NO971485L - Antineoplastiske kakao-ekstrakter, fremgangsmåter for fremstilling og anvendelse - Google Patents
Antineoplastiske kakao-ekstrakter, fremgangsmåter for fremstilling og anvendelse Download PDFInfo
- Publication number
- NO971485L NO971485L NO971485A NO971485A NO971485L NO 971485 L NO971485 L NO 971485L NO 971485 A NO971485 A NO 971485A NO 971485 A NO971485 A NO 971485A NO 971485 L NO971485 L NO 971485L
- Authority
- NO
- Norway
- Prior art keywords
- cocoa
- procyanidin
- extract
- beans
- polyphenols
- Prior art date
Links
- 235000009470 Theobroma cacao Nutrition 0.000 title claims description 180
- 238000000034 method Methods 0.000 title claims description 74
- 239000000284 extract Substances 0.000 title claims description 65
- 230000000118 anti-neoplastic effect Effects 0.000 title claims description 32
- 238000002360 preparation method Methods 0.000 title description 7
- 244000240602 cacao Species 0.000 title 1
- 244000299461 Theobroma cacao Species 0.000 claims description 182
- 229920002414 procyanidin Polymers 0.000 claims description 122
- CWEZAWNPTYBADX-UHFFFAOYSA-N Procyanidin Natural products OC1C(OC2C(O)C(Oc3c2c(O)cc(O)c3C4C(O)C(Oc5cc(O)cc(O)c45)c6ccc(O)c(O)c6)c7ccc(O)c(O)c7)c8c(O)cc(O)cc8OC1c9ccc(O)c(O)c9 CWEZAWNPTYBADX-UHFFFAOYSA-N 0.000 claims description 121
- XFZJEEAOWLFHDH-UHFFFAOYSA-N (2R,2'R,3R,3'R,4R)-3,3',4',5,7-Pentahydroxyflavan(48)-3,3',4',5,7-pentahydroxyflavan Natural products C=12OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C(O)C=C(O)C=1C(C1=C(O)C=C(O)C=C1O1)C(O)C1C1=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UHFFFAOYSA-N 0.000 claims description 70
- MOJZMWJRUKIQGL-FWCKPOPSSA-N Procyanidin C2 Natural products O[C@@H]1[C@@H](c2cc(O)c(O)cc2)Oc2c([C@H]3[C@H](O)[C@@H](c4cc(O)c(O)cc4)Oc4c3c(O)cc(O)c4)c(O)cc(O)c2[C@@H]1c1c(O)cc(O)c2c1O[C@@H]([C@H](O)C2)c1cc(O)c(O)cc1 MOJZMWJRUKIQGL-FWCKPOPSSA-N 0.000 claims description 70
- HGVVOUNEGQIPMS-UHFFFAOYSA-N procyanidin Chemical compound O1C2=CC(O)=CC(O)=C2C(O)C(O)C1(C=1C=C(O)C(O)=CC=1)OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 HGVVOUNEGQIPMS-UHFFFAOYSA-N 0.000 claims description 70
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 59
- 235000013824 polyphenols Nutrition 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 42
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 32
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 32
- 239000002246 antineoplastic agent Substances 0.000 claims description 30
- 239000003963 antioxidant agent Substances 0.000 claims description 25
- 235000006708 antioxidants Nutrition 0.000 claims description 25
- 239000000843 powder Substances 0.000 claims description 25
- 229940119429 cocoa extract Drugs 0.000 claims description 24
- 230000003078 antioxidant effect Effects 0.000 claims description 23
- 229940034982 antineoplastic agent Drugs 0.000 claims description 20
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-ol Natural products C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 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 description 9
- 229930013783 (-)-epicatechin Natural products 0.000 claims description 9
- 235000007355 (-)-epicatechin Nutrition 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 101710183280 Topoisomerase Proteins 0.000 claims description 8
- 238000004108 freeze drying Methods 0.000 claims description 8
- XFZJEEAOWLFHDH-NFJBMHMQSA-N procyanidin B2 Chemical compound C1([C@@H]2[C@H](O)[C@H](C3=C(O)C=C(O)C=C3O2)C=2C(O)=CC(O)=C3C[C@H]([C@H](OC3=2)C=2C=C(O)C(O)=CC=2)O)=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-NFJBMHMQSA-N 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 7
- 238000001641 gel filtration chromatography Methods 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 7
- 238000005238 degreasing Methods 0.000 claims description 5
- 229920002350 Procyanidin B2 Polymers 0.000 claims description 4
- GMISZFQPFDAPGI-HZZPXJBDSA-N Procyanidin B5 Natural products C1([C@@H]2[C@H](O)[C@@H](C3=C(O)C=C(O)C=C3O2)C=2C(O)=C3C[C@H]([C@H](OC3=CC=2O)C=2C=C(O)C(O)=CC=2)O)=CC=C(O)C(O)=C1 GMISZFQPFDAPGI-HZZPXJBDSA-N 0.000 claims description 4
- MOJZMWJRUKIQGL-FQVWZTFVSA-N Procyanidin C1 Natural products O[C@H]1[C@@H](c2cc(O)c(O)cc2)Oc2c([C@@H]3[C@@H](O)[C@@H](c4cc(O)c(O)cc4)Oc4c3c(O)cc(O)c4)c(O)cc(O)c2[C@H]1c1c(O)cc(O)c2c1O[C@H]([C@H](O)C2)c1cc(O)c(O)cc1 MOJZMWJRUKIQGL-FQVWZTFVSA-N 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 4
- NSEWTSAADLNHNH-UHFFFAOYSA-N pavetannin A-2 Natural products OC1CC2=C(O)C=C3OC(C4O)(C=5C=C(O)C(O)=CC=5)OC5=CC(O)=CC(O)=C5C4C3=C2OC1C1=CC=C(O)C(O)=C1 NSEWTSAADLNHNH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002953 preparative HPLC Methods 0.000 claims description 4
- NSEWTSAADLNHNH-LSBOWGMISA-N proanthocyanidin A2 Chemical compound C1([C@H]2OC3=C4[C@H]5C6=C(O)C=C(O)C=C6O[C@]([C@@H]5O)(OC4=CC(O)=C3C[C@H]2O)C=2C=C(O)C(O)=CC=2)=CC=C(O)C(O)=C1 NSEWTSAADLNHNH-LSBOWGMISA-N 0.000 claims description 4
- GMISZFQPFDAPGI-UHFFFAOYSA-N proanthocyanidin B5 Natural products OC=1C=C2OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C(O)C=1C(C1=C(O)C=C(O)C=C1O1)C(O)C1C1=CC=C(O)C(O)=C1 GMISZFQPFDAPGI-UHFFFAOYSA-N 0.000 claims description 4
- GMISZFQPFDAPGI-CVJZBMGUSA-N procyanidin B5 Chemical compound C1([C@@H]2[C@H](O)[C@H](C3=C(O)C=C(O)C=C3O2)C=2C(O)=C3C[C@H]([C@H](OC3=CC=2O)C=2C=C(O)C(O)=CC=2)O)=CC=C(O)C(O)=C1 GMISZFQPFDAPGI-CVJZBMGUSA-N 0.000 claims description 4
- MOJZMWJRUKIQGL-XILRTYJMSA-N procyanidin C1 Chemical compound C1([C@@H]2[C@H](O)[C@H](C3=C(O)C=C(O)C=C3O2)C2=C3O[C@@H]([C@H](O)[C@H](C3=C(O)C=C2O)C=2C(O)=CC(O)=C3C[C@H]([C@H](OC3=2)C=2C=C(O)C(O)=CC=2)O)C=2C=C(O)C(O)=CC=2)=CC=C(O)C(O)=C1 MOJZMWJRUKIQGL-XILRTYJMSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000010903 husk Substances 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 description 117
- 230000000694 effects Effects 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 231100000673 dose–response relationship Toxicity 0.000 description 43
- 102000007537 Type II DNA Topoisomerases Human genes 0.000 description 27
- 108010046308 Type II DNA Topoisomerases Proteins 0.000 description 27
- 230000001093 anti-cancer Effects 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 206010028980 Neoplasm Diseases 0.000 description 23
- 230000000259 anti-tumor effect Effects 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 238000002835 absorbance Methods 0.000 description 21
- 201000011510 cancer Diseases 0.000 description 19
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 238000003556 assay Methods 0.000 description 16
- 108020003631 Kinetoplast DNA Proteins 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- 102100020870 La-related protein 6 Human genes 0.000 description 13
- 108050008265 La-related protein 6 Proteins 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 12
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 11
- 230000004083 survival effect Effects 0.000 description 11
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 10
- 238000011894 semi-preparative HPLC Methods 0.000 description 10
- 206010006187 Breast cancer Diseases 0.000 description 9
- 208000026310 Breast neoplasm Diseases 0.000 description 9
- 108020004414 DNA Proteins 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000012216 screening Methods 0.000 description 9
- 239000000287 crude extract Substances 0.000 description 8
- 201000001117 malignant triton tumor Diseases 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 208000000389 T-cell leukemia Diseases 0.000 description 7
- 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 description 7
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 6
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 6
- 229960001948 caffeine Drugs 0.000 description 6
- 230000001472 cytotoxic effect Effects 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 201000001441 melanoma Diseases 0.000 description 6
- 230000036961 partial effect Effects 0.000 description 6
- 229960004559 theobromine Drugs 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 5
- 102000030523 Catechol oxidase Human genes 0.000 description 5
- 108010031396 Catechol oxidase Proteins 0.000 description 5
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 5
- 229940009456 adriamycin Drugs 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 210000000481 breast Anatomy 0.000 description 5
- 210000001072 colon Anatomy 0.000 description 5
- 231100000433 cytotoxic Toxicity 0.000 description 5
- 231100000135 cytotoxicity Toxicity 0.000 description 5
- 230000003013 cytotoxicity Effects 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- 238000003359 percent control normalization Methods 0.000 description 5
- 230000008439 repair process Effects 0.000 description 5
- 230000033616 DNA repair Effects 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000004305 normal phase HPLC Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229930013915 (+)-catechin Natural products 0.000 description 3
- 235000007219 (+)-catechin Nutrition 0.000 description 3
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 3
- 206010008342 Cervix carcinoma Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 206010060862 Prostate cancer Diseases 0.000 description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 3
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 description 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 3
- 239000011543 agarose gel Substances 0.000 description 3
- 230000003217 anti-cancerogenic effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 201000010881 cervical cancer Diseases 0.000 description 3
- 238000010367 cloning Methods 0.000 description 3
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
- 230000005782 double-strand break Effects 0.000 description 3
- 239000002532 enzyme inhibitor Substances 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 235000011846 forastero Nutrition 0.000 description 3
- 244000237494 forastero Species 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 238000002523 gelfiltration Methods 0.000 description 3
- 210000005265 lung cell Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 210000002307 prostate Anatomy 0.000 description 3
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 102000003915 DNA Topoisomerases Human genes 0.000 description 2
- 108090000323 DNA Topoisomerases Proteins 0.000 description 2
- 230000005778 DNA damage Effects 0.000 description 2
- 231100000277 DNA damage Toxicity 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 2
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 235000001046 cacaotero Nutrition 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002784 cytotoxicity assay Methods 0.000 description 2
- 231100000263 cytotoxicity test Toxicity 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- CTSPAMFJBXKSOY-UHFFFAOYSA-N ellipticine Chemical compound N1=CC=C2C(C)=C(NC=3C4=CC=CC=3)C4=C(C)C2=C1 CTSPAMFJBXKSOY-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 229930182497 flavan-3-ol Natural products 0.000 description 2
- 150000002206 flavan-3-ols Chemical class 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 2
- CGFVUVWMYIHGHS-UHFFFAOYSA-N saintopin Chemical compound C1=C(O)C=C2C=C(C(=O)C=3C(=C(O)C=C(C=3)O)C3=O)C3=C(O)C2=C1O CGFVUVWMYIHGHS-UHFFFAOYSA-N 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- CXQWRCVTCMQVQX-LSDHHAIUSA-N (+)-taxifolin Chemical compound C1([C@@H]2[C@H](C(C3=C(O)C=C(O)C=C3O2)=O)O)=CC=C(O)C(O)=C1 CXQWRCVTCMQVQX-LSDHHAIUSA-N 0.000 description 1
- 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 description 1
- JPFCOVZKLAXXOE-XBNSMERZSA-N (3r)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2r,3r,4r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-4-yl]-3,4-dihydro-2h-chromene-3,5,7-triol Chemical compound C1=C(O)C(OC)=C(O)C=C1C1[C@H](O)CC(C(O)=CC(O)=C2[C@H]3C4=C(O)C=C(O)C=C4O[C@@H]([C@@H]3O)C=3C=CC(O)=CC=3)=C2O1 JPFCOVZKLAXXOE-XBNSMERZSA-N 0.000 description 1
- YJGVMLPVUAXIQN-LGWHJFRWSA-N (5s,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-LGWHJFRWSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- GHCZTIFQWKKGSB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O GHCZTIFQWKKGSB-UHFFFAOYSA-N 0.000 description 1
- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 1
- BTQAFTBKHVLPEV-UHFFFAOYSA-N 3h-naphtho[2,3-e]indazole Chemical class C1=CC=CC2=CC3=C4C=NNC4=CC=C3C=C21 BTQAFTBKHVLPEV-UHFFFAOYSA-N 0.000 description 1
- CFBVWCHTNQHZLT-UHFFFAOYSA-N 4-methoxy-5-[3-(2-methoxy-4-nitro-5-sulfophenyl)-5-(phenylcarbamoyl)tetrazol-3-ium-2-yl]-2-nitrobenzenesulfonate Chemical compound COC1=CC([N+]([O-])=O)=C(S([O-])(=O)=O)C=C1N1[N+](C=2C(=CC(=C(C=2)S(O)(=O)=O)[N+]([O-])=O)OC)=NC(C(=O)NC=2C=CC=CC=2)=N1 CFBVWCHTNQHZLT-UHFFFAOYSA-N 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 241000222718 Crithidia fasciculata Species 0.000 description 1
- 108020005124 DNA Adducts Proteins 0.000 description 1
- 102000011724 DNA Repair Enzymes Human genes 0.000 description 1
- 108010076525 DNA Repair Enzymes Proteins 0.000 description 1
- 108010078339 DNA alkyltransferase Proteins 0.000 description 1
- 230000007018 DNA scission Effects 0.000 description 1
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 description 1
- 229920002079 Ellagic acid Polymers 0.000 description 1
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 description 1
- OEIJRRGCTVHYTH-UHFFFAOYSA-N Favan-3-ol Chemical compound OC1CC2=CC=CC=C2OC1C1=CC=CC=C1 OEIJRRGCTVHYTH-UHFFFAOYSA-N 0.000 description 1
- CITFYDYEWQIEPX-UHFFFAOYSA-N Flavanol Natural products O1C2=CC(OCC=C(C)C)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C=C1 CITFYDYEWQIEPX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 1
- ZIXGXMMUKPLXBB-UHFFFAOYSA-N Guatambuinine Natural products N1C2=CC=CC=C2C2=C1C(C)=C1C=CN=C(C)C1=C2 ZIXGXMMUKPLXBB-UHFFFAOYSA-N 0.000 description 1
- 241001556407 Herrania Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102100034343 Integrase Human genes 0.000 description 1
- 231100000002 MTT assay Toxicity 0.000 description 1
- 238000000134 MTT assay Methods 0.000 description 1
- 101710141452 Major surface glycoprotein G Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010029098 Neoplasm skin Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 229920001991 Proanthocyanidin Polymers 0.000 description 1
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 1
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 1
- SUYXJDLXGFPMCQ-INIZCTEOSA-N SJ000287331 Natural products CC1=c2cnccc2=C(C)C2=Nc3ccccc3[C@H]12 SUYXJDLXGFPMCQ-INIZCTEOSA-N 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 239000008049 TAE buffer Substances 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- HGEVZDLYZYVYHD-UHFFFAOYSA-N acetic acid;2-amino-2-(hydroxymethyl)propane-1,3-diol;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid Chemical compound CC(O)=O.OCC(N)(CO)CO.OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O HGEVZDLYZYVYHD-UHFFFAOYSA-N 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- RGHILYZRVFRRNK-UHFFFAOYSA-N anthracene-1,2-dione Chemical class C1=CC=C2C=C(C(C(=O)C=C3)=O)C3=CC2=C1 RGHILYZRVFRRNK-UHFFFAOYSA-N 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 239000002592 antimutagenic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229960001561 bleomycin Drugs 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
- NCMHKCKGHRPLCM-UHFFFAOYSA-N caesium(1+) Chemical compound [Cs+] NCMHKCKGHRPLCM-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000112 colonic effect Effects 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 230000005757 colony formation Effects 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 239000003398 denaturant Substances 0.000 description 1
- COKHRCLLFPZOEI-UHFFFAOYSA-N dercitin Natural products CN1C=CC2=C3C=CC=CC3=NC3=C2C1=C1SC=NC1=C3CCN(C)C COKHRCLLFPZOEI-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- XCGZWJIXHMSSQC-UHFFFAOYSA-N dihydroquercetin Natural products OC1=CC2OC(=C(O)C(=O)C2C(O)=C1)c1ccc(O)c(O)c1 XCGZWJIXHMSSQC-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- 230000012361 double-strand break repair Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229960002852 ellagic acid Drugs 0.000 description 1
- 235000004132 ellagic acid Nutrition 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 229940030275 epigallocatechin gallate Drugs 0.000 description 1
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960005542 ethidium bromide Drugs 0.000 description 1
- ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004387 flavanoid group Chemical group 0.000 description 1
- 235000011987 flavanols Nutrition 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000002196 fr. b Anatomy 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- -1 gallates Chemical class 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 235000009569 green tea Nutrition 0.000 description 1
- 230000008821 health effect Effects 0.000 description 1
- 235000006486 human diet Nutrition 0.000 description 1
- 229920001461 hydrolysable tannin Polymers 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000138 intercalating agent Substances 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 210000004216 mammary stem cell Anatomy 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 description 1
- 230000036457 multidrug resistance Effects 0.000 description 1
- UPBAOYRENQEPJO-UHFFFAOYSA-N n-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide Chemical compound CN1C=C(NC=O)C=C1C(=O)NC1=CN(C)C(C(=O)NC2=CN(C)C(C(=O)NCCC(N)=N)=C2)=C1 UPBAOYRENQEPJO-UHFFFAOYSA-N 0.000 description 1
- 229930195472 nobotanin Natural products 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 229960000988 nystatin Drugs 0.000 description 1
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229920000429 procyanidin dimer Polymers 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 210000005267 prostate cell Anatomy 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012087 reference standard solution Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000012898 sample dilution Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229940016590 sarkosyl Drugs 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 108010042747 stallimycin Proteins 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- 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)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Mycology (AREA)
- Botany (AREA)
- Polymers & Plastics (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Alternative & Traditional Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/317,226 US5554645A (en) | 1994-10-03 | 1994-10-03 | Antineoplastic cocoa extracts and methods for making and using the same |
| PCT/US1995/012963 WO1996010404A1 (en) | 1994-10-03 | 1995-10-03 | Antineoplastic cocoa extracts, methods for making, using |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO971485D0 NO971485D0 (no) | 1997-04-02 |
| NO971485L true NO971485L (no) | 1997-05-23 |
Family
ID=23232689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO971485A NO971485L (no) | 1994-10-03 | 1997-04-02 | Antineoplastiske kakao-ekstrakter, fremgangsmåter for fremstilling og anvendelse |
Country Status (26)
| Country | Link |
|---|---|
| US (13) | US5554645A (fi) |
| EP (2) | EP1759696A1 (fi) |
| JP (2) | JPH10506903A (fi) |
| CN (2) | CN1134255C (fi) |
| AP (1) | AP9700952A0 (fi) |
| AT (1) | ATE346599T1 (fi) |
| AU (1) | AU696050B2 (fi) |
| BG (1) | BG101446A (fi) |
| CA (1) | CA2201310C (fi) |
| CZ (1) | CZ99197A3 (fi) |
| DE (1) | DE69535318T2 (fi) |
| DK (1) | DK0789568T3 (fi) |
| EE (1) | EE9700074A (fi) |
| FI (1) | FI971354A (fi) |
| HU (1) | HUT77366A (fi) |
| IS (1) | IS4456A (fi) |
| LT (1) | LT4322B (fi) |
| LV (1) | LV11819B (fi) |
| MD (1) | MD970165A (fi) |
| MX (1) | MX9702415A (fi) |
| NO (1) | NO971485L (fi) |
| OA (1) | OA10604A (fi) |
| PL (1) | PL187819B1 (fi) |
| RU (1) | RU2220719C2 (fi) |
| SK (1) | SK43497A3 (fi) |
| WO (1) | WO1996010404A1 (fi) |
Families Citing this family (127)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6777005B1 (en) * | 1994-10-03 | 2004-08-17 | Mars, Incorporated | Foods containing a cocoa polyphenol additive |
| US5554645A (en) * | 1994-10-03 | 1996-09-10 | Mars, Incorporated | Antineoplastic cocoa extracts and methods for making and using the same |
| US6187315B1 (en) | 1995-03-03 | 2001-02-13 | Atajje, Inc. | Compositions and methods of treating cancer with tannin complexes |
| US6261565B1 (en) | 1996-03-13 | 2001-07-17 | Archer Daniels Midland Company | Method of preparing and using isoflavones |
| US6391310B1 (en) | 1996-03-13 | 2002-05-21 | Archer Daniels Midland Company | Method of preparing and using isoflavones for the treatment of neurological symptoms |
| PL329325A1 (en) * | 1996-04-02 | 1999-03-29 | Mars Inc | Cocoa extract compounds, method of obtaining them and their application |
| US6297273B1 (en) * | 1996-04-02 | 2001-10-02 | Mars, Inc. | Use of cocoa solids having high cocoa polyphenol content in tabletting compositions and capsule filling compositions |
| US6423743B1 (en) | 1996-04-02 | 2002-07-23 | Mars Incorporated | Cocoa extract compounds and methods for making and using the same |
| US6696485B1 (en) | 1996-04-02 | 2004-02-24 | Mars, Incorporated | Procyanidin and cyclo-oxygenase modulator compositions |
| US6469053B1 (en) * | 1996-04-02 | 2002-10-22 | Mars Incorporated | Use of procyanidins in the maintenance of vascular health and modulation of the inflammatory response |
| US6737088B1 (en) | 1996-09-06 | 2004-05-18 | Mars, Incorporated | Cocoa extracts prepared from cocoa solids having high cocoa polyphenol contents |
| US6905715B1 (en) | 1996-09-06 | 2005-06-14 | Mars, Incorporated | Cocoa solids having a high cocoa procyanidin content |
| US6558713B2 (en) * | 1996-09-06 | 2003-05-06 | Mars, Incorporated | Health of a mammal by administering a composition containing at least one cocoa polyphenol ingredient |
| US6015913A (en) * | 1996-09-06 | 2000-01-18 | Mars, Incorporated | Method for producing fat and/or solids from cocoa beans |
| US7968140B2 (en) * | 1997-09-08 | 2011-06-28 | Mars, Incorporated | Chocolates and chocolate liquor having an enhanced polyphenol content |
| US6312753B1 (en) | 1996-09-06 | 2001-11-06 | Mars, Incorporated | Cocoa components, edible products having enriched polyphenol content, methods of making same and medical uses |
| US6569446B1 (en) | 1996-09-20 | 2003-05-27 | The Howard Foundation | Solubilization of flavonols |
| AU4310697A (en) * | 1996-09-20 | 1998-04-14 | Howard Foundation, The | Method of producing polyphenol-containing compositions |
| US6238673B1 (en) | 1996-09-20 | 2001-05-29 | The Howard Foundation | Method of producing high flavonol content polyphenol compositions |
| US6066350A (en) * | 1997-02-07 | 2000-05-23 | Cargill Incorporated | Method and arrangement for processing cocoa mass |
| IL134425A0 (en) * | 1997-08-08 | 2001-04-30 | Atajje Inc | Composition and method of treating cancer with tannic acid and tannin complexes |
| US6207842B1 (en) | 1997-10-09 | 2001-03-27 | Mars Incorporated | Process for preparing procyanidin(4-6 or 4-8) oligomers and their derivatives |
| US8507018B2 (en) * | 1998-03-12 | 2013-08-13 | Mars, Incorporated | Products containing polyphenol(s) and L-arginine and methods of use thereof |
| US6805883B2 (en) | 1998-03-12 | 2004-10-19 | Mars, Incorporated | Food products containing polyphenol(s) and L-arginine to stimulate nitric oxide |
| EP1894566A1 (en) * | 1998-03-12 | 2008-03-05 | Mars, Incorporated | Products containing polyphenol(s) and L-arginine to stimulate nitric oxide production |
| ATE405169T1 (de) * | 1998-06-18 | 2008-09-15 | Meiji Seika Kaisha | Kakaopulver reich an polyphenolen, verfahren zur herstellung desselben sowie dieses enthaltender modifizierter kakao |
| US7011856B2 (en) * | 1998-08-05 | 2006-03-14 | Amino Up Chemical Co., Ltd. | Composition for the treatment of symptoms and conditions associated with aging |
| US6576275B1 (en) | 1999-02-02 | 2003-06-10 | Archer-Daniels-Midland Company | Process for extracting polyphenolic antioxidants from purine-containing plants |
| US6190716B1 (en) * | 1999-02-17 | 2001-02-20 | Scott O. Galbreath, Jr. | Method for preparing a grape derived product |
| US6156912A (en) * | 1999-04-09 | 2000-12-05 | Mars, Incorporated | 88, 66, and 68 catechin and epicatechin dimers and methods for their preparation |
| US7015338B1 (en) | 1999-04-15 | 2006-03-21 | Mars Incorporated | Synthetic methods for preparing procyanidin oligomers |
| WO2000064883A1 (fr) * | 1999-04-23 | 2000-11-02 | Kyowa Hakko Kogyo Co., Ltd. | Methodes de purification d'oligomeres de proanthocyanidine |
| KR100319251B1 (ko) * | 1999-06-30 | 2002-01-05 | 한수길 | 충치 억제 효능을 지닌 카카오 콩껍질 분획물의 제조방법 |
| KR100509119B1 (ko) * | 1999-07-16 | 2005-08-18 | 주식회사 엘지생활건강 | 프로시아니딘 올리고머를 유효성분으로 하는 약제 |
| AU2289601A (en) * | 1999-12-21 | 2001-07-03 | Mars, Incorporated | The use of procyanidins in the modulation of cytokine gene expression and protein secretion |
| JP5354833B2 (ja) * | 2000-03-10 | 2013-11-27 | 株式会社ヤクルト本社 | α−アミラーゼ活性阻害剤 |
| US6524630B2 (en) | 2000-03-22 | 2003-02-25 | Mars, Incorporated | Use of cocoa procyanidins combined with acelylsalicyclic acid as an anti-platelet therapy |
| IL152175A (en) | 2000-04-14 | 2005-08-31 | Mars Inc | Compositions and methods for improving vascular health |
| KR100353886B1 (ko) * | 2000-04-26 | 2002-09-27 | 롯데제과주식회사 | 항산화 활성을 갖는 카카오 콩껍질 발효물의 제조방법 |
| FR2808192A1 (fr) * | 2000-04-28 | 2001-11-02 | Oreal | Epichatechine comme inhibiteur de no-synthase et utilisations |
| US6627232B1 (en) * | 2000-06-09 | 2003-09-30 | Mars Incorporated | Method for extracting cocoa procyanidins |
| FR2810242B1 (fr) * | 2000-06-16 | 2003-01-17 | Nuxe Lab | Composition cosmetique et/ou dermatologique a base d'extraits de cacao |
| FR2812873B1 (fr) * | 2000-08-11 | 2003-08-01 | Barry Callebaut France | Procede de production de polyphenols a partir de feves de cacao |
| US6476241B1 (en) * | 2000-09-05 | 2002-11-05 | Mars Incorporated | Synthesis of 4α-arylepicatechins |
| AU3976402A (en) * | 2000-11-03 | 2002-06-03 | Proteotech Inc | Methods of isolating amyloid-inhibiting compounds and use of compounds isolated from uncaria tomentosa and related plants |
| US7048941B2 (en) | 2001-03-30 | 2006-05-23 | New World Enterprizes, Inc. | Chocolate composition as delivery system for nutrients and medications |
| DE60234057D1 (de) | 2001-07-25 | 2009-11-26 | Raptor Pharmaceutical Inc | Zusammensetzungen und verfahren zur modulation des transports durch die blut-hirn-schranke |
| KR100460103B1 (ko) * | 2001-10-18 | 2004-12-04 | 롯데제과주식회사 | 카카오 콩 또는 콩껍질 분획물을 함유하는 소화기계 발암 억제제 |
| US7514107B2 (en) * | 2002-03-21 | 2009-04-07 | Mars, Incorporated | Treatment of diseases involving defective gap junctional communication |
| AU2003302017A1 (en) * | 2002-05-17 | 2004-06-15 | Board Of Regents, The University Of Texas System | Cd26-based therapies for cancers and immune disease |
| US7067679B2 (en) * | 2002-10-02 | 2006-06-27 | Mars, Inc. | Synthesis of dimeric, trimeric, tetrameric pentameric, and higher oligomeric epicatechin-derived procyanidins having 4,8-interflavan linkages and their use to inhibit cancer cell growth through cell cycle arrest |
| US20040071847A1 (en) * | 2002-10-15 | 2004-04-15 | Cargill, Inc. | Producing cocoa powders with different cocoa butter contents by liquefied gas extraction on substantially the same production line |
| US7201934B2 (en) * | 2002-10-15 | 2007-04-10 | Cargill, Incorporated | Dispersible cocoa products |
| US20040071848A1 (en) * | 2002-10-15 | 2004-04-15 | Cargill Inc. | Process for producing cocoa butter and cocoa powder by liquefied gas extraction |
| US6936644B2 (en) * | 2002-10-16 | 2005-08-30 | Cookson Electronics, Inc. | Releasable microcapsule and adhesive curing system using the same |
| US20040254357A1 (en) * | 2002-12-19 | 2004-12-16 | Zaloga Gary P. | Fatty acid phenolic conjugates |
| US20070270504A1 (en) * | 2003-06-20 | 2007-11-22 | Avalon Pharmaceuticals, Inc. | Identification of Therapeutic Agents Using Genetic Fingerprinting |
| CN1889944A (zh) * | 2003-10-10 | 2007-01-03 | 马尔斯公司 | ErbB2激酶过量表达相关疾病的治疗 |
| AU2005209317B2 (en) * | 2004-01-28 | 2011-07-07 | Mars, Incorporated | Compositions and methods of use of A-type procyanidins |
| CA2554140A1 (en) * | 2004-01-30 | 2005-08-18 | Mars, Incorporated | Methods and compositions for treating cancer |
| WO2005089262A2 (en) | 2004-03-12 | 2005-09-29 | University Of Georgia Research Foundation, Inc. | Novel peanut skin extract as a vaccine adjuvant |
| WO2005107780A2 (en) * | 2004-05-10 | 2005-11-17 | Instituto Tecnológico Y De Estudios Superiores De Monterrey (Itesm) | Cancer cell growth inhibition by black bean (phaseolus vulgarisl) extracts |
| GB2414393B (en) * | 2004-05-24 | 2008-06-11 | Natraceutical Sa | Process for producing cocoa polyphenol concentrate |
| WO2006060803A2 (en) * | 2004-12-03 | 2006-06-08 | Polnox Corporation | One pot process for making polymeric antioxidants |
| EP1841779A2 (fr) * | 2005-01-28 | 2007-10-10 | Barry Callebaut AG | Utilisation de polyphenols du cacao pour le traitement de l'hyperplasie de la prostate, extrait de cacao, specifique et applications |
| EP2392258B1 (en) | 2005-04-28 | 2014-10-08 | Proteus Digital Health, Inc. | Pharma-informatics system |
| DE602005011939D1 (de) | 2005-05-31 | 2009-02-05 | Kraft Foods R & D Inc | Verfahren zur Herstellung von Polyphenol angereicherten Zusammensetzungen aus Kakaoschale |
| WO2007002854A2 (en) | 2005-06-29 | 2007-01-04 | Mars, Incorporated | Inducing peripheral blood vessel vasodilation |
| US20070004796A1 (en) * | 2005-06-29 | 2007-01-04 | Romanczyk Leo Jr | Processes for the preparation of protected-(+)-catechin and (-)-epicatechin monomers, for coupling the protected monomers with an activated, protected epicatechin monomer, and for the preparation of epicatechin-(4B,8)-epicatechin or -catechin dimers and their digallates |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| US7678363B2 (en) | 2005-08-26 | 2010-03-16 | Braincells Inc | Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| AU2006331531B2 (en) * | 2005-12-23 | 2013-01-31 | Mars, Incorporated | Skin protection and improvement |
| CA2637236A1 (en) * | 2006-01-17 | 2007-07-26 | Barry Callebaut Ag | Use of cacao polyphenols in beer production |
| JP2009527487A (ja) * | 2006-02-16 | 2009-07-30 | ザ ハーシー カンパニー | ココア製品及び心血管状態を無糖ココアで処置する方法 |
| ES2280141B1 (es) * | 2006-02-27 | 2008-10-01 | Natraceutical, S.A. | "proceso para la obtencion de polvo de cacao rico en polifenoles y bajo contenido en materia grasa y polvo de cacao obtenido". |
| EP1991212A1 (en) * | 2006-03-08 | 2008-11-19 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| US20100216734A1 (en) * | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| MX2008014320A (es) | 2006-05-09 | 2009-03-25 | Braincells Inc | Neurogenesis mediada por el receptor de 5-hidroxitriptamina. |
| US20100009983A1 (en) * | 2006-05-09 | 2010-01-14 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| WO2007138118A1 (es) * | 2006-05-25 | 2007-12-06 | Natraceutical, S.A. | Proceso de obtención de extractos de cacao con elevado contenido de polifenoles |
| WO2007146306A2 (en) | 2006-06-15 | 2007-12-21 | Mars, Incorporated | Methods and compositions for improving cognitive function |
| EP2438915A1 (en) * | 2006-07-21 | 2012-04-11 | Mars Incorporated | Improvement of arginase levels/activity |
| JP2010502722A (ja) * | 2006-09-08 | 2010-01-28 | ブレインセルス，インコーポレイティド | ４−アシルアミノピリジン誘導体を含む組み合わせ |
| AU2007299920A1 (en) * | 2006-09-19 | 2008-03-27 | Braincells, Inc. | PPAR Mediated Modulation of Neurogenesis |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| CN100428933C (zh) * | 2006-10-19 | 2008-10-29 | 华中农业大学 | 莲原花青素用于制备防治老年痴呆药物的用途 |
| EP1913821A1 (en) * | 2006-10-20 | 2008-04-23 | Kraft Foods R & D, Inc. Zweigniederlassung München | Polyphenol-rich extract from plant material |
| US8372456B2 (en) | 2006-11-17 | 2013-02-12 | Barry Callebaut Ag | Method for producing a soluble cocoa product from cocoa powder |
| US8609174B2 (en) | 2006-11-17 | 2013-12-17 | Barry Callebaut Ag | Method for producing a soluble cocoa product from cocoa powder |
| US8795627B2 (en) | 2007-03-21 | 2014-08-05 | Raptor Pharmaceuticals Inc. | Treatment of liver disorders by administration of RAP conjugates |
| GB0719545D0 (en) | 2007-10-08 | 2007-11-14 | Barry Callebaut Ag | Novel use of cocoa extract |
| GB0719542D0 (en) | 2007-10-08 | 2007-11-14 | Barry Callebaut Ag | Use of cocoa extract |
| GB0719544D0 (en) | 2007-10-08 | 2007-11-14 | Barry Callebaut Ag | Cocoa extract and use thereof |
| US9114114B2 (en) | 2007-06-21 | 2015-08-25 | Mars, Inc. | Edible products having a high cocoa polyphenol content and improved flavor and the milled cocoa extracts used therein |
| GB0719543D0 (en) | 2007-10-08 | 2007-11-14 | Barry Callebaut Ag | Cocoa extract and novel use thereof |
| GB0724716D0 (en) | 2007-12-19 | 2008-01-30 | Barry Callebaut Ag | Process |
| GB0801119D0 (en) | 2008-01-22 | 2008-02-27 | Barry Callebaut Ag | Composition |
| JP5448852B2 (ja) * | 2008-02-07 | 2014-03-19 | 株式会社明治 | ポリフェノール高含有組成物の製造方法および製造装置 |
| US20090263518A1 (en) | 2008-04-17 | 2009-10-22 | Barry Callebaut Ag | Composition and Uses Thereof |
| AU2009201515B2 (en) * | 2008-05-14 | 2011-05-19 | Unilever Plc | Frozen confectionery products |
| PT2206438E (pt) * | 2008-12-29 | 2012-05-10 | Unilever Nv | Produtos de confeitaria gelados e bebidas compreendendo teobromina e cafeína |
| AU2010216512B2 (en) | 2009-02-20 | 2016-06-30 | 2-Bbb Medicines B.V. | Glutathione-based drug delivery system |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| BRPI0925040A2 (pt) | 2009-04-03 | 2015-07-21 | Dianaplantsciences Inc | Produção e extração de procianidinas a partir da cultura celular de plantas |
| WO2010129819A2 (en) | 2009-05-06 | 2010-11-11 | Laboratory Skin Care, Inc. | Dermal delivery compositions comprising active agent-calcium phosphate particle complexes and methods of using the same |
| AU2010280932B2 (en) * | 2009-08-07 | 2013-03-07 | Unilever Plc | Process for producing cocoa husk extract |
| WO2011040969A1 (en) * | 2009-09-30 | 2011-04-07 | Massachusetts Institute Of Technology | Compositions and methods for the treatment of atherosclerosis and other related diseases |
| JP5544863B2 (ja) | 2009-12-17 | 2014-07-09 | 富士通株式会社 | 受信装置、受信方法及び受信プログラム |
| CN102984953A (zh) | 2010-03-05 | 2013-03-20 | 马斯公司 | 具有可可提取物的可口的饮料及组合物 |
| US20110218241A1 (en) * | 2010-03-06 | 2011-09-08 | Cacao Bio-Technologies, Llc | Antiviral epicatechins, epicatechin oligomers, or thiolated epicatechins from theobroma cacao for treatment of genital warts |
| CA2798911C (en) | 2010-05-19 | 2018-07-03 | Unilever Plc | Theobromine for increasing hdl-cholesterol |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| JP2013538590A (ja) | 2010-10-04 | 2013-10-17 | ダイアナプラントサイエンシズ エス．アー．エス． | 植物の細胞培養物由来のプロシアニジンの生産及び抽出 |
| US9682112B2 (en) | 2013-08-05 | 2017-06-20 | Akay Flavours & Aromatics PVT. LTD | Ultrasound-assisted continuous extraction for complete fragmentation of cocoa beans into fractions |
| US10294423B2 (en) | 2013-11-22 | 2019-05-21 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same |
| WO2016020854A1 (en) * | 2014-08-08 | 2016-02-11 | Rottapharm Biotech S.R.L. | Purified cocoa beans extracts, production and use thereof for the treatment of central and peripheric human diseases |
| WO2016020853A1 (en) * | 2014-08-08 | 2016-02-11 | Rottapharm Biotech S.R.L. | Purified cocoa beans and grape seeds extracts, production and use thereof for the treatment of central and peripheric human diseases |
| WO2016046375A1 (en) * | 2014-09-25 | 2016-03-31 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Theobroma cacao extract for use in the treatment or prevention of receptor tyrosine kinases related disorders |
| CN106109512A (zh) * | 2016-06-27 | 2016-11-16 | 郭迎庆 | 一种可可多酚咀嚼片的制备方法 |
| WO2018160879A2 (en) | 2017-03-01 | 2018-09-07 | Polnox Corporation | Macromolecular corrosion (mcin) inhibitors: structures, methods of making and using the same |
| US11173187B2 (en) * | 2018-11-13 | 2021-11-16 | Immortazyme Company Ltd. | Concentrated oil-based polyphenol composition and a method of producing the oil-based polyphenol composition |
| CN113358592B (zh) * | 2020-03-04 | 2023-06-06 | 福建医科大学 | 基于海藻酸钠-铂纳米粒子氧化酶活性的原花青素检测方法 |
| CN112870238B (zh) * | 2021-02-04 | 2022-05-27 | 徐州奇诺医疗科技有限公司 | 可可提取物在制备抵抗衰老及抑制肿瘤的药物中的应用 |
| CN114306320A (zh) * | 2021-02-04 | 2022-04-12 | 汤臣倍健股份有限公司 | 一种下调衰老相关分泌表型的抗衰老植物多酚类药物及其应用 |
Family Cites Families (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB14624A (fi) | 1900-01-01 | |||
| US1750795A (en) | 1926-01-04 | 1930-03-18 | Defren George | Process of treating cacao beans |
| US1855026A (en) | 1927-08-15 | 1932-04-19 | Monsanto Chemical Works | Treatment of by-products of the cocoa and chocolate industries |
| GB345250A (en) | 1929-10-07 | 1931-03-09 | Monsanto Chemical Works | Improvements in and relating to the recovery and purification of alkaloids from cocoa products |
| GB341000A (en) | 1929-10-07 | 1931-01-07 | Monsanto Chemical Works | Process for recovering valuable products from cocoa by-products |
| US1925326A (en) | 1929-11-13 | 1933-09-05 | Battle Creek Food Company | Theobromine extracting process |
| GB492714A (en) | 1937-03-23 | 1938-09-23 | British Ass Of Res For Cocoa C | Preservation of organic materials, particularly oils and fats and bodies containing the same |
| US2176031A (en) | 1939-04-01 | 1939-10-10 | Musher Foundation Inc | Retarding rancidity in glyceride oils |
| US2380158A (en) | 1942-10-21 | 1945-07-10 | Inredeco Inc | Method of preparing a cocoa extract |
| GB562123A (en) | 1942-10-21 | 1944-06-19 | Inredeco Inc | Improvements in method of preparing a cocoa extract |
| US2515794A (en) * | 1946-05-15 | 1950-07-18 | Moorehead Mfg Co Inc | Method of preparing cocoa extracts |
| US2512663A (en) * | 1947-04-25 | 1950-06-27 | Choco Essence Inc | Chocolate essence or extract |
| GB751121A (en) | 1953-07-10 | 1956-06-27 | Gen Foods Corp | Improvements in or relating to chocolate flavoring material |
| US2835585A (en) * | 1953-07-10 | 1958-05-20 | Gen Foods Corp | Chocolate product and process therefor |
| US2823124A (en) * | 1955-02-14 | 1958-02-11 | Limpert Bros Inc | Process for preparation of chocolate extract or chocolate syrup from cocoa |
| US2954293A (en) * | 1958-02-28 | 1960-09-27 | Gen Foods Corp | Preparation of chocolate flavoring |
| US2957769A (en) * | 1958-04-03 | 1960-10-25 | Gen Foods Corp | Chocolate product and process therefor |
| US2965490A (en) * | 1959-04-02 | 1960-12-20 | Gen Foods Corp | Flavor product and process |
| US3615659A (en) * | 1968-08-28 | 1971-10-26 | Wisconsin Research Associates | Preparing a chocolate-flavored beverage |
| DE2055030C3 (de) | 1970-11-09 | 1978-06-22 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | Verfahren zur Herstellung eines Kakaoextrakts |
| US4113886A (en) * | 1977-09-28 | 1978-09-12 | General Foods Corporation | Membrane decaffeination |
| US4156030A (en) | 1977-12-29 | 1979-05-22 | Societe D'assistance Technique Pour Produits Nestle S.A. | Cocoa shell extract |
| DE2910539C2 (de) * | 1978-11-10 | 1986-07-24 | Iwatani Sangyo K.K., Osaka | Verfahren zum Herstellen von Kakaopulver |
| US4237288A (en) | 1979-05-17 | 1980-12-02 | Societe D'assistance Technique Pour Produits Nestle S.A. | Decaffeination of fatty materials |
| US4861607A (en) * | 1981-03-20 | 1989-08-29 | Nestec S. A. | Removal of xanthine stimulants from cocoa |
| GB2095091B (en) | 1981-03-20 | 1984-08-22 | Nestle Sa | Removal of xanthine stimulants from cocoa |
| US4390698A (en) | 1981-05-21 | 1983-06-28 | Societe D'assistance Technique Pour Produits Nestle S.A. | Detheobromination of cocoa |
| US4407834A (en) | 1981-05-21 | 1983-10-04 | Societe D'assistance Technique Pour Produits Nestle S.A. | Recovery of xanthine stimulants from aqueous media |
| JPS57206391A (en) | 1981-06-12 | 1982-12-17 | Morinaga & Co Ltd | Preparation of flavonoid natural pigment by enzymic treatment |
| DE3125144C1 (de) | 1981-06-26 | 1983-02-24 | Lindt & Sprüngli AG, 8802 Kilchberg | Verfahren zur Gewinnung von Nahrungsfasern fuer die Verbesserung der verdauungsfoerdernden Eigenschaften von Nahrungs- und Genussmitteln |
| CH641935A5 (fr) | 1981-07-22 | 1984-03-30 | Nestle Sa | Procede d'elimination des composes stimulants du cacao. |
| JPS59169452A (ja) | 1983-03-15 | 1984-09-25 | Meiji Seika Kaisha Ltd | カカオ豆の処理方法 |
| US4532147A (en) * | 1983-08-03 | 1985-07-30 | General Foods Corporation | Cacao product and process therefor |
| JPS6116982A (ja) * | 1984-07-03 | 1986-01-24 | Kikkoman Corp | 抗酸化剤 |
| NL8403748A (nl) * | 1984-12-10 | 1986-07-01 | Zaan Cacaofab Bv | Cacaopoeder. |
| US4698360B1 (en) | 1985-04-09 | 1997-11-04 | D Investigations Pharmacologiq | Plant extract with a proanthocyanidins content as therapeutic agent having radical scavenger effect and use thereof |
| US4755391A (en) | 1986-01-22 | 1988-07-05 | Hershey Foods Corporation | Removal of methylxanthines from cacao materials |
| JP2527788B2 (ja) | 1988-05-31 | 1996-08-28 | 株式会社ロッテ | 口腔用組成物 |
| IT1219732B (it) | 1988-06-28 | 1990-05-24 | Tecnofarmaci Spa | Frazioni oligomeriche procianidoliche,loro procedimento di preparazione e composizioni farmaceutiche che le contengono |
| US4970090A (en) * | 1988-09-26 | 1990-11-13 | Mccormick & Company, Inc. | Enhanced cocoa extract flavorings |
| KR910004494B1 (ko) | 1988-10-21 | 1991-07-05 | 롯데제과 주식회사 | 카카오콩 껍질(cacao bean husk)의 수용성 추출물을 배합한 충치예방 츄잉껌의 제조방법 |
| KR900007862A (ko) * | 1988-11-10 | 1990-06-02 | 정보영 | 카카오 콩 껍질(cacao bean husk)추출물로부터 세파덱스 g-50(sephadex g-50)에의해 분획된 f-1, f-2의 글루칸 합성 저해물질 |
| FR2643073B1 (fr) | 1989-02-15 | 1991-08-16 | Expansion Rech Phytochimie | Procede de preparation d'extraits polyphenoliques de type flavane-3-ol purifies et extraits obtenus |
| US4956429A (en) * | 1989-03-01 | 1990-09-11 | Penick Corporation | Method of making a coca leaf flavor extract |
| DE3908649A1 (de) | 1989-03-16 | 1990-09-20 | Jacobs Suchard Ag | Verfahren zur herstellung eines loeslichen kakaoerzeugnisses |
| DE3912819A1 (de) | 1989-04-19 | 1990-11-08 | Jacobs Suchard Ag | Verfahren zur herstellung von kakao-extrakt |
| US5211944A (en) * | 1990-10-12 | 1993-05-18 | Shaman Pharmaceuticals, Inc. | Proanthocyanidin polymers having antiviral activity and methods of obtaining same |
| JP2857646B2 (ja) | 1990-11-26 | 1999-02-17 | キッコーマン株式会社 | 抗変異原性剤 |
| US5391568A (en) | 1992-07-10 | 1995-02-21 | American Health Foundation | Inhibition of lung tumorigenesis by administration of a polyphenol |
| JP3509891B2 (ja) * | 1993-02-24 | 2004-03-22 | サントリー株式会社 | フラボノイド重合物およびこれを有効成分とするグルコシルトランスフェラーゼ阻害剤 |
| DE4325532A1 (de) * | 1993-07-29 | 1995-02-02 | Schwabe Willmar | Präparate aus Crataegus-Arten, Arzneimittel und ihre Verwendung zur Verhinderung des plötzlichen Herztodes sowie von reperfusionsbedingten cardiovaskulären Schädigungen |
| JP3095605B2 (ja) | 1994-02-04 | 2000-10-10 | 明治製菓株式会社 | 抗酸化物質を含有する健康飲食品および抗酸化物質の製造法 |
| JP3063818B2 (ja) | 1994-04-01 | 2000-07-12 | 明治製菓株式会社 | 胃潰瘍予防飲食品 |
| JPH0822848A (ja) | 1994-07-08 | 1996-01-23 | Tokai Rika Co Ltd | コネクタ装置 |
| US5554645A (en) * | 1994-10-03 | 1996-09-10 | Mars, Incorporated | Antineoplastic cocoa extracts and methods for making and using the same |
| US6777005B1 (en) * | 1994-10-03 | 2004-08-17 | Mars, Incorporated | Foods containing a cocoa polyphenol additive |
| JP3450080B2 (ja) | 1995-02-01 | 2003-09-22 | 有限会社野々川商事 | プロシアニジンを配合した健康食品および医薬品 |
| JP3594152B2 (ja) | 1996-02-08 | 2004-11-24 | 明治製菓株式会社 | ストレスに対する適応形成を促進させる飲食品 |
| JPH09224606A (ja) | 1996-02-19 | 1997-09-02 | Meiji Seika Kaisha Ltd | 発ガン予防物質を含有する健康飲食品 |
| JPH09234018A (ja) | 1996-03-01 | 1997-09-09 | Meiji Seika Kaisha Ltd | 糖尿病合併症予防作用を有する飲食品 |
| US6261565B1 (en) | 1996-03-13 | 2001-07-17 | Archer Daniels Midland Company | Method of preparing and using isoflavones |
| US6297273B1 (en) * | 1996-04-02 | 2001-10-02 | Mars, Inc. | Use of cocoa solids having high cocoa polyphenol content in tabletting compositions and capsule filling compositions |
| US6312753B1 (en) * | 1996-09-06 | 2001-11-06 | Mars, Incorporated | Cocoa components, edible products having enriched polyphenol content, methods of making same and medical uses |
| US5912363A (en) | 1997-08-29 | 1999-06-15 | Interhealth Nutraceuticals | Method for extraction of proanthocyanidins from plant material |
| EP1026164A1 (en) | 1999-02-02 | 2000-08-09 | ADM Cocoa B.V. | Process for extracting polyphenolic antioxidants from purine-containing plants |
| KR100319251B1 (ko) * | 1999-06-30 | 2002-01-05 | 한수길 | 충치 억제 효능을 지닌 카카오 콩껍질 분획물의 제조방법 |
| US6524630B2 (en) * | 2000-03-22 | 2003-02-25 | Mars, Incorporated | Use of cocoa procyanidins combined with acelylsalicyclic acid as an anti-platelet therapy |
| IT1317035B1 (it) | 2000-05-30 | 2003-05-26 | Sigma Tau Healthscience Spa | Integratore ad attivita' antiossidante comprendente unaalcanoilcarnitina ed una associazione di polifenoli estratti dal |
| US6627232B1 (en) * | 2000-06-09 | 2003-09-30 | Mars Incorporated | Method for extracting cocoa procyanidins |
-
1994
- 1994-10-03 US US08/317,226 patent/US5554645A/en not_active Expired - Lifetime
-
1995
- 1995-10-03 MD MD97-0165A patent/MD970165A/ro unknown
- 1995-10-03 AP APAP/P/1997/000952A patent/AP9700952A0/en unknown
- 1995-10-03 HU HU9702279A patent/HUT77366A/hu unknown
- 1995-10-03 SK SK434-97A patent/SK43497A3/sk unknown
- 1995-10-03 PL PL95319756A patent/PL187819B1/pl unknown
- 1995-10-03 CN CNB951965956A patent/CN1134255C/zh not_active Expired - Lifetime
- 1995-10-03 AU AU38916/95A patent/AU696050B2/en not_active Ceased
- 1995-10-03 DK DK95938189T patent/DK0789568T3/da active
- 1995-10-03 DE DE69535318T patent/DE69535318T2/de not_active Expired - Lifetime
- 1995-10-03 EP EP06024499A patent/EP1759696A1/en not_active Withdrawn
- 1995-10-03 CZ CZ97991A patent/CZ99197A3/cs unknown
- 1995-10-03 WO PCT/US1995/012963 patent/WO1996010404A1/en active IP Right Grant
- 1995-10-03 AT AT95938189T patent/ATE346599T1/de active
- 1995-10-03 RU RU97106832/15A patent/RU2220719C2/ru active
- 1995-10-03 MX MX9702415A patent/MX9702415A/es not_active Application Discontinuation
- 1995-10-03 JP JP8512152A patent/JPH10506903A/ja active Pending
- 1995-10-03 EE EE9700074A patent/EE9700074A/xx unknown
- 1995-10-03 EP EP95938189A patent/EP0789568B1/en not_active Revoked
- 1995-10-03 CA CA002201310A patent/CA2201310C/en not_active Expired - Lifetime
- 1995-10-03 CN CNB2003101015256A patent/CN100357287C/zh not_active Expired - Lifetime
-
1996
- 1996-07-26 US US08/687,885 patent/US5712305A/en not_active Expired - Lifetime
-
1997
- 1997-04-02 NO NO971485A patent/NO971485L/no unknown
- 1997-04-02 FI FI971354A patent/FI971354A/fi not_active Application Discontinuation
- 1997-04-02 IS IS4456A patent/IS4456A/is unknown
- 1997-04-03 OA OA60986A patent/OA10604A/en unknown
- 1997-04-14 US US08/834,637 patent/US5877206A/en not_active Expired - Lifetime
- 1997-04-14 US US08/839,446 patent/US5891905A/en not_active Expired - Lifetime
- 1997-04-22 US US08/837,803 patent/US6479539B1/en not_active Expired - Lifetime
- 1997-04-25 BG BG101446A patent/BG101446A/xx active Pending
- 1997-04-29 LT LT97-077A patent/LT4322B/lt not_active IP Right Cessation
- 1997-05-02 LV LVP-97-85A patent/LV11819B/xx unknown
-
1998
- 1998-10-15 US US09/172,873 patent/US6225338B1/en not_active Expired - Lifetime
- 1998-11-23 US US09/198,551 patent/US6156791A/en not_active Expired - Fee Related
-
2001
- 2001-01-24 US US09/768,473 patent/US6562863B2/en not_active Expired - Lifetime
- 2001-10-11 US US09/975,242 patent/US6517841B2/en not_active Expired - Lifetime
-
2003
- 2003-01-15 US US10/342,772 patent/US6790966B2/en not_active Expired - Fee Related
-
2004
- 2004-03-01 US US10/790,268 patent/US20040175448A1/en not_active Abandoned
-
2007
- 2007-05-08 US US11/745,698 patent/US7820713B2/en not_active Expired - Fee Related
- 2007-10-29 US US11/926,919 patent/US20080269320A1/en not_active Abandoned
-
2009
- 2009-09-03 JP JP2009203541A patent/JP2009286796A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO971485L (no) | Antineoplastiske kakao-ekstrakter, fremgangsmåter for fremstilling og anvendelse | |
| CA2250792C (en) | Cocoa extract compounds and methods for making and using the same | |
| US20040220392A1 (en) | Compositions for, and methods of, treating atherosclerosis | |
| WO1997036597A1 (en) | Cocoa extract compounds and methods for making and using the same | |
| US6777005B1 (en) | Foods containing a cocoa polyphenol additive | |
| Rica et al. | Romanczyk, Jr. et al. | |
| AU2005203665A1 (en) | Cocoa extract compounds and methods for making and using the same | |
| MXPA00007491A (en) | Remote platform independent dynamic multimedia engine | |
| AU8364901A (en) | Cocoa extract compounds and methods for making and using the same |