JPH053280B2 - - Google Patents

Info

Publication number: JPH053280B2
Authority: JP; Japan
Prior art keywords: rhamnose; flavonoid; highly purified; enzyme; solution
Prior art date: 1985-06-26
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

Application number

JP13969485A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62293A (ja

Inventor

Takuo Sakai

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Kanegafuchi Chemical Industry Co Ltd

Original Assignee

Kanegafuchi Chemical Industry Co Ltd

Priority date (The priority date 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 date listed.)

1985-06-26

Filing date

1985-06-26

Publication date

1993-01-14

1985-06-26 Application filed by Kanegafuchi Chemical Industry Co Ltd filed Critical Kanegafuchi Chemical Industry Co Ltd

1985-06-26 Priority to JP13969485A priority Critical patent/JPS62293A/ja

1987-01-06 Publication of JPS62293A publication Critical patent/JPS62293A/ja

1993-01-14 Publication of JPH053280B2 publication Critical patent/JPH053280B2/ja

Status Granted legal-status Critical Current

Links

SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 37
PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 27
PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 claims description 26
108090000790 Enzymes Proteins 0.000 claims description 17
102000004190 Enzymes Human genes 0.000 claims description 17
239000000243 solution Substances 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 13
-1 flavonoid compound Chemical class 0.000 claims description 12
229930003935 flavonoid Natural products 0.000 claims description 11
229930182486 flavonoid glycoside Natural products 0.000 claims description 11
150000007955 flavonoid glycosides Chemical class 0.000 claims description 11
235000017173 flavonoids Nutrition 0.000 claims description 11
239000007864 aqueous solution Substances 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
239000003495 polar organic solvent Substances 0.000 claims description 3
238000001179 sorption measurement Methods 0.000 claims description 3
230000001376 precipitating effect Effects 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 description 6
239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 description 5
QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 description 5
QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 description 5
APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 description 5
ADSYMQORONDIDD-ZJHVPRRPSA-N hesperetin 7-O-beta-D-glucoside Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)=CC(O)=C2C(=O)C1 ADSYMQORONDIDD-ZJHVPRRPSA-N 0.000 description 5
VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 description 5
QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 description 5
229940025878 hesperidin Drugs 0.000 description 5
238000000034 method Methods 0.000 description 5
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
239000003463 adsorbent Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000008103 glucose Substances 0.000 description 4
108010001078 naringinase Proteins 0.000 description 4
BNRKZHXOBMEUGK-NRBMBCGPSA-N (2r,3r,4r,5r,6s)-6-methyloxane-2,3,4,5-tetrol;hydrate Chemical compound O.C[C@@H]1O[C@@H](O)[C@H](O)[C@H](O)[C@H]1O BNRKZHXOBMEUGK-NRBMBCGPSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001540751 Talaromyces ruber Species 0.000 description 3
239000003957 anion exchange resin Substances 0.000 description 3
108010030923 hesperidinase Proteins 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 description 2
241000228212 Aspergillus Species 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000228143 Penicillium Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229930182478 glucoside Natural products 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
229930019673 naringin Natural products 0.000 description 2
DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 description 2
229940052490 naringin Drugs 0.000 description 2
239000000758 substrate Substances 0.000 description 2
YFVGIJBUXMQFOF-PJOVQGMDSA-N 5-hydroxy-2-(4-methoxyphenyl)-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one Chemical compound C1=CC(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(O)C=C2O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)O1 YFVGIJBUXMQFOF-PJOVQGMDSA-N 0.000 description 1
TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
YFVGIJBUXMQFOF-SAXLCNSLSA-N Linarin Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@H](Oc2cc(O)c3C(=O)C=C(c4ccc(OC)cc4)Oc3c2)O1)[C@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1 YFVGIJBUXMQFOF-SAXLCNSLSA-N 0.000 description 1
241000235648 Pichia Species 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
210000002421 cell wall Anatomy 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
150000002772 monosaccharides Chemical class 0.000 description 1
ARGKVCXINMKCAZ-UZRWAPQLSA-N neohesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@H]3[C@@H]([C@H](O)[C@@H](O)[C@H](C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UZRWAPQLSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)

JP13969485A 1985-06-26 1985-06-26 Ｌ−ラムノ−スの製造法 Granted JPS62293A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP13969485A JPS62293A (ja)	1985-06-26	1985-06-26	Ｌ−ラムノ−スの製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP13969485A JPS62293A (ja)	1985-06-26	1985-06-26	Ｌ−ラムノ−スの製造法

Publications (2)

Publication Number	Publication Date
JPS62293A JPS62293A (ja)	1987-01-06
JPH053280B2 true JPH053280B2 (fr)	1993-01-14

Family

ID=15251239

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP13969485A Granted JPS62293A (ja)	1985-06-26	1985-06-26	Ｌ−ラムノ−スの製造法

Country Status (1)

Country	Link
JP (1)	JPS62293A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK0575908T3 (da) *	1992-06-25	2000-07-24	Aventis Res & Tech Gmbh & Co	Pseudomonas aeroginosa og dens anvendelse til fremstilling af L-rhamnose
DE59310216D1 (de)	1992-11-27	2001-10-25	Aventis Res & Tech Gmbh & Co	Heterogenes Proteingemisch mit alpha-L-rhamnosidase Aktivität, Verfahren zu ihrer Herstellung und ihre Verwendung.
DE19850029A1 (de)	1998-10-30	2000-05-04	Merck Patent Gmbh	Verfahren zur enzymatischen Spaltung von Rutinosiden

1985
- 1985-06-26 JP JP13969485A patent/JPS62293A/ja active Granted

Also Published As

Publication number	Publication date
JPS62293A (ja)	1987-01-06

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