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(12) Patent Application Publication (10) Pub. No.: US 2008/01601 16 A1 Li Et Al US 2008O1601 16A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/01601 16 A1 Li et al. (43) Pub. Date: Jul. 3, 2008 (54) COMPOSITIONS AND METHODS Publication Classification COMPRISING ZNGBER SPECIES (51) Int. Cl. A636/906 (2006.01) (75) Inventors: Dan Li, Singapore (CN); George A 6LX 3L/75 (2006.01) W. Sypert, Naples, FL (US); A6II 3/12 (2006.01) Robert T. Gow, Naples, FL (US) A6IP 43/00 (2006.01) (52) U.S. Cl. ............................ 424/756; 514/678; 514/54 Correspondence Address: (57) ABSTRACT FOLEY HOAG, LLP PATENT GROUP, WORLD TRADE CENTER An aspect of the present invention relates to compositions WEST comprising a gingerol, for example, compositions compris 155 SEAPORT BLVD inggingerol in an amount greater than about 2% by weight. In BOSTON, MA 02110 Some aspects of the invention, the composition comprises 6-gingerol, 8-gingerol, 10-gingerol, 6-shagaol, or combina tions thereof. Another aspect of the invention relates to a (73) Assignee: HerbalScience Singapore Pte. method for extracting a ginger species comprising, sequen Ltd, Singapore (SG) tially extracting a ginger species plant material to yield an essential oil fraction, a gingerol fraction, a phenolic fraction, (21) Appl. No.: 11/951,948 and a polysaccharide fraction, wherein the essential oil and gingerol fractions are derived by extracting plant feedstock (22) Filed: Dec. 6, 2007 material by Supercritical carbon dioxide extraction, the phe nolic fraction is extracted from the plant feedstock material or from the remainder of the essential oil and gingerol extrac Related U.S. Application Data tions by hydroalcoholic extraction, and the polysaccharide (60) Provisional application No. 60/873,320, filed on Dec. fraction is derived by water extraction of the remainder of the 7, 2006. phenolic extraction. Patent Application Publication Jul. 3, 2008 Sheet 1 of 26 US 2008/O16011.6 A1 Figure 1. STEP 1A Ginger feedstock 10 210 Solvent SFE20 Essential Oil Fraction 30 Residue 40 STEP 1B Ginger Feedstock 10 210 Solvent — SFE 20 Essential Oil Sub-fraction 50 210 Solvent SFE 20 Essential Oil Sub-fraction 60 210 Solvent SFE 20 -> Essential Oil Sub-fraction 70 210 Solvent — SFE 20 Essential Oil Sub-fraction 80 Residue 40 Patent Application Publication Jul. 3, 2008 Sheet 2 of 26 US 2008/O16011.6 A1 Figure 2. STEP 1C Ginger Feedstock 10 210 Solvent Fractionation SFE 100 Separator I 110 Separator 2120 Separator 3 130 Residue 140 Purified/Profiled Purified/Profiled Purified/Profiled Essential Oil ESSential Oil Essential Oil Sub-fraction Sub-fraction Sub-fraction Patent Application Publication Jul. 3, 2008 Sheet 3 of 26 US 2008/O16011.6 A1 Figure 3. STEP 2 Ginger species Feedstock 10 or Residue Step 1 40 220 Solvent Leaching Extraction 300 Fink 310 certain 320 Crude Phenolic 330 Residue 340 Fraction-Stage I 220 Solvent Extraction 300 Filtration 310 Centrifugation 320 Residue 360 Crude Phenolic Fraction 350 Stage II 220 Solvent turn 300 Finn 310 Centrtifugation 320 Residue 380 Crude Phenoc Fraction 370 Stage III Patent Application Publication Jul. 3, 2008 Sheet 4 of 26 US 2008/O16011.6 A1 Figure 4. STEP 3 Affinity Adsorbent 400 Solvent 230 Wash Column 410 Solvent in Wash Coluhn 420 Sample (330+350 — Load Column 430 Effluent 440 Solvent 240 Washing 460 Solvent 250 Elute Column 470 Purified Phenolic Fractions 480 Patent Application Publication Jul. 3, 2008 Sheet 5 of 26 US 2008/O16011.6 A1 Figure 5. STEP 4 Ginger Residue Step 2 Feedstock 380 Solvent 260 Extraction 500 Residue 510 Extract Solution I 600 Solvent 260 Extraction 520 Residue 530 Extract Solution II 610 Extract Solutions I + II 600+610 F into 540 certain 550 furio 560 Concentrated Sample 620 Solvent 270 Precipitation 570 Centrifugation 580 Decantation 590 Residue 630 Precipitate 640 Polysaccharide Fraction Patent Application Publication Jul. 3, 2008 Sheet 6 of 26 US 2008/O16011.6 A1 Figure 6A MSOE98.0740. O'MSO(4). 301 E3+Ginger 60% and 30%DAR" (). : &O 383 (12579) SS3 173136: 13:35:25 (itA2.63ES l is833S 1815, R.E. 3.478 3928. Figure 6B soon : A 83 (5474) 38.095 S 25.5545 1. 3983488 233. SOF O A617.8 22.283 9.S. 353766 al 233 li a ple, O 3. f Patent Application Publication Jul. 3, 2008 Sheet 7 of 26 US 2008/O16011.6 A1 Figure 7A s 137-38. MS-03.038 E3+38.30% and 3%DART; O2 to Area's 3.78 S383 43E8 TETE 5.5 x S35 . 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O Patent Application Publication Jul. 3, 2008 Sheet 11 of 26 US 2008/O16011.6 A1 Figure 8D r Sh r r O O O s r s l r O L O st l s OO O s& O si. 3. s c r r Sr. o o s ar c O Y CY s r r c 2. O (- -. me -- - ca Y ca N- -- 3 y - c - o O O re ca -- r -- -- E. re S - *xr P -- re O C S SE -et- - Patent Application Publication Jul. 3, 2008 Sheet 12 of 26 US 2008/O16011.6 A1 Figure 8E Patent Application Publication Jul. 3, 2008 Sheet 13 of 26 US 2008/O16011.6 A1 Figure 8F S r O r i?s s l r -- r r s r C s? C) s Si s c s c s s t C - t s s O c o - s i- m s s ra Ea c 3 c crisis in s l - r ce r- s o C ra n -- c r s s se s O r- us re Y C S CO Patent Application Publication Jul. 3, 2008 Sheet 14 of 26 US 2008/O16011.6 A1 Figure 8G La S O l la -- CE r t Cs CCB O s O l st l r s r s re s r O s o S2 O r 3. o s & - A r O O c s C t c Y. cy s Yo cN O c- y ^ - I Ces c l co s es c- E. co re O c- O C C --- - --- re r O sa -- - - as o O C O C 8 Oo r -- Patent Application Publication Jul. 3, 2008 Sheet 15 of 26 US 2008/016011.6 A1 Figure 9A Patent Application Publication Jul. 3, 2008 Sheet 16 of 26 US 2008/O16011.6 A1 Figure 9B Patent Application Publication Jul. 3, 2008 Sheet 17 of 26 US 2008/O16011.6 A1 Figure 9C L. L. r s - t r r re si. s C Sp C s c S SF w si. rea re O C w- --- c --- l i 3. o c a r O C c- r O s - aar s CY sate s c- O sts s C O r r r re- re s 92 re re -- re S O Patent Application Publication Jul. 3, 2008 Sheet 18 of 26 US 2008/O16011.6 A1 Figure 9D & S : S. S. S. S. s S. 3 s 3. & S. s s s S s S Patent Application Publication Jul. 3, 2008 Sheet 19 of 26 US 2008/O16011.6 A1 Figure 9E Patent Application Publication Jul. 3, 2008 Sheet 20 of 26 US 2008/O16011.6 A1 Figure 10A Patent Application Publication Jul. 3, 2008 Sheet 21 of 26 US 2008/O16011.6 A1 Figure 10B c 3. O re c st s Y c .. Y i Y ca es a. in s C r S 9. S Patent Application Publication Jul. 3, 2008 Sheet 22 of 26 US 2008/O16011.6 A1 Figure 1 1A si. s r S. rt 3. r SS s r S. c r S. o re r - Yo cy -- l Y cy re s Y cy c CO C Y cy OO a 3 s S. S Patent Application Publication Jul. 3, 2008 Sheet 23 of 26 US 2008/O16011.6 A1 Figure l l B s S s r O o -- r s w la r L s r S. s r s ir s c S cg s ar r s S. sa r ca s' s E Y i is r s C c s s s - s s s s -- N re is S - -- rw --- - O s s ses o S SE E s S Patent Application Publication Jul.
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