-6-(((2R,3 R,4S,5S,6R)-3,4,5- trihyd roxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)methyl)tetra hydro-2H-pyra n-2- yloxy)-6-hyd roxy-6-methyl hepta n-2-yl)-4,4,9,13, 14-penta methyl-3-((2R,3 R,4S,5S,6R)-3,4,5- trihyd roxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)-3,4, 7,8,9, 10,12, 13,14, 15,16, 17- dodeca hydro-lH-cyclopenta [a] phena nth ren-ll(2H)-one

(Com pound LI)

Compound M m (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-penta methyl-3-((2R,3R,4S,5S,6R)-3,4,5-tri hydroxy-6- (hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)-2,3,4,7,8,9, 10,ll, 12,13, 14,15, 16,17- tetradeca hydro-lH-cyclopenta [a] phena nthren-17-yl)hepta n-3-yloxy)-6-(((2R,3 R,4S,5S,6R)- 3,4,5-tri hydroxy-6-(hyd roxymethyl)tetra hydro-2H-pyran-2-yloxy)methyl)tetra hydro-2H- pyra n-3-yloxy)-6-(hydroxymethyl)tetra hyd ro-2H-pyra n-3,4,5-triol.

(Com pound M m) The compounds of formula (I) when comprising two or more sugar component moieties (di- or oligosaccharide), the sugar units are linked with each other through a glycosidic bond. A glycosidic bond is a type of covalent bond that joins a carbohydrate (sugar) molecule to a n other group, which may or may not be another carbohydrate. A glycosidic bond is formed between the hemiacetal group of a saccharide (or a molecule derived from a saccharide) and the hydroxyl group of some organic compound such as an alcohol. If the group attached to the carbohydrate residue is not another saccharide it is referred to as an aglycone. If it is another saccharide, the resulting units can be termed as being at the reducing end or the terminal end of the structure. This is a relative nomenclature where the reducing end of the di- or polysaccharide is towards the last anomeric carbon of the structure, and the terminal end is in the opposite direction.

The glycosidic bonds of the triterpene-glycoside compounds of the present invention are as compiled in Table B:

Table B Glycosidic bonds

Furthermore, the invention relates to an extract comprising one or more of a compound of formula (I), wherein the extract is obtainable by the method of aqueous and / or alcoholic extraction of the plant Momordica grosvenorii (Synononym Siraitia grosvenori).

The thus obtained extract preferably, comprises at least a compound of formula (I) selected from the group consisting of: • (2S,3R,4S,5S,6R)-2-((2S,3R,4S,5S,6R)-2-((3R,6R)-6-((3S,8S,9R,llR,13R,14S,17R)-3,ll- dihydroxy-4,4,9,13,14-pentamethyl-2,3,4,7,8,9,10,ll,12,13,14,15,16,17- tetradecahydro-lH-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 (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)-4A9,13,14-pentamethyl-3-((2R,3R,4S,5S,6R)-3A5-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,ll,12,13,14,15,16,17- tetradecahydro-lH-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 (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-methylheptan-2-yl)-4,4,9,13,14-pentamethyl- 2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-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,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-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-tetradeca hydro-lH-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 (compound Ee)

(6R)-2-hyd roxy-6-((3S,9R,10R, llR, 13R,14S, 17R)-ll-hyd roxy-4,4,9, 13,14-penta methyl- 3-((2R,3R,4S,5S,6R)-3,4,5-tri hydroxy-6-(((2R,3R,4S,5S,6R)-3,4,5-tri hydroxy-6- (hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)methyl)tetra hyd ro-2H-pyra n-2-yloxy)- 2,3,4,7,8,9, 10,ll, 12,13, 14,15, 16,17-tetradeca hydro-lH-cyclopenta [a] phena nthren-17 yl)-2-methylhepta n-3-one (com pou nd Hh)

(9R, 10R,llR, 13R,14S, 17R)-17-((2R,5R)-5-((2S,3R,4S,5S,6R)-4,5-dihyd roxy-3- ((2S,3 R,4S,5S,6R)-3,4,5-tri hydroxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)-6- (((2R,3 R,4S,5S,6R)-3,4,5-tri hydroxy-6-(hydroxymethyl)tetra hydro-2H-pyra n-2- yloxy)methyl)tetra hydro-2H-pyra n-2-yloxy)-6-hyd roxy-6-methylhepta n-2-yl)-ll- hyd roxy-4,4,9, 13,14-penta methyl-4,7,8,9, 10,ll, 12,13, 14,15, 16,17-dodeca hyd ro-lH- cyclopenta [a] phena nthren-3(2H)-one (com pou nd Jj)

(2S,3 R,4S,5S,6R)-2-((2S,3R,4S,5S,6R)-4,5-dihydroxy-2-((3 R,6R)-2-hyd roxy-6- ((3S,9R, 10S, 13R, 14S,17R)-3-hydroxy-4,4,9, 13,14-pentamethyl- 2,3,4,7,8,9, 10,ll, 12,13, 14,15, 16,17-tetradeca hydro-lH-cyclopenta [a] phena nthren-17 yl)-2-methylhepta n-3-yloxy)-6-(((2R,3 R,4S,5S,6R)-3,4,5-tri hydroxy-6- (hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)methyl)tetra hyd ro-2H-pyra n-3-yloxy)-6- (hyd roxymethyl)tetra hydro-2H-pyra n-3,4,5-triol (com pou nd Kk)

(3S,9R, 10R,13R, 14S,17R)-17-((2R,5 R)-5-((2S,3 R,4S,5S,6R)-4,5-dihydroxy-3- ((2S,3 R,4S,5S,6R)-3,4,5-tri hydroxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)-6- (((2R,3 R,4S,5S,6R)-3,4,5-tri hydroxy-6-(hydroxymethyl)tetra hydro-2H-pyra n-2- yloxy)methyl)tetra hydro-2H-pyra n-2-yloxy)-6-hyd roxy-6-methylhepta n-2-yl)- 4,4,9, 13,14-penta methyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihyd roxy-6- (hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)-3,4,7,8,9, 10,12, 13,14, 15,16, 17- dodeca hydro-lH-cyclopenta [a] phena nth ren-ll(2H)-one (com pou nd LI)

(2S,3 R,4S,5S,6R)-2-((2S,3R,4S,5S,6R)-4,5-dihydroxy-2-((3 R,6R)-2-hyd roxy-2-methyl-6- ((3S,9R, 10S, 13R, 14S,17R)-4,4,9, 13,14-penta methyl-3-((2R,3R,4S,5S,6R)-3,4,5- trihyd roxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)- 2,3,4,7,8,9, 10,ll, 12,13, 14,15, 16,17-tetradeca hydro-lH-cyclopenta [a] phena nthren-17 yl)hepta n-3-yloxy)-6-(((2R,3 R,4S,5S,6R)-3,4,5-trihyd roxy-6-(hyd roxymethyl)tetra hydro- 2H-pyra n-2-yloxy)methyl)tetra hyd ro-2H-pyra n-3-yloxy)-6-(hydroxymethyl)tetra hyd ro- 2H-pyra n-3,4,5-triol (com pound M m).

The prese nt invention also relates t o prepa rations, com prising one, two, three or more of a sweetener com pou nd of form ula (I). Such a prepa ration used t o com prise f urther ingredi ents such as aroma com pounds and/ or flavou ring age nts and/or sweeteners and/ or sweet- tasting su bsta nces.

Preferred aroma com pounds, flavouring agents, sweeteners and sweet-tasti ng substa nces are descri bed below in detai led .

The prepa ration of the present invention com prising at least one sweete ner com pound of form ula ( I) and ca n be used t o impart a desi rable sweetness and/ or flavor t o a variety of ora l and food com positions and pha rmaceutica l com positions, such as beverages, edible foodstuff, dentifrices, lipsticks and the like, which may or may not be ingestible, with or without the use of other flavora nts and sweeteners. The prese nt invention also relates t o a variety of ora l and food com positions and the like embodyi ng at least one com pou nd of form ula ( I) as sweetener and/ or flavoring agent.

The sweetener of this invention finds application in the wide range of edible substa nces genera lly, pri marily in food com positions such as candies, confections and processed foods, and beverages such as beer and soft drin ks. It is also wel l suited for imparti ng a sweet flavor t o other edible substa nces such as medici nes, tooth paste, adhesives for sta mps and enve lopes, anima l feeds and baits and the like. These exa mples are given solely for illustration and it is not wished t o limit the scope of this invention t o sweetening any particula r type or types of edi ble materia ls. As a genera l rule, the present sweetener may be used in any ap plication where a sweet taste is desi red . The present sweetener may be used alone or in com bination with other sweeteners, nutritive or non nutritive. Also, if desired, binders or dil uents may be added t o the sweetener. This is not usua lly necessa ry, however, as the sweetener is a solid having excel lent hand li ng properties. This makes admixi ng the sweet en er with an edible su bsta nce a sim ple conventiona l ope ration. The sweetener may be mixed with the edible su bsta nce as a solid or as a sol ution, if desi red .

The inventions further refers t o the use of a sweetener com pou nd of form ula ( I) t o sweet or enha nce the sweeting effect in com positions or preparations which are admi nistered t o an individ ual in an effective amount sufficient t o produce the desi red degree of sweetness. Thus the invention further relates t o a method for providing a sweetening effect and/or an enha nced sweeteni ng effect in com positions, com prising ad ministeri ng t o an individua l a sweetener com pound of form ula (I) in an effective amount sufficient t o prod uce the desired degree of sweetness.

The effective amount is prefera bly from 1 ppm t o 2000 ppm, based on the tota l weight of the com position and the tota l su m of all com pound of form ula ( I).

The food, ora l and pha rmaceutica l com positions w ill be further described in detailed.

FOOD COMPOSITIONS

Food com positions according t o the invention are any prepa rations or com positions which are suita ble for consu mption and are used for nutrition or enjoyment purposes, and are genera lly products which are intended t o be introd uced into the human or anima l ora l cavi ty, t o remai n there for a certai n t ime and then eithe r be eaten (e.g. ready-to-eat foodstuffs or feeds, see also herein below) or removed from the ora l cavity again (e.g. chewing gums). Such prod ucts incl ude any substa nces or products which in the processed, partia lly pro cessed or unprocessed state are t o be ingested by huma ns or anima ls. They also include substa nces which are added t o ora lly consuma ble products during thei r manufacture, prep aration or treatment and which are intended t o be introd uced into the huma n or animal ora l cavity.

The food com positions accordi ng t o the invention also incl ude substa nces which in the u n cha nged, treated or prepa red state are t o be swallowed by a huma n or animal and then digested; in this respect, the ora lly consuma ble products according t o the invention also incl ude casings, coati ngs or other enca psu lations which are t o be swallowed at the sa me time or which may be expected t o be swallowed . The expression "ora lly consu mable prod uct" cove rs ready-to-eat foodstuffs and feeds, that is t o say foodstuffs or feeds that are al ready com plete in terms of the su bsta nces that are importa nt for the taste. The expressions "ready-to-eat foodstuff" and "ready-to-eat feed" also include drin ks as well as solid or semi- solid ready-to-eat foodstuffs or feeds. Exa mples which may be mentioned are frozen prod ucts, which must be thawed and heated t o eati ng tem perature before they are eaten . Prod ucts such as yoghu rt or ice-crea m as well as chewi ng gums or hard ca ramels are also incl ud ed among the ready-to-eat foodstuffs or feeds.

Preferred food com positions accordi ng t o the invention also incl ude "semi-fi nished products" . Within the context of the present text, a semi-fi nished product is t o be understood as being an ora lly consu mable prod uct which, beca use of a very high content of flavou rings and taste-im parti ng substa nces, is unsuita ble for use as a ready-to-eat ora lly consuma ble product (in particu la r foodstuff or feed). Only by mixing with at least one further constituent (e .g. by red uci ng the concentration of the flavou rings and taste-i mparting su bsta nces in question) and optiona lly f urther process steps (e.g. heati ng, freezi ng) is the semi-fi nished product converted into a ready-to-eat ora lly consu mable prod uct (in particula r foodstuff or feed). Exa mples of semi-finished products which may be mentioned here are

Food com position accordi ng t o the invention prefera bly com prises one or more prepa ra tions for nutrition or enjoyment purposes. These include in particula r (red uced-ca lorie) baked goods (e.g. bread, dry biscuits, ca kes, other baked articles), confectionery (e.g. choco lates, chocolate bars, other products in bar form, fruit gums, dragees, hard and soft ca ra mels, chewing gum), non-a lcoholic drin ks (e.g. cocoa, coffee, green tea, black tea, (green, black) tea drin ks enriched with (green, black) tea extracts, rooibos tea, other herba l teas, fruit-containing soft drin ks, isotonic drinks, refreshi ng drin ks, necta rs, fruit and vegeta ble juices, fruit or vegeta ble juice prepa rations), insta nt drin ks (e.g. insta nt cocoa drinks, insta nt tea drin ks, insta nt coffee drinks), meat prod ucts (e.g. ham, fresh sa usage or raw sa usage pre parations, spiced or marinated fresh or sa lt meat products), eggs or egg products (d ried egg, egg white, egg yol k), cerea l prod ucts (e.g. brea kfast cerea ls, muesli bars, precooked ready-to-eat rice products), dai ry prod ucts (e.g. ful l-fat or reduced-fat or fat-free mil k dri nks, rice pudding, yoghu rt, kefi r, crea m cheese, soft cheese, hard cheese, dried mil k pow der, whey, butter, buttermil k, partia lly or com plete ly hydrolysed mil k-protei n-containing products), prod ucts made from soy protein or other soybea n fractions (e.g. soy milk and products prod uced therefrom, drin ks contai ning isolated or enzymatica lly treated soy pro tein, drinks containing soy flou r, prepa rations containing soy lecithin, fermented products such as tofu or tem peh or products produced therefrom and mixtures with fruit prepa ra tions and optiona lly flavou rs), fruit prepa rations (e .g. jams, sorbets, fruit sa uces, fruit fill ings), vegeta ble preparations (e.g. ketchu p, sa uces, dried vegeta bles, frozen vegeta bles, precooked vegeta bles, boiled-down vegeta bles), snacks (e .g. baked or fried potato crisps or potato dough products, maize- or grou nd nut-based extrudates), fat- and oil-based products or emulsions thereof (e.g. mayon naise, remou lade, dressings, in each case ful l-fat or re duced-fat), other ready-made dishes and sou ps (e.g. dried sou ps, insta nt sou ps, precooked sou ps), spices, spice mixtures and in particu la r seasoni ngs which are used, for exa mple, in the snacks field, sweetener pre parations, t ablets or sachets, othe r prepa rations for sw eet ening or whiteni ng drin ks or other foods. The prepa rations within the scope of the invention ca n also be used in the form of semi-fi nished products for the production of further prepa rations for nutrition or enjoyment purposes. The preparations within the scope of the invention ca n also be in the form of ca psu les, t ablets (uncoated and coated t ablets, e.g. enteric coatings), dragees, gra nules, pe llets, solids mixtu res, dispersions in liquid phases, in the form of emulsions, in the form of powders, in the form of solutions, in the form of pastes, or in the form of other prepa rations which ca n be swallowed or chewed, and in the form of food su pplements.

The prepa rations ca n also be in the form of ca psules, t ablets (uncoated and coated t ablets, e.g. enteric coatings), dragees, gra nules, pel lets, solids mixtu res, dispersions in liq uid p has es, in the form of emulsions, in the form of powders, in the form of solutions, in the form of pastes, or in the form of other prepa rations which ca n be swallowed or chewed, for exa m- pie in the form of food supplements.

The semi-fi nished products are genera lly used for the production of ready-to-use or ready- to-eat prepa rations for nutrition or enjoyment purposes.

Fu rther constituents of a ready-to-eat prepa ration or se mi-finished prod uct for nutrition or enjoyment purposes ca n be conventiona l base su bsta nces, auxilia ry su bsta nces and additives for foods or enjoyment foods, for exa mple water, mixtures of fresh or processed, vege table or anima l base or raw su bsta nces (e.g. raw, roast, dried, fermented, smoked and/or boi led meat, bone, ca rtilage, fish, vegeta bles, herbs, nuts, vegeta ble juices, vegeta ble pastes or mixtures thereof), digestible or non-digesti ble ca rbohyd rates (e.g. sucrose, maltose, f ruc tose, glucose, dextrins, amylose, amylopecti n, inulin, xyla ns, cel lulose, tagatose), suga r alcohols (e.g. sorbitol, eryth ritol), natu ral or hardened fats (e.g. t allow, la rd, palm fat, cocoa fat, hardened vegeta ble fat), oils (e.g. su nflower oil, ground nut oil, maize germ oil, olive oil, fish oil, soya oil, sesa me oil), fatty acids or their sa lts (e.g. potassi um stea rate), protei nogenic or non-proteinogenic amino acids and related com pounds (e .g. γ -aminobutyric acid, t aurine), peptides (e.g. glutathione), natura l or processed proteins (e.g. gelati n), enzymes (e.g. pepti- dases), nucleic acids, nucleotides, taste correctors for unpleasa nt taste impressions, f urther taste modu lators for further, genera lly not unpleasa nt taste impressions, other taste- modu lati ng substa nces (e.g. inositol phosphate, nucleotides such as gua nosi ne monophos phate, adenosi ne monophosphate or other substa nces such as sodi um gluta mate or 2- phenoxypropionic acid), emulsifiers (e.g. lecithins, diacylglycerols, gum arabic), sta bilisers (e .g. ca rrageena n, alginate), preservatives (e.g. be nzoic acid and its sa lts, sorbic acid and its sa lts), antioxida nts (e.g. tocopherol, ascorbic acid), chelators (e.g. citric acid), orga nic or in orga nic acidifying agents (e.g. acetic acid, phosphoric acid), additiona l bitter su bsta nces (e.g. qui nine, caffeine, li monene, amarogenti ne, humulone, lupulone, catechols, t annins), sub sta nces that prevent enzymatic browni ng (e.g. sulfite, ascorbic acid), etherea l oils, pla nt extracts, natura l or synthetic colourings or colou ring pigments (e.g. ca roti noids, flavonoids, anthocya ns, chlorophyll and derivatives thereof), spices, trige mina lly active su bsta nces or pla nt extracts contai ning such trigemi nally active su bsta nces, synthetic, natura l or nature- identica l flavou rings or odora nts as wel l as odou r correctors.

Food com positions according t o the invention, for exa mple those in the form of prepa rations or semi-fi nished prod ucts, prefera bly com prise a flavou r com position in order t o co m plete and refi ne the taste and/or odou r. A prepa ration ca n com prise as constituents a solid ca rrier and a flavour com position. Suita ble flavou r com positions com prise, for exa mple, sy n thetic, natu ral or natu re-identica l flavou rings, odora nts and taste-i mparting su bsta nces, reaction flavou rings, smoke flavou rings or other flavour-giving prepa rations (e.g. protei n (pa rtia l) hydrolysates, prefera bly protein (pa rtia l) hydrolysates havi ng a high arginine content, barbecue flavourings, plant extracts, spices, spice preparations, vegetables and/or vegetable preparations) as well as suitable auxiliary substances and carriers. Particularly suitable here are the flavour compositions or constituents thereof which produce a roasted, meaty (in particular chicken, fish, seafood, beef, pork, lamb, mutton, goat), vegetable-like (in particular tomato, onion, garlic, celery, leek, mushroom, aubergine, seaweed), spicy (in particular black and white pepper, cardamom, nutmeg, pimento, mustard and mustard products), fried, yeast-like, boiled, fatty, salty and/or pungent flavour impression and ac cordingly can enhance the spicy impression. The flavour compositions generally comprise more than one of the mentioned ingredients.

The food compositions of the present invention are preferably selected from the group comprising

• confectionery, preferably reduced-calorie or calorie-free confectionery, preferably selected from the group comprising muesli bar products, fruit gums, dragees, hard caramels and chewing gum,

· non-alcoholic drinks, preferably selected from the group comprising green tea, black tea, (green, black) tea drinks enriched with (green, black) tea extracts, rooibos tea, other herbal teas, fruit-containing low-sugar or sugar-free soft drinks, isotonic drinks, nectars, fruit and vegetable juices, fruit and vegetable juice preparations,

• instant drinks, preferably selected from the group comprising instant (green, black, rooibos, herbal) tea drinks,

• cereal products, preferably selected from the group comprising low-sugar and sugar- free breakfast cereals and muesli bars,

• dairy products, preferably selected from the group comprising reduced-fat and fat- free milk drinks, yoghurt, kefir, whey, buttermilk and ice-cream,

· products made from soy protein or other soybean fractions, preferably selected from the group comprising soy milk, products produced from soy milk, drinks containing iso lated or enzymatically treated soy protein, drinks containing soy flour, preparations containing soy lecithin, products produced from preparations containing soy lecithin and mixtures with fruit preparations and optionally flavours,

· sweetener preparations, tablets and sachets,

• sugar-free dragees,

• ice-cream, with or without milk-based constituents, preferably sugar-free.

A. Aroma or flavouring compounds

Aroma compounds and flavouring agents are well known in the art can be added t o the f la vour compositions of the invention. These flavouring agents can be chosen from synthetic flavouring liquid and/or oils derived from plants leaves, flowers, fruits and so forth, and combinations thereof. Representative flavouring liquids include: artificial, natural or sy n thetic fruit flavours such as eucalyptus, lemon, orange, banana, grape, lime, apricot and grapefruit oils and fruit essences including apple, strawberry, cherry, orange, pineapple and so forth; bea n and nut derived flavou rs such as coffee, cocoa, cola, pea nut, almond and so forth; and root derived flavours such as licorice or ginge r.

The flavou ring agent is prefera bly selected from the group consisting of essentia l oils and extracts, t inctures and balsa ms, such as, for exa mple, anisole, basil oil, berga mot oil, bitter almond oil, ca mphor oil, citronel la oil, lemon oil; Euca lyptus citriodora oil, euca lyptus oil, fennel oil, gra pefruit oil, ca momile oil, spea rmi nt oil, ca raway oil, li me oil, manda rin oil, nutmeg oil (in particula r nutmeg blossom oil = maces oil, mace oil), myrrh oil, clove oil, clove blossom oil, ora nge oil, orega no oil, parsley (seed) oil, peppermint oil, rosema ry oil, sage oil (cla ry sage, Da lmatia n or Spa nish sage oil), sta r aniseed oil, thyme oil, vanil la extract, juniper oil (in particu la r j uniper berry oil), wintergreen oil, cin namon leaf oil; cinna mon bark oil, and fractions thereof, or constituents isolated therefrom .

It is of particula r adva ntage if the flavoured com position according t o the invention co m prises at least one flavouring agent, prefera bly two, three, four, five, six, seven, eight or more flavouring agents chosen from the fol lowi ng group : menthol (prefera bly l-menthol and/or racemic menthol), anethole, anisole, anisa ldehyde, anisyl alcohol, (racemic) neomenthol, euca lyptol (1,8-ci neol), menthone (prefera bly L-menthone), isomenthone (prefera bly D-isomenthone), isopulegol, menthyl acetate (prefera bly L-menthyl acetate), menthyl pro pionate, ca rvone (prefera bly (-)-ca rvone, optiona lly as a constituent of a spea rmint oil), m e thyl sa licylate (optiona lly as a constituent of a wintergreen oil), euge nol acetate, isoeugenol methyl ether, beta-homocyclocitra l, eugenol, isobutyra ldehyde, 3-octa nol, dimethyl su lfide, hexa nol, hexa nal, tra ns-2-hexena l, cis-3-hexenol, 4-terpineol, piperitone, li nalool, 8- ocimenyl acetate, isoa myl alcohol, isovalera ldehyde, alpha-pi nene, beta-pi nene, li monene (prefera bly D-li monene, optiona lly as a constituent of an essentia l oil), piperitone, tra ns- sa binene hyd rate, menthofu ran, ca ryophyllene, germacrene D, cinna maldehyde, mint lactone, thymol, gamma-octa lactone, gamma-nona lactone, gamma-deca lactone, (1,3E,5Z)- undecatriene, 2-buta none, ethyl formate, 3-octyl acetate, isoa myl isovalerate, cis- and tra ns-ca rvyl acetate, p-cymol, damascenone, damascone, cis-rose oxide, tra ns-rose oxide, fenchol, aceta ldehyde diethyl aceta l, 1-ethoxyethyl acetate, cis-4-hepte na l, cis-jasmone, methyl dihyd rojasmonate, 2'-hyd roxypropiophenone, menthyl methyl ether, myrtenyl acetate, 2-phe nylethyl alcohol, 2-phenylethyl isobutyrate, 2-phe nylethyl isovalerate, ge raniol, nerol and viridif lorol.

In particu la r preferred aroma or flavouring com pou nds encom pass menthol, cineol, euge nol, thymol, cinna mic aldehyde, peppermi nt oil, spearmint oil, euca lyptus oil, thyme oil, cinna mon oil, clove oil, spruce need le oil, fennel oil, sage oil, aniseed oil, sta r anise oil, cha momi le oil, and ca raway oil, and thei r mixtures.

B. Sweeteners and sweet-tasting substances

The term "sweeteners" here denotes substa nces having a relative sweeteni ng power of at least 25, based on the sweetening power of sucrose (which accordingly has a sweetening power of 1). Sweeteners t o be used in an ora lly consuma ble product (in particu la r foodstuff, feed or medica ment) according t o the invention (a) are prefera bly non-ca riogenic and/or have an ene rgy content of not more tha n 5 kca l per gra m of the ora lly consuma ble prod uct. Adva ntageous sweeteners in a preferred ora lly consu mable product (in particu la r foodstuff, feed or medica ment) accordi ng t o the invention are selected from the fol lowi ng groups (a l ) and (a2) :

(i) naturally occurring sweeteners, prefera bly selected from the group com prisi ng

· miraculin, monellin, mabin li n, tha umatin, curcu li n, brazzein, pentaidi n, D- phenyla la nine, D-tryptopha n, and extracts or fractions obtained from natura l sources, com prisi ng those amino acids and/or proteins, and the physiologica lly accepta ble sa lts of those amino acids and/or protei ns, in particu la r the sodiu m, potassiu m, ca lci um or ammoni um sa lts;

· neohesperidin dihydrocha lcone, naringi n dihyd rocha lcone, stevioside, stevi- olbioside, reba udiosides, in particu la r reba udioside A, reba udioside B, reba udioside C, reba udioside D, reba udioside E, reba udioside F, reba udioside G, reba u dioside H, dulcosides and rubusoside, suavioside A, suavioside B, suavioside G, suavioside H, suavioside I, suavioside J, baiyunoside 1, baiyu noside 2, phlomisoside 1, phlomisoside 2, phlomisoside 3 and phlomisoside 4, abrusoside A, abrusoside B, abrusoside C, abrusoside D, cycloca ryoside A and cycloca ryoside I, osladin, polypodoside A, strogin 1, strogin 2, strogin 4, selligueai n A, dihy-

droq uercetin 3-acetate, perilla rti n, telosmoside A 5, peria nd rin l-V, pteroca ryosides, cycloca ryosides, mukuroziocides, tra ns-a nethole, tra ns-cin namaldehyde, bryosides, bryonosides, bryonod ulcosides, ca rnosiflosides, sca ndenosides, gype- nosides, tri lobati n, phloridzin, dihydroflava nols, hematoxyli n, cya nin, chlorogenic acid, albiziasa poni n, telosmosides, gaudicha udioside, mogrosides, mogroside V, he rna ndu lci ns, monati n, phyl lodu lci n, glycyrrheti nic acid and derivatives thereof, in particu la r glycosides thereof such as glycyrrhizine, and the physiologica lly accepta ble sa lts of those com pou nds, in particu la r the sodiu m, potassi um, ca lci um or ammoni um sa lts;

• extracts or conce ntrated fractions of the extracts, se lected from the grou p co m prising tha umatococcus extracts (kata mfe pla nt), extracts from Stevia ssp. (in particu la r Stevia rebaudiana), swingle extracts (Momordica or Siratia grosvenorii, Luo-Ha n-G uo), extracts from Glycyrrhiza ssp. (in particu la r Glycyrrhiza glabra), extracts from Rubus ssp. (in particula r Rubus suavissimus), citrus extracts and ex tracts from Lippia dulcis;

(ii) synthetic sweet-tasting substances, prefera bly selected from the grou p com prising maga p, sodi um cycla mate or other physiologica lly accepta ble sa lts of cycla mic acid, acesul- fame K or other physiologica lly accepta ble sa lts of acesulfa me, neohesperidin dihyd rocha l cone, naringi n dihydrocha lcone, saccha rin, saccha rin sodi um sa lt, aspa rta me, superaspa r- tame, neota me, alita me, adva nta me, peril la rtin, sucra lose, lugdu name, ca rre la me, sucrononate and sucrooctate.

Suita ble sweet-tasting su bsta nces, includi ng natura l sources of these su bsta nces such as for exa mple

• sweet-tasting ca rbohydrates or suga rs (e.g. sucrose (synonymous with saccha rose), treha lose, lactose, maltose, melizitose, raffinose, palati nose, lactulose, D-fructose, D- glucose, D-ga lactose, L-rha mnose, D-sorbose, D-ma nnose, D-tagatose, D-a rabinose, L- ara binose, D-ri bose, D-glycera ldehyde, maltodextrin) or vegeta ble prepa rations contai ning predomi nantly these ca rbohydrates (e.g. from sug ar beet (Beta vulga ris ssp., suga r fractions, suga r syru p, molasses), from suga r ca ne (Saccha rum officina rum ssp., e.g. molasses, suga r syrups), from suga r maple (Acer ssp.), from agave (agave thick juice),

synthetic/enzymatic hydrolysates of sta rch or sucrose (e.g. invert suga r syru p, highly enriched fructose syrups made from corn sta rch),

fruit concentrates (e.g. from apples or pea rs, apple syru p, pea r syru p),

suga r alcohols (e.g. erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, dulci- tol, lactitol),

proteins (e.g. miraculin, monellin, tha umatin, curculin, brazzein),

artificia l sweeteners (maga p, sodi umcycla mate, acesu lfa me K, neohesperidi n dihyd rocha lcone, saccha rin sodiu m sa lt, aspa rta me®, su peraspa rta me, neota me, alita me, sucra lose, lugdu name, ca rre la me, sucrononate, sucrooctate, monatin),

certai n sweet-tasting amino acids (glycine, D-leucine, D-th reoni ne, D-aspa ragine, D- phenyla la nine, D-tryptopha n, L-proli ne),

other sweet-tasting low-molecu la r substa nces, e.g. reba udioside, stevioside, mogrosides, herna nd ulcin, phyl lodu lci n, dihyd rocha lcone glycosides, glycyrrhizin, glycyrrheti nic acid ammoni um sa lt or other glycyrrhetinic acid derivatives,

extracts from sweet tasti ng pla nts, in particu la r Momordica grosvenori [Luo Ha n Guo] Hydra ngea macrophyl la, Stevia ssp. (e.g. Stevia reba udia na), Rubus suavissim us, Poly- podiu m vulga re, Abrus precatori us, Pteroca rya pali urus, Baccharis gaudicha udia na, Al- bizia myriophyl la, Bryonia dioica, Phlomis betonicoides, Hemsleya ca rnosiflora, Li ppia dulcis, Gynostem ma penta phyl lum, Glycyrrhiza gla bra (liq uorice) or individ ual sweet tasting su bsta nces isolated from those pla nts.

Thickeners

Adva ntageous thickeners in a preferred ora lly consu mable prod uct (in particula r foodstuff, feed or medica ment) accordi ng t o the invention are se lected from the group com prisi ng: crosslin ked polyacrylic acids and derivatives thereof, polysaccha rides and derivatives thereof, such as xantha n gum, aga r-aga r, algi nates or tyloses, ce llu lose derivatives, for exa mple ca rboxymethylce llu lose or hyd roxyca rboxymethylcell ulose, fatty alcohols, monoglycerides and fatty acids, polyvi nyl alcohol and polyvinyl pyrrolidone.

Preference is given according t o the invention t o an ora lly consu mable prod uct (in particula r foodstuff or feed) which com prises mil k thickened with lactic acid bacteria and/or crea m thickened with lactic acid bacteria and which prefe rably is selected from the group com pris ing yoghu rt, kefi r and q uark.

A food com position accordi ng t o the invention com prisi ng mil k thickened with lactic acid bacteria and/or crea m thickened with lactic acid bacteria is adva ntageously an ora lly co n suma ble product which com prises a probiotic, wherei n the probiotic is prefera bly selected from the group com prising Bifidobacteri um animalis su bsp. lactis BB-12, Bifidobacteri um anima lis su bsp. lactis DN-173 010, Bifidobacteri um anima lis subsp. lactis HN019, Lactobacil- lus acidophi lus LA5, Lactobacil lus acidophil us NCFM, Lactobacil lus joh nsonii La i , Lact obacil lus casei immunitass/defensis, Lactobaci llus casei Shi rota (DSM 20312), Lactobacil lus casei CRL43 1, Lactobaci llus reuteri (ATCC 55730) and Lactobaci llus rha mnosus (ATCC 53013).

D. Additives for chewing gums

Pa rticula r preference is given t o an ora lly consuma ble product (in particu la r foodstuff, feed or medica ment) accordi ng t o the invention that is a chewing gum and com prises a chewi ng- gum base. The chewi ng-gum base is prefera bly selected from the grou p com prisi ng chew ing-gum o r bubble-gum bases. The latter are softer, so that gum bubbles ca n also be formed therewith. Preferred chewi ng-gum bases according t o the invention include, in addition t o the natu ral resins o r the natu ral latex chicle that are traditiona lly used, elastomers such as polyvinyl acetate (PVA), polyethylene, (low o r medi um molecula r weight) polyisobutene (PIB), polybutadiene, isobutene-isoprene copolymers (butyl rubber), polyvi nyethyl ether (PVE), polyvinyl butyl ether, copolymers of vinyl esters and vinyl ethers, styrene-butadiene copolymers (styrene-butadiene rubber, SBR) o r vinyl elastomers, for exa mple based o n vinyl acetate/vinyl la urate, vinyl acetate/vinyl stea rate or ethylene/vi nyl acetate, as w ell as m ix tures of the mentioned elastomers, as described, for exa mple, in EP 0 242 325, US 4,518,615, US 5,093, 136, US 5,266,336, US 5,601,858 o r US 6,986,709. In addition, chewi ng- gum bases that are prefera bly t o be used according t o the invention prefera bly com prise further constituents such as, for exa mple, (mi nera l) fil lers, plasticisers, emulsifiers, ant ioxi dants, waxes, fats or fatty oils, such as, for exa mple, hardened (hydrogenated) vegeta ble o r anima l fats, mono-, di- or tri-glycerides. Suita ble (minera l) fil lers are, for exa mple, ca lci um ca rbonate, tita nium dioxide, si licon dioxide, t alcu m, aluminiu m oxide, dica lciu m phosphate, trica lciu m phosphate, magnesiu m hydroxide and mixtu res thereof. Suita ble plasticisers, o r agents for preventing adhesion (detackifiers), are, for exa mple, la nolin, stea ric acid, sodi um stea rate, ethyl acetate, diacetin (glycerol diacetate), triacetin (glycerol triacetate), triethyl citrate . Suita ble waxes are, for exa mple, paraffi n waxes, ca nde lil la wax, ca rna uba wax, microcrysta lline waxes and polyethylene waxes. Suita ble emulsifiers are, for exa mple, phos phatides such as lecithi n, mono- and di-glycerides of fatty acids, for exa mple glycerol monostea rate.

Chewing gums accordi ng t o the invention (in particula r as disclosed above) prefera bly co m prise constituents such as suga rs of different types, suga r substitutes, other sweet-tasting substa nces, suga r alcohols (in particula r sorbitol, xylitol, mannitol), ingredients having a cooling effect, taste correctors for unpleasa nt taste impressions, f urther taste-mod ulating substa nces (e.g. inositol phosphate, nucleotides such as gua nosi ne monophosphate, adeno sine monophosphate o r other su bsta nces such as sodi um gluta mate or 2-phenoxypropionic acid), humecta nts, thickeners, emulsifiers, sta bilise rs, odou r correctors and flavours (e.g. euca lyptus-menthol, cherry, strawberry, gra pefruit, vanil la, banana, citrus, peach, blackcur rant, tropica l fruits, ginger, coffee, cinna mon, com binations (of the mentioned flavours) with mint flavours as wel l as spea rmi nt and peppermint o n thei r own). The com bination inter alia of the flavours with f urther su bsta nces that have cooli ng, w armi ng and/or mo ut h watering properties is of particula r interest. E. Vitamins

In another embodiment of the present invention the com positions may incl ude vita mins (com ponent el). Vita mins have diverse biochemica l functions. Some have hormone-li ke functions as regu lators of minera l meta bolism (e.g., vita min D), or regulators of cell and tis- sue growth and differentiation (e.g., some forms of vita min A). Others function as ant ioxi dants (e.g., vita min Eand sometimes vita min C). The la rgest number of vita mins (e.g. B com plex vita mins) act as precursors for enzyme cofactors, that help enzymes in their work as cata lysts in meta bolism . In this role, vita mins may be tightly bou nd t o enzymes as part of prosthetic groups: For exa mple, biotin is part of enzymes involved in making fatty acids. Vita mins may also be less tightly bou nd t o enzyme cata lysts as coenzymes, detacha ble mo l ecules that function t o ca rry chemica l grou ps or electrons between molecu les. For exa m ple, folic acid ca rries various forms of ca rbon group - methyl, formyl, and methylene - in the cell. Although these roles in assisti ng enzyme-substrate reactions are vita mins' best-known function, the other vita min f unctions are equa lly importa nt. In the cou rse of the present invention suita ble vita mins are selected from the group consisting of

• Vita min A (retinol, reti nal, beta ca rotene),

• Vita min B (thia mine),

• Vita min B2 (riboflavin),

• Vita min B3 (niaci n, niaci namide),

· Vita min B5 (pa nthothenic acid), • Vita min B (pyridoxine, pyridoxa mine, paridoxa l),

• Vita min B7 (biotin),

• Vita min B9 (folic acid, foli nic acid),

• Vita min Bi 2 (cya noba la min, hydoxycoba lmi n, methylcoba lmi n), · Vita min C (ascorbic acid),

• Vita min D (choleca lciferol),

• Vita min E (tocopherols, tocotrienols), and

• Vita min K (phyol loquinone, menaq uinone).

The prefe rred vita mins are ascorbic acid and tocopherols.

Said vita mins may be present in the food com position in amou nts of about 0.1 t o about 5 % b.w., and prefera bly about 0.5 t o about 1 % b.w. ORAL COMPOSITIONS

Typica l exa mples for non-food ora l com positions encom pass prod ucts for clea ning and pro tecting teeth and refreshi ng the ora l cavity.

The ora l com positions of the present invention typica lly com prise an abrasive system (a bra- sive or polishing agent), such as e.g. silicas, ca lciu m ca rbonates, ca lciu m phosphates, alumin ium oxides and/or hydroxya patites, su rface-active su bsta nces, such as e.g. sodiu m la uryl sulfate, sodi um la uryl sa rcosinate and/or coca midopropyl betaine, moisture-retaining agents, such as e.g. glycerol and/or sorbitol, thickening agents, such as e.g. ca rboxymethyl- cellu lose, polyethylene glycols, ca rrageena n and/or La ponite , sweeteners, such as e.g. saccha rin, flavou r correcta nts for unpleasa nt taste impressions, flavour correcta nts for further, as a rule not unpleasa nt taste impressions, flavour-modu lati ng su bsta nces (e.g. inositol phosphate, nucleotides, such as gua nosine monophosphate, ade nosine monophosphate o r other substa nces, such as sodi um gluta mate or 2-phenoxypropionic acid), cooling active com pounds, such as e.g. menthol derivatives (e.g. L-menthyl lactate, L-menthyl alkyl ca r- bonates, menthone keta ls, mentha neca rboxylic acid amides), 2,2,2-tria lkylacetic acid amides (e .g. 2,2-diisopropylpropionic acid methyla mide), icilin and ici li n derivatives, sta bilizers and active com pounds, such as e.g. sodi um fluoride, sodiu m monofluorophosphate, tin difl uo- ride, quaterna ry ammoni um f luorides, zinc citrate, zinc su lfate, t in pyrophosphate, tin di- chloride, mixtu res of various pyrophosphates, triclosa n, chlorhexidi ne, cetyl pyridi nium chloride, alumi nium lactate, potassi um citrate, potassi um nitrate, potassiu m chloride, stronti um chloride, hyd rogen peroxide, aromas, sodi um bica rbonate and/or odour correcta nts.

Form ulations or products accordi ng t o the invention in the form of chewi ng gums or, in pa r ticula r, denta l ca re chewi ng gums com prise chewing gum bases which com prise elastomers, such as, for exa mple, polyvinyl acetates (PVA), polyethylenes, (low o r mediu m molecula r weight) polyisobutenes (PI B), polybutadienes, isobute ne-isoprene copolymers (butyl rub ber), polyvinyl ethyl ethers (PVE), polyvinyl butyl ethe rs, copolymers of vinyl esters and vinyl ethers, styrene/butadie ne copolymers (styrene/butadiene rubber, SBR) or vinyl elastomers, e.g. based o n vinyl acetate/ vinyl la urate, vinyl acetate/vi nyl stea rate o r ethylene/vinyl ace tate, and mixtures of the elastomers mentioned, as described, for exa mple, in EP 0 242 325, US 4,5 18,615, US 5,093,136, US 5,266,336 US 5,601,858 or US 6,986,709. In addition, chew ing gum bases com prise further constituents, such as, for exa mple, suga rs, suga r substitutes or sweet-tasing su bsta nces in particu la r those described in W O 2009/21558, (mi nera l) fill ers, plasticizers, emulsifiers, antioxida nts, waxes, fats or fatty oils, such as, for exa mple, hardened (hydrogenated) pla nt o r anima l fats, and mono-, di- o r triglycerides. Suita ble (mi nera l) fillers are, for exa mple, ca lciu m ca rbonate, tita nium dioxide, si licon dioxide, t alc, alumi nium oxide, dica lci um phosphate, trica lci um phosphate, magnesi um hydroxide and mixtu res thereof. Suita ble plasticizers o r agents for preventing sticki ng (detackifiers) are, for exa mple, la noli n, stea ric acid, sodi um stea rate, ethyl acetate, diacetin (glycerol diacetate), triacetin (glycerol triacetate) and triethyl citrate. Suita ble waxes are, for exa mple, paraffi n waxes, ca ndeli lla wax, ca rna uba wax, microcrysta lline waxes and polyethylene waxes. Suit a ble emulsifiers are, for exa mple, phosphatides, such as lecithi n, and mono- and diglycerides of fatty acids, e.g. glycerol monostea rate.

Form ulations o r products according t o the invention (in particu la r those which are in the form of an ora l ca re form ulation o r product or in the form of a form ulation) prefera bly additiona lly com prise one o r more aroma and/or flavouri ng substa nces, such as essentia l oils and extracts, tinctu res and balsa ms, such as, for exa mple, anisole, basi l oil, berga mot oil, bitter almond oil, ca mphor oil, citronella oil, lemon oil; Euca lyptus citriodora oil, euca lyptus oil, fen nel oil, gra pefruit oil, ca momile oil, spea rmint oil, ca raway oil, li me oil, manda rin oil, nutmeg oil (in particula r nutmeg blossom oil = maces oil, mace oil), myrrh oil, clove oil, clove blossom oil, ora nge oil, orega no oil, parsley (seed) oil, peppermint oil, rosema ry oil, sage oil (cla ry sage, Da lmatia n or Spa nish sage oil), sta r aniseed oil, thyme oil, vanil la extract, juniper oil (in particu la r j uniper berry oil), wintergreen oil, cin namon leaf oil; cinna mon bark oil, and fractions thereof, or constituents isolated therefrom .

It is of particula r adva ntage if said form ulations or products com prise at least one aroma substa nce, prefera bly 2, 3, 4, 5, 6, 7, 8, 9, 10 or more aroma substa nces, chosen from the fol lowi ng grou p: menthol (prefera bly l-menthol and/or racemic menthol), anethole, anisole, anisa ldehyde, anisyl alcohol, (racemic) neomenthol, eucalyptol (1,8-cineol), menthone (prefera bly L-menthone), isomenthone (prefera bly D-isomenthone), isopulegol, menthyl acetate (prefera bly L-menthyl acetate), menthyl propionate, ca rvone (prefera bly (-)- ca rvone, optiona lly as a constituent of a spea rmint oil), methyl sa licylate (optiona lly as a constituent of a wintergreen oil), eugenol acetate, isoeugenol methyl ether, beta- homocyclocitra l, eugenol, isobutyra ldehyde, 3-octa nol, dimethyl sulfide, hexa nol, hexa nal, tra ns-2-hexena l, cis-3-hexenol, 4-terpi neol, piperitone, li nalool, 8-oci menyl acetate, isoa myl alcohol, isovalera ldehyde, alpha-pinene, beta-pinene, limonene (prefera bly D-limonene, optiona lly as a constituent of an essentia l oil), piperitone, tra ns-sa binene hydrate, mentho- fura n, ca ryophyllene, germacrene D, cin namaldehyde, mint lactone, thymol, gamma- octa lactone, gamma-nona lactone, gamma-deca lactone, (l,3E,5Z)-u ndecatriene, 2- buta none, ethyl formate, 3-octyl acetate, isoa myl isovalerate, cis- and tra ns-ca rvyl acetate, p-cymol, damascenone, damascone, cis-rose oxide, trans-rose oxide, fenchol, aceta ldehyde diethyl aceta l, 1-ethoxyethyl acetate, cis-4-heptena l, cis-jasmone, methyl dihydrojasmonate, 2'-hydroxypropiophenone, menthyl methyl ether, myrte nyl acetate, 2-phenylethyl alcohol, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, gera niol, ne rol and viridiflorol .

PHARMACEUTICAL COMPOSITIONS

Pha rmaceutica l com positions according t o the present invention may incl ude simi la r addi tives as already explai ned for the food and ora l com positions, such as aroma and flavors. Pha rmaceutica l com positions may further incl ude, oil bodies or emulsifiers and in particula r co-actives su pporting the beneficia l properties of the pha rmaceutica l active agent. There fore, the border between food com positions and pha rmaceutica l com positions is in flow and it shou ld be understood that com ponents cited for one application are recom mended for the other mutatis-mutandis without litera l repetition .

Fu rther subject of the present invention is the use of a sweete ner com pound of form ula (I) or a pre paration com prisi ng at least one sweetener com pou nd of form ula (I) t o sweet or enha nce the sweeting effect in com positions, such as ora l or food or pha rmaceutica l compositions, and that are admi nistered t o an individ ual . Prefe rably, one or more of the co m pou nd of form ula (I) is used in an amou nt from 1 ppm t o 2000 ppm by weight, based on the tota l weight of the com position and base on the tota l sum of all com pounds of form ula (I), if more than one com pou nd of form ula (I) is used . More prefera bly, the sweetener co m pou nds of form ula ( I) are used in an amou nt from 10 ppm t o 1000 ppm by weight, most prefera bly in an amou nt of 20 ppm t o 500 ppm by weight, based on the tota l weight of the com position and base on the tota l sum of all com pou nds of form ula ( I), if more tha n one com pound of form ula ( I) is used.

In another preferred embodi ment the sweetener com pounds of form ula ( I) or a prepa ration com prising at least one sweetener com pound of form ula (I) is used to synergistica lly enhance a sweet taste of a sweet-tasti ng substa nce in a com position. The preferred co m pou nds of form ula ( I) are prefera bly selected from the group consisting of:

• Compound A

3, ll-dihydroxy-4,4,9,13, 14-penta methyl-2,3,4,7,8,9,10, ll,12, 13,14, 15,16, 17- tetradeca hydro-lH-cyclopenta [a] phena nthren-17-yl)-2-hydroxy-2-methylhepta n-3- yloxy)-4,5-dihyd roxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-3-yloxy)-6- (hydroxymethyl)tetra hydro-2H-pyra n-3,4,5-triol;

• Compound B 4,5-dihyd roxy-2-(2-hyd roxy-2-methyl-6-((4A9,13, 14-penta methyl-3-(3A5-trihyd roxy- 6-((3,4,5-tri hydroxy-6-(hyd roxymethyl)tetra hydro-2H-pyran-2- yloxy)methyl)tetra hydro-2H-pyra n-2-yloxy)-2,3,4,7,8,9, 10,ll, 12,13, 14,15, 16,17- tetradeca hydro-lH-cyclopenta [a] phena nthren-17-yl)hepta n-3-yloxy)-6-((3,4,5- trihyd roxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)methyl)tetra hydro-2H- pyran-3-yloxy)-6-(hydroxymethyl)tetra hyd ro-2H-pyra n-3,4,5-triol;

• Compound C 4,5-dihyd roxy-3-(3,4,5-trihyd roxy-6-(hyd roxymethyl)tetra hyd ro-2H-pyra n-2-yloxy)-6- ((3,4,5-tri hydroxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)methyl)tetra hydro- 2H-pyran-2-yloxy)-6-hydroxy-6-methylhepta n-2-yl)-4,4,9,13, 14-penta methyl- 2,3,4,7,8,9, 10,ll, 12,13, 14,15, 16,17-tetradeca hydro-lH-cyclopenta [a] phena nthren-3- yloxy)-4,5-dihyd roxy-2-(hyd roxymethyl)tetra hydro-2H-pyra n-3-yloxy)-6- (hydroxymethyl)tetra hydro-2H-pyra n-3,4,5-triol;

• Compound D

2-(2-(17-(5-(4,5-di hydroxy-3-(3,4,5-tri hydroxy-6-(hydroxymethyl)tetra hydro-2H-pyra n- 2-yloxy)-6-((3,4,5-trihyd roxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2- yloxy)methyl)tetra hydro-2H-pyra n-2-yloxy)-6-hyd roxy-6-methylhepta n-2-yl)- 4,4,9, 13,14-penta methyl-2,3,4,7,8,9, 10,ll, 12,13, 14,15, 16,17-tetradeca hydro-lH- cyclopenta [a] phena nthren-3-yloxy)-4,5-di hydroxy-6-(hydroxymethyl)tetrahyd ro-2H- pyran-3-yloxy)-6-(hydroxymethyl)tetra hyd ro-2H-pyra n-3,4,5-triol;

• Compound E 2-(4,5-dihyd roxy-2-(2-hyd roxy-2-methyl-6-(4,4,9,13, 14-penta methyl-3-(3,4,5- trihyd roxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2-yloxy)- 2,3,4,7,8,9, 10,ll, 12,13, 14,15, 16,17-tetradeca hydro-lH-cyclopenta [a] phena nthren-17- yl)hepta n-3-yloxy)-6-((3,4,5-trihyd roxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2- yloxy)methyl)tetra hydro-2H-pyra n-3-yloxy)-6-(hyd roxymethyl)tetra hyd ro-2H-pyra n- 3,4,5-triol; Compound F 2-((6-(6-(3-(4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxytetrahydro-2H-pyran- 2-yloxy)tetrahydro-2H-pyran-2-yloxy)-ll-hydroxy-4,4,9,13,14-pentamethyl- 2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-17 yl)-2-hydroxy-2-methylheptan-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-(3-hydroxy-2-methyl-6-(4,4,9,13,14-pentamethyl-3-(3,4,5- trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)- 2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-17 yl)heptan-2-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;

Compound H 2-hydroxy-6-(ll-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,ll,12,13,14,15,16,17-tetradecahydro-lH- cyclopenta[a]phenanthren-17-yl)-2-methylheptan-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)-ll- hydroxy-4,4,9,13,14-pentamethyl-4,7,8,9,10,ll,12,13,14,15,16,17-dodecahydro-lH- cyclopenta[a]phenanthren-3(2H)-one;

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,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-17 yl)-2-methylheptan-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 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-lH-cyclopenta[a]phenanthren- ll(2H)-one;

Compound M 2-(4,5-dihydroxy-2-(2-hydroxy-2-methyl-6-(4,4,9,13,14-pentamethyl-3-(3,4,5- trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)- 2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH-cyclopenta[a]phenanthren-17 yl)hepta n-3-yloxy)-6-((3,4,5-trihyd roxy-6-(hyd roxymethyl)tetra hydro-2H-pyra n-2- yloxy)methyl)tetra hydro-2H-pyra n-3-yloxy)-6-(hyd roxymethyl)tetra hyd ro-2H-pyra n- 3,4,5-triol; whe rei n the isomeric forms (Aa) t o (M m) which have bee n specified are most preferred.

Fu rther su bject of the invention is an extract containi ng one or more of a com pound of formula I)

(I) whe rei n R1 R2, R3 are independently of one another and denote hydrogen, hydroxyl, car bonyl or a suga r moiety selected from a monosaccha ride and/or oligosaccha ride, whe rei n the extract is obtaina ble by the method of aqueous and / or alcoholic extraction of pla nt materia ls selected from the grou p consisti ng of Momordica grosvenorii (Siraitia grosvenori).

In this context " pla nt materia ls" refers t o parts of the respective pla nt of Momordica grosvenorii (Siraitia grosvenori). The pla nt materia ls may incl ude parts of the whole pla nt selected from the group consisting of blossoms, fruits, buds, roots, seeds and/or leaves or the whole pla nt itself.

The extract com prises at least one com pound of form ula (I) selected from the group co nsist ing of com pou nd A, B, C, D, E, F, G, H, J, K, L, M or mixtures thereof, whe rei n the isomeric forms (Aa) t o (M m) which have bee n specified are most preferred.

More prefera bly, the extract com prises at least two, three, fou r, five, six, seven, eight, nine, ten or eleven com pounds of form ula (I). Prefera bly, the extract com prises all com pou nds I t o X II of form ula ( I), especia lly the all isomeric forms (Aa) t o (M m) which have been speci fied .

EXTRACTION

The extracts accordi ng t o the present invention may be pre pared by methods known per se, i.e. for exa mple by aqueous, alcoholic or aqueous/a lcoholic extraction of the pla nts or parts thereof or shel ls of the litchi fruits. Suita ble extraction processes are any conventiona l ex traction processes, such as maceration, re-maceration, digestion, agitation maceration, vor tex extraction, ultrasonic extraction, counter current extraction, percolation, re percolation, evacolation (extraction under reduced pressure), diacolation and solid/liq uid extraction under contin uous refl ux. Percolation is adva ntageous for industria l use. Litchi shells are preferably used as the sta rting materia l and may be mecha nica lly size-reduced before the ext rac tion process. Any size red uction methods known t o the expert, for exa mple freeze gri nding, may be used. Preferred solvents for the extraction process are orga nic solvents, water (prefera bly hot water with a tem perature above 80 °C and more particula rly above 95 °C or mixtu res of orga nic solvents and water, more particula rly low molecu la r weight alcohols with more or less high water contents. Extraction with metha nol, etha nol, isopropa nol and water-containing mixtu res thereof is particu la rly preferred . The extraction process is gener ally ca rried out at about 20 t o about 100 °C and prefera bly at about 50 t o about 70 °C. In one preferred embodi ment, the extraction process is ca rried out in an inert gas atmosphere t o avoid oxidation of the ingredients of the extract. This is particu la rly importa nt where ex traction is ca rried out at tem peratu res above 40 °C. The extraction times are selected by the expe rt in dependence upon the sta rting materia l, the extraction process, the extraction tem perature and the ratio of solvent t o raw materia l, etc. Afte r the extraction process, the crude extracts obtai ned may optiona lly be su bjected t o other typica l steps, such as for ex- am ple purification, concentration and/or decoloration. If desired, the extracts thus pre pared may be su bjected, for exa mple, t o the selective remova l of individua l unwa nted in gredients. The extraction process may be ca rried out t o any degree, but is usua lly conti nued t o exha ustion. Typica l yields (=extract dry matter, based on the qua ntity of raw materia l used) in the extraction of the sta rti ng materia ls are of the order of about 1 t o about 20, %, prefera bly about 2 t o about 15 and more prefera bly about 5 t o about 10 % b.w. - ca lculated on the sta rting materia ls.

The content in the extract of each of the com pounds (A) t o (M ) differs from batch t o batch depe ndi ng on the used raw materia l of fruits of M . grosvenori. Usua lly the major triterpene glycoside in extracts of M . grosvenori is Mogroside V (CAS 88901-36-4) with a relative amount of 50 t o 90% of the tota l amou nt of triterpe ne glycosides. Com pou nds (A) t o (M ) usua lly represent between 0.01 t o 5% of tota l amou nt of triterpene glycosides in M . grosvenori.

Fu rther, the invention relates t o a method for providing a sweetening effect and/or an e n hanced sweete ning effect in com positions, such as food or ora l or pha rmaceutica l com positions, com prisi ng admi nistering t o an individ ual at least a sweetener com pou nd of form ula (I) or a prepa ration com prising at least one com pound of form ula ( I) or an extract com pris ing at least one com pou nd of form ula (I).

Preferred food com positions are e.g. confectionery, such as chocolate, chewi ng gums, hard ca ramels, and milk base prod ucts, such as yoghu rt, butterm ilk, cheese, ice crea ms, and beverages, such as non-a lcoholic d rinks, refreshing drin ks, fruit-contai ning d rinks, and baked goods, and meat products, such as sa usages, and cerea l prod ucts, such as muesli, brea kfast cerea ls, and fruit prepa rations, such as jams, sorbets, fruit sa uces and "semi-fi nished prod ucts" . This list of possi ble application is not restricted t o the mentioned application, but is only illustrative. The sweetener com pou nds of form ula (I) ca n be provided in every prod uct t o provide a kind of sweetness.

Fu rther, the invention relates t o a method of usi ng a sweetener com pound of form ula ( I) t o synergistica lly enhance a sweet taste of a sweet-tasti ng substa nce.

The invention, also prefera bly relates t o a method of imparting or enhancing the sweetness of ora l and com position which com prises adding thereto one or more com pounds of form u- la ( I) in an amou nt of from about 1 ppm t o about 2000 ppm . INDUSTRIAL APPLICATION

More particu la rly, the present invention also refers t o an ora l edi ble com position, com pris in an edible su bsta nce and at least one com pou nd of form ula (I)

The effective amount is prefera bly from 1 ppm t o 2000 ppm (basis edible su bsta nce), more prefera bly from 10 ppm by weight t o 1000 ppm by weight, most prefe rred from 20 ppm by weight t o 500 ppm by weight, based on the tota l weight of the com position and the tota l sum of all com pou nds of form ula ( I).

Preferred edible com positions are the preferred food com positions which have been described herein.

Fu rther, the com pounds of form ula (I) are suita ble as sweetener in lia ble com positions.

The invention w ill be further descri bed by the following Exa mples. These Exa mples are pro vided t o illustrate the invention and are not t o be construed as li miti ng the scope of the invention .

Fu rther, the invention refers t o a prepa ration, com prisi ng one, two, t hree or more of a sweetener com pound of form ula ( I), wherein the prepa ration optiona lly f urther com prises aroma com pou nds and/or flavouring agents and/or sweeteners and/or sweet-tasting sub sta nces.

The prepa ration is prefera bly an ora l edible com position . EXAMPLES

The exa mples which fol low are intended t o illustrate the present invention without limiting the invention. Unless indicated otherwise all amou nts, parts and percentages are based o n the weight and the tota l amount or o n the tota l weight and the tota l amou nt of the prepa rations.

Example 1 Extraction and identification of com pou nds of form ula ( I)

A) Extraction

2kg d ried fruits of Momordica grosvenori (Syn . Siraitia grosvenori), provided by Cfm Oska r Tropitzsch, M arktredwitz, Ge rma ny, were extracted with 181 metha nol-MTB-ether at room tem perature for 24h (yield : 275g extract). 1kg dried fruits of Momordica grosvenori (Syn . Siraitia grosvenori), provided by DAXI NGAN LING SN OW LOTUS HERB B IO-TECH NOLOGY CO., LTD., Chi na, were extracted with 101 metha nol at room tem pe ratu re for 24h (yield : 310g extract).

B) Enrichment

In order t o remove very pola r suga rs the raw extract were dissolved in 5 1 water-metha nol (9 :1) and 500m l of absorber resin HP-20 was added . The filtered resin was washed with w a ter t o elute the pola r ingredients which are not w anted. El ution with metha nol yielded 37g of a mixtu re of triterpene-glycosides.

C) Pre-fractionation by normal phase chromatography

The resulted fraction of B) was then sepa rated by medium pressure chromatogra phy under the fol lowi ng conditions:

• stationary phase: Silica 60 (Merck)

• mobi le phase solvent A : CHCI 3 - metha nol - water 1680 : 720 : 120

• mobi le phase solvent: B CHCI 3 - metha nol - water 1350 : 900 : 225 · gradie nt: 100% A t o 50% A in 40 min, 10 min 50% A , 10 min 90% metha nol - 10% w a ter

• colu mn dimension : 50 x 250 mm

Seven fractions were col lected and evaporated as set out in the following Table C : Table C Fractions

D) Pre-fractionation by reverse phase chromatography

300g raw extract of M . grosvenori were sepa rated by reverse phase medi um pressure chro matogra phy under the fol lowi ng conditions:

Conditions of the sepa ration of enriched triterpen glycoside fraction :

· stationa ry phase : RP-18, 40-63 µ (Merck)

• mobi le phase solvent A : water

• mobi le phase solvent B: metha nol

• colu mn dimension : 50 x 250 mm

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

Table C Fractions E) Final purification by reverse phase chromatrography

Pure com pou nds were isolated by reverse phase chromatogra phy usi ng enriched fractions generated by pre-fractionation steps described in step D).

Table 1 Conditions of the separation of C-1780-C Table 3 Conditions of the separation of C-1780-E

Table 4 Conditions of the separation of C-1780-F

Table 5 Conditions of the separation of H-1949-G Table 6 Conditions of the separation of C-1750-N F) Analytical characterisation of isolated triterpene- glycosides

Fractions from preparative HPLC were collected (40ml each) and analysed by HPLC-MS. Frac tions containing the same compound according t o retention time and mass spectrum were combined, evaporated and analysed by HPLC-MS and NMR (1H-NMR. HH-COSY. HSQC. HMBC). Structures were elucidated by interpretation of NMR and M S data.

Table 9 Conditions of the HPLC-MS of isolated compounds G) Identification: analytical characterisation of the compounds

The isolated compounds of formula (I) are characterised through mass spectroscopy and NMR spectroscopy, see fig 1 to 24. The compounds were identified as:

Compound Aa ompound Cc

Compound Ee ompound Ff

Compound Gg Compound Jj

Compound Kk

Compound LI Compound Mm Example 2 Orga noleptic test of the com pou nds of form ula ( I) against sucrose and mogroside V

The isolated pure com pounds were dissolved in non-carbonated minera l water („ Fonsa na Que lle") in a concentration of 0.4 mg/m l (400 ppm). The sweet taste of each sa mple was com pared by a panel of 4 panelists with a sol ution of sucrose in a concentration of 20 mg/m l and with a sol ution of the known sweetener mogroside V (isolated by Ana lytiCon from Momordica grosvenori) in a concentration of 0.1 mg/m l (100 ppm).

The sweetness was evaluated as follows:

3 = sweeter tha n the control sol ution

2 = sweetness com parable with the control solution

1 = less sweet tha n the control solution but stil l sweet

Table 10 Organoleptic evaluation Example 3 Formulation examples

The following Tables 11 to 14 provide some examples for oral compositions comprising at least one of the sweeteners disclosed before.

Table 11 Chewing gum, free of sugar; all amounts in % b.w. Table 12 Tooth paste; all amounts in % b.w. Table 14 Hard boiled candy, sugar-free; all amounts in % b.w. WHAT CLAIMED IS

1. A sweetener com pou nd of form ula ( I)

(I)

whe rei n R1 R2, R3 are independently of one another and denote hyd rogen, hydroxyl, carbonyl or a suga r moiety selected from the grou p consisti ng of a monosaccha ride and/or an oligosaccha ride,

whe rei n the monosaccha ride and/or the monosaccha ride units of the oligosaccha ride are selected from the grou p consisting of fructose, glucose, sucrose, xylose, maltose, mannose, rha mnose, galactose, lactose, gentiobiose, sophorose, 2-gl ucopyra nosyl- glucose, glucopyra nosyl-(l-2)-[glucopyra nosyl-(l-6)] -glucopyra nose, cellobiose, mannitol, sorbitol, xylitol or arabitol, glucuronic acid, quinovose, arabinopyra nose, arabinofura nose, xylopyra nose, xylofura nose and/or apiose (2,3,4-tri hydroxy-3- (hyd roxymethyl)buta nal), and wherein the oligosaccha ride consists of 2 t o 5 monosaccha ride units.

2. A com pou nd of form ula (I) accordi ng t o claim 1, whe rei n

R and R2 are independently of one another and denote hydroxyl or a suga r moiety selected from a monosaccha ride and/or oligosaccha ride,

whe rei n the monosaccha ride and/or the monosaccha ride units of the oligosaccha ride are selected from the grou p consisting of glucose, 2-glucopyra nosyl-glucose, 3- glucopyra nosyl-gl ucose, 4-gl ucopyra nosyl-glucose, 6-glucopyra nosyl-gl ucose, or gluco- pyranosyl-(l-> 2)-[glucopyra nosyl-(l-> 6)]-glucose, and

whe reby in case of the oligosaccha ride, the monosaccha ride units of the oligosaccha ride are lin ked via glycosidic bonds t o each other, and

R3 denote hydrogen, hyd roxyl or ca rbonyl. 3. A com pou nd of form ula (I) accordi ng t o claims 1 or 2, wherei n in case

R2 is an oligosaccha ride with 2 monosaccha ride units (disaccha ride), the monosaccha

ride units of the disaccha ride of R2 are lin ked via glycosidic bonds together, which is not a l - 6 lin king.

4 . A com pou nd of form ula (I) accordi ng t o claims 1 t o 3, wherein

R2 is an oligosaccha ride with 2 monosaccha ride units (disaccha ride), and

R3 denote hydrogen or ca rbonyl. 5. A com pou nd of form ula (I) accordi ng t o claims 1 t o 3, wherein

R denotes hyd rogen, hydroxyl, ca rbonyl or an oligosaccha ride with 2, 3, 4 or 5 monosaccha ride units, and

R2 is an oligosaccha ride with 2 monosaccha ride units (disaccha ride), and

R3 denotes hyd roxyl. 6. A com pou nd of form ula (I) accordi ng t o claims 1 or 2, wherei n in case

R2 is an oligosaccha ride with 3 monosaccha ride units (trisaccha ride), then - Ri is ca rbonyl and/or

- R3 is not hydroxyl or ca rbonyl or

- R3 is hydroxyl and Ri is an oligosaccha ride with 2, 4 or 5 monosaccha ride units, whe rei n the monosaccha ride units of the oligosaccha ride of Rl are li nked via glycosidic bonds together which is not a l - 6 or l - 4 lin king.

7. A com pou nd of form ula (I) accordi ng t o claims 1 t o 4, wherein

Ri is a monosaccha ride or an oligosaccha ride with at least 3 monosaccha ride units, and

R2 is an oligosaccha ride with 3 monosaccha ride units (trisaccha ride), and

R3 is ca rbonyl. 8. A com pound of form ula (I) according t o clai ms 1 t o 5, wherei n Ri is an oligosaccha ride with 2, 4 or 5 monosaccha ride units, but not with 3 monosaccha ride units.

9. A com pound of form ula (I) according t o claims 1 or 2, wherei n R2 is an oligosaccha ride with 2 t o 5 monosaccha ride units, but not a (single) monosaccha ride. A compound of formula (I) according to claims 1 to 4, wherein in case R2 is carbonyl, then

- R3 is not carbonyl or

- R3 is hydroxyl.

A sweetener compound of formula (I) according to claims 1 to 10, wherein the co m pound of formula (I) is selected from the group consisting of: 3,ll-dihydroxy-4,4,9,13,14-pentamethyl-2,3,4,7,8,9,10,ll,12,13,14,15,16,17- tetradecahydro-lH-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 (compound A); ,5-dihydroxy-2-(2-hydroxy-2-methyl-6-((3S)-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-lH-cyclopenta[a]phenanthren-17-yl)heptan-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 B); 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,ll,12,13,14,15,16,17-tetradecahydro- lH-cyclopenta[a]phenanthren-3-yloxy)-4,5-dihydroxy-2- (hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H- pyran-3,4,5-triol (compound C); 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-yl)- 4,4,9,13,14-pentamethyl-2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro- lH-cyclopenta[a]phenanthren-3-yloxy)-4,5-dihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H- pyran-3,4,5-triol(compound D); 2-(4,5-dihydroxy-2-(2-hydroxy-2-methyl-6-(4,4,9,13,14-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-lH- cyclopenta[a]phenanthren-17-yl)heptan-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 E); 2-((6-(6-(3-(4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxytetrahydro-2H- pyran-2-yloxy)tetrahydro-2H-pyran-2-yloxy)-ll-hydroxy-4,4,9,13,14- pentamethyl-2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH- cyclopenta[a]phenanthren-17-yl)-2-hydroxy-2-methylheptan-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 F); 2-(4,5-dihydroxy-2-(3-hydroxy-2-methyl-6-(4,4,9,13,14-pentamethyl-3-(3,4,5- trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)- 2,3A7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH- cyclopenta[a]phenanthren-17-yl)heptan-2-yloxy)-6-(hydroxymethyl)tetrahydro- 2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (compound G); 2-hydroxy-6-(ll-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,ll,12,13,14,15,16,17-tetradecahydro-lH- cyclopenta[a]phenanthren-17-yl)-2-methylheptan-3-one (compound H); 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)-ll- hydroxy-4,4,9,13,14-pentamethyl-4,7,8,9,10,ll,12,13,14,15,16,17-dodecahydro- lH-cyclopenta[a]phenanthren-3(2H)-one (compound J); 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-lH- cyclopenta[a]phenanthren-17-yl)-2-methylheptan-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 K); 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-lH- cyclopenta[a]phenanthren-ll(2H)-one (compound L); 2-(4,5-dihydroxy-2-(2-hydroxy-2-methyl-6-(4,4,9,13,14-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-lH- cyclopenta[a]phenanthren-17-yl)heptan-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 M); A preparation, comprising one, two, three or more of a sweetener compound of for mula (I) according to claims 1 to 11, wherein the preparation optionally further co m prises aroma compounds and/or flavouring agents and/or sweeteners and/or sweet- tasting substances.

Use of a sweetener compound of formula (I) according to claims 1 to 11 or a prepara tion according to claim 12 to sweet or enhance the sweeting effect in compositions which are administered to an individual in an effective amount sufficient to produce the desired degree of sweetness. An extract comprising one or more of a compound of formula (I) according to claims 1 to 11, wherein the extract is obtainable by the method of aqueous and / or alcoholic extraction of the plant Momordica grosvenorii (Synononym Siraitia grosvenori).

The extract according to claim 14, comprising at least a compound of formula (I) se lected from the group consisting of: (2S,3R,4S,5S,6R)-2-((2S,3R,4S,5S,6R)-2-((3R,6R)-6-((3S,8S,9R,llR,13R,14S,17R)- 3,ll-dihydroxy-4,4,9,13,14-pentamethyl-2,3,4,7,8,9,10,ll,12,13,14,15,16,17- tetradecahydro-lH-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 (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-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,ll,12,13,14,15,16,17-tetradecahydro-lH- 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 (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-methylheptan-2-yl)-4,4,9,13,14-pentamethyl- 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-lH- cyclopenta[a]phenanthren-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-lH- cyclopenta[a]phenanthren-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-tetradecahydro-lH- 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 (compound Ee)

(2S,3R,4S,5S,6R)-2-((2R,3R,4S,5S,6R)-2-((3S,8S,9R,llR,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)-ll-hydroxy-4, 4,9,13,14- pentamethyl-2,3,4,7,8,9,10,ll,12,13,14,15,16,17-tetradecahydro-lH- cyclopenta[a]phenanthren-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-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)- 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-lH- cyclopenta[a]phenanthren-17-yl)heptan-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,llR,13R,14S,17R)-ll-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,ll,12,13,14,15,16,17-tetradecahydro-lH- cyclopenta[a]phenanthren-17-yl)-2-methylheptan-3-one (compound Hh) (9R,10R,llR,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)-ll-hydroxy-4,4,9,13,14-pentamethyl-4,7,8,9,10,ll,12,13,14,15,16,17- dodecahydro-lH-cyclopenta[a]phenanthren-3(2H)-one (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-lH- 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 (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-y|)-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-lH-cyclopenta[a]phenanthren-ll(2H)-one (compound LI) (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,H,12,13,14,15,16,17-tetradecahydro-lH- 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 (compound Mm).

A . CLASSIFICATION O F SUBJECT MATTER INV. A23L1/236 C07J17/00 ADD.

According to International Patent Classification (IPC) o r t o both national classification and IPC

B . FIELDS SEARCHED Minimum documentation searched (classification system followed by classification symbols) A23L C07J

Documentation searched other than minimum documentation to the extent that such documents are included in the fields searched

Electronic data base consulted during the international search (name of data base and, where practicable, search terms used)

EPO-Internal , WPI Data, FSTA

C . DOCUMENTS CONSIDERED T O B E RELEVANT

Category* Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No.

X US 4 084 010 A (TAKEM0T0 TSUNEMATSU ET AL) I - 9 , 11 Apri l 1978 (1978-04-11) II- 15 A abstract; cl aims 10

X US 2012/059071 Al (MARKOSYAN AVETI K [MY] ) 1-3 , 5 ,8, 8 March 2012 (2012-03-08) 9 , 12-14 ci ted i n the appl i cati on paragraph [0002] ; cl aims 9 , 12 ; exampl e I ; tabl e 1

US 2011/027413 Al (JIA ZH0NGHUA [US] ET 1, 2 ,8,9 , AL) 3 February 2011 (2011-02-03) 12-14 ci ted i n the appl i cati on abstract

J P S57 86266 A (HAYASHIBARA BI0CHEM LAB; 1, 2 , JAPAN CHEM RES) 29 May 1982 (1982-05-29) 12-14 abstract

□ Further documents are listed in the continuation of Box C . See patent family annex.

* Special categories of cited documents : "T" later document published after the international filing date o r priority date and not in conflict with the application but cited to understand "A" document defining the general state of the art which is not considered the principle o r theory underlying the invention to be of particular relevance "E" earlier application o r patent but published o n o r after the international "X" document of particular relevance; the claimed invention cannot be filing date considered novel o r cannot b e considered to involve a n inventive "L" documentwhich may throw doubts o n priority claim(s) orwhich is step when the document is taken alone cited to establish the publication date of another citation o r other "Y" document of particular relevance; the claimed invention cannot be special reason (as specified) considered to involve a n inventive step when the document is "O" document referring to a n oral disclosure, use, exhibition o r other combined with one o r more other such documents, such combination means being obvious to a person skilled in the art "P" document published prior to the international filing date but later than the priority date claimed "&" document member of the same patent family

Date of the actual completion of the international search Date of mailing of the international search report

20 October 2014 27/10/2014

Name and mailing address of the ISA/ Authorized officer European Patent Office, P.B. 5818 Patentlaan 2 N L - 2280 HV Rijswijk Tel. (+31-70) 340-2040, Fax: (+31-70) 340-3016 Saunders , Thomas Patent document Publication Patent family Publication cited in search report date member(s) date

US 4084010 11-04-1978 NONE

US 2012059071 Al 08 -03 -2012 EP 2425721 Al 07-03-2012 EP 2622969 Al 07-08-2013 ES 2440780 T3 30-01-2014 US 2012059071 Al 08-03-2012 us 2011027413 Al 03 -02 -2011 EP 2188300 A2 26-05-2010 US 2011027413 Al 03-02-2011 US 2014170286 Al 19-06-2014 O 2009023975 A2 26-02-2009

P S5786266 A 29 -05 -1982 P S5786266 A 29-05-1982 P S5848155 B2 26-10-1983