JP2016178913A - Method for producing ketooctadecadienoic acid - Google Patents
Method for producing ketooctadecadienoic acid Download PDFInfo
- Publication number
- JP2016178913A JP2016178913A JP2015062418A JP2015062418A JP2016178913A JP 2016178913 A JP2016178913 A JP 2016178913A JP 2015062418 A JP2015062418 A JP 2015062418A JP 2015062418 A JP2015062418 A JP 2015062418A JP 2016178913 A JP2016178913 A JP 2016178913A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- metal
- ketooctadecadienoic
- oxo
- oil
- 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.)
- Granted
Links
- IDEOITKGHXRKLG-UHFFFAOYSA-N Oxo-octadecadienoic acid Chemical compound CCCCCCCCCCCCC(=O)C=CC=CC(O)=O IDEOITKGHXRKLG-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 37
- 229910052751 metal Inorganic materials 0.000 claims abstract description 46
- 239000002184 metal Substances 0.000 claims abstract description 46
- 239000002994 raw material Substances 0.000 claims abstract description 31
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims abstract description 26
- 102000004190 Enzymes Human genes 0.000 claims abstract description 25
- 108090000790 Enzymes Proteins 0.000 claims abstract description 25
- 235000020778 linoleic acid Nutrition 0.000 claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 25
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims abstract description 23
- 102000003820 Lipoxygenases Human genes 0.000 claims abstract description 11
- 108090000128 Lipoxygenases Proteins 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 10
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 40
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 26
- 235000010469 Glycine max Nutrition 0.000 claims description 22
- 244000068988 Glycine max Species 0.000 claims description 22
- 108090001060 Lipase Proteins 0.000 claims description 19
- 102000004882 Lipase Human genes 0.000 claims description 19
- 239000004367 Lipase Substances 0.000 claims description 19
- 235000019421 lipase Nutrition 0.000 claims description 19
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 16
- 239000011701 zinc Substances 0.000 claims description 16
- 229910052725 zinc Inorganic materials 0.000 claims description 16
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052748 manganese Inorganic materials 0.000 claims description 14
- 239000011572 manganese Substances 0.000 claims description 14
- 229910052742 iron Inorganic materials 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 12
- 239000008157 edible vegetable oil Substances 0.000 claims description 11
- 108090000371 Esterases Proteins 0.000 claims description 10
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 8
- 235000012424 soybean oil Nutrition 0.000 claims description 7
- 239000003549 soybean oil Substances 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- JHXAZBBVQSRKJR-UHFFFAOYSA-N coriolic acid Natural products CCCCCC(=O)C=CC=CCCCCCCCC(O)=O JHXAZBBVQSRKJR-UHFFFAOYSA-N 0.000 claims description 4
- JHXAZBBVQSRKJR-KDFHGORWSA-N 13-oxo-9E,11E-ODE Chemical compound CCCCCC(=O)\C=C\C=C\CCCCCCCC(O)=O JHXAZBBVQSRKJR-KDFHGORWSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 abstract description 14
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 26
- 229940088598 enzyme Drugs 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 235000013305 food Nutrition 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000007853 buffer solution Substances 0.000 description 11
- -1 linoleic acid ester Chemical class 0.000 description 11
- 102000023984 PPAR alpha Human genes 0.000 description 10
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 8
- 235000019645 odor Nutrition 0.000 description 8
- 230000001953 sensory effect Effects 0.000 description 8
- 230000004913 activation Effects 0.000 description 7
- 238000005273 aeration Methods 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 238000010525 oxidative degradation reaction Methods 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 5
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 5
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 235000014593 oils and fats Nutrition 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 235000013555 soy sauce Nutrition 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 235000015067 sauces Nutrition 0.000 description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101710088194 Dehydrogenase Proteins 0.000 description 3
- 208000032928 Dyslipidaemia Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 208000017170 Lipid metabolism disease Diseases 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 108010016731 PPAR gamma Proteins 0.000 description 3
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000011194 food seasoning agent Nutrition 0.000 description 3
- 235000013376 functional food Nutrition 0.000 description 3
- 239000003264 margarine Substances 0.000 description 3
- 235000013310 margarine Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000008685 targeting Effects 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- ADHNUPOJJCKWRT-SENDIRFWSA-N (2z)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCC=C\C=C/C(O)=O ADHNUPOJJCKWRT-SENDIRFWSA-N 0.000 description 2
- 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
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 description 2
- LUZSWWYKKLTDHU-SIGMCMEVSA-N 9-oxo-10E,12E-ODE Chemical compound CCCCC\C=C\C=C\C(=O)CCCCCCCC(O)=O LUZSWWYKKLTDHU-SIGMCMEVSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- 244000294411 Mirabilis expansa Species 0.000 description 2
- 235000015429 Mirabilis expansa Nutrition 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 235000010582 Pisum sativum Nutrition 0.000 description 2
- 240000004713 Pisum sativum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 210000001789 adipocyte Anatomy 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000012136 culture method Methods 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 230000004069 differentiation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229910000358 iron sulfate Inorganic materials 0.000 description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 230000037356 lipid metabolism Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- ISPYRSDWRDQNSW-UHFFFAOYSA-L manganese(II) sulfate monohydrate Chemical compound O.[Mn+2].[O-]S([O-])(=O)=O ISPYRSDWRDQNSW-UHFFFAOYSA-L 0.000 description 2
- 235000013536 miso Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000013322 soy milk Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 1
- ADHNUPOJJCKWRT-KRPOFHJFSA-N (2E)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCC=C\C=C\C(O)=O ADHNUPOJJCKWRT-KRPOFHJFSA-N 0.000 description 1
- YKHVVNDSWHSBPA-BLHCBFLLSA-N (2E,4E)-deca-2,4-dienoic acid Chemical compound CCCCC\C=C\C=C\C(O)=O YKHVVNDSWHSBPA-BLHCBFLLSA-N 0.000 description 1
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- YVWMHFYOIJMUMN-CYZWUHAYSA-N (6e,8e)-5-oxooctadeca-6,8-dienoic acid Chemical compound CCCCCCCCC\C=C\C=C\C(=O)CCCC(O)=O YVWMHFYOIJMUMN-CYZWUHAYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 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 1
- PQDJTTDGUJFDQI-UHFFFAOYSA-N 11-oxooctadeca-9,12-dienoic acid Chemical compound CCCCCC=CC(=O)C=CCCCCCCCC(O)=O PQDJTTDGUJFDQI-UHFFFAOYSA-N 0.000 description 1
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
- 108010011619 6-Phytase Proteins 0.000 description 1
- LUZSWWYKKLTDHU-UHFFFAOYSA-N 9-EEZ-KODE Natural products CCCCCC=CC=CC(=O)CCCCCCCC(O)=O LUZSWWYKKLTDHU-UHFFFAOYSA-N 0.000 description 1
- LUZSWWYKKLTDHU-ZJHFMPGASA-N 9-oxo-ODE Chemical compound CCCCC\C=C/C=C/C(=O)CCCCCCCC(O)=O LUZSWWYKKLTDHU-ZJHFMPGASA-N 0.000 description 1
- 241000208223 Anacardiaceae Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241001107116 Castanospermum australe Species 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 235000010523 Cicer arietinum Nutrition 0.000 description 1
- 244000045195 Cicer arietinum Species 0.000 description 1
- 241000235646 Cyberlindnera jadinii Species 0.000 description 1
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 1
- 102000003849 Cytochrome P450 Human genes 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 102000000476 Fatty Acid Transport Proteins Human genes 0.000 description 1
- 108010055870 Fatty Acid Transport Proteins Proteins 0.000 description 1
- 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 1
- 108010068370 Glutens Proteins 0.000 description 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000758791 Juglandaceae Species 0.000 description 1
- 241000235649 Kluyveromyces Species 0.000 description 1
- 240000004322 Lens culinaris Species 0.000 description 1
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 1
- 101710098556 Lipase A Proteins 0.000 description 1
- 241000219745 Lupinus Species 0.000 description 1
- 101710099648 Lysosomal acid lipase/cholesteryl ester hydrolase Proteins 0.000 description 1
- 102100026001 Lysosomal acid lipase/cholesteryl ester hydrolase Human genes 0.000 description 1
- 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 1
- 241000124008 Mammalia Species 0.000 description 1
- YBHQCJILTOVLHD-YVMONPNESA-N Mirin Chemical compound S1C(N)=NC(=O)\C1=C\C1=CC=C(O)C=C1 YBHQCJILTOVLHD-YVMONPNESA-N 0.000 description 1
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 1
- SHBFQDIKJJBLCR-UHFFFAOYSA-N O=C(C=CCC=CCCCCCCCC(=O)O)CCCC Chemical compound O=C(C=CCC=CCCCCCCCC(=O)O)CCCC SHBFQDIKJJBLCR-UHFFFAOYSA-N 0.000 description 1
- GYPRIPVTZCJPAB-UHFFFAOYSA-N O=C(CC=CCCCCCCCC(=O)O)C=CCCCC Chemical compound O=C(CC=CCCCCCCCC(=O)O)C=CCCCC GYPRIPVTZCJPAB-UHFFFAOYSA-N 0.000 description 1
- YVEHOEVYPXBDCL-UHFFFAOYSA-N O=C(CCCCC(=O)O)CCC=CCC=CCCCCC Chemical compound O=C(CCCCC(=O)O)CCC=CCC=CCCCCC YVEHOEVYPXBDCL-UHFFFAOYSA-N 0.000 description 1
- WVJQLSMJXJJFLT-UHFFFAOYSA-N O=C(CCCCCCC(=O)O)C=CCC=CCCCCC Chemical compound O=C(CCCCCCC(=O)O)C=CCC=CCCCCC WVJQLSMJXJJFLT-UHFFFAOYSA-N 0.000 description 1
- 241000207836 Olea <angiosperm> Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 102000004020 Oxygenases Human genes 0.000 description 1
- 108090000417 Oxygenases Proteins 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 235000008753 Papaver somniferum Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 102000011420 Phospholipase D Human genes 0.000 description 1
- 108090000553 Phospholipase D Proteins 0.000 description 1
- 108010064785 Phospholipases Proteins 0.000 description 1
- 102000015439 Phospholipases Human genes 0.000 description 1
- 108010073135 Phosphorylases Proteins 0.000 description 1
- 102000009097 Phosphorylases Human genes 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 240000006711 Pistacia vera Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000040738 Sesamum orientale Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000006364 Torula Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 240000004922 Vigna radiata Species 0.000 description 1
- 235000010721 Vigna radiata var radiata Nutrition 0.000 description 1
- 235000011469 Vigna radiata var sublobata Nutrition 0.000 description 1
- 240000001417 Vigna umbellata Species 0.000 description 1
- 235000011453 Vigna umbellata Nutrition 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 235000019498 Walnut oil Nutrition 0.000 description 1
- 241000235017 Zygosaccharomyces Species 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 235000013527 bean curd Nutrition 0.000 description 1
- 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 1
- 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 1
- 235000021279 black bean Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 235000020226 cashew nut Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 108010010102 chlorogenic acid esterase Proteins 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 229940108924 conjugated linoleic acid Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008162 cooking oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000014048 cultured milk product Nutrition 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000018823 dietary intake Nutrition 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000015071 dressings Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000013611 frozen food Nutrition 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000008169 grapeseed oil Substances 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- XDQQQSFYCSYSCP-UHFFFAOYSA-N kaempferol 3-O-beta-D-glucopyranosyl(1-3)-alpha-L-rhamnopyranosyl(1-6)-beta-D-glucopyranoside Natural products CC=CCCC=CCCC(O)=O XDQQQSFYCSYSCP-UHFFFAOYSA-N 0.000 description 1
- 235000008960 ketchup Nutrition 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- SCVOEYLBXCPATR-UHFFFAOYSA-L manganese(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Mn+2].[O-]S([O-])(=O)=O SCVOEYLBXCPATR-UHFFFAOYSA-L 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 235000008519 pasta sauces Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 235000020233 pistachio Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 235000019992 sake Nutrition 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000020083 shōchū Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 238000000956 solid--liquid extraction Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 229930185549 teaseedsaponin Natural products 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 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
- 235000020234 walnut Nutrition 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
本発明は、ケトオクタデカジエン酸の製造方法に関する。 The present invention relates to a method for producing ketooctadecadienoic acid.
近年、世界中で過度な食事摂取により、糖尿病、脂質代謝異常症、高血圧、肥満等の生活習慣病と呼ばれる疾患が増加している。脂質代謝異常症を改善する薬剤としては、ペルオキシゾーム増殖剤応答性受容体(PPAR)をターゲットとする成分が多数開発されている。 In recent years, due to excessive dietary intake around the world, diseases called lifestyle-related diseases such as diabetes, dyslipidemia, hypertension and obesity are increasing. A number of components targeting peroxisome proliferator-activated receptors (PPARs) have been developed as drugs for improving dyslipidemia.
PPARをターゲットとする成分として、トマト抽出物に含まれる9−オキソ−10,12−オクタデカジエン酸(本明細書中、「9−oxo−ODA」とも略記する。特に明記しない場合は異性体も含むものとする。)及び13−オキソ−9,11−オクタデカジエン酸(本明細書中、「13−oxo−ODA」とも略記する。特に明記しない場合は異性体も含むものとする。)等の成分が知られている(特許文献1)。 As a component targeting PPAR, 9-oxo-10,12-octadecadienoic acid (to be abbreviated as “9-oxo-ODA” in the present specification. Isomers unless otherwise specified) And 13-oxo-9,11-octadecadienoic acid (also abbreviated as “13-oxo-ODA” in the present specification, and also includes isomers unless otherwise specified). Is known (Patent Document 1).
特に、13−oxo−ODAは、in vitroの試験において9−oxo−ODAよりもPPARα活性化能が高いことが知られている(非特許文献1)。 In particular, it is known that 13-oxo-ODA has higher PPARα activation ability than 9-oxo-ODA in an in vitro test (Non-patent Document 1).
9−oxo−ODA、13−oxo−ODA等のケトオクタデカジエン酸は、PPARαをターゲットとする成分として、食品に含有させて利用できる点で有望であり、これらの成分を安定的に供給することができる方法が求められている。 Ketooctadecadienoic acid such as 9-oxo-ODA and 13-oxo-ODA is promising in that it can be used in foods as a component targeting PPARα, and these components can be supplied stably. There is a need for a method that can do this.
そこで、本発明は、副生成物を抑え、効率的にケトオクタデカジエン酸を製造できる製造方法の提供を目的とする。 Then, this invention aims at provision of the manufacturing method which suppresses a by-product and can manufacture ketooctadecadienoic acid efficiently.
すなわち、本発明は、金属の存在下、且つ20℃未満の温度で、リノール酸を含む原料にリポキシゲナーゼを含む酵素材料を作用させる工程を備える、ケトオクタデカジエン酸の製造方法を提供する。 That is, this invention provides the manufacturing method of ketooctadecadienoic acid provided with the process of making the enzyme material containing a lipoxygenase act on the raw material containing a linoleic acid at the temperature below 20 degreeC in presence of a metal.
本発明の製造方法によれば、副生成物を抑え、効率的にケトオクタデカジエン酸を製造することができる。 According to the production method of the present invention, ketooctadecadienoic acid can be produced efficiently while suppressing by-products.
上記製造方法において、金属は、マンガン、亜鉛、鉄、銅及びマグネシウムからなる群より選択される少なくとも一種であってよく、マンガン、亜鉛及び鉄からなる群より選択される少なくとも一種であってよく、マンガン及び亜鉛からなる群より選択される少なくとも一種であってよく、特にマンガンであってもよい。金属として、マンガン、亜鉛、鉄、銅及びマグネシウムからなる群より選択される少なくとも一種を用いることにより、より効果的に副生成物を抑え、より効率的にケトオクタデカジエン酸を製造することができる。さらに、マンガン、亜鉛及び鉄からなる群より選択される少なくとも一種、マンガン及び亜鉛からなる群より選択される少なくとも一種、又はマンガンを用いることにより、これらの効果がより一層向上する。また、金属は、金属含有酵母により供給されるものであってもよい。金属が金属含有酵母により供給されることにより、より食品用途に適したものとなる。 In the above production method, the metal may be at least one selected from the group consisting of manganese, zinc, iron, copper and magnesium, and may be at least one selected from the group consisting of manganese, zinc and iron, It may be at least one selected from the group consisting of manganese and zinc, particularly manganese. By using at least one selected from the group consisting of manganese, zinc, iron, copper and magnesium as the metal, it is possible to more effectively suppress the by-products and produce ketooctadecadienoic acid more efficiently. it can. Further, these effects are further improved by using at least one selected from the group consisting of manganese, zinc and iron, at least one selected from the group consisting of manganese and zinc, or manganese. Moreover, the metal may be supplied by a metal-containing yeast. When the metal is supplied by the metal-containing yeast, it becomes more suitable for food use.
ケトオクタデカジエン酸は、13−オキソ−9,11−オクタデカジエン酸であってもよい。13−oxo−ODAは、例えば9−oxo−ODA等の他のケトオクタデカジエン酸と比較してPPARα活性化能が高い。 The ketooctadecadienoic acid may be 13-oxo-9,11-octadecadienoic acid. 13-oxo-ODA has a higher PPARα activation ability than other ketooctadecadienoic acids such as 9-oxo-ODA.
温度は、0℃以上15℃以下であってもよい。温度を上記範囲とすることにより、副生成物をより効果的に抑えることができ、食品としての風味及び嗜好性が向上する。 The temperature may be 0 ° C. or higher and 15 ° C. or lower. By making temperature into the said range, a by-product can be suppressed more effectively and the flavor and palatability as a foodstuff improve.
リポキシゲナーゼを含む酵素材料は、大豆粉末であってもよい。大豆粉末を用いることにより、酵素材料を安価に入手することができるばかりでなく、食品としての適性を向上させることができる。 The enzyme material containing lipoxygenase may be soybean powder. By using soybean powder, not only can the enzyme material be obtained at low cost, but also the suitability as a food can be improved.
リノール酸を含む原料は、食用油又はその加工物であってよく、当該食用油は、大豆油であってもよい。食用油又はその加工物を用いることにより、原料を安価に入手することができるばかりでなく、食品としての適性を向上させることができる。また、大豆油又はその加工物は、リノール酸の含有量が高いため、生産効率を向上させることができる。 The raw material containing linoleic acid may be edible oil or a processed product thereof, and the edible oil may be soybean oil. By using edible oil or a processed product thereof, not only can the raw material be obtained at a low price, but also the suitability as a food can be improved. Moreover, since soybean oil or its processed material has a high content of linoleic acid, production efficiency can be improved.
また、リノール酸を含む原料が、食用油又はその加工油である場合、上記工程の前に、当該原料にエステラーゼを作用させる工程をさらに備えていてもよく、エステラーゼは、リパーゼであってよい。エステラーゼを作用させる工程をさらに備えることにより、原料中の遊離リノール酸の量を増加させることができ、生産効率を向上させることができる。また、エステラーゼがリパーゼであることにより、より効率的に原料中の遊離リノール酸の量を増加させることができる。 Moreover, when the raw material containing linoleic acid is an edible oil or a processed oil thereof, a step of causing esterase to act on the raw material may be further provided before the above step, and the esterase may be a lipase. By further including the step of causing esterase to act, the amount of free linoleic acid in the raw material can be increased, and the production efficiency can be improved. In addition, since the esterase is a lipase, the amount of free linoleic acid in the raw material can be increased more efficiently.
本発明によれば、副生成物を抑え、効率的にケトオクタデカジエン酸を製造することができる。 According to the present invention, by-products can be suppressed and ketooctadecadienoic acid can be produced efficiently.
以下、本発明を実施するための形態についてより詳細に説明する。しかしながら、本発明は以下の実施形態に限定されるものではない。 Hereinafter, the form for implementing this invention is demonstrated in detail. However, the present invention is not limited to the following embodiments.
本実施形態に係るケトオクタデカジエン酸の製造方法は、金属の存在下、且つ20℃未満の温度で、リノール酸を含む原料にリポキシゲナーゼを含む酵素材料を作用させる工程を備える。 The method for producing ketooctadecadienoic acid according to this embodiment includes a step of causing an enzyme material containing lipoxygenase to act on a raw material containing linoleic acid in the presence of a metal and at a temperature of less than 20 ° C.
ケトオクタデカジエン酸としては、その構造式に限定されず、PPARα活性化作用を有する任意のケトオクタデカジエン酸が挙げられる。例えば、9−オキソ−10(E),12(E)−オクタデカジエン酸、9−オキソ−10(Z),12(E)−オクタデカジエン酸、9−オキソ−10(E),12(Z)−オクタデカジエン酸、9−オキソ−10(Z),12(Z)−オクタデカジエン酸、13−オキソ−9(E),11(E)−オクタデカジエン酸(下記式(I))、13−オキソ−9(Z),11(E)−オクタデカジエン酸(下記式(II))、13−オキソ−9(E),11(Z)−オクタデカジエン酸、13−オキソ−9(Z),11(Z)−オクタデカジエン酸等が挙げられる。また、5−オキソ−6,8−オクタデカジエン酸、6−オキソ−9,12−オクタデカジエン酸、8−オキソ−9,12−オクタデカジエン酸、10−オキソ−8,12−オクタデカジエン酸、11−オキソ−9,12−オクタデカジエン酸、12−オキソ−9,13−オクタデカジエン酸、14−オキソ−9,12−オクタデカジエン酸等も挙げられ、これらは、(E,E)体、(Z,E)体、(E,Z)体、(Z,Z)体のいずれであってもよい。ケトオクタデカジエン酸としては、PPARα活性化能に優れる観点から、9−oxo−ODA又は13−oxo−ODAであってもよく、13−oxo−ODAであってもよく、下記式(I)又は下記式(II)で表される化合物であってもよい。 The ketooctadecadienoic acid is not limited to its structural formula, and includes any ketooctadecadienoic acid having a PPARα activation action. For example, 9-oxo-10 (E), 12 (E) -octadecadienoic acid, 9-oxo-10 (Z), 12 (E) -octadecadienoic acid, 9-oxo-10 (E), 12 (Z) -octadecadienoic acid, 9-oxo-10 (Z), 12 (Z) -octadecadienoic acid, 13-oxo-9 (E), 11 (E) -octadecadienoic acid (the following formula ( I)), 13-oxo-9 (Z), 11 (E) -octadecadienoic acid (following formula (II)), 13-oxo-9 (E), 11 (Z) -octadecadienoic acid, 13 -Oxo-9 (Z), 11 (Z) -octadecadienoic acid and the like. Further, 5-oxo-6,8-octadecadienoic acid, 6-oxo-9,12-octadecadienoic acid, 8-oxo-9,12-octadecadienoic acid, 10-oxo-8,12-octa Examples include decadienoic acid, 11-oxo-9,12-octadecadienoic acid, 12-oxo-9,13-octadecadienoic acid, 14-oxo-9,12-octadecadienoic acid, and the like. Any of (E, E) body, (Z, E) body, (E, Z) body, and (Z, Z) body may be sufficient. The ketooctadecadienoic acid may be 9-oxo-ODA or 13-oxo-ODA, or 13-oxo-ODA from the viewpoint of excellent PPARα activation ability, and may have the following formula (I) Alternatively, it may be a compound represented by the following formula (II).
ケトオクタデカジエン酸は、PPAR活性化能を有する。PPARは、哺乳類ではα、δ及びγの3種類のアイソフォームが知られており、上記ケトオクタデカジエン酸は、少なくともPPARα及びPPARγの活性化能を有することが知られている。PPARαは主に肝臓及び骨格筋で脂肪酸の輸送及び代謝に関連する遺伝子の発現を制御していることが知ら得ている。PPARαは、このような作用を介して脂質代謝に深く関与していることから、PPARα活性化能を有する上記ケトオクタデカジエン酸は、脂質代謝異常症の改善に有効である。また、PPARγは、脂肪細胞の分化を司る調節因子であることが知られている。したがって、PPARγ活性化能を有する上記ケトオクタデカジエン酸は、脂肪細胞分化を促進することにより、血液中の糖及び遊離脂肪酸を低下させ、筋肉の遊離脂肪酸の低下とインスリン抵抗性の改善に有効である。 Ketooctadecadienoic acid has PPAR activation ability. PPAR has three known isoforms of α, δ, and γ in mammals, and the above-mentioned ketooctadecadienoic acid is known to have at least the ability to activate PPARα and PPARγ. It is known that PPARα regulates the expression of genes related to fatty acid transport and metabolism mainly in the liver and skeletal muscle. Since PPARα is deeply involved in lipid metabolism through such actions, the above-mentioned ketooctadecadienoic acid having PPARα activation ability is effective in improving lipid metabolism abnormalities. PPARγ is known to be a regulatory factor that governs the differentiation of adipocytes. Therefore, the above-mentioned ketooctadecadienoic acid having the ability to activate PPARγ promotes adipocyte differentiation, thereby reducing blood sugar and free fatty acids, and effective in reducing muscle free fatty acids and improving insulin resistance. It is.
ケトオクタデカジエン酸は、例えば、下記スキーム(A)に示す経路でリノール酸から、リポキシゲナーゼ及びデヒドロゲナーゼによる酸素付加反応により生成されると考えられる。また、シトクロムP450、麹菌等のオキシゲナーゼによる酸素付加反応により生成されることも考えられる。なお、下記スキーム(A)における過酸化物は、デヒドロゲナーゼによらずとも、分解してケトオクタデカジエン酸を生成することができる。 Ketooctadecadienoic acid is considered to be produced, for example, from linoleic acid by the oxygen addition reaction by lipoxygenase and dehydrogenase through the route shown in the following scheme (A). In addition, it may be generated by an oxygen addition reaction with oxygenase such as cytochrome P450 or Neisseria gonorrhoeae. In addition, the peroxide in the following scheme (A) can be decomposed to produce ketooctadecadienoic acid regardless of dehydrogenase.
したがって、上記原料は、リノール酸を含むものであればよい。リノール酸としては、リノール酸のほか、共役リノール酸等も挙げられる。また、上記原料は、リノール酸のほか、リノレン酸やリノール酸のエステル体が含まれていてもよい。リノール酸のエステル体としては、リノール酸のカルボキシル基がエステル化されたものであればよく、例えば、メチルエステル、エチルエステル、グリセリン脂肪酸エステル(トリアシルグリセロール、ジグリセリン脂肪酸エステル、モノグリセリン脂肪酸エステル等)、リン脂質(ホスファチジルコリン、ホスファチジルエタノールアミン、ホスファチジルイノシトール、ホスファチジン酸、ホスファチジルセリン等)とのエステル、グリセロ糖脂質とのエステル等が挙げられる。 Therefore, the said raw material should just contain a linoleic acid. Examples of linoleic acid include conjugated linoleic acid in addition to linoleic acid. Moreover, the said raw material may contain the ester body of linolenic acid and linoleic acid other than linoleic acid. The linoleic acid ester may be any linoleic acid carboxyl group esterified, such as methyl ester, ethyl ester, glycerin fatty acid ester (triacylglycerol, diglycerin fatty acid ester, monoglycerin fatty acid ester, etc. ), Esters with phospholipids (phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidic acid, phosphatidylserine, etc.), esters with glyceroglycolipids, and the like.
上記原料としては、精製されたリノール酸を用いてもよく、丸大豆又は丸大豆の加工物を含む原料、食用油(ひまわり油、綿実油、とうもろこし油、大豆油、ごま油、クルミ油、グレープ種子油、米ぬか油、落花生油、なたね油、オリーブ油、亜麻仁油、シソ油、エゴマ油、魚油、ラード、パーム油及びヤシ油等)又はその加工物を含む原料、しょうゆ油又はその加工物を含む原料、小麦、エンドウ豆、そら豆、小豆、レンズ豆、ひよこ豆、リョクトウ、コーヒー豆、キマメ、ごま、とうもろこし、くるみ、落花生、そば、けし、松の実、かや、黒豆、エゴマ、オリーブの実、カシューナッツ、ピスタチオ、ルーピン豆、ひまわり種子、グレープ種子、トマト種子、オリーブ種子、米ぬか、若しくはその他リノール酸を含有する穀類、豆類、ナッツ類若しくは種子等、又はこれらの加工物等のリノール酸を含む原料を用いてもよい。食用油脂製造過程において、脱酸処理の際に生じる副産物(脂肪酸等を含む)、又はトコフェロール等の精製過程で生じる副産物を用いてもよい。リノール酸の含有量が高い点から、食用油又はその加工物を含む原料、特に大豆油又はその加工物を含む原料を用いてもよい。食用油の加工物としては、マーガリン、スプレッド、改良油脂、粉末油脂等を用いることができ、大豆油の加工物としては、同様にマーガリン、スプレッド、改良油脂、粉末油脂等を用いることができる。 As the above raw material, refined linoleic acid may be used, raw materials containing whole soybeans or whole soybeans, edible oil (sunflower oil, cottonseed oil, corn oil, soybean oil, sesame oil, walnut oil, grape seed oil , Rice bran oil, peanut oil, rapeseed oil, olive oil, linseed oil, perilla oil, sesame oil, fish oil, lard, palm oil, coconut oil, etc.) or processed materials thereof, soy sauce oil or raw materials including processed products thereof, wheat , Peas, broad beans, red beans, lentils, chickpeas, mung bean, coffee beans, bean, sesame, corn, walnuts, peanuts, buckwheat, poppy, pine nuts, pods, black beans, egoma, olives, cashews, Pistachios, lupine beans, sunflower seeds, grape seeds, tomato seeds, olive seeds, rice bran, or other grains containing linoleic acid, beans, Tsu Tsu such or seeds, or may be used a raw material containing linoleic acid such as those of the workpiece. In the production of edible fats and oils, by-products (including fatty acids) generated during the deoxidation treatment, or by-products generated during the purification process such as tocopherol may be used. In view of the high content of linoleic acid, a raw material containing edible oil or a processed product thereof, particularly a raw material containing soybean oil or a processed product thereof may be used. Margarine, spreads, improved oils and fats, powdered oils and fats can be used as processed edible oils, and margarine, spreads, improved oils and fats, powdered oils and fats and the like can be used as processed products of soybean oils.
本実施形態に係るケトオクタデカジエン酸の製造方法は、上述したリノール酸を含む原料に、リポキシゲナーゼを含む酵素材料を作用させる。このような酵素材料としては、特に制限はなく、リポキシゲナーゼの精製酵素を用いてもよいし、大豆、トウモロコシ、エンドウ、オオムギ、コムギ、ピーナッツ、ジャガイモ、トマト等の、リポキシゲナーゼを多量に含む材料を用いてもよい。これらの材料は、前処理することなくそのままで、又は破砕・粉砕等を行い、粉末状・微粒子状にして用いることができる。また、材料に適度に水を加え、又は水を加えずに、例えば石臼等で摩砕し、液状又はペースト状にして用いることができる。例えば、大豆粉末は、生大豆をミキサー等で破砕し粉末化したものを用いることができる。酵素材料は、リポキシゲナーゼのほかに酵素を含んでいてもよく、例えば、デヒドロゲナーゼを含んでいてもよい。 In the method for producing ketooctadecadienoic acid according to this embodiment, an enzyme material containing lipoxygenase is allowed to act on the raw material containing linoleic acid described above. The enzyme material is not particularly limited, and a purified enzyme of lipoxygenase may be used, or a material containing a large amount of lipoxygenase such as soybean, corn, pea, barley, wheat, peanut, potato, tomato, etc. is used. May be. These materials can be used in the form of powder or fine particles as they are without pretreatment or after being crushed and pulverized. Moreover, it can grind | pulverize, for example with a stone mortar etc., without adding water moderately to a material, and can be used in liquid form or paste form. For example, soybean powder obtained by crushing raw soybean with a mixer or the like and pulverizing it can be used. The enzyme material may contain an enzyme in addition to lipoxygenase, and may contain, for example, dehydrogenase.
酵素材料の添加量としては、用いる原料及び下記にて詳述する金属の種類に応じて適宜設定すればよいが、例えば、原料100質量部に対して、酵素材料において、酵素活性で換算したときに、リポキシゲナーゼが1000〜50000ユニット、2000〜40000ユニット又は3000〜20000ユニットとしてもよい。なお、ここで1ユニットは、リノール酸を基質とし、3mL(幅1cm)の石英セル内において、pH9、温度25℃で1分間に吸光度を0.001増加させる酵素量と定義する。 The addition amount of the enzyme material may be appropriately set according to the raw material used and the type of metal described in detail below. For example, when converted to enzyme activity in the enzyme material with respect to 100 parts by mass of the raw material, Furthermore, the lipoxygenase may be 1000 to 50000 units, 2000 to 40000 units, or 3000 to 20000 units. Here, 1 unit is defined as the amount of enzyme that increases the absorbance by 0.001 per minute at a pH of 9 and a temperature of 25 ° C. in a 3 mL (width 1 cm) quartz cell using linoleic acid as a substrate.
本実施形態に係るケトオクタデカジエン酸の製造方法は、上述した原料及び酵素材料を、金属の存在下で作用させる工程を備える。金属を用いることで、後述する温度範囲であっても、効率的にケトオクタデカジエン酸を製造することができる。これらの金属は、当該金属を含む化合物又は塩により供給されてもよい。金属を含む化合物又は塩としては、例えば、硫酸マンガン、硫酸マンガン一水和物、硫酸マンガン五水和物、硫酸鉄、硫酸亜鉛等が挙げられる。上記金属の中でも、過酸化脂質等の副生成物をさらに抑制し、より効率的にケトオクタデカジエン酸を製造する観点から、マンガン、亜鉛、鉄、銅及びマグネシウムからなる群より選択される少なくとも一種であってよく、マンガン、亜鉛及び鉄からなる群より選択される少なくとも一種であってよく、マンガン及び亜鉛からなる群より選択される少なくとも一種であってよく、マンガンであってよい。 The method for producing ketooctadecadienoic acid according to this embodiment includes a step of causing the above-described raw materials and enzyme material to act in the presence of a metal. By using a metal, ketooctadecadienoic acid can be efficiently produced even in the temperature range described below. These metals may be supplied by a compound or salt containing the metal. Examples of the metal-containing compound or salt include manganese sulfate, manganese sulfate monohydrate, manganese sulfate pentahydrate, iron sulfate, and zinc sulfate. Among the above metals, at least selected from the group consisting of manganese, zinc, iron, copper and magnesium from the viewpoint of further suppressing by-products such as lipid peroxide and more efficiently producing ketooctadecadienoic acid. It may be one, may be at least one selected from the group consisting of manganese, zinc and iron, may be at least one selected from the group consisting of manganese and zinc, and may be manganese.
また、上記金属は、本実施形態に係る製造方法により製造されたケトオクタデカジエン酸を食品に添加して用いる観点から、金属含有酵母により供給されてもよい。金属含有酵母は、市販品を用いてもよいし、培地等に所望の金属を添加して酵母を適宜培養して酵母中に金属を取り込ませることで調製してもよい。酵母の培養方法としては、一般的に用いられる酵母の培養方法を適宜採用することができる。用いる酵母としては、食用に用いられた実績のある食品グレードの酵母を用いてもよい。具体的には、例えば、ビール酵母、パン酵母、清酒酵母、焼酎酵母、醤油酵母、味噌酵母、トルラ酵母、酵母エキス全般に使用される酵母等が挙げられる。酵母の属・種としては、Saccharomyces属(例えば、Saccharomyces cerevisiae)、Candida属(例えば、Candida utilis)、Hansenula属、Zygosaccharomyces属、Kluyveromyces属等が挙げられる。金属含有酵母としては、例えば、マンガン含有酵母、亜鉛含有酵母、鉄含有酵母、マグネシウム含有酵母、銅含有酵母等が挙げられる。これらは一種を単独で、又は二種以上を併用して用いることができる。これらの金属含有酵母の中でも、過酸化脂質等の副生成物をさらに抑制し、より効率的にケトオクタデカジエン酸を製造する観点から、マンガン含有酵母、亜鉛含有酵母を用いてもよく、マンガン含有酵母を用いてもよい。金属含有酵母における金属の含有量は、特に制限されず、用いる酵母及び金属に応じて適宜設定されるが、例えば、0.1〜50%又は1〜10%であってよい。 Moreover, the said metal may be supplied with a metal containing yeast from a viewpoint which adds and uses ketooctadecadienoic acid manufactured by the manufacturing method which concerns on this embodiment to a foodstuff. The metal-containing yeast may be a commercially available product, or may be prepared by adding a desired metal to a medium or the like, appropriately culturing the yeast, and incorporating the metal into the yeast. As a yeast culture method, a commonly used yeast culture method can be appropriately employed. As the yeast to be used, a food grade yeast having a proven track record used for food may be used. Specific examples include beer yeast, baker's yeast, sake yeast, shochu yeast, soy sauce yeast, miso yeast, torula yeast, yeast used in general for yeast extract, and the like. Examples of the genus / species of yeast include the genus Saccharomyces (for example, Saccharomyces cerevisiae), the genus Candida (for example, Candida utilis), the genus Hansenula, the genus Zygosaccharomyces, and the genus Kluyveromyces. Examples of the metal-containing yeast include manganese-containing yeast, zinc-containing yeast, iron-containing yeast, magnesium-containing yeast, and copper-containing yeast. These can be used individually by 1 type or in combination of 2 or more types. Among these metal-containing yeasts, manganese-containing yeasts and zinc-containing yeasts may be used from the viewpoint of further suppressing by-products such as lipid peroxide and producing ketooctadecadienoic acid more efficiently. Containing yeast may be used. The metal content in the metal-containing yeast is not particularly limited and is appropriately set according to the yeast and the metal to be used, and may be, for example, 0.1 to 50% or 1 to 10%.
反応液中における金属の含有濃度としては、用いる原料及び酵素材料の種類に応じて適宜設定すればよいが、例えば、金属の濃度を0.1〜500mM、0.5〜200mM又は1〜110mMとしてもよい。金属として鉄を用いる場合には、鉄の濃度を1〜200mM又は10〜60mMとしてもよい。また、金属含有酵母を用いる場合には、金属の含有量が上記の範囲内になるように用いればよい。 What is necessary is just to set suitably as content concentration of the metal in a reaction liquid according to the kind of raw material and enzyme material to be used, for example, the density | concentration of a metal shall be 0.1-500 mM, 0.5-200 mM, or 1-110 mM. Also good. When iron is used as the metal, the iron concentration may be 1 to 200 mM or 10 to 60 mM. Moreover, what is necessary is just to use so that content of a metal may become in said range when using metal containing yeast.
本実施形態に係るケトオクタデカジエン酸の製造方法における反応温度は、20℃未満である。温度を20℃未満とすることで、副生成物を抑え、効率的にケトオクタデカジエン酸を製造することができる。一方、上記温度は、上記酵素反応をより効率的に進行させる観点から、0℃以上であってもよい。このような観点から、本実施形態に係るケトオクタデカジエン酸の製造方法における反応温度は、0℃以上15℃以下、0℃以上10℃以下又は0℃以上5℃以下であってもよい。 The reaction temperature in the method for producing ketooctadecadienoic acid according to this embodiment is less than 20 ° C. By setting the temperature to less than 20 ° C., by-products can be suppressed and ketooctadecadienoic acid can be efficiently produced. On the other hand, the temperature may be 0 ° C. or higher from the viewpoint of allowing the enzyme reaction to proceed more efficiently. From such a viewpoint, the reaction temperature in the method for producing ketooctadecadienoic acid according to this embodiment may be 0 ° C. or higher and 15 ° C. or lower, 0 ° C. or higher and 10 ° C. or lower, or 0 ° C. or higher and 5 ° C. or lower.
本実施形態に係るケトオクタデカジエン酸の製造方法における反応時間は、用いる原料、酵素材料及び金属の種類、これらの濃度、反応温度、溶存酸素濃度、撹拌速度、圧力、pH等の物理化学的条件に応じて、また、製造されるケトオクタデカジエン酸の収率を考慮して適宜設定すればよいが、例えば、5分〜120時間、30分〜96時間、1〜24時間又は3〜8時間の範囲であってよい。 The reaction time in the method for producing ketooctadecadienoic acid according to the present embodiment includes the types of raw materials, enzyme materials and metals to be used, their concentration, reaction temperature, dissolved oxygen concentration, stirring speed, pressure, pH, and other physicochemical properties. Depending on the conditions, it may be appropriately set in consideration of the yield of the ketooctadecadienoic acid to be produced. For example, 5 minutes to 120 hours, 30 minutes to 96 hours, 1 to 24 hours or 3 to 3 hours. It may be in the range of 8 hours.
また、上述した原料、酵素材料及び金属を用いてケトオクタデカジエン酸を製造する際の具体的な操作方法についても特に制限されない。例えば、緩衝液中に原料、酵素材料及び金属を添加して、ジャーファーメンター等を用いて好気条件下で反応を行ってもよい。好気条件下に保つために、例えば、反応液に酸素又は空気をバブリング等により通気する、プロペラ撹拌機を使用して反応液を撹拌する等の方法を用いることができる。通気又は撹拌は、溶存酸素濃度に応じて間欠的に、又は連続的に行うことができる。上記緩衝液のpHは、アルカリ性であってよく、pH7〜12、pH8〜11又はpH10.1〜10.3の範囲内にあってよい。 Also, there is no particular limitation on the specific operation method when producing ketooctadecadienoic acid using the above-mentioned raw materials, enzyme materials and metals. For example, a raw material, an enzyme material, and a metal may be added to a buffer solution, and the reaction may be performed under aerobic conditions using a jar fermenter or the like. In order to maintain the aerobic condition, for example, oxygen or air can be bubbled through the reaction solution, or the reaction solution can be stirred using a propeller stirrer. Aeration or stirring can be performed intermittently or continuously depending on the dissolved oxygen concentration. The pH of the buffer solution may be alkaline and may be in the range of pH 7-12, pH 8-11 or pH 10.1-10.3.
本実施形態に係るケトオクタデカジエン酸の製造方法においては、本発明による効果を阻害しない限りにおいて、上述した原料、酵素材料及び金属以外の成分を反応液に含んでいてもよい。具体的には、例えば、水、食塩、アルコール類、糖類(グルコース、マルトース等)、ミネラル(カルシウム、マグネシウム等及びこれらの塩類など)、乳化剤(グリセリン脂肪酸エステル、酢酸モノグリセリド、乳酸モノグリセリド、クエン酸モノグリセリド、ジアセチル酒石酸モノグリセリド、コハク酸モノグリセリド、ポリグリセリン脂肪酸エステル、ポリグリセリン縮合リノシール酸エステル、キラヤ抽出物、大豆サポニン、チャ種子サポニン、ショ糖脂肪酸エステル、植物レシチン、卵黄レシチン等)、pH調整剤(水酸化ナトリウム、水酸化カリウム、乳酸、クエン酸、酒石酸、リンゴ酸及び酢酸等)、緩衝液(炭酸ナトリウム、炭酸水素ナトリウム、ホウ酸、グリシン、塩化アンモニウム、アンモニア、水酸化ナトリウム、塩化カリウム等)、消泡剤、窒素源(小麦グルテン、大豆由来精製蛋白質、酵母エキス、ペプトン、アミノ酸、酵素分解調味液等)、食品加工用酵素(プロテアーゼ、ペプチダーゼ、セルラーゼ等)を挙げることができる。 In the method for producing ketooctadecadienoic acid according to the present embodiment, components other than the raw materials, enzyme materials and metals described above may be included in the reaction solution as long as the effects of the present invention are not impaired. Specifically, for example, water, salt, alcohols, sugars (glucose, maltose, etc.), minerals (calcium, magnesium, etc. and salts thereof), emulsifiers (glycerin fatty acid ester, acetic acid monoglyceride, lactic acid monoglyceride, citric acid monoglyceride) , Diacetyltartaric acid monoglyceride, succinic acid monoglyceride, polyglycerin fatty acid ester, polyglycerin condensed linosyl acid ester, kiraya extract, soybean saponin, tea seed saponin, sucrose fatty acid ester, plant lecithin, egg yolk lecithin, etc., pH adjuster (water Sodium oxide, potassium hydroxide, lactic acid, citric acid, tartaric acid, malic acid and acetic acid), buffer solution (sodium carbonate, sodium bicarbonate, boric acid, glycine, ammonium chloride, ammonia, sodium hydroxide, salt) Potassium, etc.), antifoaming agents, nitrogen sources (wheat gluten, soybean-derived purified protein, yeast extract, peptone, amino acids, enzyme-degraded seasoning liquid, etc.), food processing enzymes (protease, peptidase, cellulase, etc.) .
また、上述したリノール酸を含む原料として、食用油又はその加工物を用いた場合等、当該原料において、リノール酸のエステル体が含まれる場合、あらかじめリノール酸のエステル体にエステラーゼを作用させる工程をさらに備えていてもよい。エステラーゼとしては、リパーゼ、クロロゲン酸エステラーゼ、フィターゼ、ホスホリラーゼ、ホスホリパーゼ等が例示できる。リノール酸のエステル体を効率的にリノール酸に変換する観点から、エステラーゼはリパーゼであってもよい。リパーゼとしては市販のものを用いることができ、例えば、リパーゼMY、リパーゼOF、リパーゼPL、リパーゼQLM、ホスホリパーゼD(いずれも名糖産業社製)、ニューラーゼF、リパーゼA「アマノ」6、リパーゼAY「アマノ」30SD、リパーゼG「アマノ」50、リパーゼR「アマノ」、リパーゼDF「アマノ」15、リパーゼMER「アマノ」(いずれも天野エンザイム社製)を用いることができる。また、エステラーゼは、精製酵素を用いて供給されてもよく、麹菌、ペニシリウム属の糸状菌等から供給されてもよい。 In addition, when edible oil or processed product thereof is used as a raw material containing linoleic acid as described above, when the raw material contains an ester of linoleic acid, a step of causing esterase to act on the ester of linoleic acid in advance Furthermore, you may provide. Examples of esterases include lipases, chlorogenic acid esterases, phytases, phosphorylases, phospholipases, and the like. From the viewpoint of efficiently converting an ester of linoleic acid into linoleic acid, the esterase may be a lipase. As the lipase, commercially available products can be used. For example, lipase MY, lipase OF, lipase PL, lipase QLM, phospholipase D (all manufactured by Meika Sangyo Co., Ltd.), Neulase F, lipase A “Amano” 6, lipase AY “Amano” 30SD, lipase G “Amano” 50, lipase R “Amano”, lipase DF “Amano” 15 and lipase MER “Amano” (all manufactured by Amano Enzyme) may be used. The esterase may be supplied using a purified enzyme, or may be supplied from Aspergillus or Penicillium fungi.
上述した本実施形態に係るケトオクタデカジエン酸の製造方法により製造された、ケトオクタデカジエン酸の反応液中の含有量は、常法により測定することができる。例えば、当該反応液を凍結乾燥した後、有機溶媒(例えば、クロロホルム、メタノール等)で抽出し、LC−MS/MS分析により定量する方法等が挙げられる。 The content in the reaction solution of ketooctadecadienoic acid produced by the method for producing ketooctadecadienoic acid according to this embodiment described above can be measured by a conventional method. For example, the reaction solution is freeze-dried, extracted with an organic solvent (eg, chloroform, methanol, etc.), and quantified by LC-MS / MS analysis.
上記本実施形態に係るケトオクタデカジエン酸の製造方法は、上記反応液からケトオクタデカジエン酸を精製する工程をさらに備えていてもよい。ケトオクタデカジエン酸の精製は、公知の方法により行うことができる。例えば、溶媒抽出後に分離精製を行うことができる。溶媒としては、メタノール、エタノール等のアルコール類;n−ヘキサン、アセトン、酢酸エチル、酢酸メチル、及び超臨界二酸化炭素などを用いることができる。抽出は、物理的な撹拌・破砕、固液抽出、超音波処理、還流による抽出、浸漬、浸出、煎出、マイクロ波処理等の公知の方法により行うことができる。溶媒を処理したものをそのまま使用することも可能であるが、さらに活性炭処理、クロマトグラフィー、液液分配、蒸留、ゲル濾過、精密濾過等により精製してもよい。また、反応物を濾過・圧搾し、得られた濾液を静置又は遠心分離することにより、浮遊してくる油分を回収することにより分離を行ってもよい。さらに、反応液のpHを酸性化させてから、遠心分離により回収してもよい。または、反応液にカルシウム塩等を加えて金属石鹸化した後に、適切な遠心分離作業、ろ布又は濾過により沈殿物として回収してもよい。これらの作業により、ケトオクタデカジエン酸を効率的に濃縮することができる。分離された油分からさらに上記の精製を行ってもよい。 The method for producing ketooctadecadienoic acid according to the present embodiment may further include a step of purifying ketooctadecadienoic acid from the reaction solution. Purification of ketooctadecadienoic acid can be performed by a known method. For example, separation and purification can be performed after solvent extraction. As the solvent, alcohols such as methanol and ethanol; n-hexane, acetone, ethyl acetate, methyl acetate, supercritical carbon dioxide, and the like can be used. The extraction can be performed by a known method such as physical stirring / crushing, solid-liquid extraction, ultrasonic treatment, extraction by reflux, immersion, leaching, decoction, microwave treatment, and the like. The solvent-treated one can be used as it is, but may be further purified by activated carbon treatment, chromatography, liquid-liquid distribution, distillation, gel filtration, microfiltration, or the like. Moreover, you may isolate | separate by collect | recovering the oil which floats by filtering and squeezing a reaction material and standing or centrifuging the obtained filtrate. Furthermore, the pH of the reaction solution may be acidified and then recovered by centrifugation. Or after adding calcium salt etc. to a reaction liquid and making it metal soap, you may collect | recover as precipitation by suitable centrifugation operation | work, a filter cloth, or filtration. By these operations, ketooctadecadienoic acid can be efficiently concentrated. You may perform said refinement | purification further from the isolate | separated oil.
本実施形態に係る製造方法により製造されたケトオクタデカジエン酸は、PPARα活性化能を有するため、例えば、糖尿病、肥満、脂質代謝異常症、インスリン抵抗性、高脂血症、動脈硬化及び冠動脈疾患の予防又は改善に用いることができる。 Since ketooctadecadienoic acid produced by the production method according to the present embodiment has PPARα activation ability, for example, diabetes, obesity, dyslipidemia, insulin resistance, hyperlipidemia, arteriosclerosis and coronary artery It can be used for prevention or amelioration of diseases.
また、所望により上述した精製方法に従って精製した後、例えば食品、機能性食品等に添加して用いることができる。また、当該製造方法において、食品、機能性食品等に添加してもよい成分を用いて製造された場合には、反応液をそのまま食品、機能性食品等として、又は反応液をそのまま食品、機能性食品等に含ませて利用することができる。 Moreover, after refine | purifying according to the refinement | purification method mentioned above if desired, it can add and use, for example to a foodstuff, a functional foodstuff, etc. In addition, in the production method, when manufactured using ingredients that may be added to food, functional food, etc., the reaction solution is used as it is as food, functional food, etc., or the reaction solution is used as it is as food, function food, etc. It can be used by including it in a sex food.
このような食品、機能性食品としては、例えば、味噌、諸味風調味料、しょう油、しょう油加工品、みりん、つゆ、たれ、和風だし、洋風だし、中華だし、ドレッシング、ケチャップ、トマトソース、パスタソース、ウスターソース及びその他ソース等の調味料、パン類、ケーキ・菓子類、麺類、ゼリー類、冷凍食品、レトルト食品、フリーズドライ食品、アイスクリーム類、乳製品、スープ類、豆腐よう、乳発酵食品、豆乳発酵食品、大豆発酵食品等の各種加工食品のほか、サプリメントの形態として、タブレット錠、錠剤、顆粒、カプセル剤、シロップ剤等が挙げられる。飲料としては、例えば、豆乳、果汁飲料、炭酸飲料、茶系飲料、ニアウォーター、スポーツ飲料、乳飲料、アルコール飲料、清涼飲料等が挙げられる。食用油としては、調理用油、マヨネーズ、マーガリン等の油脂加工品類等が挙げられる。 Examples of such foods and functional foods include miso, moromi-flavored seasoning, soy sauce, soy sauce processed products, mirin, soy sauce, sauce, Japanese-style dashi, Western-style dashi, Chinese dashi, dressing, ketchup, tomato sauce, pasta sauce Seasonings such as Worcester sauce and other sauces, breads, cakes / confectionery, noodles, jelly, frozen foods, retort foods, freeze-dried foods, ice creams, dairy products, soups, tofu, fermented milk products, In addition to various processed foods such as fermented soymilk and fermented soybeans, examples of supplements include tablets, tablets, granules, capsules, and syrups. Examples of the beverage include soy milk, fruit juice beverage, carbonated beverage, tea beverage, near water, sports beverage, milk beverage, alcoholic beverage, and soft drink. Examples of edible oils include cooking oils, mayonnaise, margarine and other processed oils and fats.
以下、実施例に基づき、本発明をより具体的に説明する。しかしながら、本発明は以下の実施例に限定されるものではない。なお、反応液におけるケトオクタデカジエン酸の定量及び反応液の官能評価は、以下の手順に従って実施した。 Hereinafter, based on an Example, this invention is demonstrated more concretely. However, the present invention is not limited to the following examples. The determination of ketooctadecadienoic acid in the reaction solution and the sensory evaluation of the reaction solution were performed according to the following procedure.
[ケトオクタデカジエン酸の定量]
ケトオクタデカジエン酸のLC−MS/MS分析は、以下の条件で行った。
LC条件:
移動相A;水(0.1%ギ酸を含む)
移動相B;アセトニトリル(0.1%ギ酸を含む)
グラジエント条件;移動相A50%(0分)−80%(14分)−99%(17〜18分)−50%(19分)
カラム温度;50℃
カラム;YMC−Triart C18(100×2.0mm、1.9m)
流速;0.3mL/分
インジェクション量;5μL
分析時間;38分
[Quantitative determination of ketooctadecadienoic acid]
LC-MS / MS analysis of ketooctadecadienoic acid was performed under the following conditions.
LC conditions:
Mobile phase A; water (containing 0.1% formic acid)
Mobile phase B; acetonitrile (containing 0.1% formic acid)
Gradient conditions: Mobile phase A 50% (0 minutes) -80% (14 minutes) -99% (17-18 minutes) -50% (19 minutes)
Column temperature: 50 ° C
Column; YMC-Triart C18 (100 × 2.0 mm, 1.9 m)
Flow rate; 0.3 mL / min injection volume; 5 μL
Analysis time: 38 minutes
MS条件:
Scans in Period;1069
Relative Start Time;1100.00msec
Scan Type;MRM
Polarity;Negative
MS conditions:
Scans in Period; 1069
Relative Start Time; 1100.00 msec
Scan Type; MRM
Polarity; Negative
MRM条件:
・13−oxo−ODA
Q1mass;293.30
Q3mass;113.00
Dwell(msec);500.00
・9−oxo−ODA
Q1mass;293.10
Q3mass;185.20
Dwell(msec);500.00
MRM conditions:
・ 13-oxo-ODA
Q1 mass; 293.30
Q3mass; 113.00
Dwell (msec); 500.00
・ 9-oxo-ODA
Q1 mass; 293.10
Q3 mass; 185.20
Dwell (msec); 500.00
[官能評価]
製造した反応液について、熟練したパネル5名による香りの官能評価を実施した。官能評価の基準を以下に示す。官能評価がA又はBであれば、酸化劣化臭が少なく、副生成物が抑制されていると評価することができる。
(油の酸化劣化臭)
A:油の酸化劣化臭がわずかであるか、ほとんど感じられない。
B:油の酸化劣化臭が弱い。
C:油の酸化劣化臭がやや強い。
D:油の酸化劣化臭が強い。
[sensory evaluation]
About the manufactured reaction liquid, sensory evaluation of the fragrance by five skilled panels was implemented. The criteria for sensory evaluation are shown below. If sensory evaluation is A or B, it can be evaluated that there are few oxidation degradation odors and the by-product is suppressed.
(Oxidative degradation odor of oil)
A: The oxidative degradation odor of the oil is slight or hardly felt.
B: The oxidative degradation odor of oil is weak.
C: The oxidative degradation odor of oil is slightly strong.
D: The oxidative degradation odor of oil is strong.
<実施例1〜3及び比較例1〜3>
0.2M炭酸ナトリウム溶液及び0.2M炭酸水素ナトリウム溶液を7:3(v:v)となるように混合し、pHが10.2の緩衝液(炭酸ナトリウム/炭酸水素ナトリウム緩衝液)を調製した。大豆粉末として生大豆(国産、フクユタカ)をミキサーで破砕し粉末化したものを用いた。破砕の際は、熱の発生を抑制するため、温度上昇に注意しながら間欠的に破砕した。緩衝液1L、大豆粉末20g、及びリノール酸(和光純薬社製、特級試薬)28gを、2.5Lミニジャーファーメンターに仕込み、5℃の温度条件で3時間通気攪拌を行った。その後、実施例1〜3及び比較例1〜2では、マンガン含有酵母を10g(1%w/v;セティ社販売品、マンガン5%含有)添加し、下記表1に示した温度及び反応時間にて通気攪拌を行った。比較例3ではマンガン含有酵母を添加せずに、下記表1に示した温度及び反応時間にて通気攪拌を行った。反応液中に生成した13−oxo−ODAの含有量及び官能評価の結果を表1に示す。
<Examples 1-3 and Comparative Examples 1-3>
A 0.2M sodium carbonate solution and a 0.2M sodium hydrogen carbonate solution are mixed so as to be 7: 3 (v: v) to prepare a buffer solution (sodium carbonate / sodium bicarbonate buffer solution) having a pH of 10.2. did. As soybean powder, raw soybean (domestic, Fukuyutaka) crushed with a mixer and powdered was used. In crushing, in order to suppress the generation of heat, crushing intermittently while paying attention to the temperature rise. 1 L of buffer solution, 20 g of soybean powder, and 28 g of linoleic acid (special grade reagent, manufactured by Wako Pure Chemical Industries, Ltd.) were charged into a 2.5 L mini jar fermenter and aerated and stirred for 3 hours at a temperature of 5 ° C. Thereafter, in Examples 1 to 3 and Comparative Examples 1 to 2, 10 g of manganese-containing yeast (1% w / v; a product sold by Seti, containing 5% manganese) was added, and the temperatures and reaction times shown in Table 1 below were added. Aeration stirring was carried out. In Comparative Example 3, aeration and agitation were performed at the temperatures and reaction times shown in Table 1 below without adding manganese-containing yeast. Table 1 shows the content of 13-oxo-ODA produced in the reaction solution and the results of sensory evaluation.
<実施例4〜6>
0.2M炭酸ナトリウム溶液及び0.2M炭酸水素ナトリウム溶液を7:3(v:v)となるように混合し、pHが10.2の緩衝液(炭酸ナトリウム/炭酸水素ナトリウム緩衝液)を調製した。大豆粉末として生大豆(国産、フクユタカ)をミキサーで破砕し粉末化したものを用いた。破砕の際は、熱の発生を抑制するため、温度上昇に注意しながら間欠的に破砕した。緩衝液1L、大豆粉末20g、及びリノール酸(和光純薬社製、特級試薬)28gを、2.5Lミニジャーファーメンターに仕込み、5℃の温度条件で、実施例4及び5については3時間通気攪拌を行い、実施例6については4時間通気攪拌を行った。その後、実施例4ではマンガン含有酵母を10g(1%w/v)添加し、実施例5では亜鉛含有酵母10g(1%w/v;メディエンス社販売品、亜鉛10%含有)を添加し、実施例6では鉄含有酵母10g(1%w/v;セティ社販売品、鉄5%含有)を添加し、下記表2に示した温度及び反応時間にて通気攪拌を行った。反応液中に生成した13−oxo−ODA及び9−oxo−ODAの含有量及び官能評価の結果を表2に示す。
<Examples 4 to 6>
A 0.2M sodium carbonate solution and a 0.2M sodium hydrogen carbonate solution are mixed so as to be 7: 3 (v: v) to prepare a buffer solution (sodium carbonate / sodium bicarbonate buffer solution) having a pH of 10.2. did. As soybean powder, raw soybean (domestic, Fukuyutaka) crushed with a mixer and powdered was used. In crushing, in order to suppress the generation of heat, crushing intermittently while paying attention to the temperature rise. 1 L of buffer solution, 20 g of soybean powder, and 28 g of linoleic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) were charged into a 2.5 L mini-jar fermenter, and the temperature conditions of 5 ° C. were used for Examples 4 and 5 for 3 hours. Aeration agitation was performed, and Example 6 was agitated for 4 hours. Thereafter, 10 g (1% w / v) of manganese-containing yeast was added in Example 4, and 10 g of zinc-containing yeast (1% w / v; a product sold by Medience, Inc. containing 10% zinc) was added in Example 5. In Example 6, 10 g of iron-containing yeast (1% w / v; sold by Setty, containing 5% iron) was added, and aeration and stirring were performed at the temperatures and reaction times shown in Table 2 below. Table 2 shows the contents of 13-oxo-ODA and 9-oxo-ODA produced in the reaction solution and the results of sensory evaluation.
<実施例7〜12>
0.2M炭酸ナトリウム溶液及び0.2M炭酸水素ナトリウム溶液を7:3(v:v)となるように混合し、pHが10.2の緩衝液(炭酸ナトリウム/炭酸水素ナトリウム緩衝液)を調製した。大豆粉末として生大豆(国産、フクユタカ)をミキサーで破砕し粉末化したものを用いた。破砕の際は、熱の発生を抑制するため、温度上昇に注意しながら間欠的に破砕した。水0.5L、リパーゼ(リパーゼOF、名糖産業社製)0.15g、及び大豆油(大豆白絞油、昭和産業社製)を、2.5Lミニジャーファーメンターに仕込み、43〜48℃の温度条件で攪拌しながら24時間リパーゼ反応を行った。その後、5℃まで冷却し、実施例7及び8では大豆粉末添加後、3時間の反応を行った。リパーゼ反応後のpHはそれぞれ、pH7.5、pH7.6であった。実施例9〜12では大豆粉末添加後、1VVM(volume per volume per minute:1分間に供給する培地1L当たりの通気量)にて6時間の反応を行った。下記表3に示す金属又は金属酵母を添加し、表3に示した温度及び反応時間にて通気攪拌を行った。反応液中に生成した13−oxo−ODA及び9−oxo−ODAの含有量及び官能評価の結果を表3に示す。なお、硫酸マンガン一水和物は、和光純薬社製のものを用いた。硫酸鉄は、関東化学社製の食品添加物を用いた。
<Examples 7 to 12>
A 0.2M sodium carbonate solution and a 0.2M sodium hydrogen carbonate solution are mixed so as to be 7: 3 (v: v) to prepare a buffer solution (sodium carbonate / sodium bicarbonate buffer solution) having a pH of 10.2. did. As soybean powder, raw soybean (domestic, Fukuyutaka) crushed with a mixer and powdered was used. In crushing, in order to suppress the generation of heat, crushing intermittently while paying attention to the temperature rise. Water 0.5L, lipase (lipase OF, manufactured by Meika Sangyo Co., Ltd.) 0.15 g, and soybean oil (soybean white squeezed oil, manufactured by Showa Sangyo Co., Ltd.) were charged into a 2.5 L mini jar fermenter, 43-48 ° C. The lipase reaction was carried out for 24 hours while stirring under the following temperature conditions. Then, it cooled to 5 degreeC, and reaction was performed for 3 hours after soybean powder addition in Example 7 and 8. The pH after the lipase reaction was pH 7.5 and pH 7.6, respectively. In Examples 9 to 12, after adding soybean powder, a reaction was performed for 6 hours at 1 VVM (volume per volume per minute: aeration volume per 1 L of medium supplied per minute). Metals or metal yeasts shown in Table 3 below were added, and aeration and stirring were performed at the temperatures and reaction times shown in Table 3. Table 3 shows the contents of 13-oxo-ODA and 9-oxo-ODA produced in the reaction solution and the results of sensory evaluation. Manganese sulfate monohydrate was manufactured by Wako Pure Chemical Industries. As the iron sulfate, a food additive manufactured by Kanto Chemical Co., Inc. was used.
本発明に係る製造方法によれば、反応液の酸化劣化臭が少ないことから、副生成物が抑制されており、且つケトオクタデカジエン酸を効率的に製造することができる。一方、反応温度を20℃以上とした場合には、ケトオクタデカジエン酸の生成量が減少するとともに、やや強い酸化劣化臭が確認され、副生成物が製造されていることが示唆された。なお、反応液中に金属を添加しなかった場合には、ケトオクタデカジエン酸はほとんど生成されなかった。 According to the production method of the present invention, since the reaction solution has less oxidative degradation odor, by-products are suppressed and ketooctadecadienoic acid can be produced efficiently. On the other hand, when the reaction temperature was 20 ° C. or higher, the amount of ketooctadecadienoic acid produced decreased, and a slightly strong oxidative degradation odor was confirmed, suggesting that a by-product was produced. When no metal was added to the reaction solution, ketooctadecadienoic acid was hardly generated.
Claims (13)
The production method according to claim 12, wherein the esterase is lipase.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015062418A JP6558925B2 (en) | 2015-03-25 | 2015-03-25 | Method for producing ketooctadecadienoic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015062418A JP6558925B2 (en) | 2015-03-25 | 2015-03-25 | Method for producing ketooctadecadienoic acid |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016178913A true JP2016178913A (en) | 2016-10-13 |
JP6558925B2 JP6558925B2 (en) | 2019-08-14 |
Family
ID=57130711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015062418A Active JP6558925B2 (en) | 2015-03-25 | 2015-03-25 | Method for producing ketooctadecadienoic acid |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6558925B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113632978A (en) * | 2021-07-12 | 2021-11-12 | 宮本哲也 | PPAR action substance and method for producing the same |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040029225A1 (en) * | 2000-09-05 | 2004-02-12 | Akiko Sugio | Lipoxygenase |
WO2007110907A1 (en) * | 2006-03-27 | 2007-10-04 | Stc System Japan Co., Ltd | Method of improving the taste and texture of soybean protein-glucomannan coagulation and enabling long-time storage thereof |
JP2008054694A (en) * | 2007-11-19 | 2008-03-13 | Ajinomoto Co Inc | Mineral fortified liquid food mixed with yeast |
WO2014088002A1 (en) * | 2012-12-03 | 2014-06-12 | キッコーマン株式会社 | Method for producing ketooctadecadienoic acid |
-
2015
- 2015-03-25 JP JP2015062418A patent/JP6558925B2/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040029225A1 (en) * | 2000-09-05 | 2004-02-12 | Akiko Sugio | Lipoxygenase |
JP2004508039A (en) * | 2000-09-05 | 2004-03-18 | ノボザイムス アクティーゼルスカブ | Lipoxygenase |
WO2007110907A1 (en) * | 2006-03-27 | 2007-10-04 | Stc System Japan Co., Ltd | Method of improving the taste and texture of soybean protein-glucomannan coagulation and enabling long-time storage thereof |
JP2008054694A (en) * | 2007-11-19 | 2008-03-13 | Ajinomoto Co Inc | Mineral fortified liquid food mixed with yeast |
WO2014088002A1 (en) * | 2012-12-03 | 2014-06-12 | キッコーマン株式会社 | Method for producing ketooctadecadienoic acid |
Non-Patent Citations (2)
Title |
---|
ABCシリーズ 酵素−バイオテクノロジーへの指針−I, JPN6019005508, 20 March 1985 (1985-03-20), pages 164, ISSN: 0003979715 * |
酵素ハンドブック, JPN6019005507, 1 December 1982 (1982-12-01), pages 165, ISSN: 0003979714 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113632978A (en) * | 2021-07-12 | 2021-11-12 | 宮本哲也 | PPAR action substance and method for producing the same |
Also Published As
Publication number | Publication date |
---|---|
JP6558925B2 (en) | 2019-08-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6008983B2 (en) | Method for producing ketooctadecadienoic acid | |
ES2550468T3 (en) | Method of producing fat or microbial oil that has a low content of non-saponifiable matter and said fat or oil | |
EP2958982B1 (en) | Methods of recovering oil from microorganisms | |
EP1801226B1 (en) | Arachidonic acid and methods for the production and use thereof | |
Ahmad et al. | A review on mycoprotein: History, nutritional composition, production methods, and health benefits | |
JP4522257B2 (en) | Process for producing transesterified oil or fat or triglyceride | |
CN105829539B (en) | Method for recovering oil from microorganisms | |
CN1792235A (en) | Nutrient flavouring made from fresh water fish protein, and its prodn. method | |
WO2006022356A1 (en) | Process for producing microorganism fat containing diacylglycerol in any amount and the fat | |
WO1998039468A1 (en) | Process for preparing highly unsaturated fatty acid and lipid containing highly unsaturated fatty acid | |
CN103981009A (en) | Method for extracting intracellular grease by wall breaking of schizochytrium limacinum fermentation broth | |
Lee et al. | Omega-3 fatty acids concentrate production by enzyme-catalyzed ethanolysis of supercritical CO 2 extracted oyster oil | |
JP4596475B2 (en) | Taste improving agent | |
JP6558925B2 (en) | Method for producing ketooctadecadienoic acid | |
JP4297604B2 (en) | seasoning | |
JPWO2015029966A1 (en) | Method for producing ω3 unsaturated fatty acid enzyme and eicosapentaenoic acid | |
JP7218023B1 (en) | Method for producing dried food containing dried alga bodies, method for producing food, and method for improving flavor of heterotrophic microalgae | |
JP2019129795A (en) | Flavor improver | |
JP2008048686A (en) | Soybean processed food | |
WO2016031947A1 (en) | Method of producing lipids with high eicosapentaenoic acid content | |
JP5725598B2 (en) | Method for producing antioxidant composition | |
JP7262536B2 (en) | Lipid composition, use thereof and method for producing the same | |
JP5578644B2 (en) | Method for producing sesame vinegar and sesame vinegar | |
JP6026709B1 (en) | Process for producing novel ω3 unsaturated fatty acid enzyme and eicosapentaenoic acid | |
CN117980492A (en) | Recycling food residues by microbial fermentation |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20171004 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20180718 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180807 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180926 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20190219 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190513 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20190521 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190709 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190716 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6558925 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |