4-O-galloyl-1,5-anhydro-D-glucitol | 1355573-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-O-galloyl-1,5-anhydro-D-glucitol
• 英文别名: maplexin B；[(2R,3S,4R,5S)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 1355573-80-6
• 化学式: C₁₃H₁₆O₉
• 分子量: 316.265
• InChiKey: RLDCPODFUAIPRT-LUTQBAROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-O-galloyl-1,5-anhydro-D-glucitol 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 1,5-无水葡萄糖醇
  参考文献：
  名称：

  Maplexins, new α-glucosidase inhibitors from red maple (Acer rubrum) stems

  摘要：

  Thirteen gallic acid derivatives including five new gallotannins, named maplexins A-E, were isolated from red maple (Acer rubrum) stems. The compounds were identified by spectral analyses. The maplexins varied in number and location of galloyl groups attached to 1,5-anhydro-D-glucitol. The isolates were evaluated for a-glucosidase inhibitory and antioxidant activities. Maplexin E, the first compound identified with three galloyl groups linked to three different positions of 1,5-anhydro-D-glucitol, was 20 fold more potent than the a-glucosidase inhibitory drug, Acarbose (IC50 = 8 vs 160 mu M). Structure-activity related studies suggested that both number and position of galloyls attached to 1,5-anhydro-D-glucitol were important for a-glucosidase inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.073
• 作为产物：
  描述：

  1,5-anhydro-4,6-O-benzylidene-D-glucitol 在 三乙基硅烷 、 4-二甲氨基吡啶 、 palladium hydroxide, 20 wt% on carbon 、 2-氯-1-甲基吡啶碘化物 、 氢气 、 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 4-O-galloyl-1,5-anhydro-D-glucitol
  参考文献：
  名称：

  Synthesis and Comparative Structure–Activity Study of Carbohydrate-Based Phenolic Compounds as α-Glucosidase Inhibitors and Antioxidants

  摘要：

  合成了二十一种含有碳水化合物基团的天然和非天然酚类化合物，并评估了它们在α-葡萄糖苷酶抑制和抗氧化活性方面的结构-活性关系（SAR）。在1,5-脱氧-D-葡萄糖醇（1,5-AG）核心上改变没食子酸单元的位置导致了α-葡萄糖苷酶抑制活性的变化，特别是当没食子酸单元位于C-2位置时表现出明显的强活性。此外，增加没食子酸单元的数量显著影响了α-葡萄糖苷酶抑制作用，2,3,4,6-四没食子酸-1,5-AG（54）和2,3,4,6-四没食子酸-D-葡萄糖吡喃糖（61）表现出卓越的活性，其α-葡萄糖苷酶抑制活性比没食子酸（37）高出13倍以上。此外，一项比较结构-活性研究表明，碳水化合物核心中的半缩醛羟基官能团和4,6-O-六羟基二苯甲酰（HHDP）单元的双芳基键，包括tellimagrandin I在内的椰子酸鞣质并不是α-葡萄糖苷酶抑制活性所必需的。最后，抗氧化活性随没食子酸单元数量的增加而成比例增加。

  DOI：

  10.3390/molecules24234340

文献信息

• MAPLE TREE-DERIVED PRODUCTS AND USES THEREOF
  申请人：Barbeau Julie

  公开号：US20130310332A1

  公开（公告）日：2013-11-21

  The present document describes a neutraceutical, cosmeceuticals, functional food, pharmaceutical, food ingredient, and non-food ingredient compositions comprising sugar maple extract, essential oil compositions comprising oil extracted from an Acer tree, sweetening compositions containing sugar extracted from maple tree leaves, food ingredients comprising maple tree extract, cosmetic composition comprising maple tree extracts, infusion compositions prepared from maple tree leaves, maple roots, maple wood, maple stems of leaves and samara, and stems/twigs as well as compounds isolated from sugar maple biomass and the methods of extracting the same.
• [EN] CERAMIDE CONTENT INCREASING AGENTS<br/>[FR] AGENTS AUGMENTANT LA TENEUR EN CÉRAMIDES<br/>[JA] セラミド含量増加剤
  申请人：NAT UNIV CORP UNIV OF TOYAMA

  公开号：WO2017122495A1

  公开（公告）日：2017-07-20

  式(I)で表される化合物又はその医薬上許容される塩からなるセラミド分解酵素阻害剤、式(II)で表される化合物又はその医薬上許容される塩からなるセラミド合成促進剤。本発明のセラミド分解酵素阻害剤及びセラミド合成促進剤は、細胞又は皮膚におけるセラミド量を増加するため、例えば、保湿効果、シワの改善、アトピー性皮膚炎の症状改善、乾皮症の予防／改善、シミの予防、肌のタルミの改善、抗掻痒作用、メラニン生成抑制効果、バリア機能の向上、繊維芽細胞賦活効果、皮膚細胞の再生効果のために好適に用いられる。
• Synthesis and Comparative Structure–Activity Study of Carbohydrate-Based Phenolic Compounds as α-Glucosidase Inhibitors and Antioxidants
  作者：Shota Machida、Saki Mukai、Rina Kono、Megumi Funato、Hiroaki Saito、Taketo Uchiyama

  DOI：10.3390/molecules24234340

  日期：——

  Twenty-one natural and unnatural phenolic compounds containing a carbohydrate moiety were synthesized and their structure–activity relationship (SAR) was evaluated for α-glucosidase inhibition and antioxidative activity. Varying the position of the galloyl unit on the 1,5-anhydro-d-glucitol (1,5-AG) core resulted in changes in the α-glucosidase inhibitory activity and notably, particularly strong activity was demonstrated when the galloyl unit was present at the C-2 position. Furthermore, increasing the number of the galloyl units significantly affected the α-glucosidase inhibition, and 2,3,4,6-tetra-galloyl-1,5-AG (54) and 2,3,4,6-tetra-galloyl-d-glucopyranose (61) exhibited excellent activities, which were more than 13-fold higher than the α-glucosidase inhibitory activity of acertannin (37). Moreover, a comparative structure-activity study suggested that a hemiacetal hydroxyl functionality in the carbohydrate core and a biaryl bond of the 4,6-O-hexahydroxydiphenoyl (HHDP) group, which are components of ellagitannins including tellimagrandin I, are not necessary for the α-glucosidase inhibitory activity. Lastly, the antioxidant activity increased proportionally with the number of galloyl units.

  合成了二十一种含有碳水化合物基团的天然和非天然酚类化合物，并评估了它们在α-葡萄糖苷酶抑制和抗氧化活性方面的结构-活性关系（SAR）。在1,5-脱氧-D-葡萄糖醇（1,5-AG）核心上改变没食子酸单元的位置导致了α-葡萄糖苷酶抑制活性的变化，特别是当没食子酸单元位于C-2位置时表现出明显的强活性。此外，增加没食子酸单元的数量显著影响了α-葡萄糖苷酶抑制作用，2,3,4,6-四没食子酸-1,5-AG（54）和2,3,4,6-四没食子酸-D-葡萄糖吡喃糖（61）表现出卓越的活性，其α-葡萄糖苷酶抑制活性比没食子酸（37）高出13倍以上。此外，一项比较结构-活性研究表明，碳水化合物核心中的半缩醛羟基官能团和4,6-O-六羟基二苯甲酰（HHDP）单元的双芳基键，包括tellimagrandin I在内的椰子酸鞣质并不是α-葡萄糖苷酶抑制活性所必需的。最后，抗氧化活性随没食子酸单元数量的增加而成比例增加。
• Maplexins, new α-glucosidase inhibitors from red maple (Acer rubrum) stems
  作者：Chunpeng Wan、Tao Yuan、Liya Li、Vamsikrishna Kandhi、Nadja B. Cech、Mingyong Xie、Navindra P. Seeram

  DOI：10.1016/j.bmcl.2011.10.073

  日期：2012.1

  Thirteen gallic acid derivatives including five new gallotannins, named maplexins A-E, were isolated from red maple (Acer rubrum) stems. The compounds were identified by spectral analyses. The maplexins varied in number and location of galloyl groups attached to 1,5-anhydro-D-glucitol. The isolates were evaluated for a-glucosidase inhibitory and antioxidant activities. Maplexin E, the first compound identified with three galloyl groups linked to three different positions of 1,5-anhydro-D-glucitol, was 20 fold more potent than the a-glucosidase inhibitory drug, Acarbose (IC50 = 8 vs 160 mu M). Structure-activity related studies suggested that both number and position of galloyls attached to 1,5-anhydro-D-glucitol were important for a-glucosidase inhibition. (C) 2011 Elsevier Ltd. All rights reserved.