CA2714084C - Procede de fractionnement permettant d'obtenir des anthocyanines tres pures a partir de fruits et de legumes - Google Patents
Procede de fractionnement permettant d'obtenir des anthocyanines tres pures a partir de fruits et de legumes Download PDFInfo
- Publication number
- CA2714084C CA2714084C CA2714084A CA2714084A CA2714084C CA 2714084 C CA2714084 C CA 2714084C CA 2714084 A CA2714084 A CA 2714084A CA 2714084 A CA2714084 A CA 2714084A CA 2714084 C CA2714084 C CA 2714084C
- Authority
- CA
- Canada
- Prior art keywords
- anthocyanins
- solvent
- resin
- anthocyanin
- resulting mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 235000010208 anthocyanin Nutrition 0.000 title claims abstract description 127
- 239000004410 anthocyanin Substances 0.000 title claims abstract description 127
- 229930002877 anthocyanin Natural products 0.000 title claims abstract description 127
- 150000004636 anthocyanins Chemical class 0.000 title claims abstract description 124
- 235000012055 fruits and vegetables Nutrition 0.000 title description 6
- 238000005194 fractionation Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 60
- 239000002904 solvent Substances 0.000 claims abstract description 31
- 239000011347 resin Substances 0.000 claims abstract description 24
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 6
- 235000013399 edible fruits Nutrition 0.000 claims abstract description 3
- 235000013311 vegetables Nutrition 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 235000013824 polyphenols Nutrition 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 8
- 241001444063 Aronia Species 0.000 claims description 7
- 241000196324 Embryophyta Species 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 235000017537 Vaccinium myrtillus Nutrition 0.000 claims description 6
- 244000078534 Vaccinium myrtillus Species 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 claims description 5
- 240000008042 Zea mays Species 0.000 claims description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 5
- 235000005822 corn Nutrition 0.000 claims description 5
- 244000111388 Rubus occidentalis Species 0.000 claims description 4
- 235000003942 Rubus occidentalis Nutrition 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 235000009754 Vitis X bourquina Nutrition 0.000 claims description 4
- 235000012333 Vitis X labruscana Nutrition 0.000 claims description 4
- 240000006365 Vitis vinifera Species 0.000 claims description 4
- 235000014787 Vitis vinifera Nutrition 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 229920001864 tannin Polymers 0.000 claims description 4
- 235000018553 tannin Nutrition 0.000 claims description 4
- 239000001648 tannin Substances 0.000 claims description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 claims description 3
- 244000178937 Brassica oleracea var. capitata Species 0.000 claims description 3
- 244000000626 Daucus carota Species 0.000 claims description 3
- 235000002767 Daucus carota Nutrition 0.000 claims description 3
- 235000016623 Fragaria vesca Nutrition 0.000 claims description 3
- 240000009088 Fragaria x ananassa Species 0.000 claims description 3
- 235000011363 Fragaria x ananassa Nutrition 0.000 claims description 3
- 240000001890 Ribes hudsonianum Species 0.000 claims description 3
- 235000016954 Ribes hudsonianum Nutrition 0.000 claims description 3
- 235000001466 Ribes nigrum Nutrition 0.000 claims description 3
- 244000151637 Sambucus canadensis Species 0.000 claims description 3
- 235000018735 Sambucus canadensis Nutrition 0.000 claims description 3
- 235000003095 Vaccinium corymbosum Nutrition 0.000 claims description 3
- 235000007123 blue elder Nutrition 0.000 claims description 3
- 235000021014 blueberries Nutrition 0.000 claims description 3
- 235000007124 elderberry Nutrition 0.000 claims description 3
- 235000008995 european elder Nutrition 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 244000061458 Solanum melongena Species 0.000 claims description 2
- 235000002597 Solanum melongena Nutrition 0.000 claims description 2
- 244000061456 Solanum tuberosum Species 0.000 claims description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000006228 supernatant Substances 0.000 claims 3
- 244000088415 Raphanus sativus Species 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 abstract description 8
- 239000002594 sorbent Substances 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- 238000005341 cation exchange Methods 0.000 description 6
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 230000003993 interaction Effects 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 241000220259 Raphanus Species 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- -1 anthocyanin flavylium cation Chemical class 0.000 description 4
- 239000000287 crude extract Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012799 strong cation exchange Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 238000000540 analysis of variance Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- YTMNONATNXDQJF-UBNZBFALSA-N chrysanthemin Chemical compound [Cl-].O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC2=C(O)C=C(O)C=C2[O+]=C1C1=CC=C(O)C(O)=C1 YTMNONATNXDQJF-UBNZBFALSA-N 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
- 230000005593 dissociations Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 238000012313 Kruskal-Wallis test Methods 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000576 food coloring agent Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229930008677 glyco alkaloid Natural products 0.000 description 2
- 230000007407 health benefit Effects 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000000401 methanolic extract Substances 0.000 description 2
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
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- 238000000692 Student's t-test Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
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- 239000006227 byproduct Substances 0.000 description 1
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- 150000001768 cations Chemical class 0.000 description 1
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- 231100000481 chemical toxicant Toxicity 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
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- 238000000605 extraction Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 239000012528 membrane Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002417 nutraceutical Substances 0.000 description 1
- 235000021436 nutraceutical agent Nutrition 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 238000013105 post hoc analysis Methods 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229920002414 procyanidin Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
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- 229940092385 radish extract Drugs 0.000 description 1
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- 235000017550 sodium carbonate Nutrition 0.000 description 1
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- 239000007921 spray Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Saccharide Compounds (AREA)
Abstract
La présente invention concerne un procédé d'isolement d'anthocyanines à teneur nulle en mélange phénolique à partir d'une charge d'alimentation en fruits ou en légumes contenant des anthocyanines et des mélanges phénoliques. La première étape consiste à mettre en contact la charge d'alimentation avec une résine échangeuse de cations à un pH faible et pendant une durée suffisante pour que la résine se lie de façon sélective aux anthocyanines. Ensuite, le mélange phénolique non lié est séparé de la résine en vue du recueil des produits recherchés. La résine liée est soumise à un lavage par solvant afin de libérer les anthocyanines en vue de leur recueil.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6376308P | 2008-02-06 | 2008-02-06 | |
| US61/063,763 | 2008-02-06 | ||
| PCT/US2009/033127 WO2009100165A2 (fr) | 2008-02-06 | 2009-02-05 | Procédé de fractionnement permettant d'obtenir des anthocyanines très pures à partir de fruits et de légumes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2714084A1 CA2714084A1 (fr) | 2009-08-13 |
| CA2714084C true CA2714084C (fr) | 2015-09-29 |
Family
ID=40952675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2714084A Expired - Fee Related CA2714084C (fr) | 2008-02-06 | 2009-02-05 | Procede de fractionnement permettant d'obtenir des anthocyanines tres pures a partir de fruits et de legumes |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA2714084C (fr) |
| WO (1) | WO2009100165A2 (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102443029A (zh) * | 2010-10-01 | 2012-05-09 | 华中农业大学 | 一种高效分离纯化血橙花色苷的柱层析方法 |
| CN102321062A (zh) * | 2011-06-08 | 2012-01-18 | 吉林市新科奇保健食品有限公司 | 蓝莓酒渣中花青素分离、纯化及检验方法 |
| CN102875514B (zh) * | 2012-09-25 | 2014-12-17 | 凯里学院 | 从蓝莓红叶中提取纯化花青素的方法 |
| JP5981676B2 (ja) * | 2013-03-15 | 2016-08-31 | マース インコーポレーテッドＭａｒｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | 天然の青色アントシアニンを含有する着色料 |
| RU2629257C2 (ru) * | 2013-03-15 | 2017-08-28 | Марс, Инкорпорейтед | Способ выделения фракций синих антоцианинов |
| CN103435589A (zh) * | 2013-09-17 | 2013-12-11 | 北京林业大学 | 一种提高蓝莓花青素稳定性的处理方法 |
| CN104592326A (zh) * | 2015-01-30 | 2015-05-06 | 南开大学 | 采用吸附树脂法从越橘粗提物制备高纯度花色苷的方法 |
| WO2017004452A1 (fr) | 2015-06-30 | 2017-01-05 | Mars, Incorporated | Composition de colorant à base d'anthocyanine acylée et procédés d'utilisation associés |
| CN105153253B (zh) * | 2015-08-31 | 2018-07-20 | 桂林茗兴生物科技有限公司 | 紫甘薯花色苷的提取工艺 |
| CN105061530B (zh) * | 2015-08-31 | 2018-07-20 | 桂林茗兴生物科技有限公司 | 杨梅花色苷的提取工艺 |
| CN105175463B (zh) * | 2015-08-31 | 2018-07-17 | 桂林茗兴生物科技有限公司 | 蓝莓花色苷的提取工艺 |
| CN107973826B (zh) * | 2017-12-07 | 2021-07-16 | 河南省林业科学研究院 | 一种采用混合吸附树脂分离纯化植物叶片花色素苷的方法 |
| DE102020214647A1 (de) * | 2020-11-20 | 2022-05-25 | DIL Deutsches Institut für Lebensmitteltechnik e.V. | Anthocyanhaltiges Extraktpulver und Verfahren zur Herstellung |
| CN114380875B (zh) * | 2021-07-31 | 2023-12-12 | 暨南大学 | 一种植物花色苷的提取分离方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3963700A (en) * | 1974-07-01 | 1976-06-15 | University Patents, Inc. | Recovery of anthocyanin from plant sources |
| US4500556A (en) * | 1982-03-31 | 1985-02-19 | General Foods Corporation | Anthocyanin colorant from grape pomace |
| US4452822A (en) * | 1982-05-17 | 1984-06-05 | United Vintners, Inc. | Extraction and intensification of anthocyanins from grape pomace and other material |
| AU4437399A (en) * | 1998-06-12 | 1999-12-30 | Waters Investments Limited | Novel ion exchange porous resins for solid phase extraction and chromatography |
| US6180154B1 (en) * | 1999-04-28 | 2001-01-30 | The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon State University | Natural colorant from potato extract |
-
2009
- 2009-02-05 CA CA2714084A patent/CA2714084C/fr not_active Expired - Fee Related
- 2009-02-05 WO PCT/US2009/033127 patent/WO2009100165A2/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009100165A2 (fr) | 2009-08-13 |
| CA2714084A1 (fr) | 2009-08-13 |
| WO2009100165A3 (fr) | 2009-12-30 |
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