CS241456B2 - Method of phenols and oligosacharides from plant tissues extraction - Google Patents
Method of phenols and oligosacharides from plant tissues extraction Download PDFInfo
- Publication number
- CS241456B2 CS241456B2 CS761179A CS117976A CS241456B2 CS 241456 B2 CS241456 B2 CS 241456B2 CS 761179 A CS761179 A CS 761179A CS 117976 A CS117976 A CS 117976A CS 241456 B2 CS241456 B2 CS 241456B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- protein
- extraction
- acid
- solvent
- flour
- Prior art date
Links
- 238000000605 extraction Methods 0.000 title claims abstract description 40
- 150000002989 phenols Chemical class 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 36
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 72
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 72
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229920001542 oligosaccharide Polymers 0.000 claims abstract description 22
- 150000002482 oligosaccharides Chemical class 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 239000003792 electrolyte Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000004925 denaturation Methods 0.000 claims description 5
- 230000036425 denaturation Effects 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 239000008151 electrolyte solution Substances 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 235000013312 flour Nutrition 0.000 abstract description 31
- 235000020238 sunflower seed Nutrition 0.000 abstract description 15
- 235000010469 Glycine max Nutrition 0.000 abstract description 11
- 244000068988 Glycine max Species 0.000 abstract description 10
- 235000012343 cottonseed oil Nutrition 0.000 abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 235000013311 vegetables Nutrition 0.000 abstract description 4
- -1 A2Q Phenols Chemical class 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 150000002576 ketones Chemical class 0.000 abstract description 2
- QBKSWRVVCFFDOT-UHFFFAOYSA-N gossypol Chemical compound CC(C)C1=C(O)C(O)=C(C=O)C2=C(O)C(C=3C(O)=C4C(C=O)=C(O)C(O)=C(C4=CC=3C)C(C)C)=C(C)C=C21 QBKSWRVVCFFDOT-UHFFFAOYSA-N 0.000 description 32
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 25
- 239000012141 concentrate Substances 0.000 description 25
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 24
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 24
- 235000001368 chlorogenic acid Nutrition 0.000 description 24
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 24
- 229940074393 chlorogenic acid Drugs 0.000 description 24
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 24
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 235000012054 meals Nutrition 0.000 description 22
- 229950005277 gossypol Drugs 0.000 description 17
- QHOPXUFELLHKAS-UHFFFAOYSA-N Thespesin Natural products CC(C)c1c(O)c(O)c2C(O)Oc3c(c(C)cc1c23)-c1c2OC(O)c3c(O)c(O)c(C(C)C)c(cc1C)c23 QHOPXUFELLHKAS-UHFFFAOYSA-N 0.000 description 16
- 229930000755 gossypol Natural products 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 239000000835 fiber Substances 0.000 description 12
- 235000013305 food Nutrition 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 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 12
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 11
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 11
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 11
- 229930006000 Sucrose Natural products 0.000 description 10
- CZMRCDWAGMRECN-UGDNZRGBSA-N 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 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 239000005720 sucrose Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 150000002632 lipids Chemical class 0.000 description 9
- 239000006228 supernatant Substances 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 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 6
- 235000004883 caffeic acid Nutrition 0.000 description 6
- 229940074360 caffeic acid Drugs 0.000 description 6
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 5
- 235000013824 polyphenols Nutrition 0.000 description 5
- 238000000751 protein extraction Methods 0.000 description 5
- 238000007792 addition Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001962 electrophoresis Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 229960004793 sucrose Drugs 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
- 241000208818 Helianthus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 235000019764 Soybean Meal Nutrition 0.000 description 2
- 235000019772 Sunflower meal Nutrition 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003593 chromogenic compound Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000012460 protein solution Substances 0.000 description 2
- 150000004053 quinones Chemical class 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
- 239000004455 soybean meal Substances 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 2
- CWVRJTMFETXNAD-BMNNCGMMSA-N (1s,3r,4s,5r)-3-[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid Chemical compound O[C@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-BMNNCGMMSA-N 0.000 description 1
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-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
- AXAVXPMQTGXXJZ-UHFFFAOYSA-N 2-aminoacetic acid;2-amino-2-(hydroxymethyl)propane-1,3-diol Chemical compound NCC(O)=O.OCC(N)(CO)CO AXAVXPMQTGXXJZ-UHFFFAOYSA-N 0.000 description 1
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 description 1
- 206010000060 Abdominal distension Diseases 0.000 description 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 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
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- QURCVMIEKCOAJU-HWKANZROSA-N Isoferulic acid Natural products COC1=CC=C(\C=C\C(O)=O)C=C1O QURCVMIEKCOAJU-HWKANZROSA-N 0.000 description 1
- 238000007696 Kjeldahl method Methods 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- 241000201976 Polycarpon Species 0.000 description 1
- 102000003425 Tyrosinase Human genes 0.000 description 1
- 108060008724 Tyrosinase Proteins 0.000 description 1
- LJKDPUCDUDLUOM-UHFFFAOYSA-N [3,8-diacetyloxy-1-formyl-6-methyl-4-propan-2-yl-7-(1,6,7-triacetyloxy-8-formyl-3-methyl-5-propan-2-ylnaphthalen-2-yl)naphthalen-2-yl] acetate Chemical compound CC(C)C1=C(OC(C)=O)C(OC(C)=O)=C(C=O)C2=C(OC(C)=O)C(C=3C(OC(C)=O)=C4C(C=O)=C(OC(C)=O)C(OC(C)=O)=C(C4=CC=3C)C(C)C)=C(C)C=C21 LJKDPUCDUDLUOM-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000000433 anti-nutritional effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 208000024330 bloating Diseases 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000002021 butanolic extract Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 235000013861 fat-free Nutrition 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
- 238000001914 filtration Methods 0.000 description 1
- 206010016766 flatulence Diseases 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- KRZBCHWVBQOTNZ-DLDRDHNVSA-N isochlorogenic acid Natural products O[C@@H]1[C@H](C[C@@](O)(C[C@H]1OC(=O)C=Cc2ccc(O)c(O)c2)C(=O)O)OC(=O)C=Cc3ccc(O)c(O)c3 KRZBCHWVBQOTNZ-DLDRDHNVSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000013627 low molecular weight specie Substances 0.000 description 1
- 230000014759 maintenance of location Effects 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
- 239000005445 natural material Substances 0.000 description 1
- 235000021095 non-nutrients Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 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
- 239000007790 solid phase Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J1/00—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites
- A23J1/14—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites from leguminous or other vegetable seeds; from press-cake or oil-bearing seeds
- A23J1/142—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites from leguminous or other vegetable seeds; from press-cake or oil-bearing seeds by extracting with organic solvents
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Plant Substances (AREA)
- Extraction Or Liquid Replacement (AREA)
- Saccharide Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20504/75A IT1031932B (it) | 1975-02-21 | 1975-02-21 | Processo di estrazione di composti fenolici dai vegetali che li contengono |
| IT1924076A IT1054941B (it) | 1976-01-14 | 1976-01-14 | Processo diestrazione di fenoli ed oligosaccaridi da tessuti vegetali |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS117976A2 CS117976A2 (en) | 1984-06-18 |
| CS241456B2 true CS241456B2 (en) | 1986-03-13 |
Family
ID=26327106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS761179A CS241456B2 (en) | 1975-02-21 | 1976-02-23 | Method of phenols and oligosacharides from plant tissues extraction |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4072671A (OSRAM) |
| JP (1) | JPS51108100A (OSRAM) |
| AR (1) | AR212020A1 (OSRAM) |
| AU (1) | AU500086B2 (OSRAM) |
| BG (1) | BG24939A3 (OSRAM) |
| CA (1) | CA1066696A (OSRAM) |
| CS (1) | CS241456B2 (OSRAM) |
| DD (1) | DD123156A5 (OSRAM) |
| DE (1) | DE2606961C3 (OSRAM) |
| DK (1) | DK72376A (OSRAM) |
| EG (1) | EG12238A (OSRAM) |
| ES (1) | ES445653A1 (OSRAM) |
| FR (1) | FR2302694A1 (OSRAM) |
| GB (1) | GB1515591A (OSRAM) |
| IL (1) | IL49059A (OSRAM) |
| KE (1) | KE3040A (OSRAM) |
| MX (1) | MX3258E (OSRAM) |
| NL (1) | NL175023C (OSRAM) |
| PL (1) | PL100130B1 (OSRAM) |
| PT (1) | PT64826B (OSRAM) |
| RO (1) | RO78223A (OSRAM) |
| SE (1) | SE7601543L (OSRAM) |
| TR (1) | TR19523A (OSRAM) |
| YU (1) | YU36854B (OSRAM) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1039861B (it) | 1975-07-15 | 1979-12-10 | Snam Progetti | Processo di estrazione di micotossine da farine di natura vegetalemarco canella e giancarlo sodini |
| IT1098309B (it) * | 1978-06-02 | 1985-09-07 | Snam Progetti | Processo per la preparazione di isolato proteico da farina di girasole |
| US4211694A (en) * | 1978-07-07 | 1980-07-08 | The Procter & Gamble Company | Deflavoring vegetable seed materials |
| US4215040A (en) * | 1978-12-22 | 1980-07-29 | The Procter & Gamble Company | Density separation process |
| IT1144945B (it) * | 1981-11-19 | 1986-10-29 | Anic Spa | Estrazione contemporanea di lipidi e polifenoli da mandorle laminate di girasole |
| US4515818A (en) * | 1982-03-03 | 1985-05-07 | Csp Foods Ltd. | Process for preparing sunflower butter spread from pretreated sunflower seeds |
| FR2657539B1 (fr) * | 1990-01-29 | 1992-04-03 | Commissariat Energie Atomique | Procede d'extraction des constituants d'une matiere vegetale utilisant des solvants selectifs. |
| CA2013190C (en) * | 1990-03-27 | 2000-06-06 | F. William Collins | Method of producing stable bran and flour products from cereal grains |
| US5112637A (en) * | 1990-11-05 | 1992-05-12 | The United States Of America As Represented By The Secretary Of Agriculture | Extraction of gossypol from cottonseed |
| US5340483A (en) * | 1993-06-11 | 1994-08-23 | University Of Maryland At College Park | Two step process for conversion of a weakly adsorbable compound to a strongly adsorbable compound and selective removal thereof |
| US5906848A (en) * | 1995-03-06 | 1999-05-25 | Emil Flachsmann Ag | Process for the removal of undesired contaminations and/or residues contained in beverages or in vegetable preparation |
| DK1046719T3 (da) * | 1999-04-20 | 2004-09-20 | Cargill Bv | D-galactosesammensætning og fremgangsmåde til fremstilling deraf |
| NL1017241C2 (nl) * | 2001-01-30 | 2002-07-31 | Tno | Werkwijze voor het bereiden van een eiwitpreparaat met verlaagd gehalte aan fenolische verbindingen. |
| NZ515182A (en) * | 2001-10-31 | 2004-03-26 | Brightwater Horticulture Ltd | Extraction of biologically active compounds from plant material using acid and antioxidant |
| DE102007022662A1 (de) * | 2007-05-15 | 2008-11-20 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Phenolextrakte aus Ölsaaten |
| US8734867B2 (en) | 2007-12-28 | 2014-05-27 | Liveleaf, Inc. | Antibacterial having an extract of pomegranate combined with hydrogen peroxide |
| WO2009094169A1 (en) * | 2008-01-24 | 2009-07-30 | Vitae Pharmaceuticals, Inc. | Cyclic carbazate and semicarbazide inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| BRPI1006287A2 (pt) | 2009-03-04 | 2015-08-25 | Metaactiv Inc | Composição botânica e aditivada por local, método de tratamento prevenção ou aperfeiçoamento dos sintomas de um distúrbio gástrico, método de tratamento da água potável, de uma infecção, de uma ferida, de desinfecção de uma superfície, de preservação de um alimento, e, de melhora da função gástrica de um animal; e kit |
| US20110214318A1 (en) * | 2010-03-05 | 2011-09-08 | Sony Ericsson Mobile Communications Ab | Paper Stock Card with Wireless Communication Capability |
| US9192635B2 (en) | 2011-06-24 | 2015-11-24 | Liveleaf, Inc. | Method of treating damaged mucosal or gastrointestinal tissue by administering a composition comprising a mixture of pomegranate and green tea extracts and releasably bound hydrogen peroxide |
| US8722040B2 (en) | 2011-06-24 | 2014-05-13 | Liveleaf, Inc. | Site-activated binding systems that selectively increase the bioactivity of phenolic compounds at target sites |
| US8716351B1 (en) | 2012-12-23 | 2014-05-06 | Liveleaf, Inc. | Methods of treating gastrointestinal spasms |
| JP6129762B2 (ja) * | 2013-10-04 | 2017-05-17 | 富士フイルム株式会社 | クロロゲン酸含有組成物の製造方法 |
| EP3878434A1 (en) * | 2020-03-12 | 2021-09-15 | Lipoid GmbH | Sunflower phospholipid composition containing phosphatidylcholine |
| CN116492266B (zh) * | 2023-06-12 | 2024-12-10 | 广西中医药大学 | 一种向日葵籽粕提取物及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3168406A (en) * | 1964-02-03 | 1965-02-02 | Gen Foods Corp | Process for treating soybean flour to improve its flavor |
| US3365440A (en) * | 1965-04-21 | 1968-01-23 | Central Soya Co | Process of non-evaporative countercurrent concentration of solids in the processing of protein and carbohydrate-containing materials from soybeans |
| US3895003A (en) * | 1971-06-25 | 1975-07-15 | Procter & Gamble | Process for producing protein concentrate using air classification |
-
1976
- 1976-02-11 SE SE7601543A patent/SE7601543L/ unknown
- 1976-02-12 AU AU11046/76A patent/AU500086B2/en not_active Expired
- 1976-02-13 CA CA245,737A patent/CA1066696A/en not_active Expired
- 1976-02-18 IL IL49059A patent/IL49059A/xx unknown
- 1976-02-19 AR AR262307A patent/AR212020A1/es active
- 1976-02-19 GB GB6676/76A patent/GB1515591A/en not_active Expired
- 1976-02-19 FR FR7604566A patent/FR2302694A1/fr active Granted
- 1976-02-19 PT PT64826A patent/PT64826B/pt unknown
- 1976-02-19 YU YU0417/76A patent/YU36854B/xx unknown
- 1976-02-20 ES ES445653A patent/ES445653A1/es not_active Expired
- 1976-02-20 DE DE2606961A patent/DE2606961C3/de not_active Expired
- 1976-02-20 DK DK72376*#A patent/DK72376A/da not_active Application Discontinuation
- 1976-02-20 DD DD191385A patent/DD123156A5/xx unknown
- 1976-02-20 US US05/659,749 patent/US4072671A/en not_active Expired - Lifetime
- 1976-02-20 BG BG032413A patent/BG24939A3/xx unknown
- 1976-02-20 JP JP51017143A patent/JPS51108100A/ja active Granted
- 1976-02-21 PL PL1976187402A patent/PL100130B1/pl unknown
- 1976-02-21 RO RO7684892A patent/RO78223A/ro unknown
- 1976-02-21 EG EG107/76A patent/EG12238A/xx active
- 1976-02-23 NL NLAANVRAGE7601828,A patent/NL175023C/xx not_active IP Right Cessation
- 1976-02-23 MX MX000335U patent/MX3258E/es unknown
- 1976-02-23 CS CS761179A patent/CS241456B2/cs unknown
-
1977
- 1977-02-20 TR TR19523A patent/TR19523A/xx unknown
-
1980
- 1980-04-05 KE KE3040A patent/KE3040A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL49059A (en) | 1979-07-25 |
| TR19523A (tr) | 1979-06-27 |
| DE2606961A1 (de) | 1976-09-09 |
| FR2302694A1 (fr) | 1976-10-01 |
| KE3040A (en) | 1980-04-25 |
| AU1104676A (en) | 1977-08-18 |
| PT64826B (en) | 1977-06-07 |
| NL175023C (nl) | 1984-09-17 |
| DK72376A (da) | 1976-08-22 |
| GB1515591A (en) | 1978-06-28 |
| AR212020A1 (es) | 1978-04-28 |
| MX3258E (es) | 1980-08-12 |
| CA1066696A (en) | 1979-11-20 |
| DE2606961C3 (de) | 1981-06-11 |
| YU36854B (en) | 1984-08-31 |
| PT64826A (en) | 1976-03-01 |
| CS117976A2 (en) | 1984-06-18 |
| ES445653A1 (es) | 1977-06-01 |
| JPS6137896B2 (OSRAM) | 1986-08-26 |
| YU41776A (en) | 1982-02-25 |
| IL49059A0 (en) | 1976-04-30 |
| US4072671A (en) | 1978-02-07 |
| FR2302694B1 (OSRAM) | 1978-11-03 |
| NL7601828A (nl) | 1976-08-24 |
| DE2606961B2 (de) | 1980-09-11 |
| BG24939A3 (en) | 1978-06-15 |
| SE7601543L (sv) | 1976-08-23 |
| RO78223A (ro) | 1982-02-01 |
| NL175023B (nl) | 1984-04-16 |
| JPS51108100A (en) | 1976-09-25 |
| AU500086B2 (en) | 1979-05-10 |
| DD123156A5 (OSRAM) | 1976-12-05 |
| PL100130B1 (pl) | 1978-09-30 |
| EG12238A (en) | 1979-09-30 |
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