Indian Patents. 271308:ROASTED EXTRACT CONTAINING XANTHOHUMOL, AND METHOD FOR THE PRODUCTION THEREOF AND PRODUCTS PRODUCED THEREFROM

Title of Invention	ROASTED EXTRACT CONTAINING XANTHOHUMOL, AND METHOD FOR THE PRODUCTION THEREOF AND PRODUCTS PRODUCED THEREFROM
Abstract	The invention relates to a method for producing an extract containing xanthohumol (XN), which is obtained from toasted cereal products, cereal malt, coffee or cocoa. The XN-content in said extract is in the region of 10 mg/kg - 2 g/kg xanthohumol. The use of XN-toasted extracts enables the XN-content of foodstuffs and pharmaceutical products to be increased in a natural manner.

Full Text	Description Natural extract comprising fcanthohumol, and method for the production thereof and products produced therefrom Technical field The present invention reives to a method for producing a roasted extract from cereals, cereal malt or coffee comprising xanthohurnol (XN) and a hop extract comprising xanthohuaiol) as well as its use for the production of beverages and/or food products. Background art Hop is used as raw mateial for the production of beer. Hop provides the bitter impression of beer but atyb an elongated shelf life due to its antibacterial effect. The most important compcfunds contained in hop are, besides the bitter acids Xanthohumol, a ptenylflayonoid (polyphenol) of hop which occurs in the lupulin glands of the hop conefc has a plurality of positive effects. Beside the antiviral and the anti-oestrogenj\|c and anti-inflammatory effect, a cancer-chemo preventive activity of XN is attso discussed which activity is currently under investigation in animal experiments. The content of xanthdhumol in hops varies depending on the hop variety between 0.1 and 1 %. The hop varieties having a high content ot'xanthohurnol usually comprise a high portion of bitter substances. Hop products may be [divided in raw [hops, hop pellets and hop extracts. Since xanthohumol occurs oijly in the lupuluj glands of the hop cone, hop pellets exhibit a high content of XN\| corresponding (to the accumulation of ctracids. Hop extracts may be obtained by' extraction with extract hardly comprises any xanthohumol CO2 and/or ethancl. Whereas CO: XN is extracted almost completely during the ethanol extraction] Recently, XN bunched products are produced by a combination of both eXtractiofi methods. Depending on the production method XN contents of between 8 and In the brewing process xanthohumol \|s relatively instable and is mainly precipitated via the trub, the yeast, by filtration and stabilisation due to its limited solubility. Besides, xanthohurhol is isomerisefl to iso-xanthohumol wliich also has u positive effect, however, to Quite a lower extent compared to xanthohumol. With the conventional method less! then 0.2 me/1 KN are reached in the final beer in most of the cases. In some sjout or porter tyjpfe dark beers XN contents of up to 1.2 mg/1 XN were found (Walker et al., Brauwelt 2003). With a special brewing method which applies late hooping and a fast pooling of the beer wort it is possible to increase the XN consent in non-ffltered pale beers to 1-10 mg/1 (DE 102 56166). It is an advantage of the present iivention that the isomerisation of xanthohumol to iso-xantbohjimol is supresfsed to a large extent due to the improvement of the brewing method. Therefore, it is possible to increase dosage amounts of XN without allohvine the beers! to become unpleasantly bitter, for instance. Further, the addition of stabilisers is\|possible which would normally lea;l to a relevant decrease in the XN content. A method for producing the roasted extract comprising XN from roasted products of cereals, cereal maty, coffee or cacao and a hop extract comprising XN is an object of the present' (invention. The hop extract comprising XN is characterised by a particularly \|i\|gh content of xanthohurnol. It is in the range from 10 mg to 2 g/kg, preferably in t\|h\|e range of 200 mg to 850 mg/kg. Due to the use of this roasted extract beers with\|a significant increased content of XN compared to the prior art can be obtained! in accordance with the German purity law, for instance. Herein, "roasted extract)' comprising XN" denotes an extract which is obtainable from a roasted extrtact from roasted products of cereals, cereal malt. coffee or cacao and from th4' hop extract comprising XN. "Roasted extract" denotes a cold or hot extract ftftm coarsely ground or non-ground roasted malt or cereals and includes a hot or liold extract from coffee or cacao; "cereal malt" denotes a cereal that was artificially or controllably allowed to germinate, and "hop extract comprising XN" denoteslan extract from hops which was obtained with the aid of a solvent and exhibits afl increased content of XN. "Basic materials" is a collective term for plain or oHmbined substances which may be of natural or synthetic origin. They are used & parent material for the farther production of food products, In the present invention basic materials denote e.g. essences which may be enriched with XN as well fls e.g. a basic material for coke according to an embodiment of the present inveiRtion. For producing roasted exttact comprising XN a hot aqueous extract of the ground roasted products e.g. of barley, wheat, rye as well as the corresponding malts, coffee beans or cacao b«fens is prepared. A hop extract comprising XN is added thereto at the beginning of the heating period. The extraction of .xanthwhurnol in the extractions'! of the roasted products leads to a XN content which is by far higher than the solubility limit of XN in typical aqueous solutions. This amounts to 1.3 mg/I of ^N at a water temperature of 23. °C and to 1.1 mg/1 of XN at a water temperature of 8 °C. Soluble roasted substances which absorb or bind XN and therefore, apparently keep it in solution, are orobablvl responsible for the high yields of xanthoburriol in the extracts] The extracts pay be fermented, concentrated or clarified without noteworthy josses of XN. AJecording to one embodiment of the present invention a xanthohWoI content of approximately 1320mg/kg was obtained in the extract after concentration of tl}e XN comprising roasted malt wort. The XN comprising roasted malt wortnjay be used in the food industry such as in the brewing and beveragb industry as wo\|ll as in the foodstuff industry. Thus, the application of the XN comprising roasted \|nalt wort may lead to an enrichment of xanthohumol in spirits, hejrbal spirits, herbal liquor wine, beer, mixed drinks comprising beer, or bitters, an{! also of non-alifoholic drinks or drinks with reduced alcohol content such as malt tyeverages, coffe^, coffee substitute, cacao, ice tea or soft drinks as well as of basii materials for the production of such products in a simple, safe and economic wa(y, A particular ^dvantage is that a roasted malt beer enriched with XN and prepared according jo this method may be added to a conventionally produced beer\| at any time of the beer production in accordance with the purity law, i.e., withput the use of ejtnulsifying agents or other chemical additives. An enrichment of food ijroducts with xajnthohumol, such as bakery products, backing kits, parfaits, dairy products Ce.e. yoghurt, curd cheese and mixed drinks comprising milk) desserts, ice' cream, meat -products, sauces and herbal candies as well as enrichment of pharmajceutical products with xanthohumol, such as cough syrup, is also possible. The method for preparing I Jan aqueous extract comprising XN from roasted products of cereals, cereal malt, \|[coffee or cacao comprises the following process steps: a) addition of a hop product comprising XN to an extract which is mainly or completely produced frcjfri roasted or colour malts, respectively, or roasted barley; wherein the added hop product has a content of XN which is, related to the mass used'for its production, at least 5 times that of the hops used for its production; ^nd wherein after the addition of the hop product comprising xanthohunxf to the aqueous roasted extract the dissolving or even an intensive dissolving of XN is reached, despite the original low solubility in aqueous solutions; b) dissolving of XN by pr^-dissolving of the XN comprising hop product in ethano.l; c) dissolving of XN by ajgitating, mixing, shaking, supersonic treatment, ultraturax treatment or other mechanical forces; d) dissolving of XN by heading of theroasted extract; e) dissolving of XN by application of an alternating current; () wherein the amount of tjhe addition of the hop product comprising XN is al least 50 mg XN per litre, As will be understood fronji the following examples, it is not necessary that all of the previously mentioned process steps are realised when implementing the process. The process steps b) to hjj are optional. In the fbllowingj examjples of methods according to the present invention and beverages produced thereby kre given. Example 1 Preparation of beer wcjrt from a mixtur^ of special malt comprising 1.9 kg of roasted barley malt (Carafal™. tvne 2. Pa. ^eyermann, Bamberg) and 0.1 kg of Pils.cn type malt. After msjshing according! to the congress method and mash separation 25 g/1 of a hop ektract enriched with XN were added (XanthoExtrakt, Simon H. Steiner Hopfen CfrnbH, XN 2.0 °4) during boiling of the roasted mall wort with the kettle-up woi\|t concentration 4>f 11 %w/w (weight/weight percent) and a wort colour of 1650 EfJC (European Brewing Convention). After separation of hot trub and a separation with diatomaeeous earth the roasted malt won comprising XN was concenltrated in vacuo 1(200 mbar, ca. 55 °C) to an extract content of approximately 5Q%w/w. The syijup like extract ("density 1.25" kg/1) had a colour of approximately 7500 EBC and a content of xanthohumol of approximately I320mg/kg. Example 2 Preparing of beer wort'from a special nature comprising 0,05 kg of PiLsen type malt and 0.95 kg of Roasted barley rhalt (Garafa1M, Weyermann). After mashing according to the congress method I and mash separation the won was boiled for 2 hours. At the staik of boilina 500d mg/1 of XN were added to the wort. For this, a hop extract comprising XN with 8\|) % of diatomaeeous cardi and 20 % of hop extract (XanthoExtrakt. Honsteiner xfNT 1.7 %) was used. Beside XN. this extract also comprises a-acitis and hard resins which have an influence on the flavour. The cast wort having) a concentration)of 11.7 %w/w was fermented within 2 days by bottom fermenting brewer's yeast \|and wag centrifuged after 5 days of storage. The resulting roasted nuj\|t beer (RMB) had a colour of 1850 EEC and an XN content of 390 rag/I. Example 3 Method for preparing a roasted malt extract comprising XN according to example 1, however, the wort w$ fermented with brewer's yeast, centrifuged and tillered with diatomaeeous earth flrior to Concentration. The roasted malt beer thus prepared and having an original!'extract of 12% and a colour of approximately 1700 EBC, had an XN content 0^46 mg/1. Bxample 4 Method for preparing a iftaisted malt beer comprising XN according to example 3, however, the RMBl'was concentrated after the filtration in vauuo (200 mbar, ca. 55 °C) to an extract content of approximately 48 %. The density of the syrup like roasted malt beer'comprising XN was approximately 1,2 kg/1, the colour was 6900 EBC, and the XN content was 846 mg/kg. Example 5 Method for preparing a rd/isted malt extract comprising XN according ID example 1, however, an amount] (of approximately 100 mg XN per litre of won 11 i %w/w roasted malt extract! was dosed. Further treatment according to examples 3 and 4 gave a roasted] Jnalt beer with an extract content of 47 %w/\v. a density of 1.2 kg/I, a colour of 72Ju\|o EBC and a XN content of 341 mg/1. Example 6 Preparation of a coffe^ extract from 40 \|g of ground roasted coffee and I litre of hot water. After separaiiion of the cofFele grounds lOOmg of a hop extract comprising XN (XN content 80 %) were added to the hot coffee extract. The hop extract was intensively mixfcd at temperatures of above 60 °C and it was further dissolved at 8 °C for 24hot[rs. After filtration of the coffee beverage comprising XN using a fluted filter the coffee beverage had an XN content of more than 12 mg/l. Example 7 Method for preparing; a coffee bevdrage comprising XN according lo example 6, however, the filtered coffee beverage was dried in a freeze drier to a water content of less than 10 %, The soluble coffee beverage comprising XN had an XN content of 1042mg/k£. Example 8 Approximately t.8g lof the soluble! coffee beverage comprising XN according to example 7 were- mixed with 15C(ml of hot water. The XN content tif the mixed coffee beverage W4$ approximately 10 mg/1. Example 9 To a non-filtered pale lager beer (XN iontent 0.1 mg/1) 2 g/I of the roasted malt beer comprising XN according to exanjple 4 were added. Compared to the control beer a colour increases by 15 EBC arjd an enrichment of XN by 1.8 mg/1 were detected in the bright be£r. Example 10 To a non-filtered pale kg# beer (XN content 0.1 mg/1) 20 g/1 of the roasted malt beer comprising XN acceding to example 4 were added. The filtered beer had a colour of 120 EEC and a JfH content of 13 mg/1. Ex ample 11 To a filtered pale lager beejtl (XN content 0.05 mg/1) 20 g/1 of the roasted mall beer comprising XN according it example 4 were added. The mixed filtered beer had a colour of 125 EBC and an XN content of 15 mg/1. Example 12 To a typical basic material for coke consisting of two components, coke essence, caramel colour and caffeine on the one hand, and phosphoric acid on the other hand, 880 g of a roasted riialt beer comprising XN according to example 1 (concentration 1320 mgXN/kg)"were added to 3.05kg basic coke material and homogenised. After mixing of tJie enriched basic material with processed water (3:1000), carbon dioxide (6.2 g/1) and sugar (.110 g/1) a xanthohumol content of I.I mg/1 was determined in the r^kdy-to-drink beverage. Example 13 To one kilogram of prfjpiotic yogurt 2.29 g of roasted malt extract comprising. XN according to Sample 1 is added and homogenised. In the pasteurised product a xanthohum!c\|l content of 0.3 mg/100 g was detectable, Example 14 To a pharmaceutical pfroduct, here 1 litre of cough syrup, a roasted malt extract comprising XN (7.6 £) according to example 1 was added. The resulting product comprised approximaltely 1.0 mgXN/JOO ml. 1. Roasted Extract comprisifig xanthohumol (XN), obtainable from a. roasted extract and a hop extract (Jomprising XN. 2. Roasted extract comprisiig XN according to claim 1, characterised in that the roast extract includes a cold or hot extract of coarsely ground or non- ground roasted malt, cereals, coffee or cacao. 3. Roasted extract comprisijjig XN according to anyone of claims I and 2, characterised in that the r&asted XN extract has an XN content in the range of'10mg/kgto2 g/kg. 4. Roasted extract comprishpig XN according to claim 3, characterised in that has an XN content in rage of 50 mg/kg to the roasted XN extract 1320 mg/kg, particularly to a range of 200 mg/kg to 850 mg/kg. 5. Pharmaceutical eompositfpn, characterized in that it comprises a roasted extract comprising XN acbording to anyone of claims 1 to 4. Q. Pharmaceutical product Recording to claim 5, characterised in that the pharmaceutical composition is a cough syrup. 7. Food product, characterised in that it comprises a roasted extract comprising XN according Jo anyone of claims 1 to 4. tS. Food product according tjcf claim 7, characterised in that the food product includes alcoholic, alcohcjl (reduced and non-alcoholic beverages. °. Food product according to claim 8, Characterised iii that the alcoholic or alcohol reduced beverages include beferages such as spirits, herbal spirits, herbal liqueurs, bitters , wine, beef, or ijnixed beverages comprising beer. 10. Food product accordirfg to claim 8, .characterised in that the non-alcoholic beverages include beverages such as Isoft drinks, coffee beverages, coffee substitute, malt beveijages, ice tea o)r basic materials for producing the same. 11. Food product according to claim 8, ^herein the food product comprises bakery products, parfa^ts, dairy produces* sweets, sauces and meet products. 12. Food product accordiJiE to anyone df claims 7 to II, wherein the XN content is 10 mg/1 to 400 mg/I, preferably from 12 mg/I to 390 mg/l, more preferably 15 mg/1 to 2J46 mg/I. 13. Method for producing' a roasted extijact Comprising XN, wherein a hop extract comprising X>\| is mixed with \|a cold or hot extract from a coarsely ground or non-ground concentrated thereafter roasted malt, cjereals, coffee or cacao and which is 14. Method according to cjlaim 13, wherejln the added hop extract comprising XN has a content of X$ which is in a ifange from 0.5 to 99 %w/w of XN. 15. Method according to claim 13, wherein the roasted extract comprising XN is concentrated to dily matter of 40-50 %w/w (weight/weight percent). particularly to 47 to 48 l%w/w. 16. Method according to c\|aim 15, wherein the concentrating is performed by evaporating, freeze drying or at reduceti pressure. 17, Method according to anyone of claims 13 to 16, wherein the roasted extract comprising XN is fermerjt)ed by yeast and clarified. 18, Method according to cljaUrn 17, wherein the clarifying is effected by a centrifuging or filtrating 19, Method according to anyone of claims 17 and 18, wherein the roasted malt beer enriched with XN isj concentrated to an extract content of 40-50 %w/w in particular to 47-48 20. Method according to clalfri 13, wherein the hop extract is pre-dissolved in ethanol for dissolving of ftie XN. 21. Method according to claifri 20, wherein the XN is dissolved by agitating, mixing, shaking, super $>nic treatment and/or treatment with dispersing means. 22. Method according to anyone of claims 20 and 21, characterised in that the dissolving of xanthohurnJ4>l farther includes heating and/or the application of an alternating current, 23. Method for producing ait aqueous extract comprising XN from roasted products of cereals, eereaJImaltj or coffee, characterised in that: a) tile hop product Comprising XN is added to an extract which is mainly or completely produced from roasted or colour mall, respectively, or roiisted barley; b) the added hop prdauct has an XN content which, related 10 its mass used for its production, is at least five times that of the hop used tor its production; c) dissolving or 4ven an intensive dissolving of XN is achieved after the addition c\|f the hop product comprising XN to the aqueous roasted extract despite the ojriginally low solvability in aqueous solutions; \| d) dissolving is comprising X> e) dissolving of promoted by jpre-dissolving of the hop product in ethanol; ' XN is prorno[ted by agitating, mixing, shaking. supersonic treatment, Ultratura* treatment or any other mechanical forces; f) dissolving of XJN is promoted fy heating of the roasted extract; g) dissolving of XJN is promoted \|y applying an alternating current; h) the amount of ^acution ot the rjop product comprising XN is at least 50mgofXNp\|erlitre. 24. Method for producing the roasted ejxtract comprising XN according to claim 23, further characterised in thjat the extract enriched with XN is concentrated to a dry rrtatter ot approximately 50 %. 25. Method for producing) the roasted extract comprising XN according tci claim 23, further charatterised in that a) the extract enriched with XN \|s fermented by yeast, centrifuged or filtered; b) the roasted rriald beer enriched with XN is concentrated to an extract content of e.g. 30 %. 26.. Method for producing the extract comprising XN according to anyone of claims 23 to 25, fiirtHo" characterisdd in that a commercially available roasted rrialt extract and a commercially available roasted malt beer is used for dissolving the hop ektract enriched [with XN. 27. Method for producing $ roasted extract comprising XN according to anyone of claims 23 and 2H further characterised in that an extract from the commercially available rested coffee and from the commercially available instant coffee is used for Dissolving this hop extract enriched with XN. 28. Roasted extract comprisnjig xanthohumol with an XN content of more than 10 mg/kg which is produced according to anyone of claims 23 to 27, wherein the use of this expect is intended for the natural enrichment of XN in beverages such as beet' mixed beverages comprising beer, wine, coffee beverages, coffee substitute or another non-alcoholic beverage or u precursor of these product! 29. Roasted extract comprisuji^ xanthohumol with an XN content of more than ! 0 mg/kg which is produced according to anyone of claims 23 to 27, wherein the use of thSi extract is intended for the production of xanthohumol comprising jb^akery products, parfait, desserts, ice cream, meal products, sauces, and similar products or a precursor of these products. 30. Roasted extract oomprisiit xanthohumol with an XN content of more thun 50 mg/kg which is produc ed according to anyone of claims 23 to 27. 31. Roasted extract cdmprisiihfc xanthohumol with an XN content of more than 200 mg/kg which is prodiitfed according to anyone of claims 23 to 27. 32. Roasted extract cornprisii^ xanthohumol with an XN content of more than 200 mg/kg.

Full Text

Description
Natural extract comprising fcanthohumol, and method for the production thereof and products produced therefrom
Technical field
The present invention reives to a method for producing a roasted extract from cereals, cereal malt or coffee comprising xanthohurnol (XN) and a hop extract comprising xanthohuaiol) as well as its use for the production of beverages and/or food products.
Background art
Hop is used as raw mateial for the production of beer. Hop provides the bitter impression of beer but atyb an elongated shelf life due to its antibacterial
effect.
The most important compcfunds contained in hop are, besides the bitter acids Xanthohumol, a ptenylflayonoid (polyphenol) of hop which occurs in the lupulin glands of the hop conefc has a plurality of positive effects. Beside the antiviral and the anti-oestrogenj|c and anti-inflammatory effect, a cancer-chemo preventive activity of XN is attso discussed which activity is currently under investigation in animal experiments. The content of xanthdhumol in hops varies depending on the hop variety between 0.1 and 1 %. The hop varieties having a high content ot'xanthohurnol usually comprise a high portion of bitter substances.

Hop products may be [divided in raw [hops, hop pellets and hop extracts. Since xanthohumol occurs oijly in the lupuluj glands of the hop cone, hop pellets exhibit a high content of XN| corresponding (to the accumulation of ctracids. Hop

extracts may be obtained by' extraction with extract hardly comprises any xanthohumol

CO2 and/or ethancl. Whereas CO: XN is extracted almost completely

during the ethanol extraction] Recently, XN bunched products are produced by a combination of both eXtractiofi methods. Depending on the production method XN contents of between 8 and
In the brewing process

xanthohumol |s relatively instable and is mainly

precipitated via the trub, the yeast, by filtration and stabilisation due to its limited solubility. Besides, xanthohurhol is isomerisefl to iso-xanthohumol wliich also has u positive effect, however, to Quite a lower extent compared to xanthohumol. With the conventional method less! then 0.2 me/1 KN are reached in the final beer in most of the cases. In some sjout or porter tyjpfe dark beers XN contents of up to 1.2 mg/1 XN were found (Walker et al., Brauwelt 2003). With a special brewing method which applies late hooping and a fast pooling of the beer wort it is possible to increase the XN consent in non-ffltered pale beers to 1-10 mg/1 (DE 102 56166).
It is an advantage of the present iivention that the isomerisation of xanthohumol to iso-xantbohjimol is supresfsed to a large extent due to the improvement of the brewing method. Therefore, it is possible to increase dosage amounts of XN without allohvine the beers! to become unpleasantly bitter, for instance. Further, the addition of stabilisers is|possible which would normally lea;l to a relevant decrease in the XN content.

A method for producing the roasted extract comprising XN from roasted products of cereals, cereal maty, coffee or cacao and a hop extract comprising XN is an object of the present' (invention. The hop extract comprising XN is characterised by a particularly |i|gh content of xanthohurnol. It is in the range from 10 mg to 2 g/kg, preferably in t|h|e range of 200 mg to 850 mg/kg. Due to the use of this roasted extract beers with|a significant increased content of XN compared to the prior art can be obtained! in accordance with the German purity law, for instance.
Herein, "roasted extract)' comprising XN" denotes an extract which is obtainable from a roasted extrtact from roasted products of cereals, cereal malt. coffee or cacao and from th4' hop extract comprising XN. "Roasted extract" denotes a cold or hot extract ftftm coarsely ground or non-ground roasted malt or cereals and includes a hot or liold extract from coffee or cacao; "cereal malt" denotes a cereal that was artificially or controllably allowed to germinate, and "hop extract comprising XN" denoteslan extract from hops which was obtained with the aid of a solvent and exhibits afl increased content of XN. "Basic materials" is a collective term for plain or oHmbined substances which may be of natural or synthetic origin. They are used & parent material for the farther production of food products, In the present invention basic materials denote e.g. essences which may be enriched with XN as well fls e.g. a basic material for coke according to an embodiment of the present inveiRtion.
For producing roasted exttact comprising XN a hot aqueous extract of the ground roasted products e.g. of barley, wheat, rye as well as the corresponding malts, coffee beans or cacao b«fens is prepared. A hop extract comprising XN is added thereto at the beginning of the heating period. The extraction of .xanthwhurnol in the extractions'! of the roasted products leads to a XN content which is by far higher than the solubility limit of XN in typical aqueous solutions.

This amounts to 1.3 mg/I of ^N at a water temperature of 23. °C and to 1.1 mg/1 of XN at a water temperature of 8 °C.
Soluble roasted substances which absorb or bind XN and therefore, apparently keep it in solution, are orobablvl responsible for the high yields of xanthoburriol in the extracts] The extracts pay be fermented, concentrated or clarified without noteworthy josses of XN. AJecording to one embodiment of the present invention a xanthohWoI content of approximately 1320mg/kg was obtained in the extract after concentration of tl}e XN comprising roasted malt wort.
The XN comprising roasted malt wortnjay be used in the food industry such as in the brewing and beveragb industry as wo|ll as in the foodstuff industry. Thus, the application of the XN comprising roasted |nalt wort may lead to an enrichment of xanthohumol in spirits, hejrbal spirits, herbal liquor wine, beer, mixed drinks comprising beer, or bitters, an{! also of non-alifoholic drinks or drinks with reduced alcohol content such as malt tyeverages, coffe^, coffee substitute, cacao, ice tea or soft drinks as well as of basii materials for the production of such products in a simple, safe and economic wa(y, A particular ^dvantage is that a roasted malt beer enriched with XN and prepared according jo this method may be added to a conventionally produced beer| at any time of the beer production in accordance with the purity law, i.e., withput the use of ejtnulsifying agents or other chemical additives.
An enrichment of food ijroducts with xajnthohumol, such as bakery products, backing kits, parfaits, dairy products Ce.e. yoghurt, curd cheese and mixed drinks comprising milk) desserts, ice' cream, meat -products, sauces and herbal candies as well as enrichment of pharmajceutical products with xanthohumol, such as cough syrup, is also possible.

The method for preparing I Jan aqueous extract comprising XN from roasted products of cereals, cereal malt, |[coffee or cacao comprises the following process steps:
a) addition of a hop product comprising XN to an extract which is mainly or
completely produced frcjfri roasted or colour malts, respectively, or roasted
barley; wherein the added hop product has a content of XN which is,
related to the mass used'for its production, at least 5 times that of the hops
used for its production; ^nd wherein after the addition of the hop product
comprising xanthohunxf to the aqueous roasted extract the dissolving or
even an intensive dissolving of XN is reached, despite the original low
solubility in aqueous solutions;
b) dissolving of XN by pr^-dissolving of the XN comprising hop product in
ethano.l;
c) dissolving of XN by ajgitating, mixing, shaking, supersonic treatment,
ultraturax treatment or other mechanical forces;
d) dissolving of XN by heading of theroasted extract;
e) dissolving of XN by application of an alternating current;
() wherein the amount of tjhe addition of the hop product comprising XN is al least 50 mg XN per litre,
As will be understood fronji the following examples, it is not necessary that all of the previously mentioned process steps are realised when implementing the process. The process steps b) to hjj are optional.

In the fbllowingj examjples of methods according to the present invention and beverages produced thereby kre given.
Example 1
Preparation of beer wcjrt from a mixtur^ of special malt comprising 1.9 kg of roasted barley malt (Carafal™. tvne 2. Pa. ^eyermann, Bamberg) and 0.1 kg of Pils.cn type malt. After msjshing according! to the congress method and mash separation 25 g/1 of a hop ektract enriched with XN were added (XanthoExtrakt, Simon H. Steiner Hopfen CfrnbH, XN 2.0 °4) during boiling of the roasted mall wort with the kettle-up woi|t concentration 4>f 11 %w/w (weight/weight percent) and a wort colour of 1650 EfJC (European Brewing Convention). After separation of hot trub and a separation with diatomaeeous earth the roasted malt won comprising XN was concenltrated in vacuo 1(200 mbar, ca. 55 °C) to an extract content of approximately 5Q%w/w. The syijup like extract ("density 1.25" kg/1) had a colour of approximately 7500 EBC and a content of xanthohumol of approximately I320mg/kg.
Example 2
Preparing of beer wort'from a special nature comprising 0,05 kg of PiLsen type malt and 0.95 kg of Roasted barley rhalt (Garafa1M, Weyermann). After mashing according to the congress method I and mash separation the won was boiled for 2 hours. At the staik of boilina 500d mg/1 of XN were added to the wort. For this, a hop extract comprising XN with 8|) % of diatomaeeous cardi and 20 % of hop extract (XanthoExtrakt. Honsteiner xfNT 1.7 %) was used. Beside XN. this extract also comprises a-acitis and hard resins which have an influence on the flavour. The cast wort having) a concentration)of 11.7 %w/w was fermented within 2 days by bottom fermenting brewer's yeast |and wag centrifuged after 5 days of

storage. The resulting roasted nuj|t beer (RMB) had a colour of 1850 EEC and an XN content of 390 rag/I.
Example 3
Method for preparing a roasted malt extract comprising XN according to example 1, however, the wort w$ fermented with brewer's yeast, centrifuged and tillered with diatomaeeous earth flrior to Concentration. The roasted malt beer thus prepared and having an original!'extract of 12% and a colour of approximately 1700 EBC, had an XN content 0^46 mg/1.
Bxample 4
Method for preparing a iftaisted malt beer comprising XN according to example 3, however, the RMBl'was concentrated after the filtration in vauuo (200 mbar, ca. 55 °C) to an extract content of approximately 48 %. The density of the syrup like roasted malt beer'comprising XN was approximately 1,2 kg/1, the colour was 6900 EBC, and the XN content was 846 mg/kg.
Example 5
Method for preparing a rd/isted malt extract comprising XN according ID example 1, however, an amount] (of approximately 100 mg XN per litre of won 11 i %w/w roasted malt extract! was dosed. Further treatment according to examples 3 and 4 gave a roasted] Jnalt beer with an extract content of 47 %w/\v. a density of 1.2 kg/I, a colour of 72Ju|o EBC and a XN content of 341 mg/1.

Example 6
Preparation of a coffe^ extract from 40 |g of ground roasted coffee and I litre of hot water. After separaiiion of the cofFele grounds lOOmg of a hop extract comprising XN (XN content 80 %) were added to the hot coffee extract. The hop extract was intensively mixfcd at temperatures of above 60 °C and it was further dissolved at 8 °C for 24hot[rs. After filtration of the coffee beverage comprising XN using a fluted filter the coffee beverage had an XN content of more than 12 mg/l.
Example 7
Method for preparing; a coffee bevdrage comprising XN according lo example 6, however, the filtered coffee beverage was dried in a freeze drier to a water content of less than 10 %, The soluble coffee beverage comprising XN had an XN content of 1042mg/k£.
Example 8
Approximately t.8g lof the soluble! coffee beverage comprising XN according to example 7 were- mixed with 15C(ml of hot water. The XN content tif the mixed coffee beverage W4$ approximately 10 mg/1.
Example 9
To a non-filtered pale lager beer (XN iontent 0.1 mg/1) 2 g/I of the roasted malt beer comprising XN according to exanjple 4 were added. Compared to the control beer a colour increases by 15 EBC arjd an enrichment of XN by 1.8 mg/1 were detected in the bright be£r.

Example 10
To a non-filtered pale kg# beer (XN content 0.1 mg/1) 20 g/1 of the roasted malt beer comprising XN acceding to example 4 were added. The filtered beer had a colour of 120 EEC and a JfH content of 13 mg/1.
Ex ample 11
To a filtered pale lager beejtl (XN content 0.05 mg/1) 20 g/1 of the roasted mall beer comprising XN according it example 4 were added. The mixed filtered beer had a colour of 125 EBC and an XN content of 15 mg/1.
Example 12
To a typical basic material for coke consisting of two components, coke essence, caramel colour and caffeine on the one hand, and phosphoric acid on the other hand, 880 g of a roasted riialt beer comprising XN according to example 1 (concentration 1320 mgXN/kg)"were added to 3.05kg basic coke material and homogenised. After mixing of tJie enriched basic material with processed water (3:1000), carbon dioxide (6.2 g/1) and sugar (.110 g/1) a xanthohumol content of I.I mg/1 was determined in the r^kdy-to-drink beverage.
Example 13
To one kilogram of prfjpiotic yogurt 2.29 g of roasted malt extract comprising. XN according to Sample 1 is added and homogenised. In the pasteurised product a xanthohum!c|l content of 0.3 mg/100 g was detectable,

Example 14
To a pharmaceutical pfroduct, here 1 litre of cough syrup, a roasted malt extract comprising XN (7.6 £) according to example 1 was added. The resulting product comprised approximaltely 1.0 mgXN/JOO ml.

1. Roasted Extract comprisifig xanthohumol (XN), obtainable from a. roasted
extract and a hop extract (Jomprising XN.
2. Roasted extract comprisiig XN according to claim 1, characterised in that
the roast extract includes a cold or hot extract of coarsely ground or non-
ground roasted malt, cereals, coffee or cacao.
3. Roasted extract comprisijjig XN according to anyone of claims I and 2,
characterised in that the r&asted XN extract has an XN content in the range
of'10mg/kgto2 g/kg.
4. Roasted extract comprishpig XN according to claim 3, characterised in that
has an XN content in rage of 50 mg/kg to
the roasted XN extract
1320 mg/kg, particularly to a range of 200 mg/kg to 850 mg/kg.
5. Pharmaceutical eompositfpn, characterized in that it comprises a roasted extract comprising XN acbording to anyone of claims 1 to 4.
Q. Pharmaceutical product Recording to claim 5, characterised in that the pharmaceutical composition is a cough syrup.
7. Food product, characterised in that it comprises a roasted extract comprising XN according Jo anyone of claims 1 to 4.
tS. Food product according tjcf claim 7, characterised in that the food product includes alcoholic, alcohcjl (reduced and non-alcoholic beverages.

°. Food product according to claim 8, Characterised iii that the alcoholic or alcohol reduced beverages include beferages such as spirits, herbal spirits,

herbal liqueurs, bitters

, wine, beef, or ijnixed beverages comprising beer.

10. Food product accordirfg to claim 8, .characterised in that the non-alcoholic
beverages include beverages such as Isoft drinks, coffee beverages, coffee
substitute, malt beveijages, ice tea o)r basic materials for producing the
same.
11. Food product according to claim 8, ^herein the food product comprises
bakery products, parfa^ts, dairy produces* sweets, sauces and meet products.
12. Food product accordiJiE to anyone df claims 7 to II, wherein the XN
content is 10 mg/1 to 400 mg/I, preferably from 12 mg/I to 390 mg/l, more
preferably 15 mg/1 to 2J46 mg/I.
13. Method for producing' a roasted extijact Comprising XN, wherein a hop
extract comprising X>| is mixed with |a cold or hot extract from a coarsely

ground or non-ground concentrated thereafter

roasted malt, cjereals, coffee or cacao and which is

14. Method according to cjlaim 13, wherejln the added hop extract comprising XN has a content of X$ which is in a ifange from 0.5 to 99 %w/w of XN.
15. Method according to claim 13, wherein the roasted extract comprising XN
is concentrated to dily matter of 40-50 %w/w (weight/weight percent).
particularly to 47 to 48 l%w/w.
16. Method according to c|aim 15, wherein the concentrating is performed by
evaporating, freeze drying or at reduceti pressure.

17, Method according to anyone of claims 13 to 16, wherein the roasted extract
comprising XN is fermerjt)ed by yeast and clarified.
18, Method according to cljaUrn 17, wherein the clarifying is effected by a
centrifuging or filtrating
19, Method according to anyone of claims 17 and 18, wherein the roasted malt
beer enriched with XN isj concentrated to an extract content of 40-50 %w/w
in particular to 47-48
20. Method according to clalfri 13, wherein the hop extract is pre-dissolved in ethanol for dissolving of ftie XN.
21. Method according to claifri 20, wherein the XN is dissolved by agitating,
mixing, shaking, super $>nic treatment and/or treatment with dispersing
means.
22. Method according to anyone of claims 20 and 21, characterised in that the
dissolving of xanthohurnJ4>l farther includes heating and/or the application
of an alternating current,
23. Method for producing ait aqueous extract comprising XN from roasted
products of cereals, eereaJImaltj or coffee, characterised in that:

a) tile hop product Comprising XN is added to an extract which is
mainly or completely produced from roasted or colour mall,
respectively, or roiisted barley;
b) the added hop prdauct has an XN content which, related 10 its mass
used for its production, is at least five times that of the hop used tor
its production;

c) dissolving or 4ven an intensive dissolving of XN is achieved after the addition c|f the hop product comprising XN to the aqueous roasted extract despite the ojriginally low solvability in aqueous solutions; |

d) dissolving is
comprising X>
e) dissolving of

promoted by jpre-dissolving of the hop product in ethanol; ' XN is prorno[ted by agitating, mixing, shaking.

supersonic treatment, Ultratura* treatment or any other mechanical forces;
f) dissolving of XJN is promoted fy heating of the roasted extract;
g) dissolving of XJN is promoted |y applying an alternating current;
h) the amount of ^acution ot the rjop product comprising XN is at least 50mgofXNp|erlitre.
24. Method for producing the roasted ejxtract comprising XN according to
claim 23, further characterised in thjat the extract enriched with XN is
concentrated to a dry rrtatter ot approximately 50 %.
25. Method for producing) the roasted extract comprising XN according tci
claim 23, further charatterised in that

a) the extract enriched with XN |s fermented by yeast, centrifuged or
filtered;
b) the roasted rriald beer enriched with XN is concentrated to an extract
content of e.g. 30 %.
26.. Method for producing the extract comprising XN according to anyone of claims 23 to 25, fiirtHo" characterisdd in that a commercially available roasted rrialt extract and a commercially available roasted malt beer is used for dissolving the hop ektract enriched [with XN.

27. Method for producing $ roasted extract comprising XN according to
anyone of claims 23 and 2H further characterised in that an extract from the
commercially available rested coffee and from the commercially available
instant coffee is used for Dissolving this hop extract enriched with XN.
28. Roasted extract comprisnjig xanthohumol with an XN content of more than
10 mg/kg which is produced according to anyone of claims 23 to 27,
wherein the use of this expect is intended for the natural enrichment of XN
in beverages such as beet' mixed beverages comprising beer, wine, coffee
beverages, coffee substitute or another non-alcoholic beverage or u
precursor of these product!
29. Roasted extract comprisuji^ xanthohumol with an XN content of more than
! 0 mg/kg which is produced according to anyone of claims 23 to 27,
wherein the use of thSi extract is intended for the production of
xanthohumol comprising jb^akery products, parfait, desserts, ice cream, meal
products, sauces, and similar products or a precursor of these products.
30. Roasted extract oomprisiit xanthohumol with an XN content of more thun

50 mg/kg which is produc

ed according to anyone of claims 23 to 27.

31. Roasted extract cdmprisiihfc xanthohumol with an XN content of more than
200 mg/kg which is prodiitfed according to anyone of claims 23 to 27.
32. Roasted extract cornprisii^ xanthohumol with an XN content of more than
200 mg/kg.

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Patent Number

271308

Indian Patent Application Number

962/DELNP/2007

PG Journal Number

08/2016

Publication Date

19-Feb-2016

Grant Date

16-Feb-2016

Date of Filing

05-Feb-2007

Name of Patentee

TA-XAN AG

Applicant Address

ADOLFSALLEE 21, 65185 WIESBADEN (DE)

Inventors:

#	Inventor's Name	Inventor's Address
1	BACK, WERNER	AN DER MÜHLE 9A 85354 FREISING DE
2	ZÜRCHER, ACHIM	THEOPHIL-RONIGER-STRASSE, 4310 RHEINFELDEN (CH)
3	WUNDERLICH, SASCHA	KöRNERSTRASSE 21, 85354 FREISING (DE)

PCT International Classification Number

A61K 31/12

PCT International Application Number

PCT/EP2005/013916

PCT International Filing date

2005-12-22

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	10 2004 063 125.5	2004-12-22	Germany