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(12) United States Patent (10) Patent No.: US 8.449,927 B2 Eidenberger (45) Date of Patent: May 28, 2013

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(12) United States Patent (10) Patent No.: US 8.449,927 B2 Eidenberger (45) Date of Patent: May 28, 2013 USOO8449927B2 (12) United States Patent (10) Patent No.: US 8.449,927 B2 Eidenberger (45) Date of Patent: May 28, 2013 (54) STABILIZED ANTHOCYANN 5,912,363 A 6/1999 Nafisii-Movaghar et al. COMPOSITIONS 5,925,620 A 7/1999 Ohlenschlager et al. 6,171,602 B1 1/2001 Roman 6,569,446 B1 5/2003 Howard (75) Inventor: Thomas Eidenberger, Steyr (AT) 6,818,234 B1 1 1/2004 Nair et al. 7,820.207 B2 10/2010 Eidenberger (73) Assignee: Omnica GmbH, Hamburg (DE) 2001/0031744 A1 10, 2001 KOsbab 2002fOO18821 A1 2/2002 Soulier et al. Notice: Subject to any disclaimer, the term of this 2003/0027747 A1 2/2003 Yatcilla et al. (*) 2007/0O31517 A1 2/2007 Matar et al. patent is extended or adjusted under 35 2007/0082064 A1 4/2007 Krawitz U.S.C. 154(b) by 0 days. 2008/0255226 A1 10/2008 Eidenberger (21) Appl. No.: 13/442,455 FOREIGN PATENT DOCUMENTS EP 1474.999 4/2004 (22) Filed: Apr. 9, 2012 WO 92/03146 3, 1992 (65) Prior Publication Data OTHER PUBLICATIONS US 2012/0277173 A1 Nov. 1, 2012 Taulavuori et al., Plant Biol. 1, 1999, 187-191.* Maccarone, Emanuele et al., "Stabilization of Anthocyanins of Blood Related U.S. Application Data Orange Fruit Juice', vol. 50, (1985), Journal of Food Science, pp. 901-904, XP002516584. (63) Continuation of application No. 12/825,546, filed on Vaimakis V., et al., “Must oxygenation Together with Gluatathlone Jun. 29, 2010, now Pat. No. 8,153,168, which is a Addition in the Oxidation of WhiteWine. Food Chem, vol. 57, No. continuation of application No. 12/047.993, filed on 3, (1996), pp. 419-422, XP0025 16585. Mar. 13, 2008, now Pat. No. 7,820,207. Mary Ann Lila, “Anthocyannis and Human Health: AN In vitro Investigative Approach'. Journal of Biomedicine and Biotechnology, (60) Provisional application No. 60/895,034, filed on Mar. (2004):5, pp. 306–313. 15, 2007, provisional application No. 60/952,113, Talavera, Severine et al., Anthocyannis are Efficiently Absorbed from filed on Jul. 26, 2007, provisional application No. the Small Intestine in Rats: Apr. 2004, American Society for Nutri 60/985,603, filed on Nov. 5, 2007. tional Sciences, Nutrient Metabolism, pp. 2275-2279. Talavera, Severine et al., “Anthocyanins are Efficiently Absorbed (51) Int. C. from the Stomachin Anesthetized Rats', Jul. 2003, American Society AOIN 65/00 (2009.01) for Nutritional Sciences, Nutrient Metabolism, pp. 4178-4182. (52) U.S. C. Marco, Paulo H. et al., “Exploratory Analysis of Simultaneous Deg USPC .......................................................... 424f725 radation in the Calyces of Flowers of the Hibiscus Sabdariffa Species (58) Field of Classification Search by PARAFAC Model”. Analytical Sciences, The Japan Society for None Analytical Chemistry, Dec. 2005, vol. 21, pp. 1523-1527. See application file for complete search history. * cited by examiner (56) References Cited Primary Examiner — Michael Meller U.S. PATENT DOCUMENTS (74) Attorney, Agent, or Firm — Scott D. Rothenberger; 4,211,577 A 7, 1980 Wallin Fulbright & Jaworski L.L.P. 4,268,265 A 5/1981 Von Wattenwyl 4,302,200 A 11/1981 Yokoyama et al. ABSTRACT 5,008, 110 A 4, 1991 Benecke et al. (57) 5,087,240 A 2, 1992 Sibalis The invention describes stabile anthocyanin compositions, 5,088,977 A 2, 1992 Sibalis methods to prepare Such compositions and also methods of 5,163,899 A 11, 1992 Sibalis 5,164,189 A 11/1992 Farhadieh et al. use of Such compositions to treat various afflictions. The 5,200, 186 A 4, 1993 Gabetta et al. present invention describes unique compositions of an antho 5,254,346 A 10, 1993 Tucker et al. cyanin and a stabilizing compound Such that the combination 5,290,561 A 3, 1994 Farhadieh et al. of the two components provides that the anthocyanin does not 5,332,213 A 7, 1994 Klose 5,336,168 A 8, 1994 Sibalis readily undergo degradation, such as oxidation, pH instabil 5,352,456 A 10, 1994 Fallon et al. ity, etc. 5,407,713 A 4/1995 Wilfong et al. 5,817,354 A 10, 1998 Mozaffar et al. 4 Claims, 27 Drawing Sheets U.S. Patent May 28, 2013 Sheet 2 of 27 US 8.449,927 B2 Figure 3 % residual anthocyanosides of bit berry extract (unprotected) 60 minutes at roorn tenperature (None) 2 s e O. is as O. v is O. M. Figure 4 % residual anthocyanosides of bilberry extract (DHLA protected) 60 rinutes at roor temperature (Ohil A) Šs: 888 X see is . so be O so U.S. Patent May 28, 2013 Sheet 3 of 27 US 8.449,927 B2 rigires & resid:8 at 8:y&88sixes of 8:88-y extract 38: protectex & x::::::::::::: *xxxix: ::::::::::::::::::::::::::::::::::::::::: .g. y y' & & 8 a.s.. ." & 8 x 3.38.8 * * x re isssssssssssssssssssssssssssss 3. 8 & 8 kx ::::: 8 x x 8.3:3: 8: x:33:33:38 Fig.ire & through 8:3 {{3:33:8:w: tieg'8:a:::::: x:3:x: {}f 8:8-y 8x838 (38.8-3-8:8:::::: *g are A *igre 88. 8x3.8 $883.3 ---------------------------------------------------------------------------------------------------- U.S. Patent May 28, 2013 Sheet 7 Of 27 US 8.449,927 B2 *igre . 8.83.388.88: 888.8 x8:38: figures 2 8. : & & s y's 8:3::::::::::::8x: 8:3::::::::::88-8:::::::::::::: U.S. Patent May 28, 2013 Sheet 10 of 27 US 8.449,927 B2 Figare 38 S S S S : s 83:8: : U.S. Patent May 28, 2013 Sheet 12 of 27 US 8.449,927 B2 figure is: ::::s:x:33:3::::::::::::: ----------------------------------------------------------------------------Y-------------. 3:8:&&. --88:a & --... 8388x3:wa : 3 : 3 8 8 & '88: 8: figure 28 3: *:::::::::::::::::::::::::::::::::: 883 . -------------------- 8. 8:3 s: &8 is 8. : :::::::: U.S. Patent May 28, 2013 Sheet 13 Of 27 US 8.449,927 B2 * is: 8 23. 8.::::::::::::::::::: :::::::: {}i 388 :*>. **** s: :*... g.: 8 :::::: $3 &:::::: ------------------------------. wr-------------------------------------------------- 8. U.S. Patent May 28, 2013 US 8.449,927 B2 *************& 8: 8-8-*-Ws....: U.S. Patent May 28, 2013 Sheet 16 of 27 US 8.449,927 B2 8-xxxx $3:3: 8::::::::::y www. :: s: : 3.SS sees is 38 388 , -: , s: - - 8: & M. :8 U.S. Patent May 28, 2013 Sheet 18 of 27 US 8.449,927 B2 :*ig ire 3 exte: 88sixir (x:::::::::::::: 8:8; y - $3:xerry; Cyst8:8 cc 88 :::::::::::: U.S. Patent May 28, 2013 Sheet 19 Of 27 US 8.449,927 B2 fig:8 3: 388: 8::::::::::::::::::$88 8:88 y - 8:38:rry; Cy:88 ::::::x: ::::: as s as SS 33 : s 8. s S-- : 83. : U.S. Patent May 28, 2013 Sheet 20 Of 27 US 8.449,927 B2 *igate 32 8:: : 8:3 : 8. 88: 38 8. &ry-8: ::::: U.S. Patent May 28, 2013 Sheet 22 of 27 US 8.449,927 B2 w 3. 88: 8 8 :: 8:: :88: 8. 8 8.3:8:8: ::3:38 U.S. Patent May 28, 2013 Sheet 23 Of 27 US 8.449,927 B2 fig:: 388 :::::::... 8.3:33:8: 83.3888 & 3.3% fata: C &ixerry 83 8. 3 8 3. 8 : * : *:::::::: 3 one ... a 3x3; 3 xx:33y *igi: 3:38 fata: C (8iiiety f(ysteite txatics : is: X is 33s 3 sex r $33, 8 rex 333 : U.S. Patent May 28, 2013 Sheet 24 of 27 US 8.449,927 B2 *igise 3 & {}: 83,333.38: fatai tph (8ixerry : w X-XXixXx: ise {} {33y : W -- 33 3 MM. 33 3 *g:re 338 fotai top (Biiixerryf cysteine corrbo ex m s w U.S. Patent May 28, 2013 Sheet 25 Of 27 US 8.449,927 B2 *ig.:8: 388. 88:88): 3888::::: fatai at 8i xerry : &a---3. figure 388 fotai tsiiseryf cysteine corribe : U.S. Patent May 28, 2013 Sheet 26 of 27 US 8.449,927 B2 *:::::: 3:38. 8:338:... :::::::::::::::::::::: fotai pe (Biterry Y Y Y Y Y Y : Y Y Y Y Y Y Y {}. 33 y : - -3-33s. 4 re--a 38 y : fig338 388 foxtai e Biberry cysteine cannix is w X-33s 4 xx 8s 3 U.S. Patent May 28, 2013 Sheet 27 Of 27 US 8.449,927 B2 *ig ire 88& $3:33.8:83.333333: $3.8883: .3:x: {&:8::... 8:8. fatai Kw Biberry Ya -------.38-3-8X-------------------&-,' & 's' & 3. - gtai Kw Biery fysteine certist US 8,449,927 B2 1. 2 STABILIZED ANTHOCYANN six basic anthocyanin compounds predominate, differing COMPOSITIONS both in the number of hydroxyl groups present on the carbon ring and in the degree of methylation of these hydroxyl CROSS REFERENCE TO RELATED groups. The identity, number and position of the Sugars APPLICATIONS attached to the carbon skeleton are also variable; the most common Sugars that can be linked to carbon-3, carbon-5 and, This application is a Continuation of U.S. patent applica Sometimes, carbon-7, are glucose, arabinose, rhamnose or tion Ser. No. 12/825,546 filed Jun. 29, 2010, now U.S. Pat. galactose. On this basis, it is possible to distinguish mono No. 8,153,168, issued Apr. 10, 2012, which is a Continuation sides, biosides and triosides. of U.S. patent application Ser. No. 12/047,993, filed Mar. 13, 10 Another important variable that contributes to the chemical 2008, which is U.S. Pat. No. 7,820,207, issued Oct. 26, 2010, structure of anthocyanins is the acylating acid that can be which claims benefit of U.S. Ser. No. 60/895,034 filed on present on the carbohydrate moiety. The most frequent acy Mar.
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