WO2006111163A1 - Plant extraction process - Google Patents
Plant extraction process Download PDFInfo
- Publication number
- WO2006111163A1 WO2006111163A1 PCT/DK2006/000081 DK2006000081W WO2006111163A1 WO 2006111163 A1 WO2006111163 A1 WO 2006111163A1 DK 2006000081 W DK2006000081 W DK 2006000081W WO 2006111163 A1 WO2006111163 A1 WO 2006111163A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- plant material
- cutinase
- compound
- enzyme
- plant
- Prior art date
Links
- 238000000605 extraction Methods 0.000 title claims description 24
- 108090000790 Enzymes Proteins 0.000 claims abstract description 48
- 102000004190 Enzymes Human genes 0.000 claims abstract description 48
- 239000000463 material Substances 0.000 claims abstract description 36
- 230000002366 lipolytic effect Effects 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 239000000419 plant extract Substances 0.000 claims abstract description 3
- 108010005400 cutinase Proteins 0.000 claims description 57
- 241000196324 Embryophyta Species 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 108010059820 Polygalacturonase Proteins 0.000 claims description 23
- 108010093305 exopolygalacturonase Proteins 0.000 claims description 22
- 235000010208 anthocyanin Nutrition 0.000 claims description 19
- 239000004410 anthocyanin Substances 0.000 claims description 19
- 229930002877 anthocyanin Natural products 0.000 claims description 19
- 150000004636 anthocyanins Chemical class 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 10
- 235000013399 edible fruits Nutrition 0.000 claims description 9
- 238000011534 incubation Methods 0.000 claims description 8
- 241000896533 Gliocladium Species 0.000 claims description 7
- 240000001890 Ribes hudsonianum Species 0.000 claims description 7
- 235000016954 Ribes hudsonianum Nutrition 0.000 claims description 7
- 235000001466 Ribes nigrum Nutrition 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 241001480714 Humicola insolens Species 0.000 claims description 6
- 244000078534 Vaccinium myrtillus Species 0.000 claims description 6
- 241000082085 Verticillium <Phyllachorales> Species 0.000 claims description 6
- 235000013311 vegetables Nutrition 0.000 claims description 6
- 235000021016 apples Nutrition 0.000 claims description 5
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 claims description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 claims description 4
- 240000003259 Brassica oleracea var. botrytis Species 0.000 claims description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 4
- 235000002566 Capsicum Nutrition 0.000 claims description 4
- 235000002767 Daucus carota Nutrition 0.000 claims description 4
- 244000000626 Daucus carota Species 0.000 claims description 4
- 239000006002 Pepper Substances 0.000 claims description 4
- 235000016761 Piper aduncum Nutrition 0.000 claims description 4
- 240000003889 Piper guineense Species 0.000 claims description 4
- 235000017804 Piper guineense Nutrition 0.000 claims description 4
- 235000008184 Piper nigrum Nutrition 0.000 claims description 4
- 235000017537 Vaccinium myrtillus Nutrition 0.000 claims description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 4
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims description 3
- 241000219094 Vitaceae Species 0.000 claims description 3
- 235000021028 berry Nutrition 0.000 claims description 3
- 239000012634 fragment Substances 0.000 claims description 3
- 235000021021 grapes Nutrition 0.000 claims description 3
- 235000009434 Actinidia chinensis Nutrition 0.000 claims description 2
- 244000298697 Actinidia deliciosa Species 0.000 claims description 2
- 235000009436 Actinidia deliciosa Nutrition 0.000 claims description 2
- 244000291564 Allium cepa Species 0.000 claims description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims description 2
- 240000002234 Allium sativum Species 0.000 claims description 2
- 244000144730 Amygdalus persica Species 0.000 claims description 2
- 240000007087 Apium graveolens Species 0.000 claims description 2
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 claims description 2
- 235000010591 Appio Nutrition 0.000 claims description 2
- 241000167854 Bourreria succulenta Species 0.000 claims description 2
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 claims description 2
- 240000002791 Brassica napus Species 0.000 claims description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 2
- 240000007124 Brassica oleracea Species 0.000 claims description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims description 2
- 235000017647 Brassica oleracea var italica Nutrition 0.000 claims description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims description 2
- 244000178937 Brassica oleracea var. capitata Species 0.000 claims description 2
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 claims description 2
- 244000188595 Brassica sinapistrum Species 0.000 claims description 2
- 235000004936 Bromus mango Nutrition 0.000 claims description 2
- 240000004160 Capsicum annuum Species 0.000 claims description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 2
- 235000005979 Citrus limon Nutrition 0.000 claims description 2
- 244000131522 Citrus pyriformis Species 0.000 claims description 2
- 235000012778 Empetrum nigrum Nutrition 0.000 claims description 2
- 244000169938 Empetrum nigrum Species 0.000 claims description 2
- 235000016623 Fragaria vesca Nutrition 0.000 claims description 2
- 240000009088 Fragaria x ananassa Species 0.000 claims description 2
- 235000011363 Fragaria x ananassa Nutrition 0.000 claims description 2
- 244000194101 Ginkgo biloba Species 0.000 claims description 2
- 241000223198 Humicola Species 0.000 claims description 2
- 235000003228 Lactuca sativa Nutrition 0.000 claims description 2
- 240000008415 Lactuca sativa Species 0.000 claims description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 2
- 235000014826 Mangifera indica Nutrition 0.000 claims description 2
- 240000007228 Mangifera indica Species 0.000 claims description 2
- 240000004371 Panax ginseng Species 0.000 claims description 2
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims description 2
- 235000003140 Panax quinquefolius Nutrition 0.000 claims description 2
- IOUVKUPGCMBWBT-DARKYYSBSA-N Phloridzin Natural products O[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-DARKYYSBSA-N 0.000 claims description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 claims description 2
- 241000220324 Pyrus Species 0.000 claims description 2
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 claims description 2
- 235000002357 Ribes grossularia Nutrition 0.000 claims description 2
- 244000171263 Ribes grossularia Species 0.000 claims description 2
- 244000281247 Ribes rubrum Species 0.000 claims description 2
- 235000016911 Ribes sativum Nutrition 0.000 claims description 2
- 235000002355 Ribes spicatum Nutrition 0.000 claims description 2
- 235000016897 Ribes triste Nutrition 0.000 claims description 2
- 235000017848 Rubus fruticosus Nutrition 0.000 claims description 2
- 240000007651 Rubus glaucus Species 0.000 claims description 2
- 235000011034 Rubus glaucus Nutrition 0.000 claims description 2
- 235000009122 Rubus idaeus Nutrition 0.000 claims description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 2
- 244000151637 Sambucus canadensis Species 0.000 claims description 2
- 235000018735 Sambucus canadensis Nutrition 0.000 claims description 2
- 241000533293 Sesbania emerus Species 0.000 claims description 2
- 240000003768 Solanum lycopersicum Species 0.000 claims description 2
- 235000009337 Spinacia oleracea Nutrition 0.000 claims description 2
- 244000300264 Spinacia oleracea Species 0.000 claims description 2
- 235000009184 Spondias indica Nutrition 0.000 claims description 2
- 244000269722 Thea sinensis Species 0.000 claims description 2
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 2
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims description 2
- 235000003095 Vaccinium corymbosum Nutrition 0.000 claims description 2
- 240000001717 Vaccinium macrocarpon Species 0.000 claims description 2
- 235000012545 Vaccinium macrocarpon Nutrition 0.000 claims description 2
- 235000002118 Vaccinium oxycoccus Nutrition 0.000 claims description 2
- 235000017606 Vaccinium vitis idaea Nutrition 0.000 claims description 2
- 244000077923 Vaccinium vitis idaea Species 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 235000006708 antioxidants Nutrition 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 235000021029 blackberry Nutrition 0.000 claims description 2
- 235000007123 blue elder Nutrition 0.000 claims description 2
- 235000021014 blueberries Nutrition 0.000 claims description 2
- 235000019693 cherries Nutrition 0.000 claims description 2
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 2
- 235000020971 citrus fruits Nutrition 0.000 claims description 2
- 235000004634 cranberry Nutrition 0.000 claims description 2
- 235000021038 drupes Nutrition 0.000 claims description 2
- 235000007124 elderberry Nutrition 0.000 claims description 2
- 235000008995 european elder Nutrition 0.000 claims description 2
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 claims description 2
- 235000011957 flavonols Nutrition 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 229940074391 gallic acid Drugs 0.000 claims description 2
- 235000004515 gallic acid Nutrition 0.000 claims description 2
- 235000004611 garlic Nutrition 0.000 claims description 2
- 235000008434 ginseng Nutrition 0.000 claims description 2
- 239000004571 lime Substances 0.000 claims description 2
- 235000021017 pears Nutrition 0.000 claims description 2
- IOUVKUPGCMBWBT-UHFFFAOYSA-N phloridzosid Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-UHFFFAOYSA-N 0.000 claims description 2
- IOUVKUPGCMBWBT-QNDFHXLGSA-N phlorizin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-QNDFHXLGSA-N 0.000 claims description 2
- 235000019139 phlorizin Nutrition 0.000 claims description 2
- 235000021283 resveratrol Nutrition 0.000 claims description 2
- 229940016667 resveratrol Drugs 0.000 claims description 2
- 241000894007 species Species 0.000 claims description 2
- 235000013616 tea Nutrition 0.000 claims description 2
- 241001284615 Frangula californica Species 0.000 claims 1
- 244000070406 Malus silvestris Species 0.000 claims 1
- 235000004433 Simmondsia californica Nutrition 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims 1
- 229930002875 chlorophyll Natural products 0.000 claims 1
- 235000019804 chlorophyll Nutrition 0.000 claims 1
- 229920002770 condensed tannin Polymers 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 229930182497 flavan-3-ol Natural products 0.000 claims 1
- 150000002206 flavan-3-ols Chemical class 0.000 claims 1
- 125000004387 flavanoid group Chemical group 0.000 claims 1
- 150000002216 flavonol derivatives Chemical class 0.000 claims 1
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 230000002879 macerating effect Effects 0.000 claims 1
- 125000003020 stilbenoid group Chemical group 0.000 claims 1
- 235000018553 tannin Nutrition 0.000 claims 1
- 229920001864 tannin Polymers 0.000 claims 1
- 239000001648 tannin Substances 0.000 claims 1
- 239000002699 waste material Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 229940088598 enzyme Drugs 0.000 description 39
- 235000013824 polyphenols Nutrition 0.000 description 27
- 241000220225 Malus Species 0.000 description 23
- 150000008442 polyphenolic compounds Chemical class 0.000 description 22
- -1 polyphenols Chemical class 0.000 description 14
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- 229930182470 glycoside Natural products 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 5
- 102000004882 Lipase Human genes 0.000 description 5
- 239000004367 Lipase Substances 0.000 description 5
- 241001533598 Septoria Species 0.000 description 5
- 241000223258 Thermomyces lanuginosus Species 0.000 description 5
- 235000019421 lipase Nutrition 0.000 description 5
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 4
- 108010064785 Phospholipases Proteins 0.000 description 4
- 102000015439 Phospholipases Human genes 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 239000008351 acetate buffer Substances 0.000 description 4
- 229920001184 polypeptide Polymers 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 240000005384 Rhizopus oryzae Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- YVLPJIGOMTXXLP-UHFFFAOYSA-N all-trans-Phytoen Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CC=CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C YVLPJIGOMTXXLP-UHFFFAOYSA-N 0.000 description 3
- ATCICVFRSJQYDV-UHFFFAOYSA-N all-trans-neurosporene Natural products CC(C)=CCCC(C)=CCCC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C ATCICVFRSJQYDV-UHFFFAOYSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 235000021466 carotenoid Nutrition 0.000 description 3
- 125000001895 carotenoid group Chemical group 0.000 description 3
- 235000015110 jellies Nutrition 0.000 description 3
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 3
- 235000021395 porridge Nutrition 0.000 description 3
- 235000014347 soups Nutrition 0.000 description 3
- YVLPJIGOMTXXLP-UUKUAVTLSA-N 15,15'-cis-Phytoene Natural products C(=C\C=C/C=C(\CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)/C)(\CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)/C YVLPJIGOMTXXLP-UUKUAVTLSA-N 0.000 description 2
- YVLPJIGOMTXXLP-BAHRDPFUSA-N 15Z-phytoene Natural products CC(=CCCC(=CCCC(=CCCC(=CC=C/C=C(C)/CCC=C(/C)CCC=C(/C)CCC=C(C)C)C)C)C)C YVLPJIGOMTXXLP-BAHRDPFUSA-N 0.000 description 2
- LBKFGYZQBSGRHY-UHFFFAOYSA-N 3-hydroxy-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1O LBKFGYZQBSGRHY-UHFFFAOYSA-N 0.000 description 2
- 240000006439 Aspergillus oryzae Species 0.000 description 2
- 241000228232 Aspergillus tubingensis Species 0.000 description 2
- 241000223221 Fusarium oxysporum Species 0.000 description 2
- 241000427940 Fusarium solani Species 0.000 description 2
- JEVVKJMRZMXFBT-XWDZUXABSA-N Lycophyll Natural products OC/C(=C/CC/C(=C\C=C\C(=C/C=C/C(=C\C=C\C=C(/C=C/C=C(\C=C\C=C(/CC/C=C(/CO)\C)\C)/C)\C)/C)\C)/C)/C JEVVKJMRZMXFBT-XWDZUXABSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- ATCICVFRSJQYDV-DDRHJXQASA-N Neurosporene Natural products C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)/C)\C)(\C=C\C=C(/CC/C=C(\C)/C)\C)/C ATCICVFRSJQYDV-DDRHJXQASA-N 0.000 description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 description 2
- 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 2
- 241000235527 Rhizopus Species 0.000 description 2
- 241001207471 Septoria sp. Species 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
- 241000221841 Verticillium sp. (in: Hypocreales) Species 0.000 description 2
- OXPQJSVMVIIPNK-UHFFFAOYSA-N Zeacarotene Natural products CC=C(/C)CCC(=CCCC(=CC=CC(=CC=CC=C(/C)C=CC=C(/C)C=CC1=C(C)CCCC1(C)C)C)C)C OXPQJSVMVIIPNK-UHFFFAOYSA-N 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 235000005473 carotenes Nutrition 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- VEVZSMAEJFVWIL-UHFFFAOYSA-O cyanidin cation Chemical compound [O+]=1C2=CC(O)=CC(O)=C2C=C(O)C=1C1=CC=C(O)C(O)=C1 VEVZSMAEJFVWIL-UHFFFAOYSA-O 0.000 description 2
- 235000013365 dairy product Nutrition 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 235000008696 isoflavones Nutrition 0.000 description 2
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 2
- 235000012661 lycopene Nutrition 0.000 description 2
- 239000001751 lycopene Substances 0.000 description 2
- 229960004999 lycopene Drugs 0.000 description 2
- 235000008665 neurosporene Nutrition 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 235000011765 phytoene Nutrition 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- PCMORTLOPMLEFB-ONEGZZNKSA-N sinapic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-ONEGZZNKSA-N 0.000 description 2
- HUJXHFRXWWGYQH-UHFFFAOYSA-O sinapine Chemical compound COC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O HUJXHFRXWWGYQH-UHFFFAOYSA-O 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 2
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 2
- 238000011514 vinification Methods 0.000 description 2
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 2
- IGABZIVJSNQMPZ-DWQNOKSTSA-N (6r)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,19e)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,19,23-decaenyl]-1,5,5-trimethylcyclohexene Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=CCCC1(C)C IGABZIVJSNQMPZ-DWQNOKSTSA-N 0.000 description 1
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- VUDQSRFCCHQIIU-UHFFFAOYSA-N 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one Chemical compound CCCCCC(=O)C1=C(O)C(Cl)=C(OC)C(Cl)=C1O VUDQSRFCCHQIIU-UHFFFAOYSA-N 0.000 description 1
- KZTYPOGXRFTJBN-MMLDQJOMSA-N 3-[(3R,12E,21S,22S)-16-ethenyl-11-ethyl-12-(hydroxymethylidene)-3-methoxycarbonyl-17,21,26-trimethyl-4-oxo-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,5(26),6,8,10,13(25),14,16,18(24),19-decaen-22-yl]propanoic acid Chemical compound CCC\1=C2C=C3C(=C4C(=O)[C@@H](C(=C5[C@H]([C@@H](C(=CC6=NC(=CC(=N2)/C1=C/O)C(=C6C)C=C)N5)C)CCC(=O)O)C4=N3)C(=O)OC)C KZTYPOGXRFTJBN-MMLDQJOMSA-N 0.000 description 1
- RKEBXTALJSALNU-LDCXZXNSSA-N 3-[(3R,21S,22S)-16-ethenyl-11-ethyl-4-hydroxy-3-methoxycarbonyl-12,17,21,26-tetramethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid Chemical compound CCC1=C(C2=NC1=CC3=C(C4=C([C@@H](C(=C5[C@H]([C@@H](C(=CC6=NC(=C2)C(=C6C)C=C)N5)C)CCC(=O)O)C4=N3)C(=O)OC)O)C)C RKEBXTALJSALNU-LDCXZXNSSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 241000235389 Absidia Species 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 244000300657 Alchornea rugosa Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000228215 Aspergillus aculeatus Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000589513 Burkholderia cepacia Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 241001355250 Cissus antarctica Species 0.000 description 1
- 241000588923 Citrobacter Species 0.000 description 1
- GCPYCNBGGPHOBD-UHFFFAOYSA-N Delphinidin Natural products OC1=Cc2c(O)cc(O)cc2OC1=C3C=C(O)C(=O)C(=C3)O GCPYCNBGGPHOBD-UHFFFAOYSA-N 0.000 description 1
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 1
- 241000224495 Dictyostelium Species 0.000 description 1
- 241000607473 Edwardsiella <enterobacteria> Species 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 241000588698 Erwinia Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000588724 Escherichia coli Species 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
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000223194 Fusarium culmorum Species 0.000 description 1
- 241000146406 Fusarium heterosporum Species 0.000 description 1
- 241000768015 Gliocladium sp. Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000766694 Hyphozyma Species 0.000 description 1
- GQODBWLKUWYOFX-UHFFFAOYSA-N Isorhamnetin Natural products C1=C(O)C(C)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 GQODBWLKUWYOFX-UHFFFAOYSA-N 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 244000081841 Malus domestica Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241000221960 Neurospora Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 244000271379 Penicillium camembertii Species 0.000 description 1
- 108010076504 Protein Sorting Signals Proteins 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000588768 Providencia Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- 241000235402 Rhizomucor Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000221662 Sclerotinia Species 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000223257 Thermomyces Species 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 241000219095 Vitis Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 244000272739 Vitis cinerea Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 241000607734 Yersinia <bacteria> Species 0.000 description 1
- 241001231403 [Nectria] haematococca Species 0.000 description 1
- 241001223092 [Nectria] haematococca mpVI Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000008714 apigenin Nutrition 0.000 description 1
- KZNIFHPLKGYRTM-UHFFFAOYSA-N apigenin Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 KZNIFHPLKGYRTM-UHFFFAOYSA-N 0.000 description 1
- XADJWCRESPGUTB-UHFFFAOYSA-N apigenin Natural products C1=CC(O)=CC=C1C1=CC(=O)C2=CC(O)=C(O)C=C2O1 XADJWCRESPGUTB-UHFFFAOYSA-N 0.000 description 1
- 229940117893 apigenin Drugs 0.000 description 1
- 235000008452 baby food Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003659 bee venom Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000004883 caffeic acid Nutrition 0.000 description 1
- 229940074360 caffeic acid Drugs 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001746 carotenes Chemical class 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 229930002868 chlorophyll a Natural products 0.000 description 1
- NSMUHPMZFPKNMZ-VBYMZDBQSA-M chlorophyll b Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C=O)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 NSMUHPMZFPKNMZ-VBYMZDBQSA-M 0.000 description 1
- 229930002869 chlorophyll b Natural products 0.000 description 1
- ANWUQYTXRXCEMZ-NYABAGMLSA-L chlorophyllide a Chemical compound C1([C@H](C2=O)C(=O)OC)=C(N3[Mg]N45)C2=C(C)\C3=C\C(=N2)C(CC)=C(C)\C2=C\C4=C(C=C)C(C)=C5\C=C/2[C@@H](C)[C@H](CCC(O)=O)C1=N\2 ANWUQYTXRXCEMZ-NYABAGMLSA-L 0.000 description 1
- QPDWBRHRBKXUNS-IEEIVXFASA-L chlorophyllide b Chemical compound C1([C@H](C2=O)C(=O)OC)=C(N3[Mg]N45)C2=C(C)\C3=C\C(=N2)C(CC)=C(C=O)\C2=C\C4=C(C=C)C(C)=C5\C=C/2[C@@H](C)[C@H](CCC(O)=O)C1=N\2 QPDWBRHRBKXUNS-IEEIVXFASA-L 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 235000007336 cyanidin Nutrition 0.000 description 1
- 235000007242 delphinidin Nutrition 0.000 description 1
- JKHRCGUTYDNCLE-UHFFFAOYSA-O delphinidin Chemical compound [O+]=1C2=CC(O)=CC(O)=C2C=C(O)C=1C1=CC(O)=C(O)C(O)=C1 JKHRCGUTYDNCLE-UHFFFAOYSA-O 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- 235000001785 ferulic acid Nutrition 0.000 description 1
- 229940114124 ferulic acid Drugs 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- 235000011987 flavanols Nutrition 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 229930182486 flavonoid glycoside Natural products 0.000 description 1
- 150000007955 flavonoid glycosides Chemical class 0.000 description 1
- YTAQZPGBTPDBPW-UHFFFAOYSA-N flavonoid group Chemical group O1C(C(C(=O)C2=CC=CC=C12)=O)C1=CC=CC=C1 YTAQZPGBTPDBPW-UHFFFAOYSA-N 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 235000019674 grape juice Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
- IZQSVPBOUDKVDZ-UHFFFAOYSA-N isorhamnetin Chemical compound C1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 IZQSVPBOUDKVDZ-UHFFFAOYSA-N 0.000 description 1
- 235000008800 isorhamnetin Nutrition 0.000 description 1
- 235000008777 kaempferol Nutrition 0.000 description 1
- 235000009498 luteolin Nutrition 0.000 description 1
- LRDGATPGVJTWLJ-UHFFFAOYSA-N luteolin Natural products OC1=CC(O)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 LRDGATPGVJTWLJ-UHFFFAOYSA-N 0.000 description 1
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 description 1
- OAIJSZIZWZSQBC-GYZMGTAESA-N lycopene Chemical compound CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C OAIJSZIZWZSQBC-GYZMGTAESA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- XFDQJKDGGOEYPI-UHFFFAOYSA-O peonidin Chemical compound C1=C(O)C(OC)=CC(C=2C(=CC=3C(O)=CC(O)=CC=3[O+]=2)O)=C1 XFDQJKDGGOEYPI-UHFFFAOYSA-O 0.000 description 1
- 229930015721 peonidin Natural products 0.000 description 1
- 235000006404 peonidin Nutrition 0.000 description 1
- CQIKWXUXPNUNDV-AXRVZGOCSA-N pheophytin a Chemical compound N1C(C=C2[C@H]([C@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C(=N2)C2=C3NC(=C4)C(C)=C3C(=O)[C@@H]2C(=O)OC)C)=C(C)C(C=C)=C1C=C1C(C)=C(CC)C4=N1 CQIKWXUXPNUNDV-AXRVZGOCSA-N 0.000 description 1
- ZQGOYEJYAYJFTL-BTMCAZCFSA-N pheophytin b Chemical compound N1C(C=C2[C@H]([C@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C(=N2)C2=C3NC(=C4)C(C)=C3C(=O)[C@@H]2C(=O)OC)C)=C(C)C(C=C)=C1C=C1C(C=O)=C(CC)C4=N1 ZQGOYEJYAYJFTL-BTMCAZCFSA-N 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- PCMORTLOPMLEFB-UHFFFAOYSA-N sinapinic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-UHFFFAOYSA-N 0.000 description 1
- 239000003998 snake venom Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000005418 vegetable material Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y301/00—Hydrolases acting on ester bonds (3.1)
- C12Y301/01—Carboxylic ester hydrolases (3.1.1)
-
- 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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to an improved method for extraction of plant compounds.
- a number of plant compounds e.g. polyphenols
- desired properties e.g. as antioxidants, colouring or flavouring agent.
- Plant polyphenols may be added to beverages, dairy products, jams, jellies, soups, fruit porridge, preserves and confectionary products.
- a high intake of plant polyphenols is believed to reduce the risk of coronary heart diseases, to lower cholesterol, as well as having an inflammatory effect.
- improved processes for extracting such polyphenols and other plant compounds are highly desirable.
- the present inventors have now discovered that the extraction of plant compounds, e.g. polyphenols from plant material, can be facilitated by contacting the plant material with a lipolytic enzyme, preferably a cutinase.
- a lipolytic enzyme preferably a cutinase.
- the invention provides in a first aspect a process for producing a plant extract comprising incubating a plant material with an enzyme composition comprising a lipolytic enzyme.
- the invention provides in a second aspect a process comprising incubating a plant material with an enzyme composition comprising a lipolytic enzyme, and separating an aqueous liquid from said plant material.
- the invention provides in a third aspect a process for extraction of a compound from a plant material comprising incubating said plant material with an enzyme composition comprising a lipolytic enzyme, and separating an aqueous liquid from said plant material, said liquid comprising said compound.
- a lipolytic enzyme preferably a cutinase
- more of the plant solids can be solubilized and brought into suspension in an aqueous liquid.
- the aqueous liquid separated from the enzyme treated plant material may comprise one or more compounds.
- the compound may be any compound present in a plant material.
- the compound may be a desired compound having any desired property, e.g. as antioxidative, colouring or flavouring.
- the compound may be selected from the group consisting of 5-(hydroxymethyl)-2 furaldehyde, benzoeic acid, cinnamic acid; phenols, preferably benzoic acid derivatives or cinnamic acid derivatives, more preferably glycosyl benzoates, glycosyl cinnamates, salicylic acid, isovanillic acid, gallic acid, coumaric acid, ferulic acid, caffeic acid, sinapic acid, sinapine; polyphenols, preferably stilbene derivatives or flavonoides, more preferably stilbeneols flavonols anthocyanins isoflavones flators, most preferably stilbenol glycosides, flavan
- the plant material may be any plant material, i.e. vegetable material, comprising a desired compound.
- Preferred plant material may be derived from berries, pome, citrus fruit, drupes, vegetables, and seed.
- the plant material preferably comprises material from one or more plant selected from the list comprising grapes (red and green), cranberry, black currant, red currants, lingonberry, elderberry, blueberry, bilberry, gooseberry, crowberry, raspberry, strawberry, blackberry, kiwi, lemon, orange, lime, cherry, plum, peach, mango, apples, pears, carrots, black carrots, lettuce, cabbage, red cabbage, cauliflower, broccoli, leak, celery, onion, garlic, ginseng, pepper fruit, chilli, tomato, tea, spinach, ginko biloba, pepper (black or white), coffe berries, coffee beans, rape seed, canola.
- the pH during the extraction step a) is not critical. However, most of the other desired compounds are pH unstable. Examples of pH unstable compounds are cinnamoyl derivatives, flavonoids and flavonoid glycosides.
- the pH during the incubation in step a) is preferably no more than pH 7.0, no more than pH 6.5, or even no more than pH 6.0, such as no more than pH 5.5.
- the pH is at least 3.0, at least 3.5, or even at least 4.0.
- the plant material is preferably macerated the prior to or during step a) to reduce the particle size and increase extraction.
- pulp or pomace from fruit processing e.g. grape pomace, such as a by-product from wine making, comprising the seeds and skin of the grape and the compound may be polyphenols, such as flavonoids.
- the plant material may be the residues from a juice process, i.e. the pulp, e.g. black currant pulp or apple pulp.
- Also preferred as a plant material is any fraction of a plant comprising skin or seed of fruits or vegetables as these parts are especially rich in e.g. polyphenols and/or carotenoides.
- the plant material may prior to or simultaneous with the incubation during step a) be contacted with a second enzyme, e.g. a pectinase, and/or a cellulase.
- a second enzyme e.g. a pectinase, and/or a cellulase.
- the process of the present invention may be integrated in a process for production of vegetable products such as fruit juice, jams, jellies, soups, fruit porridge, preserves, thereby increasing the content of the desired compound in the vegetable products.
- the plant material may be incubated with additional enzymes, such as e.g. pectinases, as well as with a lipolytic enzyme, preferably a cutinase, according to the present invention.
- additional enzymes such as e.g. pectinases, as well as with a lipolytic enzyme, preferably a cutinase, according to the present invention.
- the process of the present invention may be integrated in a wine making process thereby increasing the content of polyphenols in the grape juice and in the wine following fermentation.
- all, or substantially all the plant material is solubilized and brought into suspension in the aqueous liquid.
- the desired compound may be added to or used in beverages, dairy products, infant foods, juice, jams, jellies, soups, fruit porridge preserves and/or confectionary products.
- a lipolytic enzyme is an enzyme which is capable of hydrolyzing carboxylic ester bonds to release a carboxylic acid or carboxylate (EC 3.1.1), e.g. a lipase, a phospholipase, a cutinase.
- the lipolytic enzymes may be prokaryotic, particularly bacterial, or eukaryotic, e.g. from fungal or animal sources. Lipolytic enzymes may be derived, e.g. from the following genera or species: Thermomyces, T. lanuginosus (also known as Humicola lanuginosa), Humicola, H. insolens, Fusarium, F. oxysporum, F. solani, F. heterosporum, Aspergillus, A. tubigensis, A. niger, A. oryzae, Rhizomucor, Candida, C. antarctica, C. rugosa, Penicillium, P.
- Thermomyces T. lanuginosus (also known as Humicola lanuginosa), Humicola, H. insolens, Fusarium, F. oxysporum, F. solani, F. heterosporum, Aspergillus, A. tubigensis, A. niger
- lipolytic enzymes Some particular examples of lipolytic enzymes are listed as follows:
- Phospholipase from Aspergillus oryzae EP 575133, JP-A 10-155493
- Hyphozyma U.S. Pat. No. 6127137
- Lipase from Themomyces lanuginosus also called Humicola lanuginosa
- EP 305216 U.S. Pat. No. 5869438
- A. tubigensis WO 9845453
- Fusarium solani U.S. Pat. No. 5990069.
- Lipolytic enzyme from F. culmorum (U.S. Pat. No. 5830736) or as described in WO 02/00852 (PCT/DK 01/00448) or DK PA 2001 00304.
- Preferred for the present invention are lipolytic enzymes having activity at acid pH, e.g. at pH 7 and below, such as from pH 2 to pH 7, e.g. from pH 3 to pH 5.
- the lipolytic enzyme is a cutinase.
- a cutinase is an enzyme classified as EC 3.1.1.74.
- the cutinase to be used for the present invention may be of any origin including mammalian, plant or animal origin it is preferred that the cutinase is of microbial origin.
- the cutinase may be one derivable from a filamentous fungus or a yeast.
- Preferred for the present invention are cutinases having activity at acid pH, e.g. at pH 7 and below, such as from pH 2 to pH 7, e.g. from pH 3 to pH 5.
- a cutinase derived from Humicola insolens e.g. such as a cutinase encoded by the DNA sequence shown in SEQ ID NO:1 or SEQ ID NO:2, or any sequence being at least 50 %, preferably at least 60 %, more preferably at least 70 %, most preferably at least 80 %, or even at least 90 %, such as at least 95 % identical to the sequence shown in SEQ ID NO:1 or SEQ ID NO:2, or to a fragment thereof, said fragment having cutinase activity.
- a cutinase derived from Humicola insolens e.g. such as a cutinase encoded by the DNA sequence shown in SEQ ID NO:1 or SEQ ID NO:2, or any sequence being at least 50 %, preferably at least 60 %, more preferably at least 70 %, most preferably at least 80 %, or even at least 90 %, such as at least 95 % identical to the sequence shown in SEQ ID NO
- a cutinase derived from Fusarium solani f.sp. pisi ⁇ Nectria haematococca e.g. a cutinase according to WO 94/14964.
- polypeptide identity is understood as the degree of identity between two sequences indicating a derivation of the first sequence from the second.
- the degree of identity may suitably be determined by means of computer programs known in the art such as GAP provided in the GCG program package (Program Manual for the Wisconsin Package, Version 8, August 1994, Genetics Computer Group, 575 Science Drive, Madison, Wisconsin, USA 53711) (Needleman, S.B. and Wunsch, CD., (1970), Journal of Molecular Biology, 48, 443-453.
- GAP creation penalty of 3.0
- GAP extension penalty of 0.1.
- the relevant part of the amino acid sequence for the homology determination is the mature polypeptide, i.e. without the signal peptide.
- the lipolytic enzyme and/or cutinase activity may be determined as lipolytic activity using tributyrine as substrate.
- the method is based on the rate at which the enzyme hydrolyses tributyrin to form butyric acid.
- the butyric acid is titrated with hydroxide and the consumption of the latter is recorded as a function of time.
- One Lipase Unit (LU) is defined as the amount of enzyme which, under standard conditions (i.e. at 30.O 0 C; pH 7.0; with Gum Arabic as emulsifier and tributyrine as substrate) liberates 1 micromol titrable butyric acid per minute.
- a cutinase composition comprising the polypeptide shown in SEQ ID NO:2 derived from Humicola insolens.
- a pectinase, - a composition produced from a strain of Aspergillus aculeatus comprising polygalacturonase activity 26.000 PG/ml (Pectinex® Ultra SP-L).
- Example 1 Extraction of polyphenols and anthocyanins from black currant pomace using cutinases from Humicola insolens.
- 5.0 gram black currant pomace was mixed with 25.0 mL 100 mM acetate buffer pH 5.8 in 50 mL centrifuge vials and 1.00 mL enzyme solution (15000 LU/ml) or blank was added prior to incubation in a waterbath at 40 0 C for 120 min.
- the enzyme used was a cutinase encoded by the DNA sequence shown herein as SEQ ID NO:1. After incubation the samples were centrifuged at 3500 rpm for 15 min. at 4 0 C and the supernatant was decanted. Sugar content (°Brix), turbidity (NTU), and pH were measured directly.
- the cutinase increased the extraction yield of polyphenols by 8 % and anthocyanins by 28 % relative to the blank sample.
- pectinase and cutinase the polyphenol yield increased 19 % relative to the blank treatment.
- the pectinase alone does not change the concentration of the phenolics in the extract.
- the cutinase increases the extraction yield of polyphenols by 8 % and anthocyanins by 21 % relative to the blank sample. Using cutinase in combination with pectinase the polyphenol yield is further increased.
- Apple peel (Danish lngrid Marie apples) was extracted as in the previous example except that 2.5 gram apple peel was suspended in 20 ml_ 0.1 M acetate buffer pH 5.5.
- pectinase alone does not increase extraction of the phenolics. Both cutinases increase the extraction yield of polyphenols by > 20 % but does not influence the yield of anthocyanins. Applying cutinase in combination with pectinase increases both polyphenol and anthocyanin yields.
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DKPA200500578 | 2005-04-21 | ||
DKPA200500578 | 2005-04-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006111163A1 true WO2006111163A1 (en) | 2006-10-26 |
Family
ID=36250935
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/DK2006/000081 WO2006111163A1 (en) | 2005-04-21 | 2006-02-13 | Plant extraction process |
Country Status (2)
Country | Link |
---|---|
CN (1) | CN101163417A (en) |
WO (1) | WO2006111163A1 (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2033528A2 (en) * | 2007-07-04 | 2009-03-11 | Beijing Gingko Group Biological Technology Co., Ltd. | Lingonberry extract, the preparing method and use thereof |
WO2009124879A2 (en) * | 2008-04-07 | 2009-10-15 | Fluxome Sciences A/S | Production of stilbenoids |
CN102649879A (en) * | 2011-02-25 | 2012-08-29 | 苏州宝泽堂医药科技有限公司 | Method for extracting haematochrome from blackberry fruit |
CN103073532A (en) * | 2012-11-28 | 2013-05-01 | 北京林业大学 | Processing method for increasing blueberry anthocyanidin content and purity |
DE102011085659A1 (en) | 2011-11-03 | 2013-05-08 | Tridonic Gmbh & Co. Kg | Clocked heating circuit for control gear for lamps |
CN104262423A (en) * | 2014-09-30 | 2015-01-07 | 桂林三宝药业有限公司 | Method for extracting phlorhizin from litchi rind |
WO2015082191A1 (en) * | 2013-12-06 | 2015-06-11 | Unilever N.V. | A process for producing a tea product |
CN104892700A (en) * | 2015-06-11 | 2015-09-09 | 威海紫光科技园有限公司 | Method for extracting anthocyanin from cherries |
US9404129B2 (en) | 2005-02-22 | 2016-08-02 | Evolva Sa | Metabolically engineered cells for the production of resveratrol or an oligomeric or glycosidically-bound derivative thereof |
US9579618B2 (en) | 2015-06-17 | 2017-02-28 | Christos Ritzoulis | Emulsifiers from grape processing by-products |
US9725743B2 (en) | 2006-07-20 | 2017-08-08 | Evolva Sa | Metabolically engineered cells for the production of pinosylvin |
US9822374B2 (en) | 2010-05-26 | 2017-11-21 | Evolva Sa | Production of metabolites |
US9951299B2 (en) | 2013-12-11 | 2018-04-24 | Novozymes A/S | Cutinase variants and polynucleotides encoding same |
US10294499B2 (en) | 2015-05-28 | 2019-05-21 | Evolva Sa | Biosynthesis of phenylpropanoids and phenylpropanoid derivatives |
CN115716854A (en) * | 2022-10-18 | 2023-02-28 | 云南博瑞生物科技有限公司 | Method for extracting polyphenol from purple lettuce |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102038014B (en) * | 2011-01-18 | 2013-11-06 | 上海交通大学 | Compound plant-source acaricide and preparation method thereof |
CN102304296A (en) * | 2011-06-23 | 2012-01-04 | 张家港市鸿钻贸易有限公司 | Method for preparing dye by plum peel and application thereof |
CN103445159B (en) * | 2013-08-11 | 2016-03-02 | 吉林农业大学 | A kind of enzymatic-process preparation method of full constituent ginseng juice |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6368511A (en) * | 1986-09-11 | 1988-03-28 | Nippon Terupen Kagaku Kk | Cosmetic |
JPH01300848A (en) * | 1988-05-27 | 1989-12-05 | Osaka Gas Co Ltd | Treatment of tea leaf |
WO1991000022A1 (en) * | 1989-06-23 | 1991-01-10 | Genencor International, Inc. | Enzyme assisted degradation of surface membranes of harvested fruits and vegetables |
DD288980A5 (en) * | 1989-11-15 | 1991-04-18 | Adw Zi F. Ernaehrung,De | METHOD OF TREATING OIL SEEDS, LEGUMINOSES AND CEREALS FOR THE OBTAINMENT OF BULB MATERIALS |
GB2262213A (en) * | 1991-12-12 | 1993-06-16 | Tanisake Kk | Supplementary nourishment |
JPH07274977A (en) * | 1994-04-14 | 1995-10-24 | Shikoku Sogo Kenkyusho:Kk | Extraction of useful plant essence, plant essence obtained by the extraction and skin-improving product containing the same essence as the active component |
US5728384A (en) * | 1993-02-16 | 1998-03-17 | Soken Co., Ltd. | Antiulcer agent |
EP1142485A2 (en) * | 1994-04-22 | 2001-10-10 | Novozymes A/S | A method for improving the solubility of vegetable proteins |
CN1394869A (en) * | 2002-07-22 | 2003-02-05 | 张万举 | dioscin and extraction method of diosgenin |
US6620452B1 (en) * | 2000-05-05 | 2003-09-16 | American Fruit And Flavors | Food additives having enlarged concentration of phenolics extracted from fruits and vegetables and process of obtaining the same |
WO2003106486A1 (en) * | 2002-06-12 | 2003-12-24 | Fraunhofer-Gelellschaft Zur Förderung Der Angewandten Forschung E.V. | Vegetable protein preparations and use thereof |
-
2006
- 2006-02-13 CN CNA2006800134512A patent/CN101163417A/en active Pending
- 2006-02-13 WO PCT/DK2006/000081 patent/WO2006111163A1/en active Application Filing
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6368511A (en) * | 1986-09-11 | 1988-03-28 | Nippon Terupen Kagaku Kk | Cosmetic |
JPH01300848A (en) * | 1988-05-27 | 1989-12-05 | Osaka Gas Co Ltd | Treatment of tea leaf |
WO1991000022A1 (en) * | 1989-06-23 | 1991-01-10 | Genencor International, Inc. | Enzyme assisted degradation of surface membranes of harvested fruits and vegetables |
DD288980A5 (en) * | 1989-11-15 | 1991-04-18 | Adw Zi F. Ernaehrung,De | METHOD OF TREATING OIL SEEDS, LEGUMINOSES AND CEREALS FOR THE OBTAINMENT OF BULB MATERIALS |
GB2262213A (en) * | 1991-12-12 | 1993-06-16 | Tanisake Kk | Supplementary nourishment |
US5728384A (en) * | 1993-02-16 | 1998-03-17 | Soken Co., Ltd. | Antiulcer agent |
JPH07274977A (en) * | 1994-04-14 | 1995-10-24 | Shikoku Sogo Kenkyusho:Kk | Extraction of useful plant essence, plant essence obtained by the extraction and skin-improving product containing the same essence as the active component |
EP1142485A2 (en) * | 1994-04-22 | 2001-10-10 | Novozymes A/S | A method for improving the solubility of vegetable proteins |
US6620452B1 (en) * | 2000-05-05 | 2003-09-16 | American Fruit And Flavors | Food additives having enlarged concentration of phenolics extracted from fruits and vegetables and process of obtaining the same |
WO2003106486A1 (en) * | 2002-06-12 | 2003-12-24 | Fraunhofer-Gelellschaft Zur Förderung Der Angewandten Forschung E.V. | Vegetable protein preparations and use thereof |
CN1394869A (en) * | 2002-07-22 | 2003-02-05 | 张万举 | dioscin and extraction method of diosgenin |
Non-Patent Citations (4)
Title |
---|
DATABASE WPI Section Ch Week 200382, Derwent World Patents Index; Class B03, AN 2003-878079, XP002380901 * |
PATENT ABSTRACTS OF JAPAN vol. 012, no. 299 (C - 520) 15 August 1988 (1988-08-15) * |
PATENT ABSTRACTS OF JAPAN vol. 014, no. 086 (C - 0690) 19 February 1990 (1990-02-19) * |
PATENT ABSTRACTS OF JAPAN vol. 1996, no. 02 29 February 1996 (1996-02-29) * |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9404129B2 (en) | 2005-02-22 | 2016-08-02 | Evolva Sa | Metabolically engineered cells for the production of resveratrol or an oligomeric or glycosidically-bound derivative thereof |
US9834793B2 (en) | 2005-02-22 | 2017-12-05 | Evolva Sa | Metabolically engineered cells for the production of resveratrol or an oligomeric or glycosidically-bound derivative thereof |
US9725743B2 (en) | 2006-07-20 | 2017-08-08 | Evolva Sa | Metabolically engineered cells for the production of pinosylvin |
EP2033528A3 (en) * | 2007-07-04 | 2012-12-26 | Beijing Gingko Group Biological Technology Co., Ltd. | Lingonberry extract, the preparing method and use thereof |
EP2033528A2 (en) * | 2007-07-04 | 2009-03-11 | Beijing Gingko Group Biological Technology Co., Ltd. | Lingonberry extract, the preparing method and use thereof |
WO2009124879A2 (en) * | 2008-04-07 | 2009-10-15 | Fluxome Sciences A/S | Production of stilbenoids |
WO2009124879A3 (en) * | 2008-04-07 | 2009-12-03 | Fluxome Sciences A/S | Production of stilbenoids |
US8569024B2 (en) | 2008-04-07 | 2013-10-29 | Evolva Sa | Production of stilbenoids |
US9822374B2 (en) | 2010-05-26 | 2017-11-21 | Evolva Sa | Production of metabolites |
CN102649879A (en) * | 2011-02-25 | 2012-08-29 | 苏州宝泽堂医药科技有限公司 | Method for extracting haematochrome from blackberry fruit |
DE102011085659A1 (en) | 2011-11-03 | 2013-05-08 | Tridonic Gmbh & Co. Kg | Clocked heating circuit for control gear for lamps |
CN103073532A (en) * | 2012-11-28 | 2013-05-01 | 北京林业大学 | Processing method for increasing blueberry anthocyanidin content and purity |
WO2015082191A1 (en) * | 2013-12-06 | 2015-06-11 | Unilever N.V. | A process for producing a tea product |
US9951299B2 (en) | 2013-12-11 | 2018-04-24 | Novozymes A/S | Cutinase variants and polynucleotides encoding same |
CN104262423A (en) * | 2014-09-30 | 2015-01-07 | 桂林三宝药业有限公司 | Method for extracting phlorhizin from litchi rind |
US10294499B2 (en) | 2015-05-28 | 2019-05-21 | Evolva Sa | Biosynthesis of phenylpropanoids and phenylpropanoid derivatives |
CN104892700A (en) * | 2015-06-11 | 2015-09-09 | 威海紫光科技园有限公司 | Method for extracting anthocyanin from cherries |
US9579618B2 (en) | 2015-06-17 | 2017-02-28 | Christos Ritzoulis | Emulsifiers from grape processing by-products |
CN115716854A (en) * | 2022-10-18 | 2023-02-28 | 云南博瑞生物科技有限公司 | Method for extracting polyphenol from purple lettuce |
CN115716854B (en) * | 2022-10-18 | 2024-03-15 | 云南博瑞生物科技有限公司 | Method for extracting polyphenol from lettuce |
Also Published As
Publication number | Publication date |
---|---|
CN101163417A (en) | 2008-04-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2006111163A1 (en) | Plant extraction process | |
Sharma et al. | Enzymatic extraction and clarification of juice from various fruits–a review | |
Sharma et al. | Enzymatic added extraction and clarification of fruit juices–A review | |
Sandri et al. | Clarification of fruit juices by fungal pectinases | |
Zambrano et al. | Mobilization of phenolic antioxidants from grape, apple and pitahaya residues via solid state fungal fermentation and carbohydrase treatment | |
Sandri et al. | Use of pectinases produced by a new strain of Aspergillus niger for the enzymatic treatment of apple and blueberry juice | |
Kashyap et al. | Applications of pectinases in the commercial sector: a review | |
Kammerer et al. | A novel process for the recovery of polyphenols from grape (Vitis vinifera L.) pomace | |
Fang et al. | How to improve bayberry (Myrica rubra Sieb. et Zucc.) juice color quality: effect of juice processing on bayberry anthocyanins and polyphenolics | |
Murthy et al. | Improvement of robusta coffee fermentation with microbial enzymes | |
Singh et al. | Enzymatic processing of juice from fruits/vegetables: An emerging trend and cutting edge research in food biotechnology | |
Pinto et al. | Castanea sativa shells: A review on phytochemical composition, bioactivity and waste management approaches for industrial valorization | |
Srivastava et al. | Application of immobilized tannase from Aspergillus niger for the removal of tannin from myrobalan juice | |
Danalache et al. | Enzyme-assisted extraction of fruit juices | |
Soares et al. | Pectinolytic enzyme production by Bacillus species and their potential application on juice extraction | |
Ramadan | Enzymes in fruit juice processing | |
Toy et al. | Enzymatic treatment, unfermented and fermented fruit-based products: Current state of knowledge | |
Zhu et al. | Ultrasonic and other sterilization methods on nutrition and flavor of cloudy apple juice | |
García | Application of enzymes for fruit juice processing | |
Tsouko et al. | Valorization of Zante currant side‐streams for the production of phenolic‐rich extract and bacterial cellulose: a novel biorefinery concept | |
Xavier Machado et al. | New trends in the use of enzymes for the recovery of polyphenols in grape byproducts | |
Suhaimi et al. | Fungal pectinases: Production and applications in food industries | |
Cubero-Cardoso et al. | Valorization options of strawberry extrudate agro-waste. A review | |
Kundu et al. | A sustainable process for nutrient enriched fruit juice processing: an enzymatic venture | |
Phing et al. | Enzyme-Aided Treatment of Fruit Juice: A Review |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 4660/CHENP/2007 Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 200680013451.2 Country of ref document: CN |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: DE |
|
NENP | Non-entry into the national phase |
Ref country code: RU |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: RU |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 06706052 Country of ref document: EP Kind code of ref document: A1 |