Masaki Fujishima, K. Furuyama, Yojiro Ishihiro, S. Onodera, E. Fukushi, N. Benkeblia, N. Shiomi
Fructooligosaccharides are involved in physiological activities and quality attributes of onion bulbs. This work describes structures of newly synthesized oligosaccharides formed by fructose moieties in onion bulb tissues during storage. Onion bulbs were stored for four weeks at 10 ∘ C . HPAEC-PAD analysis showed that saccharide 1 was eluted after 1-kestose while saccharide 2 was eluted after nystose ( 𝟒 a ) . Saccharides 1 and 2 have R-sucrose values of 1.55 and 2.15 by HPAEC, a reducing terminal, a reducing sugar-to-fructose ratio of 0.5 and 0.3, and a degree of polymerization of 2 and 3 by TOF-MS, respectively. GLC analysis of the methyl derivatives and NMR measurement of the saccharides confirmed the presence of two different structures: the structure of saccharide 1 is composed by two fructose moieties and linked by 𝛽 ( 2 → 1 ) linkage and was identified as inulobiose [ 𝛽 -D-fructofuranosyl- ( 2 → 1 ) - 𝛽 -D-fructopyranose]. The structure of saccharide 2 consists of three units of fructose linked by 𝛽 ( 2 → 1 ) linkage and was identified as inulotriose [ 𝛽 -D-fructofuranosyl- ( 2 → 1 ) - 𝛽 -D-fructofuranosyl- ( 2 → 1 ) - 𝛽 -D-fructopyranose]. The spectra also showed that 70 to 80% of the terminal fructose residue of the two saccharides is of pyranosyl form, while 20 to 30% is of furanosyl form. This finding demonstrated that these newly produced saccharides, catalyzed by onion-purified 6G-FFT, were synthesized by the action of 1-FFT fructosyltransfer from 1-kestose to free fructopyranose yielding inulobiose and sucrose, while elongation of fructofuranosyl units occurs at this transferred fructofuranosyl residue to produce inulooligosaccharide having an additional unit of fructofuranose.
低聚果糖参与洋葱鳞茎的生理活性和品质特性。本文描述了贮藏过程中洋葱鳞茎组织中果糖部分形成的新合成的低聚糖的结构。洋葱球茎在10°C下贮存4周。HPAEC-PAD分析显示糖1在1-kestose后洗脱，糖2在nystose后洗脱(𝟒a)。糖1和糖2 HPAEC的r-蔗糖值分别为1.55和2.15，还原糖果糖比分别为0.5和0.3,TOF-MS的聚合度分别为2和3。甲基衍生物的GLC分析和核磁共振测量证实了糖的两种不同结构的存在:糖1的结构由两个果糖部分组成，并通过(2→1)键连接，被鉴定为吲哚糖[ - d -聚呋喃基-(2→1)- d -聚吡喃糖]。糖2的结构由3个单位的果糖组成，并以(2→1)键连接，被确定为inulotriose [ - d -聚呋喃基-(2→1)- - d -聚呋喃基-(2→1)- - d -聚呋喃基-(2→1)]。光谱还表明，两种糖的末端果糖残基中有70 ~ 80%为吡喃糖基形式，20 ~ 30%为呋喃糖基形式。这一发现表明，在洋葱纯化的6G-FFT催化下，这些新生产的糖是通过1-FFT从1-酮糖到游离果糖吡喃糖的转移合成的，产生了菊糖和蔗糖，而在这个转移的果糖呋喃基残基上发生了果糖呋喃基单位的延伸，产生了含有额外单位果糖呋喃糖的菊糖低聚糖。
{"title":"Isolation and Structural Analysis In Vivo of Newly Synthesized Fructooligosaccharides in Onion Bulbs Tissues (Alliumcepa L.) during Storage","authors":"Masaki Fujishima, K. Furuyama, Yojiro Ishihiro, S. Onodera, E. Fukushi, N. Benkeblia, N. Shiomi","doi":"10.1155/2009/493737","DOIUrl":"https://doi.org/10.1155/2009/493737","url":null,"abstract":"Fructooligosaccharides are involved in physiological activities and quality attributes of onion bulbs. This work describes structures of newly synthesized oligosaccharides formed by fructose moieties in onion bulb tissues during storage. Onion bulbs were stored for four weeks at 10 ∘ C . HPAEC-PAD analysis showed that saccharide 1 was eluted after 1-kestose while saccharide 2 was eluted after nystose ( 𝟒 a ) . Saccharides 1 and 2 have R-sucrose values of 1.55 and 2.15 by HPAEC, a reducing terminal, a reducing sugar-to-fructose ratio of 0.5 and 0.3, and a degree of polymerization of 2 and 3 by TOF-MS, respectively. GLC analysis of the methyl derivatives and NMR measurement of the saccharides confirmed the presence of two different structures: the structure of saccharide 1 is composed by two fructose moieties and linked by 𝛽 ( 2 → 1 ) linkage and was identified as inulobiose [ 𝛽 -D-fructofuranosyl- ( 2 → 1 ) - 𝛽 -D-fructopyranose]. The structure of saccharide 2 consists of three units of fructose linked by 𝛽 ( 2 → 1 ) linkage and was identified as inulotriose [ 𝛽 -D-fructofuranosyl- ( 2 → 1 ) - 𝛽 -D-fructofuranosyl- ( 2 → 1 ) - 𝛽 -D-fructopyranose]. The spectra also showed that 70 to 80% of the terminal fructose residue of the two saccharides is of pyranosyl form, while 20 to 30% is of furanosyl form. This finding demonstrated that these newly produced saccharides, catalyzed by onion-purified 6G-FFT, were synthesized by the action of 1-FFT fructosyltransfer from 1-kestose to free fructopyranose yielding inulobiose and sucrose, while elongation of fructofuranosyl units occurs at this transferred fructofuranosyl residue to produce inulooligosaccharide having an additional unit of fructofuranose.","PeriodicalId":13788,"journal":{"name":"International Journal of Carbohydrate Chemistry","volume":"8 1","pages":"493737-1-493737-9"},"PeriodicalIF":0.0,"publicationDate":"2009-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88317014","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Molecular dynamics (MD) simulations were used to monitor the stability and conformation of double-stranded and single-stranded amyloses and single-stranded cellulose oligomers containing 9 sugar moieties in solution as a function of solvent composition, ionic strength, temperature, and methylation state. This study along with other previous studies suggests that hydrogen bonds are crucial for guaranteeing the stability of the amylose double helix. Single-stranded amylose forms a helical structure as well, and cellulose stays highly elongated throughout the simulation time, a behavior that was also observed experimentally. In terms of coordination of solute hydroxyl groups with ions, amylose shows entropy-driven coordination of calcium and sulfate ions, whereas cellulose-ion coordination seems to be enthalpy-dominated. This indicates that entropy considerations cannot be neglected when explaining the structural differences between amyloses and celluloses.
{"title":"On the Conformational Properties of Amylose and Cellulose Oligomers in Solution","authors":"M. Winger, M. Christen, W. V. Gunsteren","doi":"10.1155/2009/307695","DOIUrl":"https://doi.org/10.1155/2009/307695","url":null,"abstract":"Molecular dynamics (MD) simulations were used to monitor the stability and conformation of double-stranded and single-stranded amyloses and single-stranded cellulose oligomers containing 9 sugar moieties in solution as a function of solvent composition, ionic strength, temperature, and methylation state. This study along with other previous studies suggests that hydrogen bonds are crucial for guaranteeing the stability of the amylose double helix. Single-stranded amylose forms a helical structure as well, and cellulose stays highly elongated throughout the simulation time, a behavior that was also observed experimentally. In terms of coordination of solute hydroxyl groups with ions, amylose shows entropy-driven coordination of calcium and sulfate ions, whereas cellulose-ion coordination seems to be enthalpy-dominated. This indicates that entropy considerations cannot be neglected when explaining the structural differences between amyloses and celluloses.","PeriodicalId":13788,"journal":{"name":"International Journal of Carbohydrate Chemistry","volume":"10 1","pages":"1-8"},"PeriodicalIF":0.0,"publicationDate":"2009-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84300243","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Sialidase is a ubiquitous enzyme that catalyzes the hydrolytic removal of terminal sialic acid residues from oligosaccharides in glycolipids and glycoproteins. Ganglioside GM1 has been usually found to be resistant to various sialidases. Arthrobacter ureafaciens sialidase has been reported to remove sialyl residues of ganglioside GM1 in the presence of bile salts. However, bile salts are difficult to be removed, and disturb HPTLC analysis. Using -cyclodextrin (-CD) as a novel additive agent, ganglioside GM1 was efficiently hydrolyzed to asialo-GM1 by A. ureafaciens sialidase.
{"title":"-Cyclodextrin Increases Hydrolysis of Gangliosides by Sialidase from Arthrobacter ureafaciens: Hydrolysis of Gangliosides","authors":"Rie Mitsumori, Tomohisa Kato, K. Hatanaka","doi":"10.1155/2009/398284","DOIUrl":"https://doi.org/10.1155/2009/398284","url":null,"abstract":"Sialidase is a ubiquitous enzyme that catalyzes the hydrolytic removal of terminal sialic acid residues from oligosaccharides in glycolipids and glycoproteins. Ganglioside GM1 has been usually found to be resistant to various sialidases. Arthrobacter ureafaciens sialidase has been reported to remove sialyl residues of ganglioside GM1 in the presence of bile salts. However, bile salts are difficult to be removed, and disturb HPTLC analysis. Using -cyclodextrin (-CD) as a novel additive agent, ganglioside GM1 was efficiently hydrolyzed to asialo-GM1 by A. ureafaciens sialidase.","PeriodicalId":13788,"journal":{"name":"International Journal of Carbohydrate Chemistry","volume":"9 1","pages":"1-4"},"PeriodicalIF":0.0,"publicationDate":"2009-02-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75135156","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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