CN110526996A - 一种硒化魔芋葡甘寡糖及其制备和应用 - Google Patents
一种硒化魔芋葡甘寡糖及其制备和应用 Download PDFInfo
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- CN110526996A CN110526996A CN201810509300.0A CN201810509300A CN110526996A CN 110526996 A CN110526996 A CN 110526996A CN 201810509300 A CN201810509300 A CN 201810509300A CN 110526996 A CN110526996 A CN 110526996A
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- China
- Prior art keywords
- konjac glucomannan
- oligo
- selenizing
- preparation
- konjac
- Prior art date
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Links
- 229920002752 Konjac Polymers 0.000 title claims abstract description 119
- 239000000252 konjac Substances 0.000 title claims abstract description 119
- 229920002581 Glucomannan Polymers 0.000 title claims abstract description 85
- 229940046240 glucomannan Drugs 0.000 title claims abstract description 85
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 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 title claims description 22
- -1 glucomannan oligosaccharide Chemical class 0.000 claims abstract description 62
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 20
- 239000011669 selenium Substances 0.000 claims abstract description 20
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 7
- 230000002378 acidificating effect Effects 0.000 claims abstract description 7
- 230000003712 anti-aging effect Effects 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 7
- 229940079593 drug Drugs 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 5
- 229940124599 anti-inflammatory drug Drugs 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims abstract description 3
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract 3
- 239000000243 solution Substances 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
- 229940091258 selenium supplement Drugs 0.000 claims description 18
- 235000019441 ethanol Nutrition 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims description 7
- 229910001626 barium chloride Inorganic materials 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- BVTBRVFYZUCAKH-UHFFFAOYSA-L disodium selenite Chemical compound [Na+].[Na+].[O-][Se]([O-])=O BVTBRVFYZUCAKH-UHFFFAOYSA-L 0.000 claims description 6
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 5
- RNGFNLJMTFPHBS-UHFFFAOYSA-L dipotassium;selenite Chemical compound [K+].[K+].[O-][Se]([O-])=O RNGFNLJMTFPHBS-UHFFFAOYSA-L 0.000 claims description 5
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- 229910052939 potassium sulfate Inorganic materials 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims description 4
- 235000011151 potassium sulphates Nutrition 0.000 claims description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 4
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- PMYDPQQPEAYXKD-UHFFFAOYSA-N 3-hydroxy-n-naphthalen-2-ylnaphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(NC(=O)C3=CC4=CC=CC=C4C=C3O)=CC=C21 PMYDPQQPEAYXKD-UHFFFAOYSA-N 0.000 claims description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 239000001110 calcium chloride Substances 0.000 claims description 3
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 3
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- 235000017550 sodium carbonate Nutrition 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 239000011655 sodium selenate Substances 0.000 claims description 3
- 229960001881 sodium selenate Drugs 0.000 claims description 3
- 235000018716 sodium selenate Nutrition 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 2
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 2
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 2
- YAZJAPBTUDGMKO-UHFFFAOYSA-L potassium selenate Chemical compound [K+].[K+].[O-][Se]([O-])(=O)=O YAZJAPBTUDGMKO-UHFFFAOYSA-L 0.000 claims description 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims description 2
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- 206010028980 Neoplasm Diseases 0.000 claims 1
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- 240000006365 Vitis vinifera Species 0.000 claims 1
- 235000014787 Vitis vinifera Nutrition 0.000 claims 1
- 125000003147 glycosyl group Chemical group 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 241001312219 Amorphophallus konjac Species 0.000 abstract description 100
- 235000001206 Amorphophallus rivieri Nutrition 0.000 abstract description 100
- 235000010485 konjac Nutrition 0.000 abstract description 100
- 229920001542 oligosaccharide Polymers 0.000 abstract description 63
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- 229940082569 selenite Drugs 0.000 abstract description 6
- MCAHWIHFGHIESP-UHFFFAOYSA-L selenite(2-) Chemical compound [O-][Se]([O-])=O MCAHWIHFGHIESP-UHFFFAOYSA-L 0.000 abstract description 6
- 230000000259 anti-tumor effect Effects 0.000 abstract description 5
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- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical group OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 abstract description 4
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- 229930182555 Penicillin Natural products 0.000 description 3
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 2
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Classifications
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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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0087—Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
- C08B37/009—Konjac gum or konjac mannan, i.e. beta-D-glucose and beta-D-mannose units linked by 1,4 bonds, e.g. from Amorphophallus species; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
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- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
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- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Veterinary Medicine (AREA)
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Abstract
本发明涉及一种硒化魔芋葡甘寡糖及其制备和应用，硒化魔芋葡甘寡糖的重均分子量为350‑10000Da，主链由葡萄糖基和甘露糖基以β‑1,4糖苷键连结；硒以亚硒酸酯的形式连接在葡萄糖基或甘露糖基的C6和/或C2和/或C3位；硒的含量为0.2‑1.5％(w/w)。制备方法是将魔芋葡甘寡糖加入酸性水溶液中，加入硒化试剂和催化剂后加热反应，加入硫酸盐，离心去除沉淀；上清液用碱中和至中性；加入有机醇后抽滤得到固体，干燥后得到硒化魔芋葡甘寡糖；本发明所述硒化魔芋葡甘寡糖作为活性成份用于延缓衰老保健食品、抑制肿瘤保健药物、抗炎症药物、或抗氧化食品。
Description
技术领域
本发明涉及硒化魔芋葡甘寡糖，具体的说是硒化魔芋葡甘寡糖及其制备和应用。
背景技术
魔芋是天南星科磨芋属多年生草本植物。中国早在两千多年前就开始栽培魔芋了，食用历史也相当悠久。日本有1500多年的种植和食用历史，有100多年的魔芋精粉加工史，而中国虽有2000多年的民间栽种历史，但真正的魔芋精粉加工只是八十年代中期才开始。魔芋多糖又称魔芋葡甘露聚糖(Konjac glucomannan，KGM)，魔芋多糖具有多种的用途。除医学、食品保健外魔芋，魔芋多糖在纺织、印染、化妆、陶瓷、消防、环保、军工、石油开采等方面都有广泛的用途。
魔芋多糖通过β-1，4吡喃糖苷键将β-D-葡萄糖和β-D-甘露糖按1∶1.6或1∶1.69的摩尔比连接而成，每19个糖残基上有一个乙酰基团存在，其特殊的结构使其虽具有多种生物学功能，但是其在水中为胶体、粘度大、溶解度小，使用过程不便；其在各种食品中添加量小，影响其生物活性；将魔芋多糖降解成魔芋寡糖，即魔芋葡甘寡糖(Konjac oligo-glucomannan KOGM)，其子量小，在水中可溶，易于吸收，将会克服上述问题。现有研究表明KOGM具有多种生物活性，与魔芋多糖相比，魔芋低聚糖具有优良的性能，具有改善食品品质，保鲜食品，改善人体肠道菌群，增强免疫力，调节血糖、血脂以及肠道解毒、促进家畜生长和提高肉料比等生物活性。
硒具有抗衰老、抗肿瘤、调节机体免疫力、影响人和动物的生殖发育、解毒生物学功能。天然提取的多糖中硒含量很低，即使在富硒地区种植的魔芋提取的多糖含硒量也低于5mg/kg。
分析魔芋葡甘寡糖和硒的生物活性，急需开发高硒含量的硒化魔芋葡甘寡糖。但是目前国内外关于魔芋葡甘寡糖制备的报道很少，更没有硒化魔芋葡甘寡糖的报道。
发明内容
本发明在本团队建立高效酶法制备魔芋葡甘寡糖的基础上，创造性的建立了硒化魔芋葡甘寡糖的制备技术，获得了高硒含量的魔芋葡甘寡糖，可广泛应用于延缓衰老保健食品、抑制肿瘤保健药物、抗炎症药物和抗氧化食品。
本发明的目的在于提供上述硒化魔芋葡甘寡糖及其制备和应用。
为实现上述目的，本发明一方面提供一种硒化魔芋葡甘寡糖，其特征在于：所述硒化魔芋葡甘寡糖的重均分子量为350-10000Da，主链由葡萄糖基和甘露糖基以β-1,4糖苷键连结；硒以亚硒酸酯的形式连接在葡萄糖基或甘露糖基的C6和/或C2和/或C3位；硒的含量为0.2-1.5％(w/w)。
本发明另一方面提供上述硒化魔芋葡甘寡糖的制备方法，包括以下步骤：
(1)将魔芋葡甘寡糖(重均分子量350-10000Da，通常由摩尔比为1：1.3-2.0的葡萄糖和甘露糖通过β-1,4糖苷键聚合而成)；加入酸性水溶液中，再依次加入硒化试剂、催化剂，在20-90℃下反应2-12小时，得溶液A；
(2)向所述溶液A中加入硫酸盐，得混合物，离心处理所述混合物；上清液用碱中和至中性，得溶液B；
(3)向所述溶液B中加入有机醇，得沉淀物(实验观察为白色)；抽滤沉淀物得到固体，将所述固体真空干燥，得到所述硒化魔芋葡甘寡糖。
所述步骤(1)中，硒化试剂为亚硒酸钠、亚硒酸钾、硒酸钠、硒酸钾中的至少一种，硒化试剂的加入量以硒的摩尔数计，为魔芋葡甘寡糖糖残基摩尔数(以重量/162计算)的0.5-3倍；优选亚硒酸钠、亚硒酸钾；催化剂为氯化钡、氯化钙中的至少一种，催化剂的加入量为魔芋葡甘寡糖糖残基摩尔数(以重量/162计算)的0.5-1.5倍；优选氯化钡。
所述步骤(1)中，魔芋葡甘寡糖的质量含量为酸性水溶液的0.5-120％。
所述步骤(1)中，酸性水溶液为硝酸、硫酸、盐酸、醋酸、磷酸中的至少一种，酸的质量含量为0.2-2％；优选硝酸。
所述步骤(2)中，离心处理的转速为4000-8000rpm。
所述步骤(2)中，硫酸盐为硫酸钠、硫酸钾、硫酸铵、硫酸氢钠、硫酸氢钾中的至少一种，硫酸盐加入量为魔芋葡甘寡糖糖残基摩尔数(以重量/162计算)的0.5-1.5倍。
所述步骤(2)中，碱为碳酸氢钠、碳酸钠、碳酸氢钾、碳酸钾、氢氧化钠、氢氧化钾中的至少一种；
所述步骤(3)中，有机醇为乙醇、甲醇、异丙醇中的至少一种；有机醇的加入量为溶液B体积的3-8倍；优选乙醇；真空干燥的温度为30-80℃，时间为1-3小时。
本发明再一方面提供上述硒化魔芋葡甘寡糖的应用，所述硒化魔芋葡甘寡糖作为活性成份用于延缓衰老保健食品、抑制肿瘤保健药物、抗炎症药物或抗氧化食品
本发明具有如下优点：
1.本发明提供的硒化魔芋葡甘寡糖具有更高的硒含量，生物活性更好。
2.本发明提供的硒化魔芋葡甘寡糖制备方法条件温和、操作简单，便于工业化；
3.本发明提供的硒化魔芋葡甘寡糖具有多种生物活性，具有广泛的应用领域和应用前景。
附图说明
图1.魔芋葡甘寡糖的质谱图；
图2.硒化魔芋葡甘寡糖的红外光谱图。
具体实施方式
下面结合实施实例对本发明做进一步说明：
魔芋葡甘寡糖的制备：以0.5％(w/v)的魔芋多糖为底物，加入本团队自主生产的魔芋多糖水解酶或者爱尔兰Megazyme公司的endo-1,4β-Mannanase(Cellvibriojaponicus)，以酶：底物＝1:9的比例对底物进行降解，于25℃反应。酶解液进行冻干处理，得到魔芋葡甘寡糖(重均分子量340-10000Da的)，其质谱图见附图1。
实施例1硒化魔芋葡甘寡糖的制备
取0.5g魔芋葡甘寡糖加入到50mL的0.5％的硝酸水溶液中，搅拌溶解；加入0.61g亚硒酸钠，0.86g氯化钡，搅拌溶解；将溶液于70℃反应9小时；加入0.5g硫酸钠，8000rpm离心去除沉淀；上清液用碳酸氢钠中和至中性；将反应液加入5倍体积乙醇，产生大量白色沉淀；抽滤得到固体，至于真空干燥器中60℃干燥，得白色粉末硒化魔芋葡甘寡糖。
将硒化魔芋葡甘寡糖进行红外光谱分析(见附图2)，在740cm-1处有明显的吸收峰，为亚硒酸酯吸收峰，说明魔芋葡甘寡糖上发生了硒化反应。经ICP-MS分析，硒化魔芋葡甘寡糖中硒的含量为5.9g/Kg。
实施例2硒化魔芋葡甘寡糖的制备
取0.5g实施例1的魔芋葡甘寡糖加入到50mL的0.5％的磷酸水溶液中，搅拌溶解；加入0.81g亚硒酸钠，0.86g氯化钡，搅拌溶解；将溶液于80℃反应6小时；加入0.5g硫酸钾，8000rpm离心去除沉淀；上清液用碳酸钠中和至中性；将反应液加入6倍体积乙醇，产生大量白色沉淀；抽滤得到固体，至于真空干燥器中40℃干燥，得白色粉末硒化魔芋葡甘寡糖。
将硒化魔芋葡甘寡糖进行红外光谱分析，在740cm-1处有明显的吸收峰，为亚硒酸酯吸收峰，说明魔芋葡甘寡糖上发生了硒化反应。经ICP-MS分析，硒化魔芋葡甘寡糖中硒的含量为6.1g/Kg。
实施例3硒化魔芋葡甘寡糖的制备
取0.5g实施例1的魔芋葡甘寡糖加入到50mL的1.0％的盐酸水溶液中，搅拌溶解；加入0.821g硒酸钠，0.91g氯化钙，搅拌溶解；将溶液于60℃反应10小时；加入0.5g硫酸钾，8000rpm离心去除沉淀；上清液用氢氧化钠中和至中性；将反应液加入3倍体积乙醇，产生大量白色沉淀；抽滤得到固体，至于真空干燥器中60℃干燥，得白色粉末硒化魔芋葡甘寡糖。
将硒化魔芋葡甘寡糖进行红外光谱分析，在741cm-1处有明显的吸收峰，为亚硒酸酯吸收峰，说明魔芋葡甘寡糖上发生了硒化反应。经ICP-MS分析，硒化魔芋葡甘寡糖中硒的含量为4.8g/Kg。
实施例4硒化魔芋葡甘寡糖的制备
取0.5g实施例1的魔芋葡甘寡糖加入到50mL的2％的醋酸水溶液中，搅拌溶解；加入0.61g亚硒酸钾，0.86g氯化钡，搅拌溶解；将溶液于90℃反应10小时；加入0.5g硫酸钠，10000rpm离心去除沉淀；上清液用碳酸氢钠中和至中性；将反应液加入5倍体积乙醇，产生大量白色沉淀；抽滤得到固体，至于真空干燥器中60℃干燥，得白色粉末硒化魔芋葡甘寡糖。
将硒化魔芋葡甘寡糖进行红外光谱分析，在740cm-1处有明显的吸收峰，为亚硒酸酯吸收峰，说明魔芋葡甘寡糖上发生了硒化反应。经ICP-MS分析，硒化魔芋葡甘寡糖中硒的含量为4.2g/Kg。
实施例5硒化魔芋葡甘寡糖的抗炎活性
抗炎实验：对炎症因子的抑制作用
实验材料：内皮细胞株，实施例1制备的硒化魔芋葡甘寡糖，TNF-α
细胞培养条件：在完全培养基RPMI1640培养液中添加10％小牛血清、100U/mL青霉素、100μug/mL链霉素；37℃，CO2体积含量为5％的细胞培养箱培养。
药物处理如下：
收集对数生长期细胞，调整细胞培养密度为1-2×106个/mL分到细胞培养六孔板中，加入(100mg/mL及200mg/mL)的实施例1的硒化魔芋葡甘寡糖处理24小时后，再加入TNF-α(20ng/mL)，处理6小时。随后弃去细胞培养上清，提取细胞RNA，进行逆转录PCR，扩增条件为：94℃，45秒，54℃，45秒,72℃,45秒，扩增28个循环以检测白细胞介素-6(IL-6)基因水平的变化。实验结果表明，相比于未处理组，100mg/mL及200mg/mL的硒化魔芋葡甘寡糖使IL-6的生成量降低了19％及28％。实验结果说明硒化魔芋葡甘寡糖可以降低炎症因子IL-6的产生，具有抗炎活性。
实施例6硒化魔芋葡甘寡糖的抗肿瘤活性
实验材料：肝癌细胞株，实施例2制备的硒化魔芋葡甘寡糖。
细胞培养条件:在完全培养基DMEM培养液中添加10％小牛血清、100U/mL青霉素、100μg/mL链霉素；37℃，CO2体积含量为5％的细胞培养箱培养。药物处理：
收集对数生长期细胞，调整细胞密度为1-2×106个/mL，分别加入200mg/mL及400mg/mL的硒化魔芋葡甘寡糖处理24小时后，采用碘化丙锭(PI)染色法检测细胞凋亡情况。具体操作为：收集各组处理后的细胞，弃去培养液；用PBS洗涤2次；随后离心弃去上清，加入冰预冷的70％的乙醇固定2小时。随后再次离心弃去固定液，PBS洗涤2遍再加入PI染液染色，4℃避光染色30分钟，通过流式细胞仪检测细胞凋亡。实验结果表明，相比于未处理组，100mg/mL及200mg/mL的硒化魔芋葡甘寡糖的肝癌细胞凋亡增加63％及82％。实验结果说明，硒化魔芋葡甘寡糖可促使肝癌细胞凋亡增加，从而发挥抗癌作用效果。
实施例7硒化魔芋葡甘寡糖的清除自由基活性
抗氧化实验：DPPH自由基清除实验。
实验材料：二苯代苦味酰自由基(DPPH)，实施例3制备的硒化魔芋葡甘寡糖。
试剂配制：DPPH应用液，称取DPPH3.5mg，溶于甲醇10ml，再加水定溶至100mL，充分混匀后避光保存。
取4支试管，分别标记为空白对照组，200mg/mL和400mg/mL硒化魔芋葡甘寡糖实验组及维生素C阳性对照组。分别加入0.1mL甲醇,200ng/mL硒化魔芋葡甘寡糖的甲醇溶液及400ng/ml硒化魔芋葡甘寡糖的甲醇溶液及100μg/ml维生素C甲醇溶液。随后，分别加入200μL的DPPH溶液，摇匀，在黑暗中放置30分钟，以甲醇组为空白对照组在515nm分别测定各组吸光度。实验结果表明，200mg/mL的硒化魔芋葡甘寡糖清除自由基为65％，而400mg/mL的硒化魔芋葡甘寡糖对自由基的清除能力与100μg/mL维生素C效果相当，清除率为80％。实验结果说明，400mg/mL的硒化魔芋葡甘寡糖具有良好的自由基清除效果。
实施例8硒化魔芋葡甘寡糖的抗衰老活性
实验材料：成纤维细胞，实施例1制备的硒化魔芋葡甘寡糖
实验方法：成纤维细胞在完全培养基DMEM培养液中添加10％小牛血清、100U/mL青霉素、100μg/mL链霉素；37℃，CO2体积含量为5％的细胞培养箱培养。
主要操作如下：收集对数生长期细胞，调整细胞密度为1-2×104个/孔接种于6孔板，2mL培养液，分别加入空白组生理盐水，100μg/ml的硒化魔芋葡甘寡糖生理盐水溶液及200μg/mL的硒化魔芋葡甘寡糖生理盐水溶液处理24小时后，紫外光UVB为光源290nm，照射剂量为10mJ/cm2，共计照射5次。随后采用SAβ-gal染色试剂盒检测。室温下用1mL固定液固定细胞15min，再以染色液37℃孵育过夜。阳性细胞被染成蓝绿色，显微镜下计数SAβ-gal染色阳性的细胞，每皿计数400个，计算阳性细胞的百分比。实验结果表明，空白照射组阳性细胞数为82％，100μg/mL的硒化魔芋葡甘寡糖处理组使阳性细胞数降低到55％，200μg/mL的硒化魔芋葡甘寡糖处理组使阳性细胞数降低到42％。实验结果说明，不同浓度的硒化魔芋葡甘寡糖可使紫外线诱导的衰老细胞数降低，从而具有抗衰老潜能。
Claims (10)
1.一种硒化魔芋葡甘寡糖，其特征在于：所述硒化魔芋葡甘寡糖的重均分子量为350-10000Da，主链由葡萄糖基和甘露糖基以β-1,4糖苷键连结；硒以亚硒酸酯的形式连接在葡萄糖基或甘露糖基的C6和/或C2和/或C3位；硒的含量为0.2-1.5％(w/w)。
2.一种权利要求1所述的硒化魔芋葡甘寡糖的制备方法，其特征在于：包括以下步骤：
(1)将魔芋葡甘寡糖加入酸性水溶液中，再依加入硒化试剂、催化剂，在20-90℃下反应2-12小时，得溶液A；
(2)向所述溶液A中加入硫酸盐，得混合物，离心处理所述混合物；上清液用碱中和至中性，得溶液B；
(3)向所述溶液B中加入有机醇，得沉淀物；抽滤沉淀物得到固体，将所述固体真空干燥，得到所述硒化魔芋葡甘寡糖。
3.根据权利要求2所述硒化魔芋葡甘寡糖的制备方法，其特征在于：
所述步骤(1)中，硒化试剂为亚硒酸钠、亚硒酸钾、硒酸钠、硒酸钾中的至少一种，硒化试剂的加入量以硒的摩尔数计，为魔芋葡甘寡糖糖残基摩尔数的0.5-3倍；优选亚硒酸钠、亚硒酸钾；催化剂为氯化钡、氯化钙中的至少一种，催化剂的加入量为魔芋葡甘寡糖糖残基摩尔数的0.5-1.5倍；优选氯化钡。
4.根据权利要求2所述硒化魔芋葡甘寡糖的制备方法，其特征在于：
所述步骤(1)中，魔芋葡甘寡糖的质量含量为酸性水溶液的0.5-20％。
5.根据权利要求2所述硒化魔芋葡甘寡糖的制备方法，其特征在于：
所述步骤(1)中，酸性水溶液为硝酸、硫酸、盐酸、醋酸、磷酸中的至少一种，酸的质量含量为0.2-2％；优选硝酸。
6.根据权利要求2所述硒化魔芋葡甘寡糖的制备方法，其特征在于：
所述步骤(2)中，离心处理的转速为4000-8000rpm。
7.根据权利要求2所述硒化魔芋葡甘寡糖的制备方法，其特征在于：
所述步骤(2)中，硫酸盐为硫酸钠、硫酸钾、硫酸铵、硫酸氢钠、硫酸氢钾中的至少一种，硫酸盐加入量为魔芋葡甘寡糖糖残基摩尔数的1-1.5倍。
8.根据权利要求2所述硒化魔芋葡甘寡糖的制备方法，其特征在于：
所述步骤(2)中，碱为碳酸氢钠、碳酸钠、碳酸氢钾、碳酸钾、氢氧化钠、氢氧化钾中的至少一种。
9.根据权利要求2所述硒化魔芋葡甘寡糖的制备方法，其特征在于：
所述步骤(3)中，有机醇为乙醇、甲醇、异丙醇中的至少一种，有机醇的加入量为溶液B体积的3-8倍；优选乙醇；真空干燥的温度为30-80℃，时间为1-3小时。
10.权利要求1所述硒化魔芋葡甘寡糖的应用，其特征在于：
所述硒化魔芋葡甘寡糖作为活性成份用于延缓衰老保健食品、抑制肿瘤保健药物、抗炎症药物或抗氧化食品。
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