JPH0634730B2 - Method for producing palmitoleic acid - Google Patents
Method for producing palmitoleic acidInfo
- Publication number
- JPH0634730B2 JPH0634730B2 JP61139902A JP13990286A JPH0634730B2 JP H0634730 B2 JPH0634730 B2 JP H0634730B2 JP 61139902 A JP61139902 A JP 61139902A JP 13990286 A JP13990286 A JP 13990286A JP H0634730 B2 JPH0634730 B2 JP H0634730B2
- Authority
- JP
- Japan
- Prior art keywords
- poa
- acid
- yeast
- purity
- palmitoleic 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.)
- Expired - Lifetime
Links
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 235000021319 Palmitoleic acid Nutrition 0.000 title claims description 5
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 title claims description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 210000005253 yeast cell Anatomy 0.000 claims description 6
- 239000006285 cell suspension Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000000356 contaminant Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000005227 gel permeation chromatography Methods 0.000 claims 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 13
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000000605 extraction Methods 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000002632 lipids Chemical class 0.000 description 9
- 229930182558 Sterol Natural products 0.000 description 7
- 235000003702 sterols Nutrition 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- 150000003432 sterols Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 230000000813 microbial effect Effects 0.000 description 4
- -1 sterol ester Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 3
- 235000017471 coenzyme Q10 Nutrition 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 3
- 229940035936 ubiquinone Drugs 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 241000235070 Saccharomyces Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 241000555825 Clupeidae Species 0.000 description 1
- 241000235646 Cyberlindnera jadinii Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes 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
- 206010020772 Hypertension Diseases 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 241000208467 Macadamia Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000223252 Rhodotorula Species 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 235000003534 Saccharomyces carlsbergensis Nutrition 0.000 description 1
- 241001123227 Saccharomyces pastorianus Species 0.000 description 1
- 241000582914 Saccharomyces uvarum Species 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- 241000235033 Zygosaccharomyces rouxii Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate 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
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 229940057059 monascus purpureus Drugs 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000012138 yeast extract 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
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 パルミトレイン酸(以下、POAと略す)は、広く生物
界に存在する不飽和脂肪酸の一つで、従来、抗腫瘍剤、
虫歯菌抑制、健康老化との関係、さらに化粧品分野利
用、また最近では高血圧性疾患における血管障害を防護
する作用(特開昭59-175425)等が報告され、優れた薬
理作用、生理作用を示すことが明らかにされ、今後広く
化粧品、医薬品用途への開発が期待される。DETAILED DESCRIPTION OF THE INVENTION [Industrial field of application] Palmitoleic acid (hereinafter abbreviated as POA) is one of unsaturated fatty acids widely existing in the living world.
Inhibition of dental caries, relationship with health aging, use in the field of cosmetics, and recently the effect of protecting vascular disorders in hypertensive diseases (Japanese Patent Laid-Open No. 59-175425), etc. have been reported, showing excellent pharmacological and physiological effects. It has been clarified that it is expected to be widely applied to cosmetics and pharmaceuticals in the future.
POAの工業的方法としては、マカダミアナッツ・米ぬ
か等の植物、鯨・いわし等の魚油からの抽出法によるP
OAを含有するオイル等が知られているが、高純度化す
る精製技術については殆ど知られていない。一般的に植
物からの抽出精製法としては、圧搾法等にて得られた脂
質成分を、アルカリによるケン化処理、あるいはリパー
ゼによる酵素分解処理を行ない、遊離した脂肪酸類の中
から、分子蒸留法・向流分配法・クロマトグラフ法等に
より、目的物質を精製単離する方法が知られている。一
方、酵母等微生物によるPOA発酵生産法については、
まったく知られてなく、種属間また培養諸条件下での菌
体脂質成分としての脂肪酸組成、膜構成及び機能につい
ての研究報告が以下のように多数有るのみである。すな
わち、S.cerevisiaeにおいて、培養温度のPOA含量に
及ぼす影響〔Biochem.Biophys.Acta.260、639
(1972)〕、〔J.Biol.Chem.254、12281
(1979)〕、嫌気、好気培養条件下でのPOA含量
の推移〔J.Brew.Soc.Japan.72、735(197
7)〕、〔J.Cell.Biol.37、221(1968)〕
〔Arch.Microbiol.66、34(1969)〕、〔Arch.
Microbiol.117、239(1978)〕、細胞質膜及
び細胞壁の脂肪酸組成〔Chem.Phys.Lipids.4、247
(1970)〕、脂肪酸組成と機能との関係〔Antonie
van Leeuwenhoek.38、129(1972)〕、〔Exp.
Mycol.8、55(1984)〕、細胞膜脂質組成とEEtO
H耐性の関係〔J.Inst.Brew.82、218(197
6)〕、またS.uvarumにおいて嫌気、好気培養条件下で
の脂質組成〔J.Inst.Brew.88、367(198
2)〕、(Pro.Con-Eur.Brew.18、285(198
1)〕、培養温度のPOA含量に及ぼす影響〔ASBC
J.40、26(1982)〕、脂肪酸組成に対する
チアミンピリドキシンの影響〔Biochem.Biophys.Res.Co
mmun.59、777(1974)〕さらにS.rouxiiにお
いて脂肪酸組成〔農化46、657(1972)〕等が
報告されているが、POAを含む脂肪酸抽出法として
は、クロロホルム・メタノール混液抽出、メタノール・
アルカリ前処理後、エーテル抽出等であり、抽出した脂
質成分をケン化処理メチルエステル化し、ガスクロマト
グラフィー分析する方法であり、酵母等微生物菌体中か
ら工業的レベルでのPOA単離方法については、まった
く報告されていない。As an industrial method of POA, P by extraction method from plants such as macadamia nuts and rice bran and fish oil such as whales and sardines
Although oils and the like containing OA are known, little is known about purification techniques for high purification. In general, as a method for extracting and purifying from a plant, a lipid component obtained by a squeezing method or the like is subjected to saponification treatment with an alkali or enzymatic decomposition treatment with a lipase, and the fatty acids released are subjected to a molecular distillation method. -Methods for purifying and isolating a target substance by a countercurrent distribution method, a chromatographic method, etc. are known. On the other hand, regarding the POA fermentation production method using microorganisms such as yeast,
It is not known at all, and there are only a large number of research reports on fatty acid composition, membrane constitution and function as bacterial lipid components under the conditions of various species and various culture conditions as follows. That is, in S. cerevisiae, the influence of the culture temperature on the POA content [Biochem. Biophys. Acta. 260 , 639
(1972)], [J. Biol. Chem. 254 , 12281.
(1979)], transition of POA content under anaerobic and aerobic culture conditions [J. Brew. Soc. Japan. 72 , 735 (197).
7)], [J. Cell. Biol. 37 , 221 (1968)].
[Arch. Microbiol. 66 , 34 (1969)], [Arch.
Microbiol. 117 , 239 (1978)], fatty acid composition of cytoplasmic membrane and cell wall [Chem. Phys. Lipids. 4 , 247].
(1970)], relationship between fatty acid composition and function [Antonie
van Leeuwenhoek. 38 , 129 (1972)], [Exp.
Mycol. 8 , 55 (1984)], cell membrane lipid composition and EEtO.
Relationship between H resistance [J. Inst. Brew. 82 , 218 (197)
6)], and lipid composition under anaerobic and aerobic culture conditions in S. uvarum [J. Inst. Brew. 88 , 367 (198).
2)], (Pro.Con-Eur.Brew. 18 , 285 (198)
1)], Effect of culture temperature on POA content [ASBC
J. 40 , 26 (1982)], Effect of thiamine pyridoxine on fatty acid composition [Biochem. Biophys. Res. Co.
mmun. 59 , 777 (1974)] Furthermore, fatty acid composition [Agricultural 46 , 657 (1972)] and the like have been reported in S. rouxii. As a fatty acid extraction method containing POA, chloroform / methanol mixture extraction, methanol・
After the alkali pretreatment, ether extraction or the like is performed, and the extracted lipid components are subjected to saponification methyl esterification and gas chromatographic analysis. Regarding the method for isolating POA from microbial cells such as yeast on an industrial level, , Not reported at all.
酵母等微生物菌体中に存在する脂肪酸は、遊離型として
はほとんど無く、トリグリセライド、ステロールエステ
ル、複合脂質としてのエステル結合型である。そこで微
生物菌体の破壊さらにエステル結合の加水分解すなわち
ケン化処理を予め行ない、その時に副生するグリセリン
等の共雑物を水層に除去して、POAを含む遊離型脂肪
酸を溶剤抽出した後、さらに精製処理を行なう方法を完
成させることにより、高純度POAを微生物菌体から工
業的レベルで生産可能となるとともに、天然物由来と比
較して、安価かつ容易に供給でき、広く化粧品、医薬品
用途等に活用できるものとなる。Fatty acids existing in microbial cells such as yeast are almost in free form, but are in triglyceride, sterol ester, and ester bond type as complex lipid. Therefore, after microbial cell destruction and ester bond hydrolysis or saponification treatment are performed in advance, contaminants such as glycerin that are by-produced at that time are removed from the aqueous layer, and free fatty acids containing POA are extracted with a solvent. By completing the method of further purification treatment, high-purity POA can be produced from microbial cells on an industrial level, and can be supplied cheaply and easily as compared with natural products, and widely used in cosmetics and pharmaceuticals. It can be used for various purposes.
本発明者らは、酵母菌体からのPOA抽出精製法につい
て鋭意検討した結果、予め酸性下で菌体を破壊し、次い
でケン化処理した後、酸性下にて単独あるいは二種以上
の水と混合しない溶剤でPOAを含む脂質成分を抽出分
離し、さらに晶析及びカラムクロマトグラフ法を行ない
高純度のPOAを製造する方法を見い出し、本発明を完
成するに到った。As a result of diligent studies on a method for extracting and purifying POA from yeast cells, the present inventors have previously destroyed the cells under acidic conditions and then subjected to saponification treatment, and then used alone or two or more kinds of water under acidic conditions. The present invention has been completed by finding a method of producing a high-purity POA by extracting and separating a lipid component containing POA with a solvent that does not mix, and further performing crystallization and column chromatography.
すなわち、POAを含有する酵母菌体の水懸濁液を予め
酸で加熱処理し、次いでアルカリ処理することにより菌
体破壊さらに中性脂肪、リン脂質、ステロールエステル
等の脂質成分を加水分解した後、酸性下でPOAを含む
遊離型脂肪酸を単独あるいは二種以上の水と混合しない
溶剤で抽出し、加水分解で副生したグリセリン、リン酸
化合物等の水可溶成分を水層に分離除去する。その後、
分離した溶剤層を減圧下で濃縮回収し、ステロール類・
ユビキノン等の共雑物を晶析及び順相ゲルカラムクロマ
トグラフ処理により除去し、さらに逆相ゲルクロマトグ
ラフ処理による精製を行ない、高純度のPOAを製造す
ることを見い出し本発明を完成した。以下、本発明を詳
細に説明する。That is, after the aqueous suspension of yeast cells containing POA is heat-treated with an acid in advance and then treated with an alkali, the cells are destroyed to further hydrolyze lipid components such as neutral fat, phospholipids and sterol esters. The free fatty acid containing POA is extracted under acidic conditions with a solvent that does not mix alone or with two or more kinds of water, and water-soluble components such as glycerin and phosphate compounds by-produced by hydrolysis are separated and removed into an aqueous layer. . afterwards,
The separated solvent layer is concentrated and recovered under reduced pressure, and sterols /
The present invention was completed by finding that high-purity POA was produced by removing contaminants such as ubiquinone by crystallization and normal phase gel column chromatographic treatment and further purifying by reverse phase gel chromatographic treatment. Hereinafter, the present invention will be described in detail.
本発明に用いるPOA含有酵母としては、POAを菌体
内に蓄積する能力を有するものであれば、いずれを用い
ることができる。代表的な例として、市販パン酵母、W
ine yeast IFO 2229、サッカロミセ
ス・セレビシェATCC 18790、同NCYC 3
66、また市販乾燥ビール酵母、またサッカロミセス・
カールスベルゲンシス(Saccharomyces carlsber′gens
is)ATCC9080、同NCYC 74、またサッカ
ロミセス・デルブリッキー(Saccharomyces delbruecki
i)NCYC 100、またキャンディダ・ユーティリ
ス(Candida utilis)IAM 4815、またロドトル
ラ・グルティリス(Rhodotorula glutilis)IFO 1
125を示すことができる。As the POA-containing yeast used in the present invention, any yeast can be used as long as it has the ability to accumulate POA in the cells. As a typical example, commercially available baker's yeast, W
ine yeast IFO 2229, Saccharomyces cerevisiae ATCC 18790, NCYC 3
66, also commercially available dry brewer's yeast, and Saccharomyces
Carlsbergensis (Saccharomyces carlsber'gens
is) ATCC 9080, NCYC 74, and Saccharomyces delbruecki
i) NCYC 100, Candida utilis IAM 4815, and Rhodotorula glutilis IFO 1
125 can be indicated.
その水懸濁液の濃度は乾燥重量で1〜30%、好ましく
は10〜20%で行なえば良い。酸処理の酸としては、
硫酸、塩酸、硝酸等が用いられ、通常始発pH2以下、加
熱温度60〜150℃、加熱時間0.5〜10時間、好ま
しくはpH1以下、温度80〜120℃、2〜6時間が最
適である。アルカリ処理は、水酸化アルカリ、炭酸アル
カリ等を加え、通常PH10以上、加熱温度60〜150
℃、加熱時間10分〜20時間、好ましくはPH13以
上、温度80〜120℃、10〜15時間が最適であ
る。中和用の酸として硫酸、塩酸、硝酸等を用いてアル
カリ処理液のPHを7.0以下、好ましくは1.0〜6.5に調整
する。抽出溶剤としては、n−ヘキサン、クロロホル
ム、イソオクタン、石油エーテル、ジクロルエタン、メ
チルイソブチルケトン、ブタノール、酢酸エチル等の水
と分離する有機溶剤が使用できる。この際、抽出溶剤と
ケン化処理液との分離を妨げない程度の量のメタノー
ル、エタノール、イソプロピルアルコール、アセトン等
の親水性溶剤と、二種以上混合した溶剤を使用しても良
い。The concentration of the aqueous suspension may be 1 to 30% by dry weight, preferably 10 to 20%. As the acid for acid treatment,
Sulfuric acid, hydrochloric acid, nitric acid and the like are used, and the initial pH is usually 2 or less, the heating temperature is 60 to 150 ° C., the heating time is 0.5 to 10 hours, preferably pH 1 or less, the temperature is 80 to 120 ° C., and 2 to 6 hours are optimum. The alkali treatment is carried out by adding alkali hydroxide, alkali carbonate, etc., usually at a pH of 10 or higher, and a heating temperature of 60 to 150.
C, heating time 10 minutes-20 hours, PH13 or more, temperature 80-120 degreeC, 10-15 hours are optimal. The pH of the alkaline treatment liquid is adjusted to 7.0 or less, preferably 1.0 to 6.5 using sulfuric acid, hydrochloric acid, nitric acid or the like as an acid for neutralization. As the extraction solvent, an organic solvent that separates from water, such as n-hexane, chloroform, isooctane, petroleum ether, dichloroethane, methyl isobutyl ketone, butanol, ethyl acetate can be used. At this time, a solvent prepared by mixing two or more kinds of hydrophilic solvents such as methanol, ethanol, isopropyl alcohol and acetone in an amount that does not hinder the separation of the extraction solvent and the saponification solution may be used.
抽出液は水洗後、脱水して、減圧下で濃縮した後、濃縮
物を少量のn−ヘキサンに溶かし、冷却して析出してく
るステロール類を除去した後、シリカゲル、アルミナ等
を使用する順相カラムクロマトグラス処理してユビキノ
ン・ステロール類等の共雑物を除去、さらにODSゲ
ル、HP樹脂等を使用する逆相カラムクロマトグラフ処
理を行ない、混在するパルミチン酸、オレイン酸等の脂
肪酸を分画除去することにより高純度のPOAを得るこ
とができる。The extract is washed with water, dehydrated, concentrated under reduced pressure, the concentrate is dissolved in a small amount of n-hexane, cooled to remove precipitated sterols, and then silica gel, alumina, etc. are used in this order. -Phase column chromatograss treatment removes contaminants such as ubiquinone and sterols, and reverse-phase column chromatograph treatment using ODS gel, HP resin, etc. is performed to remove mixed fatty acids such as palmitic acid and oleic acid. A high-purity POA can be obtained by removing the image.
本発明の方法によるPOAの抽出精製工程は簡単であ
り、リパーゼ等の高価な酵素の使用を避けることができ
るため、酵母菌体らのPOA製造法として工業的に有利
に収率良く高純度のPOAを回収することができる。The extraction and purification step of POA by the method of the present invention is simple and it is possible to avoid the use of expensive enzymes such as lipase. Therefore, as a method for producing POA from yeast cells, it is industrially advantageous and has a high purity and a high purity. POA can be recovered.
以下、実施例により具体的に説明する。 Hereinafter, a specific description will be given with reference to examples.
実施例1. グルコース1000g、リン酸65g、硫安20g、硫
酸マグネシウム・7H2O 30g、硫酸亜鉛・7H2
O 3g、硫酸第一鉄・7H2O 3g、硫酸銅・7H
2O 150mg、硫酸マンガン・2〜4H2O 300
mg、塩化カリゥム55g、塩化ナトリゥム3g、酵母エ
キス30g、水道水15からなる培地(PH5.0に調
整)で、ジャーファーメンターにより市販パン酵母(商
品名:カネカ レッドイースト)を60時間好気培養し
た後、分離水洗した菌体懸濁液2(菌体乾燥重量30
2g)を調製した。この菌体懸濁液に濃硫酸20mlを加
え(PH1以下)、100℃で約5時間加熱する。冷却
後、水酸化ナトリゥム500gを加えて(PH14以
上)、約10時間100℃でさらに加熱する。冷却後、
濃硫酸325mlを加えPH5.5に調整し、これにn−ヘキ
サン5とイソプロピルアルコール0.5の混液を加え
て攪拌抽出し、静置後n−ヘキサン層を分離する。この
抽出液を5の水で3回洗浄し、上層のn−ヘキサン層
のみを減圧下で濃縮する。この濃縮物を少量のn−ヘキ
サンに溶かした後、4℃まで冷却し、析出してくるステ
ロール類を除去し、メルク社シリカゲル130gをつめ
たカラムにかけ、n−ヘキサン−酢酸エチル混液(10
0:0.2)で溶出した。ユビキノン、ステロール類と分
画したPOAの溶出区分を減圧下で濃縮し、POA純度
56%のオイル3.2gが得られた(収率54%)。さら
に高純度POAを調製するため、得られたオイル3gを
少量のエタノールに溶かした後、YMC、ODSゲル4
5gをつめたカラムにかけエタノール−水混液(60:
40)で溶出した。パルミチン酸、オレイン酸等の脂肪
酸と分画したPOAの高純度溶出区分を減圧下で濃縮
し、純度98%以上のPOAオイル1.0gを得た(収率
60%)。本品はガスクロマトグラフィー、薄層クロマ
トグラフィー、赤外吸収スペクトル分析の結果からcis
−9−ヘキサデセン酸(パルミトレイン酸)であること
が確認された。本発明の方法と、前述と同一方法で培養
後、巻装した酵母菌体から常法であるクロロホルム−メ
タノール混液(2:1)で抽出し、ケン化処理後、本発
明の方法と同様な操作で高純度POAを調製した結果を
比較して表1に示した。Example 1. Glucose 1000 g, phosphoric acid 65 g, ammonium sulfate 20 g, magnesium sulfate · 7H 2 O 30 g, zinc sulfate · 7H 2
O 3g, ferrous sulfate, 7H 2 O 3g, copper sulfate, 7H
2 O 150 mg, manganese sulfate 2-4 H 2 O 300
Aerobic culture of commercially available baker's yeast (trade name: Kaneka Red Yeast) for 60 hours with a jar fermenter in a medium (adjusted to PH 5.0) consisting of mg, 55 g of potassium chloride, 3 g of sodium chloride, 30 g of yeast extract, and 15 tap water. Then, the bacterial cell suspension 2 separated and washed with water (dry cell mass of 30
2g) was prepared. 20 ml of concentrated sulfuric acid is added to this cell suspension (PH1 or less), and the mixture is heated at 100 ° C. for about 5 hours. After cooling, 500 g of sodium hydroxide is added (PH 14 or more) and the mixture is further heated at 100 ° C. for about 10 hours. After cooling
325 ml of concentrated sulfuric acid was added to adjust the pH to 5.5, a mixed solution of n-hexane 5 and isopropyl alcohol 0.5 was added to this, and the mixture was extracted with stirring. After standing, the n-hexane layer was separated. This extract is washed 3 times with water of 5, and only the upper n-hexane layer is concentrated under reduced pressure. This concentrate was dissolved in a small amount of n-hexane and then cooled to 4 ° C. to remove the precipitated sterols, and the solution was applied to a column packed with 130 g of silica gel of Merck & Co., Inc. and mixed with n-hexane-ethyl acetate (10
It was eluted at 0: 0.2). The eluate fraction of POA fractionated with ubiquinone and sterols was concentrated under reduced pressure to obtain 3.2 g of oil having a POA purity of 56% (yield 54%). In order to prepare higher purity POA, 3 g of the obtained oil was dissolved in a small amount of ethanol, and then YMC and ODS gel 4
Apply to a column packed with 5 g of ethanol-water mixture (60:
40) was eluted. The high purity elution fraction of POA fractionated with fatty acids such as palmitic acid and oleic acid was concentrated under reduced pressure to obtain 1.0 g of POA oil having a purity of 98% or more (yield 60%). This product is cis based on the results of gas chromatography, thin layer chromatography and infrared absorption spectrum analysis.
It was confirmed to be -9-hexadecenoic acid (palmitoleic acid). After culturing with the method of the present invention and the same method as described above, extraction from the wound yeast cells with a chloroform-methanol mixture (2: 1), which is a conventional method, and saponification treatment, the same as the method of the present invention The results of preparing high-purity POA by operation are shown in Table 1 for comparison.
実施例2. 抽出溶剤のクロロホルム−メタノール混液(10:2)
を用い、その他の条件は実施例1と同様な方法でWin
e yeast IFO 2229からの高純度POA
抽出精製を行ない、純度98%以上のPOAオイル1.7
gを得た。その結果及び抽出前処理としてアルカリ処理
のみからの結果を併せ表1に示した。Example 2. Chloroform-methanol mixture of extraction solvent (10: 2)
And other conditions are the same as those in the first embodiment.
high purity POA from e yeast IFO 2229
POA oil 1.7 with a purity of 98% or higher
g was obtained. The results are shown in Table 1 together with the results obtained by only the alkali treatment as the extraction pretreatment.
実施例3. 市販乾燥ビール酵母菌体200gを水道水にて菌体懸濁
液2に調整した。この菌体懸濁液を上記実施例1と同
様な操作を行ない、純度98%以上のPOAオイル0.5
gが得られ、その結果及び乾燥菌体から常法クロロホル
ム−メタノール混液(2:1)抽出精製した結果を表1
に示した。Example 3. 200 g of commercially available dry brewer's yeast cells was adjusted to a cell suspension 2 with tap water. This bacterial cell suspension was treated in the same manner as in Example 1 above to obtain 0.5% POA oil with a purity of 98% or more.
g was obtained, and the result and the result of extraction and purification by a conventional chloroform-methanol mixture (2: 1) from the dried cells were shown in Table 1.
It was shown to.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 池田 勉 兵庫県高砂市伊保崎3−2−19 (72)発明者 樋口 正造 兵庫県神戸市垂水区青山台2−14−3 (72)発明者 河智 義弘 滋賀県草津市野路町1922−323 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Tsutomu Ikeda 3-2-19 Ibosaki Takasago, Hyogo Prefecture (72) Inventor Shozo Higuchi 2-14-3 Aoyamadai, Tarumi-ku, Kobe City, Hyogo Prefecture (72) Inventor Kawachi Yoshihiro 1922-323 Nojimachi, Kusatsu City, Shiga Prefecture
Claims (2)
を含有する酵母の菌体水懸濁液を予め酸で加熱処理し、
次いでアルカリでケン化した後、酸性下で水と混合しな
い溶剤にて抽出を行ない、遊離型POAを含有するオイ
ルを採取することを特徴とするパルミトレイン酸の製造
法。1. Palmitoleic acid (hereinafter abbreviated as POA)
The yeast cell suspension containing yeast is preheated with an acid,
Next, a method for producing palmitoleic acid, which comprises saponifying with an alkali and then extracting under acidic conditions with a solvent that is immiscible with water to collect an oil containing free POA.
順相ゲルクロマト法にて共雑物を除去した後、逆相ゲル
クロマト処理を行ない、98%以上の高純度POAオイ
ルを採取する特許請求の範囲第1項記載の製造法。2. Crystallization of oil containing free POA and removal of contaminants by normal phase gel chromatography followed by reverse phase gel chromatography to obtain 98% or higher high-purity POA oil. The manufacturing method according to claim 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61139902A JPH0634730B2 (en) | 1986-06-16 | 1986-06-16 | Method for producing palmitoleic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61139902A JPH0634730B2 (en) | 1986-06-16 | 1986-06-16 | Method for producing palmitoleic acid |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62296885A JPS62296885A (en) | 1987-12-24 |
JPH0634730B2 true JPH0634730B2 (en) | 1994-05-11 |
Family
ID=15256283
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61139902A Expired - Lifetime JPH0634730B2 (en) | 1986-06-16 | 1986-06-16 | Method for producing palmitoleic acid |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0634730B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014129140A1 (en) | 2013-02-19 | 2014-08-28 | 日清食品ホールディングス株式会社 | Instant food product |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2336307C2 (en) * | 2000-01-19 | 2008-10-20 | Мартек Биосайнсис Корпорейшн | Method of obtaining lipids (versions) and lipids obtained by this method |
-
1986
- 1986-06-16 JP JP61139902A patent/JPH0634730B2/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014129140A1 (en) | 2013-02-19 | 2014-08-28 | 日清食品ホールディングス株式会社 | Instant food product |
Also Published As
Publication number | Publication date |
---|---|
JPS62296885A (en) | 1987-12-24 |
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