JP2007084500A - Method for producing extract containing s-alkenyl(or alkyl)cysteine sulfoxide compounds in high concentration - Google Patents
Method for producing extract containing s-alkenyl(or alkyl)cysteine sulfoxide compounds in high concentration Download PDFInfo
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- JP2007084500A JP2007084500A JP2005277424A JP2005277424A JP2007084500A JP 2007084500 A JP2007084500 A JP 2007084500A JP 2005277424 A JP2005277424 A JP 2005277424A JP 2005277424 A JP2005277424 A JP 2005277424A JP 2007084500 A JP2007084500 A JP 2007084500A
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- JP
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- Prior art keywords
- alkenyl
- alkyl
- enzyme
- garlic
- extract
- 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
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 39
- 239000000284 extract Substances 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- BHLMCOCHAVMHLD-REOHCLBHSA-N S-oxy-L-cysteine Chemical class OC(=O)[C@@H](N)CS=O BHLMCOCHAVMHLD-REOHCLBHSA-N 0.000 title description 2
- 102000004190 Enzymes Human genes 0.000 claims abstract description 44
- 229940088598 enzyme Drugs 0.000 claims abstract description 44
- 108090000790 Enzymes Proteins 0.000 claims abstract description 43
- -1 cysteine sulfoxide compound Chemical class 0.000 claims abstract description 36
- 108010059892 Cellulase Proteins 0.000 claims abstract description 25
- 229940106157 cellulase Drugs 0.000 claims abstract description 25
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 108010059820 Polygalacturonase Proteins 0.000 claims abstract description 19
- 108010093305 exopolygalacturonase Proteins 0.000 claims abstract description 17
- 241000234280 Liliaceae Species 0.000 claims abstract description 15
- 108010055059 beta-Mannosidase Proteins 0.000 claims abstract description 13
- 102100032487 Beta-mannosidase Human genes 0.000 claims abstract description 12
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 11
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 11
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 6
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 35
- 235000018417 cysteine Nutrition 0.000 claims description 35
- 235000013305 food Nutrition 0.000 claims description 7
- 239000000419 plant extract Substances 0.000 claims description 4
- 235000013361 beverage Nutrition 0.000 claims 1
- 240000002234 Allium sativum Species 0.000 description 35
- 235000004611 garlic Nutrition 0.000 description 35
- 239000000047 product Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000843 powder Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 18
- XUHLIQGRKRUKPH-UHFFFAOYSA-N S-allyl-L-cysteine sulfoxide Natural products OC(=O)C(N)CS(=O)CC=C XUHLIQGRKRUKPH-UHFFFAOYSA-N 0.000 description 17
- XUHLIQGRKRUKPH-GCXOYZPQSA-N Alliin Natural products N[C@H](C[S@@](=O)CC=C)C(O)=O XUHLIQGRKRUKPH-GCXOYZPQSA-N 0.000 description 16
- XUHLIQGRKRUKPH-DYEAUMGKSA-N alliin Chemical compound OC(=O)[C@@H](N)C[S@@](=O)CC=C XUHLIQGRKRUKPH-DYEAUMGKSA-N 0.000 description 16
- 235000015295 alliin Nutrition 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 239000007788 liquid Substances 0.000 description 13
- 239000006000 Garlic extract Substances 0.000 description 12
- 235000020706 garlic extract Nutrition 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 239000000796 flavoring agent Substances 0.000 description 11
- 235000019634 flavors Nutrition 0.000 description 11
- 239000003205 fragrance Substances 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000000341 volatile oil Substances 0.000 description 8
- 239000003925 fat Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 235000011194 food seasoning agent Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 240000006108 Allium ampeloprasum Species 0.000 description 5
- 235000005254 Allium ampeloprasum Nutrition 0.000 description 5
- 229920001353 Dextrin Polymers 0.000 description 5
- 239000004375 Dextrin Substances 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 235000019425 dextrin Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000006911 enzymatic reaction Methods 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 238000010298 pulverizing process Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 235000021438 curry Nutrition 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 235000014347 soups Nutrition 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 3
- 108010092760 Alliin lyase Proteins 0.000 description 3
- 244000291564 Allium cepa 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
- 239000003513 alkali Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 description 3
- 230000000593 degrading effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000019688 fish Nutrition 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- 235000013606 potato chips Nutrition 0.000 description 3
- 235000015067 sauces Nutrition 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 244000294411 Mirabilis expansa Species 0.000 description 2
- 235000015429 Mirabilis expansa Nutrition 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- OKYHUOHBRKWCQJ-FTJYXMLISA-N S-1-propenyl-L-cysteine sulfoxide zwitterion Chemical compound C\C=C\S(=O)C[C@H](N)C(O)=O OKYHUOHBRKWCQJ-FTJYXMLISA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 235000013536 miso Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 235000013580 sausages Nutrition 0.000 description 2
- 235000011888 snacks Nutrition 0.000 description 2
- 235000013555 soy sauce Nutrition 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 238000005728 strengthening Methods 0.000 description 2
- CSZTZFUEOCFFJH-YGVKFDHGSA-N (2r)-2-amino-3-ethylsulfinylpropanoic acid Chemical compound CCS(=O)C[C@H](N)C(O)=O CSZTZFUEOCFFJH-YGVKFDHGSA-N 0.000 description 1
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 description 1
- ZZLHPCSGGOGHFW-ZMQIUWNVSA-N (2s)-2-amino-3-methylsulfinylpropanoic acid Chemical compound CS(=O)C[C@@H](N)C(O)=O ZZLHPCSGGOGHFW-ZMQIUWNVSA-N 0.000 description 1
- LUEWUZLMQUOBSB-FSKGGBMCSA-N (2s,3s,4s,5s,6r)-2-[(2r,3s,4r,5r,6s)-6-[(2r,3s,4r,5s,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5s,6r)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](OC3[C@H](O[C@@H](O)[C@@H](O)[C@H]3O)CO)[C@@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-FSKGGBMCSA-N 0.000 description 1
- JDLKFOPOAOFWQN-VIFPVBQESA-N Allicin Natural products C=CCS[S@](=O)CC=C JDLKFOPOAOFWQN-VIFPVBQESA-N 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 102100039851 DNA-directed RNA polymerases I and III subunit RPAC1 Human genes 0.000 description 1
- 101710112289 DNA-directed RNA polymerases I and III subunit RPAC1 Proteins 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 101710156496 Endoglucanase A Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229920002324 Galactoglucomannan Polymers 0.000 description 1
- 229920000926 Galactomannan Polymers 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 229920002581 Glucomannan Polymers 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 229920000057 Mannan Polymers 0.000 description 1
- 235000005135 Micromeria juliana Nutrition 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- 101710184309 Probable sucrose-6-phosphate hydrolase Proteins 0.000 description 1
- ZZLHPCSGGOGHFW-UHFFFAOYSA-N S-methyl-L-cysteine sulphoxide Natural products CS(=O)CC(N)C(O)=O ZZLHPCSGGOGHFW-UHFFFAOYSA-N 0.000 description 1
- JZKMSAGUCSIIAH-UHFFFAOYSA-N S-n-propyl-L-cysteine sulfoxide Natural products CCCS(=O)CC(N)C(O)=O JZKMSAGUCSIIAH-UHFFFAOYSA-N 0.000 description 1
- 241000020719 Satsuma Species 0.000 description 1
- 240000002114 Satureja hortensis Species 0.000 description 1
- 235000007315 Satureja hortensis Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 102400000472 Sucrase Human genes 0.000 description 1
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- 238000002835 absorbance Methods 0.000 description 1
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- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002156 adsorbate Substances 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- JDLKFOPOAOFWQN-UHFFFAOYSA-N allicin Chemical compound C=CCSS(=O)CC=C JDLKFOPOAOFWQN-UHFFFAOYSA-N 0.000 description 1
- 235000010081 allicin Nutrition 0.000 description 1
- 108010012864 alpha-Mannosidase Proteins 0.000 description 1
- 102000019199 alpha-Mannosidase Human genes 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000015241 bacon Nutrition 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
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- OKYHUOHBRKWCQJ-UHFFFAOYSA-N cis S-1-Propenyl-L-cystein Natural products CC=CS(=O)CC(N)C(O)=O OKYHUOHBRKWCQJ-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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- 238000000691 measurement method Methods 0.000 description 1
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- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
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- 239000013588 oral product Substances 0.000 description 1
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 description 1
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
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- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
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Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Cosmetics (AREA)
Abstract
Description
本発明はユリ科植物の食用部由来のS−アルケニル(またはアルキル)システインスルフォキサイド類を高濃度に含有する抽出物の製造方法に関する。 The present invention relates to a method for producing an extract containing a high concentration of S-alkenyl (or alkyl) cysteine sulfoxides derived from the edible part of a lily family.
摺りおろしたニンニクを簡便に使用できる物として、チューブや瓶、プラスチック容器など様々な形態で市販されているが、ニンニクは摺り下ろした瞬間に酵素反応により香気が発生するが、時間が経つとともに新鮮な香気は劣化してしまうという欠点がある。 Garlic is marketed in various forms such as tubes, bottles, plastic containers, etc. that can be easily used, but garlic has an aroma due to an enzyme reaction at the moment it is crushed, but it becomes fresh over time. There is a drawback that the aroma is deteriorated.
ユリ科植物の食用部にはアリイン、イソアリインに代表されるS−アルケニル(またはアルキル)システインスルフォキサイド類が含まれており、これらはアリイナーゼなどの分解酵素により、アリシンなどを経由し、各種のスルフィド類やジチイン類などの揮発性含硫化合物に分解されることが知られている。これの揮発性含硫化合物はニンニクに代表されるユリ科植物の特徴的香気成分として知られている。しかしながら、これらの揮発性含硫化合物は分解しやすいため、ニンニク香気強化の目的でこれらの揮発性含硫化合物を香料として添加した場合でも、経時変化により香気が劣化するという欠点は解消することができない。 The edible part of the liliaceae plant contains S-alkenyl (or alkyl) cysteine sulfoxides represented by alliin and isoallyin, and these are various enzymes via decomposing enzymes such as alliinase and allicin. It is known that it is decomposed into volatile sulfur-containing compounds such as sulfides and dithiines. This volatile sulfur-containing compound is known as a characteristic aroma component of a lily family represented by garlic. However, since these volatile sulfur-containing compounds are easily decomposed, even when these volatile sulfur-containing compounds are added as a fragrance for the purpose of strengthening garlic aroma, the disadvantage that the aroma deteriorates with time can be eliminated. Can not.
S−アルケニル(またはアルキル)システインスルフォキサイド類はこれらの香気の植物体中でのプレカーサーであるが、食品などに揮発性含硫化合物のプレカーサーとして添加すると徐々に分解して香気が生成し、香気が長期間持続する効果が得られるため大変有用な物質である。また、近年の天然指向より、S−アルケニル(またはアルキル)システインスルフォキサイド類を香気プレカーサーとして食品に使用する場合、天然からの抽出物であることが好ましい。 S-alkenyl (or alkyl) cysteine sulfoxides are precursors of these fragrances in plant bodies, but when they are added to foods as precursors of volatile sulfur-containing compounds, they gradually decompose and produce fragrances. It is a very useful substance because of its long-lasting effect. Moreover, from the recent natural orientation, when using S-alkenyl (or alkyl) cysteine sulfoxides as a fragrance precursor in foods, it is preferably an extract from nature.
ニンニクからアリインを抽出する技術としては、ニンニクを熱水中で酵素失活させた後破砕して水を加えた抽出液を逆相系カラムを用いた液体クロマトグラフィーにより精製する方法(特許文献1)、ニンニクを急速加熱し、水を加え粗砕し、分離して得られた液にビタミンB1、糠または酵母を添加して、セルラーゼ処理することによる無臭ニンニク液の製法(特許文献2)が知られている。 As a technique for extracting alliin from garlic, a method in which garlic is enzyme-inactivated in hot water and then crushed and purified by liquid chromatography using a reversed-phase column (Patent Document 1). ), A method for producing an odorless garlic liquid (patent document 2) by rapidly heating garlic, adding water, coarsely crushing, separating the liquid, adding vitamin B1, koji or yeast, and subjecting it to cellulase treatment. Are known.
しかしながら特許文献1の精製方法により得られるアリインの量は少量であり、工業的な生産に向いているとは言えない。また特許文献2の方法で得られる無臭ニンニク液はアリインを満足できる濃度で含有していない。従って本発明の目的は、天然物由来で高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物の製造方法を提供することである。 However, the amount of alliin obtained by the purification method of Patent Document 1 is small and cannot be said to be suitable for industrial production. Moreover, the odorless garlic liquid obtained by the method of Patent Document 2 does not contain alliin at a satisfactory concentration. Accordingly, an object of the present invention is to provide a method for producing an extract containing a high concentration of S-alkenyl (or alkyl) cysteine sulfoxides derived from a natural product.
本発明者は、天然物由来で高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物の製造方法について鋭意研究を行った。その結果、ユリ科植物の食用部に酵素としてマンナナーゼ、セルラーゼおよびペクチナーゼの3種類全てを併用して処理することで粉砕工程を行うことなくきわめて容易かつ効率的な液状化が可能であり、このものは固液分離、濾過、カラム通液などの工業的操作が容易であることを見出した。さらに得られた抽出液を、強酸性陽イオン交換樹脂を充填したカラムに通液し、その後アルカリ溶液にて脱着することで、天然物由来でかつ高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物が得られることを見出し本発明を完成するに至った。 The present inventor has conducted intensive research on a method for producing an extract containing a natural product and containing a high concentration of S-alkenyl (or alkyl) cysteine sulfoxides. As a result, it is possible to liquefy very easily and without pulverization process by processing all three types of mannanase, cellulase and pectinase as enzymes in the edible part of lily family plants. Found that industrial operations such as solid-liquid separation, filtration and column passage were easy. Further, the obtained extract was passed through a column packed with a strongly acidic cation exchange resin, and then desorbed with an alkaline solution, so that it was derived from a natural product and had a high concentration of S-alkenyl (or alkyl) cysteine. The inventors have found that an extract containing foxides can be obtained, and have completed the present invention.
すなわち本発明は、ユリ科植物の食用部を酵素処理した後、イオン交換樹脂処理することを特徴とする高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物の製造方法を提供するものである。
本発明はまた、酵素がマンナナーゼ、セルラーゼおよびペクチナーゼの3種類全てを含むことを特徴とする前記の高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物の製造方法が提供される。
本発明はまた、イオン交換樹脂が強酸性陽イオン交換樹脂である前記の高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物の製造方法を提供することができる。
さらに、本発明は、S−アルケニル(またはアルキル)システインスルフォキサイド類が抽出物の乾燥物当たり10重量%以上含まれている前記の高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物の製造方法を提供するものである。
本発明はまた、前記いずれかの方法により得られるユリ科植物抽出物を提供するものである。
本発明はまた、前記方法によって得られるユリ科植物抽出物を含有する飲食品を提供するものである。
That is, the present invention provides an extract containing a high concentration of S-alkenyl (or alkyl) cysteine sulfoxides, characterized in that an edible part of a lily family plant is treated with an enzyme and then treated with an ion exchange resin. A method is provided.
The present invention also provides a method for producing an extract containing the above-mentioned high concentration S-alkenyl (or alkyl) cysteine sulfoxides, wherein the enzyme contains all three types of mannanase, cellulase and pectinase. Provided.
This invention can also provide the manufacturing method of the extract containing the said high concentration S-alkenyl (or alkyl) cysteine sulfoxides whose ion exchange resin is a strong acidic cation exchange resin.
Furthermore, the present invention relates to the above-mentioned high concentration S-alkenyl (or alkyl) cysteine sulfoxide containing 10% by weight or more of the S-alkenyl (or alkyl) cysteine sulfoxides per dry matter of the extract. The present invention provides a method for producing an extract containing sides.
The present invention also provides a lily family plant extract obtained by any one of the methods described above.
This invention also provides the food-drinks containing the lily family plant extract obtained by the said method.
本発明により高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物の容易且つ簡便な工業的製造方法を提供することができる。得られた抽出物はそのまま、あるいは粉末化、硬化油脂被覆粉末などの形態とし、その形態で必要に応じて酵素と反応させ、香気を発生させることができるため、ユリ科植物の香気プレカーサーとして使用できる。また、このプレカーサーを添加した場合、香気の持続性が大きく改善されるという効果が得られる。 The present invention can provide an easy and simple industrial production method for an extract containing a high concentration of S-alkenyl (or alkyl) cysteine sulfoxides. The obtained extract can be used as it is or in the form of powdered or hardened oil / fat coated powder, etc., which can be reacted with an enzyme as necessary to generate a fragrance. it can. Moreover, when this precursor is added, the effect that the persistence of a fragrance is improved significantly is acquired.
以下、本発明についてさらに詳細に説明する。
本発明において使用することのできるユリ科の植物としてはニンニク、タマネギ、ワケギ、ニラ、ギョウジャニンニク、ナガネギ、ラッキョウ、及びリークを挙げることができるが、S−アルケニル(またはアルキル)システインスルフォキサイド類を含有している植物であれば、これらに限定されるものではない。また好ましい植物としてはニンニク、タマネギ、ナガネギ、ニラを、特に好ましい植物としてはニンニクを例示することができる。本発明ではこれらの可食部を原料として使用する。
Hereinafter, the present invention will be described in more detail.
Examples of liliaceae plants that can be used in the present invention include garlic, onion, scallion, leek, garlic, garlic, leeks, and leeks, but S-alkenyl (or alkyl) cysteine sulfoxides. As long as it contains plants, it is not limited to these. Examples of preferable plants include garlic, onion, leeks and leek, and particularly preferable plants include garlic. In the present invention, these edible parts are used as raw materials.
まず、原料は水洗して汚れや雑菌を取り除き、そのまま、あるいは剥皮し、必要に応じて適当な大きさに裁断した後、急速加熱を行う。この工程により植物細胞内に含まれるアリイナーゼなどの分解酵素を失活させ、S−アルケニル(またはアルキル)システインスルフォキサイド類が分解することを防ぐことができる。急速加熱の方法はアリイナーゼなどの分解酵素が失活される方法であれば特に制限はないが、蒸煮処理、熱湯処理、マイクロ波処理などを例示することができる。 First, the raw material is washed with water to remove dirt and germs, as it is, or peeled off, cut into an appropriate size as necessary, and then rapidly heated. By this step, a degrading enzyme such as alliinase contained in the plant cell can be inactivated, and S-alkenyl (or alkyl) cysteine sulfoxides can be prevented from being degraded. The rapid heating method is not particularly limited as long as a degrading enzyme such as alliinase is inactivated, and examples thereof include steaming treatment, hot water treatment, and microwave treatment.
引き続き酵素処理により、植物組織の分解を行い、S−アルケニル(またはアルキル)システインスルフォキサイド類の抽出と抽出系全体の粘性および分離特性を改善する。本発明ではこの酵素処理においてマンナナーゼ、セルラーゼおよびペクチナーゼの3種全てを使用することが重要である。酵素処理においてマンナナーゼ、セルラーゼまたはペクチナーゼから選ばれる1種または2種を使用した場合でも、S−アルケニル(またはアルキル)システインスルフォキサイド類の抽出と抽出系全体の粘性および分離特性をある程度改善することは可能である。しかしながら、今回発明者などはこれら3種全てを併用することで、1種または2種の酵素を使用した場合に比べ組織分解が格段に進み、その後の分離、濾過、カラム通液が工業的規模でも可能となることを見出した。特にカラム通液においては3種全てを使用した場合、1種または2種を使用した場合に比べ、抽出液の粘度が格段に下がるため、製造上きわめて有利となることを見出した。 Subsequently, the plant tissue is decomposed by enzymatic treatment, and the viscosity of the S-alkenyl (or alkyl) cysteine sulfoxides and the viscosity and separation characteristics of the entire extraction system are improved. In the present invention, it is important to use all three types of mannanase, cellulase and pectinase in this enzyme treatment. Even when one or two selected from mannanase, cellulase or pectinase is used in the enzyme treatment, the extraction of S-alkenyl (or alkyl) cysteine sulfoxides and the viscosity and separation characteristics of the entire extraction system are improved to some extent. It is possible. However, the present inventors have used all three types together, so that the tissue degradation has progressed significantly compared to the case where one or two enzymes are used, and the subsequent separation, filtration, and column passage are on an industrial scale. But I found it possible. In particular, it has been found that when all three types are used in the column flow, the viscosity of the extract is remarkably reduced as compared with the case where one or two types are used, which is extremely advantageous in production.
マンナナーゼはマンナン、グルコマンナン、ガラクトマンナン、ガラクトグルコマンナンなどの構成成分中にマンノースを含む多糖類を加水分解する酵素で、β−マンナナーゼ、α−マンノシダーゼ、β−マンノシダーゼなどが知られている。マンナナーゼは糸状菌などの培養によって採取される培養物、培養液、該培養物を適量の水や緩衝液で抽出した抽出液、該培養液から菌を濾別した培養液、或いはこれらの液を濃縮した液に含まれるものを用いることができる。また、植物に由来するもや、各種のものが利用可能である。市販のマンナナーゼ製剤としては、スミチームACH−L(新日本化学工業社製)、セルロシンGM5(エイチビィアイ社製)、ビガラーゼM(洛東化成工業社製)などを例示することができる。かかるマンナナーゼの使用量は、酵素の力価によっても異なるが、通常、原料としたユリ科植物の重量を基準として約10〜約10,000U/gの範囲内とすることができる。 Mannanase is an enzyme that hydrolyzes polysaccharides containing mannose in components such as mannan, glucomannan, galactomannan, and galactoglucomannan, and β-mannanase, α-mannosidase, β-mannosidase, and the like are known. Mannanase is a culture obtained by culturing filamentous fungi, a culture solution, an extract obtained by extracting the culture with an appropriate amount of water or a buffer, a culture solution obtained by filtering bacteria from the culture solution, or these solutions. What is contained in the concentrated liquid can be used. Moreover, various things can be used from plants. Examples of commercially available mannanase preparations include Sumiteam ACH-L (manufactured by Shinnippon Kagaku Kogyo Co., Ltd.), cellulosin GM5 (manufactured by HIBI), Vigarase M (manufactured by Toto Kasei Kogyo Co., Ltd.), and the like. The amount of mannanase used varies depending on the enzyme titer, but can usually be in the range of about 10 to about 10,000 U / g based on the weight of the lily family plant as a raw material.
ペクチナーゼはポリガラクツロナーゼ、ペクチックエンザイム、ポリメチルガラクツロナーゼ、ペクチンデポリメラーゼとも呼ばれ、ペクリニン酸、ペクチン、ペクチン酸などのα(1−4)結合を加水分解する酵素である。また、ガラクツロン酸のカルボキシル基のメチルエステルを加水分解するペクチンメチルエステラーゼを含める場合も多い。ペクチナーゼは、細菌、カビ、酵母、高等植物、カタツムリなどに含まれていることが知られており、本発明ではこれらをはじめとする生物から取得したペクチナーゼを広く使用することができる。また、市販のペクチナーゼ製剤を使用してもよい。市販のペクチナーゼ製剤としては、例えば、スクラーゼ(三共社製)、ペクチネックスウルトラSP−L(ノボザイムズA/S社製)、メイセラーゼ(明治製菓社製)、ウルトラザイム(ノボザイムズA/S社製)、ペクチナーゼG、ニューラーゼF(以上天野エンザイム社製)などを例示することができる。かかるペクチナーゼの使用量は、酵素の力価によっても異なるが、通常、原料としたユリ科植物の重量を基準として約30〜約3,000U/gの範囲内とすることができる。 Pectinase is also called polygalacturonase, pectin enzyme, polymethylgalacturonase, and pectin depolymerase, and is an enzyme that hydrolyzes α (1-4) bonds such as peculinic acid, pectin, and pectic acid. In addition, pectin methylesterase that hydrolyzes the methyl ester of the carboxyl group of galacturonic acid is often included. Pectinases are known to be contained in bacteria, molds, yeasts, higher plants, snails and the like, and pectinases obtained from organisms including these can be widely used in the present invention. A commercially available pectinase preparation may also be used. Examples of commercially available pectinase preparations include, for example, sucrase (manufactured by Sankyo), pectinex ultra SP-L (manufactured by Novozymes A / S), mecerase (manufactured by Meiji Seika Co., Ltd.), ultrazyme (manufactured by Novozymes A / S), Examples include pectinase G and neurase F (manufactured by Amano Enzyme Inc.). The amount of pectinase used varies depending on the titer of the enzyme, but can usually be in the range of about 30 to about 3,000 U / g based on the weight of the lily family plant as a raw material.
セルラーゼはセルロースを加水分解する活性を有する酵素である。セルロースはD−グルコースがβ−1,4結合で分枝無くつながった多糖類の一種でグルコースの数はおよそ5,000個程度と言われている。植物の細胞壁の主要な構成成分で、親水性は強いが水に不溶である。セルラーゼとしては、セルロースを分解する活性を有するものであれば特に制限はなく任意のものを使用することができ、市販品のセルラーゼ製剤としては例えば、セルラーゼT「アマノ」、セルラーゼA「アマノ」(以上天野エンザイム社製)、ドリセラーゼKSM、マルチフェクトA40、セルラーゼGC220(以上ジェネンコア協和社製)、セルラーゼGODO−TCL、セルラーゼGODO TCD−H、ベッセレックス、セルラーゼGODO−ACD(以上合同酒精社製)、Cellulase(東洋紡績社製)、セルライザー、セルラーゼXL−522(以上ナガセケムテックス社製)、セルソフト、デニマックス(以上ノボザイムズ社製)、セルロシンAC40、セルロシンAL、セルロシンT2(以上エイチビィアイ社製)、セルラーゼ“オノズカ”3S、セルラーゼY−NC(以上ヤクルト薬品工業社製)、スミチームAC、スミチームC(以上新日本化学工業社製)、エンチロンCM、エンチロンMCH、バイオヒット(洛東化成工業社製)などが挙げられる。かかるセルラーゼの使用量は、酵素の力価によっても異なるが、通常、原料としたユリ科植物の重量を基準として約1〜約1,000U/gの範囲内とすることができる。 Cellulase is an enzyme having an activity of hydrolyzing cellulose. Cellulose is a kind of polysaccharide in which D-glucose is connected without branching by β-1,4 bonds, and the number of glucose is said to be about 5,000. It is a major component of plant cell walls and is strongly hydrophilic but insoluble in water. Cellulase is not particularly limited as long as it has an activity of degrading cellulose, and any cellulase can be used. Examples of commercially available cellulase preparations include cellulase T “Amano”, cellulase A “Amano” ( As described above, manufactured by Amano Enzyme Co., Ltd.), Doricerase KSM, Multifect A40, Cellulase GC220 (manufactured by Genencor Kyowa Co., Ltd.), Cellulase GODO-TCL, Cellulase GODO TCD-H, Besselex, Cellulase GODO-ACD (manufactured by Godo Shusei Co., Ltd.), Cellulase (manufactured by Toyobo Co., Ltd.), cell riser, cellulase XL-522 (manufactured by Nagase ChemteX), cell soft, Denimax (manufactured by Novozymes), cellulosin AC40, cellulosin AL, cellulosin T2 (manufactured by HI Corporation) , Cellulase “Onozuka” 3S, Cellulase Y-NC (Yakult Pharmaceutical Co., Ltd.), Sumiteam AC, Sumiteam C (Shin Nihon Chemical Industry Co., Ltd.), Enchiron CM, Enchiron MCH, Bio Hit ). The amount of cellulase used varies depending on the titer of the enzyme, but can usually be in the range of about 1 to about 1,000 U / g based on the weight of the lily family plant as a raw material.
酵素による処理は、それ自体既知の方法、例えば特許庁公報周知・慣用技術集(香料)第II部 食品香料(2000.1.14発行)微生物・酵素フレーバー(P46〜P57)などの刊行物に記載の方法に準じて行うことができる。 Treatment with an enzyme is a method known per se, for example, publications such as the Patent Office Gazette Known and Conventional Techniques (fragrance) Part II Food Fragrance (issued 2000.1.14) Microorganism / Enzyme Flavor (P46-P57) It can be performed according to the method described.
一実施態様を例示すれば次の通りである。前記の急速加熱した原料1重量部をホールの状態あるいは荒く粉砕した後、水を添加あるいは水無添加で、約60〜約121℃で約2秒〜約20分間殺菌した後冷却し、上記の3種類の酵素を添加して、攪拌あるいは静置し20〜70℃にて0.5〜24時間反応を行う。例えば原料がニンニクの場合、粉砕を行わなくとも酵素反応は進行するが、酵素反応をある程度速く進めるためには荒く粉砕した方が有利である。しかしながら、あまり細かく粉砕してしまうとその後の分離、濾過の工程に時間を要する。酵素反応時に添加する水の量は酵素を反応系全体に行き渡らすことができる最低量で充分であり、原料の粉砕を行った場合には原料の種類によっては使用しなくても反応は可能であるが、原料に対し0〜2倍程度を例示することができる。 An example of one embodiment is as follows. 1 part by weight of the rapidly heated raw material is pulverized roughly in a hole state or without water, and sterilized at about 60 to about 121 ° C. for about 2 seconds to about 20 minutes and then cooled, Three kinds of enzymes are added, and the reaction is carried out at 20 to 70 ° C. for 0.5 to 24 hours with stirring or standing. For example, when the raw material is garlic, the enzyme reaction proceeds without pulverization, but rough pulverization is advantageous in order to advance the enzyme reaction to some extent. However, if it is pulverized too finely, it takes time for the subsequent separation and filtration processes. The minimum amount of water that can be added to the entire reaction system is sufficient for the amount of water added during the enzyme reaction. If the raw material is pulverized, the reaction is possible even if it is not used depending on the type of raw material. However, it is possible to exemplify about 0 to 2 times the raw material.
酵素処理後、約60〜約121℃で約2秒〜約20分間加熱することにより酵素失活する。その後冷却し、遠心分離、濾紙濾過などの適宜な分離手段によって残渣を分離することにより分離液を得ることができる。 After the enzyme treatment, the enzyme is inactivated by heating at about 60 to about 121 ° C. for about 2 seconds to about 20 minutes. Thereafter, it is cooled, and the separation liquid can be obtained by separating the residue by a suitable separation means such as centrifugal separation or filter paper filtration.
引き続きイオン交換樹脂にて処理を行う。使用するイオン交換樹脂は陽イオン交換樹脂(H+型)を使用するが、好ましくは強酸性陽イオン交換樹脂(H+型)、より好ましくはスルホン酸型強酸性陽イオン交換樹脂を使用する。スルホン酸型強酸性陽イオン交換樹脂としては、例えば、ダイヤイオンUBK−550(三菱化学社製)、ダイヤイオンSK1B(三菱化成社製)、アンバーライト IR120B、アンバーライト 200C、デュオライトC−26(以上Rohm&Haas社製)、ダウエックス MSC−1(DOWEX社製)、LEWATIT SP−112(LEWATIT社製)などが挙げられる。樹脂に接触させる方式は回分式、カラム式いずれでも良いが、生産規模ではカラム方式の方が一般的である。樹脂の使用量は、抽出液に含まれるS−アルケニル(またはアルキル)システインスルフォキサイド類含量によるため一様に設定できないが、S−アルケニル(またはアルキル)システインスルフォキサイド類を全て吸着(交換)することが可能な量であればいかなる量でも良く、例えば抽出液に対し0.1倍〜10倍量を例示することができる。また、通液の条件としては通液速度SV=0.5〜5を例示することができる。 Subsequently, treatment is performed with an ion exchange resin. The ion exchange resin used is a cation exchange resin (H + type), preferably a strong acid cation exchange resin (H + type), more preferably a sulfonic acid type strong acid cation exchange resin. Examples of the sulfonic acid type strongly acidic cation exchange resin include Diaion UBK-550 (manufactured by Mitsubishi Chemical Corporation), Diaion SK1B (manufactured by Mitsubishi Kasei), Amberlite IR120B, Amberlite 200C, Duolite C-26 ( Rohm & Haas), Dowex MSC-1 (DOWEX), LEWATIT SP-112 (LEWATIT) and the like. The method of contacting the resin may be either a batch method or a column method, but the column method is more common on the production scale. The amount of resin used cannot be set uniformly because of the content of S-alkenyl (or alkyl) cysteine sulfoxides contained in the extract, but all S-alkenyl (or alkyl) cysteine sulfoxides are adsorbed. Any amount can be used as long as it can be (exchanged), for example, 0.1 to 10 times the amount of the extract can be exemplified. Moreover, as a condition of liquid flow, liquid flow speed SV = 0.5-5 can be illustrated.
吸着後、イオン交換樹脂に対し0.1〜10倍量の水を通液し不要な成分を除き、アルカリ溶液によりS−アルケニル(またはアルキル)システインスルフォキサイド類を脱着(交換)し、高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物を得ることができる。脱着の際に使用するアルカリの種類に特に制限はないが、水酸化ナトリウム、炭酸ナトリウム、水酸化カリウム、アンモニア水などが挙げられる。またアルカリの濃度および量は強酸性陽イオン交換樹脂に吸着したS−アルケニル(またはアルキル)システインスルフォキサイド類を脱着できる濃度および量であればよく、濃度は0.5〜3N、量は対イオン交換樹脂1〜5倍容量を例示することができる。 また、通液の条件としては通液速度SV=0.5〜5を例示することができる。また、脱着に際しては脱着のS−アルケニル(またはアルキル)システインスルフォキサイド類含量を確認し、S−アルケニル(またはアルキル)システインスルフォキサイド類濃度の高い画分のみを集めることにより、さらに高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物を得ることができる。S−アルケニル(またはアルキル)システインスルフォキサイド類の含有量は抽出物の乾燥重量当たり10%以上とすることができ、好ましくは15%以上、より好ましくは20%以上とすることが可能である。 After adsorption, 0.1 to 10 times the amount of water is passed through the ion exchange resin to remove unnecessary components, and S-alkenyl (or alkyl) cysteine sulfoxides are desorbed (exchanged) with an alkaline solution. Extracts containing high concentrations of S-alkenyl (or alkyl) cysteine sulfoxides can be obtained. Although there is no restriction | limiting in particular in the kind of alkali used in the case of desorption, Sodium hydroxide, sodium carbonate, potassium hydroxide, aqueous ammonia etc. are mentioned. The concentration and amount of the alkali may be any concentration and amount that can desorb the S-alkenyl (or alkyl) cysteine sulfoxides adsorbed on the strongly acidic cation exchange resin. The concentration is 0.5 to 3 N, and the amount is A 1 to 5 times capacity of the counter ion exchange resin can be exemplified. Moreover, as a condition of liquid flow, liquid flow speed SV = 0.5-5 can be illustrated. Further, upon desorption, the content of desorbed S-alkenyl (or alkyl) cysteine sulfoxides is confirmed, and only a fraction having a high concentration of S-alkenyl (or alkyl) cysteine sulfoxides is collected. Extracts containing high concentrations of S-alkenyl (or alkyl) cysteine sulfoxides can be obtained. The content of S-alkenyl (or alkyl) cysteine sulfoxides can be 10% or more, preferably 15% or more, more preferably 20% or more, based on the dry weight of the extract. is there.
なお、本発明で言うS−アルケニル(またはアルキル)システインスルフォキサイド類の例としては、アリイン(S−アリルシステインスルフォキサイド)、イソアリイン(S−1−プロペニルシステインスルフォキサイド)、S−メチルシステインスルフォキサイド、S−エチルシステインスルフォキサイド、S−プロピルシステインスルフォキサイド、 S−ブチルステインスルフォキサイド、シクロアリイン、γ−L−グルタミル−S−プロペニルシステインスルフォキサイドなどが挙げられるが、これらに限定されるものではない。 Examples of the S-alkenyl (or alkyl) cysteine sulfoxides referred to in the present invention include alliin (S-allyl cysteine sulfoxide), iso alliin (S-1-propenyl cysteine sulfoxide), S-methyl cysteine sulfoxide, S-ethyl cysteine sulfoxide, S-propyl cysteine sulfoxide, S-butyl stein sulfoxide, cycloaliyne, γ-L-glutamyl-S-propenyl cysteine sulfoxide Examples include foxside, but are not limited thereto.
得られたS−アルケニル(またはアルキル)システインスルフォキサイド類を高濃度に含む抽出物は、そのまま、あるいは酸を加えて中和、あるいは透析またはイオン交換によりアルカリを除去した後、さらに濃縮、所望により、デキストリン、化工澱粉、サイクロデキストリン、アラビアガムなどの賦形剤を添加してペースト状、粉末状とすることができ、粉末はさらに硬化油脂被覆粉末など様々な形態とすることができる。 The obtained extract containing S-alkenyl (or alkyl) cysteine sulfoxides at a high concentration is concentrated as it is, or neutralized by adding an acid, or after removing alkali by dialysis or ion exchange. If desired, excipients such as dextrin, modified starch, cyclodextrin, gum arabic and the like can be added to form a paste or powder, and the powder can be further formed into various forms such as a hardened oil / fat coated powder.
かくして得られた高濃度のS−アルケニル(またはアルキル)システインスルフォキサイド類を含有する抽出物もしくはそれを含む組成物が使用される飲食物は、可食性のものであれば特に限定されることはないが、例えばおろしニンニク、焼肉のたれ、シーズニングオイル、シーズニングパウダー、ウスターソース、トマトケチャップ、マヨネーズ、固形ブイヨン、蠣油、カレールー、シチューの素、スープの素、ダシの素、味噌、粉末味噌、醤油、粉末醤油、もろみ、魚醤、食酢などの各種調味料;ポテトチップスなどの各種スナック食品類;即席麺などの各種インスタント食品類;和風スープ類、洋風スープ類などのスープ類;ハム、ソーセージ、ベーコン、ドライソーセージ、ビーフジャーキーなどの食肉加工品;魚肉ハム、魚肉ソーセージ、蒲鉾、ちくわ、はんぺん、薩摩揚げなどの水産加工品;即席カレー、レトルトカレー、缶詰カレーなどのカレー類;油脂を含有する各種レンジ食品及び冷凍食品;バター、マーガリン、チーズなどの酪農・油脂製品;口腔製品;医薬品;飼料などが例示される。
以下、本発明を実施例および比較例によりさらに具体的に説明する。
The food and drink in which the extract containing the high-concentration S-alkenyl (or alkyl) cysteine sulfoxides thus obtained or the composition containing the same is used is particularly limited as long as it is edible. For example, grated garlic, grilled meat sauce, seasoning oil, seasoning powder, Worcester sauce, tomato ketchup, mayonnaise, solid bouillon, salmon oil, curry roux, stew base, soup base, dashi base, miso, powdered miso , Soy sauce, powdered soy sauce, moromi, fish sauce, vinegar and other seasonings; potato chips and other snack foods; instant noodles and other instant foods; Japanese soups and western soups and other soups; ham, Meat products such as sausage, bacon, dry sausage, beef jerky; fish ham, fish meat Processed marine products such as sage, salmon, chikuwa, hampen, fried Satsuma; curry such as instant curry, retort curry, canned curry; various range and frozen foods containing fats and oils; dairy and fats such as butter, margarine, cheese Examples include products; oral products; pharmaceuticals; feeds and the like.
Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples.
実施例1
市販ニンニク(中国産)の皮をむき、剥きニンニク500gを沸騰水にて10分間煮沸後、ざるにあけ、水を切り、2Lセパラブルフラスコに入れた。イオン交換水500gを加え90℃、5分間加熱後、50℃に冷却し、セルロシン GM5(エイチビィアイ社製)1.25gを水12.5gに溶解したもの、ペクチナーゼG(天野エンザイム社製)1.25gを水12.5gに溶解したものおよびセルラーゼT(天野エンザイム社製)1.25gを水12.5gに溶解したものを添加し、50℃、16時間静置反応した。その後50℃、2時間攪拌を行った後、90℃、10分間加熱攪拌して酵素を失活した。40℃まで冷却後、40メッシュ濾過を行い、酵素処理ニンニク抽出液932.5g(発明品1:Bx17.2°、アリイン含量0.254%)を得た。発明品1の粘度は20℃で、43mPa・sであった。引き続き、東洋濾紙No.2(5.5cm)にセルロースパウダー10gを濾過助剤としてコーティングしたヌッチェを使用し0.01MPaにて減圧濾過を行い濾液905gを得た。濾過に要した時間は6.3分であった。次いで濾液をダイヤイオンUBK−550(三菱化学社製)646mlにSV=2で通液した。通過液にアリインが含まれていないことをTLCにて確認後、イオン交換樹脂をイオン交換水2513mlで洗浄した。洗浄液にはアリインが含まれていないことをTLCにて確認した。次に以下の溶離液を通過させ吸着物の脱着を行った。
フラクション1:1Nアンモニア水 1077ml
フラクション2:2Nアンモニア水 1077ml
フラクション3:1Nアンモニア水 2154ml
それぞれのフラクションをTLCで確認したところ、フラクション2にのみアリインが確認された。フラクション2をロータリエバポレーターを用いて濃縮後、真空乾燥し、乾燥物(発明品2)9.5gを得た(対剥きニンニク収率1.9%)。発明品2のアリイン含量をHPLCにて測定したところ22.8%であった。
(アリイン含量の測定方法)
誘導化試薬の調製:
オルト−フタルジアルデヒド(OPA)140mgをメタノール5mlに溶解し、ついで2−メチル−2−プロパンチオール0.1mlを攪拌しながら混合し、さらに0.05モルのリン酸2水素ナトリウム水溶液(pH9.5)50mlを加え、誘導化試薬とした。
Example 1
Commercial garlic (made in China) was peeled and 500 g of peeled garlic was boiled in boiling water for 10 minutes, then poured into a sieve, drained, and placed in a 2 L separable flask. 500 g of ion-exchanged water was added, heated at 90 ° C. for 5 minutes, cooled to 50 ° C., 1.25 g of cellulosin GM5 (manufactured by HIBI) dissolved in 12.5 g of water, pectinase G (manufactured by Amano Enzyme) A solution prepared by dissolving 25 g in 12.5 g of water and 1.25 g of cellulase T (manufactured by Amano Enzyme) in 12.5 g of water were added, and the mixture was allowed to stand at 50 ° C. for 16 hours. After stirring at 50 ° C. for 2 hours, the enzyme was deactivated by heating and stirring at 90 ° C. for 10 minutes. After cooling to 40 ° C., 40 mesh filtration was performed to obtain 932.5 g of enzyme-treated garlic extract (Invention 1: B × 17.2 °, Alliin content 0.254%). Inventive product 1 had a viscosity of 43 mPa · s at 20 ° C. Toyo Filter Paper No. No. 2 (5.5 cm) coated with 10 g of cellulose powder as a filter aid was used and filtered under reduced pressure at 0.01 MPa to obtain 905 g of filtrate. The time required for the filtration was 6.3 minutes. Next, the filtrate was passed through 646 ml of Diaion UBK-550 (Mitsubishi Chemical Corporation) at SV = 2. After confirming by TLC that alliin was not contained in the passing liquid, the ion exchange resin was washed with 2513 ml of ion exchange water. It was confirmed by TLC that the washing liquid did not contain alliin. Next, the adsorbate was desorbed by passing the following eluent.
Fraction 1: 1 10N ammonia water 1077ml
Fraction 2: 2N ammonia water 1077 ml
Fraction 3: 1N ammonia water 2154ml
When each fraction was confirmed by TLC, alliin was confirmed only in fraction 2. Fraction 2 was concentrated using a rotary evaporator and then vacuum-dried to obtain 9.5 g of a dried product (Invention product 2) (vs. peeled garlic yield of 1.9%). The alliin content of invention product 2 was measured by HPLC and found to be 22.8%.
(Measurement method of alliin content)
Preparation of derivatization reagent:
140 mg of ortho-phthaldialdehyde (OPA) is dissolved in 5 ml of methanol, and then 0.1 ml of 2-methyl-2-propanethiol is mixed with stirring, and 0.05 mol of sodium dihydrogen phosphate aqueous solution (pH 9. 5) 50 ml was added to obtain a derivatizing reagent.
標準品、試料の調製:
試薬のアリインを使用し、20ppmおよび80ppmの標準溶液を調製した(いずれも80%メタノールに溶解)。それぞれの標準液および試料溶液400μlに誘導化試薬600μlを加え、室温下で30分静置し反応させた。
Standards and sample preparation:
Using reagent alliin, standard solutions of 20 ppm and 80 ppm were prepared (both dissolved in 80% methanol). 600 μl of the derivatization reagent was added to 400 μl of each standard solution and sample solution, and allowed to stand for 30 minutes at room temperature to react.
高速液体クロマトグラフィーの条件:
装置 :Waters HPLC system
カラム:Waters Symetry C18 5μm 4.6×150mm
検出機:Waters 2487 dual λ absorbance dete ctor
移動相A:0.1m酢酸ナトリウム(pH7.2)/アセトニトリル/テトラヒドロフラン=900/95/5
移動相B:アセトニトリル/水=800/200
流速 :0.7ml/min
検出 :紫外吸収(吸光度の測定):337nm
注入量:20μl
グラジェント条件:表1に示す
High-performance liquid chromatography conditions:
Apparatus: Waters HPLC system
Column: Waters Symmetry C18 5 μm 4.6 × 150 mm
Detector: Waters 2487 dual λ absorbance dete ctor
Mobile phase A: 0.1 m sodium acetate (pH 7.2) / acetonitrile / tetrahydrofuran = 900/95/5
Mobile phase B: acetonitrile / water = 800/200
Flow rate: 0.7 ml / min
Detection: UV absorption (absorbance measurement): 337 nm
Injection volume: 20 μl
Gradient conditions: shown in Table 1
実施例2(ニンニクエキス粉末およびニンニクエキス硬化油被覆粉末の製造)
水84.64gに発明品2を9.5gおよびデキストリン(DE12)11.66gを溶解し、60〜70℃で溶解した後40℃まで冷却した。これを真空乾燥、ミキサー粉砕し乾燥しニンニクエキス粉末21.0g(発明品3:アリイン含量10.0%、平均粒径100μ)を得た。さらに得られたニンニクエキス粉末21gと硬化菜種油(平均粒径10μ)21gを自動乳鉢(ヤマト科学社製ラボミルモデルUT−21)を用い、15rpmにて2時間混合し、ニンニクエキス硬化油脂被覆粉末42g(発明品4:アリイン含量5%)を得た。
Example 2 (Production of garlic extract powder and garlic extract hardened oil-coated powder)
9.5 g of Invention 2 and 11.66 g of dextrin (DE12) were dissolved in 84.64 g of water, dissolved at 60 to 70 ° C. and then cooled to 40 ° C. This was vacuum dried, pulverized with a mixer and dried to obtain 21.0 g of garlic extract powder (Invention 3: Alliin content 10.0%, average particle size 100 μm). Further, 21 g of the obtained garlic extract powder and 21 g of hardened rapeseed oil (average particle size 10 μm) were mixed for 2 hours at 15 rpm using an automatic mortar (Laborum Model UT-21 manufactured by Yamato Kagaku Co., Ltd.), and the garlic extract hardened oil and fat coated powder 42 g (Invention 4: Alliin content 5%) was obtained.
比較例1(ニンニク精油粉末およびニンニク精油硬化油被覆粉末の製造)
水150gにアラビアガム40gおよびデキストリン40g(DE12)添加し、60〜70℃で溶解した後40℃まで冷却した。これにニンニク精油5gを添加し、T.K.ホモミキサー(特殊機化工業社製)を用い、30〜40℃に保ちながら8000rpmにて10分間攪拌することにより乳化を行った。得られた乳化液をニロ社製モービルマイナースプレードライヤーを用い、送風温度150℃、排風温度80℃で噴霧乾燥し、ニンニク精油粉末80g(比較品1:ニンニク精油含量5%)を得た。さらにこのニンニク精油粉末(平均粒径100μ)80gと硬化菜種油(平均粒径10μ)80gを自動乳鉢(ヤマト科学社製ラボミルモデルUT−21)を用い、15rpmにて2時間混合し、ニンニク精油硬化油脂被覆粉末160g(比較品2:ニンニク精油含量2.5%)を得た。
Comparative Example 1 (Production of garlic essential oil powder and garlic essential oil hardened oil-coated powder)
40 g of gum arabic and 40 g of dextrin (DE12) were added to 150 g of water, dissolved at 60 to 70 ° C., and then cooled to 40 ° C. To this was added 5 g of garlic essential oil. K. Using a homomixer (manufactured by Koki Kogyo Co., Ltd.), emulsification was carried out by stirring at 8000 rpm for 10 minutes while maintaining the temperature at 30 to 40 ° C. The obtained emulsified liquid was spray-dried at a blower temperature of 150 ° C. and an exhaust air temperature of 80 ° C. using a mobile minor spray dryer manufactured by Niro Co., Ltd. to obtain 80 g of garlic essential oil powder (comparative product: garlic essential oil content 5%). Further, 80 g of this garlic essential oil powder (average particle size 100 μm) and 80 g of hardened rapeseed oil (average particle size 10 μm) were mixed at 15 rpm for 2 hours using an automatic mortar (Yamato Scientific Co., Ltd., Lab Mill Model UT-21). 160 g of hardened oil-and-fat coated powder (Comparative product 2: Garlic essential oil content 2.5%) was obtained.
実施例3(スナック用シーズニングパウダーへの応用)
発明品3または比較品1を使用し、下記表2に示す配合割合にてシーズニングパウダーを試作した。このシーズニングパウダーをポテトチップ(塩)に5%ふりかけ、良く訓練された5人のパネラーにより評価した。評価はフレッシュ感およびニンニク臭についてそれぞれの強度を5段階で評価した。また、風味を言葉で表現した。5人の平均点および共通の風味評価を表3に示す。
Example 3 (application to seasoning powder for snacks)
Inventive product 3 or comparative product 1 was used, and a seasoning powder was made as a trial at the blending ratio shown in Table 2 below. This seasoning powder was sprinkled with potato chips (salt) at 5% and evaluated by five well-trained panelists. Evaluation evaluated each intensity | strength in five steps about fresh feeling and a garlic smell. The flavor is expressed in words. Table 3 shows the average scores and common flavor evaluations of the five people.
表3に示したように、発明品3を添加したポテトチップスはニンニク臭が非常に強いとともに、擦りたてのニンニクをイメージさせるシャープなフレッシュ感が非常に強くなっていた。これはニンニク乾燥粉末中に含まれる酵素が唾液の水分により活性化し、発明品3に含まれるS−アルケニル(またはアルキル)システインスルフォキサイド類を分解するため口腔中で香気が発生することによると考えられる。一方比較品1を添加したものは、ニンニク的香気は強化されるが、フレッシュ感はそれほど強くはなかった。 As shown in Table 3, the potato chips to which Invention 3 was added had a very strong garlic odor and a sharp fresh feeling that made fresh garlic image. This is because the enzyme contained in the dried garlic powder is activated by saliva water and decomposes the S-alkenyl (or alkyl) cysteine sulfoxides contained in Invention 3, resulting in aroma in the oral cavity. it is conceivable that. On the other hand, the garlic-like aroma was strengthened with the addition of the comparative product 1, but the fresh feeling was not so strong.
実施例4(おろしニンニク加工品の香気補強)
市販品おろし生ニンニクに発明品4または比較品2を0.5重量%添加混合し、密封容器に充填し、37℃にて4週間保存試験を行った。また、全くの無添加品も同一の条件で保存試験を行った。保存前後の風味を良く訓練された5人のパネラーにより評価した。評価はフレッシュ感、ニンニク臭、漬け物臭についてそれぞれの強度を5段階で評価し、また、風味を言葉で表現した。5人の平均点および共通の風味評価を表4に示す。
Example 4 (Aroma reinforcement of processed grated garlic)
0.5% by weight of Invention 4 or Comparative Product 2 was added to and mixed with commercially available grated garlic, filled in a sealed container, and stored at 37 ° C. for 4 weeks. In addition, a completely non-added product was subjected to a storage test under the same conditions. The flavor before and after storage was evaluated by five well-trained panelists. Evaluation evaluated each intensity | strength in five steps about fresh feeling, a garlic odor, and pickled odor, and expressed the flavor in words. Table 4 shows the average score of 5 people and the common flavor evaluation.
表4に示すとおり、発明品4添加品、比較品2添加品のいずれも無添加品と比べ製造直後、保存後いずれにおいても風味の改良効果が見られた。しかしながら、発明品4添加品、比較品2添加品共に製造直後では刺激を伴うフレッシュな擦りたての風味を有していたが、保存後では比較品2添加品は風味が大幅に劣化していたのに対し、発明品4添加品はフレッシュな風味を持続することができた。発明品4はS−アルケニル(またはアルキル)システインスルフォキサイド類を高濃度に含有するエキスを粉末化し、さらに水分との接触を妨げるため硬化油にて被覆した粉末であるが、上記のようなおろしニンニクに添加した場合、ニンニク中の酵素は硬化油脂被覆粉末に浸透する速度が遅いため、酵素反応が徐々におこなわれ、新鮮な風味が持続できたものと考えられる。一方比較品2はニンニク精油を粉末化し、さらにワックスコートした粉末であるが、香気の強化効果は見られるものの、フレッシュな擦りたての香気を維持することはできなかった。 As shown in Table 4, the effects of improving the flavor were observed in both of the invention 4 additive product and the comparative product 2 additive product immediately after production and after storage as compared with the additive-free product. However, both the invention 4 additive product and the comparative product 2 additive product had a fresh, freshly savory flavor with irritation immediately after production, but the comparison product 2 additive product had a significantly deteriorated flavor after storage. On the other hand, the invention 4 additive product was able to maintain a fresh flavor. Invention 4 is a powder obtained by pulverizing an extract containing S-alkenyl (or alkyl) cysteine sulfoxides at a high concentration and coating with hardened oil to prevent contact with moisture. When added to the garlic, the enzyme in the garlic has a slow rate of permeation into the hardened oil-fat coated powder, so that the enzyme reaction gradually takes place and the fresh flavor is thought to have been sustained. On the other hand, Comparative Product 2 is a powder obtained by pulverizing garlic essential oil and further wax-coating, but although the effect of strengthening the fragrance was observed, it was not possible to maintain the freshly scented fragrance.
比較例2
実施例1において酵素を全く使用せずに、それ以外は実施例1と全く同様の操作を行い下記の酵素無処理ニンニク抽出液を得た。また、実施例1において3種類使用している酵素のうち2種類を使用し、それ以外は実施例1と全く同様の操作を行い下記の酵素処理ニンニク抽出液を得た。
比較品3:酵素無処理ニンニク抽出液(収量552.2g、Bx10.5°)。
比較品4:セルロシン GM5(エイチビィアイ社製)1.25gを水12.5gに溶解したものおよびペクチナーゼG(天野エンザイム社製)1.25gを水12.5gに溶解したもの2種類を使用した酵素処理ニンニク抽出液(収量758.9g、Bx15.1°)。
比較品5:セルロシン GM5(エイチビィアイ社製)1.25gを水12.5gに溶解したものおよびセルラーゼT(天野エンザイム社製)1.25gを水12.5gに溶解したもの2種類を使用した酵素処理ニンニク抽出液(収量803.1g、Bx14.6°)。
比較品6:ペクチナーゼG(天野エンザイム社製)1.25gを水12.5gに溶解したものおよびセルラーゼT(天野エンザイム社製)1.25gを水12.5gに溶解したもの2種類を使用した酵素処理ニンニク抽出液(収量838.3g、Bx15.3°)。
Comparative Example 2
The same enzyme-untreated garlic extract as described below was obtained in the same manner as in Example 1 except that no enzyme was used in Example 1. In addition, two of the three enzymes used in Example 1 were used, and the other operations were performed in exactly the same manner as in Example 1 to obtain the following enzyme-treated garlic extract.
Comparative product 3: Enzyme-untreated garlic extract (yield 552.2 g, Bx 10.5 °).
Comparative Product 4: Cellulosin GM5 (manufactured by HIBI) dissolved in 12.5 g of water and pectinase G (manufactured by Amano Enzyme) 1.25 g dissolved in 12.5 g of water Treated garlic extract (yield 758.9 g, Bx15.1 °).
Comparative product 5: Cellulosin GM5 (manufactured by HBI) 1.25 g of water dissolved in 12.5 g of water and Cellulase T (manufactured by Amano Enzyme) 1.25 g of water dissolved in 12.5 g of water Treated garlic extract (yield 803.1 g, Bx 14.6 °).
Comparative product 6: Two types of pectinase G (manufactured by Amano Enzyme) dissolved in 12.5 g of water and cellulase T (manufactured by Amano Enzyme) 1.25 g dissolved in 12.5 g of water were used. Enzyme-treated garlic extract (yield 838.3 g, Bx15.3 °).
比較品3〜6の抽出液について粘度、アリイン含量を測定した。また比較品3〜6は実施例1と同様に、東洋濾紙No.2(5.5cm)にセルロースパウダー10gを濾過助剤としてコーティングしたヌッチェを使用し0.01MPaにて減圧濾過を行い濾液を得、その際濾過に要した時間を測定した。発明品1および比較品3〜6のそれぞれの粘度、アリイン含量および濾過時間を表5に示す。 Viscosity and alliin content of the extracts of Comparative products 3 to 6 were measured. In addition, Comparative products 3 to 6 were manufactured using Toyo filter paper No. 1 as in Example 1. Using a Nutsche coated with 2 g (5.5 cm) of cellulose powder 10 g as a filter aid, filtration under reduced pressure was performed at 0.01 MPa to obtain a filtrate, and the time required for filtration was measured. Table 5 shows the viscosity, alliin content, and filtration time of Inventive Product 1 and Comparative Products 3-6.
表5から酵素としてマンナナーゼ、セルラーゼおよびペクチナーゼの3種類全てを含むことにより粘度、濾過時間が大幅に改善されたことが示された。 From Table 5, it was shown that viscosity and filtration time were greatly improved by including all three types of enzymes, mannanase, cellulase and pectinase.
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009085663A (en) * | 2007-09-28 | 2009-04-23 | House Foods Corp | Measuring method of acsos in allium plant |
JP2013132279A (en) * | 2011-12-27 | 2013-07-08 | House Foods Corp | Method for producing onion extract having suppressed browning reactivity |
WO2013137284A1 (en) | 2012-03-14 | 2013-09-19 | 日清ファルマ株式会社 | Sulfur amino acid-containing composition |
CN112592765A (en) * | 2020-12-25 | 2021-04-02 | 青岛博恩高科生物技术有限公司 | Preparation method of garlic essential oil |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5093122A (en) * | 1989-11-22 | 1992-03-03 | Wakunaga Seiyaku Kabushiki Kaisha | Method for preparing an s-allylcysteine-containing composition |
WO1999061015A1 (en) * | 1998-05-22 | 1999-12-02 | Nippon Shinyaku Co., Ltd. | Mtp activity-lowering compositions |
US6133440A (en) * | 1997-10-10 | 2000-10-17 | Univera Pharmaceuticals, Inc. | Process for the preparation of immunomodulatory polysaccharides from aloe |
CN1412317A (en) * | 2002-11-16 | 2003-04-23 | 中国科学院新疆理化技术研究所 | Method for extracting alliin from garlic |
WO2003045413A1 (en) * | 2001-11-13 | 2003-06-05 | Pharmaleads, Inc. | Process for harvesting organic compounds from plant roots |
CN1425650A (en) * | 2003-01-13 | 2003-06-25 | 新疆保利达科工贸有限责任公司 | Process for extracting alliin from fresh garlic |
-
2005
- 2005-09-26 JP JP2005277424A patent/JP4954523B2/en not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5093122A (en) * | 1989-11-22 | 1992-03-03 | Wakunaga Seiyaku Kabushiki Kaisha | Method for preparing an s-allylcysteine-containing composition |
US6133440A (en) * | 1997-10-10 | 2000-10-17 | Univera Pharmaceuticals, Inc. | Process for the preparation of immunomodulatory polysaccharides from aloe |
WO1999061015A1 (en) * | 1998-05-22 | 1999-12-02 | Nippon Shinyaku Co., Ltd. | Mtp activity-lowering compositions |
WO2003045413A1 (en) * | 2001-11-13 | 2003-06-05 | Pharmaleads, Inc. | Process for harvesting organic compounds from plant roots |
CN1412317A (en) * | 2002-11-16 | 2003-04-23 | 中国科学院新疆理化技术研究所 | Method for extracting alliin from garlic |
CN1425650A (en) * | 2003-01-13 | 2003-06-25 | 新疆保利达科工贸有限责任公司 | Process for extracting alliin from fresh garlic |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009085663A (en) * | 2007-09-28 | 2009-04-23 | House Foods Corp | Measuring method of acsos in allium plant |
JP2013132279A (en) * | 2011-12-27 | 2013-07-08 | House Foods Corp | Method for producing onion extract having suppressed browning reactivity |
WO2013137284A1 (en) | 2012-03-14 | 2013-09-19 | 日清ファルマ株式会社 | Sulfur amino acid-containing composition |
US9340808B2 (en) | 2012-03-14 | 2016-05-17 | Nisshin Pharma Inc. | Sulfur amino acid-containing composition |
CN112592765A (en) * | 2020-12-25 | 2021-04-02 | 青岛博恩高科生物技术有限公司 | Preparation method of garlic essential oil |
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