3-O-galloyl-D-glucose

• 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: 3-O-galloyl-D-glucose
• 英文别名: [(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl] 3,4,5-trihydroxybenzoate
• 化学式: C₁₃H₁₆O₁₀
• 分子量: 332.264
• InChiKey: MWEAKAFRGMFWAV-RREHWXIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  23
• 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：
  177
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,4,5-tris(benzyloxy)benzoyl chloride 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 11.83h， 生成 3-O-galloyl-D-glucose
  参考文献：
  名称：

  Synthesis of gallotannins

  摘要：

  As a contribution to the synthesis of gallotannins, four O-galloyl-D-glucoses (3-O-, 6-O-, 3,6-di-O-, 3,4,6-tri-O-galloyl-D-glucose) have been prepared by the reaction of tri-O-benzylgalloyl chloride and partially protected glucose derivatives (1,2-O-, and 1,2:5,6-di-O-isopropylidene-alpha -D-glucofuranose), followed successively by catalytic debenzylation (Pd-C) and controlled acid hydrolysis. Their structures were established from their behavior on TLC and from their H-1 and C-13 NMR spectra. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00236-1

文献信息

• Camptothins A and B, new dimeric hydrolyzable tannins from Camptotheca acuminata DECNE.
  作者：TSUTOMU HATANO、YUKIHIKO IKEGAMI、TETSURO SHINGU、TAKUO OKUDA

  DOI：10.1248/cpb.36.2017

  日期：——

  Two new hydrolyzable tannins, named camptothins A (1) and B (4), have been isolated from the leaf of Camptotheca acuminata (Nyssaceae) along with cornusiin A (2), gemin D (3), tellimagrandin I (5), tellimagrandin II (6), 1, 2, 6-tri-ο-galloyl-β-D-glucose (7) and 1, 2, 3, 6-tetra-ο-galloyl-β-D-glucose (8). Pedunculagin (9) was isolated from the fruit of C. acuminata. The dimeric structures of camptothins A and B have been established based on chemical and spectroscopic evidence.

  从夹竹桃科的夹竹桃（Camptotheca acuminata）叶中分离出了两种新的可水解单宁，命名为camptothins A (1) 和 B (4)，同时还分离出了cornusiin A (2)、gemin D (3)、tellimagrandin I (5)、tellimagrandin II (6)、1, 2, 6-三-Ο-没食子酸基-β-D-葡萄糖 (7) 和 1, 2, 3, 6-四-Ο-没食子酸基-β-D-葡萄糖 (8)。pedunculagin (9) 是从夹竹桃果实中分离出的。根据化学和光谱证据，已确定了camptothins A 和 B 的二聚体结构。
• Tannins of cornaceous plants. I. Cornusiins A, B and C, dimeric monomeric and trimeric hydrolyzable tannins from Cornus officinalis, and orientation of valoneoyl group in related tannins.
  作者：Tsutomu HATANO、Noboru OGAWA、Reiko KIRA、Taeko YASUHARA、Takuo OKUDA

  DOI：10.1248/cpb.37.2083

  日期：——

  Cornusiin A (1), cornusiin B (2) and cornusiin C (3), new dimeric monomeric and trimeric hydrolyzable tannins, were isolated from the fruits of cornus officinalis (Cornaceae). Their structures, including the orientation of the valoneoyl group in 1 and 3, were established on the basis of chemical and spectroscopic data. 2, 3-Di-O-galloyl-D-glucose (7), 1, 2, 3-tri-O-galloyl-β-D-glucose, 1, 2, 6-tri-O-galloyl-β-D-glucose, 1, 2, 3, 6-tetra-O-galloyl-β-D-glucose, gemin D (5), isoterchebin, tellimagrandin I (6) and tellimagrandin II were also isolated from the fruits. The orientation of the valoneoyl group in camptothin A (14) and that in camptothin B (15), which had been isolated from Camptotheca acuminata (Nyssaceae), were also determined based on that in 1.

  从 Cornus officinalis（山茱萸科）的果实中分离出了新型二聚单体和三聚水解鞣花酸，分别为 Cornusiin A (1)、Cornusiin B (2) 和 Cornusiin C (3)。它们的结构，包括 1 和 3 中 valoneoyl 基团的取向，是基于化学和光谱数据确定的。此外，还从果实中分离出了 2, 3-二-O-没食子酸-D-葡萄糖 (7)、1, 2, 3-三-O-没食子酸-β-D-葡萄糖、1, 2, 6-三-O-没食子酸-β-D-葡萄糖、1, 2, 3, 6-四-O-没食子酸-β-D-葡萄糖、gemin D (5)、isoterchebin、tellimagrandin I (6) 和 tellimagrandin II。Camptotheca acuminata（黄樟科）中分离出的 camptothin A (14) 和 camptothin B (15) 中 valoneoyl 基团的取向也是基于 1 的取向确定的。
• Tannins and Related Polyphenols of Lythraceous Plants. Part2. Woodfordin D and Oenothein A, Trimeric Hydrolyzable Tannins of Macro-Ring Structure with Antitumor Activity.
  作者：Takashi YOSHIDA、Tong CHOU、Muneto MATSUDA、Taeko YASUHARA、Kazufumi YAZAKI、Tsutomu HATANO、Aya NITTA、Takuo OKUDA

  DOI：10.1248/cpb.39.1157

  日期：——

  trimeric hydrolyzable tannins, woodfordin D (5) and oenothein A (13), were isolated from the dried flowers of Woodfordia fruticosa, and their macrocyclic structures, which have a novel constituent unit (woodfordinoyl group) connecting the monomers, have been elucidated on the basis of spectral and chemical evidence. Oenothein A (13) was also isolated from the leaves of Oenothera biennis.

  从桔梗的干燥花中分离出两种新的抗肿瘤三聚体可水解单宁，伍德福德D（5）和卵磷脂A（13），它们的大环结构具有连接单体的新组成单元（伍德福德基）。根据光谱和化学证据进行了阐明。还从月见草的叶子中分离出Oenothein A（13）。
• Tannins and related compounds. XCV. Isolation and characterization of helioscopinins and helioscopins, four new hydrolyzable tannins from Euphorbia helioscopia L. (1).
  作者：Seung-Ho LEE、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.38.1518

  日期：——

  A chemical examination of polyphenols in Euphorbia helioscopia L. (Euphorbiaceae) has led to the isolation of four new hydrozable tannins named helioscopinins A (10) and B (9), and helioscopins A (11) and B (12), together with eight known tannins (1-8). On the basis of chemical and spectroscopic evidence, the structures of compounds 9-12 were established as 1, 6-(S)-hexahydroxydiphenoyl-3-O-galloyl-β-D-glucose, 1, 6-(S)-hexahydroxydiphenoyl-2, 4-(S)-dehydrohexahydroxydiphenoyl-3-O-galloyl-β-D-glucose, 1, 6-(S)-hexahydroxydiphenoyl-2, 4-(R)-elaeocarpusionoyl-3-O-galloyl-β-D-glucose and 1, 3, 6-tri-O-galloyl-2, 4-(R)-elaeocarpusinoyl-β-D-glucose, respectively.

  对大戟科植物日照大戟（Euphorbia helioscopia L.）中的多酚进行了化学分析，分离出四种新的水解鞣酸，分别命名为helioscopinins A (10) 和 B (9)，以及helioscopins A (11) 和 B (12)，同时还发现了八种已知的鞣酸（1-8）。根据化学和光谱证据，化合物9-12的结构被确认分别为：1, 6-(S)-六羟基二苯酰基-3-O-鞣酸基-β-D-葡萄糖，1, 6-(S)-六羟基二苯酰基-2, 4-(S)-脱氢六羟基二苯酰基-3-O-鞣酸基-β-D-葡萄糖，1, 6-(S)-六羟基二苯酰基-2, 4-(R)-油青果酸-3-O-鞣酸基-β-D-葡萄糖和1, 3, 6-三-O-鞣酸基-2, 4-(R)-油青果酸-β-D-葡萄糖。
• Woodfordin C, a macro-ring hydrolyzable tannin dimer with antitumor activity, and accompanying dimers from Woodfordia fruticosa flowers.
  作者：Takashi YOSHIDA、Tong CHOU、Aya NITTA、Ken-ichi MIYAMOTO、Ryozo KOSHIURA、Takuo OKUDA

  DOI：10.1248/cpb.38.1211

  日期：——

  Three new dimeric hydrolyzable tannins, woodfordins A, B and C, along with seven known hydrolyzable tannins, including oenothein B, a dimer exhibiting marked host-mediated antitumor activity, were isolated from an Indonesian crude drug, Sidowayah [dried flowers of Woodfordia fruticosa (L.) Kurz (Lythraceae)]. The structures of the new tannins were elucidated based on chemical and spectral evidence

  从印尼粗制药物Sidowayah中分离了三种新的二聚体可水解单宁，伍德福德素A，B和C，以及7种已知的可水解单宁，其中Oenothein B是一种具有明显的宿主介导的抗肿瘤活性的二聚体。 L.）Kurz（Lythraceae）]。基于化学和光谱证据阐明了新单宁的结构。具有大环结构的Woodfordin C也被发现具有显着的抗肿瘤活性。