US20070292544A1 - Tea Polyphenol Composition and Method for Producing the Same - Google Patents
Tea Polyphenol Composition and Method for Producing the Same Download PDFInfo
- Publication number
- US20070292544A1 US20070292544A1 US11/631,444 US63144404A US2007292544A1 US 20070292544 A1 US20070292544 A1 US 20070292544A1 US 63144404 A US63144404 A US 63144404A US 2007292544 A1 US2007292544 A1 US 2007292544A1
- Authority
- US
- United States
- Prior art keywords
- tea
- weight
- catechins
- gallate
- polyphenol composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 73
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 71
- 239000000203 mixture Substances 0.000 title claims abstract description 70
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims abstract description 86
- 235000005487 catechin Nutrition 0.000 claims abstract description 86
- 150000001765 catechin Chemical class 0.000 claims abstract description 71
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 claims abstract description 53
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 claims abstract description 51
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 claims abstract description 50
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 241001122767 Theaceae Species 0.000 claims abstract description 35
- LVJJFMLUMNSUFN-UHFFFAOYSA-N gallocatechin gallate Natural products C1=C(O)C=C2OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C1OC(=O)C1=CC(O)=C(O)C(O)=C1 LVJJFMLUMNSUFN-UHFFFAOYSA-N 0.000 claims abstract description 25
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229940030275 epigallocatechin gallate Drugs 0.000 claims abstract description 16
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims abstract description 15
- WMBWREPUVVBILR-GHTZIAJQSA-N (+)-gallocatechin gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-GHTZIAJQSA-N 0.000 claims abstract description 15
- 229950001002 cianidanol Drugs 0.000 claims abstract description 15
- XMOCLSLCDHWDHP-SWLSCSKDSA-N (+)-Epigallocatechin Natural products C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-SWLSCSKDSA-N 0.000 claims abstract description 11
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 claims abstract description 11
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 claims abstract description 11
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 claims abstract description 11
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000012734 epicatechin Nutrition 0.000 claims abstract description 11
- LSHVYAFMTMFKBA-PZJWPPBQSA-N (+)-catechin-3-O-gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-PZJWPPBQSA-N 0.000 claims abstract description 10
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 claims abstract description 9
- 229920005989 resin Polymers 0.000 claims description 45
- 239000011347 resin Substances 0.000 claims description 45
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims description 34
- 238000000605 extraction Methods 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 238000001179 sorption measurement Methods 0.000 claims description 24
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims description 18
- 229960001948 caffeine Drugs 0.000 claims description 18
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 16
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 12
- 229940074391 gallic acid Drugs 0.000 claims description 6
- 235000004515 gallic acid Nutrition 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 235000019606 astringent taste Nutrition 0.000 abstract description 26
- 235000019658 bitter taste Nutrition 0.000 abstract description 26
- 244000269722 Thea sinensis Species 0.000 description 138
- 235000013616 tea Nutrition 0.000 description 128
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- 239000000243 solution Substances 0.000 description 77
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 238000000034 method Methods 0.000 description 48
- 239000007788 liquid Substances 0.000 description 43
- 239000000047 product Substances 0.000 description 43
- 230000000052 comparative effect Effects 0.000 description 17
- 239000012528 membrane Substances 0.000 description 13
- 235000019640 taste Nutrition 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 235000009569 green tea Nutrition 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- 230000001766 physiological effect Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 8
- 238000001223 reverse osmosis Methods 0.000 description 8
- 239000007921 spray Substances 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 235000006468 Thea sinensis Nutrition 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 206010028813 Nausea Diseases 0.000 description 2
- 206010033557 Palpitations Diseases 0.000 description 2
- 229930184207 Polyphenon Natural products 0.000 description 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000003064 anti-oxidating effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 208000002173 dizziness Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000019225 fermented tea Nutrition 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 206010022437 insomnia Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008693 nausea Effects 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- -1 (−)-EC Natural products 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000020279 black tea Nutrition 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 235000020333 oolong tea Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009290 primary effect Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/82—Theaceae (Tea family), e.g. camellia
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to a tea polyphenol composition with a taste improved in bitterness, astringency and the like and a production method thereof.
- catechins in tea polyphenols have various effects such as an antioxidating effect (Japanese Patent Laid-open No. S59-219384 and Japanese Patent Laid-open No. H1-268683), antimicrobial and bacteriostatic effects (Japanese Patent Laid-open No. H2-276562 and Japanese Patent Laid-open No. H3-246227), an inhibitory activity for cholesterol increase (Japanese Patent Laid-open No. S60-156614), an inhibitory activity for blood pressure increase (Japanese Patent Laid-open No. S63-214183) and an inhibitory activity for blood glucose increase (Japanese Patent Laid-open No. H4-253918).
- Patent Document 1 a method of purifying polyphenolic compounds (catechins) to a high purity by contacting with lignocelluloses (refer to Patent Document 1), a method of producing tea catechin compounds in high yields by separating out the unrequired fraction with gel column chromatography using aqueous solutions of hydrophilic organic solvents with concentrations appropriately varied (refer to Patent Document 2), a method of producing highly pure catechins by eliminating caffeine in tea leaves by passing a tea extraction through a liquid chromatography column packed with an adsorbent such as cyclodextrin polymer (refer to Patent Document 3) and the like.
- Patent Document 2 a method of purifying polyphenolic compounds (catechins) to a high purity by contacting with lignocelluloses
- Patent Document 2 a method of producing tea catechin compounds in high yields by separating out the unrequired fraction with gel column chromatography using aqueous solutions of hydrophilic organic solvents with concentrations appropriately varied
- Patent Document 3 a method of producing
- Patent Document 1 Japanese Patent Laid-open No. H7-238078
- Patent Document 2 Japanese Patent Laid-open No. H1-175978
- Patent Document 3 Japanese Patent Laid-open No. H10-67771
- bitterness and astringency increase greatly.
- Moderate bitterness and astringency are crucial in flavor, but excess bitterness and astringency are not generally favorable as a taste.
- an object of the present invention is to overcome the above problems and to provide a tea polyphenol composition that has reduced bitterness and astringency while containing catechins in high purity, and an effective production method thereof.
- the present inventors have undertaken extensive studies to achieve the above objective and found that an excellent tea polyphenol composition that has lower bitterness and astringency while containing catechins in high purity, can be obtained by making the content ratio of ingredients contained in the tea polyphenol composition conform to a specific range. Based on these findings they have completed the present invention.
- the present invention related to claim 1 is a tea polyphenol composition, (A) comprising 85% by weight to 95% by weight of catechins, (B) wherein the catechins contain epigallocatechin gallate and gallocatechin gallate at a ratio of 65% by weight to 80% by weight and (C) wherein the ratio given by (epigallocatechin gallate+gallocatechin gallate)/(epicatechin+catechin+epigallocatechin+gallocatechin+epicatechin gallate+catechin gallate) is from 2 to 4.
- the present invention related to claim 2 is a tea polyphenol composition described in claim 1 , wherein the ratio given by (epigallocatechin gallate+epicatechin gallate+gallocatechin gallate+catechin gallate)/(epicatechin+epigallocatechin+gallocatechin+catechin) is from 3 to 7.
- the present invention related to claim 3 is a tea polyphenol composition described in claims 1 and 2 , wherein the ratio given by (epigallocatechin gallate+gallocatechin gallate)/(epicatechin+epigallocatechin+gallocatechin+catechin) is from 2 to 6.
- the present invention related to claim 4 is a tea polyphenol composition described in claims 1 to 3 , wherein the catechins contains gallocatechin gallate, gallocatechin, catechin gallate and catechin at a ratio of 2% by weight to 15% by weight.
- the present invention related to claim 5 is a tea polyphenol composition described in claims 1 to 4 , wherein the ratio given by epigallocatechin gallate/(epicatechin+epigallocatechin+epicatechin gallate) is from 2 to 4.
- the present invention related to claim 6 is a tea polyphenol composition described in claims 1 to 5 , comprising 0.0001% by weight to 1.2% by weight of caffeine.
- the present invention related to claim 7 is a tea polyphenol composition described in claims 1 to 6 , comprising 0.0001% by weight to 0.2% by weight of ash.
- the present invention related to claim 8 is a tea polyphenol composition described in claims 1 to 7 , comprising no gallic acid.
- the present invention related to claim 9 is a method for producing the tea polyphenol compositions described in claims 1 to 8 performed in the following steps 1) to 3):
- the tea polyphenol composition of the present invention contains a higher catechin purity, so that it can more effectively exert excellent physiological effects of catechins, for example, an antioxidating effect, antimicrobial and bacteriostatic effects, an inhibitory activity for cholesterol increase, an inhibitory activity for blood pressure increase, an inhibitory effect against blood glucose increase and the like.
- the tea polyphenol composition of the present invention exhibits an excellent improved taste, with reduced bitterness and astringency.
- the present invention related to claim 1 is a tea polyphenol composition, wherein (A) comprising 85% by weight to 95% by weight of catechins, (B) wherein the catechins contains epigallocatechin gallate and gallocatechin gallate at a ratio of 65% by weight to 80% by weight and (C) wherein the ratio given by (epigallocatechin gallate+gallocatechin gallate)/(epicatechin+catechin+epigallocatechin+gallocatechin+epicatechin gallate+catechin gallate) is from 2 to 4.
- the “catechins” in the present invention means a collective term including epigallocatechin gallate (hereinafter referred to as EGCg), epigallocatechin (hereinafter referred to as EGC), epicatechin gallate (hereinafter referred to as ECg), epicatechin (hereinafter referred to as EC), gallocatechin gallate (hereinafter referred to as GCg), gallocatechin (hereinafter referred to as GC), catechin gallate (hereinafter referred to as Cg) and catechin (hereinafter referred to as C).
- EGCg epigallocatechin gallate
- EGC epigallocatechin
- ECg epicatechin gallate
- ECg epicatechin gallate
- GCg gallocatechin gallate
- Cg catechin gallate
- Cg catechin gallate
- C catechin gallate
- Each of catechins described here may be either (+)-form or ( ⁇ )-form, and ( ⁇ )-EGCg, ( ⁇ )-EGC, ( ⁇ )-ECg, ( ⁇ )-EC, ( ⁇ )-GCg, ( ⁇ )-GC, ( ⁇ )-Cg and (+)-C are preferable.
- the tea polyphenol composition of the present invention related to claim 1 comprises the above-described catechins in a content of 85% by weight to 95% by weight, preferably 85.5% by weight to 94.5% by weight, more preferably 86% by weight to 94% by weight and further more preferably 86.5% by weight to 93.5% by weight.
- the concentration of the catechins described here is defined based on the total amount of the eight kinds of compounds, EGCg, EGC, ECg, EC, GCg, GC, Cg and C.
- the ratio of EGCg and GCg is required to be from 65% by weight to 80% by weight, preferably from 66% by weight to 79% by weight, more preferably from 67% by weight to 79% by weight and further more preferably from 68% by weight to 78.5% by weight.
- the value obtained by dividing the sum of the concentrations of EGCg and GCg by the sum of the concentrations of EC, C, EGC, GC, ECg and Cg is preferably from 2 to 4, more preferably from 2.1 to 3.9, further more preferably from 2.2 to 3.8 and most preferably from 2.3 to 3.7 in order to improve the taste of the catechins such as bitterness and astringency.
- the value obtained by dividing the sum of concentrations of EGCg, ECg, GCg and Cg (catechin gallate) by the sum of the concentrations of EC, EGC, GC and C (non-gallated catechins) is preferably from 3 to 7, more preferably from 3.1 to 6.8, further more preferably from 3.1 to 6.6 and most preferably from 3.2 to 6.4. This range is preferred because the excellent physiological effects of the catechins are readily exerted and because tastes such as bitterness and astringency are reduced.
- the value given by dividing the sum of the concentrations of EGCg and GCg by the sum of the concentrations of EC, EGC, GC and C is preferably from 2 to 6, more preferably from 2.5 to 5.9, further more preferably from 2.8 to 5.8 and most preferably from 2.9 to 5.6 in order to improve the taste of the catechins such as bitterness and astringency.
- the total content of GCg, GC, Cg and C (non-epimerized catechins) in the catechins is preferably from 2% by weight to 15% by weight, more preferably from 2.2% by weight to 13% by weight, further more preferably from 2.5% by weight to 11% by weight and most preferably from 2.7% by weight to 10.4% by weight in order to improve the flavor.
- the weight ratio given by EGCg/(EC+EGC+ECg) is preferably from 2 to 4, more preferably from 2.2 to 3.9 and further more preferably from 2.1 to 3.8 in order to improve the taste of the catechins such as bitterness and astringency.
- the content of caffeine is preferably from 0.0001% by weight to 1.2% by weight and more preferably from 0.001% by weight to 1.2% by weight. If the content of caffeine exceeds 1.2% by weight, dizziness, insomnia, palpitation, nausea or other symptoms could be caused due to the strong physiological effects of caffeine under some conditions of intake and of the person who takes it, and thus such a high caffeine content is not preferred.
- the content of ash is preferably from 0.0001% by weight to 0.2% by weight and more preferably from 0.001% by weight to 0.2% by weight in order to improve the taste such as astringency and bitterness.
- gallic acid is not present in order to exert the excellent physiological effects of the catechins more effectively.
- composition having all the requirements described in the above claims 1 to 8 and with improved tastes such as astringency and bitterness is preferred, and in particular the composition with a combination of the preferred ranges is more preferred.
- the tea polyphenol compositions described in claims 1 to 8 which are described above, can be produced, for example, by the method of the present invention related to claim 9 .
- the present invention related to claim 9 is a method for producing the tea polyphenol compositions described in claims 1 to 8 performed in the following steps 1) to 3):
- the “tea polyphenol” in the present invention means an extract containing polyphenol(s) extracted from tea leaves or a purified polyphenolic compound.
- tea leaves means leaves derived from a tea plant belonging to Theaceae (Camellia sinensis) and may include, regardless of being fermented or not, any one of fermented teas such as ready-made black tea and puer tea, semi-fermented tea such as oolong tea and Pao Chung tea and non-fermented tea such as green tea, pan-roasted green tea and roasted tea and it may be a mixture of two or more kinds of these.
- the amount of the polyphenol of the present invention may be determined by the colorimetric quantitative analysis method using iron tatarate, but measurement with reversed phase high performance liquid chromatography is preferred to determine the composition of the tea polyphenol in detail.
- the tea leaves used in the present invention may be raw or dried, but dried leaves are preferably used.
- dried material the tea leaves are dried and then crushed if necessary to provide the raw material for the extraction step.
- such material can be prepared by drying the raw tea leaves followed by crushing or by cutting the raw tea leaves into small pieces followed by drying.
- the present invention related to claim 9 comprises the three steps, 1) to 3) mentioned above.
- the first step is a step in which tea components containing the catechins are extracted from the tea leaves with hot water and then further extracted with an organic solvent to provide a tea extract (extraction step).
- the tea components containing the catechins are at first extracted from the above-described tea leaves with hot water.
- the temperature is preferably from 60° C. to 100° C., more preferably from 70° C. to 90° C. and most preferably from 80° C. to 85° C. If this extraction is done at a temperature over 100° C., structural conversions such as isomer polymerization of the catechins could take place, and thus such a high temperature is unfavorable, whereas if extracted below 60° C., the catechins are not fully extracted, thus such a low temperature is unfavorable.
- the catechins can be extracted at a temperature lower than that under atmospheric pressure, and the temperature on extraction may be adjusted as appropriate for the pressure applied.
- the amount of hot water for extraction from the tea leaves is, although not particularly limited to, preferably three to ten times, more preferably five to seven times that of the tea leaves by weight. If the amount of hot water used is less than three times that of the tea leaves by weight, the catechins cannot be sufficiently extracted, whereas use of hot water in an amount of more than ten times that of the tea leaves does not particularly improve the extraction efficiency. Extraction with hot water may be performed either only once or repeatedly two or more times but it is preferred to extract twice. When extraction is performed twice, the amounts of hot water used are, although not particularly limited to, preferably seven times that of the tea leaves by weight in the first extraction and five times that of the tea leaves by weight in the second extraction.
- the liquid extract obtained by the above-described extraction with hot water is cooled once.
- the temperature on cooling is preferably 50° C. or lower, more preferably 30° C. or lower and most preferably 15° C. or lower. If the temperature on cooling exceeds 50° C., insoluble components cannot be fully removed in centrifugal filtration in a later step, and thus such a condition is not favored.
- the method for concentration may be any of methods generally used, for example, vacuum concentration method, atmospheric concentration method, heating concentration method, batch concentration method, membrane concentration method and circulation concentration method.
- the membrane concentration method in particular, the membrane concentration method with a reverse osmosis (RO) membrane is preferably used. Filter filtration, centrifugal filtration or the like may be run prior to concentration without any problem.
- RO reverse osmosis
- the tea components containing the catechins are extracted from the tea leaves with hot water, and the liquid extract obtained is preferably cooled and then concentrated, thereby yielding a concentrated liquid, which is further extracted with an organic solvent.
- the organic solvent used here includes an organic solvent that can dissolve the tea polyphenol, for example, acetonitrile, methanol, ethanol, ethyl acetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, tetrahydrofuran or dioxane, hydrous organic solvent thereof and a mixed solvent of these organic solvents.
- ethyl acetate is preferably used.
- the amount of the organic solvent is preferably a half to five times, more preferably one to three times, most preferably one and a half to two times that of the concentrated liquid by volume. If the volume of the organic solvent is less than a half of the concentrated liquid, the catechins cannot be fully extracted, whereas if the volume exceeds five times that of the concentrated liquid, the extraction efficiency is not particularly improved.
- the concentration method used here may be any of methods generally used including, for example, vacuum concentration method, atmospheric concentration method, heating concentration method, batch concentration method, membrane concentration method or circulation concentration method. A combination of any of the above-mentioned methods may be also used, and a combination of vacuum concentration method, heating concentration method and circulation concentration method is particularly preferred.
- the above-described concentrated liquid is dried to obtain a tea extract (crude tea extract).
- the drying method is, although not particularly limited to, preferably spray drying method, freeze drying method, vacuum drying method or the like.
- a commercial product may be also used as a crude tea extract without any problem.
- the second step is a step to feed the tea extract (crude tea extract) obtained in the first step to a synthetic adsorption resin.
- the crude tea extract obtained is dissolved preferably in a 5% to 15% aqueous alcohol solution, more preferably in a 10% aqueous alcohol solution and further more preferably in a 10% aqueous methanol solution, and then the resultant solution is fed to a synthetic adsorption resin to adsorb tea extract components.
- the synthetic adsorption resin used is preferably crosslinked styrenic type, including, for example, HP-20 (Diaion, manufactured by Mitsubishi Chemical Corporation), Sepabeads (manufactured by Mitsubishi Chemical Corporation), Amberlite (manufactured by Organo Corporation), Shodex (manufactured by Showa Denko K.K.) and Sephadex (manufactured by Pharmacia Fine Chemicals AB).
- HP-20 Diaion, manufactured by Mitsubishi Chemical Corporation
- Sepabeads manufactured by Mitsubishi Chemical Corporation
- Amberlite manufactured by Organo Corporation
- Shodex manufactured by Showa Denko K.K.
- Sephadex manufactured by Pharmacia Fine Chemicals AB
- the third step is a step in which the synthetic adsorption resin is washed with a 5% to 15% aqueous alcohol solution and then the tea catechins are eluted by passing a 30% to 50% aqueous alcohol solution through the resin.
- the synthetic adsorption resin is at first washed with a 5% to 15% aqueous alcohol solution to wash out the unadsorbed components.
- concentration of the aqueous alcohol solution used here may be from 5% to 15% and preferably 10%.
- a volume of 50 L or more is sufficient as the amount of the aqueous alcohol solution to be passed through a column with a capacity of 300 L.
- a 30% to 50% aqueous alcohol solution is passed through to elute the tea catechins.
- the kind of the aqueous alcohol solution used here is, although not restricted, preferably an aqueous methanol solution.
- the concentration of the aqueous alcohol solution may be from 30% to 50%, and is preferably from 35% to 45% and more preferably 40%. Therefore, a 40% aqueous methanol solution is preferably used to elute the tea catechins.
- the volume of the aqueous alcohol solution passed through a column with a capacity of 300 L is 100 L or more and preferably 280 ⁇ 56 L.
- aqueous alcohol solution used here is, although not restricted, preferably an aqueous methanol solution.
- concentration of the aqueous alcohol solution may be from 50% to 100% and is preferably from 60% to 80% and more preferably 70%.
- the volume of the aqueous alcohol passed through a column with a capacity of 300 L is 100 L or more, preferably 400 L or more and further preferably 600 L or more.
- recovery of the tea catechin fraction starts at a time when the content of ( ⁇ )-EGCg has reached a level twice or more, preferably five times or more, as high as that of ( ⁇ )-EGC and ends at a time when the content of ( ⁇ )-EGCg has reached a level lower than that of ( ⁇ )-ECg or at a time when the content of caffeine becomes 5%, preferably 1%. If the timing to start the recovery is set earlier than the above timing, the content of ( ⁇ )-EGCg decreases, whereas if the timing to end the recovery is later than the above timing, the content of ( ⁇ )-EGCg decreases and the content of caffeine increases.
- the tea polyphenol composition of the present invention is obtained by concentrating and drying the tea catechin fraction obtained in the above steps.
- the concentration method may be any of the methods generally used including, for example, vacuum concentration method, atmospheric concentration method, heating concentration method, batch concentration method, membrane concentration method, circulation concentration method or the like.
- a combination of a any of the above-mentioned concentration methods may be also used and a combination of vacuum concentration method, heating concentration method and circulation concentration method is preferred in particular.
- spray drying method, freeze drying method, vacuum drying method and the like may be favorably used.
- this tea polyphenol composition can be expected to contribute to imparting the primary effects of the polyphenol, for example, physiological functions, such as antioxidative effect, antimicrobial and bacteriostatic effects, inhibitory action on cholesterol increase, inhibitory action on blood pressure increase and an inhibitory action on blood glucose increase, without fear of the negative effects of caffeine described hereinafter because the composition has a high content of the tea catechins with a gallate group and almost no caffeine or gallic acid content.
- Caffeine is known to have physiological activities such as an excitatory activity on the central nervous system, a positive inotropic effect and a diuretic effect. Under some conditions of the intake and of the person who takes it, dizziness, insomnia, palpitation, nausea or other symptoms might be caused due to strong physiological effects of caffeine, so that people hypersensitive to caffeine may regard intake of caffeine problematic.
- the tea polyphenol composition of the present invention is chemically, physically and biologically very stable, the field of its application is not limited, and it can be added to, for example, food and drink, pharmaceuticals, quasi drugs, cosmetics, textiles or the like.
- the product of the present invention may be used together with a vitamin such as tocopherol or vitamin C, an antimicrobial or bactericidal agent, a coloring matter, an aroma agent, a bulking agent, a coating agent or the like.
- the tea catechin fraction was eluted with 280 L of a 40% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 70% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 1 in the present invention.
- a centrifugal thin-film evaporator manufactured by Okawara Mfg. Co., Ltd.
- Mobile phase solution A A solution containing acetonitrile and aqueous phosphoric acid solution with a ratio of 10:400
- Mobile phase solution B A solution containing methanol, acetonitrile and aqueous phosphoric acid solution with a ratio of 200:10:400
- the tea catechin fraction was eluted with 280 L of a 35% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 70% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 2 in the present invention.
- a centrifugal thin-film evaporator manufactured by Okawara Mfg. Co., Ltd.
- the tea catechin fraction was eluted with 280 L of a 35% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 70% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 3 in the present invention.
- a centrifugal thin-film evaporator manufactured by Okawara Mfg. Co., Ltd.
- the tea catechin fraction was eluted with 280 L of a 45% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 65% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 4 in the present invention.
- a centrifugal thin-film evaporator manufactured by Okawara Mfg. Co., Ltd.
- the tea catechin fraction was eluted with 280 L of a 35% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 70% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 5 in the present invention.
- a centrifugal thin-film evaporator manufactured by Okawara Mfg. Co., Ltd.
- the tea catechin fraction was eluted with 280 L of a 40% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 65% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 6 in the present invention.
- a centrifugal thin-film evaporator manufactured by Okawara Mfg. Co., Ltd.
- the tea catechin fraction was eluted with 280 L of a 40% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 75% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 7 in the present invention.
- a centrifugal thin-film evaporator manufactured by Okawara Mfg. Co., Ltd.
- Each sample of Products 1 to 7 in the present invention obtained in the examples and Comparative Products 1 to 3 was added to 800 g of ion-exchanged water so that the catechin content was 1 g.
- 0.3 g of sodium ascorbate and an appropriate amount of a 5% aqueous sodium bicarbonate solution were added to adjust pH to 6.2 and the solution was further diluted with ion-exchanged water to adjust the total amount to 1000 g to prepare a test solution.
- the products in the present invention were compared with the comparative products to evaluate whether the bitterness and astringency were reduced or not. Evaluation of bitterness and astringency was rated in five levels described below. After evaluation of one sample of the test and comparative solutions, the mouth was rinsed with warm water, and next evaluation was conducted after 30 min or later.
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Abstract
The objective of the present invention is to provide a tea polyphenol composition that has reduced bitterness and astringency while containing catechins with high purity. The present invention provides a tea polyphenol composition, (A) comprising 85% by weight to 95% by weight of catechins, (B) wherein the catechins contains epigallocatechin gallate and gallocatechin gallate at a ratio of 65% by weight to 80% by weight and (C) wherein the ratio given by (epigallocatechin gallate+gallocatechin gallate)/(epicatechin+catechin+epigallocatechin+gallocatechin+epicatechin gallate+catechin gallate) is from 2 to 4.
Description
- The present invention relates to a tea polyphenol composition with a taste improved in bitterness, astringency and the like and a production method thereof.
- It has been known that catechins in tea polyphenols have various effects such as an antioxidating effect (Japanese Patent Laid-open No. S59-219384 and Japanese Patent Laid-open No. H1-268683), antimicrobial and bacteriostatic effects (Japanese Patent Laid-open No. H2-276562 and Japanese Patent Laid-open No. H3-246227), an inhibitory activity for cholesterol increase (Japanese Patent Laid-open No. S60-156614), an inhibitory activity for blood pressure increase (Japanese Patent Laid-open No. S63-214183) and an inhibitory activity for blood glucose increase (Japanese Patent Laid-open No. H4-253918).
- An increased catechin intake is needed to attain such excellent physiological effects. Tea polyphenol compositions containing high concentrations of catechins have been developed so far.
- There have been known, for example, a method of purifying polyphenolic compounds (catechins) to a high purity by contacting with lignocelluloses (refer to Patent Document 1), a method of producing tea catechin compounds in high yields by separating out the unrequired fraction with gel column chromatography using aqueous solutions of hydrophilic organic solvents with concentrations appropriately varied (refer to Patent Document 2), a method of producing highly pure catechins by eliminating caffeine in tea leaves by passing a tea extraction through a liquid chromatography column packed with an adsorbent such as cyclodextrin polymer (refer to Patent Document 3) and the like.
- Patent Document 1: Japanese Patent Laid-open No. H7-238078
- Patent Document 2: Japanese Patent Laid-open No. H1-175978
- Patent Document 3: Japanese Patent Laid-open No. H10-67771
- In order to increase catechin intake for the purpose of obtaining higher physiological effects, it is effective to ingest a tea polyphenol composition in which the purity of catechins is increased by the above methods.
- However, when the tea polyphenol composition with an increased purity of catechins is produced by these methods, bitterness and astringency increase greatly. Moderate bitterness and astringency are crucial in flavor, but excess bitterness and astringency are not generally favorable as a taste.
- Accordingly, an object of the present invention is to overcome the above problems and to provide a tea polyphenol composition that has reduced bitterness and astringency while containing catechins in high purity, and an effective production method thereof.
- The present inventors have undertaken extensive studies to achieve the above objective and found that an excellent tea polyphenol composition that has lower bitterness and astringency while containing catechins in high purity, can be obtained by making the content ratio of ingredients contained in the tea polyphenol composition conform to a specific range. Based on these findings they have completed the present invention.
- That is, the present invention related to claim 1 is a tea polyphenol composition, (A) comprising 85% by weight to 95% by weight of catechins, (B) wherein the catechins contain epigallocatechin gallate and gallocatechin gallate at a ratio of 65% by weight to 80% by weight and (C) wherein the ratio given by (epigallocatechin gallate+gallocatechin gallate)/(epicatechin+catechin+epigallocatechin+gallocatechin+epicatechin gallate+catechin gallate) is from 2 to 4.
- The present invention related to claim 2 is a tea polyphenol composition described in claim 1, wherein the ratio given by (epigallocatechin gallate+epicatechin gallate+gallocatechin gallate+catechin gallate)/(epicatechin+epigallocatechin+gallocatechin+catechin) is from 3 to 7.
- The present invention related to claim 3 is a tea polyphenol composition described in claims 1 and 2, wherein the ratio given by (epigallocatechin gallate+gallocatechin gallate)/(epicatechin+epigallocatechin+gallocatechin+catechin) is from 2 to 6.
- The present invention related to claim 4 is a tea polyphenol composition described in claims 1 to 3, wherein the catechins contains gallocatechin gallate, gallocatechin, catechin gallate and catechin at a ratio of 2% by weight to 15% by weight.
- The present invention related to claim 5 is a tea polyphenol composition described in claims 1 to 4, wherein the ratio given by epigallocatechin gallate/(epicatechin+epigallocatechin+epicatechin gallate) is from 2 to 4.
- The present invention related to claim 6 is a tea polyphenol composition described in claims 1 to 5, comprising 0.0001% by weight to 1.2% by weight of caffeine.
- The present invention related to claim 7 is a tea polyphenol composition described in claims 1 to 6, comprising 0.0001% by weight to 0.2% by weight of ash.
- The present invention related to claim 8 is a tea polyphenol composition described in claims 1 to 7, comprising no gallic acid.
- The present invention related to claim 9 is a method for producing the tea polyphenol compositions described in claims 1 to 8 performed in the following steps 1) to 3):
- 1) A step in which tea components containing the catechins are extracted from tea leaves with hot water and further extracted with an organic solvent to provide a tea extract;
- 2) A step in which the tea extract is fed to a synthetic adsorption resin; and
- 3) A step in which the synthetic adsorption resin is washed with a 5% to 15% aqueous alcohol solution and then the tea catechins is eluted by passing a 30% to 50% aqueous alcohol solution through the resin.
- The tea polyphenol composition of the present invention contains a higher catechin purity, so that it can more effectively exert excellent physiological effects of catechins, for example, an antioxidating effect, antimicrobial and bacteriostatic effects, an inhibitory activity for cholesterol increase, an inhibitory activity for blood pressure increase, an inhibitory effect against blood glucose increase and the like.
- In addition, the tea polyphenol composition of the present invention exhibits an excellent improved taste, with reduced bitterness and astringency.
- Furthermore, by the method of the present invention, such a tea polyphenol composition can be efficiently produced.
- The present invention related to claim 1 is a tea polyphenol composition, wherein (A) comprising 85% by weight to 95% by weight of catechins, (B) wherein the catechins contains epigallocatechin gallate and gallocatechin gallate at a ratio of 65% by weight to 80% by weight and (C) wherein the ratio given by (epigallocatechin gallate+gallocatechin gallate)/(epicatechin+catechin+epigallocatechin+gallocatechin+epicatechin gallate+catechin gallate) is from 2 to 4.
- The “catechins” in the present invention means a collective term including epigallocatechin gallate (hereinafter referred to as EGCg), epigallocatechin (hereinafter referred to as EGC), epicatechin gallate (hereinafter referred to as ECg), epicatechin (hereinafter referred to as EC), gallocatechin gallate (hereinafter referred to as GCg), gallocatechin (hereinafter referred to as GC), catechin gallate (hereinafter referred to as Cg) and catechin (hereinafter referred to as C). Each of catechins described here may be either (+)-form or (−)-form, and (−)-EGCg, (−)-EGC, (−)-ECg, (−)-EC, (−)-GCg, (−)-GC, (−)-Cg and (+)-C are preferable.
- The tea polyphenol composition of the present invention related to claim 1 comprises the above-described catechins in a content of 85% by weight to 95% by weight, preferably 85.5% by weight to 94.5% by weight, more preferably 86% by weight to 94% by weight and further more preferably 86.5% by weight to 93.5% by weight. When the content of the catechins is within this range, a large amount of catechins can be readily ingested and the natural taste of tea can be obtained. The concentration of the catechins described here is defined based on the total amount of the eight kinds of compounds, EGCg, EGC, ECg, EC, GCg, GC, Cg and C.
- In the tea polyphenol composition of the present invention related to claim 1, in order for the excellent physiological effects of the catechins to be exerted more effectively, out of all the catechins the ratio of EGCg and GCg is required to be from 65% by weight to 80% by weight, preferably from 66% by weight to 79% by weight, more preferably from 67% by weight to 79% by weight and further more preferably from 68% by weight to 78.5% by weight.
- In the present invention related to claim 1, the value obtained by dividing the sum of the concentrations of EGCg and GCg by the sum of the concentrations of EC, C, EGC, GC, ECg and Cg is preferably from 2 to 4, more preferably from 2.1 to 3.9, further more preferably from 2.2 to 3.8 and most preferably from 2.3 to 3.7 in order to improve the taste of the catechins such as bitterness and astringency.
- As described in claim 2, in the present invention, the value obtained by dividing the sum of concentrations of EGCg, ECg, GCg and Cg (catechin gallate) by the sum of the concentrations of EC, EGC, GC and C (non-gallated catechins) is preferably from 3 to 7, more preferably from 3.1 to 6.8, further more preferably from 3.1 to 6.6 and most preferably from 3.2 to 6.4. This range is preferred because the excellent physiological effects of the catechins are readily exerted and because tastes such as bitterness and astringency are reduced.
- As described in claim 3, in the present invention, the value given by dividing the sum of the concentrations of EGCg and GCg by the sum of the concentrations of EC, EGC, GC and C (non-gallated catechins) is preferably from 2 to 6, more preferably from 2.5 to 5.9, further more preferably from 2.8 to 5.8 and most preferably from 2.9 to 5.6 in order to improve the taste of the catechins such as bitterness and astringency.
- As described in claim 4, in the present invention, the total content of GCg, GC, Cg and C (non-epimerized catechins) in the catechins is preferably from 2% by weight to 15% by weight, more preferably from 2.2% by weight to 13% by weight, further more preferably from 2.5% by weight to 11% by weight and most preferably from 2.7% by weight to 10.4% by weight in order to improve the flavor.
- As described in claim 5, in the tea polyphenol composition of the present invention, the weight ratio given by EGCg/(EC+EGC+ECg) is preferably from 2 to 4, more preferably from 2.2 to 3.9 and further more preferably from 2.1 to 3.8 in order to improve the taste of the catechins such as bitterness and astringency.
- As described in claim 6, in the tea polyphenol composition of the present invention, the content of caffeine is preferably from 0.0001% by weight to 1.2% by weight and more preferably from 0.001% by weight to 1.2% by weight. If the content of caffeine exceeds 1.2% by weight, dizziness, insomnia, palpitation, nausea or other symptoms could be caused due to the strong physiological effects of caffeine under some conditions of intake and of the person who takes it, and thus such a high caffeine content is not preferred.
- As described in claim 7, in the tea polyphenol composition of the present invention, the content of ash is preferably from 0.0001% by weight to 0.2% by weight and more preferably from 0.001% by weight to 0.2% by weight in order to improve the taste such as astringency and bitterness.
- As described in claim 8, in the present invention, it is preferred that gallic acid is not present in order to exert the excellent physiological effects of the catechins more effectively.
- In the present invention, the composition having all the requirements described in the above claims 1 to 8 and with improved tastes such as astringency and bitterness is preferred, and in particular the composition with a combination of the preferred ranges is more preferred.
- The tea polyphenol compositions described in claims 1 to 8, which are described above, can be produced, for example, by the method of the present invention related to claim 9.
- That is, the present invention related to claim 9 is a method for producing the tea polyphenol compositions described in claims 1 to 8 performed in the following steps 1) to 3):
- 1) A step in which tea components containing the catechins are extracted from tea leaves with hot water and further extracted with an organic solvent to provide a tea extract;
- 2) A step in which the tea extract is fed to a synthetic adsorption resin;
- 3) A step in which after the synthetic adsorption resin is washed with a 5% to 15% aqueous alcohol solution, the tea catechins is eluted by passing a 30% to 50% aqueous alcohol solution through the resin.
- The “tea polyphenol” in the present invention means an extract containing polyphenol(s) extracted from tea leaves or a purified polyphenolic compound.
- Here, “tea leaves” means leaves derived from a tea plant belonging to Theaceae (Camellia sinensis) and may include, regardless of being fermented or not, any one of fermented teas such as ready-made black tea and puer tea, semi-fermented tea such as oolong tea and Pao Chung tea and non-fermented tea such as green tea, pan-roasted green tea and roasted tea and it may be a mixture of two or more kinds of these.
- The amount of the polyphenol of the present invention may be determined by the colorimetric quantitative analysis method using iron tatarate, but measurement with reversed phase high performance liquid chromatography is preferred to determine the composition of the tea polyphenol in detail.
- The tea leaves used in the present invention may be raw or dried, but dried leaves are preferably used. When dried material is used, the tea leaves are dried and then crushed if necessary to provide the raw material for the extraction step. For example, such material can be prepared by drying the raw tea leaves followed by crushing or by cutting the raw tea leaves into small pieces followed by drying.
- The present invention related to claim 9 comprises the three steps, 1) to 3) mentioned above.
- The first step is a step in which tea components containing the catechins are extracted from the tea leaves with hot water and then further extracted with an organic solvent to provide a tea extract (extraction step).
- In this extraction step, the tea components containing the catechins are at first extracted from the above-described tea leaves with hot water. There is no defined limit for the temperature of the hot water used here as long as it is 100° C. or lower under atmospheric pressure. The temperature is preferably from 60° C. to 100° C., more preferably from 70° C. to 90° C. and most preferably from 80° C. to 85° C. If this extraction is done at a temperature over 100° C., structural conversions such as isomer polymerization of the catechins could take place, and thus such a high temperature is unfavorable, whereas if extracted below 60° C., the catechins are not fully extracted, thus such a low temperature is unfavorable. When extraction is performed under positive pressure, the catechins can be extracted at a temperature lower than that under atmospheric pressure, and the temperature on extraction may be adjusted as appropriate for the pressure applied. The amount of hot water for extraction from the tea leaves is, although not particularly limited to, preferably three to ten times, more preferably five to seven times that of the tea leaves by weight. If the amount of hot water used is less than three times that of the tea leaves by weight, the catechins cannot be sufficiently extracted, whereas use of hot water in an amount of more than ten times that of the tea leaves does not particularly improve the extraction efficiency. Extraction with hot water may be performed either only once or repeatedly two or more times but it is preferred to extract twice. When extraction is performed twice, the amounts of hot water used are, although not particularly limited to, preferably seven times that of the tea leaves by weight in the first extraction and five times that of the tea leaves by weight in the second extraction.
- The liquid extract obtained by the above-described extraction with hot water is cooled once. The temperature on cooling is preferably 50° C. or lower, more preferably 30° C. or lower and most preferably 15° C. or lower. If the temperature on cooling exceeds 50° C., insoluble components cannot be fully removed in centrifugal filtration in a later step, and thus such a condition is not favored.
- Next, the cooled extracted liquid is concentrated. The method for concentration may be any of methods generally used, for example, vacuum concentration method, atmospheric concentration method, heating concentration method, batch concentration method, membrane concentration method and circulation concentration method. The membrane concentration method, in particular, the membrane concentration method with a reverse osmosis (RO) membrane is preferably used. Filter filtration, centrifugal filtration or the like may be run prior to concentration without any problem.
- In the first step, as described above, the tea components containing the catechins are extracted from the tea leaves with hot water, and the liquid extract obtained is preferably cooled and then concentrated, thereby yielding a concentrated liquid, which is further extracted with an organic solvent.
- The organic solvent used here includes an organic solvent that can dissolve the tea polyphenol, for example, acetonitrile, methanol, ethanol, ethyl acetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, tetrahydrofuran or dioxane, hydrous organic solvent thereof and a mixed solvent of these organic solvents. Among these, ethyl acetate is preferably used. The amount of the organic solvent is preferably a half to five times, more preferably one to three times, most preferably one and a half to two times that of the concentrated liquid by volume. If the volume of the organic solvent is less than a half of the concentrated liquid, the catechins cannot be fully extracted, whereas if the volume exceeds five times that of the concentrated liquid, the extraction efficiency is not particularly improved.
- Then the organic solvent layer obtained is concentrated. The concentration method used here may be any of methods generally used including, for example, vacuum concentration method, atmospheric concentration method, heating concentration method, batch concentration method, membrane concentration method or circulation concentration method. A combination of any of the above-mentioned methods may be also used, and a combination of vacuum concentration method, heating concentration method and circulation concentration method is particularly preferred.
- The above-described concentrated liquid is dried to obtain a tea extract (crude tea extract). The drying method is, although not particularly limited to, preferably spray drying method, freeze drying method, vacuum drying method or the like. A commercial product may be also used as a crude tea extract without any problem.
- The second step is a step to feed the tea extract (crude tea extract) obtained in the first step to a synthetic adsorption resin.
- In this second step, at first, the crude tea extract obtained is dissolved preferably in a 5% to 15% aqueous alcohol solution, more preferably in a 10% aqueous alcohol solution and further more preferably in a 10% aqueous methanol solution, and then the resultant solution is fed to a synthetic adsorption resin to adsorb tea extract components.
- The synthetic adsorption resin used is preferably crosslinked styrenic type, including, for example, HP-20 (Diaion, manufactured by Mitsubishi Chemical Corporation), Sepabeads (manufactured by Mitsubishi Chemical Corporation), Amberlite (manufactured by Organo Corporation), Shodex (manufactured by Showa Denko K.K.) and Sephadex (manufactured by Pharmacia Fine Chemicals AB).
- The third step is a step in which the synthetic adsorption resin is washed with a 5% to 15% aqueous alcohol solution and then the tea catechins are eluted by passing a 30% to 50% aqueous alcohol solution through the resin.
- In this third step, wherein the catechins are eluted by passing a 30 to 50% aqueous alcohol solution, unadsorbed components are washed out before the elution with the 30% to 50% aqueous alcohol solution.
- That is, the synthetic adsorption resin is at first washed with a 5% to 15% aqueous alcohol solution to wash out the unadsorbed components. The concentration of the aqueous alcohol solution used here may be from 5% to 15% and preferably 10%. A volume of 50 L or more is sufficient as the amount of the aqueous alcohol solution to be passed through a column with a capacity of 300 L.
- After this washing, a 30% to 50% aqueous alcohol solution is passed through to elute the tea catechins. The kind of the aqueous alcohol solution used here is, although not restricted, preferably an aqueous methanol solution. The concentration of the aqueous alcohol solution may be from 30% to 50%, and is preferably from 35% to 45% and more preferably 40%. Therefore, a 40% aqueous methanol solution is preferably used to elute the tea catechins. The volume of the aqueous alcohol solution passed through a column with a capacity of 300 L is 100 L or more and preferably 280±56 L.
- Finally, it is preferred to remove insoluble components such as caffeine by washing with an aqueous alcohol solution. The kind of the aqueous alcohol solution used here is, although not restricted, preferably an aqueous methanol solution. The concentration of the aqueous alcohol solution may be from 50% to 100% and is preferably from 60% to 80% and more preferably 70%. The volume of the aqueous alcohol passed through a column with a capacity of 300 L is 100 L or more, preferably 400 L or more and further preferably 600 L or more.
- It is advisable that recovery of the tea catechin fraction starts at a time when the content of (−)-EGCg has reached a level twice or more, preferably five times or more, as high as that of (−)-EGC and ends at a time when the content of (−)-EGCg has reached a level lower than that of (−)-ECg or at a time when the content of caffeine becomes 5%, preferably 1%. If the timing to start the recovery is set earlier than the above timing, the content of (−)-EGCg decreases, whereas if the timing to end the recovery is later than the above timing, the content of (−)-EGCg decreases and the content of caffeine increases.
- The tea polyphenol composition of the present invention is obtained by concentrating and drying the tea catechin fraction obtained in the above steps. The concentration method may be any of the methods generally used including, for example, vacuum concentration method, atmospheric concentration method, heating concentration method, batch concentration method, membrane concentration method, circulation concentration method or the like. A combination of a any of the above-mentioned concentration methods may be also used and a combination of vacuum concentration method, heating concentration method and circulation concentration method is preferred in particular. There is no particular set drying method, but spray drying method, freeze drying method, vacuum drying method and the like may be favorably used.
- In the tea polyphenol composition hereby obtained, tastes peculiar to the catechins, such as bitterness and astringency, are substantially reduced.
- Furthermore, this tea polyphenol composition can be expected to contribute to imparting the primary effects of the polyphenol, for example, physiological functions, such as antioxidative effect, antimicrobial and bacteriostatic effects, inhibitory action on cholesterol increase, inhibitory action on blood pressure increase and an inhibitory action on blood glucose increase, without fear of the negative effects of caffeine described hereinafter because the composition has a high content of the tea catechins with a gallate group and almost no caffeine or gallic acid content. Caffeine is known to have physiological activities such as an excitatory activity on the central nervous system, a positive inotropic effect and a diuretic effect. Under some conditions of the intake and of the person who takes it, dizziness, insomnia, palpitation, nausea or other symptoms might be caused due to strong physiological effects of caffeine, so that people hypersensitive to caffeine may regard intake of caffeine problematic.
- Since the tea polyphenol composition of the present invention is chemically, physically and biologically very stable, the field of its application is not limited, and it can be added to, for example, food and drink, pharmaceuticals, quasi drugs, cosmetics, textiles or the like. According to the application, the product of the present invention may be used together with a vitamin such as tocopherol or vitamin C, an antimicrobial or bactericidal agent, a coloring matter, an aroma agent, a bulking agent, a coating agent or the like.
- Examples, comparative examples and test examples are illustrated below to describe the present invention in more detail. However, the present invention is not restricted by these examples.
- Two hundred and seventy kilograms of dried green tea leaves was subjected to extraction with 1890 L of hot water at 80° C. and then to additional extraction with 1350 L of hot water at 80° C. This liquid extract was cooled to a temperature of 15° C. or lower, and then concentrated using an RO membrane to obtain 500 L of a concentrated liquid. This concentrated liquid was extracted with 1000 L of ethyl acetate, the ethyl acetate layer was concentrated to 75 kg, and the concentrated solution was dried to obtain 15 kg of a crude tea extract.
- Twelve kilograms of the crude tea extract hereby obtained was used as a raw material. This tea extract was dissolved in 22 L of a 10% aqueous methanol solution and the resultant solution was added to 300 L of a crosslinked styrenic synthetic adsorption resin (HP-20, manufactured by Mitsubishi Chemical Corporation) to adsorb components in the tea extract.
- After the unadsorbed components were removed by passing 280 L of a 10% aqueous methanol solution through the resin, the tea catechin fraction was eluted with 280 L of a 40% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 70% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 1 in the present invention.
- Ingredients in the tea polyphenol composition (Product 1 of present invention) hereby obtained were analyzed with high performance liquid chromatography under conditions given below. Composition of this tea polyphenol composition is shown in Table 1.
- [Condition of High Performance Liquid Chromatography]
- Column: Mightysil (manufactured by Kanto Chemical Co., Inc.)
- Mobile phase solution A: A solution containing acetonitrile and aqueous phosphoric acid solution with a ratio of 10:400
- Mobile phase solution B: A solution containing methanol, acetonitrile and aqueous phosphoric acid solution with a ratio of 200:10:400
- Detection: UV at 230 nm
- Column temperature: 40° C.
- Sample temperature: room temperature
- Sample volume: 10 μL
- Flow rate: 1 mL/min
- Two hundred and seventy kilograms of dried green tea leaves was subjected to extraction with 1890 L of hot water at 80° C. and then to additional extraction with 1350 L of hot water at 80° C. This liquid extract was cooled to a temperature of 15° C. or lower, and then concentrated using an RO membrane to obtain 500 L of a concentrated liquid. This concentrated liquid was extracted with 1000 L of ethyl acetate, the ethyl acetate layer was concentrated to 75 kg, and the concentrated solution was dried to obtain 15 kg of a crude tea extract.
- Twelve kilograms of the crude tea extract hereby obtained was used as a raw material. This tea extract was dissolved in 22 L of a 10% aqueous methanol solution and the resultant solution was added to 300 L of a crosslinked styrenic synthetic adsorption resin (HP-20, manufactured by Mitsubishi Chemical Corporation) to adsorb components in the tea extract.
- After the unadsorbed components were removed by passing 280 L of a 10% aqueous methanol solution through the resin, the tea catechin fraction was eluted with 280 L of a 35% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 70% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 2 in the present invention.
- Ingredients in the tea polyphenol composition (Product 2 in the present invention) hereby obtained were analyzed similarly to Example 1. The results are given in Table 1.
- Two hundred and seventy kilograms of dried green tea leaves was subjected to extraction with 1890 L of hot water at 80° C. and then to additional extraction with 1350 L of hot water at 80° C. This liquid extract was cooled to a temperature of 15° C. or lower, and then concentrated using an RO membrane to obtain 500 L of a concentrated liquid. This concentrated liquid was extracted with 1000 L of ethyl acetate, the ethyl acetate layer was concentrated to 75 kg, and the concentrated solution was dried to obtain 15 kg of a crude tea extract.
- Twelve kilograms of the crude tea extract hereby obtained was used as a raw material. This tea extract was dissolved in 22 L of a 10% aqueous methanol solution and the resultant solution was added to 300 L of a crosslinked styrenic synthetic adsorption resin (HP-20, manufactured by Mitsubishi Chemical Corporation) to adsorb components in the tea extract.
- After the unadsorbed components were removed by passing 280 L of a 5% aqueous methanol solution through the resin, the tea catechin fraction was eluted with 280 L of a 35% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 70% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 3 in the present invention.
- Ingredients in the tea polyphenol composition (Product 3 in the present invention) hereby obtained were analyzed similarly to Example 1. The results are given in Table 1.
- Two hundred and seventy kilograms of dried green tea leaves was subjected to extraction with 1890 L of hot water at 80° C. and then to additional extraction with 1350 L of hot water at 80° C. This liquid extract was cooled to a temperature of 15° C. or lower, and then concentrated using an RO membrane to obtain 500 L of a concentrated liquid. This concentrated liquid was extracted with 1000 L of ethyl acetate, the ethyl acetate layer was concentrated to 75 kg, and the concentrated solution was dried to obtain 15 kg of a crude tea extract.
- Twelve kilograms of the crude tea extract hereby obtained was used as a raw material. This tea extract was dissolved in 22 L of a 10% aqueous methanol solution and the resultant solution was added to 300 L of a crosslinked styrenic synthetic adsorption resin (HP-20, manufactured by Mitsubishi Chemical Corporation) to adsorb components in the tea extract.
- After the unadsorbed components were removed by passing 280 L of a 10% aqueous methanol solution through the resin, the tea catechin fraction was eluted with 280 L of a 45% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 65% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 4 in the present invention.
- Ingredients in the tea polyphenol composition (Product 4 in the present invention) hereby obtained were analyzed similarly to Example 1. The results are given in Table 1.
- Two hundred and seventy kilograms of dried green tea leaves was subjected to extraction with 1890 L of hot water at 80° C. and then to additional extraction with 1350 L of hot water at 80° C. This liquid extract was cooled to a temperature of 15° C. or lower, and then concentrated using an RO membrane to obtain 500 L of a concentrated liquid. This concentrated liquid was extracted with 1000 L of ethyl acetate, the ethyl acetate layer was concentrated to 75 kg, and the concentrated solution was dried to obtain 15 kg of a crude tea extract.
- Twelve kilograms of the crude tea extract hereby obtained was used as a raw material. This tea extract was dissolved in 22 L of a 10% aqueous methanol solution and the resultant solution was added to 300 L of a crosslinked styrenic synthetic adsorption resin (HP-20, manufactured by Mitsubishi Chemical Corporation) to adsorb components in the tea extract.
- After the unadsorbed components were removed by passing 280 L of a 15% aqueous methanol solution through the resin, the tea catechin fraction was eluted with 280 L of a 35% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 70% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 5 in the present invention.
- Ingredients in the tea polyphenol composition (Product 5 in the present invention) hereby obtained were analyzed similarly to Example 1. The results are given in Table 1.
- Two hundred and seventy kilograms of dried green tea leaves was subjected to extraction with 1890 L of hot water at 80° C. and then to additional extraction with 1350 L of hot water at 80° C. This liquid extract was cooled to a temperature of 15° C. or lower, and then concentrated using an RO membrane to obtain 500 L of a concentrated liquid. This concentrated liquid was extracted with 1000 L of ethyl acetate, the ethyl acetate layer was concentrated to 75 kg, and the concentrated solution was dried to obtain 15 kg of a crude tea extract.
- Twelve kilograms of the crude tea extract hereby obtained was used as a raw material. This tea extract was dissolved in 22 L of a 10% aqueous methanol solution and the resultant solution was added to 300 L of a crosslinked styrenic synthetic adsorption resin (HP-20, manufactured by Mitsubishi Chemical Corporation) to adsorb components in the tea extract.
- After the unadsorbed components were removed by passing 280 L of a 15% aqueous methanol solution through the resin, the tea catechin fraction was eluted with 280 L of a 40% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 65% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 6 in the present invention.
- Ingredients in the tea polyphenol composition (Product 6 in the present invention) hereby obtained were analyzed similarly to Example 1. The results are given in Table 2.
- Two hundred and seventy kilograms of dried green tea leaves was subjected to extraction with 1890 L of hot water at 80° C. and then to additional extraction with 1350 L of hot water at 80° C. This liquid extract was cooled to a temperature of 15° C. or lower, and then concentrated using an RO membrane to obtain 500 L of a concentrated liquid. This concentrated liquid was extracted with 1000 L of ethyl acetate, the ethyl acetate layer was concentrated to 75 kg, and the concentrated solution was dried to obtain 15 kg of a crude tea extract.
- Twelve kilograms of the crude tea extract hereby obtained was used as a raw material. This tea extract was dissolved in 22 L of a 10% aqueous methanol solution and the resultant solution was added to 300 L of a crosslinked styrenic synthetic adsorption resin (HP-20, manufactured by Mitsubishi Chemical Corporation) to adsorb components in the tea extract.
- After the unadsorbed components were removed by passing 280 L of a 15% aqueous methanol solution through the resin, the tea catechin fraction was eluted with 280 L of a 40% aqueous methanol solution. Subsequently insoluble components were washed out and removed by passing 600 L of a 75% aqueous methanol solution through the resin. Approximately 240 L of a tea catechin fraction was recovered. This fraction was subjected to circulation concentration with a centrifugal thin-film evaporator (manufactured by Okawara Mfg. Co., Ltd.) to obtain approximately 20 L of a concentrated liquid. This concentrated liquid was spray-dried with a spray dryer (manufactured by Niro A/S) to obtain 4.8 kg of a tea polyphenol composition, which was designated as Product 7 in the present invention.
- Ingredients in the tea polyphenol composition (Product 7 in the present invention) hereby obtained were analyzed similarly to Example 1. The results are given in Table 2.
- Commercial products were used.
- That is, commercial polyphenol preparations “Polyphenon 70A” (manufactured by Mitsui Norin Co., Ltd.), “Polyphenon 60B” (manufactured by Mitsui Norin Co., Ltd.) and pure epigallocatechin gallate were used in Comparative Example 1 (Comparative Product 1), Comparative Example 2 (Comparative Product 2) and Comparative Example 3 (Comparative Product 3), respectively.
- Ingredients in these tea polyphenol compositions (Comparative Products 1 to 3) were analyzed similarly to Example 1. The results are shown in Table 2.
- Bitterness and astringency of the tea polyphenol compositions obtained in Examples 1 to 7 and Comparative Examples 1 to 3 were examined according to the following test method. The results are shown in Tables 1 and 2.
- [Test Method]
- Sensory evaluation was conducted with ten men and women randomly chosen as panelists.
- Each sample of Products 1 to 7 in the present invention obtained in the examples and Comparative Products 1 to 3 was added to 800 g of ion-exchanged water so that the catechin content was 1 g. To this solution, 0.3 g of sodium ascorbate and an appropriate amount of a 5% aqueous sodium bicarbonate solution were added to adjust pH to 6.2 and the solution was further diluted with ion-exchanged water to adjust the total amount to 1000 g to prepare a test solution. The products in the present invention were compared with the comparative products to evaluate whether the bitterness and astringency were reduced or not. Evaluation of bitterness and astringency was rated in five levels described below. After evaluation of one sample of the test and comparative solutions, the mouth was rinsed with warm water, and next evaluation was conducted after 30 min or later.
- [Rating Criteria for Evaluation]
Very strong bitterness and astringency 5 Strong bitterness and astringency 4 Weak bitterness and astringency 3 Some bitterness and astringency 2 No bitterness and astringency 1 -
TABLE 1 Product Product Product Product Product 1 in 2 in 3 in 4 in 5 in present present present present present invention invention invention invention invention EGCg % by weight 64.6 61.1 59.7 66.9 61.2 EC % by weight 9.7 11.2 11.5 9.0 9.4 EGC % by weight 5.0 5.0 7.6 4.5 1.8 ECg % by weight 5.8 5.9 5.4 4.5 9.1 GC % by weight 0.5 0.3 0.6 0.3 0.2 GCg % by weight 6.3 3.7 3.7 3.7 7.5 Cg % by weight 0.3 0.2 0.2 0.0 0.5 C % by weight 1.3 1.5 1.7 1.1 0.9 All the catechins % by weight 93.5 88.9 90.4 90.0 90.6 (EGCg + GCg)/All the catechins % by weight 75.83 72.89 70.13 78.44 75.83 (EGCg + GCg)/(EC + EGC + ECg + C + 3.14 2.69 2.35 3.64 3.14 GC + Cg) (EGCg + ECg + GCg + Cg)/(EC + EGC + 4.67 3.94 3.22 5.04 6.37 C + GC) (EGCg + GCg)/(EC + EGC + C + GC) 4.30 3.60 2.96 4.74 5.59 (GC + GCg + C + Cg)/All the catechins % by weight 8.98 6.41 6.86 5.67 10.04 EGCg/(EC + EGC + ECg) 3.15 2.76 2.44 3.72 3.01 Caffeine % by weight 0.6 0.5 0.9 0.4 0.4 Ash % by weight 0.1 0.1 0.1 0.1 0.1 Gallic acid % by weight 0.0 0.0 0.0 0.0 0.0 Rating of bitterness and astringency 2.4 2.1 2.2 2.4 2.3 -
TABLE 2 Product Product 6 in 7 in present present Comparative Comparative Comparative invention invention Product 1 Product 2 Product 3 EGCg % by weight 67.1 61.1 56.1 34.9 100.0 EC % by weight 11.0 9.1 2.8 4.7 — EGC % by weight 5.2 3.3 3.6 8.4 — ECg % by weight 5.3 7.5 12.6 8.9 — GC % by weight 0.1 0.3 0.9 1.4 — GCg % by weight 1.5 7.4 3.4 1.5 — Cg % by weight 0.0 0.4 0.4 0.4 — C % by weight 0.9 1.2 0.8 0.7 — All the catechins % by weight 91.1 90.3 80.6 60.9 100.0 (EGCg + GCg)/All the catechins % by weight 75.30 75.86 73.82 59.77 — (EGCg + GCg)/(EC + EGC + ECg + C + 3.05 3.14 2.82 1.49 — GC + Cg) (EGCg + ECg + GCg + Cg)/(EC + EGC + 4.30 5.50 8.95 3.01 — C + GC) (EGCg + GCg)/(EC + EGC + C + GC) 3.99 4.93 7.35 2.39 — (GC + GCg + C + Cg)/All the catechins % by weight 2.74 10.30 6.82 6.57 — EGCg/(EC + EGC + ECg) 3.12 3.07 2.95 1.59 — Caffeine % by weight 0.7 0.4 0.4 0.4 — Ash % by weight 0.1 0.1 0.1 0.1 — Gallic acid % by weight 0.0 0.0 0.0 0.0 — Rating of bitterness and astringency 2.4 2.3 4.3 4.5 4.5 - As shown in Tables 1 and 2, it is clear that Products 1 to 7 in the present invention are less bitter and astringent than Comparative Products 1 to 3.
Claims (12)
1. A tea polyphenol composition, (A) comprising 85% by weight to 95% by weight of catechins, (B) wherein the catechins contains epigallocatechin gallate and gallocatechin gallate at a ratio of 65% by weight to 80% by weight with respect to the total amount of all the catechins and (C) wherein the ratio given by (epigallocatechin gallate+gallocatechin gallate)/(epicatechin+catechin+epigallocatechin+gallocatechin+epicatechin gallate+catechin gallate) is from 2 to 4.
2. The tea polyphenol composition according to claim 1 , wherein the ratio given by (epigallocatechin gallate+epicatechin gallate+gallocatechin gallate+catechin gallate)/(epicatechin+epigallocatechin+gallocatechin+catechin) is from 3 to 7.
3. The tea polyphenol composition according to claim 1 , wherein the ratio given by (epigallocatechin gallate+gallocatechin gallate)/(epicatechin+epigallocatechin+gallocatechin+catechin) is from 2 to 6.
4. The tea polyphenol composition according to claim 1 , wherein the catechins contains gallocatechin gallate, gallocatechin, catechin gallate and catechin at a ratio of 2% by weight to 15% by weight with respect to the total amount of all the catechins.
5. The tea polyphenol composition according to claim 1 , wherein the ratio given by epigallocatechin gallate/(epicatechin+epigallocatechin+epicatechin gallate) is from 2 to 4.
6. The tea polyphenol composition according to claim 1 , further comprising 0.0001% by weight to 1.2% by weight of caffeine.
7. The tea polyphenol composition according to claim 1 , further comprising 0.0001% by weight to 0.2% by weight of ash.
8. The tea polyphenol composition according to claim 1 , not comprising gallic acid.
9. A method for producing the tea polyphenol composition according to claim 1 comprising the following steps (1) to (3):
(1) extracting tea components which contain catechins from tea leaves with hot water, and carrying out a further extraction with an organic solvent to provide a tea extract;
(2) feeding the tea extract to a synthetic adsorption resin; and
(3) washing the synthetic adsorption resin with a 5% to 15% aqueous alcohol solution, and then eluting the tea catechins by passing a 30% to 50% aqueous alcohol solution through the resin.
10. A method for producing the tea polyphenol composition according to claim 2 comprising the following steps (1) to (3):
(1) extracting tea components which contain catechins from tea leaves with hot water, and carrying out a further extraction with an organic solvent to provide a tea extract;
(2) feeding the tea extract to a synthetic adsorption resin; and
(3) washing the synthetic adsorption resin with a 5% to 15% aqueous alcohol solution, and then eluting the tea catechins by passing a 30% to 50% aqueous alcohol solution through the resin.
11. A method for producing the tea polyphenol composition according to claim 3 comprising the following steps (1) to (3):
(1) extracting tea components which contain catechins from tea leaves with hot water, and carrying out a further extraction with an organic solvent to provide a tea extract;
(2) feeding the tea extract to a synthetic adsorption resin; and
(3) washing the synthetic adsorption resin with a 5% to 15% aqueous alcohol solution, and then eluting the tea catechins by passing a 30% to 50% aqueous alcohol solution through the resin.
12. A method for producing the tea polypnenol composition according to claim 5 comprising the following steps (1) to (3):
(1) extracting tea components which contain catechins from tea leaves with hot water, and carrying out a further extraction with an organic solvent to provide a tea extract;
(2) feeding the tea extract to a synthetic adsorption resin; and
(3) washing the synthetic adsorption resin with a 5% to 15% aqueous alcohol solution, and then eluting the tea catechins by passing a 30% to 50% aqueous alcohol solution through the resin.
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US12/631,504 US7763291B2 (en) | 2004-07-22 | 2009-12-04 | Tea polyphenol composition and method for producing the same |
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JP2004214370A JP4702824B2 (en) | 2004-07-22 | 2004-07-22 | Tea polyphenol composition and method for producing the same |
PCT/JP2004/012052 WO2006008833A1 (en) | 2004-07-22 | 2004-08-23 | Tea polyphenol composition and process for producing the same |
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US12/631,504 Active US7763291B2 (en) | 2004-07-22 | 2009-12-04 | Tea polyphenol composition and method for producing the same |
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US (2) | US20070292544A1 (en) |
EP (1) | EP1770090B1 (en) |
JP (1) | JP4702824B2 (en) |
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WO (1) | WO2006008833A1 (en) |
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US20100021615A1 (en) * | 2006-12-28 | 2010-01-28 | Kao Corporation | Tea extract |
US20100136205A1 (en) * | 2007-05-24 | 2010-06-03 | Kao Corporation | Purified green tea extract |
CN112889939A (en) * | 2020-12-14 | 2021-06-04 | 皖西学院 | Process for preparing tea polyphenol |
CN113170830A (en) * | 2021-05-11 | 2021-07-27 | 汪健 | Catechin beverage |
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KR101436645B1 (en) | 2006-03-02 | 2014-09-01 | 카오카부시키가이샤 | Process for producing purified tea extract |
PL1891862T3 (en) * | 2006-07-24 | 2012-08-31 | Unilever Nv | Beverage precursor |
JP4866815B2 (en) * | 2007-09-05 | 2012-02-01 | 花王株式会社 | Method for producing purified green tea extract |
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KR20190048502A (en) | 2017-10-31 | 2019-05-09 | (주)아모레퍼시픽 | Composition for improving circulatory diseases comprising tea extraction which has modified amount of ingredients |
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Also Published As
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JP4702824B2 (en) | 2011-06-15 |
EP1770090B1 (en) | 2016-07-20 |
EP1770090A1 (en) | 2007-04-04 |
US7763291B2 (en) | 2010-07-27 |
WO2006008833A1 (en) | 2006-01-26 |
US20100069429A1 (en) | 2010-03-18 |
ES2586417T3 (en) | 2016-10-14 |
EP1770090A4 (en) | 2008-01-16 |
JP2006036645A (en) | 2006-02-09 |
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