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(12) United States Patent (10) Patent No.: US 8,623.429 B2 Eidenberger (45) Date of Patent: Jan

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(12) United States Patent (10) Patent No.: US 8,623.429 B2 Eidenberger (45) Date of Patent: Jan USOO8623429B2 (12) United States Patent (10) Patent No.: US 8,623.429 B2 Eidenberger (45) Date of Patent: Jan. 7, 2014 (54) STABILIZED ANTHOCYANN 2002fOO18821 A1 2, 2002 Soulier et al. COMPOSITIONS 2003/0027747 A1 2, 2003 Yatcilla et al. 2007/0O31517 A1 2/2007 Matar et al. 2007/0082064 A1 4/2007 Krawitz (71) Applicant: Omnica GmbH, Hamburg (DE) 2008/0255226 A1 10/2008 Eidenberger (72) Inventor: Thomas Eidenberger, Steyr (AT) FOREIGN PATENT DOCUMENTS (73) Assignee: Omnica GmbH, Hamburg (DE) EP 1474.999 4/2004 JP 2001211858 A 8, 2001 (*) Notice: Subject to any disclaimer, the term of this JP 20033.06446 A 10, 2003 JP 2006.306820 A 11, 2006 patent is extended or adjusted under 35 JP 20073O8396 A 11, 2007 U.S.C. 154(b) by 0 days. WO WO92/03146 3, 1992 (21) Appl. No.: 13/801,175 OTHER PUBLICATIONS (22) Filed: Mar 13, 2013 "Agrinine/Blueberry Extract/Fumaric Acid/Glycine/L-Carnitine/L- (65) Prior Publication Data Cysteine/Lettuce Extract/Ornithine/Vitamin B12/Vitiamin B5 (Cal cium Pantothenate)/Vitamin b6/Vitamin C/Zinc Sulfate', accessed US 2013/0210908A1 Aug. 15, 2013 via www.idruginfo.com, Sep. 17, 2013, 4 pages. "Blueberries, raw'. Self Nutrition Data, Know What You Eat, Related U.S. Application Data accessed via http://nutritiondata. Self.com/facts.fruits-and-juices/ (63) Continuation-in-part of application No. 13/442.455, 1851/2, Sep. 13, 2013, 2 pages. filed on Apr. 9, 2012, now Pat. No. 8,449,927, which is Maccarone, Emanuele et al., "Stabilization of Anthocyanins of Blood a continuation of application No. 12/825,546, filed on Orage Fruit Juice', vol. 50, (1985), Journal of Food Science, pp. Jun. 29, 2010, now Pat. No. 8,153,168, which is a 901-904, XP002516584. continuation of application No. 12/047.993, filed on Vaimakis V., et al., “Must oxygenation Together with Gluatathlone Mar. 13, 2008, now Pat. No. 7,820,207. Addition in the Oxidation of WhiteWine:”, Food Chem., vol. 57, No. 3, (1996), pp. 419-422, XP002516585. (60) Provisional application No. 60/895,034, filed on Mar. Mary Ann Lila, “Anthocyannis and Human Health: AN In Vitro 15, 2007, provisional application No. 60/952,113, Investigative Approach'. Journal of Biomedicine and Biotechnology, filed on Jul. 26, 2007, provisional application No. (2004):5, p. 306–313. 60/985,603, filed on Nov. 5, 2007. Talavera, Severine et al., Anthocyannis are Efficiently Absorbed from the Small Intestine in Rats: Apr. 2004, American Society for Nutri (51) Int. C. tional Sciences, Nutrient Metabolism, pp. 2275-2279. AOIN 65/00 (2009.01) Taulavouri, et al. Plant Biol. No. 1, 1999, pp. 187-191. (52) U.S. C. Talavera, Severine et al., “Anthocyanins are Efficiently Absorbed USPC .......................................................... 424f725 from the Stomachin Anesthetized Rats', Jul. 2003, American Society (58) Field of Classification Search for Nutritional Sciences, Nutrient Metabolism, pp. 4178-4182. None Marco, Paulo H. et al., “Exploratory Analysis of Simultaneous Deg See application file for complete search history. radation in the Calyces of Flowers of the Hibiscus sabdarifa Species by PARAFAC Model”. Analytical Sciences, The Japan Society for (56) References Cited Analytical Chemistry, Dec. 2005, vol. 21, pp. 1523-1527. U.S. PATENT DOCUMENTS (Continued) 4,211,577 A 7, 1980 Wallin 4,268,265 A 5/1981 Von Wattenwyl Primary Examiner — Michael Meller 4,302,200 A 11/1981 Yokoyama et al. 5,008, 110 A 4, 1991 Benecke et al. (74) Attorney, Agent, or Firm — Fulbright & Jaworski, LLP: 5,087,240 A 2, 1992 Sibalis Scott D. Rothenberger 5,088,977 A 2, 1992 Sibalis 5,163,899 A 11, 1992 Sibalis 5,164,189 A 11/1992 Farhadieh et al. 5,200, 186 A 4, 1993 Gabetta et al. (57) ABSTRACT 5,254,346 A 10, 1993 Tucker et al. 5,290,561 A 3, 1994 Farhadieh et al. The invention describes stabile anthocyanin compositions, 5,332,213 A 7, 1994 Klose methods to prepare Such compositions and also methods of 5,336,168 A 8, 1994 Sibalis use of Such compositions to treat various afflictions. The 5,352,456 A 10, 1994 Fallon et al. 5,407,713 A 4/1995 Wilfong et al. present invention describes unique compositions of an antho 5,817,354 A 10, 1998 Mozaffar et al. cyanin and a stabilizing compound Such that the combination 5,912,363 A 6/1999 Nafisii-Movaghar et al. of the two components provides that the anthocyanin does not 5,925,620 A 7/1999 Ohlenschlager et al. 6,171,602 B1 1/2001 Roman readily undergo degradation, such as oxidation, pH instabil 6,569,446 B1 5, 2003 Howard ity, etc. 6,818,234 B1 1 1/2004 Nair et al. 7,820.207 B2 10/2010 Eidenberger 2001/0031744 A1 10, 2001 KOsbab 8 Claims, 28 Drawing Sheets US 8,623.429 B2 Page 2 (56) References Cited Kader, et al., “Degradation of Cyanidin 3-Glucoside by Blueberry Polyphenol Oxidase: Kinetic Studies and Mechanisms”. J. Argic OTHER PUBLICATIONS Food Chem, vol. 46, 1998, pp. 3060-3065. Japanese Office Action dated Apr. 16, 2013 from related Japanese Cash, et al., “Characteristics of Concord Grape Polyphenoloxidase application JP2009-553240, 4 pages. Involved In Juice Color Loss”. J. Food Sci, 1976, vol. 41, pp. 1398 Koki, et al., Folia Pharmacol. Jpn., 20002, No. 116, Suppl 1, 7P-15P. Siddiq, et al., “Effect of Polyphenol Oxidation and its Inhibitors on 1402. Anthocyanin Changes. In Plum Juice'. Journal of Food Processing International Search Report from related PCT Application PCT/ and Preservation, 1994, vol. 18, No. 1, pp. 75-84. IB2008/003279 dated Mar. 23, 2009, 3 pages. Skrede, et al., “Changes in Anthocyanins and Polyphenolics During International Preliminary Report on Patentability from related PCT Juice Processing of Highbush Blueberries (Vaccinium corymbosum Application PCT/IB2008/003279 dated Sep. 15, 2009, 7 pages. L.)”, Journal of Food Science, vol. 65, No. 2, 2000, pp. 357-364. U.S. Patent Jan. 7, 2014 Sheet 1 of 28 US 8,623.429 B2 Figure 1 Lack of bathochromic shift for cy-3-O-glucoside (1 mMolar solution) lamdamax of 10-3 M solutions at different pH a - a as None a ra ' DHA or Gutath Figure 2 Lack of hyperchromic shift for cy-3-O-glucoside (1 mMolar solution) Absorption of 10-3 M solutions at different pH - as a -- a None as a DHA - Glutath U.S. Patent Jan. 7, 2014 Sheet 2 of 28 US 8,623.429 B2 Figure 3 % residual anthocyanosides of bilberry extract (unprotected) 120 ----------------------------------------------------------------- Figure 4 % residual anthocyanosides of bilberry extract (DHLA protected) 60 minutes at room temperature (DHA) 120 :- so e o O.O. M. ex x OOOM was OOOO M U.S. Patent Jan. 7, 2014 Sheet 3 of 28 US 8,623.429 B2 Figure 5 % residual anthocyanosides of bilberry extract (GSH protected) 60 minutes at room temperature (Glutathione) Figure 6A through 6D Comparative degradation kinetics of bilberry extract (DHA-protected) Figure 6A Figure 6B pr1.0 pH-3. S} l 50 200 S st 50 208 S 300 time (r)in time (ifyin) A&Noe : A&Noia U.S. Patent Jan. 7, 2014 Sheet 4 of 28 US 8,623.429 B2 Figure 6C Figure 6D pit 7.0 ph9.0 2.478.0 x y - i. 18425-908 Ab R. s. O. 97.3 R - 0.9972 S. 56 2. 1.5 y r -0.0037x -- .2888 y s -O,OO25x + i. 977 R - 0.993.3 Rs: 0.9566 O5 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -------------------------------------- 1 50 O SO 20 250 300 O 5 OO 50 200 250 300 time (min) Time (min) i DihLA 8 None - Linear (None)- Exponent.ie (DHA) DHA & None-leaf (None)- Exonertie (DHLA) Figure 7 Comparative degradation kinetics of delphinidin-3-O-galactoside Delp.-Galac. 800 y = 695.02e x R = 0.8142 4.O O - 1623X -- 575,4 100 R = 0.857. O -------------------------------------------------------------------------------------------------------- OOO 50,00 100.00 150,00 200,00 250,00 300.00 Time (h) --------------------------------------------------------------------------------------------------------------------------------------------------------e None & Glutathione - Exponentie: (Glutathione) - Linear (None) U.S. Patent Jan. 7, 2014 Sheet 5 of 28 US 8,623.429 B2 Figure 8 Comparative degradation kinetics of petunidin-3-O-galactoside Petu.-Galac. 310 y = 226,45e'''* 260 R = 0.7124 210 3. 5 60 3 110 < 60 - y = - 0.44:4x + 192,02 OOO 5OOO OOOC 50.OO 200.00 250.OO 3OOOO Time (h) e None & Glutathione -Linear (None) - Exponentie: (Glutathione) Figure 9 Comparative degradation kinetics of delphinidin-3-O-galactoside Cyan.-Galac. 600 y - 474.77e9.9996* - 500 & 8 R 2 is- 0,556. : 400 ; 2 a 300 e S. 200 y = - 0.6286x + 416.46 100 * = 0.6427 O i.-------------------------------------------------------------------------------------------------------------------------- 0.00 SO.OO 100.00 50.00 20000 250,00 300.00 Time (h) 0. None & Glutathione - Exponentie: (Glutathione) - Linear (None) U.S. Patent Jan. 7, 2014 Sheet 6 of 28 US 8,623.429 B2 Figure 10 Comparative degradation kinetics of cyanidin-3-O-galactoside (red line... unprotected, blue line. GSH protected) Degradation of Cyanidin-3-O-Galactoside re - - - - $ 80 : 9 N. s 60 - s8 5, Y A 40 N 20 ^ O -:----------------------------------------------------------------1----------------------------------------------------------A. O. O. 0. O OO Time log (h) U.S. Patent Jan. 7, 2014 Sheet 7 of 28 US 8,623.429 B2 Figure 11 Comparative degradation of 15 bilberry anthocyanosides (DHLA protected) 100 for A. O 20 - Figure 12 Comparative degradation of 5 bilberry anthocyanosides (GSH protected) 100 : 80 60 40 20 (p (p i g O l 8: Unprotected 8 Glutathione-protected U.S. Patent Jan. 7, 2014 Sheet 8 of 28 US 8,623.429 B2 Figure 13 Stability in buffered solution Stability of lead-anthocyanosides (Black Currant) in presence of glutahione at pH 7.0 and 37 °C (buffer solution) O 20 40 6C 8O OO 120 Time (h) • a sw w x Op-Glc - Dp-Rut..
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