NZ782575A - Method for preparing an extract containing gallic acid, aqueous concentrate containing gallic acid, and foodstuff and food supplement containing the aqueous concentrate - Google Patents
Method for preparing an extract containing gallic acid, aqueous concentrate containing gallic acid, and foodstuff and food supplement containing the aqueous concentrateInfo
- Publication number
- NZ782575A NZ782575A NZ782575A NZ78257521A NZ782575A NZ 782575 A NZ782575 A NZ 782575A NZ 782575 A NZ782575 A NZ 782575A NZ 78257521 A NZ78257521 A NZ 78257521A NZ 782575 A NZ782575 A NZ 782575A
- Authority
- NZ
- New Zealand
- Prior art keywords
- range
- gallic acid
- plants
- weight
- aqueous
- Prior art date
Links
- LNTHITQWFMADLM-UHFFFAOYSA-N Gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 title claims abstract description 103
- 229940074391 Gallic acid Drugs 0.000 title claims abstract description 51
- 235000004515 gallic acid Nutrition 0.000 title claims abstract description 51
- 239000012141 concentrate Substances 0.000 title claims abstract description 35
- 239000000284 extract Substances 0.000 title claims abstract description 31
- 235000015872 dietary supplement Nutrition 0.000 title abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 239000000470 constituent Substances 0.000 claims abstract description 27
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 20
- 238000000605 extraction Methods 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 108010038851 tannase Proteins 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 235000013824 polyphenols Nutrition 0.000 claims abstract description 11
- 150000008442 polyphenolic compounds Chemical class 0.000 claims abstract description 10
- 239000006286 aqueous extract Substances 0.000 claims abstract description 7
- 229920001864 tannin Polymers 0.000 claims abstract description 6
- 239000001648 tannin Substances 0.000 claims abstract description 6
- 235000018553 tannin Nutrition 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000001263 FEMA 3042 Substances 0.000 claims description 4
- 229940033123 Tannic Acid Drugs 0.000 claims description 4
- LRBQNJMCXXYXIU-NRMVVENXSA-N Tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 229920002258 tannic acid Polymers 0.000 claims description 4
- 235000015523 tannic acid Nutrition 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000005325 percolation Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 26
- 235000013399 edible fruits Nutrition 0.000 description 8
- 244000269722 Thea sinensis Species 0.000 description 7
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
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- 235000013681 dietary sucrose Nutrition 0.000 description 6
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- 235000006226 Areca catechu Nutrition 0.000 description 5
- 241000219492 Quercus Species 0.000 description 5
- 241001092459 Rubus Species 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- 235000013361 beverage Nutrition 0.000 description 5
- GLEVLJDDWXEYCO-UHFFFAOYSA-N 6-Hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 description 4
- 240000000073 Achillea millefolium Species 0.000 description 4
- 235000007754 Achillea millefolium Nutrition 0.000 description 4
- 241000906543 Actaea racemosa Species 0.000 description 4
- 235000001274 Anacardium occidentale Nutrition 0.000 description 4
- 240000001407 Anacardium occidentale Species 0.000 description 4
- 235000012871 Arctostaphylos uva ursi Nutrition 0.000 description 4
- 240000004377 Arctostaphylos uva-ursi Species 0.000 description 4
- 240000008886 Ceratonia siliqua Species 0.000 description 4
- 235000007542 Cichorium intybus Nutrition 0.000 description 4
- 240000008051 Cichorium intybus Species 0.000 description 4
- 235000016551 Potentilla erecta Nutrition 0.000 description 4
- 240000000103 Potentilla erecta Species 0.000 description 4
- 235000016976 Quercus macrolepis Nutrition 0.000 description 4
- 235000006468 Thea sinensis Nutrition 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 230000003078 antioxidant Effects 0.000 description 4
- 235000005301 cimicifuga racemosa Nutrition 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 235000013616 tea Nutrition 0.000 description 4
- 240000000239 Camellia sinensis Species 0.000 description 3
- 241001070941 Castanea Species 0.000 description 3
- 235000014036 Castanea Nutrition 0.000 description 3
- HHEAADYXPMHMCT-UHFFFAOYSA-N DPPH Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 3
- 235000014826 Mangifera indica Nutrition 0.000 description 3
- 240000007228 Mangifera indica Species 0.000 description 3
- 235000009569 green tea Nutrition 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 241001093951 Ailanthus altissima Species 0.000 description 2
- 235000011468 Albizia julibrissin Nutrition 0.000 description 2
- 235000015363 Amaranthus cruentus Nutrition 0.000 description 2
- 244000303769 Amaranthus cruentus Species 0.000 description 2
- 235000003092 Artemisia dracunculus Nutrition 0.000 description 2
- 240000001851 Artemisia dracunculus Species 0.000 description 2
- 240000006914 Aspalathus linearis Species 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
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- 240000000019 Diospyros kaki Species 0.000 description 2
- 235000015070 Elaeocarpus Nutrition 0.000 description 2
- 241001112084 Elaeocarpus Species 0.000 description 2
- 244000119298 Emblica officinalis Species 0.000 description 2
- 235000015489 Emblica officinalis Nutrition 0.000 description 2
- 241000220223 Fragaria Species 0.000 description 2
- 235000017367 Guainella Nutrition 0.000 description 2
- 241000220225 Malus Species 0.000 description 2
- 240000005852 Mimosa quadrivalvis Species 0.000 description 2
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- 241000218657 Picea Species 0.000 description 2
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- 241000208225 Rhus Species 0.000 description 2
- 235000013178 Rhus coriaria Nutrition 0.000 description 2
- 240000004029 Rhus coriaria Species 0.000 description 2
- 235000016554 Rubus chamaemorus Nutrition 0.000 description 2
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- 240000003497 Rubus idaeus Species 0.000 description 2
- 241000124033 Salix Species 0.000 description 2
- 240000005332 Sorbus domestica Species 0.000 description 2
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 2
- 240000005147 Syzygium aromaticum Species 0.000 description 2
- 229940087164 TORMENTIL Drugs 0.000 description 2
- 241001106462 Ulmus Species 0.000 description 2
- 235000017357 Uva orsina Nutrition 0.000 description 2
- 235000011676 Vaccinium erythrocarpum Nutrition 0.000 description 2
- 235000010726 Vigna sinensis Nutrition 0.000 description 2
- 240000000728 Vigna unguiculata Species 0.000 description 2
- 241000219094 Vitaceae Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000020279 black tea Nutrition 0.000 description 2
- 235000021029 blackberry Nutrition 0.000 description 2
- 235000020226 cashew Nutrition 0.000 description 2
- 150000001765 catechin Chemical class 0.000 description 2
- 229930016253 catechin Natural products 0.000 description 2
- 235000005487 catechin Nutrition 0.000 description 2
- 235000002318 elaeocarpus Nutrition 0.000 description 2
- 235000002532 grape seed extract Nutrition 0.000 description 2
- 235000021021 grapes Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000018838 origanum vulgare Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000020334 white tea Nutrition 0.000 description 2
- RNKMOGIPOMVCHO-SJMVAQJGSA-N 1,3,6-Trigalloyl glucose Chemical compound C([C@@H]1[C@H]([C@@H]([C@@H](O)[C@H](OC(=O)C=2C=C(O)C(O)=C(O)C=2)O1)OC(=O)C=1C=C(O)C(O)=C(O)C=1)O)OC(=O)C1=CC(O)=C(O)C(O)=C1 RNKMOGIPOMVCHO-SJMVAQJGSA-N 0.000 description 1
- 240000006523 Abies balsamea Species 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 244000235603 Acacia catechu Species 0.000 description 1
- 235000006020 Acacia catechu Nutrition 0.000 description 1
- 241000355014 Acacieae Species 0.000 description 1
- 235000011446 Amygdalus persica Nutrition 0.000 description 1
- 241001081440 Annonaceae Species 0.000 description 1
- 241001444063 Aronia Species 0.000 description 1
- 235000003826 Artemisia Nutrition 0.000 description 1
- 240000003325 Artemisia Species 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 235000003884 Aspalathus contaminatus Nutrition 0.000 description 1
- 235000012984 Aspalathus linearis Nutrition 0.000 description 1
- 241001247458 Aspidosperma quebracho-blanco Species 0.000 description 1
- 241000871469 Astronium balansae Species 0.000 description 1
- 241000048176 Astronium urundeuva Species 0.000 description 1
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- 241000219429 Betula Species 0.000 description 1
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- 235000009133 Caesalpinia coriaria Nutrition 0.000 description 1
- 235000005082 Caesalpinia paraguariensis Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 241000723377 Coffea Species 0.000 description 1
- 235000007460 Coffea arabica Nutrition 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 235000010206 Corchorus olitorius Nutrition 0.000 description 1
- 240000008487 Corchorus olitorius Species 0.000 description 1
- 235000009807 Cydonia Nutrition 0.000 description 1
- 241001507921 Cydonia Species 0.000 description 1
- 235000017788 Cydonia oblonga Nutrition 0.000 description 1
- 240000000590 Cydonia oblonga Species 0.000 description 1
- 231100000277 DNA damage Toxicity 0.000 description 1
- 230000028937 DNA protection Effects 0.000 description 1
- 235000003550 Dracunculus Nutrition 0.000 description 1
- 241000316827 Dracunculus <angiosperm> Species 0.000 description 1
- 235000007297 Gaultheria procumbens Nutrition 0.000 description 1
- 240000001238 Gaultheria procumbens Species 0.000 description 1
- 241000208680 Hamamelis mollis Species 0.000 description 1
- 241000208681 Hamamelis virginiana Species 0.000 description 1
- 241001409295 Handroanthus impetiginosus Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000023813 Isia Species 0.000 description 1
- 241001002197 Juglans mollis Species 0.000 description 1
- 235000013628 Lantana involucrata Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241001618206 Libidibia coriaria Species 0.000 description 1
- 240000000982 Malva neglecta Species 0.000 description 1
- 235000000060 Malva neglecta Nutrition 0.000 description 1
- 241001093152 Mangifera Species 0.000 description 1
- 208000001145 Metabolic Syndrome Diseases 0.000 description 1
- 241000234295 Musa Species 0.000 description 1
- 235000010677 Origanum vulgare Nutrition 0.000 description 1
- 240000005158 Phaseolus vulgaris Species 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- 235000010659 Phoenix dactylifera Nutrition 0.000 description 1
- 240000001732 Phoenix dactylifera Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
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- 235000014360 Punica granatum Nutrition 0.000 description 1
- 240000006764 Punica granatum Species 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 240000000639 Quercus garryana Species 0.000 description 1
- 241001531309 Quercus infectoria Species 0.000 description 1
- 241000920652 Quercus lusitanica Species 0.000 description 1
- 240000008751 Quercus petraea Species 0.000 description 1
- 235000002913 Quercus petraea Nutrition 0.000 description 1
- 235000011471 Quercus robur Nutrition 0.000 description 1
- 240000009089 Quercus robur Species 0.000 description 1
- 241000284847 Quercus velutina Species 0.000 description 1
- 241000120541 Rhizophora Species 0.000 description 1
- 240000002044 Rhizophora apiculata Species 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 240000005505 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 235000017276 Salvia Nutrition 0.000 description 1
- 240000007164 Salvia officinalis Species 0.000 description 1
- 235000002912 Salvia officinalis Nutrition 0.000 description 1
- 235000003142 Sambucus nigra Nutrition 0.000 description 1
- 240000006028 Sambucus nigra Species 0.000 description 1
- 241000978911 Senegalia catechu Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 241000286862 Siliqua Species 0.000 description 1
- 235000010394 Solidago odora Nutrition 0.000 description 1
- 235000010425 Sorbus domestica Nutrition 0.000 description 1
- 240000007913 Spondias dulcis Species 0.000 description 1
- 241000001522 Terminalia chebula Species 0.000 description 1
- 241000907897 Tilia Species 0.000 description 1
- 235000004652 Tilia americana var heterophylla Nutrition 0.000 description 1
- 240000007313 Tilia cordata Species 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000010840 Tilia tomentosa Nutrition 0.000 description 1
- 235000010722 Vigna unguiculata Nutrition 0.000 description 1
- 235000011842 Xylopia aethiopica Nutrition 0.000 description 1
- 240000008612 Xylopia aethiopica Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000111 anti-oxidant Effects 0.000 description 1
- 238000002792 antioxidant assay Methods 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 235000009052 artemisia Nutrition 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 235000018185 birch Nutrition 0.000 description 1
- 235000018212 birch Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000004807 chebulic myrobalan Nutrition 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 235000001535 currant Nutrition 0.000 description 1
- 235000001537 currant Nutrition 0.000 description 1
- 229920003013 deoxyribonucleic acid Polymers 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary Effects 0.000 description 1
- 235000011869 dried fruits Nutrition 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000008995 european elder Nutrition 0.000 description 1
- 235000021022 fresh fruits Nutrition 0.000 description 1
- 229920002824 gallotannin Polymers 0.000 description 1
- 150000004676 glycans Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000009200 high fat diet Nutrition 0.000 description 1
- 229920001461 hydrolysable tannin Polymers 0.000 description 1
- 230000002218 hypoglycaemic Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 235000006677 lemon beebalm Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000021013 raspberries Nutrition 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 239000001296 salvia officinalis l. Substances 0.000 description 1
- 235000019614 sour taste Nutrition 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 230000000475 sunscreen Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Abstract
The present invention relates to a method for preparing an extract containing gallic acid, comprising performing an extraction treatment on plants or plant constituents containing tannins by means of water or an aqueous system in the presence of the enzyme tannase to obtain a product mixture containing gallic acid, and to a method for preparing an extract containing gallic acid, comprising performing an extraction treatment on plants or plant constituents containing tannins by means of a mixture containing a polar organic solvent and water to obtain a product mixture containing polyphenols, separating the plants or plant constituents from the product mixture to obtain a liquid extract, removing the polar organic solvent from the liquid extract, and treating the aqueous extract with the enzyme tannase to obtain an aqueous system containing gallic acid. In addition, the invention relates to an aqueous concentrate containing gallic acid, characterized by a dry weight in the range of 5 to 80% by weight, based on the total weight of the aqueous concentrate. Finally, the invention relates to a foodstuff or food supplement comprising the aqueous concentrate. ing gallic acid, and to a method for preparing an extract containing gallic acid, comprising performing an extraction treatment on plants or plant constituents containing tannins by means of a mixture containing a polar organic solvent and water to obtain a product mixture containing polyphenols, separating the plants or plant constituents from the product mixture to obtain a liquid extract, removing the polar organic solvent from the liquid extract, and treating the aqueous extract with the enzyme tannase to obtain an aqueous system containing gallic acid. In addition, the invention relates to an aqueous concentrate containing gallic acid, characterized by a dry weight in the range of 5 to 80% by weight, based on the total weight of the aqueous concentrate. Finally, the invention relates to a foodstuff or food supplement comprising the aqueous concentrate.
Description
Method for preparing an extract containing gallic acid, aqueous concentrate
containing gallic acid, and foodstuff and food ment containing
the aqueous concentrate
Description
This application claims priority from European patent application No. 40.3, filed 20
er 2021, and the entire contents of that application are orated herein by nce.
The present invention relates to a method for preparing an extract containing gallic acid, in
particular in high concentrations. Moreover, the invention relates to an aqueous concentrate
containing gallic acid. Furthermore, the invention relates to a foodstuff and food supplement
containing the aqueous concentrate according to the ion.
Gallic acid (3,4,5-trihydroxy benzoic acid) is the acid component of gallotannins, which are
hydrolyzable tannins. They are found, for e, in oak bark and in oak apples. Gallic
acid is used to produce antioxidants, sunscreens and dyes. Furthermore, it has been postulated
that gallic acid, due to its hypoglycemic ties, helps prevent adverse health
effects in obese people that consume foods rich in gallic acid. The consumption of gallic
acid is said to be associated with demonstrable DNA protection or reduced oxidation of
DNA bases as well as reduced inflammation parameters (see also T. Setayesh et al. “Gallic
acid, a common dietary phenolic protects against high fat diet induced DNA damage” in
European Journal of ion, vol. 58, pages 2315 to 26, 2019).
According to EP 1 942 919 B1, a composition containing a polyphenol extract from grapes,
which may comprise 400 to 1,500 ppm of gallic acid, is said to be suitable for treating metabolic
syndrome or prehypertension.
According to EP 2 095 718 B1, a tea beverage based on a tea extract, in which the weight
ratio of gallic acid to non-polymeric catechins must not exceed 0.3, is characterized by reduced
ness and a reduced sour taste.
EP 2 143 344 B1 describes a beverage ition containing 0.5 to 25.0% by weight of
non-polymeric catechins, a carbohydrate and a hydroxycarboxylic acid. In these compositions
, the gallic acid content has to be less than 0.6% by weight.
Previously, gallic acid has often been obtained by means of aqueous extraction methods.
However, these s frequently produce only low yields of gallic acid and are intensive
in terms of materials, equipment and costs.
The object of the present invention was therefore to provide a method for obtaining gallic
acid that does not have the drawbacks of the prior art and, in particular, reliably and efficiently
produces good yields of gallic acid. An alternative or additional object of the present
invention was to at least e the public with a useful choice.
Thus, a method for preparing an extract ning gallic acid was found (also called first
embodiment of the method according to the invention), comprising the steps of
a) ing, in particular comminuted and/or, in particular and, dried, plants or plant
constituents containing tannins, in particular tannic acid,
b) providing the enzyme tannase (IUB 3.1.1.20),
c) providing at least one polar organic solvent,
d) optionally comminuting or further comminuting, respectively, the plants or plant constituents
according to step a), and
e) performing an extraction treatment on the plants or plant constituents ed, in
particular comminuted, according to step a) and/or, in particular or, d), by means of
water or an aqueous system in the presence of the enzyme tannase (IUB 3.1.1.20)
to obtain a product mixture containing gallic acid.
For the, in particular comminuted and/or dried, plants or plant constituents, the following
may be used: leaves, wood, bark, fruits, seeds and/or roots, pr eferably the fruits, of legumes
, e.g. beans and peas; nuts, e.g. walnuts ns regia); grains; trees, e.g. oak
(Quercus), preferably the cupules and/or fruits (Valonea), particularly preferably from varieties
of oak growing in Asia Minor and/or in the southern s, and/or oak galls (Galla),
in particular fromQuercus infectoria, Quercus petraea or Quercus robur, spruces (Picea),
the carob tree (also ed to as St John’s bread) onia siliqua ), the Divi-Divi-tree
(Caesalpinia coriaria), the kaki tree yros kaki), the sorb tree (Sorbus domestica),
acacia (Acacieae), e.g. cutchtree (also referred to as catechu) (Senegalia catechu), willow
(Salix), lan tree, mangrove tree (Rhizophora), mango tree fera indica), in
particular bark, fruit pulp and/or kernel of the mango tree, hemlock ), the urunday
tree (Astronium balansae), birch (Betula), Elaeocarpus, in particular the outer bark thereof,
tree of heaven (Ailanthus ima), chestnut (Castanea), in particular the fruits and leaves
from chestnut, the betel nut palm (Areca catechu), the cashew tree(Anacardium occi-
dentale) and/or cho ( Aspidosperma quebracho-blanco); mimosa (Mimosa ); sumac
plants (Rhus), ally Sicilian sumac (Rhus coriaria), in particular the fruits; hops
lus); fruit, e.g. apples (Malus), pears (Pryus), strawberries (Fragaria), raspberries
(Rubus idaeus), blackberries (Rubus sect. Rubus), rries nium vitis-idaea),
s (Musa), grapes (Vitis vinifera), peaches (Prunus persica), quinces (Cydonia ob-
longa) and/or plums s domestica); coffee beans (e.g. e.g. Coffea arabica or Coffea
canephor); tea plants (Camellia sinensis) such as green tea (e.g. Japanese, Chinese
and/or Indian teas), in particular the leaves of sencha green tea, black tea, in particular the
leaves of Darjeeling, white tea, in ular the leaves of China Oolong white tea, and/or
rooibos (Aspalathus linearis); cloves (Syzygium aromaticum), preferably the buds and/or
leaves thereof, yarrow (Achillea millefolium); black cohosh (Actaea racemosa); bearberry
(Arctostaphylos uva-ursi); tarragon isia dracunculus), tormentil (Potentilla erecta);
and/or peat. Furthermore, for the, in particular comminuted and/or dried, plants or plant
constituents, the following may be used: chebulic myrobalan, mango tree (Mangifera indi-
ca), in particular the bark, fruit pulp and kernel, Elaeocarpus (Elaecoarpus ganitrus), in par-
ticular the outer bark, jute mallow (Corchorus olitorius), red amaranth (Amaranthus cru-
entus), cowpea (Vigna unguiculata), chard (Beta vulgaris var. cicla. ), Greek mountain tea
itis raseri), American witch-hazel (Hamamelis virginiana), in particular the bark, Aleppo
oak, dyer's oak (Quercus infectoria), currants (Vitis vinifera a), chicory coffee
(Cichorium intybus), carob powder (Ceratonia siliqua), green oat (Avena sativa L. ), elm
bark (Ulmus), chokeberry pomace a melanocarpa), linden bark (Tilia), elder bark
(Sambucus nigra), lapacho bark (Tabebuia impetiginosa), chicory (Cichorium intybus), amla
(Phyllanthus emblica), Chinese blackberry (Rubus suavissimus), pomegranate a
granatum L. ), sage (Salvia), oregano (Origanum vulgare), cloudberry (Rubus chamaemorus
) and date palms (Phoenix).From the yarrow (Achillea millefolium), black cohosh (Actaea
racemosa), bearberry (Arctostaphylos uva-ursi), tarragon (Artemisia culus) and
tormentil (Potentilla erecta), preferably the whole plant is used for extraction. In the case of
betel nut palm (Areca catechu) and the cashew tree (Anacardium occidentale), the seeds
are preferably used for extraction.
In a preferred ment, the method according to the invention according to the first
embodiment further comprises (step f)) separating the, in particular comminuted, plants or
plant constituents from the product mixture obtained according to step e), in particular following
step e), ably by means of a sieve.
Additionally or alternatively, the method according to the invention according to the first
embodiment may further comprise (step g)) concentrating, in particular by evaporation, the
product mixture containing gallic acid obtained according to step e) or f), in particular following
step e) or f) and/or before step h).
Moreover, the method according to the invention according to the first embodiment may
further additionally or alternatively comprise (step h)) treating the product mixture according
to step e) or f) with the at least one polar organic solvent, in particular ethanol and/or methanol
, and/or heat-treating the product mixture according to step e) or step f) or g). The
treatment with the polar organic solvent, in particular ethanol, or, in particular and, the additional
heat treatment consistently allow(s) the enzyme e to be deactivated. In ular
, this is also achieved by ng the t mixture with the at least one polar organic
t, in particular ethanol, in step h) at temperatures in the range of 40 to 80°C or
above 45 to 80°C, preferably 40 to 75°C or 48 to 75°C and particularly preferably 50 to
70°C. For r optimization of method step h), in this step, additionally or alternatively, in
particular additionally, the at least one polar organic solvent, in particular ethanol, may be
added in an amount in the range of 15 to 70% by weight, preferably in the range of 20 to
65% by weight, particularly preferably in the range of 25 to 60 and in particular in the range
of 40 to 60% by weight, in each case based on the total weight of the polar organic t
and the water or the aqueous system. Step h), in particular the treatment with a polar t
, in particular ethanol, consistently allows both the enzyme to be deactivated and phytoproteins
and/or polysaccharides to be red and precipitated.
In an expedient embodiment, steps f) and g) occur in sequence. Moreover, steps f) and h)
may be ed while omitting step g), or steps g) and h) may be combined while omitting
step f). In a particularly preferred embodiment, method step e) is followed by method
steps f), g) and h), the sequence f)/g)/h) being preferred.
In a preferred embodiment of the method according to the invention ing to the first
embodiment, the d product mixture according to step h) is filtered, for example using
a filter having a mesh size in the range of 0.10 to 1.0 µm, preferably in the range of 0.25 to
1.0 µm. In this way, a clear extract is generally obtained.
In many cases, it has also proved expedient to subsequently remove the polar organic solvent
added in step h) from the d product mixture according to step h) or from the filtered
product mixture according to step i) (step j).
The extraction ent according to step e) is preferably performed at temperatures in
the range of 20 to 45°C or 30 to 43°C, with temperatures in the range of 35 to 40°C, in particular
in the range of 36 to 38°C, being particularly preferred.
The object of the invention is further solved by a method for ing an extract containing
gallic acid (also referred to as the second ment of the method according to the invention
), comprising the steps of
1) providing, in particular comminuted and/or, in particular and, dried, plants or plant
constituents, containing s, in particular tannic acid,
2) providing the enzyme tannase (IUB 3.1.1.20),
3) providing at least one polar organic solvent, in particular ethanol,
4) optionally comminuting or further comminuting the plants or plant constituents according
to step 1),
) performing an extraction treatment on the, in particular dried and/or comminuted,
plants or plant constituents according to step 1) and/or, in particular or, 4) by means
of a mixture containing the polar organic solvent, in particular l, and water to
obtain a product mixture containing polyphenols,
6) separating the, in particular comminuted, plants or plant constituents from the product
e according to step 5) to obtain a liquid extract containing the polyphenols,
in particular by means of a sieve,
7) removing the polar organic solvent, in particular ethanol, from the liquid extract according
to step 6) to obtain an aqueous extract containing the polyphenols,
8) treating the s extract ing to step 7) with the enzyme tannase (IUB
3.1.1.20) to obtain an s system containing gallic acid.
The object of the invention is also achieved ularly well by the method according to the
second embodiment by performing the extraction treatment according to step 5) at temperatures
in the range of 50 to 70°C, in particular in the range of 55 to 65°C.
In a preferred embodiment, the second embodiment t of the method according to the
invention is also characterized in that in step 5), ethanol is added in an amount in the range
of 60 to 90% by weight, preferably in the range of 70 to 85% by weight, in each case based
on the total weight of ethanol and the water.
In the second embodiment of the method according to the invention, the treatment of the
s extract according to step 8) with the enzyme tannase is preferably carried out at
temperatures in the range of 20 to 45°C, preferably 30 to 43°C, particularly preferably 35 to
40°C, in particular in the range of 36 to 38°C.
Surprisingly, it has been shown that a particularly ent method is also achieved by the,
in ular ground, preferably comminuted, plants or plant constituents being immobilized
in step e) according to the first embodiment or step 5), respectively, according to the second
embodiment, in particular immobilized in a sieve support.
The extraction treatment according to step e) in the first embodiment or step 5) in the second
embodiment ably comprises or is a percolation process.
Particularly high yields or concentrations of gallic acid can also be achieved with the methods
according to the invention by adjusting the amount of tannase in step e) according to
the first embodiment or step 5) ing to the second embodiment in the range of 0.1 U/g
to 100.0 U/g, preferably in the range of 0.2 U/g to 50.0 U/g, based on the amount of plants
or plant constituents.
It has also proved to be particularly cal to concentrate the aqueous extract containing
gallic acid obtained according to step i) or j) according to the first embodiment or the aqueous
system containing gallic acid according to step 8) according to the second ment
, in particular by evaporation, to obtain an aqueous concentrate. This aqueous trate
is preferably a so-called spissum extract. Said aqueous trate or said spissum
extract has in particular a Brix value in the range of 1° to 100° Brix, preferably in the
range of 10° to 70° Brix and particularly preferably in the range of 20° to 50° Brix. Very particularly
preferably, concentrates having Brix values in the range of 20° to 40° Brix, in particular
in the range of 25° to 35° Brix, are aimed for or obtained in the concentrating step.
The ination of degrees Brix is familiar to a person skilled in the art. A liquid has a
Brix value of 1° when the liquid has the same density as a solution of 1 g of saccharose in
100 g of saccharose/water solution, and a Brix value of 10° when the density of the liquid is
that of a solution of 10 g of saccharose in 100 g of saccharose/water solution. Thus, a figure
indicated in degrees Brix means that the density of the measured liquid corresponds to
the density of a solution of saccharose in water that contains as many grams of saccharose
per 100 g of on as the figure in s.
The object of the invention is further solved by an s concentrate containing gallic
acid, in ular obtained according to the first embodiment, the dry-weight amount used
for said aqueous concentrate being in the range of 5 to 80% by weight, preferably in the
range of 10 to 50% by weight and particularly preferably in the range of 15 to 40% by
weight, in each case based on the total weight of the aqueous concentrate. Said aqueous
trates are particularly suitable for producing foodstuffs and food supplements, in
particular those in the form of beverages.
Dry weight within the meaning of the invention is understood to be the dry weight obtained
by removing all aqueous and non-aqueous solvents from the extracts that can be obtained
according to the methods according to the invention.
In ular, those aqueous concentrates are preferred which are obtained either according
to the method according to the invention according to the first embodiment or according
to the method according to the invention according to the second embodiment, those
aqueous concentrates being particularly preferred which can be obtained according to the
method according to the invention according to the first embodiment.
In particular, the aqueous concentrates according to the invention, in particular obtained
according to the first embodiment, have a pH in the range of 1.5 to 5.5, preferably in the
range of 1.75 to 4.5 and particularly ably in the range of 2.0 to 4.0, or are adjusted to
a pH in the range of 1.5 to 5.5, preferably in the range of 1.75 to 4.5 and particularly preferably
in the range of 2.0 to 4.0.
In preferred aqueous trates according to the invention, in particular ed according
to the first embodiment, the amount of gallic acid is at least 10 g/kg dry weight, preferably
at least 50 g/kg dry weight and particularly preferably at least 75 g/kg dry weight. Those
aqueous trates are particularly expedient in which gallic acid is present in an
amount in the range of 10 to 250 g/kg dry weight, preferably in the range of 50 to 200 g/kg
dry weight and particularly preferably in the range of 75 to 175 g/kg dry weight, in each
case based on the total weight of the aqueous concentrate.
Suitable aqueous concentrates according to the invention, in particular obtained according
to the first embodiment, preferably have a ve density [20/20] in the range of 1.001 to
1.4000, preferably in the range of 1.010 to 1.2500. The relative density [20/20] is the quotient
of the density of the tested sample (measured at 20°C) and the density of water at
°C. The measurement is taken in particular by means of a flexural oscillator according to
§ 35 LMBG 36.0 3a n Foodstuffs and Commodities Act in the version applicable on
the date of application) (determination of the relative density d 20/20 of wort and beer (flexural
oscillator method). Particularly suitable aqueous concentrates are characterized by a
total phenol content in the range of 5 to 350 g GAE/kg, preferably in the range of 50 to 300
g GAE/kg and particularly preferably in the range of 75 to 250 g GAE/kg and in particular in
the range of 125 to 200 g GAE/kg, in each case based on the dry weight of the extract.
The total phenol t can be determined ing to the method according to DIN ISO
14502-1:2007-11 mination of substances characteristic of green and black tea - Part
1: t of total polyphenols in tea - Colorimetric method using Folin-Ciocalteu t).
Furthermore, the object of the invention is solved by a foodstuff, for e a beverage,
and by a food supplement, containing or formed from the aqueous concentrate according
to the ion.
The t invention is accompanied by the surprising finding that, when the extraction
methods according to the invention are used according to the first embodiment and according
to the second embodiment variant, but in particular according to the first embodiment,
high yields of gallic acid can be ed efficiently and inexpensively from a wide variety of
plant materials or components thereof, meaning that aqueous concentrates having a very
high gallic acid concentration can be ed. It was surprisingly found that the aqueous
concentrates according to the invention in particular have a Trolox-equivalent antioxidant
capacity in the range of 500 to 6,000 µmol/g, preferably in the range of 1,000 to 5,000
µmol/g and particularly preferably 2,000 to 4,000 µmol/g, in each case based on the dry
weight of the extract. The Trolox-equivalent antioxidant capacity can be expediently determined
by the DPPH (2,2-diphenylpicrylhydrazyl) assay. This determination method is
familiar to a person skilled in the art and is described, for example, by O. Sharma and T. N.
Bhat in “DPPH antioxidant assay revisited”, Food Chemistry 113(4):1202-1205, April 2009,
and by A. Karioti et al. in “Composition and idant ty of the essential oils of Xylo-
pia aethiopica (Dun) A. Rich. (Annonaceae) leaves, stem bark, root bark, and fresh and
dried fruits, growing in Ghana”, J. Agric. Food Chem. 29;52(26):8094-8, December 2004.
For example, in this method, 10 mg of the stable radical DPPH can be dissolved in 100 ml
methanol, mixed with the particular sample extract or the standard (Trolox), and then incubated
for 30 min at room temperature, and the absorbance is subsequently determined
photometrically at 517 nm. The antioxidant ial of the samples can then be determined
from a linear relationship between absorbance and the standard concentrations. The
results can be calculated as Trolox equivalents or as micromoles of Trolox/g of the sample
and in relation to the dry weight. With the described method, an absorbance difference is
determined, from which the antioxidant capacity of the tested substance can be determined
by comparison with the reduction in absorbance caused by Trolox at different concentrations.
The aqueous concentrates according to the invention can be directly used for producing
foodstuffs, in particular beverages, and food supplements.
The es of the invention disclosed in the above description and in the claims may be
ial either individually or in any desired ation for carrying out the various embodiments
of the invention.
The term “comprising” as used in this specification and claims means “consisting at least in
part of”. When interpreting statements in this specification and claims which include the
term ising”, other features besides the features prefaced by this term in each statement
can also be present. Related terms such as “comprise” and “comprises” are to be
interpreted in a similar .
In this ication where reference has been made to patent specifications, other external
nts, or other sources of information, this is generally for the purpose of providing a
context for discussing the es of the invention. Unless specifically stated otherwise,
reference to such external documents, or such sources of ation, is not to be construed
as an admission that such documents, or such sources of information, in any iction
, are prior art, or form part of the common general knowledge in the art.
Claims (18)
1. A method for preparing an extract containing gallic acid, comprising the steps of a) providing, in particular dried , in ular and, comminuted, plants or plant constituents, containing tannins, in particular tannic acid, b providing the enzyme tannase, c) providing at least one polar organic solvent, d) optionally comminuting or further comminuting, respectively, the plants or plant constituents according to step a), e) ming an extraction treatment on the plants or plant constituents obtained , in particular comminuted, according to step a) and/or d) by means of water or an aqueous system in the presence of the enzyme tannase to obtain a product mixture containing gallic acid.
2. The method according to Claim 1, further comprising f) separating the, in particular comminuted, plants or plant constituents from the product mixture obtained ing to step e), in particular following step e), and/or, in particular and, g) concentrating, in particular by evaporation, the product mixture obtained according to step e) or f), containing gallic acid, in particular ing step e) or f) and/or before step h), , in particular and, h) treating the product mixture according to step e) or f) with the at least one polar organic solvent, in particular ethanol and/or ol, and/or, in particular and, heat-treating the product mixture according to step e) or f) or g), and i) optionally filtering the treated product e according to step h) and/or, in particular and, j) optionally removing the polar organic solvent added in step h) from the treated product mixture according to step h) or the filtered t mixture ing to step i).
3. The method according to Claim 1 or 2, wherein the extraction treatment according to step e) is carried out at temperatures in the range of 20 to 45°C.
4. The method ing to any one of the preceding claims, wherein the treatment of the product mixture with the at least one polar organic solvent, in particular ethanol, according to step h) is carried out at temperatures in the range of 40 to 75°C.
5. The method according to any one of the preceding claims, wherein in step h), the at least one polar organic solvent, in particular ethanol, is added in an amount in the range of 15 to 70% by weight, preferably in the range of 20 to 65% by weight and particularly ably in the range of 40 to 60% by weight, in each case based on the total weight of the polar organic solvent and the water or the aqueous system.
6. A method for preparing an extract containing gallic acid, comprising the steps of 1) providing, in particular, comminuted and/or, in particular and, dried plants or plant constituents containing tannins, in particular tannic acid, 2) providing the enzyme tannase, 3) providing at least one polar organic solvent, in particular ethanol, 4) ally uting or further comminuting the plants or plant constituents according to step 1), 5) ming an extraction treatment on the, in particular comminuted, plants or plant constituents according to step 1) and/or 4) with a e containing the polar or- ganic solvent, in particular ethanol, and water to obtain a product mixture, containing polyphenols 6) separating the, in particular comminuted, plants or plant constituents from the product mixture according to step 5) to obtain a liquid extract containing the polyphenols 7) removing the polar organic solvent, in particular ethanol, from the liquid extract according to step 6) to obtain an s extract containing the polyphenols, 8) treating the aqueous extract according to step 7) with the enzyme tannase to obtain an aqueous system, ning gallic acid.
7. The method according to any one of the preceding claims, wherein the plants or plant constituents, in particular ground, preferably uted, are immobilized in step e) or step 5), respectively, in particular immobilized in a sieve support.
8. The method according to any one of the preceding claims, wherein the extraction treatment according to step e) or step 5), respectively, comprises a percolation process.
9. The method according to any one of the preceding claims, n the amount of tannase in step e) or step 5), tively, is in the range of 0.1 U/g to 100.0 U/g, preferably in the range of 0.2 U/g to 50.0 U/g, based on the amount of plants or plant constituents.
10. The method according to any one of the preceding claims, further comprising concentrating , in particular by evaporation, the aqueous extract containing gallic acid obtained according to step i) or j), in particular according to step j), or the aqueous system containing gallic acid according to step 8), tively, to obtain an s trate, in particular a spissum extract.
11. The method according to Claim 10, wherein the s concentrate has a Brix value in the range of 1° to 100° Brix, ably in the range of 10° to 70° Brix and particularly preferably in the range of 20° to 50° Brix.
12. The method according to any one of Claims 6 to 11, wherein the extraction treatment according to step 5) is carried out at temperatures in the range of 50 to 70°C, in particular in the range of 55 to 65°C.
13. The method according to any one of the preceding claims, wherein the tion treatment according to step e) or the treatment of the aqueous extract according to step 8) with the enzyme e is d out at temperatures in the range of 35 to 40°C.
14 The method according to any one of Claims 6 to 13, wherein in step 5), ethanol is added in an amount in the range of 60 to 90% by weight, preferably in the range of 70 to 85% by weight, in each case based on the total weight of ethanol and the water.
15. An aqueous concentrate, containing gallic acid, in particular obtained or obtainable according to a method according to any one of the preceding claims, characterized by a dry weight in the range of 5 to 80% by weight, preferably in the range of 10 to 50% by weight and particularly preferably in the range of 15 to 40% by weight, in each case based on the total weight of the aqueous concentrate.
16. The aqueous concentrate according to Claim 15, characterized by a pH in the range of 1.5 to 5.5, preferably in the range of 1.75 to 4.5 and particularly preferably in the range of 2.0 to 4.0.
17. The aqueous concentrate according to Claim 15 or 16, characterized by an amount of gallic acid of at least 10 g/kg dry weight, preferably at least 50 g/kg dry weight and par- ticularly preferably at least 75 g/kg dry weight, and/or an amount of gallic acid in the range of 10 to 250 g/kg dry weight, preferably in the range of 50 to 200 g/kg dry weight and particularly preferably in the range of 75 to 175 g/kg dry weight, in each case based on the total weight of the aqueous concentrate.
18. An aqueous concentrate according to any one of Claims 15 to 17, characterized by a ve density [
Applications Claiming Priority (1)
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