1,6-di-O-galloyl-β-D-glucopyranose | 23363-08-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 1,6-di-O-galloyl-β-D-glucopyranose
• 英文别名: 1,6-di-O-galloyl-β-D-glucose；1,6-Digalloyl glucopyranose；1,6-di-O-galloyl-β-glucose；1,6-digalloyl-beta-D-glucopyranose；1,6-bis-O-galloyl-β-D-glucopyranose；1,6-di-O-galloyl-β-D-glucopyranoside；1,6-O-galloyl-glucose；1,6-bis-O-galloyl-beta-D-glucose；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3,4,5-trihydroxybenzoyl)oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 23363-08-8
• 化学式: C₂₀H₂₀O₁₄
• 分子量: 484.37
• InChiKey: LYGRISUQIZNHGM-IVABAYMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  244
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1,6-di-O-galloyl-β-D-glucopyranose 以 aq. buffer 为溶剂， 生成 鞣花酸
  参考文献：
  名称：

  HPLC / DAD–ESI / QTOF / MS检测的碱性条件下可水解单宁的稳定性和氧化产物

  摘要：

  可水解的丹宁酸存在于人类或食草动物用于食品或药品的植物中。碱性条件会改变单宁的结构，即酚基的氧化会导致有毒醌的形成。以前，已经用比色法或电子顺磁共振法研究了这些不稳定的醌类和其他氧化产物，这些方法只能提供有关产物的有限信息。

  DOI：

  10.1002/pca.2456
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 40.0 ℃ 、1.01 MPa 条件下， 反应 12.0h， 以1.2 g的产率得到1,6-di-O-galloyl-β-D-glucopyranose
  参考文献：
  名称：

  The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides

  摘要：

  合成了十二种不同取代模式的鞣酸葡萄糖苷1–12，这些化合物含有两个或三个鞣酸基团，起始材料为商业可得的低成本D-葡萄糖和鞣酸。其中，三种化合物，即甲基3,6-二-O-鞣酸-α-D-葡萄糖吡喃苷（9）、乙基2,3-二-O-鞣酸-α-D-葡萄糖吡喃苷（11）和乙基2,3-二-O-鞣酸-β-D-葡萄糖吡喃苷（12）为新化合物，其余六种化合物，1,6-二-O-鞣酸-β-D-葡萄糖（1）、1,4,6-三-O-鞣酸-β-D-葡萄糖（2）、1,2-二-O-鞣酸-β-D-葡萄糖（3）、1,3-二-O-鞣酸-β-D-葡萄糖（4）、1,2,3-三-O-鞣酸-α-D-葡萄糖（6）和甲基3,4,6-三-O-鞣酸-α-D-葡萄糖吡喃苷（10），在本研究中首次合成。在体外MTT实验中，化合物1–12对人类癌细胞K562、HL-60和HeLa的抑制率在100 μg/mL时范围为64.2%至92.9%，其IC50值在测试的三种人类癌细胞系中变动为17.2–124.7 μM。此外，化合物1–12在体外MTT实验中对小鼠肉瘤S180细胞的抑制率在100 μg/mL时范围为38.7%至52.8%，并且在使用紫杉醇作为阳性对照的情况下，检测到化合物1和2在小鼠肉瘤S180肿瘤-bearing昆明小鼠中的体内抗肿瘤活性。

  DOI：

  10.3390/molecules20022034

文献信息

• Tannins and related compounds. CV. Monomeric and dimeric hydrolyzable tannins having a dehydrohexahydroxydiphenoyl group, supinanin, euphorscopin, euphorhelin and jolkianin, from euphorbia species.
  作者：Seung-Ho LEE、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.39.630

  日期：——

  A chemical investigation of tannins in three Euphorbia species (E. helioscopia, E. jolkini and E. supina) has led to the isolation and characterization of four new hydrolyzable tannins, named supinanin (15), euphorscopin (16), euphorhelin (17) and jolkianin (18), together with fourteen known compounds (1-14). On the basis of chemical and spectroscopic evidence, the structures of supinanin and euphorscopin were established as 1, 3, 6-tri-O-galloyl-2, 4-(S)-dehydrohexahydroxydiphenoyl-β-D-glucose (15) and 1, 3-(S)-dehydrohexahydroxydiphenoyl-2-O-galloyl-4, 6-(S)-hexahydroxydiphenoyl-β-D-glucose (16), respectively. Euphorhelin and jolkianin were characterized as dimeric hydrolyzable tannins (17 and 18, respectively), in which two glucopyranose units are linked via valoneoyl and dehydrodigalloyl groups, respectively, and each molecule possesses a dehydrohexahydroxydiphenoyl group.

  对三种大戟属植物（E. helioscopia, E. jolkini 和 E. supina）中的单宁进行的化学研究导致了四种新可水解单宁的分离和表征，分别命名为supinanin (15)、euphorscopin (16)、euphorhelin (17) 和 jolkianin (18)，以及十四种已知化合物 (1-14)。根据化学和光谱学证据，supinanin 和 euphorscopin 的结构被确立为1, 3, 6-三-O-鞣酸基-2, 4-(S)-脱氢六羟基二苯酰-β-D-葡萄糖 (15) 和1, 3-(S)-脱氢六羟基二苯酰-2-O-鞣酸基-4, 6-(S)-六羟基二苯酰-β-D-葡萄糖 (16)。euphorhelin 和 jolkianin 被特征化为二聚体可水解单宁 (17 和 18)，其中两个葡萄糖单位分别通过瓦碧酸和脱氢二鞣酸基连接，并且每个分子都具有一个脱氢六羟基二苯酰基。
• Tannins and related compounds. XCVI. Structures of macaranins and macarinins, new hydrolyzable tannins possessing macaranoyl and tergalloyl ester groups, from the leaves of Macaranga sinensis (Baill.) Muell.-Arg.
  作者：Jer-Huei LIN、Makoto ISHIMATSU、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.38.1844

  日期：——

  Together with eleven known compounds (1-11), seven new tannins, 3-desgalloylterchebin (12), macaranins A, B and C, and macarinins A, B and C, have been isolated from the leaves of Macaranga sinensis (BAILL.) MUELL.-ARG. (Euphorbiaceae). Macaranins A (14), B (13) and C (17) have been determined on the basis of chemical and spectroscopic evidence to be hydrolyzable tannins possessing a novel acyl group (macaranoly group) at the 3, 6-positions of the 1C4 (or skew boat) β-D-glucopyranose ring, while macarinins A (18), B (15) and (16) were characterized as those having a tergalloyl group at the same positions.

  与已知的十一种化合物（1-11）一起，从Macaranga sinensis (BAILL.) MUELL.-ARG.（大戟科）的叶子中分离出了七种新单宁，分别为3-desgalloylterchebin（12）、macaranins A、B和C。根据化学和光谱证据，确定macaranins A（14）、B（13）和C（17）为可水解的单宁，具有在1C4（或倾斜船型）β-D-葡萄糖环的3、6位上的新型酰基（macaranoly基团），而macarinins A（18）、B（15）和C（16）被鉴定为在相同位置具有tergalloyl基团的化合物。
• LIN, JER-HUEI;ISHIMATSU, MAKOTO;TANAKA, TAKASHI;NONAKA, GEN-ICHIRO;NISHIO+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1844-1851
  作者：LIN, JER-HUEI、ISHIMATSU, MAKOTO、TANAKA, TAKASHI、NONAKA, GEN-ICHIRO、NISHIO+

  DOI：——

  日期：——
• Biosynthesis of gallotannins. Enzymatic conversion of 1,6-digalloylglucose to 1,2,6-trigalloylglucose
  作者：Klaus Denzel、Gerhard Schilling、Georg G. Gross

  DOI：10.1007/bf00392489

  日期：——

  Cell-free extracts from Rhus typhina L. (staghorn sumach) leaves were found to catalyze the transfer of the galloyl moiety of β-glucogallin (1-O-galloyl-β-D-glucose) to 1,6-di-O-galloyl-β-D-glucose, resulting in the specific formation of 1,2,6-tri-O-galloyl-β-D-glucose, an intermediate of gallotannin biosynthesis. The reaction product was unequivocally identified by co-chromatography with authentic references using reversed-phase high-performance liquid chromatography and by (1)H-nuclear-magnetic-resonance spectroscopy.
• PHYLLANTHUS AMARUS COMPOSITIONS AND METHOD OF EXTRACTING SAME
  申请人：Natreon, Inc.

  公开号：US20130122119A1

  公开（公告）日：2013-05-16

  An enriched hydrolyzable tannin blend derived from Phyllanthus amarus is provided. An optimized aqueous extraction method for Phyllanthus amarus is provided to maximize the levels of bioactive hydrolyzable tannins including corilagin, geraniin, nirurin and other low molecular weight hydrolyzable tannoids. The method produces a Phyllanthus amarus extract containing a hydrolyzable tannin blend as an amorphous dry powder. In an embodiment, the Phyllanthus amarus extract contains 7-13% by weight corilagin, 3.5-10% nirurin, 1-2% geraniin, and 9-20% low molecular weight hydrolyzable tannoids. In another embodiment, the Phyllanthus amarus extract contains 12-20% geraniin and 12-20% low molecular weight hydrolyzable tannoids. Potential uses of said enriched hydrolyzable tannin compositions for hepatoprotection in a human subject are described herein.