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(12) United States Patent (10) Patent No.: US 8,512,790 B2 Abelyan Et Al

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(12) United States Patent (10) Patent No.: US 8,512,790 B2 Abelyan Et Al US008512790B2 (12) United States Patent (10) Patent No.: US 8,512,790 B2 Abelyan et al. (45) Date of Patent: *Aug. 20, 2013 (54) HIGH-PURITY REBAUDIOSIDE DAND (56) References Cited LOW-CALORE CHOCOLATE CONTAINING THE SAME U.S. PATENT DOCUMENTS 3,723.410 A 3, 1973 Persinos (75) Inventors: Varuzhan Abelyan, Kuala Lumpur 1985 A r 3. RatSushita f al. et al.al Numpur (MY);s YES, Lidia Abelyan, S. Kuala1 4,599.4034,361,697 A 1 7/19861/1982 KumarDobberstein et al. Lumpur (MY) 4,892,938 A 1/1990 Giovanetto 5,112,610 A 5/1992 Kienile (73) Assignee: Psycircle Sdn Bhd, Negeri Sembilan 5,972,1205,962,678 A 10/1999 PayzantKutowy et al. ( ) 6,031,157 A 2/2000 Morita et al. 6,080,561 A 6/2000 Morita et al. (*) Notice: Subject to any disclaimer, the term of this 2006/0083838 A1 4/2006 Jackson et al. patent is extended or adjusted under 35 2006/0134292 A1 6/2006 Abelyan et al. U.S.C. 154(b) by 393 days. (Continued) This patent is Subject to a terminal dis- FOREIGN PATENT DOCUMENTS claimer. CN 101.200480 A 6, 2008 JP 520O5800 A 1, 1977 (21) Appl. No.: 12/785,507 (Continued) OTHER PUBLICATIONS (22) Filed: May 24, 2010 Kovylyaeva, G.i., Bakaleinik, G.A., Strobykina, I.Y. Gubskaya, V.I., O O Sharipova, R.R., Alfonsov, V.A., Kataev, V.E., and Tolstikov, A.G. (65) Prior Publication Data 2007. Glycosides from Stevia rebaudiana. Chemistry of Natural US 2011 FOO91637 A1 Apr. 21, 2011 Compounds. V.43, No. 1, 81-85. (Continued) Related U.S. Application Data Primary Examiner — Humera Sheikh (63) Continuation-in-part of application No. 12/580,233, Assistant Examiner — Subbalakshmi Prakash filed on Oct. 15, 2009, now Pat. No. 8,299,224. (74) Attorney, Agent, or Firm — Pyprus Pte Ltd (57) ABSTRACT (51) Int. Cl. The invention provides methods of purifying Rebaudioside D A2.3L I/236 (2006.01) from the Stevia rebaudiana Bertoni plant extract along with A23G L/00 (2006.01) Rebaudioside A. The methods are useful for producing high (52) U.S. Cl. purity Rebaudioside D and Rebaudioside A. The invention USPC ........................................... 426/548; 426/593 further provides a low-calorie chocolate containing the puri (58) Field of Classification Search fied Rebaudioside Danda process for making the low-calorie None chocolate containing the purified Rebaudioside D. See application file for complete search history. 11 Claims, 11 Drawing Sheets Compound name R(C-19) R(C-3) Stevil H H 2. Stevion onside B-Gic 3. Rubusoside f-Glc (-Glc 4. Stewiolbioside H -Glc-B-Glc{2p) 5, Stewigside -Glc 3-Glc-6-Glc(21) 6. Rebaudioside A B-Gle B-&loc31)3-Glc-8-Glc(21) 7. Rebatidioside B H B-Glc-f-Glc2-1) B.Glcis) 8. Rebaudioside C B-Glc 3-Glc-a-Rha(21) Dulcoside B) B-d?c(3di) 9. Rebaudioside D B-Glc-f-Glc2-1) B-Glc-i-Glc25) Gc(3-1) 0. Rebaudioside E p-Glcs-Glco's 1) f-Glc-f-Glc25) 1. Rebaudiosid: F -Glc p-qi-6-Xyl(291) g-Glc(31) 12. Dulcoside A B-Gic (3-Glc-a-Rha(291) US 8,512,790 B2 Page 2 (56) References Cited Starrett, A.N., Kirbi, C.W., Pocs, R., and Brandle J.E. 2002. Rebaudioside F, a diterpene glycoside from Stevie rebaudiana. U.S. PATENT DOCUMENTS Phytochemistry. V.59, 367-370. 2006/O142555 A1 6/2006 Jonnala et al. Kobayashi, M., Horikawa, S., Dergandi, I.H., Ueno, J., and 2007/0082103 A1* 4/2007 Magomet et al. ............. 426,548 Mitsuhashi, H. 1977. Dulcoside A and B, New diterpene glycosides 2007/01 16825 A1 5/2007 Prakash et al. ................ 426,548 from Stevia rebaudiana. Phytochemistry. V/16. 1405-1408. 2007,0292582 A1 12, 2007 Prakash et al. Shi, R., Xu, M., Shi, Z. Fan, Y. Guo, X. Liu, Y. Wang, C., and He, 2008/0300402 Al 12/2008 Yang et al. B. 2002. Synthesis of bifunctional polymeric adsorbent and its appli cation in purification of Stevia glycosides. Reactive & Functional FOREIGN PATENT DOCUMENTS Polymers. V.50. 107-116. JP 5208.3731 A 7/1977 Chen, T. Zhang, Y. Liu, X., Shi, Z., Sun, J. and He, B. 1998. Science JP 52100500 A 8, 1977 in China. V.41. No. 4. 436-441. JP 52136200 A 11, 1977 Chen, T. Zhang, Y. Liu, X., Shi, Z., Sun, J. and He, B. 1999. Science JP 54030199 A 3, 1979 in China. V.42. No. 3. 277-282. JP 54132599 A 10, 1979 JP 55039731 A 3, 1980 Fuh, W-S., Chiang, B-H. 1990. Purification of Steviosides by mem JP 55081567 A 6, 1980 brane and ion exchange process. Journal of Food Science. V.55. No. JP 55092400 A T 1980 5. 1454-1457. JP 5512O77O A 9, 1980 Zhang, S.O., Kumar, A., Kutowy, O. 2000. Membrane-based sepa JP 55138372 A 10, 1980 ration scheme for processing Sweetener from Stevia leaves. Food JP 55 15977O A 12, 1980 Research international. V.33. 617-620. JP 55162953. A 12, 1980 Liu, Y. Yiming, C., Lining, W., and J.Jianhua. 1991. Study of JP 56.099768 A 8, 1981 Stevioside preparation by membrane separation process. Desalina JP 56109568 A 8, 1981 tion. V.83. 375-382. JP 56121453. A 9, 1981 Chen, T. Zhang, Y. Liu, X., and He, B. 1999. Studies on the adsorp JP 56121454. A 9, 1981 JP 56121455. A 9, 1981 tive selectivity of the polar resin with carbonyl group on rebaudioside JP 56160962 A 12/1981 A. Acta Polymeric Scnica. No. 4.398-403. JP 57002656 A 1, 1982 Moraes, E., Machado., N.R. 2001. Clarification of Stevia rebaudiana JP 57.005663 A 1, 1982 (Bert.) Bertoni extract by adsorption in modified zeolites. Acta JP 57046998 A 3, 1982 Scientiarum. V.23. No. 6. 1375-1380. JP 57075.992 A 5, 1982 Montovaneli, I.C.C., Ferretti, E.C., Simxes, M.R., and C. Silva. 2004. JP 57086264. A 5, 1982 The effect of temperature and flow rate on the clarification of the JP 58O28246 A 2, 1983 aqueous Stevie-extract in fixed-bed column with zeolites. Brazilian JP 58O28247 A 2, 1983 Journal of Chemical Engineering. V.21. No. 3. 449-458. JP 58212759. A 12, 1983 Pol, J., Ostra, E.V. Karasek, P., Roth, M., Benesova, K. Kotlarikova, JP 58212760. A 12/1983 P, and J.Caslaysky, 2007. V.388. 1847-1857. JP 59045848 A 3, 1984 JP 62166861 A 7, 1987 Bandna, V.J., Singh, B., and V.K.Kaul. 2009. An efficient microwave JP 631 73531 A T 1988 assisted extraction process of Stevioside and rebaudioside A from JP 1131191 A 5, 1989 Stevia rebaudiana (Bertoni). Phytochemical Analysis. V.20.240-245. JP 06007108 A 1, 1994 Teo, C.C., Tan, S.N., Yong, J.W.H., Hew, C.S., and E.S.Ong. 2009. JP 6192283 A T 1994 Validation of green-solvent extraction combined with chromato JP T143860 6, 1995 graphic chemical fingerprint to evaluate quality of Stevie rebaudiana JP 7177862 A 7, 1995 Bertoni. J. Sep.Sci. V.32. 613-622. JP 8000214. A 1, 1996 Yoda, S.K., Marques, M.O.M., Ademir J. Petenate, A.J., and M. A. JP 2002262822 A 9, 2002 Meireles. 2003. Supercritical fluid extraction from Stevia rebaudiana OTHER PUBLICATIONS Bertoni using CO2 and CO2+water: extraction kinetics and identifi cation of extracted components. Journal of Food Engineering. V.57. Kohda, H., Kasai, R., Yamazaki, K., Murakami, K., and Tanaka, O. 125-134. 1976. New Sweet diterpene glucosides from Stevia rebaudiana. Phytochemistry. V. 15,981-983. * cited by examiner U.S. Patent Aug. 20, 2013 Sheet 1 of 11 US 8,512,790 B2 Compound name R (C-19) R(C-13) 1. Steviol H 2. Steviolmonoside (3-Glc 3. Rubusoside f3-Glc 4. Steviolbioside (3-Glc-3-Glc(2) I) 5. Stevioside (3-Glc-f-Glc(21) 6. Rebaudioside A B-gic-f-Glc(291) B-Glc(3-1) 7. Rebaudioside B p-Glc-f-Glc(2-1) (3-Glc(31) B-Glc 8. Rebaudioside C B-Glc-a-Rha(2-1) (Dutcoside B) (3-Gic(3-1) 9. Rebaudioside D (3-Glc-B-Glc(21) B-Glc-f-Glc(2-1) f-Glc(3> 1) (). Rebaudioside E (3-Glc-f-Glc(21) f3-Glc-f-Glc(2-1) 1. Rebaudioside F P-Glc B-Glc-f-Xyl(2-1) (3-Glc(31) 12. Dulcoside A (3-Glc (3-Glc-O-Rha (2x1) FIG 1 U.S. Patent Aug. 20, 2013 Sheet 2 of 11 US 8,512,790 B2 Stevioside FIG 2 U.S. Patent Aug. 20, 2013 Sheet 3 of 11 US 8,512,790 B2 HOH OH OH OH Rebaudioside A Rebaudioside B FEG 20Oont'd) U.S. Patent Aug. 20, 2013 Sheet 4 of 11 US 8,512,790 B2 O O CHOH O OH OH OH Rebaudioside D FIG 2 (Cont'd) U.S. Patent Aug. 20, 2013 Sheet 5 of 11 US 8,512,790 B2 Rebaudioside E FIG 2 (Cont'd) U.S. Patent Aug. 20, 2013 Sheet 6 of 11 US 8,512,790 B2 CHOH O O OH Rebaudioside F HOH OH OH OH Dulcoside A FIG 2 (Cont'd) U.S. Patent Aug. 20, 2013 Sheet 7 of 11 US 8,512,790 B2 e=o OH Steviolbioside HOH O HO O, HO , 2CH2 Rubusoside FG 2 (Cont'd) U.S. Patent Aug. 20, 2013 Sheet 8 of 11 US 8,512,790 B2 Stevia Extract - Absolute ethanol: - Water, - Heating, - Complete dissolving; - Cooling, - Starter of Rebaudioside A: - Aging: - Heating: - Cooling: - Aging, Suspension of Glycosides - Centrifugation; - Washing with ethanol.
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