CN105813471A - 用于蓝色的稳定化的藻蓝蛋白 - Google Patents
用于蓝色的稳定化的藻蓝蛋白 Download PDFInfo
- Publication number
- CN105813471A CN105813471A CN201480067572.XA CN201480067572A CN105813471A CN 105813471 A CN105813471 A CN 105813471A CN 201480067572 A CN201480067572 A CN 201480067572A CN 105813471 A CN105813471 A CN 105813471A
- Authority
- CN
- China
- Prior art keywords
- complex
- phycocyanin
- polyphenol
- phycocyanobilin
- acid
- 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.)
- Pending
Links
- 108010053210 Phycocyanin Proteins 0.000 title claims abstract description 55
- 150000008442 polyphenolic compounds Chemical class 0.000 claims abstract description 26
- 235000013824 polyphenols Nutrition 0.000 claims abstract description 26
- NNMALANKTSRILL-ZUTFDUMMSA-N 3-[(2z,5z)-2-[[3-(2-carboxyethyl)-5-[(z)-[(3z,4r)-3-ethylidene-4-methyl-5-oxopyrrolidin-2-ylidene]methyl]-4-methyl-1h-pyrrol-2-yl]methylidene]-5-[(4-ethyl-3-methyl-5-oxopyrrol-2-yl)methylidene]-4-methylpyrrol-3-yl]propanoic acid Chemical compound O=C1C(CC)=C(C)C(\C=C/2C(=C(CCC(O)=O)C(=C/C3=C(C(C)=C(\C=C/4\C(\[C@@H](C)C(=O)N\4)=C/C)N3)CCC(O)=O)/N\2)C)=N1 NNMALANKTSRILL-ZUTFDUMMSA-N 0.000 claims abstract description 24
- INPDFIMLLXXDOQ-UHFFFAOYSA-N Phycocyanobilin Natural products CCC1=C(C)C(=CC2=NC(=C/c3[nH]c(C=C/4C(C(C(N4)=O)C)=CC)c(C)c3CCC(=O)O)C(=C2C)CCC(=O)O)NC1=O INPDFIMLLXXDOQ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 108010072011 phycocyanobilin Proteins 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 19
- 235000013305 food Nutrition 0.000 claims abstract description 10
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 108090000623 proteins and genes Proteins 0.000 claims description 14
- 102000004169 proteins and genes Human genes 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 239000012634 fragment Substances 0.000 claims description 7
- 239000003086 colorant Substances 0.000 claims description 6
- 238000005520 cutting process Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 102000035195 Peptidases Human genes 0.000 claims description 3
- 108091005804 Peptidases Proteins 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000001261 hydroxy acids Chemical group 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 2
- 230000002255 enzymatic effect Effects 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 229940127557 pharmaceutical product Drugs 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract 1
- 238000003860 storage Methods 0.000 description 22
- 239000000843 powder Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 235000013361 beverage Nutrition 0.000 description 16
- 235000018102 proteins Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 9
- 239000001263 FEMA 3042 Substances 0.000 description 9
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 9
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 9
- 229920002258 tannic acid Polymers 0.000 description 9
- 235000015523 tannic acid Nutrition 0.000 description 9
- 229940033123 tannic acid Drugs 0.000 description 9
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 8
- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 description 6
- 240000002900 Arthrospira platensis Species 0.000 description 4
- 235000016425 Arthrospira platensis Nutrition 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- COVFEVWNJUOYRL-UHFFFAOYSA-N digallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)=C1 COVFEVWNJUOYRL-UHFFFAOYSA-N 0.000 description 4
- 235000004515 gallic acid Nutrition 0.000 description 4
- 229940074391 gallic acid Drugs 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 229940082787 spirulina Drugs 0.000 description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- ZZAFFYPNLYCDEP-HNNXBMFYSA-N Rosmarinsaeure Natural products OC(=O)[C@H](Cc1cccc(O)c1O)OC(=O)C=Cc2ccc(O)c(O)c2 ZZAFFYPNLYCDEP-HNNXBMFYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- -1 elladitannin Chemical compound 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- DOUMFZQKYFQNTF-MRXNPFEDSA-N rosemarinic acid Natural products C([C@H](C(=O)O)OC(=O)C=CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-MRXNPFEDSA-N 0.000 description 3
- TVHVQJFBWRLYOD-UHFFFAOYSA-N rosmarinic acid Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=Cc2ccc(O)c(O)c2)C=O TVHVQJFBWRLYOD-UHFFFAOYSA-N 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- 229920001757 Castalin Polymers 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 229920002707 Digallic acid Polymers 0.000 description 2
- 102000004407 Lactalbumin Human genes 0.000 description 2
- 108090000942 Lactalbumin Proteins 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 108010039918 Polylysine 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
- 229920000171 Quercitannic acid Polymers 0.000 description 2
- 108010073771 Soybean Proteins Proteins 0.000 description 2
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 2
- 241001593750 Turcica Species 0.000 description 2
- SCGCYQONNCQISP-UHFFFAOYSA-N Vescalin Natural products OCC1OC(=O)c2cc(O)c(O)c(O)c2c3c(O)c(O)c(O)cc3C(=O)OC(C1O)C4OC(=O)c5cc(O)c(O)c(O)c5C4O SCGCYQONNCQISP-UHFFFAOYSA-N 0.000 description 2
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 2
- 235000021120 animal protein Nutrition 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 235000021466 carotenoid Nutrition 0.000 description 2
- 150000001747 carotenoids Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229950001002 cianidanol Drugs 0.000 description 2
- 229920002770 condensed tannin Polymers 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 235000003248 hydroxytyrosol Nutrition 0.000 description 2
- 229940095066 hydroxytyrosol Drugs 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000009928 pasteurization Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000656 polylysine Polymers 0.000 description 2
- 235000011962 puddings Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000000582 semen Anatomy 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
- 229960005055 sodium ascorbate Drugs 0.000 description 2
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 2
- 235000019710 soybean protein Nutrition 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 235000003724 spirulina extract Nutrition 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 description 1
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 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
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 description 1
- 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 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XCMSBKKPHWFVIB-UHFFFAOYSA-N 3-phenylpropaneperoxoic acid Chemical compound OOC(=O)CCC1=CC=CC=C1 XCMSBKKPHWFVIB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000256844 Apis mellifera Species 0.000 description 1
- 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 1
- 229920001865 Castalagin Polymers 0.000 description 1
- PPUHUWSVCUJGTD-UTSKMKSGSA-N Castalin Natural products O=C1O[C@H]2[C@H](O)c3c(O)c(O)c(O)c(-c4c(O)c(O)c(O)c5-c6c(O)c(O)c(O)cc6C(=O)O[C@@H](CO)[C@@H](O)[C@H]2OC(=O)c45)c13 PPUHUWSVCUJGTD-UTSKMKSGSA-N 0.000 description 1
- CHBITXAMNKHJCR-WWPZCJLISA-N Casuariin Natural products O=C1O[C@@H]2[C@@H]([C@@H]3[C@@H](O)COC(=O)c4c(c(O)c(O)c(O)c4)-c4c(O)c(O)c(O)cc4C(=O)O3)OC(=O)c3c(c(O)c(O)c(O)c3)-c3c(O)c(O)c(O)c([C@@H]2O)c13 CHBITXAMNKHJCR-WWPZCJLISA-N 0.000 description 1
- YDDGKXBLOXEEMN-IABMMNSOSA-L Chicoric acid Natural products C1=C(O)C(O)=CC=C1\C=C\C(=O)O[C@@H](C([O-])=O)[C@H](C([O-])=O)OC(=O)\C=C\C1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-IABMMNSOSA-L 0.000 description 1
- 241000192700 Cyanobacteria Species 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- YDDGKXBLOXEEMN-UHFFFAOYSA-N Di-E-caffeoyl-meso-tartaric acid Natural products C=1C=C(O)C(O)=CC=1C=CC(=O)OC(C(O)=O)C(C(=O)O)OC(=O)C=CC1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 229920001958 Grandinin Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 108010085220 Multiprotein Complexes Proteins 0.000 description 1
- 102000007474 Multiprotein Complexes Human genes 0.000 description 1
- 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 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- IYMHVUYNBVWXKH-ZITZVVOASA-N Pedunculagin Chemical compound C([C@H]1OC2O)OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]1[C@H]1[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(O)C=C2C(=O)O1 IYMHVUYNBVWXKH-ZITZVVOASA-N 0.000 description 1
- 229920000158 Pedunculagin Polymers 0.000 description 1
- HVXQPVRDPFKKHP-UHFFFAOYSA-N Pedunculagin Natural products OC1C2COC(=O)c3cc(O)c(O)c(O)c3c4c(O)c(O)c(O)cc4C(=O)OC(O2)C5OC(=O)c6cc(O)c(O)c(O)c6c7c(O)c(O)c(O)cc7C(=O)OC15 HVXQPVRDPFKKHP-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 108010004729 Phycoerythrin Proteins 0.000 description 1
- 229920000241 Punicalagin Polymers 0.000 description 1
- 229920000864 Punicalin Polymers 0.000 description 1
- 241000220324 Pyrus Species 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
- 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
- 244000295490 Salvia japonica Species 0.000 description 1
- 235000005794 Salvia japonica Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 108010004469 allophycocyanin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 239000000038 blue colorant Substances 0.000 description 1
- 229940074360 caffeic acid Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- UDYKDZHZAKSYCO-CIBWSTISSA-N castalagin Chemical compound C([C@H]1OC(=O)C2=CC(O)=C(O)C(O)=C2C=2C(O)=C(O)C(O)=C(C=2C(=O)O2)C3=C(O)C(O)=C4O)OC(=O)C5=CC(O)=C(O)C(O)=C5C5=C(O)C(O)=C(O)C=C5C(=O)O[C@H]1[C@H]2[C@@H]1[C@@H](O)C4=C3C(=O)O1 UDYKDZHZAKSYCO-CIBWSTISSA-N 0.000 description 1
- FTFKAWWJGCCSJT-UHFFFAOYSA-N castalagin Natural products OC1OC2C(O)c3c(O)c(O)c(O)c(c13)c4c(O)c(O)c(O)c5c4C(=O)OC2C6OC(=O)c7cc(O)c(O)c(O)c7c8c(O)c(O)c(O)cc8C(=O)OCC6OC(=O)c9cc(O)c(O)c(O)c59 FTFKAWWJGCCSJT-UHFFFAOYSA-N 0.000 description 1
- PPUHUWSVCUJGTD-UHFFFAOYSA-N castalin Chemical compound OC1C(CO)OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(O)C(C3=C(O)C(O)=C4O)=C2C(=O)OC1C1C(O)C4=C3C(=O)O1 PPUHUWSVCUJGTD-UHFFFAOYSA-N 0.000 description 1
- CHBITXAMNKHJCR-JNUHSSLSSA-N casuariin Chemical compound O1C(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(O)C=C2C(=O)OC[C@@H](O)[C@@H]1[C@@H]1OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(O)C3=C2C(=O)O[C@H]1[C@@H]3O CHBITXAMNKHJCR-JNUHSSLSSA-N 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- ZVFDKYBWZMATCT-MVLAPQGRSA-N chembl506427 Chemical compound O[C@@H]1[C@H](O)[C@@H](O)COC1(O)[C@H]1C(C(O)=C(O)C(O)=C2C3=C(O)C(O)=C4O)=C2C(=O)O[C@@H]1[C@@H]1[C@@H]2OC(=O)C5=CC(O)=C(O)C(O)=C5C5=C(O)C(O)=C(O)C=C5C(=O)OC[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2C4=C3C(=O)O1 ZVFDKYBWZMATCT-MVLAPQGRSA-N 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- YDDGKXBLOXEEMN-IABMMNSOSA-N chicoric acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-IABMMNSOSA-N 0.000 description 1
- 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 1
- 235000001368 chlorogenic acid Nutrition 0.000 description 1
- 229940074393 chlorogenic acid Drugs 0.000 description 1
- 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 1
- 229930016920 cichoric acid Natural products 0.000 description 1
- 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 1
- 238000005352 clarification Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- YDDGKXBLOXEEMN-PMACEKPBSA-N dicaffeoyl-D-tartaric acid Natural products O([C@H](C(=O)O)[C@H](OC(=O)C=CC=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)C=CC1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-PMACEKPBSA-N 0.000 description 1
- YDDGKXBLOXEEMN-WOJBJXKFSA-N dicaffeoyl-L-tartaric acid Natural products O([C@@H](C(=O)O)[C@@H](OC(=O)C=CC=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)C=CC1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-WOJBJXKFSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 1
- 235000012734 epicatechin Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect 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
- QOLIPNRNLBQTAU-UHFFFAOYSA-N flavan Chemical compound C1CC2=CC=CC=C2OC1C1=CC=CC=C1 QOLIPNRNLBQTAU-UHFFFAOYSA-N 0.000 description 1
- 235000002864 food coloring agent Nutrition 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 1
- 235000003969 glutathione Nutrition 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 229940127081 grandinin Drugs 0.000 description 1
- IHBQFOUFVYPLPE-UHFFFAOYSA-N grandinin Natural products OCC(O)C(O)C(O)C(=O)C1C2OC(O)c3c1c(O)c(O)c(O)c3c4c(O)c(O)c(O)c5c4C(=O)OC2C6OC(=O)c7cc(O)c(O)c(O)c7c8c(O)c(O)c(O)cc8C(=O)OCC6OC(=O)c9cc(O)c(O)c(O)c59 IHBQFOUFVYPLPE-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229930005346 hydroxycinnamic acid Natural products 0.000 description 1
- 235000010359 hydroxycinnamic acids Nutrition 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 235000019136 lipoic acid Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- IYMHVUYNBVWXKH-UHFFFAOYSA-N pedunculagin I isomer Natural products OC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C2C1OC(=O)C1=CC(O)=C(O)C(O)=C1C1=C(O)C(O)=C(O)C=C1C(=O)O2 IYMHVUYNBVWXKH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000006916 protein interaction Effects 0.000 description 1
- IQHIEHIKNWLKFB-ITTSEVFZSA-N pumcalin Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C11)O)O)OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(OC3=O)C4=C2C(=O)OC2=C4C3=C1C(O)=C2O IQHIEHIKNWLKFB-ITTSEVFZSA-N 0.000 description 1
- ZJVUMAFASBFUBG-OGJBWQGYSA-N punicalagin Chemical compound C([C@H]1O[C@@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]2[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C11)O)OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(OC3=O)C4=C2C(=O)OC2=C4C3=C1C(O)=C2O ZJVUMAFASBFUBG-OGJBWQGYSA-N 0.000 description 1
- LMIBIMUSUFYFJN-RSVYENFWSA-N punicalagin Natural products O[C@@H]1O[C@@H]2COC(=O)c3cc(O)c(O)c(O)c3c4c(O)cc5OC(=O)c6c(c(O)c(O)c7OC(=O)c4c5c67)c8c(O)c(O)c(O)cc8C(=O)O[C@H]2[C@@H]9OC(=O)c%10cc(O)c(O)c(O)c%10c%11c(O)c(O)c(O)cc%11C(=O)O[C@@H]19 LMIBIMUSUFYFJN-RSVYENFWSA-N 0.000 description 1
- ZRKSVMFLACVUIU-UHFFFAOYSA-N punicalagin isomer Natural products OC1=C(O)C(=C2C3=4)OC(=O)C=4C4=C(O)C(O)=C3OC(=O)C2=C1C1=C(O)C(O)=C(O)C=C1C(=O)OC1C2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(O)OC1COC(=O)C1=CC4=C(O)C(O)=C1O ZRKSVMFLACVUIU-UHFFFAOYSA-N 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 238000004062 sedimentation 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
- 235000011888 snacks Nutrition 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 235000015149 toffees Nutrition 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- NGSWKAQJJWESNS-ZZXKWVIFSA-N trans-4-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-N 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
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/179—Colouring agents, e.g. pigmenting or dyeing agents
-
- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/58—Colouring agents
-
- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/46—Addition of dyes or pigments, e.g. in combination with optical brighteners using dyes or pigments of microbial or algal origin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/645—Proteins of vegetable origin; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/195—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Inorganic Chemistry (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Non-Alcoholic Beverages (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
Abstract
本发明涉及基于稳定化的藻蓝蛋白的可用于制备食品、饲料、化妆品和药品和药物制剂的蓝色着色组合物,其为至少一种藻蓝胆素和至少一种多酚的络合物;以及形成该络合物的方法。
Description
本发明涉及用于制造基于稳定化藻蓝蛋白的食品、饲料、化妆品和药学产品和制剂的蓝色发光组合物,所述稳定化藻蓝蛋白是至少一种藻蓝胆素和至少一种多酚的复合体,以及用于形成该复合体的方法。
藻蓝蛋白是具有特征性浅蓝色的色素蛋白质复合体,吸收接近620nm的橙色光和红色光。藻蓝蛋白发现于蓝细菌中,先前被称为蓝绿藻。色素(分别是藻蓝蛋白的发色团)是藻蓝胆素。该发色团是通过硫醚键共价结合蛋白质的四吡咯。除了硫醚键,发色团通过氢键键合与蛋白质相互作用,其导致发色团的有利构象。这产生深蓝色。藻蓝胆素也可以发现于别藻蓝蛋白、藻红蛋白和其他色素蛋白质中。
藻蓝蛋白通常分离自螺旋藻(Spirulina)藻类并显示许多膳食和治疗属性。因此,螺旋藻和螺旋藻提取物已长期用作食品或营养组分。制备此类组分的一种方法公开于WO03/080811A1,其描述了通过加热至70-100℃而将色蛋白变性来解决由于深蓝色引起的令人讨厌的外观的办法。因此,藻蓝蛋白对于环境中温度和pH变化非常敏感,这是由于其多肽亚基。(Seo等,Int.J.Mol.Sci.2013,14,1778-1787)。另一方面,蛋白质-发色团相互作用的任何改变导致颜色丧失。
此外,在食品,尤其是饮料中使用螺旋藻提取物或藻蓝蛋白也是已知的(例如CN103054117A),仍存在对满足由FDA或欧洲共同体所要求的高安全性标准的食品、饲料、化妆品或药物制剂中无毒、无害的蓝色着色剂的需求。此外,蓝色必须经长时期以及低、酸性pH以及约60-130°C的高温而保持稳定,因为例如用于巴氏杀菌方法中。
发色团必须进一步对氧化(其也减少颜色)稳定。
颜色例如着色剂(颜色化合物)必须在室温在高光照条件下尤其是稳定的。此外,必须避免着色剂组合物(尤其在饮料中)的沉淀,因为这将导致增加的浊度和沉降。
因此,依赖于特定的蛋白质结构产生正确颜色的颜色化合物的稳定是非常困难的。
此外,颜色化合物,尤其是发色团与另一化合物的络合物(其颜色基于发色团与这一其他化合物的相互作用)必须对于与其他分子的反应或相互作用是惰性的,所述反应或相互作用可能导致最终制剂诸如食物、饲料、化妆品和药物的颜色丧失。
因此,已发现可通过在水溶液中将多酚与包含至少一种藻蓝胆素的组合物混合而获得的至少一种藻蓝胆素和至少一种多酚的络合物满足所有需求。
在一个实施方案中,通过在水溶液中将多酚与包含至少一种藻蓝胆素的组合物混合而获得至少一种藻蓝胆素和至少一种多酚的络合物。
在本发明的一个实施方案中,包含至少一种藻蓝胆素的组合物包含由至少一种藻蓝胆素和至少一种氨基酸组成的藻蓝蛋白片段。氨基酸可以通过氢键键合和/或通过硫醚键与发色团相互作用。化合物可以包含其他氨基酸,其通过氢键键合与藻蓝胆素相互作用。
在一个备选方案中,该络合物是稳定的络合物。
“稳定的”意指,由于高热力学和/或动力学稳定性,络合物具有低的、优选非常低的解离常数,从而使化学平衡移向络合物一侧。因此,络合物在水中可溶但不会解离。
在一个实施方案中,络合物在pH1-8下,优选1.5-7、pH2-5,更优选2.5-4、pH3-4,尤其是pH3.5下是稳定的。
“稳定的”意指络合物维持蓝色,优选纯蓝色或蓝紫色,具有波长在550-670nm,优选560-640nm,更优选580-620nm,尤其是600-610nm区间内的最大光吸收。
在一个备选方案中,还存在可能在任何上述范围内的两个峰(peek)。
在其他实施方案中,本发明的络合物显示波长在550-670nm,优选560-640nm,更优选580-620nm,尤其是590-610nm区间内的增加的光吸收。
波长在上述区间内的增加的光吸收比藻蓝蛋白的吸光度高5%-200%,优选5%-95%,10%-90%、20%-90%、25%-90%,更优选25%-80%。
藻蓝蛋白与多酚的比率为1:10-10:1,优选1:2-5:1,更优选1:1-2:1,尤其是1:1。
在一个实施方案中,包含至少一种藻蓝胆素的组合物可以通过切割藻蓝蛋白获得或者通过切割藻蓝蛋白获得。
从螺旋藻藻类分离藻蓝蛋白是本领域所熟知的且可以例如根据由以下公开的方法来进行:Seo等(Int.J.Mol.Sci.2013,14,1778-1787)、Muthulakshni等(J.AlgaBiomusUtln.2012,3,7-11)、Hemlata等(J.AlgaBiomusUtln.2011,2,(1),30–51)或Gantar等(J.Biotechnol.2012,159(1-2),21–26)。此外,可以使用市售藻蓝蛋白,例如来自DIC的称为LinablueG1的商业粉末。
在一个实施方案中,本发明的多酚选自包含至少两个酚环的化合物,所述苯环的每一个被至少两个羟基,优选三个羟基所取代,和/或所述多酚包含至少一个羧酸酯基团和/或羧酸基团。
根据本发明,术语“羧酸基团”还涵盖羧基。
在一个备选方案中,本发明的多酚包含没食子酸的酯或聚合物。
多酚化合物还可以包含具有至少两个羟基线性饱和或不饱和烷基,优选具有羧基的C2或C3烷基的酚环。在多酚中,该羧基用于酯类键合或是游离的羧酸或羧基。
多酚还可以包含具有C5或C6的碳链的环烷基或异环烷基。优选使用葡萄糖或其他糖。
在一个实施方案中,本发明的多酚选自迷迭香酸、鞣酸、双没食子酸、缩合鞣质(黄烷的缩合产物)、栎单宁酸、没食子单宁酸、栎精、鞣花单宁、栗木鞣花素、栗木素、casuariticin、grandinin、punicaligin、石榴皮鞣素、roburinA、特里马素II、terflavinB、vescaligin、赤芍素、casuariin、castlin、栎木素,优选迷迭香酸、鞣酸、双没食子酸、缩合鞣质、栎单宁酸、没食子单宁酸、鞣花单宁,更优选鞣酸(CAS1401-55-4)。
本发明的其他主题是至少一种藻蓝胆素和至少一种多酚的络合物,所述络合物可通过在水溶液中将多酚与包含至少一种藻蓝胆素的组合物混合获得,所述水溶液包含具有比藻蓝蛋白更高的等电点的蛋白质。
具有更高等电点的蛋白质在水溶液中是高度可溶的,优选具有pH1-7,优选1.5-7、pH2-5,更优选2.5-4、pH3-4,尤其pH3.5的酸性水溶液;更优选在饮料中。
在一个备选方案中,具有更高等电点的蛋白质选自动物蛋白质、植物蛋白质、来自微生物的蛋白质,优选选自乳清蛋白分离物、大豆蛋白质、聚赖氨酸。
在其他备选方案中,蛋白质具有4-9的等电点。
在本发明的一个备选方案中,使用水可溶聚合物替代具有更高等电点的蛋白质。
本发明的其他目标是用于形成络合物的方法,其包括在水溶液中将多酚与包含至少一种藻蓝胆素的组合物混合的步骤。
在一个实施方案中,包含至少一种藻蓝胆素的组合物通过用化学和/或酶促切割来切割藻蓝蛋白而获得。
在一个备选方案中,藻蓝蛋白通过蛋白水解切割。
蛋白水解可以通过施加至少一种强酸和任选热来进行。
具有pKa为-1及以下的强酸可以例如为HCl、甲酸、H2SO4、HNO3或其混合物,优选HCL。
任选地,将强酸和藻蓝蛋白的混合物加热至20-100℃的温度。任选地,酸可以是离子交换树脂的形式。
在一个实施方案中,将藻蓝蛋白粉末添加至浓强酸,优选HCL中,并搅拌。
藻蓝蛋白的切割产生藻蓝蛋白片段。一些片段包含藻蓝胆素。
切割反应通过用水稀释而终止。该步骤还导致藻蓝蛋白片段的沉淀。
在一个备选方案中,加入多酚以更好地沉淀。
将溶液过滤以去除强酸,产生藻蓝蛋白片段滤饼。随后将滤饼溶解于纯水中并搅拌或混合直至藻蓝蛋白片段溶解。将溶液喷雾干燥,产生在水中具有良好的可溶性的细粉。
本发明的络合物通过在水溶液中将多酚与包含至少一种藻蓝胆素的组合物混合而形成。
在其他实施方案中,将额外的蛋白质加入到本发明的络合物中,由此该额外蛋白质具有高于藻蓝蛋白的等电点。
本发明的主题还是至少一种藻蓝胆素和至少一种多酚和额外蛋白质(优选具有更高的等电点)或聚合物的络合物。本发明的第二络合物在具有非常接近藻蓝蛋白的等电点的pH(优选pH3-4)的溶液中是稳定的。
具有更高等电点的蛋白质选自动物蛋白质、植物蛋白质,优选选自乳清蛋白分离物、大豆蛋白质、聚赖氨酸。
本发明的络合物以及本发明的第二络合物可用作着色剂。
本发明的其他主题是本发明的络合物以及第二络合物在食物、饲料、化妆品或药物制剂中的用途。
本发明的主题还是根据任何上述方法产生的任何产品。
本发明的其他主题还是上述络合物的络合物作为着色剂的用途。
本发明的额外的主题是包含本发明的络合物或本发明的第二络合物(优选作为着色剂)的本发明的产品,即食物、饲料、化妆品和药物制剂。
在一个实施方案中,食品选自饮料、饮料像软饮料、调味水、果汁、鸡尾酒(punches)或这些饮料的浓缩形式以及酒精饮品和速溶饮料粉、冰激凌、蛋糕、硬糖、奶酪、乳制品像乳饮料或酸奶、豆奶等、糖果产品、口香糖、甜品、奶糖、布丁、果冻、速溶布丁粉、以及小吃、饼干、调味酱、谷类食品、沙拉酱、汤。
在一个实施方案中,化妆品制剂选自面霜、牙膏、化妆品、皮肤产品(dermalproducts)。
在一个实施方案中,药物制剂选自软膏、丸剂、片剂、胶囊。
令人惊奇的且本领域技术人员无法预想到的是,本发明的目标可以通过本发明的络合物、方法或其他主题而得到解决。尤其令人惊奇的是,本发明的络合物在巴氏消毒法过程中(尤其是在90℃持续15分钟)且另外在贮存过程中在强光暴露下(如饮料在货架上储存长达6个月过程中可见的)在水溶液中是稳定的。
进一步令人惊奇的是本发明的络合物在低pH下,优选1-8,优选1.5-7、pH2-5,更优选2.5-4、pH3-4,尤其是pH3.5下是稳定的。
此外,本发明的络合物和尤其是本发明的第二络合物显示在水性组合物尤其是饮料中无沉淀和无浊度增加。
作为着色剂,优选在食品,尤其在饮料中,本发明的络合物和本发明的第二络合物分别以以下的量使用:1-5000ppm,优选10-700ppm,更优选10-500ppm,尤其是50-400ppm。
本发明的饮料可以额外包含:
在一个实施方案中,饮料是澄清的或混浊的,具有1-5000的NTU。
在一个实施方案中,产品的颜色可以通过加入类胡萝卜素或任何其他黄色食品色从蓝色改变为绿色。因此,本发明的产品包含类胡萝卜素,任选熔化的和/或溶解于以下和/或从反式异构化为顺式的:三酰甘油,诸如MCT油(中链三酰甘油)、橄榄油、玉米油、葵花油、花生油、大豆油或其他备选的植物油,优选MCT油。
在一个实施方案中,饮料产品包含油可溶性抗氧化剂。
在其他实施方案中,产品包含选自以下的碳水化合物:单糖、二糖或寡糖,葡萄糖浆、麦芽糖和海藻糖,优选葡萄糖浆、麦芽糖和海藻糖。糖类包括葡萄糖、果糖、半乳糖或甘露糖。
本发明的产品在一个备选方案中包含选自以下的至少一种水溶性抗氧化剂:
-天然化合物,其作为抗氧化剂是有活性的,因为它们在其化学结构中包含酚类OH基团:如肉桂酸的羟基衍生物,例如羟基肉桂酸、羟基肉桂酸酯(盐),其为一类具有C6-C3骨架的多酚,例如羟基氢化肉桂酸酯(盐);
-咖啡酸、阿魏酸、酪醇、羟基酪醇、肉桂酸、绿原酸、香豆素、香豆酸、芥子酸、肉桂酸、菊苣酸,和具有C1-C20的任何这些化合物的酯类;
-富含以上化合物的至少一种的植物提取物;
-迷迭香酸、羟基酪醇;
-常见香料的提取物。在一个实施方案中,常见香料选自迷迭香、香蜂叶、牛至、百里香、薄荷、鼠尾草或包含或富含上述化合物的至少一种的类似植物;
-味元素(flavons),其为一类天然化合物,其中存在超过5000种用作抗氧化剂,它们中的任何可以提取自植物诸如茶叶或包含或富含儿茶酸或表儿茶酸或衍生物的任何其他植物,由此这些化合物可以被碳水化合物糖基化或被脂肪酸C1-C20或没食子酸酯化;来自包含或富含一种或多种上述化合物的植物诸如茶叶、橄榄、梨、苹果的提取物;
-抗坏血酸钠、多酚、Teanova80、谷胱甘肽、硫辛酸、儿茶酸、punicalagin、呫吨酮、苯并环庚三烯酚酮(benzotropolones),优选抗坏血酸钠。
实施例:
实施例1:经切割的藻蓝蛋白粉末的形成。
将18g藻蓝蛋白(来自DIC的称为LinablueG1的商购粉末)加入60g浓HCl中。将该溶液搅拌2小时。这产生蛋白质的部分降解。2小时后,通过将HCl/藻蓝蛋白溶液倒入533g水中终止反应。用水稀释导致藻蓝蛋白沉淀,允许过滤或离心以将经切割的藻蓝蛋白分离出来。随后将经切割的藻蓝蛋白在水中用球磨再分散。随后将经切割的藻蓝蛋白溶液通过喷雾干燥进行干燥,产生水溶性粉末。
实施例2:储存稳定性
将样品以500ppm浓度储存于室温(22℃)下的密封玻璃瓶中。将瓶置于距光源直线距离(straightrow)30cm处,因此将所有样品暴露于相同量的光7000LUX。随后通过在分光计(UV-vis光谱学HP8452A)在最大吸收下测量吸光度来测量颜色强度。进行该测试来模拟饮料直接在超市货架光源下的储存;然而,光强度实质上高于超市货架从而以加速方式评价对光的颜色稳定性。在该测试中储存7天后粗略地等同于在常规储存光照下储存3个月。
颜色损失的所有计算均基于试验开始(第0天)至研究结束中最终混合物的吸收,使用以下公式:
((Abs开始-Abs结束)/Abs开始)*100
其中Abs表示在测量最大吸光度的波长处所选的吸收。将样品在500ppm水溶液中直接测量。
实施例3:
将未切割的藻蓝蛋白(来自DIC的称为LinablueG1的商购粉末)粉末以pH2和500ppm浓度溶解于水中,随后将瓶密封并置于加速储存中5天。储存周期后,测量吸收。
该样品损失100%的其颜色强度。
实施例4:
将经切割的藻蓝蛋白(参见实施例1)(来自DIC的称为LinablueG1的商购粉末)以pH2和500ppm浓度溶解于水中,随后将瓶密封并置于加速储存中5天。储存周期后,测量吸收。
该样品损失100%的其颜色强度(参见图1)。
实施例5:
将未切割的藻蓝蛋白粉末(来自DIC的称为LinablueG1的商购粉末)以pH3.5和500ppm浓度溶解于水中,随后将瓶密封并置于加速储存中5天。储存周期后,测量吸收。
该样品损失100%的其颜色强度,此外,可见显著聚集。
实施例6:
将经切割的藻蓝蛋白(参见实施例1)(来自DIC的称为LinablueG1的商购粉末)以pH3.5和500ppm浓度溶解于水中,随后将瓶密封并置于加速储存中5天。储存周期后,测量吸收。
该样品损失100%的其颜色强度,无聚集可见。
实施例7:
将未切割的藻蓝蛋白粉末(来自DIC的称为LinablueG1的商购粉末)以pH2和500ppm浓度溶解于水中,随后将100ppm的单宁酸加入溶液中,从而形成络合物。
络合物形成通过溶液吸收的小幅度增加来表明(6.4%的吸收增加和吸收最大值从628nm至632nm的偏移)。
最后,将瓶密封并置于加速储存中5天。储存周期后,测量吸收。
该样品损失64%的其颜色强度。
实施例8:
将经切割的藻蓝蛋白(参见实施例1)(来自DIC的称为LinablueG1的商购粉末)以pH2和500ppm浓度溶解于水中,随后将100ppm的单宁酸加入溶液中,从而形成络合物。
络合物形成通过溶液吸收的增加来表明(18%的吸收增加和吸收最大值从598nm至604nm的偏移)。最后,将瓶随后密封并置于加速储存中5天。储存周期后,测量吸收。
该样品损失35%的其颜色强度。
实施例9:
将经切割的藻蓝蛋白(参见实施例1)(来自DIC的称为LinablueG1的商购粉末)以pH2和500ppm浓度溶解于水中,随后将500ppm的没食子酸加入溶液中,然而,没有测量到吸收的增加。最后,将瓶随后密封并置于加速储存中5天。储存周期后,测量吸收。
该样品损失100%的其颜色强度。
实施例10:
将经切割的藻蓝蛋白(参见实施例1)(来自DIC的称为LinablueG1的商购粉末)以pH2和500ppm浓度溶解于水中,随后将500ppm的迷迭香酸加入溶液中,从而形成络合物。
络合物形成通过溶液吸收的小幅度增加来表明(11%的吸收增加和吸收最大值从598nm至608nm的偏移)。最后,将瓶随后密封并置于加速储存中5天。储存周期后,测量吸收。
该样品损失35%的其颜色强度。
实施例11:
将经切割的藻蓝蛋白(参见实施例1)(来自DIC的称为LinablueG1的商购粉末)以pH3.5(3.5为饮料中的常见pH)和500ppm浓度溶解于水中,随后将100ppm的单宁酸加入溶液中,从而形成络合物。
络合物形成通过溶液吸收的显著增加来表明(84%的吸收增加和吸收最大值从564nm至604nm的偏移)。储存5天后,我们无法测量到任何颜色破坏(参见图1)。
这用目视检查(其中不能检测到任何褪色)来证实。
实施例12:
将经切割的藻蓝蛋白(参见实施例1)(来自DIC的称为LinablueG1的商购粉末)以pH3.5(3.5为饮料中的常见pH)和500ppm浓度溶解于水中,随后将100ppm的单宁酸加入溶液中,从而形成络合物。
络合物形成通过溶液吸收的显著增加来表明(84%的吸收增加和吸收最大值从564nm至604nm的偏移)(图1)。
储存14天后,样品已损失18%的其颜色。
应注意,加速储存14天粗略地相当于饮料可能暴露于超市光照下货架上储存6个月的光量。应进一步注意,即使测量颜色强度比实验开始时低18%,但颜色强度中这种小量的降低通过新鲜样品和储存样品(加速储存14天)之间的目视比较仍是无法注意到的。
本发明的络合物的颜色强度由于多酚-发色团络合物而相比于空白或没食子酸降低较少或者增加。结果概述与表1和图1中。
表1.实施例的概述。
Claims (15)
1.至少一种藻蓝胆素和至少一种多酚的络合物,其可通过在水溶液中将多酚与包含至少一种藻蓝胆素的组合物混合而获得。
2.权利要求1的络合物,其为水中稳定的不解离的络合物。
3.权利要求1的络合物,其在pH1-8下是稳定的。
4.权利要求1的络合物,其相比于纯的藻蓝蛋白,具有在550-670nm区间内波长的增加的光吸收。
5.权利要求1的络合物,其中所述包含至少一种藻蓝胆素的组合物可通过切割藻蓝蛋白而获得。
6.权利要求1的络合物,由此所述多酚选自包含至少两个苯酚环的化合物,所述至少两个苯酚环的每一个被至少一个羟基所取代,和/或所述多酚包含至少一个羧酸酯基团和/或羧酸基团,任选具有C5或C6碳链的环烷基或杂环烷基,优选一个葡萄糖基团。
7.权利要求1的络合物,其包含具有比藻蓝蛋白更高的等电点的蛋白质和/或聚合物。
8.用于形成络合物的方法,其包括在水溶液中将多酚与包含至少一种藻蓝胆素的组合物混合的步骤。
9.权利要求8的方法,其中包含至少一种藻蓝胆素的组合物通过用化学和/或酶促切割来切割藻蓝蛋白而获得。
10.权利要求9的方法,其中藻蓝蛋白通过蛋白水解切割。
11.权利要求10的方法,其中藻蓝蛋白通过至少一种强酸和任选热的作用来切割。
12.权利要求8-10中任一项的方法,其中将藻蓝蛋白片段的溶液喷雾干燥并再溶解于水中。
13.权利要求8-12中任一项的方法,其包括添加具有比藻蓝蛋白更高的等电点的蛋白质的步骤。
14.权利要求1-7中任一项的络合物或根据权利要求8-13中任一项的方法的络合物在食品、饲料、化妆品和药物制剂中的用途。
15.权利要求1-7中任一项的络合物或根据权利要求8-13中任一项的方法的络合物作为着色剂的用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13197910.6 | 2013-12-18 | ||
EP13197910 | 2013-12-18 | ||
PCT/EP2014/073057 WO2015090697A1 (en) | 2013-12-18 | 2014-10-28 | Stabilized phycocyanin for blue color |
Publications (1)
Publication Number | Publication Date |
---|---|
CN105813471A true CN105813471A (zh) | 2016-07-27 |
Family
ID=49841539
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201480067572.XA Pending CN105813471A (zh) | 2013-12-18 | 2014-10-28 | 用于蓝色的稳定化的藻蓝蛋白 |
Country Status (9)
Country | Link |
---|---|
US (1) | US20160324745A1 (zh) |
EP (1) | EP3091852A1 (zh) |
JP (1) | JP2017509316A (zh) |
KR (1) | KR20160098272A (zh) |
CN (1) | CN105813471A (zh) |
AU (1) | AU2014365657A1 (zh) |
MX (1) | MX2016008084A (zh) |
PH (1) | PH12016501093A1 (zh) |
WO (1) | WO2015090697A1 (zh) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106667794A (zh) * | 2017-01-25 | 2017-05-17 | 西安科艺诗生物技术有限公司 | 一种提高色素蛋白光稳定性的包合物及应用 |
CN107047972A (zh) * | 2017-04-24 | 2017-08-18 | 苏州维淼生物工程有限公司 | 一种添加水华蓝藻提取物的功能性饲料 |
CN110753496A (zh) * | 2017-06-15 | 2020-02-04 | 奥伽马公司 | 获得包含微藻和/或蓝细菌提取物的由果汁制成的稳定化食品饮料的方法 |
CN112087954A (zh) * | 2018-12-17 | 2020-12-15 | Dic株式会社 | 色素材料水溶液、色素材料水溶液的制造方法和蓝色着色饮料 |
CN113645855A (zh) * | 2019-05-29 | 2021-11-12 | 科汉森天然色素有限责任公司 | 藻蓝蛋白的稳定 |
WO2022073438A1 (zh) * | 2020-10-09 | 2022-04-14 | 暨南大学 | 一种高负载藻蓝蛋白的纳米颗粒及其制备方法与应用 |
CN115607477A (zh) * | 2022-10-24 | 2023-01-17 | 中国海洋大学 | 维持藻蓝蛋白在酸性条件下热稳定性的方法 |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR112017022523B1 (pt) | 2015-04-23 | 2023-12-19 | Basf Se | Formulação para cápsulas de gel, cápsula de gel, e, processo para produção de uma formulação |
WO2018003599A1 (ja) | 2016-06-28 | 2018-01-04 | Dicライフテック株式会社 | 色素材及び色素材の製造方法 |
EP3570689A1 (en) * | 2017-01-20 | 2019-11-27 | ADM WILD Europe GmbH & Co. KG | Liquid composition comprising phycocyanin |
FR3063875B1 (fr) * | 2017-03-17 | 2021-02-19 | Labeille | Composition liquide comprenant de la phycocyanine |
AU2018238567B2 (en) * | 2017-03-20 | 2023-05-11 | Algalife Ltd. | Composition comprising cultivated microalgae for use in coloring processes |
FR3064635B1 (fr) | 2017-03-30 | 2021-07-23 | Fermentalg | Purification des phycobiliproteines |
US11350651B2 (en) * | 2018-02-27 | 2022-06-07 | Talking Rain Beverage Company, Inc. | Indian gooseberry extract as a natural color stabilizer for beverages |
EP3760184B1 (en) | 2019-07-04 | 2023-02-15 | Calicea | Composition comprising stabilized phycocyanin and its uses |
WO2021121647A1 (en) | 2019-12-18 | 2021-06-24 | Ramirez Rios Liliana Patricia | Metal complexes of macrocycles and/or isoprenoids and/or linear tetrapyrroles by mechanochemistry (grinding or milling), preparation method thereof, sunscreen/concealer/uv absorber thereof, self-assembled coating material thereof, superamphiphilic material or surfaces thereof, hair dyeing thereof and other uses thereof |
WO2021156462A1 (en) | 2020-02-06 | 2021-08-12 | Chr. Hansen Natural Colors A/S | Stable phycocyanin based color formulation |
WO2023052343A1 (en) | 2021-09-28 | 2023-04-06 | Givaudan Sa | Couloring composition |
EP4226772A1 (en) | 2021-11-23 | 2023-08-16 | Givaudan SA | Colouring composition |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5347572A (en) * | 1976-10-08 | 1978-04-28 | Shimizugen Shiyouten Kk | Food coloring method |
CN1119660A (zh) * | 1994-07-21 | 1996-04-03 | 宾-古里安尼格夫大学研究及发展部 | 着色剂 |
WO2005065697A1 (fr) * | 2003-12-12 | 2005-07-21 | Florence Minard | Procede de photo-stabilisation de phycobiliproteines dans un extrait aqueux, compositions contenant des phycobiliproteines stabilisees et utilisation de phycobiliproteines stabilisees |
EP1591099A2 (en) * | 2004-04-28 | 2005-11-02 | MERCK PATENT GmbH | Methods for stabilizing ingredients within cosmetics, personal care and household products |
CN101778572A (zh) * | 2007-08-02 | 2010-07-14 | 荷兰联合利华有限公司 | 包含多酚的组合物 |
CN101891809A (zh) * | 2010-06-18 | 2010-11-24 | 中国科学院海洋研究所 | 一种藻蓝蛋白提取物的制备和应用 |
CN101948887A (zh) * | 2010-08-27 | 2011-01-19 | 中国石油大学(华东) | 一种重组藻蓝胆素的制备方法及其应用 |
CN102140259A (zh) * | 2010-12-22 | 2011-08-03 | 晨光生物科技集团股份有限公司 | 一种红米红色素的稳定化处理方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1888115A2 (en) * | 2005-05-16 | 2008-02-20 | Universite De Geneve | Compounds for photochemotherapy |
FR2994693B1 (fr) * | 2012-08-23 | 2014-08-22 | Oreal | Composition de maquillage comprenant un pigment bleu |
-
2014
- 2014-10-28 MX MX2016008084A patent/MX2016008084A/es unknown
- 2014-10-28 WO PCT/EP2014/073057 patent/WO2015090697A1/en active Application Filing
- 2014-10-28 JP JP2016540560A patent/JP2017509316A/ja active Pending
- 2014-10-28 KR KR1020167016299A patent/KR20160098272A/ko not_active Application Discontinuation
- 2014-10-28 US US15/104,737 patent/US20160324745A1/en not_active Abandoned
- 2014-10-28 AU AU2014365657A patent/AU2014365657A1/en not_active Abandoned
- 2014-10-28 EP EP14795583.5A patent/EP3091852A1/en not_active Withdrawn
- 2014-10-28 CN CN201480067572.XA patent/CN105813471A/zh active Pending
-
2016
- 2016-06-08 PH PH12016501093A patent/PH12016501093A1/en unknown
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5347572A (en) * | 1976-10-08 | 1978-04-28 | Shimizugen Shiyouten Kk | Food coloring method |
CN1119660A (zh) * | 1994-07-21 | 1996-04-03 | 宾-古里安尼格夫大学研究及发展部 | 着色剂 |
WO2005065697A1 (fr) * | 2003-12-12 | 2005-07-21 | Florence Minard | Procede de photo-stabilisation de phycobiliproteines dans un extrait aqueux, compositions contenant des phycobiliproteines stabilisees et utilisation de phycobiliproteines stabilisees |
EP1591099A2 (en) * | 2004-04-28 | 2005-11-02 | MERCK PATENT GmbH | Methods for stabilizing ingredients within cosmetics, personal care and household products |
US20050244349A1 (en) * | 2004-04-28 | 2005-11-03 | Ratan Chaudhuri | Methods for stabilizing ingredients within cosmetics, personal care and household products |
CN101778572A (zh) * | 2007-08-02 | 2010-07-14 | 荷兰联合利华有限公司 | 包含多酚的组合物 |
CN101891809A (zh) * | 2010-06-18 | 2010-11-24 | 中国科学院海洋研究所 | 一种藻蓝蛋白提取物的制备和应用 |
CN101948887A (zh) * | 2010-08-27 | 2011-01-19 | 中国石油大学(华东) | 一种重组藻蓝胆素的制备方法及其应用 |
CN102140259A (zh) * | 2010-12-22 | 2011-08-03 | 晨光生物科技集团股份有限公司 | 一种红米红色素的稳定化处理方法 |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106667794A (zh) * | 2017-01-25 | 2017-05-17 | 西安科艺诗生物技术有限公司 | 一种提高色素蛋白光稳定性的包合物及应用 |
CN107047972A (zh) * | 2017-04-24 | 2017-08-18 | 苏州维淼生物工程有限公司 | 一种添加水华蓝藻提取物的功能性饲料 |
CN107047972B (zh) * | 2017-04-24 | 2020-12-11 | 苏州维淼生物工程有限公司 | 一种添加水华蓝藻提取物的功能性饲料 |
CN110753496A (zh) * | 2017-06-15 | 2020-02-04 | 奥伽马公司 | 获得包含微藻和/或蓝细菌提取物的由果汁制成的稳定化食品饮料的方法 |
CN112087954A (zh) * | 2018-12-17 | 2020-12-15 | Dic株式会社 | 色素材料水溶液、色素材料水溶液的制造方法和蓝色着色饮料 |
CN113645855A (zh) * | 2019-05-29 | 2021-11-12 | 科汉森天然色素有限责任公司 | 藻蓝蛋白的稳定 |
WO2022073438A1 (zh) * | 2020-10-09 | 2022-04-14 | 暨南大学 | 一种高负载藻蓝蛋白的纳米颗粒及其制备方法与应用 |
CN115607477A (zh) * | 2022-10-24 | 2023-01-17 | 中国海洋大学 | 维持藻蓝蛋白在酸性条件下热稳定性的方法 |
CN115607477B (zh) * | 2022-10-24 | 2024-04-02 | 中国海洋大学 | 维持藻蓝蛋白在酸性条件下热稳定性的方法 |
Also Published As
Publication number | Publication date |
---|---|
MX2016008084A (es) | 2016-10-12 |
KR20160098272A (ko) | 2016-08-18 |
WO2015090697A1 (en) | 2015-06-25 |
JP2017509316A (ja) | 2017-04-06 |
AU2014365657A1 (en) | 2016-06-23 |
PH12016501093A1 (en) | 2016-07-11 |
US20160324745A1 (en) | 2016-11-10 |
EP3091852A1 (en) | 2016-11-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105813471A (zh) | 用于蓝色的稳定化的藻蓝蛋白 | |
CN109219640B (zh) | 色素材料及色素材料的制造方法 | |
CN104320979A (zh) | 包含至少一种着色剂和至少一种多糖的组合的组合物 | |
Brauch et al. | Studies into the stability of 3-O-glycosylated and 3, 5-O-diglycosylated anthocyanins in differently purified liquid and dried maqui (Aristotelia chilensis (Mol.) Stuntz) preparations during storage and thermal treatment | |
US20140080923A1 (en) | Stevia based sweetening composition | |
KR101543569B1 (ko) | 칼라만시를 이용한 안토시아닌 함유 천연 추출물의 안정화 방법 | |
CN113645855A (zh) | 藻蓝蛋白的稳定 | |
CN102835649A (zh) | 栀子黄色素护色剂及其制造方法 | |
JP2002065201A (ja) | 色素の退色防止剤 | |
US20190161465A1 (en) | Red colorant composition derived from iridoid compounds and method for producing same | |
US20150164119A1 (en) | Red composition | |
CN113693152A (zh) | 富含花青素的软糖及制作工艺 | |
WO2020213447A9 (ja) | クチナシ青色素及びその製造方法 | |
Szot et al. | The Beneficial Effects of Anthocyanins from Cornelian Cherry (Cornus mas L.) Fruits and Their Possible Uses: A Review | |
Sigwela | Extraction, characterisation and application of betalains from cactus pear, beetroot and amaranth | |
JP2001321120A (ja) | 健康食品 | |
JP6445518B2 (ja) | マスカダインポマース抽出物の調製方法 | |
Yulia et al. | Determination of Total Flavonoid Levels in Packaged Tea Bags Combination of Dayak Onion and Beet Root with UV Visible Spectrophotometric Method | |
JP2006306966A (ja) | アントシアニンを安定化する組成物 | |
Maryam | Total phenol, flavonoid levels and IC50 in local grape (Vitis vinifera L) skin waste wine | |
JP7317400B2 (ja) | ブラックジンジャー抽出物含有組成物及び経口用組成物 | |
RU2405379C1 (ru) | Сироп профилактический | |
JP2004033106A (ja) | 退色抑制剤 | |
Enache et al. | A new natural food dye: microencapsulated Cornelian cherry bioactive compounds | |
RU2177015C1 (ru) | Краситель антоциановый из растительного сырья |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
WD01 | Invention patent application deemed withdrawn after publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20160727 |