JP2017501114A - 植物材料からのグルコサミンの生成 - Google Patents
植物材料からのグルコサミンの生成 Download PDFInfo
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- JP2017501114A JP2017501114A JP2016526297A JP2016526297A JP2017501114A JP 2017501114 A JP2017501114 A JP 2017501114A JP 2016526297 A JP2016526297 A JP 2016526297A JP 2016526297 A JP2016526297 A JP 2016526297A JP 2017501114 A JP2017501114 A JP 2017501114A
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- JP
- Japan
- Prior art keywords
- glucosamine
- ammonium
- dry matter
- plant
- enriched plant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229960002442 glucosamine Drugs 0.000 title claims abstract description 127
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 title claims abstract description 123
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 title claims abstract description 121
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 239000000463 material Substances 0.000 title claims description 36
- 239000000203 mixture Substances 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 47
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 14
- -1 ammonium ions Chemical class 0.000 claims abstract description 13
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- 235000013305 food Nutrition 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- 239000002243 precursor Substances 0.000 claims description 11
- 239000007853 buffer solution Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical group N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 6
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
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- 150000003863 ammonium salts Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
- 238000000605 extraction Methods 0.000 description 15
- 210000003491 skin Anatomy 0.000 description 11
- 229920002101 Chitin Polymers 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 241000238424 Crustacea Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000419 plant extract Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 5
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- CBOJBBMQJBVCMW-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;hydrochloride Chemical compound Cl.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO CBOJBBMQJBVCMW-BTVCFUMJSA-N 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
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- 241000208818 Helianthus Species 0.000 description 2
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- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960001911 glucosamine hydrochloride Drugs 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
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- 229940029339 inulin Drugs 0.000 description 2
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 2
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- MTDHILKWIRSIHB-UHFFFAOYSA-N (5-azaniumyl-3,4,6-trihydroxyoxan-2-yl)methyl sulfate Chemical compound NC1C(O)OC(COS(O)(=O)=O)C(O)C1O MTDHILKWIRSIHB-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C07H1/08—Separation; Purification from natural products
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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Abstract
Description
−植物材料及び少なくとも1種のグルコサミン前駆体を容器に入れる工程、
−この容器を閉める工程、
−この容器を70℃〜110℃の温度にて10時間超加熱する工程、を含む、方法が提供される。
−植物材料及び少なくとも1種のグルコサミン前駆体を容器に入れる工程、
−この容器を閉める工程、
−この容器を70℃〜110℃の温度にて10時間超加熱する工程、を含む、方法が提供される。
特に、植物材料は、スクロース、フルクトース又はイヌリンを含有する、チコリ(Cichorium)、人参(Daucus)、キクイモ(Helianthus)、ビート(Beta)などの植物種からなる群から選択され得る。
特に、収穫し、乾燥した後、再水和した植物材料を出発材料として使用する。
特に、上記のとおりの容器は、任意の形状の容器、広口瓶、又は瓶である。
−前述の容器をあける工程、並びに
−得られたグルコサミン富化植物組成物を乾燥させる工程、を含む方法が提供される。
−溶液のpHを6.5〜7に調節する工程、
−塩化カルシウム溶液を添加する工程、
−エタノールを添加する工程、を含む、方法に更に関する。
200gの市販のサイコロ形状の乾燥チコリ根(0.5×0.5×0.5cm)を0.5M硫酸アンモニウムの溶液に3時間浸漬した。吸液後、チコリ根を容器に入れ、蓋を閉める。この密閉した容器を次に75℃の温度に設定したオーブン(Binder)に48時間放置する。
粉砕した2gのチコリ根を、200mLの水で室温にて30分間抽出する。遠心分離後、上清を凍結乾燥する。この上清を少量分取して分析試験に使用する。
凍結乾燥前の上清を分取し、Acrodisc 0.45μmフィルタでろ過する。
分析装置DIONEX ICS5000を使用し、イオン交換キャピラリーカラムDionex PA 20(4×250mm)でグルコサミンの分析を行う。
分析装置DIONEX ICS2500を使用し、イオン交換分析カラムDionex IonPac AS11−HC12(4×250mm)で硫酸の分析を行う。
分析装置DIONEX ICS2500を使用し、イオン交換分析カラムDionex Ionpac CS 12(4×250mm)P/N 044001でアンモニウムの分析を行う。
−グルコサミン:乾物基準で10.02%。
−アンモニウム:乾物基準で3.90%。
−硫酸 乾物基準で23.78%。
10kgの市販のサイコロ形状の乾燥チコリ根(0.5×0.5×0.5cm)を、硫酸アンモニウム0.5M(30L)溶液に一晩浸漬する。吸液後、チコリ根は湿重量35kg超となる。これを2つのステンレス容器(それぞれ実容積75L)に入れ、蓋を閉めた後、75℃の温度に設定したオーブン(Binder)に48時間放置する。
実施例1に記載のとおりに、抽出及び分析プロトコルを実施する(抽出体積は調節する)。
−グルコサミン:乾物基準で8.09%。
−アンモニウム:乾物基準で3.2%。
−硫酸 乾物基準で22.9%。
実施例1のとおりに加工した、2gのチコリ根粉末を、水の代わりに180mLの炭酸緩衝溶液(pH10.8)で一晩抽出する。
実施例1に記載のとおりに分析プロトコルを実施する(抽出体積は調節する)。
−グルコサミン:乾物基準で8.97%。
−アンモニウム:乾物基準で0.07%。
−硫酸 乾物基準で21.39%。
実施例1のとおりに加工した、2gのチコリ根粉末を、水の代わりに180mLの炭酸緩衝溶液(pH10.8)で一晩抽出する。
実施例1に記載のとおりに分析プロトコルを実施する(抽出体積は調節する)。
−グルコサミン:乾物基準で1.80%。
−アンモニウム:乾物基準で0.07%。
−硫酸:乾物基準で0.10%。
実施例1のとおりに加工した、2gのチコリ根粉末を、水の代わりに180mLの緩衝溶液(pH10.8)で一晩抽出する。
実施例1に記載のとおりに分析プロトコルを実施する(抽出体積は調節する)。
−グルコサミン:乾物基準で0.55%。
−アンモニウム:乾物基準で0.00%。
−硫酸:乾物基準で0.04%。
Claims (15)
- 植物からグルコサミンを生成する方法であって、次の一連の工程:
−植物材料及び少なくとも1種のグルコサミン前駆体を容器に入れる工程、
−前記容器を閉める工程、
−前記容器を70℃〜110℃の温度にて10時間超、加熱する工程、を含む方法。 - 前記加熱する工程が48時間〜96時間継続される、請求項1に記載の方法。
- 前記グルコサミン前駆体が、グルコサミンの生成に必要とされる窒素含有部分をもたらす化合物である、請求項1又は2に記載の方法。
- 前記グルコサミン前駆体が、アンモニウム塩である、請求項1〜3のいずれか一項に記載の方法。
- 前記グルコサミン前駆体が、硫酸アンモニウムである、請求項1〜4のいずれか一項に記載の方法。
- 次の工程:
−前記容器を開ける工程、及び
−得られたグルコサミン富化植物組成物を乾燥させる工程、を更に含む、請求項1〜5のいずれか一項に記載の方法。 - 得られたグルコサミン富化植物組成物を、pH10以上の緩衝溶液で抽出する工程を更に含む、請求項1〜6のいずれか一項に記載の方法。
- 前記緩衝溶液が、pH10.8の炭酸溶液である、請求項7に記載の方法。
- 次の工程:
−前記溶液のpHを6.5〜7に調節する工程、
−塩化カルシウム溶液を添加する工程、
−エタノールを添加する工程、を更に含む、請求項7又は8に記載の方法。 - 請求項7〜9のいずれか一項に記載の方法により得ることのできる、グルコサミン富化植物組成物。
- 乾物1kg当たりにアンモニウムイオンを5g未満含む、請求項10に記載のグルコサミン富化植物組成物。
- 乾物1kg当たりにアンモニウムイオンを5g未満含み、かつ乾物1kg当たりに硫酸イオンを5g未満含む、請求項9に記載の方法により得ることのできる、グルコサミン富化植物組成物。
- 乾物1kg当たりにアンモニウムイオンを1g未満含み、かつ乾物1kg当たりに硫酸イオンを2g未満含む、請求項12に記載のグルコサミン富化植物組成物。
- 請求項10〜13のいずれか一項に記載のグルコサミン富化植物組成物を含む、食品組成物。
- 請求項10〜13のいずれか一項に記載のグルコサミン富化植物組成物を含む、化粧料組成物。
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EP13191665.2 | 2013-11-05 | ||
EP13191665 | 2013-11-05 | ||
PCT/EP2014/073784 WO2015067640A1 (en) | 2013-11-05 | 2014-11-05 | Generation of glucosamine from plant material |
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EP (1) | EP3071587B1 (ja) |
JP (1) | JP2017501114A (ja) |
CN (1) | CN105683207B (ja) |
AU (1) | AU2014345675B2 (ja) |
BR (1) | BR112016008714B1 (ja) |
CL (1) | CL2016000885A1 (ja) |
ES (1) | ES2663800T3 (ja) |
MX (1) | MX369889B (ja) |
MY (1) | MY183215A (ja) |
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JP2020196738A (ja) * | 2020-08-20 | 2020-12-10 | 株式会社ファーマフーズ | ヒアルロン酸産生促進剤 |
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CN105683207B (zh) | 2019-07-23 |
PL3071587T3 (pl) | 2018-07-31 |
PH12016500702A1 (en) | 2016-05-30 |
CN105683207A (zh) | 2016-06-15 |
ES2663800T3 (es) | 2018-04-17 |
PH12016500702B1 (en) | 2016-05-30 |
EP3071587A1 (en) | 2016-09-28 |
CL2016000885A1 (es) | 2016-10-21 |
AU2014345675B2 (en) | 2018-06-14 |
SG11201601854VA (en) | 2016-05-30 |
US10227368B2 (en) | 2019-03-12 |
WO2015067640A1 (en) | 2015-05-14 |
US20160257705A1 (en) | 2016-09-08 |
MX369889B (es) | 2019-11-25 |
BR112016008714B1 (pt) | 2020-02-04 |
EP3071587B1 (en) | 2018-01-03 |
AU2014345675A1 (en) | 2016-03-24 |
MY183215A (en) | 2021-02-18 |
MX2016005061A (es) | 2016-07-19 |
NO3071587T3 (ja) | 2018-06-02 |
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